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1825 Chilean Lane, Winter Park
$450,000
5 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully renovated pool home featuring a rare and versatile double primary suite layout! Completely renovated in 2024, this 5-bedroom, 3-bathroom home offers 1,636 square feet of stylish, thoughtfully designed living space with modern finishes throughout. Light gray wood-look plank tile flooring and recessed lighting create a bright, cohesive feel. The contemporary kitchen showcases gray shaker-style cabinetry, sleek black granite countertops, a marble-look tile backsplash with black mosaic accents, stainless steel appliances, and a breakfast bar with seating for four. The first primary suite is privately positioned away from the additional bedrooms and features an ensuite bathroom with a marble-look tiled shower, decorative mosaic accents, multiple shower heads including a rain shower, a frameless glass enclosure, and a gray vanity topped with black granite. The second primary suite provides added flexibility for multigenerational living, extended guests, or a private retreat. Step outside to enjoy your own backyard oasis, complete with an in-ground pool, screened lanai, and fully fenced, spacious backyard with plenty of green space for relaxing, entertaining, and outdoor activities. Ideally located approximately 10 minutes from the restaurants and boutiques of Park Avenue, with convenient access to UCF, Full Sail University, Rollins College, major transportation routes, shopping, and dining. Orlando International Airport is approximately 25 minutes away. With its modern renovations, dual primary suites, and inviting outdoor living space, this home offers a unique combination of comfort, flexibility, and convenience! ROOF - 2024 HVAC - 2025 PLUMBING - 2026 ELECTRICAL - 2024

1825 Chilean Lane, Winter Park
3027 Aaron Bur Avenue Unit L1, Winter Park
$169,999
2 Beds ⋅ 3 Baths ⋅ Colonies SubDv. ⋅ 32792 Zip Code
STUNNING FULLY REMODELED TWO-STORY CORNER-UNIT CONDO IN THE HEART OF WINTER PARK! GREAT OPPORTUNITY FOR HOMEOWNERS AND INVESTORS! Welcome to this beautifully renovated 2-bedroom, 2.5-bathroom, two-story corner-unit condo featuring modern finishes, gorgeous flooring, a stylish kitchen with stainless steel appliances, a BRAND-NEW A/C UNIT, and beautiful upgrades throughout! The first floor offers a spacious living area, a convenient half bathroom, and an indoor laundry closet with washer and dryer. Upstairs, you'll find two comfortable bedrooms, each with its own full bathroom, offering privacy and functionality. Enjoy the community swimming pool, ample parking, and a desirable location tucked toward the back of the community, away from the main commercial activity. LOCATION, LOCATION, LOCATION! Enjoy the convenience of nearby shopping, restaurants, cafés, and everyday essentials within walking distance! Located just minutes from Winter Park's famous Park Avenue, Rollins College, Winter Park Village, Full Sail University, beautiful parks, and Downtown Orlando, with easy access to major roadways. INVESTORS TAKE NOTICE! This move-in-ready, fully remodeled condo offers an attractive investment opportunity in a convenient Winter Park location, close to universities, employment centers, shopping, dining, and entertainment. Whether you're looking for a primary residence or an investment property, this condo offers modern upgrades, comfort, and convenience! Some photos have been virtually staged to illustrate the property's potential.

3027 Aaron Bur Avenue Unit L1, Winter Park
541 Virginia Drive, Winter Park
$5,695,000
4 Beds ⋅ 4 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code
Experience Winter Park lakefront living at 541 Virginia Drive, where timeless architecture, craftsmanship, and waterfront lifestyle come together. Set on approximately 130 feet of Lake Virginia frontage, this estate offers access to the Winter Park Chain of Lakes, a private dock with a covered electric boat lift, and grand water views toward Rollins College and historic Knowles Chapel. On a quiet Timberlane Shores cul-de-sac, this award-winning residence was built in 2008 by Farina & Sons. Recognized with an Aurora Award and Parade of Homes Grand Winner honors, the home blends historic Winter Park charm with modern luxury. Offering 4 bedrooms, 3.5 bathrooms, and 4,725 square feet of thoughtfully designed living space, every detail reflects quality and character. Inside, rich hardwood flooring, exposed wood beams, elegant coffered ceilings, and expansive Andersen windows and doors fill the home with natural light. The current owners have further elevated the residence with exquisite custom illuminated built-ins, architectural lighting, and beautifully enhanced living spaces that seamlessly blend traditional craftsmanship with contemporary elegance. At the heart of the home, the chef's kitchen features Caesarstone concrete countertops, a striking custom copper range hood, premium Sub-Zero and Viking appliances, and a generous walk-in pantry. A dedicated wine room and walk-in bar provide additional spaces for entertaining, while the thoughtfully designed floor plan offers a spacious first-floor primary suite with a spa-inspired bathroom and custom closets, along with two additional main-level bedrooms. A private outdoor shower just outside the primary suite offers a spa-like retreat. Upstairs, an impressive transformation has created an exceptional entertainment retreat featuring a completely redesigned custom bar, expansive bonus room, and beautifully appointed home office with captivating views across Lake Virginia. An additional bedroom with a private bathroom and kitchenette offers flexibility for guests or extended stays. The outdoor living experience is truly extraordinary. A magnificent covered lanai with graceful architectural arches and a gas fireplace overlooks the sparkling pool, relaxing hot tub, and beautifully landscaped waterfront grounds. Recently installed automated retractable screens surround the covered patio, allowing you to enjoy the outdoor living areas with added comfort at the touch of a button. Additional features include a UV pool treatment system, outdoor shower, and thoughtfully designed landscape lighting that brings the property to life after sunset. Just beyond the pool, approximately 130 feet of Lake Virginia shoreline opens the door to one of Central Florida's most sought-after lifestyles. Your private dock and covered powered boat lift make it effortless to spend afternoons cruising the Winter Park Chain of Lakes, exploring scenic canals, or simply enjoying the peaceful beauty of the water. Mature trees, lush landscaping, and spectacular lake views create an enchanting setting for both quiet mornings and unforgettable evenings. All of this is conveniently located just minutes from the boutique shopping, acclaimed restaurants, and cultural attractions of Winter Park's iconic Park Avenue. Beautiful homes can be found in many places, but the opportunity to enjoy this extraordinary Lake Virginia lifestyle is something truly special. Welcome home to 541 Virginia Drive.

541 Virginia Drive, Winter Park
2168 Ridge Drive, Winter Park
$365,000
3 Beds ⋅ 2 Baths ⋅ Ridge High 1st Add SubDv. ⋅ 32792 Zip Code
STOP THE SCROLL! ?? Your Dream Home Is Calling! ? Welcome to this beautifully updated 3-bedroom, 2-bath gem where style, comfort, and location come together! Enjoy tasteful updates, newer windows and doors, and a HUGE backyard ready for BBQs, pets, parties, and making memories! Nestled in a quiet friendly neighborhood with plenty of places to walk, you're just minutes from everything—including Full Sail University! Cute house. Big yard. Great location. What more could you want? This one deserves a spot at the top of your must-see list!

