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Virtually Staged. Nestled on an OVERSIZED HOMESITE of well over half an acre in the sought-after Lake Ann Estates of Winter Park, this BEAUTIFULLY UPDATED 4-bedroom, 3-bath pool home offers the perfect combination of space, style, and freedom with NO HOA. Surrounded by MATURE LANDSCAPING and offering more than 2,600 SQUARE FEET of thoughtfully designed living space, this single-story residence is ready to impress from the moment you arrive. Step through the ELEGANT ETCHED GLASS FRONT DOOR and into a home where crown molding and tile flooring flow throughout—with NO CARPET to be found. The spacious Family Room flows effortlessly into a VERSATILE BONUS SPACE, ideal as a media room, game room, or second living area, with sliding glass doors opening to the patio and pool for seamless indoor-outdoor entertaining. At the heart of the home, the STUNNING KITCHEN is designed for both everyday living and hosting with ease. Rich wood cabinetry, abundant counter space, a center island, SLEEK TILE BACKSPLASH, stainless steel appliances, a closet pantry, and a SPACIOUS BREAKFAST NOOK provide everything the home chef needs. Overlooking the inviting Living Room, the space is accented by exposed wood ceiling beams, a COZY FIREPLACE, built-in shelving, and NATURAL LIGHT flowing through another set of French doors that beautifully blend indoor and outdoor living.The spacious Primary Suite offers a peaceful escape with a generous walk-in closet and a beautifully appointed EN SUITE BATH featuring dual sinks and a large tiled walk-in shower. Three additional bedrooms provide flexibility for family, guests, or hobbies. Two share a convenient JACK-AND-JILL BATH, while the fourth bedroom features BUILT-IN CABINETRY, making it an ideal home office or creative workspace. Step outside and discover your own PRIVATE OASIS where a brick paver patio surrounds a sparkling in-ground pool, creating the perfect place to soak up the Florida sunshine. The EXPANSIVE BACKYARD offers endless possibilities with a charming gazebo, a cozy fire pit for evening gatherings, and a storage shed for added convenience. Additional highlights include a roof replaced approximately 10 years ago and SOLAR HEATING, helping to reduce energy costs while adding long-term value. Located within the highly acclaimed Seminole County School District, this exceptional home is JUST MINUES from Park Avenue's boutiques, dining, and seasonal events, Rollins College, Winter Park Village, AdventHealth Winter Park, and nearby shopping and restaurants. Enjoy EASY ACCESS to Maitland, Downtown Orlando, and major roadways, while outdoor enthusiasts will appreciate nearby parks, lakes, golf courses, and the CADY WAY TRAIL. Opportunities to own a BEAUTIFULLY UPDATED POOL HOME on a lot of this size in Winter Park are rare—don't miss your chance to make this exceptional property your own!

4 Beds ⋅ 3 Baths ⋅ Lake Ann Estates Unit 2 SubDv. ⋅ 32792 Zip Code

Virtually Staged. Nestled on an OVERSIZED HOMESITE of well over half an acre in the sought-after Lake Ann Estates of Winter Park, this BEAUTIFULLY UPDATED 4-bedroom, 3-bath pool home offers the perfect combination of space, style, and freedom with NO HOA. Surrounded by MATURE LANDSCAPING and offering more than 2,600 SQUARE FEET of thoughtfully designed living space, this single-story residence is ready to impress from the moment you arrive. Step through the ELEGANT ETCHED GLASS FRONT DOOR and into a home where crown molding and tile flooring flow throughout—with NO CARPET to be found. The spacious Family Room flows effortlessly into a VERSATILE BONUS SPACE, ideal as a media room, game room, or second living area, with sliding glass doors opening to the patio and pool for seamless indoor-outdoor entertaining. At the heart of the home, the STUNNING KITCHEN is designed for both everyday living and hosting with ease. Rich wood cabinetry, abundant counter space, a center island, SLEEK TILE BACKSPLASH, stainless steel appliances, a closet pantry, and a SPACIOUS BREAKFAST NOOK provide everything the home chef needs. Overlooking the inviting Living Room, the space is accented by exposed wood ceiling beams, a COZY FIREPLACE, built-in shelving, and NATURAL LIGHT flowing through another set of French doors that beautifully blend indoor and outdoor living.The spacious Primary Suite offers a peaceful escape with a generous walk-in closet and a beautifully appointed EN SUITE BATH featuring dual sinks and a large tiled walk-in shower. Three additional bedrooms provide flexibility for family, guests, or hobbies. Two share a convenient JACK-AND-JILL BATH, while the fourth bedroom features BUILT-IN CABINETRY, making it an ideal home office or creative workspace. Step outside and discover your own PRIVATE OASIS where a brick paver patio surrounds a sparkling in-ground pool, creating the perfect place to soak up the Florida sunshine. The EXPANSIVE BACKYARD offers endless possibilities with a charming gazebo, a cozy fire pit for evening gatherings, and a storage shed for added convenience. Additional highlights include a roof replaced approximately 10 years ago and SOLAR HEATING, helping to reduce energy costs while adding long-term value. Located within the highly acclaimed Seminole County School District, this exceptional home is JUST MINUES from Park Avenue's boutiques, dining, and seasonal events, Rollins College, Winter Park Village, AdventHealth Winter Park, and nearby shopping and restaurants. Enjoy EASY ACCESS to Maitland, Downtown Orlando, and major roadways, while outdoor enthusiasts will appreciate nearby parks, lakes, golf courses, and the CADY WAY TRAIL. Opportunities to own a BEAUTIFULLY UPDATED POOL HOME on a lot of this size in Winter Park are rare—don't miss your chance to make this exceptional property your own!

110 Longhorn Road, Winter Park

$590,000

MOTIVATED SELLER – QUICK CLOSE AVAILABLE! Welcome to this beautifully maintained 4-bedroom, 2-bath home in the desirable Kings Cove community of Winter Park. From the moment you arrive, you'll appreciate the spacious layout and impressive updates throughout. The heart of the home features a beautifully appointed kitchen with quartz countertops, ample cabinetry, and a seamless flow into the family room, making it perfect for everyday living and entertaining. Vaulted ceilings and a cozy wood-burning fireplace create a warm and inviting atmosphere. Step outside to your own private outdoor oasis. The screened-in pool area is designed for year-round enjoyment and features a spacious patio, covered lanai, and a fully equipped outdoor kitchen complete with refrigerator, sink, and cabinetry—ideal for hosting family and friends. The primary suite offers a relaxing retreat with dual sinks and plenty of space to unwind. Additional highlights include a fenced backyard, new windows (2021), new roof (2019), and a new AC system (2024), providing peace of mind for years to come. Conveniently located with easy access to SR 417, shopping, dining, and everyday conveniences, this exceptional home combines comfort, style, and location. Don't miss this opportunity—schedule your private showing today!

4 Beds ⋅ 2 Baths ⋅ Kings Cove SubDv. ⋅ 32792 Zip Code

MOTIVATED SELLER – QUICK CLOSE AVAILABLE! Welcome to this beautifully maintained 4-bedroom, 2-bath home in the desirable Kings Cove community of Winter Park. From the moment you arrive, you'll appreciate the spacious layout and impressive updates throughout. The heart of the home features a beautifully appointed kitchen with quartz countertops, ample cabinetry, and a seamless flow into the family room, making it perfect for everyday living and entertaining. Vaulted ceilings and a cozy wood-burning fireplace create a warm and inviting atmosphere. Step outside to your own private outdoor oasis. The screened-in pool area is designed for year-round enjoyment and features a spacious patio, covered lanai, and a fully equipped outdoor kitchen complete with refrigerator, sink, and cabinetry—ideal for hosting family and friends. The primary suite offers a relaxing retreat with dual sinks and plenty of space to unwind. Additional highlights include a fenced backyard, new windows (2021), new roof (2019), and a new AC system (2024), providing peace of mind for years to come. Conveniently located with easy access to SR 417, shopping, dining, and everyday conveniences, this exceptional home combines comfort, style, and location. Don't miss this opportunity—schedule your private showing today!

4353 Steed Terrace, Winter Park

$1,342,500

NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by SGC Construction! This stunning new Mid-Century Modern–inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows seamlessly into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool and lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with a double vanity, freestanding soaking tub, and a spacious walk-in closet with custom shelving. Upstairs, a large bonus room with a closet offers versatility as a fifth bedroom, game room, or home office. Two additional bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!

4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by SGC Construction! This stunning new Mid-Century Modern–inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows seamlessly into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool and lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with a double vanity, freestanding soaking tub, and a spacious walk-in closet with custom shelving. Upstairs, a large bonus room with a closet offers versatility as a fifth bedroom, game room, or home office. Two additional bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!

1540 Miller Avenue, Winter Park

$325,000

**RARE WINTER PARK OPPORTUNITY!** Bring your vision to this 1959 block home situated on a spacious 0.25-acre lot in the City of Winter Park, with the prestigious Interlachen Country Club golf course directly behind the property. Whether you choose to renovate the existing 4-bedroom, 2-bath home or pursue a complete redevelopment, this property offers an exceptional opportunity to create something special in a highly desirable location. The existing home features solid block construction, 4 bedrooms, 2 bathrooms, a concrete swimming pool, and a 2019 roof, providing a great starting point for renovation or redevelopment. The generous lot and established location offer plenty of potential for a new custom residence designed to take advantage of the surrounding Winter Park lifestyle and golf-course setting. Enjoy convenient access to some of Central Florida's most sought-after amenities, including Interlachen Country Club, Park Avenue, Downtown Winter Park, Winter Park Village, Rollins College, Central Park, shopping, dining, parks, and cultural attractions. Interlachen's 18-hole championship golf course provides a beautiful backdrop just beyond the property, while Winter Park's renowned Park Avenue district offers upscale shopping, restaurants, galleries and entertainment nearby. An excellent opportunity for builders, investors, renovators or buyers looking to create their own Winter Park residence in an established setting surrounded by golf, dining, shopping and recreation.

4 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code

**RARE WINTER PARK OPPORTUNITY!** Bring your vision to this 1959 block home situated on a spacious 0.25-acre lot in the City of Winter Park, with the prestigious Interlachen Country Club golf course directly behind the property. Whether you choose to renovate the existing 4-bedroom, 2-bath home or pursue a complete redevelopment, this property offers an exceptional opportunity to create something special in a highly desirable location. The existing home features solid block construction, 4 bedrooms, 2 bathrooms, a concrete swimming pool, and a 2019 roof, providing a great starting point for renovation or redevelopment. The generous lot and established location offer plenty of potential for a new custom residence designed to take advantage of the surrounding Winter Park lifestyle and golf-course setting. Enjoy convenient access to some of Central Florida's most sought-after amenities, including Interlachen Country Club, Park Avenue, Downtown Winter Park, Winter Park Village, Rollins College, Central Park, shopping, dining, parks, and cultural attractions. Interlachen's 18-hole championship golf course provides a beautiful backdrop just beyond the property, while Winter Park's renowned Park Avenue district offers upscale shopping, restaurants, galleries and entertainment nearby. An excellent opportunity for builders, investors, renovators or buyers looking to create their own Winter Park residence in an established setting surrounded by golf, dining, shopping and recreation.

