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504 W Swoope Avenue, Winter Park
$1,300,000
3 Beds ⋅ 3 Baths ⋅ Vilasa Twnhms SubDv. ⋅ 32789 Zip Code
Enjoy luxury living and premium sought-after location at Vilasa Homes, the newest construction in Winter Park, FL 32789. Walk to Park Avenue lifestyle, arts and culture- a mini-version of Manhattan’s Central Park, brick streets, historic neighborhoods, area’s hottest restaurants, shopping and the prestigious Rollins College. The finishes for this 2-estory townhome personally selected by one of the nation’s top interior designers. Carefully selected design team of Nasrallah Architectural Group, Ted Maines Interiors and Jordan Builders. Alys Beach inspired incorporating wood accents, architectural stairway, wrought iron and two-story ALL block construction all steps away from downtown Winter Park. Energy-saving features such as Pella double pane windows and extra insulation. Home is prewired for surround sound, cameras, alarm system, etc. Beautifully appointed-Revwood/LVP flooring throughout from Daltile/Mohawk, recessed lights, level 4 wall finishes, 13-foot ceilings on the main floor, and 10-foot ceilings upstairs. This unit has been thoughtfully upgraded with a top modern package worth $40k. Chef’s gourmet kitchen is complete with high-end 18” flat panel cabinetry, 2.5” mitered Quartz countertops, double waterfall Quartz island, Thermador appliances, and beautiful Quartz backsplash. 6 burner Thermador SS gas cooktop, built-in butlers bar in dining room, staircase lighting are all additional upgrades. Spacious primary retreat on second floor with loft area perfect for office, Peloton or game room all wired with internet and electrical. Primary bedroom includes two separate his and hers closets with custom shelving and organizers. Generous closet and storage spaces. Relax in your garden tub and oversized walk-in shower, Quartz countertops, designer tile, Koehler fixtures/bathroom accessories and custom lighting treatments. Two more stately suites that can be used for exercise, office or bedrooms. Automated, remote window coverings. 2-car garages featuring insulated steel garage doors and additional storage. The Swoope townhomes each have an enlarged backyard measuring approx. 40ft x 20ft, including 8ft x 8ft covered patio slab which extends from the sliding doors. Each unit includes privacy fencing and landscaping. Owners maintain own backyard. Convenient and minutes from Hillstones, Whole Foods, Trader Joe's, Park Avenue restaurants and shopping! Top rated-9 hole Winter Park Golf Course, Casa Feliz, Morse Museum, water sports, Rollins, and churches are all a short stroll away.

504 W Swoope Avenue, Winter Park

7560 Aloma Pines Court, Winter Park
$365,000
3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code
Welcome to 7560 Aloma Pines Ct, a move-in-ready 3-bedroom, 2.5-bathroom townhome offering 1,866 square feet of comfortable living space in a gated Winter Park community. Built in 2016, this thoughtfully designed home offers a practical layout with plenty of space to spread out, including a primary suite conveniently located on the main floor. The kitchen features stone countertops and opens naturally to the main living areas, creating an easy flow for everyday living and entertaining. Tile and carpet flooring run throughout the home, while the attached one-car garage adds everyday convenience and storage. Step outside and enjoy the ease of low-maintenance townhome living without giving up the comfort of having your own private residence. The gated community provides an added sense of privacy, while the home's location puts you close to the shopping, dining, schools, and everyday conveniences that make the Winter Park area so desirable. Whether you're looking for your first home, a place to simplify your lifestyle, or an investment property in a convenient Central Florida location, 7560 Aloma Pines Ct offers a comfortable combination of space, functionality, and location. Move in, settle in, and enjoy everything Winter Park and the surrounding area have to offer.

7560 Aloma Pines Court, Winter Park

447 N Phelps Avenue, Winter Park
$960,000
Ethel Park SubDv. ⋅ 32789 Zip Code
An outstanding opportunity to acquire a generously sized homesite in the highly desirable Winter Park area. Measuring approximately 75' x 154', this 11,555-square-foot lot offers excellent potential for a custom luxury residence. This property is being offered for its land value, presenting an ideal opportunity for a builder, developer, investor, or buyer looking to create a custom home tailored to today's luxury lifestyle. The Winter Park area hosts a remarkable collection of luxury homes, custom estates, and continued new development, making this an attractive location for those seeking to build in an established and highly desirable market. With its generous lot dimensions and surrounding luxury development, this property provides an excellent canvas for your next custom-home project.