2168 Ridge Drive, Winter Park
2352 Sun Valley Circle, Winter Park
$280,000
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Welcome to the established and well-maintained community of Cedarwood Village in highly desirable Winter Park! TREE-LINED STREETS lead to this END UNIT, COMPLETELY REMODELED IN 8/2026 and MOVE-IN READY. This 2-bedroom, 2-bath, BLOCK-CONSTRUCTED condominium offers nearly 1,500 square feet of interior living space and includes a versatile LOFT. As you enter the foyer, you’ll immediately appreciate the attention to detail and pride of ownership, with WOOD FLOORS and fresh neutral paint setting the tone for a stylish and inviting interior. The GREAT ROOM is truly the centerpiece of the home, featuring dramatic 2-story VAULTED CEILINGS that create an exceptionally open, voluminous, and luxurious atmosphere. A magnificent corner focal point showcases a cozy WOOD-BURNING FIREPLACE with raised slate tile hearth, while mantle columns extend the full height of the room and frame a soaring vertical mirror that reflects natural light and visually expands the space. TWO SKYLIGHTS further enhance the natural light. From the living area, enjoy serene views of the lanai and lush GREEN SPACE beyond. A stylish WET BAR is tucked into a recessed alcove and beautifully illuminated by warm integrated accent lighting, featuring a POLISHED GRANIT COUNTERTOP and contemporary shaker-style cabinetry—perfect for entertaining. The second-story LOFT provides an incredible overlook into the Great Room below and serves as a highly desirable FLEX SPACE, complete with BLACK WROUGHT-IRON SPINDLE RAILING, modern neutral carpeting, its own SKYLIGHT, and a convenient STORAGE CLOSET. The kitchen features sleek light-gray SHAKER-STYLE CABINETRY, elegant GRANITE COUNTERTOPS, and premium STAINLESS-STEEL APPLIANCES. An oversized peninsula island with deep undermount sink and gooseneck faucet doubles as a breakfast bar for casual dining and entertaining. A charming EAT-IN NOOK overlooks the PRIVATE COURTYARD and provides access through wide sliding glass doors, creating the perfect spot for morning coffee or outdoor dining. For added convenience, the laundry closet, complete with WASHER AND DRYER, is conveniently located within the kitchen. The PRIMARY SUITE offers a peaceful retreat with both WALK-IN and step-in closets, direct lanai access through sliding glass doors, and a beautifully REMODELED ENSUITE BATH accessed through a stylish modern barn door. The bath features a DUAL-SINK VANITY, large walk-in shower with frameless glass door, and private water closet. The spacious SECOND BEDROOM also features a WALK-IN CLOSET and convenient access to the REMODELED HALL BATH, providing privacy for residents while comfortably serving guests. Additional features include a location directly across from green space, 2 DESIGNATED PARKING spaces in front, and a PRIVATE MAILBOX. With LOW HOA DUES, residents enjoy a sparkling community pool, clubhouse, tennis and basketball courts, pickleball, FENCED DOG RUN, and pet walk with waste stations. Monthly fees also include ROOF AND EXTERIOR BUILDING MAINTENANCE, PEST CONTROL, and LANDSCAPING. This ideal Winter Park location is directly across from Casselberry Commons, offering a variety of major retailers, Publix, and fast-food options. Just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, restaurants, entertainment, and medical facilities, this exceptional home combines sophisticated living with convenience in one of Central Florida’s most desirable locations. See video and virtual tour.

2352 Sun Valley Circle, Winter Park
1940 Magnolia Avenue, Winter Park
$1,190,000
4 Beds ⋅ 4 Baths ⋅ Temple Terrace Annex SubDv. ⋅ 32792 Zip Code
New roof fall 2026! Exceptional custom-built estate offering unparalleled security, efficiency and peace of mind on two expansive lots in the heart of Winter Park. This split-plan three-bedroom and 2.5-bath home has over 4,880 total square feet in the main home and 1,944 total square feet in the detached in-law/office unit under roof. Constructed with solid poured concrete block and 1-inch insulation, this remarkable residence was designed to withstand the test of time while delivering modern luxury and comfort. A rare feature, the home includes two reinforced safe rooms built with rebar-reinforced solid poured concrete walls and 12-inch concrete ceilings, along with a built-in, concrete-bolted safe. Additional security enhancements include a full alarm system and security spotlights. Designed for everyday living and entertaining, the property is equipped with a full-house 22-kilowatt generator, a buried 500-gallon propane tank, propane gas range and outdoor grill, two tankless water heaters, whole-house water softening and filtration systems, EV charging capability and energy-efficient construction resulting in remarkably low utility costs. The well-appointed kitchen features a solid wood cabinetry, quartz countertops, a kitchen, butler pantry, coffee bar and laundry room, Verona gas range, Frigidaire Professional French-door refrigerator, KitchenAid dishwasher, convenient under-counter outlets and the kitchen island has lighted shelves. Additional highlights include plantation shutters throughout, wine cellar, climate-controlled storage attic, granite in baths, custom garage cabinetry, epoxy-finished garage floors, hurricane-impact windows in the office/apartment, Pet Turf in the entire backyard with no maintenance necessary and a striking 35-foot flagpole. Combining superior craftsmanship, advanced infrastructure and thoughtful upgrades rarely found in today's market, this extraordinary property presents a unique opportunity to own a one-of-a-kind residence. Total heated square footage includes heated/cooled space to use as garage, workshop, and/or utility room in the detached structure.

1940 Magnolia Avenue, Winter Park
1401 Pelham Road, Winter Park
$650,000
3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Welcome home to this charming 1940's bungalow in Orwin Manor, one of Winter Park’s most sought-after neighborhoods. The single-story home has 3 bedrooms, 2 full baths and 1,594 square feet of living space. It keeps its original character, with wood floors throughout and graceful curved entryways. In the living room, a wood-burning fireplace sets a warm, inviting tone, and the open layout flows into the formal dining room, making the home easy to entertain in and comfortable for everyday living. The kitchen has been updated with shaker cabinetry, granite countertops and stainless steel appliances, while keeping the home’s vintage charm. A split bedroom plan gives the primary suite added privacy, with an en suite bath featuring a walk-in shower and a walk-in closet. Outside, the home sits on an oversized 0.31-acre lot (100 x 135), leaving plenty of room for gardening, play, outdoor living or future expansion, and a detached one-car garage adds storage and parking. HVAC 2020, Water Heater 2020. Orwin Manor is a well-established, walkable community close to Winter Park’s restaurants and shopping, with easy access to major roadways. This home has great bones and a prime location, with plenty of potential to make it your own. Opportunities like this in Orwin Manor don’t come along often, so schedule your private showing today!