5218 Lake Howell Road, Winter Park

$300,000

Solid, mid-century modern house for growing family, in need of a little love, located in a quiet Winter Park neighborhood. HUGE backyard, with large covered open patio. One of the largest lots in the subdivision, with best configuration for possible growth opportunities. Mature trees in peaceful, fully fenced backyard. 4 bedroom, 2.5 bath with a split floor plan. Also, a possible redevelopment opportunity for builders and investors. New roof 2025, new HVAC system 2020, new water heater 2024, upgraded electric panel, re-piping of water system with Pex in 2010. Terrazzo and concrete flooring. Priced as-is for buyer to provide own upgrades. Located in Seminole County, just minutes from downtown Winter Park, YMCA, hospital, Rollins, Full Sail and UCF universities. Short distance to downtown Orlando, Orlando International Airport, Sanford Airport, theme parks and easy access to beaches on both coasts.

4 Beds ⋅ 3 Baths ⋅ Ridge High Sub SubDv. ⋅ 32792 Zip Code

Solid, mid-century modern house for growing family, in need of a little love, located in a quiet Winter Park neighborhood. HUGE backyard, with large covered open patio. One of the largest lots in the subdivision, with best configuration for possible growth opportunities. Mature trees in peaceful, fully fenced backyard. 4 bedroom, 2.5 bath with a split floor plan. Also, a possible redevelopment opportunity for builders and investors. New roof 2025, new HVAC system 2020, new water heater 2024, upgraded electric panel, re-piping of water system with Pex in 2010. Terrazzo and concrete flooring. Priced as-is for buyer to provide own upgrades. Located in Seminole County, just minutes from downtown Winter Park, YMCA, hospital, Rollins, Full Sail and UCF universities. Short distance to downtown Orlando, Orlando International Airport, Sanford Airport, theme parks and easy access to beaches on both coasts.

2122 Ridge Drive, Winter Park

$649,000

THE best kept secret in WP! Newly renovated charming bungalow located directly on famed 4th Fairway on WP9 – Winter Park Golf Course! Quiet, private & secluded setting with gorgeous views on dead end street. Walk or bike to Park Avenue, dining and shopping, Rollins College and Winter Park Village. New roof and water heater 2023, refinished hardwood floors, new kitchen with stainless appliances, renovated bath, 3 generous bedrooms, bonus Florida Room, PLUS single car garage. Open patio in backyard with separate firepit seating area overlooking the golf course. Great rental and/or build your dream home! Don’t miss this “one of a kind – live your best Winter Park life” opportunity!

3 Beds ⋅ 1 Baths ⋅ Tantum Add SubDv. ⋅ 32789 Zip Code

THE best kept secret in WP! Newly renovated charming bungalow located directly on famed 4th Fairway on WP9 – Winter Park Golf Course! Quiet, private & secluded setting with gorgeous views on dead end street. Walk or bike to Park Avenue, dining and shopping, Rollins College and Winter Park Village. New roof and water heater 2023, refinished hardwood floors, new kitchen with stainless appliances, renovated bath, 3 generous bedrooms, bonus Florida Room, PLUS single car garage. Open patio in backyard with separate firepit seating area overlooking the golf course. Great rental and/or build your dream home! Don’t miss this “one of a kind – live your best Winter Park life” opportunity!

1037 N Virginia Avenue, Winter Park

$525,000

Welcome to 410 Saint Dunstan Way, a beautifully maintained 3-bedroom, 2-bath home ideally located in desirable Winter Park. Situated on a spacious .22-acre lot with **no HOA**, this property offers an excellent combination of comfort, convenience, and value. Offering 1,519 square feet of thoughtfully designed living space, the home features a functional floor plan with generous living and dining areas, abundant natural light, and a comfortable flow that's ideal for both everyday living and entertaining. **With no carpet throughout the home**, the interior offers easy-to-maintain flooring and a clean, cohesive feel. The kitchen overlooks the main living spaces, creating a welcoming setting for gatherings with family and friends. The spacious primary suite provides a private retreat, while two additional bedrooms offer flexibility for guests, a home office, or additional living space. Step outside and enjoy the large backyard with plenty of room for outdoor entertaining, gardening, pets, or the possibility of a future pool. Additional highlights include a 2-car garage, mature landscaping, and an established neighborhood setting. Conveniently located near shopping, dining, parks, major roadways, and all that Winter Park has to offer, this home provides the added freedom of **no mandatory HOA** while still enjoying a strong sense of community. Whether you're searching for your first home, your next home, or an investment opportunity in one of Central Florida's most desirable markets, 410 Saint Dunstan Way is ready to impress. **Schedule your private showing today and experience the Winter Park lifestyle for yourself.**

3 Beds ⋅ 2 Baths ⋅ Winter Park Pines Unit 4 SubDv. ⋅ 32792 Zip Code

Welcome to 410 Saint Dunstan Way, a beautifully maintained 3-bedroom, 2-bath home ideally located in desirable Winter Park. Situated on a spacious .22-acre lot with **no HOA**, this property offers an excellent combination of comfort, convenience, and value. Offering 1,519 square feet of thoughtfully designed living space, the home features a functional floor plan with generous living and dining areas, abundant natural light, and a comfortable flow that's ideal for both everyday living and entertaining. **With no carpet throughout the home**, the interior offers easy-to-maintain flooring and a clean, cohesive feel. The kitchen overlooks the main living spaces, creating a welcoming setting for gatherings with family and friends. The spacious primary suite provides a private retreat, while two additional bedrooms offer flexibility for guests, a home office, or additional living space. Step outside and enjoy the large backyard with plenty of room for outdoor entertaining, gardening, pets, or the possibility of a future pool. Additional highlights include a 2-car garage, mature landscaping, and an established neighborhood setting. Conveniently located near shopping, dining, parks, major roadways, and all that Winter Park has to offer, this home provides the added freedom of **no mandatory HOA** while still enjoying a strong sense of community. Whether you're searching for your first home, your next home, or an investment opportunity in one of Central Florida's most desirable markets, 410 Saint Dunstan Way is ready to impress. **Schedule your private showing today and experience the Winter Park lifestyle for yourself.**

410 Saint Dunstan Way, Winter Park

106 S Interlachen Avenue Unit 518, Winter Park

$1,735,000

Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural recessed lighting, and custom-tailored interior doors with modern glass knob hardware. With two walls of glass, the main living space extends to a generous wraparound balcony set among lush treetops and endless lake views—the perfect backdrop for morning coffee, sunset cocktails, and open-air entertaining. A restored floor-to-ceiling brick fireplace is a dramatic centerpiece, pairing modern simplicity with timeless appeal, that adds warmth and ambiance. The striking kitchen blends clean lines with elevated finishes. Crafted maple cabinetry rises to the ceiling, complemented by sleek hardware and under-cabinet lighting that softly highlights a dimensional subway tile backsplash for added depth and texture. Crisp quartz countertops provide a seamless surface, while a suite of premium Jenn Air appliances delivers both statement-making design and top-tier performance. A large peninsula offers generous seating and gathering space—ideal for casual dining or entertaining—and incorporates a discreetly integrated pet station, a thoughtful detail that enhances daily living. Open to the surrounding spaces, the entire space feels cohesive, inviting, and effortlessly functional. The primary suite is thoughtfully planned to provide a calm and comfortable retreat, featuring truly custom closet cabinetry for streamlined storage. Expansive windows frame serene lake views and a lush green backdrop, creating a tranquil, ever-changing setting—wake to soft morning light shimmering across the water and unwind in the evening with a sense of quiet ease. Also designed with intention and precision, the primary bath maximizes space with more custom cabinetry for additional clothing storage, a streamlined vanity with quartz counter, integrated laundry cabinet, and glass-enclosed shower—all executed in a refined palette that feels both elevated and livable. The inviting second bedroom is enhanced by a built-in closet offering a polished and highly functional storage solution. Equally well considered, the second bath features quartz counters and lots of custom cabinetry for a clean, detailed look. A seamless glass shower is complimented by a strategically placed frosted entry panel offering privacy without sacrificing natural light, while a full-width mirror amplifies the sense of space. The third bedroom offers a thoughtfully designed double desk, a customized closet for added style and function and sliding glass doors to the balcony for natural light and an outdoor connection. New laundry room is both functional and refined, featuring folding counter, abundant cabinetry, and a dedicated hanging area with a built-in bench & storage drawer. Custom integrated doors discreetly conceal mechanicals. The residence also includes assigned covered parking. Residents of The Cloisters enjoy a lakefront lifestyle with dock access, boat slips, along with/ other amenities including a fitness center, and renovated clubhouse w/ kitchen, putting green and pool—all supported by a professional on-site management and beautifully maintained grounds.

3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural recessed lighting, and custom-tailored interior doors with modern glass knob hardware. With two walls of glass, the main living space extends to a generous wraparound balcony set among lush treetops and endless lake views—the perfect backdrop for morning coffee, sunset cocktails, and open-air entertaining. A restored floor-to-ceiling brick fireplace is a dramatic centerpiece, pairing modern simplicity with timeless appeal, that adds warmth and ambiance. The striking kitchen blends clean lines with elevated finishes. Crafted maple cabinetry rises to the ceiling, complemented by sleek hardware and under-cabinet lighting that softly highlights a dimensional subway tile backsplash for added depth and texture. Crisp quartz countertops provide a seamless surface, while a suite of premium Jenn Air appliances delivers both statement-making design and top-tier performance. A large peninsula offers generous seating and gathering space—ideal for casual dining or entertaining—and incorporates a discreetly integrated pet station, a thoughtful detail that enhances daily living. Open to the surrounding spaces, the entire space feels cohesive, inviting, and effortlessly functional. The primary suite is thoughtfully planned to provide a calm and comfortable retreat, featuring truly custom closet cabinetry for streamlined storage. Expansive windows frame serene lake views and a lush green backdrop, creating a tranquil, ever-changing setting—wake to soft morning light shimmering across the water and unwind in the evening with a sense of quiet ease. Also designed with intention and precision, the primary bath maximizes space with more custom cabinetry for additional clothing storage, a streamlined vanity with quartz counter, integrated laundry cabinet, and glass-enclosed shower—all executed in a refined palette that feels both elevated and livable. The inviting second bedroom is enhanced by a built-in closet offering a polished and highly functional storage solution. Equally well considered, the second bath features quartz counters and lots of custom cabinetry for a clean, detailed look. A seamless glass shower is complimented by a strategically placed frosted entry panel offering privacy without sacrificing natural light, while a full-width mirror amplifies the sense of space. The third bedroom offers a thoughtfully designed double desk, a customized closet for added style and function and sliding glass doors to the balcony for natural light and an outdoor connection. New laundry room is both functional and refined, featuring folding counter, abundant cabinetry, and a dedicated hanging area with a built-in bench & storage drawer. Custom integrated doors discreetly conceal mechanicals. The residence also includes assigned covered parking. Residents of The Cloisters enjoy a lakefront lifestyle with dock access, boat slips, along with/ other amenities including a fitness center, and renovated clubhouse w/ kitchen, putting green and pool—all supported by a professional on-site management and beautifully maintained grounds.