447 N Phelps Avenue, Winter Park

447 N Phelps Avenue, Winter Park
$960,000
2 Beds ⋅ 1 Baths ⋅ Ethel Park SubDv. ⋅ 32789 Zip Code
An outstanding opportunity to acquire a generously sized homesite in the highly desirable City of Winter Park area. Measuring approximately 75' x 154', this 11,555-square-foot lot offers excellent potential for a custom luxury residence. This property is being offered for its land value, presenting an ideal opportunity for a builder, developer, investor, or buyer looking to create a custom home tailored to today's luxury lifestyle. The Winter Park area hosts a remarkable collection of luxury homes, custom estates, and continued new development, making this an attractive location for those seeking to build in an established and highly desirable market. With its generous lot dimensions and surrounding luxury development, this property provides an excellent canvas for your next custom-home project.

447 N Phelps Avenue, 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

786 W Canton Avenue, Winter Park
$450,000
Capens Add SubDv. ⋅ 32789 Zip Code
HIGH & DRY | PRIME WINTER PARK LOCATION | BUILD YOUR DREAM HOME Rarely does an opportunity like this become available in the heart of Winter Park! This high-and-dry homesite is ideally situated in a highly desirable area surrounded by beautiful new construction homes, including a newer community of impressive million-dollar residences directly across the street. Located in coveted Old Winter Park/32789, this approximately 96' x 49' lot offers a rare opportunity to create your very own custom home in one of Central Florida’s most sought-after locations. This location offers the finest in Orange County Schools, award winning Winter Park High. Originally home to a residence years ago, this property offers an exciting opportunity to bring your favorite builder and create a home designed specifically for your lifestyle. Imagine building your own one-of-a-kind masterpiece in a neighborhood where new construction and redevelopment are transforming the area while maintaining the character and charm that makes Winter Park so special. LOCATION truly sets this property apart! Bike to Park Avenue or stroll to Winter Park Village, where premier dining, shopping, entertainment, and everyday conveniences are just minutes from your future front door. Enjoy easy access to Hannibal Square, the Park Avenue corridor, U.S. 17-92, I-4, grocery stores, specialty shops, the Winter Park Community Center and Park, Rollins College, and AdventHealth. With new construction continuing to surround the area, this is your chance to secure a piece of Winter Park before available land becomes even harder to find. Zoned R-1A and located within the desirable Winter Park area, this property offers exceptional potential for a custom residence or investment. NO HOA. Bring your imagination, creativity, and builder! If you’ve been searching for that special Winter Park homesite where location, lifestyle, and future value come together, your search may be over. This is the Winter Park sweet spot you’ve been waiting for! View Virtual tour for a live view of the street.

786 W Canton Avenue, Winter Park

540 N Pennsylvania Avenue, Winter Park
$3,950,000
4 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Rare Winter Park redevelopment opportunity on a NEARLY HALF-ACRE CORNER PARCEL JUST MINUTES FROM PARK AVENUE. Newly priced at $3,950,000, this R-3 ZONED (Medium-Density Residential) property offers outstanding redevelopment potential, INCLUDING CAPACITY FOR UP TO SEVEN RESIDENTIAL UNITS. Ideally positioned between Park Avenue and Winter Park Village, the property offers convenient access to renowned dining and shopping, Rollins College, cultural attractions, AdventHealth Winter Park, and major transportation corridors. Three existing residences occupy the site and contribute no value to the offering. Properties of this size and zoning, so close to Park Avenue, are exceptionally rare. THIS PROPERTY IS CROSS-LISTED AS VACANT LAND WITH THE MLS #O6431538.