1401 Pelham Road, Winter Park
1200 Via Salerno, Winter Park
$5,995,000
5 Beds ⋅ 6 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code
Some homes are built, and some are composed. At 1200 Via Salerno, every finish, fixture, & detail was chosen with one goal in mind: a residence that is a pleasure to live in every day and will feel just as right decades from now. Set on nearly half an acre in the highly desirable Vias of Winter Park, this fully renovated, turnkey home is modern European design at its most elegant and understated, with bespoke cabinetry & built-ins in every room and rare natural stone throughout. It offers five bedrooms, five full baths, a half bath, and has been curated with the care of a private collection. A sculptural curved staircase greets you in the foyer, and wood floors carry through the main level. The living room rises beneath vaulted ceilings, centered on a gas fireplace wrapped in Sequoia quartzite, with a wall of sliding glass doors opening to the pool so gatherings drift outdoors without a second thought. In the kitchen, rare leathered Naica quartzite forms the waterfall island, countertops, & backsplash, and custom cabinetry rises floor to ceiling. Appliances include a Wolf gas range with pot filler, Sub-Zero refrigerator, & two Miele dishwashers, plus a prep sink, concealed outlets, & push-to-open, soft-close drawers. To one side, a pantry/butler’s passage with matching cabinetry also houses the laundry. At the front of the home, a bright formal dining room & eat-in area complete the space. Just off the eat-in area, a large turf side courtyard offers a low-maintenance space where kids & pets can play within view of the kitchen. The main-level primary suite features two walk-in closets & a double-sided wood-burning fireplace shared with the private office. The spa-inspired bath showcases leathered Taj Mahal quartzite with integrated dual sinks, an extra-large soaking tub for two, & a walk-in shower, all with Graff fixtures. The office opens to the pool and is outfitted with floor-to-ceiling shelving, cabinetry, & file drawers, versatile enough to become a dressing room. The whiskey lounge with custom wet bar is sized for a game room or second office. A powder room completes the main floor. Upstairs, custom cabinetry lines the loft & hallway, offering storage at every turn. To the left, two bedrooms share an elegant bath with dual sinks and a separate tub & shower, and a single door closes them off creating an optional, private two-bedroom suite. To the right, two additional bedrooms each enjoy an en suite bath. Every bedroom is finished with built-in closets. A separate upstairs wing houses the generously sized media room, with state-of-the-art surround sound & extensive hidden storage. Outdoors, a weathered marble pool deck surrounds the saltwater pool, framed by grounds created by Signature Landscape. The garden pavilion with its own fireplace is one of the home’s most special spaces, joined by a summer kitchen with stone counters & wall, a natural gas grill, & a sink, plus a pool bath. Additional features include a three-car side-entry garage with epoxy floors, EV charger capability, & ample storage, along with Lutron lighting on the main level, Toto toilets throughout, water filtration, natural gas, a whole-home generator, & three Trane HVAC systems. The Winter Park Racquet Club, Interlachen Country Club, the shops & dining of Park Avenue, and the Winter Park 9 golf course are all within walking distance. Refined, move-in ready, and crafted without compromise, 1200 Via Salerno awaits its next owner.

1200 Via Salerno, Winter Park
1735 Demetree Drive, Winter Park
$1,050,000
4 Beds ⋅ 3 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code
Beautifully maintained Winter Park pool home with a 2026 whole-home repipe, 2019 roof, and 2022 A/C in the desirable Waterbridge neighborhood. Discover the charm of established Winter Park living in this inviting single-story home, situated on a beautifully landscaped 0.36-acre lot in the sought-after 32789 ZIP code. Spacious living areas, abundant natural light, and two inviting fireplaces, including a fireplace in the living room and a distinctive stone fireplace in the primary suite, create a warm and welcoming atmosphere. Step outside to your private swimming pool, surrounded by mature landscaping, offering the perfect setting for relaxing or entertaining. Additional features include a tankless water heater, updated pool equipment, and access to Waterbridge neighborhood tennis courts. An exceptional Winter Park location. Enjoy convenient proximity to AdventHealth Winter Park Hospital, the Winter Park VA Clinic, and Winter Park High School, along with easy access to downtown Winter Park's iconic Park Avenue, renowned restaurants, boutique shopping, Rollins College, Mead Botanical Garden, and downtown Orlando. Combining valuable improvements, single-story convenience, private pool living, and an established neighborhood setting, 1735 Demetree Drive offers the character, comfort, and lifestyle that make Winter Park, Florida, such a desirable place to call home.

1735 Demetree Drive, Winter Park
506 Lander Road, Winter Park
$450,000
3 Beds ⋅ 2 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code
Investor or renovation opportunity in the Winter Park High school district! This solid block home features a great location for the buyer with vision. Opportunity awaits at 506 Lander Road in Winter Park! Situated on a spacious lot of approximately 0.22 acres, this 3-bedroom, 2-bath home offers 1,346 square feet of living space and plenty of potential for its next owner. Built in 1958, the property is ready for updates and improvements, presenting an opportunity for investors, renovators, or buyers looking to create a space of their own. The generously sized lot provides additional possibilities for outdoor living and landscaping. Conveniently located near shopping, dining, parks, and major roadways, with easy access to all that Winter Park and the surrounding areas have to offer. Bring your vision and explore the potential of this property!

506 Lander Road, Winter Park
808 Densmore Drive, Winter Park
$509,999
3 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
Welcome to 808 Densmore Drive, a beautifully updated 3-bedroom, 2-bathroom pool home tucked into the established Winter Park Estates neighborhood! Blending modern farmhouse charm with thoughtful upgrades, this home offers 1,460 square feet of inviting living space designed for both everyday comfort and entertaining. Step inside to a bright, open floor plan where the spacious living and dining areas flow effortlessly into the kitchen, complete with quartz countertops, stainless steel appliances, a built-in microwave, tile backsplash, and a window overlooking the outdoors. On the opposite side of the home, you'll find three comfortable bedrooms and two beautifully updated bathrooms, offering a practical layout with plenty of privacy. An oversized interior laundry room and enclosed porch provide additional functional space. Outside is where this home truly shines! The private backyard features a sparkling in-ground pool, a newly installed paver patio (2025), and a brand-new fence (2026), creating an inviting setting for weekend gatherings, outdoor dining, or relaxing in the Florida sunshine. Recent improvements also include a new irrigation system and control panel (2026), updated pool filtration equipment (2026), and a water heater replaced approximately three years ago. Beyond the property, enjoy a prime Winter Park location just minutes from Cady Way Trail, Winter Park Pines Golf Course, Rollins College, and the shopping, dining, and charm of Park Avenue. With its updated interiors, private pool, and convenient access to everything Winter Park has to offer, 808 Densmore Drive is ready to welcome you home!