106 S Interlachen Avenue Unit 518, Winter Park

$3,550,000

In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement with organic warmth. Now offered at a compelling new price, the home presents a rare opportunity to experience architecturally distinctive new construction in the Vias neighborhood. Conceived, developed & designed by Steve & Jodie Konold of Scout & Co., the 3,826-sf residence offers 4 beds & 5.5 baths, w/ a layout thoughtfully arranged to provide the intentional privacy of a luxury retreat. Beyond its terraced walkway—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer featuring a woven rattan chandelier, sourced & designed in London, leads to a sculptural stairwell positioned just off the main living spaces. The great room includes soaring ceilings, a sleek, custom plaster fireplace & walls of glass doors & windows. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. The kitchen is appointed w/ a Thermador dual-fuel range, matching plaster hood, full refrigerator & freezer columns & a large island with seating topped in honed black quartzite. The surrounding cabinetry features hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces line the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balances the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The main floor primary suite is accessed through antique doors that open to a light-filled gallery overlooking the rear courtyard & pool. The primary bath features an extended vanity w/ dual sinks, matte black fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink paired w/ a handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby bedroom suite is marked by an antique door entry. Each guest bedroom features an en-suite bath introduced by a hand-painted tile threshold, complemented by designer lighting, distinctive mirrors & continuous European oak flooring. The rooftop terrace is accessed from the second-floor hallway. The detached casita opens to the pool courtyard through accordion glass doors on two walls & includes a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Other outdoor spaces include 2 garden courtyards, a heated saltwater pool & a newly constructed outdoor kitchen designed to accommodate a built-in grill & Big Green Egg. A spacious gravel courtyard is ideal for dining or relaxing and is enveloped by mature bamboo that creates exceptional privacy. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle within one of Winter Park’s most exclusive enclaves.

4 Beds ⋅ 6 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code

In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement with organic warmth. Now offered at a compelling new price, the home presents a rare opportunity to experience architecturally distinctive new construction in the Vias neighborhood. Conceived, developed & designed by Steve & Jodie Konold of Scout & Co., the 3,826-sf residence offers 4 beds & 5.5 baths, w/ a layout thoughtfully arranged to provide the intentional privacy of a luxury retreat. Beyond its terraced walkway—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer featuring a woven rattan chandelier, sourced & designed in London, leads to a sculptural stairwell positioned just off the main living spaces. The great room includes soaring ceilings, a sleek, custom plaster fireplace & walls of glass doors & windows. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. The kitchen is appointed w/ a Thermador dual-fuel range, matching plaster hood, full refrigerator & freezer columns & a large island with seating topped in honed black quartzite. The surrounding cabinetry features hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces line the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balances the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The main floor primary suite is accessed through antique doors that open to a light-filled gallery overlooking the rear courtyard & pool. The primary bath features an extended vanity w/ dual sinks, matte black fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink paired w/ a handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby bedroom suite is marked by an antique door entry. Each guest bedroom features an en-suite bath introduced by a hand-painted tile threshold, complemented by designer lighting, distinctive mirrors & continuous European oak flooring. The rooftop terrace is accessed from the second-floor hallway. The detached casita opens to the pool courtyard through accordion glass doors on two walls & includes a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Other outdoor spaces include 2 garden courtyards, a heated saltwater pool & a newly constructed outdoor kitchen designed to accommodate a built-in grill & Big Green Egg. A spacious gravel courtyard is ideal for dining or relaxing and is enveloped by mature bamboo that creates exceptional privacy. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle within one of Winter Park’s most exclusive enclaves.

1150 Via Salerno, Winter Park

100 S Interlachen Avenue Unit 101, Winter Park

$1,185,000

On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Park’s accessible lakefront communities. An oversized tiled patio, partially covered and ideal for outdoor dining or morning coffee, extends the living space and enhances everyday functionality. Renovated in 2021 by Charles Clayton Construction, an award-winning luxury homebuilder, the residence features updated flooring, kitchen, baths, lighting and laundry. Wood flooring flows through the foyer, dining and living areas, while ceramic tile is installed in the bedrooms, and decorative tile in the baths. The kitchen is appointed with high-end appliances and custom solid wood cabinetry, designed for daily living and entertaining. The primary suite offers abundant natural light, a built-in closet and an en-suite bath with dual sinks, walk-in shower and a window providing natural illumination. A hall bath includes a tub-shower combination and additional storage. A sunroom off the third bedroom provides flexible space for a private office, den or reading room. The residence includes one assigned covered carport space and a dedicated climate-controlled storage unit on site. Two blocks from Park Avenue, residents enjoy convenient access to dining, shopping and cultural amenities in a lakefront community setting. The property presents an opportunity for full-time living, luxury downsizing or lock-and-leave lifestyle in the heart of Winter Park.

3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Park’s accessible lakefront communities. An oversized tiled patio, partially covered and ideal for outdoor dining or morning coffee, extends the living space and enhances everyday functionality. Renovated in 2021 by Charles Clayton Construction, an award-winning luxury homebuilder, the residence features updated flooring, kitchen, baths, lighting and laundry. Wood flooring flows through the foyer, dining and living areas, while ceramic tile is installed in the bedrooms, and decorative tile in the baths. The kitchen is appointed with high-end appliances and custom solid wood cabinetry, designed for daily living and entertaining. The primary suite offers abundant natural light, a built-in closet and an en-suite bath with dual sinks, walk-in shower and a window providing natural illumination. A hall bath includes a tub-shower combination and additional storage. A sunroom off the third bedroom provides flexible space for a private office, den or reading room. The residence includes one assigned covered carport space and a dedicated climate-controlled storage unit on site. Two blocks from Park Avenue, residents enjoy convenient access to dining, shopping and cultural amenities in a lakefront community setting. The property presents an opportunity for full-time living, luxury downsizing or lock-and-leave lifestyle in the heart of Winter Park.

100 S Interlachen Avenue Unit 101, Winter Park

$1,654,000

Picturesque and beautifully appointed, this three-bedroom, three-bath residence is ideally situated along the sought-after Vias of Winter Park, a charming brick-paved street framed by mature landscaping and distinguished residences. Meticulously maintained grounds surround the home, with brick-paver walkways and inviting side and rear courtyards creating a seamless connection between the indoors and outdoors. Inside, gorgeous wood floors extend throughout the first level, complimented by soaring ceilings and an abundance of windows that fill the home with natural light. The spacious living room features a striking wood-burning fireplace and an impressive ceiling height, creating an inviting setting for both everyday living and entertaining. The well-designed kitchen offers an island, stainless steel appliances and excellent functionality, while an adjacent breakfast nook features a custom built-in bar and beverage center with under-counter refrigerator. The elegant dining room has a set of French doors overlooking lush greenery and the home's beautifully landscaped backyard. Thoughtfully renovated by the current owners, the first floor was reconfigured to create a luxurious primary suite with soaring ceilings and French doors opening to tranquil courtyard views. The spacious walk-in closet and newly added ensuite bath complete this private retreat. A second bedroom, a full bath, and a dedicated laundry room round out the main level. Upstairs, an open loft provides versatile additional living space, while a generously sized third bedroom suite offers exceptional privacy and flexibility. With a spacious walk-in closet and spa-inspired bath, this expansive suite could easily serve as a secondary primary retreat. Beyond the remote-controlled driveway gate, a detached two-car garage provides exceptional convenience and storage, while the upstairs loft/flex space of 480 sq ft (NOT included in main house heated SF) offers endless possibilities for a fitness studio, yoga retreat, creative space or home office. The location is truly exceptional, with the Winter Park Racquet Club and Kraft Azalea Garden just a short walk or bike ride away. Park Avenue's renowned shopping, dining, sidewalk cafés and cultural attractions are only minutes from home, along with everything downtown Winter Park has to offer. Convenient access to highly regarded public and private schools further enhances the appeal of this special property. A rare combination of thoughtful renovation, timeless character, exceptional outdoor spaces and an enviable Winter Park location, this beautifully presented residence offers a refined yet comfortable lifestyle in one of the area's most coveted settings.

3 Beds ⋅ 3 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code

Picturesque and beautifully appointed, this three-bedroom, three-bath residence is ideally situated along the sought-after Vias of Winter Park, a charming brick-paved street framed by mature landscaping and distinguished residences. Meticulously maintained grounds surround the home, with brick-paver walkways and inviting side and rear courtyards creating a seamless connection between the indoors and outdoors. Inside, gorgeous wood floors extend throughout the first level, complimented by soaring ceilings and an abundance of windows that fill the home with natural light. The spacious living room features a striking wood-burning fireplace and an impressive ceiling height, creating an inviting setting for both everyday living and entertaining. The well-designed kitchen offers an island, stainless steel appliances and excellent functionality, while an adjacent breakfast nook features a custom built-in bar and beverage center with under-counter refrigerator. The elegant dining room has a set of French doors overlooking lush greenery and the home's beautifully landscaped backyard. Thoughtfully renovated by the current owners, the first floor was reconfigured to create a luxurious primary suite with soaring ceilings and French doors opening to tranquil courtyard views. The spacious walk-in closet and newly added ensuite bath complete this private retreat. A second bedroom, a full bath, and a dedicated laundry room round out the main level. Upstairs, an open loft provides versatile additional living space, while a generously sized third bedroom suite offers exceptional privacy and flexibility. With a spacious walk-in closet and spa-inspired bath, this expansive suite could easily serve as a secondary primary retreat. Beyond the remote-controlled driveway gate, a detached two-car garage provides exceptional convenience and storage, while the upstairs loft/flex space of 480 sq ft (NOT included in main house heated SF) offers endless possibilities for a fitness studio, yoga retreat, creative space or home office. The location is truly exceptional, with the Winter Park Racquet Club and Kraft Azalea Garden just a short walk or bike ride away. Park Avenue's renowned shopping, dining, sidewalk cafés and cultural attractions are only minutes from home, along with everything downtown Winter Park has to offer. Convenient access to highly regarded public and private schools further enhances the appeal of this special property. A rare combination of thoughtful renovation, timeless character, exceptional outdoor spaces and an enviable Winter Park location, this beautifully presented residence offers a refined yet comfortable lifestyle in one of the area's most coveted settings.