540 N Pennsylvania Avenue, Winter Park

1431 Palm Avenue, Winter Park
$799,999
Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Welcome to this beautiful lot located in one of Winter Park’s most desirable neighborhoods. This exceptional location presents the perfect opportunity to build your dream home in one of the most sought after school zones Winter Park has to offer. Set along picturesque brick streets shaded by mature trees, the location is hard to beat. It is within walking distance to the beautiful Lake Knowles and Lake Wilbar, just minutes from Park Avenue, the Winter Park YMCA, AdventHealth Winter Park, Rollins College, the Winter Park Chain of Lakes, golf courses, and an abundance of exceptional dining and shopping. Enjoy the chance to create a home tailored to your lifestyle with a perfect blend of classic Winter Park character, beautiful outdoor living, and an unbeatable location.

1431 Palm Avenue, Winter Park

2410 Sherbrooke Road, Winter Park
$769,000
4 Beds ⋅ 3 Baths ⋅ Sherbrooke SubDv. ⋅ 32792 Zip Code
Welcome to 2410 Sherbrooke Rd in Winter Park! This spacious single-story home offers 2,141 sq ft of living space with 4 bedrooms, 2.5 bathrooms, and an attached two-car garage, all in a convenient location within walking distance of Winter Park High School. 10 minutes to Full Sail University, Rollins College, or Downtown Winter Park. Step inside to find generous living and family spaces filled with natural light, beautiful hardwood flooring, and a flexible layout designed for both everyday living and entertaining. The upgraded kitchen features granite countertops, abundant wood cabinetry, stainless steel appliances, recessed lighting, a center island, and a breakfast bar overlooking the family room. The spacious primary suite features new vinyl flooring and an updated en-suite bathroom with dual vanities and a large walk-in shower. Three additional bedrooms provide plenty of flexibility for guests, home office space, or other needs. An additional full bathroom, half bath, and dedicated laundry room complete the interior. French doors lead to the screened patio, offering a comfortable space for outdoor dining and relaxing. Beyond the patio is an exceptionally large backyard surrounded by mature trees and landscaping, with plenty of room for gardening, recreation, entertaining, or creating your own outdoor retreat. Major improvements include a ROOF REPLACED IN 2022 and A/C REPLACED IN 2022, giving the next owner added peace of mind. With its upgraded kitchen and bathrooms, spacious floor plan, beautiful flooring, huge backyard, screened patio, two-car garage, and recently replaced major systems, this Winter Park home offers an outstanding combination of space, comfort, and location. Schedule your private showing today and discover everything this home has to offer!

2410 Sherbrooke Road, Winter Park

1256 S Pennsylvania Avenue Unit 9, Winter Park
$950,000
3 Beds ⋅ 3 Baths ⋅ Casa Jardin Condo SubDv. ⋅ 32789 Zip Code
Positioned in Winter Park’s Virginia Heights neighborhood, just moments from Park Avenue and Seven Oaks Park, this Mediterranean-inspired townhome-style condominium offers three bedrooms, two and a half baths and nearly 2,000 square feet of conditioned living space. A rare private driveway, gated entry and paver walkway establish a distinct sense of arrival, while wrought-iron details introduce the architectural character found throughout the residence. Inside, soaring ceilings, arched openings, column-lined corridors, solid wood interior doors and custom cabinetry and built-ins create a richly detailed interior. The main living area features wood flooring, coffered ceilings, designer lighting and a gas-burning fireplace, with a living room ceiling rising more than 17 feet. An open layout connects the living and dining areas to the kitchen, appointed with solid wood cabinetry, granite countertops, island seating for two, Sub-Zero refrigeration, an undercounter wine refrigerator and a Wolf four-burner gas range. French doors open to a screened private atrium with paver flooring and water feature, extending the living space for alfresco dining and entertaining. The primary suite incorporates cathedral and barrel-vaulted ceiling details, cove lighting, crown molding, a private balcony and dual walk-in closets. Its spa-style bath includes a jetted tub, multi-head shower, split vanities with makeup space and private water closet. Two additional bedrooms are thoughtfully separated from the primary suite. One features a built-in desk, while another offers vaulted ceilings and a Juliet balcony. An in-residence elevator provides access between levels, complemented by a distinctive wrought-iron spiral staircase leading toward the third-floor rooftop terrace. Adjacent conditioned bonus space (not included in the stated conditioned square footage) provides flexible space with finished storage and convenient access to HVAC and elevator equipment. Additional features include plantation shutters, custom window treatments, motorized sheer shades, central vacuum and a Control4 system integrating music throughout indoor and outdoor spaces with networking, security and climate controls. The two-car garage includes an epoxy-finished floor and new garage door opener, and the residence has a new HVAC system. Casa Jardin recently completed an exterior refresh including a new roof and exterior paint. Residents also enjoy access to Lake Virginia and the Winter Park Chain of Lakes via College Point, with a lakefront area and kayak and paddleboard storage. Set within Virginia Heights, the residence offers convenient access to Azalea Park, the Winter Park Tennis Center, Orange Avenue dining and boutiques and Park Avenue, supporting an easy lock-and-leave Winter Park lifestyle. The residence may also be purchased turnkey furnished for additional consideration.