808 Densmore Drive, Winter Park
1600 Legion Drive, Winter Park
$3,495,000
5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code
Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

1600 Legion Drive, Winter Park
1681 Woodland Avenue, Winter Park
$2,629,000
5 Beds ⋅ 5 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code
Under Construction. A striking interpretation of Modern Tudor design brings a fresh architectural presence to one of Winter Park’s charming brick streets. Newly built, this stunning residence pairs a distinctive façade with interiors that feel both richly detailed and effortlessly livable. From the marble mosaic foyer to the private poolside retreat, each space offers its own expression of luxury, creating a home with character, warmth, and a beautiful sense of arrival. Beyond the entry, the spacious living area unfolds beneath shiplap ceiling details that lend texture and architectural depth. A statement wall with an electric fireplace anchors the room, establishing an inviting setting for quiet evenings and lively gatherings alike. The kitchen takes center stage with Taj Mahal countertops and a full suite of Thermador appliances. A built-in paneled refrigerator preserves the cabinetry’s seamless appearance, while a spacious walk-in pantry provides ample storage beyond the main kitchen. Positioned downstairs, the primary suite offers a peaceful retreat with a spacious closet and a beautifully composed spa bath featuring dual vanities, a freestanding soaking tub, and a separate shower with a rain showerhead and marble mosaic tile. A second downstairs guest suite adds exceptional versatility, a rare feature for the area, providing comfortable accommodations for visitors or a space for a private office. Providing comfortable accommodations for visitors or an inspiring space for a private office. Upstairs, three additional bedrooms, each with a walk-in closet, offer room for family and guests. A spacious loft introduces another place to gather, unwind, or create a dedicated media or recreation space, while the upstairs laundry room brings convenience to daily routine. Outdoors, a covered lanai with a summer kitchen sets the scene for alfresco dining and entertaining space. Lush landscaping surrounds the pool and spa, creating a beautiful backdrop for entertaining or simply enjoying the Florida lifestyle. Energy efficient doors and windows complete the home’s thoughtful collection of features. The location places neighborhood favorites within easy reach, with Phelps Park and the YMCA just a walk away and Park Avenue’s shops, restaurants, and cafés a short golf cart ride from home. Distinctive in its architecture and generous in its design, this residence offers a compelling opportunity to enjoy brand-new construction amid the established charm of Winter Park.

1681 Woodland Avenue, Winter Park
2640 Beverly Avenue, Winter Park
$305,000
3 Beds ⋅ 1 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code
Solid 1949 bungalow on a usable 50 x 150 lot (approx. 7,553 sq ft) in unincorporated Orange County with a Winter Park mailing address, just blocks from Lake Killarney. A clean shell for a fix-and-flip or a hold-and-rent strategy, with detached ADU potential under Orange County rules. 3 bed, 1 bath, approx. 1,216 sq ft of living area on approx. 0.17 acre, FEMA Zone X (minimal flood hazard). Straightforward single-story footprint with room to improve, not expanded. Out back, a canopy of mature trees creates a shaded, private backyard sanctuary. Already handled: brand-new roof (October 2026) and a replaced water heater. Kitchen cabinets are in very good shape; if you choose to update the countertops, keep the cabinets and simply resurface and repaint. The deck is in good condition today (plan on rebuilding down the road). Still to do: central HVAC is not operational (home is cooled by window units), the shower needs a light spruce-up, and a cosmetic refresh throughout. Strong bones and a good shell for a focused remodel. Location: Lake Killarney, a 234-acre spring-fed lake, is just blocks away, where seaplanes drop in for lunch at Hillstone. Centrally located to I-4 at Fairbanks Avenue, with downtown Orlando about 15 minutes away. Less than 2 miles to the newly renovated Winter Park Village with its Regal cinema, restaurants, boutiques and patio dining, and minutes to Park Avenue, Rollins College, the Morse Museum, the Saturday Farmers Market, Trader Joe's, Whole Foods, AdventHealth Winter Park and the Winter Park SunRail station. ADU snapshot: under Orange County R-1A (Sec. 38-1426), a detached one-story ADU is typically limited to 50 percent of the primary living area or 1,000 sq ft, whichever is less, about 608 sq ft here. The lot appears to meet the 7,500 sq ft minimum. Homestead and owner-occupancy rules apply. Buyer to verify all zoning, setback, ADU eligibility, homestead and permitting items directly with Orange County Zoning. Figures are informational only and not a guarantee of approval. Renovate the primary and add a rental ADU for a two-income setup, or flip it. New roof and water heater done, interior ready for a focused remodel.

2640 Beverly Avenue, Winter Park
1939 Woodcrest Drive, Winter Park
$1,349,000
4 Beds ⋅ 4 Baths ⋅ Acreage SubDv. ⋅ 32792 Zip Code
Welcome to refined modern living in the heart of Winter Park. Meticulously crafted in 2020, this stunning two story residence showcases four bedrooms, three full baths, and a convenient powder bath. The main level welcomes you with an open concept design bathed in natural light, high ceilings, and seamless flow between the living and dining areas. Perfect for culinary enthusiasts, the chef inspired kitchen is appointed with smart GE Cafe appliances, a gas range, premium quartz countertops, custom cabinetry, and a spacious center island. A private main level home office provides a quiet, dedicated environment for work or study. The first floor primary retreat offers everyday luxury with direct pool access, dual walk in closets, and a spa caliber en suite bath featuring contemporary fixtures, a dedicated linen closet, and an expansive walk in super shower. Upstairs, a versatile open loft serves as an ideal second living room, game room, or media retreat, anchoring three generous guest bedrooms with ample closet space and beautifully finished full bathrooms. Step through sliding glass doors into your private outdoor sanctuary, complete with a fully screened swimming pool featuring a sun shelf, paved patio lounging, and pre plumbing ready for your custom summer kitchen. Situated in one of Central Florida's most desirable residential pockets, this address provides premier Orange County living within comfortable walking distance to top rated Winter Park High School, Glenridge Middle School, and Brookshire Elementary. Located just minutes from the vibrant shopping, dining, and cultural attractions of Park Avenue, this turnkey 2020 build seamlessly unites contemporary luxury with quintessential Winter Park convenience.