1200 Woodmere Drive, Winter Park

3381 Cedar Springs Place Unit 151, Winter Park

$185,000

Move right in and enjoy low-maintenance living in the desirable Hidden Oaks community of Winter Park. This meticulous maintained and nicely updated 2-bedroom, 2.5-bath townhome-style condo features two spacious primary suites, each with its own private en-suite bathroom, offering a flexible floor plan and exceptional functionality. The open and inviting layout includes an oversized great room, 12-inch ceramic tile flooring, and a well-appointed kitchen with maple cabinetry, Corian countertops, flat-top range, stainless steel refrigerator, and new microwave, new blinds throughout. The washer and dryer are included, making this home truly move-in ready. Both bathrooms have been tastefully updated, maple cabinetry, one with granite & one with Corian countertops for a cohesive, modern look. Enjoy outdoor living on the private rear patio, complete with space for grilling and an additional storage closet. Hidden Oaks is a beautifully maintained community featuring mature landscaping, a community pool, and a convenient Winter Park location near shopping, dining, entertainment, major employers, and highly rated Winter Park schools. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities, creating an easy lock-and-leave lifestyle. Conveniently located near Full Sail University, the University of Central Florida, Downtown Winter Park, and major roadways, this home offers an excellent opportunity for owner-occupants, those seeking a second home, or buyers looking for a long-term investment property. Don't miss the chance to own a well-maintained and move-in-ready home in one of Winter Park's most convenient locations.

2 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 09 SubDv. ⋅ 32792 Zip Code

Move right in and enjoy low-maintenance living in the desirable Hidden Oaks community of Winter Park. This meticulous maintained and nicely updated 2-bedroom, 2.5-bath townhome-style condo features two spacious primary suites, each with its own private en-suite bathroom, offering a flexible floor plan and exceptional functionality. The open and inviting layout includes an oversized great room, 12-inch ceramic tile flooring, and a well-appointed kitchen with maple cabinetry, Corian countertops, flat-top range, stainless steel refrigerator, and new microwave, new blinds throughout. The washer and dryer are included, making this home truly move-in ready. Both bathrooms have been tastefully updated, maple cabinetry, one with granite & one with Corian countertops for a cohesive, modern look. Enjoy outdoor living on the private rear patio, complete with space for grilling and an additional storage closet. Hidden Oaks is a beautifully maintained community featuring mature landscaping, a community pool, and a convenient Winter Park location near shopping, dining, entertainment, major employers, and highly rated Winter Park schools. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities, creating an easy lock-and-leave lifestyle. Conveniently located near Full Sail University, the University of Central Florida, Downtown Winter Park, and major roadways, this home offers an excellent opportunity for owner-occupants, those seeking a second home, or buyers looking for a long-term investment property. Don't miss the chance to own a well-maintained and move-in-ready home in one of Winter Park's most convenient locations.

3381 Cedar Springs Place Unit 151, Winter Park

311 E Morse Boulevard Unit 6-12, Winter Park

$267,500

Welcome to easy living in the heart of Winter Park. Located just two blocks from Park Avenue, this studio condo puts you right in the center of it all—award-winning restaurants, boutique shopping, coffee shops, museums, and the iconic Winter Park boat tour are all just steps away. Situated on the third floor of Building 6 with convenient elevator access, this light-filled unit offers a surprisingly flexible layout. The current owner has creatively configured the space with separate living and dining areas, while the enclosed porch serves as a bedroom. The updated kitchen features decorative tile flooring, stainless steel appliances, and solid wood cabinetry. Sliding glass doors lead to a bonus room that can easily function as a home office, guest space, workout room, or additional living area. The bathroom includes a single vanity and tub/shower combination, and you'll appreciate the abundance of storage throughout the unit. One of the biggest advantages of this property is the peace of mind that comes with a monthly HOA fee that covers nearly everything—including electric, water, sewer, trash, building insurance, landscaping, pool maintenance, and on-site management. . Whispering Waters recently passed its structural integrity inspection and reserve study with excellent results, reflecting the care and quality of this well-managed community. Residents also enjoy access to beautiful Lake Osceola, where you can launch a kayak, relax by the water, or take in breathtaking sunset views. Whether you're looking for a full-time residence or a seasonal retreat this condo offers an unbeatable Winter Park location and true lock-and-leave convenience.

1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Welcome to easy living in the heart of Winter Park. Located just two blocks from Park Avenue, this studio condo puts you right in the center of it all—award-winning restaurants, boutique shopping, coffee shops, museums, and the iconic Winter Park boat tour are all just steps away. Situated on the third floor of Building 6 with convenient elevator access, this light-filled unit offers a surprisingly flexible layout. The current owner has creatively configured the space with separate living and dining areas, while the enclosed porch serves as a bedroom. The updated kitchen features decorative tile flooring, stainless steel appliances, and solid wood cabinetry. Sliding glass doors lead to a bonus room that can easily function as a home office, guest space, workout room, or additional living area. The bathroom includes a single vanity and tub/shower combination, and you'll appreciate the abundance of storage throughout the unit. One of the biggest advantages of this property is the peace of mind that comes with a monthly HOA fee that covers nearly everything—including electric, water, sewer, trash, building insurance, landscaping, pool maintenance, and on-site management. . Whispering Waters recently passed its structural integrity inspection and reserve study with excellent results, reflecting the care and quality of this well-managed community. Residents also enjoy access to beautiful Lake Osceola, where you can launch a kayak, relax by the water, or take in breathtaking sunset views. Whether you're looking for a full-time residence or a seasonal retreat this condo offers an unbeatable Winter Park location and true lock-and-leave convenience.

311 E Morse Boulevard Unit 6-12, Winter Park

$1,770,000

Nestled along one of Winter Park's picturesque brick streets, this beautifully appointed four-bedroom, three-and-one-half-bath residence combines timeless charm with modern luxury in an exceptional location. Thoughtfully designed with an open-concept floor plan, the home offers seamless everyday living and effortless entertaining. At the heart of the home is the beautifully updated chef's kitchen overlooking the spacious living room. Premium Thermador appliances include an impressive eight-burner range featuring six gas burners and two induction burners, a separate steam oven, a built-in microwave and a three-tower refrigeration system with refrigerator, freezer and wine refrigeration. A generous breakfast nook provides abundant seating for casual dining, while the adjacent formal dining room offers versatility and is currently utilized as a private home office. The inviting living room is filled with natural light and features French doors that open to the covered lanai, creating an ideal indoor-outdoor living experience. The first-floor primary suite serves as a peaceful retreat with a spacious walk-in closet, two sets of blackout window treatments, a luxurious spa-inspired bath featuring a glass-enclosed shower and separate soaking tub and private access to the lanai and pool area. Completing the first floor are a convenient built-in workspace, a separate laundry room and a stylish powder bath. A graceful staircase leads to the second level, where you'll find three additional bedrooms, including one with an ensuite bath, along with a generous family room that provides the perfect gathering space for family and guests. Expansive windows throughout the home fill every room with abundant natural light, creating a bright and welcoming atmosphere. Outside, the covered lanai features remote-controlled retractable screens, including an integrated pet door, allowing the space to be fully enclosed for year-round enjoyment. The sparkling saltwater pool with a tranquil waterfall feature is surrounded by a beautifully landscaped, fully fenced backyard, offering exceptional privacy and a true backyard oasis. Additional features include LeafGuard-protected rain gutters, new exterior paint completed in July 2026 and a spacious two-car garage. Ideally located, this exceptional home is just an easy bike ride to the renowned boutiques, restaurants, coffee shops and Central Park along Park Avenue, as well as the popular weekly Winter Park Farmers' Market. Offering luxurious finishes, thoughtful design and an unbeatable location, this is a wonderful opportunity to enjoy the very best of Winter Park living.

4 Beds ⋅ 4 Baths ⋅ Temple Estates SubDv. ⋅ 32789 Zip Code

Nestled along one of Winter Park's picturesque brick streets, this beautifully appointed four-bedroom, three-and-one-half-bath residence combines timeless charm with modern luxury in an exceptional location. Thoughtfully designed with an open-concept floor plan, the home offers seamless everyday living and effortless entertaining. At the heart of the home is the beautifully updated chef's kitchen overlooking the spacious living room. Premium Thermador appliances include an impressive eight-burner range featuring six gas burners and two induction burners, a separate steam oven, a built-in microwave and a three-tower refrigeration system with refrigerator, freezer and wine refrigeration. A generous breakfast nook provides abundant seating for casual dining, while the adjacent formal dining room offers versatility and is currently utilized as a private home office. The inviting living room is filled with natural light and features French doors that open to the covered lanai, creating an ideal indoor-outdoor living experience. The first-floor primary suite serves as a peaceful retreat with a spacious walk-in closet, two sets of blackout window treatments, a luxurious spa-inspired bath featuring a glass-enclosed shower and separate soaking tub and private access to the lanai and pool area. Completing the first floor are a convenient built-in workspace, a separate laundry room and a stylish powder bath. A graceful staircase leads to the second level, where you'll find three additional bedrooms, including one with an ensuite bath, along with a generous family room that provides the perfect gathering space for family and guests. Expansive windows throughout the home fill every room with abundant natural light, creating a bright and welcoming atmosphere. Outside, the covered lanai features remote-controlled retractable screens, including an integrated pet door, allowing the space to be fully enclosed for year-round enjoyment. The sparkling saltwater pool with a tranquil waterfall feature is surrounded by a beautifully landscaped, fully fenced backyard, offering exceptional privacy and a true backyard oasis. Additional features include LeafGuard-protected rain gutters, new exterior paint completed in July 2026 and a spacious two-car garage. Ideally located, this exceptional home is just an easy bike ride to the renowned boutiques, restaurants, coffee shops and Central Park along Park Avenue, as well as the popular weekly Winter Park Farmers' Market. Offering luxurious finishes, thoughtful design and an unbeatable location, this is a wonderful opportunity to enjoy the very best of Winter Park living.