1256 S Pennsylvania Avenue Unit 9, Winter Park

822 Symonds Avenue, Winter Park
$599,999
Capens Add SubDv. ⋅ 32789 Zip Code
Build in the heart of Winter Park. This cleared quarter-acre lot (approx. 10,807 sq ft, 50' x 216') sits on Symonds Avenue on the city's west side. It's just blocks from Hannibal Square, Winter Park Village and Martin Luther King Jr. Park, and minutes from the shops and restaurants of Park Avenue. The lot is ready for your plans. It's cleared, with mature shade trees, a paved street with sidewalk, and public water and sewer available. It's zoned R-2, in Flood Zone X, with no HOA. Builders and buyers have room to create a custom home or an investment project in one of Central Florida's most desirable cities. Land this close to Park Avenue rarely comes available. Buyer to verify zoning, setbacks and permitted uses with the City of Winter Park.

822 Symonds Avenue, Winter Park

2260 Mulbry Drive, Winter Park
$1,925,000
5 Beds ⋅ 4 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. Pre-Construction. To be built. Your Dream Home Is Ready To Be Built!! Pre-Construction Opportunity! Build-to-Suit! Buyers who act now can still pick finishes and style! Build your custom dream home with renowned Konkol Homes in one of Central Florida’s most desirable areas! This nearly 1/4-acre lot is perfectly situated near Baldwin Park, East End Market, Audubon Park K-8, Rollins College, and Advent Health. The stunning Transitional Modern design features 3,246 sq. ft. of living space, offering 5 bedrooms, 4 baths, and a loft. The first-floor primary and guest suites provide convenience and privacy, while the Chef’s Kitchen flows seamlessly into the oversized Gathering Room in this open-concept design. The second floor includes three additional bedrooms, two with walk-in closets, and a spacious loft. Enjoy the benefits of a No HOA community in a well-established neighborhood, all while staying close to Baldwin Park and Minutes to Downtown Orlando! Enjoy Winter Park’s vibrant events and amenities! Zoned for top-rated schools of Audubon K-8 and Winter Park High School! This is your opportunity to build your dream Oasis and enjoy the Florida lifestyle! Buyer can participate in build out if placed under contract prior to construction start.