1939 Woodcrest Drive, Winter Park
1355 Hibiscus Avenue, Winter Park
$2,100,000
5 Beds ⋅ 6 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Virtually Staged. Situated along one of Winter Park's charming, tree-lined brick streets, this beautifully maintained traditional residence offers over 4,100 square feet of thoughtfully designed living space, with 5 bedrooms, 5 full bathrooms, and 1 half bath. Timeless architectural details and modern comforts create a welcoming home designed for both everyday living and entertaining. A welcoming front porch leads into elegant interiors featuring a private office with custom built-ins and a glass pocket door, along with a formal dining room accented by a tray ceiling and ambient lighting. The living room showcases exposed ceiling beams, crown molding, built-in shelving, and a gas fireplace, while French doors open to the screened lanai, creating a seamless connection to the outdoors. The kitchen features expansive countertops, abundant cabinetry, a center island with prep sink, walk-in pantry, and breakfast nook with access to the outdoor living area. A butler's pantry with wine refrigerator adds convenience for entertaining. The main-level primary suite offers a relaxing retreat with dual vanities, a soaking tub, and multiple closets. A second ensuite bedroom on the first floor, complete with a beverage refrigerator and coffee station, provides additional privacy and comfort for guests. A dedicated laundry room completes the main level. Upstairs, a built-in desk and cabinets line the hallway for study or work space. Generous loft with custom cabinetry, accent lighting, and beverage refrigerator creates a versatile second living area. Three additional bedrooms provide comfortable accommodations, including two connected by a Jack-and-Jill bathroom and a third with access to a nearby full bath. The second laundry room adds flexibility and convenience. Outdoors, enjoy a private backyard retreat featuring a screened lanai, swimming pool, outdoor kitchen, mature landscaping, and a full pool bathroom. Recent improvements include interior paint, a new second-floor Daikin AC system with UV lights, updated Hayward pool equipment, including the pump, DE filter, heater, chlorination system, whole-house Brita water filtration, epoxy garage flooring, new carpeting, refinished wood floors, polished countertops, and fiber-optic connectivity. Additional updates include a new roof (2023), commercial-grade water heater (2022), exterior paint (2024), and new appliances: fridge, dishwasher, washer and dryer. Conveniently located near the Vias and Winter Park Racquet Club, and just minutes from Park Avenue's renowned shopping and dining, the YMCA, medical facilities, and nearby public and private schools, this home offers the charm of Winter Park living with convenient access to recreation, dining, and everyday essentials.

1355 Hibiscus Avenue, Winter Park
1737 Indiana Avenue, Winter Park
$1,399,900
4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
WELCOME to this farmhouse-inspired residence combines timeless architectural character with modern luxury and thoughtful design. ***A welcome front porch leads to an impressive two-story foyer and bright, open floor plan designed for comfortable living and effortless entertaining. A private fourth bedroom with a full bath is located near the entry, offering flexibility as a guest suite, home office, study, or secluded retreat. ***KITCHEN & MAIN LIVING AREAS: The gourmet kitchen serves as the heart of the home, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package with a 36-inch electric cooktop. Open to the spacious living and dining areas, it creates a seamless setting for everyday living and entertaining. ***PRIMARY SUITE & UPSTAIRS SPACES: The first-floor primary suite provides a peaceful retreat with a spa-inspired bath, dual vanities, a freestanding soaking tub, and a generous walk-in closet with custom shelving. A nearby laundry area adds convenience and efficiency. Upstairs, a spacious bonus room with a closet can function as a fifth bedroom, media room, game room, home office, creative studio. Two additional bedrooms feature walk-in closets and share a beautifully appointed bathroom with dual sinks. A second laundry room with a sink and abundant natural light adds further convenience. ***OUTDOOR LIVING: The covered lanai overlooks a sparkling pool and beautifully landscaped backyard, creating for the outdoor relaxation and entertaining. The entire covered porch features a motorized retractable screening system, allowing the space to be fully screened in. Low-maintenance artificial turf keeps the backyard looking lush and green year-round without the need for mowing, while an additional mosquito repellent system enhances outdoor enjoyment. ***LOCATION: Perfectly positioned near Winter Park's acclaimed shopping, fine dining, beautiful parks, and vibrant cultural attractions, this exceptional location also offers effortless access to I-4 and Downtown Orlando, Winter Park Village, Publix, Trader Joe's, and much more, making it easy to enjoy everything Central Florida Lifestyle. Make an appointment today before this beautiful, amazing home is gone!!!

1737 Indiana Avenue, Winter Park
2322 Woodcrest Drive, Winter Park
$650,000
4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code
Set on a quiet, landscaped, quarter-acre lot, this 4-bedroom, 2-bath POOL HOME offers a rare combination of privacy, space and neighborhood charm - all within the Kenilworth Shores neighborhood of Winter Park. Step inside to find an open and inviting great room filled with natural light and framed by sliding doors overlooking the pool and backyard. At the center of the home, the fully remodeled kitchen features shaker-style cabinetry with a built-in pantry, granite countertops, stainless steel appliances and a large breakfast bar with plenty of space for casual dining and entertaining. Step outside to the screened porch and pool, creating a wonderful extension of the living space for year-round Florida living. The landscaped yard includes an irrigation system and plenty of outdoor space. The primary suite features a walk-in closet and fully updated ensuite bathroom showcasing a beautiful granite topped vanity, updated fixtures and new shower. The renovated hall bath features a granite topped vanity with dual sinks, tile and fixtures. Major updates include a BRAND NEW HVAC system installed in 2026, NEWER ROOF and water heater, insulated DOUBLE PANE WINDOWS, and a new septic drainage field in 2024. The oversized two-car garage and large driveway provide plenty of parking and storage. The location puts you close to so much of what makes Winter Park desirable. WINTER PARK HIGH SCHOOL is within walking distance, with Brookshire Elementary and Glenridge Middle also nearby. Park Avenue is a 10 minute drive, while Baldwin Park and the Lake Baldwin trail and dog park are a five minute walk from the home. Enjoy easy access to Full Sail University, UCF, Valencia College, major transportation routes and Orlando International Airport. With its extensive updates, private pool and convenient Winter Park location, this home is truly move-in ready—schedule your private showing today and come see everything 2322 Woodcrest Drive has to offer!