1230 Sunset Drive, Winter Park

$1,830,000

Set along the brick-lined streets of Charmont, one of Winter Park’s most coveted and established neighborhoods, 1661 Laurel Road presents a rare opportunity to own a home in an exceptional location just three houses from Lake Virginia. From the front yard, enjoy beautiful lake views and the timeless character of a neighborhood defined by mature trees, gracious homes, and a true sense of place. The current owners have cherished this property since 1972, and after more than five decades, the home is ready for its next chapter. Situated on an impressive 0.43-acre corner lot (18,802 square feet), the property offers flexibility that is increasingly difficult to find in Winter Park. The existing home can be thoughtfully remodeled and the floor plan reimagined while preserving the architectural charm and character that make the property special. Or, for those looking to create something entirely their own, the generous lot offers the potential to build a new home in one of Winter Park’s most desirable settings. Inside, a welcoming foyer introduces a floor plan filled with opportunity. To the right, the grand living room features abundant windows and natural light, beautiful proportions, and a wood-burning fireplace, with the space extending into a bright sunroom overlooking the grounds. A hallway off the living room leads to two bedrooms, each with its own ensuite bathroom. To the left of the foyer, a third bedroom offers a dedicated bathroom and walk-in closet. Straight ahead, the dining room features charming corner cabinetry and leads into the existing kitchen. Beyond the dining room, an additional sunroom and sitting area presents one of the home's many opportunities for transformation. Envision opening this space to create a more expansive kitchen with room for a built-in breakfast banquette, coffee bar, and functional drop zone—a gathering space designed around the way today's families live while retaining the home's original charm. A breezeway connects the main house to the two-car garage, while the space above offers a separate one-bedroom, one-bath apartment. Ideal for visiting guests, a private playroom or teen retreat, an office, or potential rental income, this additional living space adds another layer of flexibility to the property. Additional features include an irrigation well and 2018 HVAC system. Beyond the property itself, the location is what makes 1661 Laurel Road truly special. Enjoy Park Avenue, where Winter Park's beloved restaurants, boutiques, galleries, cafés, and cultural institutions create one of Central Florida's most distinctive lifestyles. Rollins College, Hannibal Square, Central Park, Mead Botanical Garden, and the Winter Park Chain of Lakes are all close by, while the neighborhood's tree-canopied streets offer a peaceful retreat just minutes from the energy of downtown. Zoned for Audubon Park K-8 and Winter Park High School, this is an opportunity to put down roots in one of Winter Park's most sought-after locations. Whether you envision restoring and reimagining the existing home or creating a new residence from the ground up, the possibilities at 1661 Laurel Road are truly exceptional. Some properties are defined by their finishes; others are defined by their location, land, history, and potential. This one offers all four.

3 Beds ⋅ 3 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Set along the brick-lined streets of Charmont, one of Winter Park’s most coveted and established neighborhoods, 1661 Laurel Road presents a rare opportunity to own a home in an exceptional location just three houses from Lake Virginia. From the front yard, enjoy beautiful lake views and the timeless character of a neighborhood defined by mature trees, gracious homes, and a true sense of place. The current owners have cherished this property since 1972, and after more than five decades, the home is ready for its next chapter. Situated on an impressive 0.43-acre corner lot (18,802 square feet), the property offers flexibility that is increasingly difficult to find in Winter Park. The existing home can be thoughtfully remodeled and the floor plan reimagined while preserving the architectural charm and character that make the property special. Or, for those looking to create something entirely their own, the generous lot offers the potential to build a new home in one of Winter Park’s most desirable settings. Inside, a welcoming foyer introduces a floor plan filled with opportunity. To the right, the grand living room features abundant windows and natural light, beautiful proportions, and a wood-burning fireplace, with the space extending into a bright sunroom overlooking the grounds. A hallway off the living room leads to two bedrooms, each with its own ensuite bathroom. To the left of the foyer, a third bedroom offers a dedicated bathroom and walk-in closet. Straight ahead, the dining room features charming corner cabinetry and leads into the existing kitchen. Beyond the dining room, an additional sunroom and sitting area presents one of the home's many opportunities for transformation. Envision opening this space to create a more expansive kitchen with room for a built-in breakfast banquette, coffee bar, and functional drop zone—a gathering space designed around the way today's families live while retaining the home's original charm. A breezeway connects the main house to the two-car garage, while the space above offers a separate one-bedroom, one-bath apartment. Ideal for visiting guests, a private playroom or teen retreat, an office, or potential rental income, this additional living space adds another layer of flexibility to the property. Additional features include an irrigation well and 2018 HVAC system. Beyond the property itself, the location is what makes 1661 Laurel Road truly special. Enjoy Park Avenue, where Winter Park's beloved restaurants, boutiques, galleries, cafés, and cultural institutions create one of Central Florida's most distinctive lifestyles. Rollins College, Hannibal Square, Central Park, Mead Botanical Garden, and the Winter Park Chain of Lakes are all close by, while the neighborhood's tree-canopied streets offer a peaceful retreat just minutes from the energy of downtown. Zoned for Audubon Park K-8 and Winter Park High School, this is an opportunity to put down roots in one of Winter Park's most sought-after locations. Whether you envision restoring and reimagining the existing home or creating a new residence from the ground up, the possibilities at 1661 Laurel Road are truly exceptional. Some properties are defined by their finishes; others are defined by their location, land, history, and potential. This one offers all four.

1661 Laurel Road, Winter Park

$700,000

Stop the car! Develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased simultaneously, for a total of 75x200 or 15,000sq/ft. Next to the proposed Winter Park Commons project, walk to Winter Park Village, Hannibal Square, WP9 and Park Ave for top shopping, dining and entertainment. Don’t miss this unique opportunity! PROPERTY SOLD AS-IS. VALUE IS IN THE LAND. NO REPAIRS.

4 Beds ⋅ 2 Baths ⋅ Capens Add SubDv. ⋅ 32789 Zip Code

Stop the car! Develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased simultaneously, for a total of 75x200 or 15,000sq/ft. Next to the proposed Winter Park Commons project, walk to Winter Park Village, Hannibal Square, WP9 and Park Ave for top shopping, dining and entertainment. Don’t miss this unique opportunity! PROPERTY SOLD AS-IS. VALUE IS IN THE LAND. NO REPAIRS.

770 W Webster Avenue, Winter Park

$135,000

Vacant! Great location! Must See! New paintinf interior, and new carpet. The best area at Winter Park, close to major shoppiing center,

3 Beds ⋅ 2 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

Vacant! Great location! Must See! New paintinf interior, and new carpet. The best area at Winter Park, close to major shoppiing center,

1695 Lee Road Unit A101, Winter Park

$4,000,000

Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winning contemporary estate is a masterclass in modern design. Tucked away on a prestigious cul-de-sac between Lake Osceola and the iconic Alfond Inn, the residence offers unparalleled privacy just two blocks from Park Avenue's world-class amenities. A striking entryway with 10-foot mahogany doors reveals a secluded courtyard oasis, featuring a sparkling pool framed by lush Signature landscaping. Inside, expansive living spaces with soaring 14-foot ceilings and a dramatic 40-foot gallery wall flow seamlessly to the outdoors, creating an effortless connection between interior elegance and open-air entertaining. The sleek, state-of-the-art kitchen is curated with premium Monogram, JennAir, and Gaggenau appliances, complemented by a sophisticated wet bar and an intimate media lounge. Ascend the floating staircase or private elevator to the primary sanctuary, which exclusively commands the entire second level. This lavish retreat features a spa-inspired bath with a smart-controlled shower, an oversized marble vanity, and three private terraces. The estate is further elevated by a first-floor guest suite, an executive office, a fitness studio with an en-suite steam shower, and a versatile poolside casita. Integrated smart home technology, automatic Lutron shades, whole-house generator and a three car garage provide ultimate modern convenience. Every element of this residence reflects intentional design, innovation, and timeless elegance, embodying the pinnacle of world-class Winter Park living.

4 Beds ⋅ 6 Baths ⋅ Alexander Place SubDv. ⋅ 32789 Zip Code

Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winning contemporary estate is a masterclass in modern design. Tucked away on a prestigious cul-de-sac between Lake Osceola and the iconic Alfond Inn, the residence offers unparalleled privacy just two blocks from Park Avenue's world-class amenities. A striking entryway with 10-foot mahogany doors reveals a secluded courtyard oasis, featuring a sparkling pool framed by lush Signature landscaping. Inside, expansive living spaces with soaring 14-foot ceilings and a dramatic 40-foot gallery wall flow seamlessly to the outdoors, creating an effortless connection between interior elegance and open-air entertaining. The sleek, state-of-the-art kitchen is curated with premium Monogram, JennAir, and Gaggenau appliances, complemented by a sophisticated wet bar and an intimate media lounge. Ascend the floating staircase or private elevator to the primary sanctuary, which exclusively commands the entire second level. This lavish retreat features a spa-inspired bath with a smart-controlled shower, an oversized marble vanity, and three private terraces. The estate is further elevated by a first-floor guest suite, an executive office, a fitness studio with an en-suite steam shower, and a versatile poolside casita. Integrated smart home technology, automatic Lutron shades, whole-house generator and a three car garage provide ultimate modern convenience. Every element of this residence reflects intentional design, innovation, and timeless elegance, embodying the pinnacle of world-class Winter Park living.

229 Alexander Place, Winter Park

$105,000

Welcome to this charming first-floor 3-bedroom, 2-bath condominium located in the beautiful city of Winter Park! Featuring laminate flooring throughout the main living areas, this inviting home offers an open-concept layout with a combined living and dining room that overlooks the kitchen, creating the perfect space for everyday living and entertaining. Each bedroom is equipped with a ceiling fan for added comfort, while the private rear patio provides a peaceful outdoor retreat complete with a bench—ideal for relaxing and enjoying Florida's beautiful weather. Whether you're searching for a primary residence, a seasonal getaway, or an investment opportunity, this condo offers exceptional value. HOA dues include pest control, basic cable, basic internet, exterior maintenance, and additional storage, providing convenience and peace of mind. Residents also enjoy access to community amenities including a swimming pool, playground, and clubhouse, all in a desirable Winter Park location close to shopping, dining, parks, and major roadways. Don't miss the opportunity to make this wonderful property your own!

3 Beds ⋅ 2 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

Welcome to this charming first-floor 3-bedroom, 2-bath condominium located in the beautiful city of Winter Park! Featuring laminate flooring throughout the main living areas, this inviting home offers an open-concept layout with a combined living and dining room that overlooks the kitchen, creating the perfect space for everyday living and entertaining. Each bedroom is equipped with a ceiling fan for added comfort, while the private rear patio provides a peaceful outdoor retreat complete with a bench—ideal for relaxing and enjoying Florida's beautiful weather. Whether you're searching for a primary residence, a seasonal getaway, or an investment opportunity, this condo offers exceptional value. HOA dues include pest control, basic cable, basic internet, exterior maintenance, and additional storage, providing convenience and peace of mind. Residents also enjoy access to community amenities including a swimming pool, playground, and clubhouse, all in a desirable Winter Park location close to shopping, dining, parks, and major roadways. Don't miss the opportunity to make this wonderful property your own!

1695 Lee Road Unit A116, Winter Park

$510,000

Charming, Fully Renovated Pool Home in Sought-After Winter Park. Welcome to this beautifully updated pool home, ideally located in desirable Winter Park—just minutes from premier shopping, dining, and entertainment, with easy access to major roadways for a seamless commute. From the moment you step inside, you’re greeted by a warm, modern aesthetic that blends comfort with style. To the right, a spacious step-down living room offers abundant natural light and lovely views of the front yard. To the left, the formal dining room flows effortlessly into the heart of the home—a stunning, fully renovated kitchen and inviting family room overlooking the private pool and patio. The kitchen is designed to impress, featuring solid wood cabinetry, stainless steel appliances, sleek modern lighting, ample counter space, and a center island perfect for gathering. The adjoining family room is anchored by a stylish electric fireplace, creating a cozy ambiance while offering serene views of the outdoor living area. This home features a desirable split-bedroom floor plan, providing privacy and flexibility. The primary suite is tucked away on one side, while two additional bedrooms and a full bathroom are located on the opposite wing—ideal for family or guests. Extensive upgrades provide peace of mind and modern appeal, including a newer roof (2021), a newer AC (2019) fully renovated kitchen and bathrooms, 5-inch baseboards, knockdown ceiling texture, textured walls, luxury vinyl plank flooring throughout, fresh interior and exterior paint, and updated electrical and plumbing fixtures. Step outside to your private oasis—a fully fenced backyard with a screened-in pool enclosure and lanai, perfect for relaxing or entertaining year-round in true Florida style. This move-in-ready gem truly has it all. Don’t miss your opportunity—schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code

Charming, Fully Renovated Pool Home in Sought-After Winter Park. Welcome to this beautifully updated pool home, ideally located in desirable Winter Park—just minutes from premier shopping, dining, and entertainment, with easy access to major roadways for a seamless commute. From the moment you step inside, you’re greeted by a warm, modern aesthetic that blends comfort with style. To the right, a spacious step-down living room offers abundant natural light and lovely views of the front yard. To the left, the formal dining room flows effortlessly into the heart of the home—a stunning, fully renovated kitchen and inviting family room overlooking the private pool and patio. The kitchen is designed to impress, featuring solid wood cabinetry, stainless steel appliances, sleek modern lighting, ample counter space, and a center island perfect for gathering. The adjoining family room is anchored by a stylish electric fireplace, creating a cozy ambiance while offering serene views of the outdoor living area. This home features a desirable split-bedroom floor plan, providing privacy and flexibility. The primary suite is tucked away on one side, while two additional bedrooms and a full bathroom are located on the opposite wing—ideal for family or guests. Extensive upgrades provide peace of mind and modern appeal, including a newer roof (2021), a newer AC (2019) fully renovated kitchen and bathrooms, 5-inch baseboards, knockdown ceiling texture, textured walls, luxury vinyl plank flooring throughout, fresh interior and exterior paint, and updated electrical and plumbing fixtures. Step outside to your private oasis—a fully fenced backyard with a screened-in pool enclosure and lanai, perfect for relaxing or entertaining year-round in true Florida style. This move-in-ready gem truly has it all. Don’t miss your opportunity—schedule your private showing today!

1438 Tierra Circle, Winter Park

$365,000

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully maintained and updated over time, this property combines functional living with key improvements that add long-term value and peace of mind. Inside, the open floorplan creates a bright, connected flow across the main living areas—ideal for both everyday living and entertaining. The separate family room adds valuable versatility, perfect as a media room, home office, playroom, or relaxed second living area. The bedroom layout is practical and comfortable, providing a solid foundation for personal touches and customization. Recent updates enhance both the appeal and functionality of the home, including a roof installed in 2020, HVAC system replaced in 2019, a new garage door with opener (2019), and fresh exterior paint completed in 2024. The bathroom has been refreshed with a new sink, toilet, and tub surround in 2025, offering a clean, updated feel. The outdoor spaces further elevate the property. An enclosed front porch provides a welcoming spot to enjoy a quiet morning or unwind in the evening, while the open rear patio is perfect for grilling, dining, or relaxing outdoors. The private backyard offers plenty of space to expand your vision, with strong potential to create a personalized outdoor retreat. With its solid layout, meaningful updates, and room to grow, this home presents an excellent opportunity for buyers looking to settle into a well-located property while continuing to enhance it over time. Situated in desirable Winter Park, the home benefits from a location known for its established charm, tree-lined streets, and convenient access to shopping, dining, parks, and everyday essentials, making it one of Central Florida’s most sought-after communities.

2 Beds ⋅ 1 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully maintained and updated over time, this property combines functional living with key improvements that add long-term value and peace of mind. Inside, the open floorplan creates a bright, connected flow across the main living areas—ideal for both everyday living and entertaining. The separate family room adds valuable versatility, perfect as a media room, home office, playroom, or relaxed second living area. The bedroom layout is practical and comfortable, providing a solid foundation for personal touches and customization. Recent updates enhance both the appeal and functionality of the home, including a roof installed in 2020, HVAC system replaced in 2019, a new garage door with opener (2019), and fresh exterior paint completed in 2024. The bathroom has been refreshed with a new sink, toilet, and tub surround in 2025, offering a clean, updated feel. The outdoor spaces further elevate the property. An enclosed front porch provides a welcoming spot to enjoy a quiet morning or unwind in the evening, while the open rear patio is perfect for grilling, dining, or relaxing outdoors. The private backyard offers plenty of space to expand your vision, with strong potential to create a personalized outdoor retreat. With its solid layout, meaningful updates, and room to grow, this home presents an excellent opportunity for buyers looking to settle into a well-located property while continuing to enhance it over time. Situated in desirable Winter Park, the home benefits from a location known for its established charm, tree-lined streets, and convenient access to shopping, dining, parks, and everyday essentials, making it one of Central Florida’s most sought-after communities.

440 Cambridge Boulevard, Winter Park

$4,650,000

Privately nestled on 1.32 acres (1.1+ acres HIGH & DRY) along the tranquil shores of Lake Temple, this remarkable residence is a true compound where architecture, craftsmanship, and nature exist in perfect balance. Completed in 2019 by Gallimore Homes and enhanced with more than $300K in upgrades, this home was designed to feel secluded and private while serving as the ultimate destination for entertaining. This unique property offers a 4,060+ SF main residence (4 beds / 3.5 baths plus bonus room for a future 5th bedroom), a detached 480+ SF guest house (1 bed / 1 bath), and resort-style outdoor living overlooking peaceful water views and a rolling backyard. Designed for exceptional privacy, the home is positioned well back from the street and buffered by mature landscaping, a private courtyard wall with a security gate, and hurricane-impact windows and doors throughout. Additional highlights include an oversized three-car garage, parking for 15+ vehicles, and space to park a boat or RV next to the conservation area. Inside, soaring ceilings and premium finishes create an immediate sense of warmth and sophistication. Ten-foot-tall EuroWall folding glass doors span 15 feet across the great room, seamlessly blending indoor and outdoor living while framing beautiful backyard and water views. The chef's kitchen showcases professional-grade Sub-Zero and Wolf appliances, an oversized gathering island with prep sink, ice maker, waterfall countertops, a 48-inch Wolf six-burner dual-fuel range, dry bar with refrigerated drawers, and a spacious walk-in pantry. The open-concept design flows effortlessly into the great room and dining area, making everyday living and entertaining equally inviting. The split-bedroom floor plan offers exceptional privacy, highlighted by a spacious first-floor primary suite with 2 walk-in closets (totaling 175+ SF) and a spa-inspired bath. The first floor also includes a guest suite, two additional bedrooms with a Jack-and-Jill bath, and a powder/pool bath with access to the lania. Upstairs, the bonus room provides flexibility for a media room, game room, home office, and pre-plumed for a bath and kitchenette for a future 5th bedroom. Equally impressive is the detached guest house, complete with its own covered front porch, full kitchen, living room, bedroom, full bath, and beautiful backyard views…ideal for multigenerational living, extended guests, a private office, or long-term visitors. The covered lanai was designed for year-round outdoor living with three Phantom Screens spanning nearly 45 feet, an authentic Argentine wood-fired grill, and a built-in wet bar. The heated saltwater infinity-edge pool features a sun shelf, LED lighting, and a composite wood sun deck overlooking the water. The expansive lawn gently slopes to the shoreline beneath a magnificent 100+ year-old oak tree, enhanced by mature landscaping and landscape lighting that creates an unforgettable setting for intimate evenings and large-scale gatherings too. Located less than three miles from Interlachen Country Club and a few blocks from the Winter Park Racquet Club, this property offers a rare combination of privacy, flexibility, and estate-style living on more than an acre of waterfront in Winter Park.

5 Beds ⋅ 5 Baths ⋅ Lake Maitland SubDv. ⋅ 32789 Zip Code

Privately nestled on 1.32 acres (1.1+ acres HIGH & DRY) along the tranquil shores of Lake Temple, this remarkable residence is a true compound where architecture, craftsmanship, and nature exist in perfect balance. Completed in 2019 by Gallimore Homes and enhanced with more than $300K in upgrades, this home was designed to feel secluded and private while serving as the ultimate destination for entertaining. This unique property offers a 4,060+ SF main residence (4 beds / 3.5 baths plus bonus room for a future 5th bedroom), a detached 480+ SF guest house (1 bed / 1 bath), and resort-style outdoor living overlooking peaceful water views and a rolling backyard. Designed for exceptional privacy, the home is positioned well back from the street and buffered by mature landscaping, a private courtyard wall with a security gate, and hurricane-impact windows and doors throughout. Additional highlights include an oversized three-car garage, parking for 15+ vehicles, and space to park a boat or RV next to the conservation area. Inside, soaring ceilings and premium finishes create an immediate sense of warmth and sophistication. Ten-foot-tall EuroWall folding glass doors span 15 feet across the great room, seamlessly blending indoor and outdoor living while framing beautiful backyard and water views. The chef's kitchen showcases professional-grade Sub-Zero and Wolf appliances, an oversized gathering island with prep sink, ice maker, waterfall countertops, a 48-inch Wolf six-burner dual-fuel range, dry bar with refrigerated drawers, and a spacious walk-in pantry. The open-concept design flows effortlessly into the great room and dining area, making everyday living and entertaining equally inviting. The split-bedroom floor plan offers exceptional privacy, highlighted by a spacious first-floor primary suite with 2 walk-in closets (totaling 175+ SF) and a spa-inspired bath. The first floor also includes a guest suite, two additional bedrooms with a Jack-and-Jill bath, and a powder/pool bath with access to the lania. Upstairs, the bonus room provides flexibility for a media room, game room, home office, and pre-plumed for a bath and kitchenette for a future 5th bedroom. Equally impressive is the detached guest house, complete with its own covered front porch, full kitchen, living room, bedroom, full bath, and beautiful backyard views…ideal for multigenerational living, extended guests, a private office, or long-term visitors. The covered lanai was designed for year-round outdoor living with three Phantom Screens spanning nearly 45 feet, an authentic Argentine wood-fired grill, and a built-in wet bar. The heated saltwater infinity-edge pool features a sun shelf, LED lighting, and a composite wood sun deck overlooking the water. The expansive lawn gently slopes to the shoreline beneath a magnificent 100+ year-old oak tree, enhanced by mature landscaping and landscape lighting that creates an unforgettable setting for intimate evenings and large-scale gatherings too. Located less than three miles from Interlachen Country Club and a few blocks from the Winter Park Racquet Club, this property offers a rare combination of privacy, flexibility, and estate-style living on more than an acre of waterfront in Winter Park.