2322 Woodcrest Drive, Winter Park
2823 Parkland Circle, Winter Park
$3,250,000
5 Beds ⋅ 6 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code
JUST COMPLETED NEW CONTRUCTION in the heart of Winter Park. Tucked away on a quiet cut-de-sac in an established neighborhood surrounded by beautiful newer residences, this nearly 4,500 square-foot home pairs thoughtful design with exceptional indoor-outdoor living. An impressive entry foyer sets the tone for a residence filled with designer details and and a floor plan featuring five en-suite bedrooms, six full baths, and the convenience of two laundry rooms to serve each floor. At the heart of the home, the chef's kitchen is appointed with Thermador appliances and designed for every day living and entertaining. Expansive living spaces are anchored by an indoor fireplace, and flow seamlessly to the covered lanai, where a second fireplace, fully equipped outdoor kitchen and private pool create an exceptional setting for year-round Florida living. Outdoor lush tropical landscaping and striking gas lanterns give the home a distinctive sense of arrival and timeless curb appeal. An oversized garage provides generous space for vehicles and storage, while integrated smart-home features including cameras, alarm, smart switches, and speakers with Sonos, bring modern convenience throughout. Zoned for sought-after Audubon Park School and Winter Park High School.

2823 Parkland Circle, Winter Park
266 N Ranger Boulevard, Winter Park
$724,900
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
FULLY RENOVATED Winter Park Pines Home with Mother-in-Law Suite, NO HOA & Prime Location! Welcome to this beautifully transformed Winter Park Pines residence, where modern design, thoughtful upgrades, and flexible living spaces come together in one exceptional home. Ideally located adjacent to the Cady Way Trail, with NO HOA, this property offers the lifestyle and convenience of Winter Park with the flexibility today’s buyers are looking for. Upon entering, you’re greeted by a dramatic custom charcoal accent wall with geometric detailing, creating a distinctive architectural focal point and setting the tone for the home’s contemporary design. Inside, the open and inviting floor plan features Luxury Vinyl Plank flooring throughout, recessed LED lighting, all-new interior doors, and a stylish LED fireplace that adds warmth and ambiance to the main living area. The completely renovated kitchen is designed for both everyday living and entertaining, featuring new Shaker-style cabinetry, Quartz countertops, a large center island, luxury backsplash, stainless-steel appliances, and a dedicated coffee bar with wine refrigerator. The open layout provides an ideal gathering space for family and guests. The home also features a private Mother-in-Law Suite with its own entry and outside walkway, offering exceptional flexibility for extended family, overnight guests, a home office, or a private living area. The suite includes its own beautifully renovated bathroom with a rain shower, enclosed by a ceiling-to-threshold glass pane, and an illuminated LED mirror. The primary suite bathroom has been upgraded to a luxurious, contemporary retreat, featuring a smart toilet, dual vanities, illuminated LED mirror, and an executive-style stand-up rain shower. The shower incorporates a thoughtfully designed inclined floor that directs water into a rectangular drain, along with a striking floor-to-ceiling glass enclosure, creating a clean, open, and refined feel without the need for a traditional shower curtain. Additional major improvements include a new Carrier HVAC system, tankless water heater, updated double-pane windows, complete re-plumbing, re-wiring with an updated electrical panel, and a new roof installed 7/17/2023. Step outside and enjoy the home’s inviting outdoor spaces, including a covered front porch with dusk lighting, screened rear porch, spacious backyard, and oversized driveway. A series of cement slab walkways, separated by polished, large river stones, leads from the garage to the front door, with matching paths continuing along the rear of the home. Solar security lighting and decorative LED lighting add both functionality and evening ambiance. Ideally situated in Winter Park Pines and directly adjacent to the Cady Way Trail, the home offers convenient access to major roadways, hospitals, golf courses, colleges, shopping, dining, and highly regarded private schools—all within a short drive. With an extensive renovation, three beautifully updated bathrooms, a private Mother-in-Law Suite, modern kitchen, tankless water heater, new roof, updated electrical and plumbing, NO HOA, and an outstanding Winter Park location, this home offers a rare combination of style, functionality, and convenience. Come experience the renovation, thoughtful details, and flexible floor plan in person. Schedule your private showing today!

266 N Ranger Boulevard, Winter Park
7498 Aloma Pines Court, Winter Park
$355,000
3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code
Welcome to beautiful Winter Park. This Townhome in Gated Aloma Trails has been meticulosly maintained. With an open and spacious floor plan is great for family activities and entertaining. NEW HV/AC AND NEW WATER HEATER. kitchen features all stainless steel appliances, large island great for prep with seating for "4" or more on the oposite side. The large slider leads out to your 5' X 11" private lani, allows natural light to fill the entire space. There is a first floor powder room for convenience for you and your guest. Second floor laundry closet for your convenience. Your oversize primary bedroom features a spacious walk-in closet and ensuite with large vanity and double sinks. There are "2" additional guest bedrooms. The home has a one car garage with an extended pad for a second car. the NEW water heater is located in the garage. The A/C is also NEW. Aloma Trails is convenient to shopping directly accross the street from the complex. minutes from Aloma (426), 417, UCF, Full Sail, Rollins, a Park Ave., Airport and Beaches. SELLER IS MOTIVATED

7498 Aloma Pines Court, Winter Park
173 Scottsdale Square Unit 173, Winter Park
$100,000
1 Beds ⋅ 1 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
INVESTMENT OPPORTUNITY! Add this well-maintained condo to your investment portfolio or make it your next income-producing property. Featuring a functional layout, neutral finishes, easy-care flooring, stainless-steel appliances, and plenty of natural light, this unit offers an attractive and low-maintenance option for investors. The comfortable living area flows to the outdoor space through sliding glass doors, creating a bright and inviting atmosphere. Conveniently located near shopping, dining, major roadways, and everyday necessities. Whether you're expanding your rental portfolio or looking for your next investment opportunity, this condo is worth a look. Schedule your showing today!

173 Scottsdale Square Unit 173, Winter Park
532 Langholm Drive, Winter Park
$2,990,000
5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code
Under Construction. Commanding attention with its striking architecture and exceptional presence, this brand-new Winter Park residence unfolds across an expansive 11,000-square-foot homesite in the fast growing Kenilworth Shores neighborhood. Striking curb appeal introduces the home, while a marble mosaic foyer provides an elegant first impression and leads into the expansive great room. At the center of the living space is a dramatic custom entertainment wall featuring illuminated built-in shelving and a sleek electric fireplace. The adjoining dining room is equally impressive, complete with an oversized dry bar, wine refrigerator, and glass-front cabinetry, creating the perfect setting for hosting family and friends. The designer kitchen makes a statement with Taj Mahal countertops, a marble mosaic backsplash, custom cabinetry, and a full suite of Thermador appliances, including a paneled built-in refrigerator. A massive butler’s pantry extends the kitchen’s functionality with abundant storage and preparation space, a second microwave and oven, and an additional dishwasher, making entertaining effortless. The downstairs primary suite offers a private retreat accented by warm wood beams and separate his-and-hers closets. Its jaw-dropping spa-inspired bathroom is wrapped in 12-by-24-inch marble tile and features dual vanities, a freestanding soaking tub, and an oversized walk-in shower with LED-illuminated niches. A dedicated home office is also located on the main level, providing a quiet and refined space for working from home. Upstairs, a massive bonus room creates a flexible second living area ideal for movie nights, a game room, or a children’s retreat. Four additional spacious bedrooms offer comfort and privacy for family and guests, while an upper-level balcony provides another inviting place to unwind. The outdoor living spaces are designed to take full advantage of the oversized lot. A large covered lanai with a complete summer kitchen overlooks the resort-style pool and spa, all framed by an elegant marble deck. Beyond the pool, the expansive backyard offers valuable green space for recreation, entertaining, or relaxation. Additional highlights include a complete impact-rated window and door package for added efficiency and peace of mind. Perfectly positioned near Cady Way Park, AdventHealth Winter Park, and just a golf-cart ride from Park Avenue, this extraordinary new residence presents a rare opportunity to experience uncompromising luxury, exceptional space, and the very best of the Winter Park lifestyle.

532 Langholm Drive, Winter Park
533 Country Club Drive, Winter Park
$1,599,000
4 Beds ⋅ 4 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code
Welcome to 533 Country Club Drive, a beautifully designed custom residence where timeless coastal style meets effortless Florida living. Located in the Lake Killarney Shores community, this 4-bedroom, 3.5-bath pool home offers 2,942 square feet of thoughtfully designed living space, along with exclusive access to the neighborhood’s private boat ramp and dock on Lake Killarney just across the street. Inside, soaring 10-foot ceilings, 8-foot solid doors, wood flooring and designer lighting create a bright, refined atmosphere. The inviting living room is centered around a natural gas fireplace and opens seamlessly to the pool and covered rear lanai, creating an exceptional indoor-outdoor setting for everyday living and entertaining. The gourmet kitchen impresses with 42-inch designer cabinetry, quartz countertops, tile backsplash, farmhouse sink and an oversized quartz island with generous seating. A premium Viking stainless steel appliance package includes a gas range and hood, French-door refrigerator and dishwasher, complemented by a microwave drawer. The highly desirable dual-primary-suite layout provides exceptional comfort and flexibility. The first floor offers a private bedroom with an ensuite bath, providing convenient accommodations for guests or extended stays. Upstairs, the main primary retreat features wood flooring, an oversized custom closet and a spa-inspired ensuite bath with a combined soaking tub and shower wet area. Two additional bedrooms and a spacious loft complete the second level, offering flexible space for relaxing, entertaining or working from home. Step outside to a private oasis featuring a 10-by-25-foot POOL with a sun shelf, travertine coping and a paver deck. The covered rear lanai includes a SUMMER KITCHEN equipped with a Napoleon gas grill, vented hood, granite countertops, beverage cooler and storage—perfectly designed for year-round dining, entertaining and relaxing by the pool. Recent improvements include custom window treatments throughout, upgraded office and closet installations, privacy and heat-resistant window tinting, an infrared/UV HVAC enhancement, epoxy garage floor and under-stair storage. Additional features include zoned air conditioning with Nest thermostats, a Rinnai tankless gas water heater, Low-E windows, recessed LED lighting, a metal front porch roof and pavers extending across the driveway, walkway, porch and lanai. Enjoy the best of the Winter Park lifestyle with outstanding shopping, dining and entertainment nearby. Winter Park Village is just moments away, while the boutiques, sidewalk cafés, celebrated restaurants and cultural attractions of Park Avenue are also within easy reach. Convenient access to Fairbanks Avenue, US 17-92 and I-4 provides an easy connection to Downtown Orlando, Maitland and destinations throughout Central Florida. This exceptional home brings together custom craftsmanship, beautiful finishes, an enviable lakeside setting and one of Winter Park’s most desirable locations. Schedule your private showing today and experience the custom craftsmanship, lakeside lifestyle and exceptional Winter Park location of 533 Country Club Drive.

533 Country Club Drive, Winter Park
4260 Bear Gully Road, Winter Park
$585,000
4 Beds ⋅ 4 Baths ⋅ Bear Gully Forest SubDv. ⋅ 32792 Zip Code
RENOVATED 4 BED / 3.5 BATH ON AN OVERSIZED 0.57-ACRE LOT | GOURMET KITCHEN | SCREENED LANAI | FENCED YARD | ROOF 2018 | FLOOD ZONE X | LOW HOA. Welcome to 4260 Bear Gully Road, a move-in-ready two-story home on nearly 25,000 sq ft of land, with space for a pool, garden or play area (buyer to verify). The gourmet kitchen was fully remodeled two years ago with upscale cabinetry and modern appliances, and luxury vinyl flooring gives the home a clean, low-maintenance look. The primary suite is on the first floor with a walk-in closet, and four bedrooms and three and a half baths give everyone room for family, guests or a home office. Ceiling fans, a two-car garage with opener, and concrete block and stucco construction add comfort and peace of mind. Relax on the screened lanai overlooking the large fenced backyard. Near Publix-anchored shopping and dining on Aloma Avenue, AdventHealth Winter Park, the Cross Seminole Trail and SR 417, with Winter Park Village and Park Avenue a short drive away. Seminole County schools: Eastbrook Elementary, Tuskawilla Middle and Lake Howell High (buyer to verify). Schedule your showing today!

4260 Bear Gully Road, Winter Park
5080 Seminole Avenue, Winter Park
$299,900
3 Beds ⋅ 2 Baths ⋅ Suburban Homes SubDv. ⋅ 32792 Zip Code
FULLY FURNISHED and ready for its next owner! This 3-bedroom, 2-bath Winter Park home offers an excellent combination of recent improvements, location, and flexibility. Major updates include a NEW ROOF (2021), FULL HOUSE REPIPE (2025), and NEW FLOORING (2025), giving buyers peace of mind on several important big-ticket items. Situated on an OVERSIZED 0.24-ACRE LOT with NO HOA, the property offers a spacious yard with plenty of room to enjoy the outdoors. Inside, the home features a comfortable and functional layout with an eat-in kitchen, indoor laundry, and inviting living spaces. Even better, the home is being sold FULLY FURNISHED, making it an easy option for a primary residence, second home, or investment property. The location is hard to beat, with convenient access to Full Sail University, Rollins College, UCF, Park Avenue, Baldwin Park, shopping, dining, and major roadways connecting you throughout Central Florida. With NO HOA and short-term rental potential, this property provides flexibility that can be difficult to find in Winter Park. Whether you're looking for a place to call home or an investment opportunity, 5080 Seminole Ave is ready for its next chapter!