2525 Temple Drive, Winter Park

$490,000

Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.

3 Beds ⋅ 3 Baths ⋅ Fairshores Place SubDv. ⋅ 32789 Zip Code

Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.

2803 Riddle Drive, Winter Park

$920,000

Curated with intention and finished without compromise, 1120 Wisconsin Avenue is a rare opportunity to own a bespoke Winter Park residence where elevated design meets effortless everyday living. Every detail of this 2,213-square-foot, three-bedroom, three-and-a-half-bath home has been thoughtfully considered — from the custom Pella® multi-point entry door that welcomes you into a light-filled, open-concept gathering room, to the chef's kitchen anchored by a dramatic waterfall island and ZLINE commercial-style gas range with soft-close cabinetry and curated high-end appliances throughout. A private courtyard entry sets a serene tone before you've even stepped inside. The seamless indoor-outdoor connection continues through Pella® wood-clad sliding glass doors to a covered BBQ kitchen lanai — your own tranquil outdoor retreat. The primary suite is a true sanctuary: a generous walk-in closet, a sitting area, linen storage, and a spa-caliber bathroom with a double-sink vanity and oversized walk-in shower. Upstairs, two spacious en-suite bedrooms and a versatile loft with built-in storage offer flexibility for guests, family, or a refined home office. Finished with stunning hardwood floors, soaring ceilings, custom window treatments, spray foam insulation, and dual-zone climate control, this home is as quietly practical as it is undeniably beautiful. Whether you're entertaining or simply unwinding, 1120 Wisconsin Avenue offers the ease and elegance of a true lock-and-leave lifestyle in one of Winter Park's most sought-after neighborhoods.

3 Beds ⋅ 4 Baths ⋅ Henkel Add SubDv. ⋅ 32789 Zip Code

Curated with intention and finished without compromise, 1120 Wisconsin Avenue is a rare opportunity to own a bespoke Winter Park residence where elevated design meets effortless everyday living. Every detail of this 2,213-square-foot, three-bedroom, three-and-a-half-bath home has been thoughtfully considered — from the custom Pella® multi-point entry door that welcomes you into a light-filled, open-concept gathering room, to the chef's kitchen anchored by a dramatic waterfall island and ZLINE commercial-style gas range with soft-close cabinetry and curated high-end appliances throughout. A private courtyard entry sets a serene tone before you've even stepped inside. The seamless indoor-outdoor connection continues through Pella® wood-clad sliding glass doors to a covered BBQ kitchen lanai — your own tranquil outdoor retreat. The primary suite is a true sanctuary: a generous walk-in closet, a sitting area, linen storage, and a spa-caliber bathroom with a double-sink vanity and oversized walk-in shower. Upstairs, two spacious en-suite bedrooms and a versatile loft with built-in storage offer flexibility for guests, family, or a refined home office. Finished with stunning hardwood floors, soaring ceilings, custom window treatments, spray foam insulation, and dual-zone climate control, this home is as quietly practical as it is undeniably beautiful. Whether you're entertaining or simply unwinding, 1120 Wisconsin Avenue offers the ease and elegance of a true lock-and-leave lifestyle in one of Winter Park's most sought-after neighborhoods.

1120 Wisconsin Avenue, Winter Park

$82,000

This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and dryer. Assigned parkingspace. Community features swimming pool, tennis court and playground. Rent price includes use of the amenities, free basic cable TV, free internet, and pest control.

1 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and dryer. Assigned parkingspace. Community features swimming pool, tennis court and playground. Rent price includes use of the amenities, free basic cable TV, free internet, and pest control.

1695 Lee Road Unit B210, Winter Park

$5,600,000

Have you been waiting for a home on the Winter Park Chain of Lakes? Here is your chance!! Discover an unparalleled living experience on the prestigious Winter Park Chain of Lakes! Nestled on highly sought-after Alabama Drive, this exquisite two-story residence invites you to embrace a lifestyle of comfort and elegance. With 3,680 square feet of meticulously designed space, this home offers five bedrooms and three and a half baths, including a charming guest suite above the garage complete with a private bath and kitchenette – perfect for visitors or extended family. A covered front porch and a welcoming circular driveway, framed by mature trees, greet you with incredible, sweeping views of Lake Maitland, promising serene mornings and breathtaking sunsets. Step inside and feel instantly at home as original hardwood floors guide you through a spacious foyer, where a grand staircase sets a tone of refined sophistication. The heart of this home, the kitchen, is a captivating blend of functionality and style, ready for culinary adventures. It features a generous central island with a stovetop, complemented by crisp white countertops, warm wooden cabinetry, and stainless steel appliances. A built-in oven, microwave, and a charming terracotta wine rack enhance the culinary experience. Spacious, open and roomy. Thoughtfully designed living spaces beckon, perfect for grand entertaining or cozy, intimate gatherings. An elegant living room offers a warm ambiance with a fireplace and captivating lake views that will enchant you all day long! Another expansive living area off the kitchen showcases exposed wooden beams and rich brick tile flooring, exuding rustic charm. Large windows throughout the front of the home frame picturesque lake views, creating a serene backdrop for daily life. With a total of four fireplaces—three gas and one wood-burning—you'll find inviting focal points throughout. A sunroom, bathed in natural light from its expansive windows and finished with cheerful brick tile flooring, provides a tranquil retreat, further enhanced by the endless windows. Enjoy casual meals in the eat-in dining room, or host memorable dinners in the formal dining room, which boasts amazing custom shelving, detailed molding, a beautiful gas fireplace, original hardwood floors and of course view of the lake. The primary suite is a luxurious sanctuary, generously sized and anchored by stunning views of Lake Maitland and a cozy fireplace, creating an inviting sitting area within the bedroom itself. The spacious primary bathroom offers a double vanity, an updated shower, and a separate soaking tub for ultimate relaxation. In the main home, you'll find three additional bedrooms, each offering spacious comfort and ample storage. A truly distinctive feature of this property is the private guest suite, thoughtfully designed with one bedroom, one bath, a kitchenette, and a cozy wood-burning stove, offering comfort and privacy. This versatile space serves as the home's fifth bedroom, providing a wonderful haven for guests. Beyond the inviting interior, the property extends its allure to the outdoors. A private wooden dock extends onto Lake Maitland, part of the prestigious Winter Park Chain of Lakes, offering direct access to shimmering waters and endless aquatic adventures. A boathouse further enhances lakeside enjoyment. A charming patio area provides an ideal setting for outdoor leisure and entertaining amidst the verdant surroundings. Welcome home!

5 Beds ⋅ 4 Baths ⋅ Alabama Oaks SubDv. ⋅ 32789 Zip Code

Have you been waiting for a home on the Winter Park Chain of Lakes? Here is your chance!! Discover an unparalleled living experience on the prestigious Winter Park Chain of Lakes! Nestled on highly sought-after Alabama Drive, this exquisite two-story residence invites you to embrace a lifestyle of comfort and elegance. With 3,680 square feet of meticulously designed space, this home offers five bedrooms and three and a half baths, including a charming guest suite above the garage complete with a private bath and kitchenette – perfect for visitors or extended family. A covered front porch and a welcoming circular driveway, framed by mature trees, greet you with incredible, sweeping views of Lake Maitland, promising serene mornings and breathtaking sunsets. Step inside and feel instantly at home as original hardwood floors guide you through a spacious foyer, where a grand staircase sets a tone of refined sophistication. The heart of this home, the kitchen, is a captivating blend of functionality and style, ready for culinary adventures. It features a generous central island with a stovetop, complemented by crisp white countertops, warm wooden cabinetry, and stainless steel appliances. A built-in oven, microwave, and a charming terracotta wine rack enhance the culinary experience. Spacious, open and roomy. Thoughtfully designed living spaces beckon, perfect for grand entertaining or cozy, intimate gatherings. An elegant living room offers a warm ambiance with a fireplace and captivating lake views that will enchant you all day long! Another expansive living area off the kitchen showcases exposed wooden beams and rich brick tile flooring, exuding rustic charm. Large windows throughout the front of the home frame picturesque lake views, creating a serene backdrop for daily life. With a total of four fireplaces—three gas and one wood-burning—you'll find inviting focal points throughout. A sunroom, bathed in natural light from its expansive windows and finished with cheerful brick tile flooring, provides a tranquil retreat, further enhanced by the endless windows. Enjoy casual meals in the eat-in dining room, or host memorable dinners in the formal dining room, which boasts amazing custom shelving, detailed molding, a beautiful gas fireplace, original hardwood floors and of course view of the lake. The primary suite is a luxurious sanctuary, generously sized and anchored by stunning views of Lake Maitland and a cozy fireplace, creating an inviting sitting area within the bedroom itself. The spacious primary bathroom offers a double vanity, an updated shower, and a separate soaking tub for ultimate relaxation. In the main home, you'll find three additional bedrooms, each offering spacious comfort and ample storage. A truly distinctive feature of this property is the private guest suite, thoughtfully designed with one bedroom, one bath, a kitchenette, and a cozy wood-burning stove, offering comfort and privacy. This versatile space serves as the home's fifth bedroom, providing a wonderful haven for guests. Beyond the inviting interior, the property extends its allure to the outdoors. A private wooden dock extends onto Lake Maitland, part of the prestigious Winter Park Chain of Lakes, offering direct access to shimmering waters and endless aquatic adventures. A boathouse further enhances lakeside enjoyment. A charming patio area provides an ideal setting for outdoor leisure and entertaining amidst the verdant surroundings. Welcome home!