5080 Seminole Avenue, Winter Park
2572 Fifeshire Drive, Winter Park
$899,900
4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 2nd Add SubDv. ⋅ 32792 Zip Code
Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner lot along a beautiful street in a sought-after community. Offering more than 2,500 square feet of living space, this spacious residence features four bedrooms and two-and-a-half baths, with an open, comfortable layout designed for both everyday living and entertaining. The home has been thoughtfully updated and maintained over the years, blending timeless character with modern conveniences. The kitchen was beautifully remodeled in 2021 with new cabinetry, appliances, flooring and countertops, while the family room was enhanced with additional air-conditioning ducts and vents for added comfort. The second full bath was also remodeled in 2021 and the downstairs powder room received a stylish update in 2025.Significant improvements include new wood flooring downstairs and refinished and stained upstairs floors in 2019, a new HVAC system with an additional upstairs unit and complete ductwork replacement in 2020 and a customized primary closet in 2022. The primary suite continues to impress with a new porch door and a private balcony railing added in 2026. A new water heater was installed in 2023, while the main sewer line exiting the home was replaced in 2024. The garage is air-cooled. Outdoor living has been equally well considered, with a screened porch enclosure, a covered side patio, new fencing and refreshed landscaping creating inviting spaces to relax and entertain. Beyond the home itself, the location is exceptional, conveniently situated in a wonderful community with Cady Way pool and Cady Way trail, which spans 7.2 miles and connects to the Seminole Trail outdoor recreation. Highly regarded schools and easy access to the area’s everyday amenities. With its generous living spaces, extensive updates, inviting outdoor areas and prime corner-lot setting, this Brookshire Heights home offers an exceptional opportunity to enjoy a beautifully cared-for residence in a highly desirable location.

2572 Fifeshire Drive, Winter Park
2215 Woodcrest Drive, Winter Park
$637,500
4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code
PRICE JUST REDUCED!! Nestled on a tranquil, tree-lined street in the vibrant heart of Winter Park, this reimagined 1960s mid-century modern pool residence beautifully harmonizes timeless architectural soul with stylized contemporary updates. Bathed in glorious natural sunlight, the open-concept interior unfolds beneath soaring vaulted ceilings, where durable wood-look flooring flows seamlessly across expansive living and dining spaces. At the center of it all lies a true chef’s haven—an exquisitely updated kitchen equipped with solid wood cabinetry, rich granite countertops, a sprawling prep island, sleek stainless steel appliances, and a bold over-range hood. Thoughtfully arranged along a private bedroom wing, the four spacious bedrooms blend exceptional comfort with versatile living spaces. The fourth bedroom is framed by views of the sun-drenched pool deck—an inspiring backdrop for a home office, creative sanctuary, or private gym. The primary retreat serves as a peaceful haven, complete with an elegant ensuite bath showcasing custom tile work and a glowing vanity mirror. Step through the doors into your own fully fenced tropical oasis, where quintessential Florida living takes center stage. Spend your afternoons lounging beside the sparkling swimming pool, entertaining guests from the custom Tiki bar, or relaxing with a cool drink under the shade of the gazebo surrounded by fresh, plush, mature landscaping and fresh sod. Modern convenience and major infrastructure upgrades ensure total peace of mind, featuring updated plumbing, electrical, and windows, along with a brand-new 2026 HVAC heat pump system (complete with a 10-year warranty) and a 2026 water heater. Complete with a two-car carport, dual storage rooms, indoor laundry, and a well-water irrigation system, every practical detail has been addressed. All of this is situated within top-tier school zones (Brookshire, Glenridge, and Winter Park High), just moments from the boutique shopping and dining on Park Avenue, Rollins College, Baldwin Park, Cady Way Trail, medical hubs, and the energy of downtown Orlando. Don't miss out on one of the lowest priced homes in Winter Park School district!!

2215 Woodcrest Drive, Winter Park
2119 Howard Drive, Winter Park
$3,195,000
5 Beds ⋅ 6 Baths ⋅ Timberlane SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. A striking new custom residence by FG Schaub Custom Homes, located at 2119 Howard Drive in Winter Park. This exceptional 5-bedroom, 5.5-bath home offers 4,139 square feet of beautifully appointed living space, thoughtfully designed for elevated everyday living and effortless entertaining. The dramatic two-story stone entry creates a memorable first impression, complemented by crisp stucco, dark Anderson windows, and warm, refined finishes. The handcrafted iron front door makes a statement of its own, featuring innovative electronic glass that transitions from clear to frosted at the touch of a button, offering both architectural impact and privacy. Inside, an expansive open-concept floor plan showcases soaring ceilings, abundant natural light, and seamless connections between the main living spaces. The great room is enhanced by beautifully custom coffered ceilings, adding architectural dimension and a sophisticated sense of scale while creating an inviting atmosphere for both intimate gatherings and entertaining on a larger scale. The first-floor primary suite offers a luxurious escape, featuring a spacious walk-in closet and spa-inspired bathroom designed to provide a serene retreat at the end of the day. Also on the first floor, a private guest suite with en-suite bathroom provides an ideal space for overnight guests or extended family. Three additional bedrooms and bathrooms are located on the second floor, offering exceptional flexibility for family, guests, a gym, or a home office. At the heart of the home, the gourmet kitchen combines sophisticated design with everyday functionality, featuring a large quartz island, custom cabinetry, and premium Wolf and Sub-Zero appliances. The open-concept layout allows the kitchen to flow effortlessly into the surrounding living and entertaining spaces. Designed for the quintessential Florida lifestyle, the expansive outdoor living area known as the “Transitional Room” features electric roll-away screens, a mini split, and a fully equipped summer kitchen. The adjoining pool and spa create the perfect setting for poolside afternoons, al fresco dining, and memorable evenings with family and friends. Additional highlights include an oversized two-car garage with EV charger, spray foam insulation throughout the home for energy efficiency, designer-curated finishes, and a fully fenced yard with thoughtfully designed landscaping and lighting to further enhance the home’s outdoor ambiance.

2119 Howard Drive, Winter Park
913 Moss Lane, Winter Park
$950,000
3 Beds ⋅ 2 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code
913 Moss Lane is in the Vias of Winter Park, on a tree-lined street in Maitland Shores. Neighborhood access to the Winter Park chain of lakes is a block away. Winter Park Racquet Club is a short walk. Park Avenue is a short drive. The home is zoned for Dommerich Elementary, Maitland Middle, and Winter Park High. The house is a 1953 split-level with 3 bedrooms, 2 baths, about 1,887 square feet, and a two-car garage. The main floor has the living room, dining area, kitchen, and Florida room. The bedrooms are upstairs. The 2023 renovation added new flooring, interior and exterior paint, a kitchen with white cabinetry, stone counters, and stainless appliances, and an updated bath with a walk-in glass shower. The backyard is fenced and has a patio. There is no homeowners association. This is a renovated three-bedroom in the Vias. See it for the street, the schools, and the lakes.

913 Moss Lane, Winter Park

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