1530 Alabama Drive, Winter Park

$990,000

Incredibly charming Craftsman style home that's been artfully renovated and is located in the heart of Winter Park’s sought-after College Quarter, just footsteps from Rollins, restaurants, and Park Avenue! The owners thoughtfully renovated this three-bedroom, two-bath bungalow in 2022/2023. The home underwent a comprehensive transformation with all major systems and components fully updated or replaced, including the electrical, plumbing, HVAC, roof, siding, walls, spray foam insulation, appliances and more, offering a turnkey residence where modern functionality complements timeless character. Inside, gorgeous "antique heart of pine" wood floors lend warmth and character, while abundant windows/glass doors fill the home with natural light. The welcoming living room features a vaulted ceiling and French doors opening to an expansive deck and private, fenced backyard, creating an effortless connection between indoor and outdoor living. The beautiful new classic kitchen is designed for both everyday living and entertaining, with a generous island with seating and a gas range and hood. The serene primary suite is enhanced by custom built-ins and two separate closets outfitted with thoughtfully designed organization systems, providing exceptional storage. The renovated primary bath features dual vanities and a spacious walk-in shower. Two additional bedrooms offer flexibility for guests, work or personal space, with one currently utilized as a comfortable office/den. A beautifully remodeled second bath and convenient interior laundry closet complete the well-designed floor plan. Additional storage is found in the spacious attic, which has been thoughtfully improved with added flooring for ease of access and a new pull-down ladder system, creating a highly functional area for seasonal belongings and household storage. Outside, the sunny backyard is framed by bamboo and features a detached utility shed for additional outdoor storage (note: well for irrigation system). A picturesque setting and an enviable location further distinguish this delightful residence. From here, stroll along Holt Avenue to Rollins College, enjoy the scenic Lake Virginia walking trail, or walk to Park Avenue’s acclaimed restaurants, boutique shops and sidewalk cafés. Central Park and the Winter Park Farmers’ Market are close by, as is the Winter Park 9 Golf Course. This exceptional location places the best of Winter Park within easy reach while offering the comfort, character and peace of a beautifully renewed bungalow.

3 Beds ⋅ 2 Baths ⋅ Mrs L A Dennis Sub SubDv. ⋅ 32789 Zip Code

Incredibly charming Craftsman style home that's been artfully renovated and is located in the heart of Winter Park’s sought-after College Quarter, just footsteps from Rollins, restaurants, and Park Avenue! The owners thoughtfully renovated this three-bedroom, two-bath bungalow in 2022/2023. The home underwent a comprehensive transformation with all major systems and components fully updated or replaced, including the electrical, plumbing, HVAC, roof, siding, walls, spray foam insulation, appliances and more, offering a turnkey residence where modern functionality complements timeless character. Inside, gorgeous "antique heart of pine" wood floors lend warmth and character, while abundant windows/glass doors fill the home with natural light. The welcoming living room features a vaulted ceiling and French doors opening to an expansive deck and private, fenced backyard, creating an effortless connection between indoor and outdoor living. The beautiful new classic kitchen is designed for both everyday living and entertaining, with a generous island with seating and a gas range and hood. The serene primary suite is enhanced by custom built-ins and two separate closets outfitted with thoughtfully designed organization systems, providing exceptional storage. The renovated primary bath features dual vanities and a spacious walk-in shower. Two additional bedrooms offer flexibility for guests, work or personal space, with one currently utilized as a comfortable office/den. A beautifully remodeled second bath and convenient interior laundry closet complete the well-designed floor plan. Additional storage is found in the spacious attic, which has been thoughtfully improved with added flooring for ease of access and a new pull-down ladder system, creating a highly functional area for seasonal belongings and household storage. Outside, the sunny backyard is framed by bamboo and features a detached utility shed for additional outdoor storage (note: well for irrigation system). A picturesque setting and an enviable location further distinguish this delightful residence. From here, stroll along Holt Avenue to Rollins College, enjoy the scenic Lake Virginia walking trail, or walk to Park Avenue’s acclaimed restaurants, boutique shops and sidewalk cafés. Central Park and the Winter Park Farmers’ Market are close by, as is the Winter Park 9 Golf Course. This exceptional location places the best of Winter Park within easy reach while offering the comfort, character and peace of a beautifully renewed bungalow.

393 Holt Avenue, Winter Park

$401,200

Prices like this won't last in the highly desirable historic city of Winter Park. This classic Winter Park mid-century modern home is close to the popular Central Florida YMCA, Winter Park's A+ schools, and the city's famous Park Avenue where locals and visitors gather for fine dining, boutique shopping and a full calendar of events in Central Park and other entertainment venues. This 3/2 home features a wide-open great room, an all-weather lanai and a covered backyard pavilion for at-home entertaining. The neighborhood is well established with shade trees, mature landscaping and sidewalks. Located less than 20 minutes from downtown Orlando's business center and performing arts, Magic NBA basketball, Orlando Pride and Orlando City MLS soccer, and so much more!

3 Beds ⋅ 2 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code

Prices like this won't last in the highly desirable historic city of Winter Park. This classic Winter Park mid-century modern home is close to the popular Central Florida YMCA, Winter Park's A+ schools, and the city's famous Park Avenue where locals and visitors gather for fine dining, boutique shopping and a full calendar of events in Central Park and other entertainment venues. This 3/2 home features a wide-open great room, an all-weather lanai and a covered backyard pavilion for at-home entertaining. The neighborhood is well established with shade trees, mature landscaping and sidewalks. Located less than 20 minutes from downtown Orlando's business center and performing arts, Magic NBA basketball, Orlando Pride and Orlando City MLS soccer, and so much more!

2015 Taylor Avenue, Winter Park

$320,000

Winter Park address with Seminole County taxes, and a new roof already in place from 2023. Three bedrooms, two baths, roughly 1,235 sf of living space in solid concrete block with central air. The 9,000 sf lot is fenced and shaded by mature oaks, and a 550 sf carport with workshop space. Flood Zone X, so no lender-required flood insurance. No HOA. No CDD. For an investor, the basis here pencils from day one and cosmetic updates move the rent meaningfully. For an owner-occupant, this is one of the last ways into a Winter Park address at this price. Please see attached inspection and four points report.

3 Beds ⋅ 2 Baths ⋅ Ridge High Sub SubDv. ⋅ 32792 Zip Code

Winter Park address with Seminole County taxes, and a new roof already in place from 2023. Three bedrooms, two baths, roughly 1,235 sf of living space in solid concrete block with central air. The 9,000 sf lot is fenced and shaded by mature oaks, and a 550 sf carport with workshop space. Flood Zone X, so no lender-required flood insurance. No HOA. No CDD. For an investor, the basis here pencils from day one and cosmetic updates move the rent meaningfully. For an owner-occupant, this is one of the last ways into a Winter Park address at this price. Please see attached inspection and four points report.

2313 Knoll Street, Winter Park

3373 Cedar Springs Place Unit 149, Winter Park

$165,000

LOOKING for a Beautiful LOW MAINTENANCE HOME. LOOK NO FURTHER. I INVITE YOU TO TAKE A LOOK!! This BEAUTIFUL Townhome has 2 MASTER SUITES, Perfect for Two Couples, Roommates or simply having a SPARE SUITE and is located on the Second Floor. A HALF BATH is conveniently located on the First Floor, along with the LIVING/DINING AREA, KITCHEN, DINETTE AREA AND LAUNDRY CLOSET. ENJOY THE OUTDOOR ON YOUR PRIVATE WOOD FENCED PATIO. WATER IS INCLUDED IN MONTHLY HOA DUES. NEWER VINYL FLOORING THROUGHOUT conveying a CLEANER LOOK and enables EASY MAINTENANCE, NO WORRIES ABOUT THE OCCASIONAL SPILLS just grab a damp mop and a smile. NEWLY CARPETED STAIRWAY. The pics show noticeable upgrades in the Bathrooms and areas of the KITCHEN (ALL NEW TOILETS, VANITIES, throughout the Home. FRESHLY PAINTED INTERIOR ready for occupancy. This Centralized Location is close to UCF, Orlando International Airport, Shopping, HIGHLY RATED SCHOOLS, Restaurants and more. THE AIR CONDITIONER IS 3 YEARS NEW. TWO DEDICATED PARKING SPOTS DIRECTLY IN FRONT OF THE UNIT (one comes with the unit, the second one requires a small annual fee) NEW ROOF INSTALLED IN 2023. NEWLY RESURFACED SPARKLING COMMUNITY POOL! WATER INCLUDED IN MONTHLY HOA DUES! BASK ON YOUR PRIVATE PATIO WITH YOUR FAVORITE BEVERAGE after a stressful day OR RELAX IN THE SPARKLING COMMUNITY POOL! COME HOME TO COMFORT AND SERENITY IN THIS QUIET COMMUNITY!! THIS HOME IS WAITING FOR YOU. COME INSIDE AND SEE!!

2 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 09 SubDv. ⋅ 32792 Zip Code

LOOKING for a Beautiful LOW MAINTENANCE HOME. LOOK NO FURTHER. I INVITE YOU TO TAKE A LOOK!! This BEAUTIFUL Townhome has 2 MASTER SUITES, Perfect for Two Couples, Roommates or simply having a SPARE SUITE and is located on the Second Floor. A HALF BATH is conveniently located on the First Floor, along with the LIVING/DINING AREA, KITCHEN, DINETTE AREA AND LAUNDRY CLOSET. ENJOY THE OUTDOOR ON YOUR PRIVATE WOOD FENCED PATIO. WATER IS INCLUDED IN MONTHLY HOA DUES. NEWER VINYL FLOORING THROUGHOUT conveying a CLEANER LOOK and enables EASY MAINTENANCE, NO WORRIES ABOUT THE OCCASIONAL SPILLS just grab a damp mop and a smile. NEWLY CARPETED STAIRWAY. The pics show noticeable upgrades in the Bathrooms and areas of the KITCHEN (ALL NEW TOILETS, VANITIES, throughout the Home. FRESHLY PAINTED INTERIOR ready for occupancy. This Centralized Location is close to UCF, Orlando International Airport, Shopping, HIGHLY RATED SCHOOLS, Restaurants and more. THE AIR CONDITIONER IS 3 YEARS NEW. TWO DEDICATED PARKING SPOTS DIRECTLY IN FRONT OF THE UNIT (one comes with the unit, the second one requires a small annual fee) NEW ROOF INSTALLED IN 2023. NEWLY RESURFACED SPARKLING COMMUNITY POOL! WATER INCLUDED IN MONTHLY HOA DUES! BASK ON YOUR PRIVATE PATIO WITH YOUR FAVORITE BEVERAGE after a stressful day OR RELAX IN THE SPARKLING COMMUNITY POOL! COME HOME TO COMFORT AND SERENITY IN THIS QUIET COMMUNITY!! THIS HOME IS WAITING FOR YOU. COME INSIDE AND SEE!!

3373 Cedar Springs Place Unit 149, Winter Park

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How much is your home worth?