2260 Mulbry Drive, Winter Park

2260 Coldstream Drive, Winter Park
$675,000
4 Beds ⋅ 2 Baths ⋅ Brookshire Heights SubDv. ⋅ 32792 Zip Code
Virtually Staged. Zoned for Fantastic Winter Park Schools, this 4 bed, 2 bath recently renovated abode is waiting for you. Located on a quiet, tree-lined street, you can walk to highly rated Brookshire Elem and Winter Park High. The open-plan living space has beautiful travertine tile floors flowing through the kitchen, dining room, and living room. Renovated in 2026, the kitchen offers quartz counter tops, new appliances, under cabinet lighting, custom tile backsplash, and pendant lights. Flowing from the kitchen to the dining room and through to the living room, this open floor plan is sure to please. Double French doors open from the sunny living room to the spacious backyard. The oversized two-car garage and laundry room are just off the kitchen. Travertine continues down the hall, while all 4 bedrooms have newly installed wood flooring (2024). The primary bedroom has a renovated ensuite (2026) with enlarged walk-in shower, custom tile, new fixtures, and new quartz topped vanity. All 4 bedrooms have window shutters and new ceiling fans, and the renovated hall bath (2025) offers new quartz topped double sink vanity, new mirrors, and tub/shower tile surround. Out back, the grassy backyard with new fencing and St Augustine sod (2025) offers plenty of room for kids and pets to play or even a future pool addition. Located just 3 miles to Rollins College and the Park Ave shopping and dining district, this prime location offers other, even closer, benefits. Cady Way Park is 2 blocks away with a community pool, pickleball courts, tennis courts, picnic tables, and access to the Cady Way Bike Trail. NEW HVAC 2024, Roof 2015, updated electrical box 2014, and house re-piped with CPVC 2009. Come check out this charming move-in ready Winter Park house and make it your own home.

2260 Coldstream Drive, Winter Park

2136 Linden Road, Winter Park
$365,000
3 Beds ⋅ 2 Baths ⋅ Ridge High Sub SubDv. ⋅ 32792 Zip Code
Welcome home to Winter Park! This beautifully renovated 3-bedroom, 1.5-bath home offers the perfect combination of classic Florida living and extensive modern updates. Much of the hard work has already been done—just bring your furniture and start enjoying your new home! New luxury vinyl plank flooring throughout, fresh interior paint, and a bright, refreshed feel. The renovations go well beyond what you can see, including new electrical wiring and electrical panel, new plumbing, and a new HVAC system—major improvements that add comfort and peace of mind for years to come. The exterior has also been freshly painted, giving the home a clean and inviting appearance. And then there’s the backyard! This fabulous oversized outdoor space offers plenty of room to create your own Florida retreat. Add a swimming pool, outdoor kitchen, garden, play area—or perhaps all of the above. There’s room to dream! Located in the highly desirable City of Winter Park. Come take a look—you may have just found the Winter Park home you’ve been waiting for!

2136 Linden Road, Winter Park

436 N Wymore Road, Winter Park
$1,350,000
Killarney Circle SubDv. ⋅ 32789 Zip Code
Prime Winter Park commercial office building with visibility of monument signage from 1-4 East bound traffic and Ideally situated on Wymore Road. This 2018 built one story office building offers Low-maintenance ownership, with approximately 3021 total square feet, creating a professional office environment with flexible layout options for investors or owner-users. The property features 10 parking spaces includes one handicap with public street parking option located in 32789. Both suites have separate entrances, with access door in between, both with reception areas, open air built-in workspaces. Each suite has its own kitchen and bathroom facilities. Building has 6 total private offices, ( 4 & 2) providing convenience for both administrative and operational functions. Well-constructed, high ceilings, attractive flooring, 2 conference rooms with high-end lighting fixtures, window treatments. Both suites are leased, generating $9,678.60 per month with the tenants' paying utilities, alarm, housekeeping, building taxes, and insurance. One of the tenants' leases (1736 Sq foot suite) expires September 1, 2029 (rental income increases every year) The other suite (1285 sq ft) lease is owner occupied and available for rent immediately or owners are willing to stay up for up to seven months based on new owners' situation. This property offers an excellent opportunity for an owner-occupant of one suite while obtaining rental income. The property manager is the listing RE Agent/seller who will provide a smooth transition upon closing. This property is a prime opportunity for businesses seeking a high-quality, move-in-ready or flex space in one of the area's most accessible commercial corridors.

436 N Wymore Road, Winter Park

200 S Interlachen Avenue Unit 350, Winter Park
$2,350,000
3 Beds ⋅ 4 Baths ⋅ Versailles Winter Park Condo SubDv. ⋅ 32789 Zip Code
Welcome to The Versailles of Winter Park, an extraordinary opportunity to own one of only seven exclusive private residences in one of Winter Park's most coveted luxury communities, nestled just steps from the world-renowned Park Avenue and adjacent to the prestigious Alfond Inn & Spa. This magnificent third-floor residence offers 3,110 square feet of impeccably designed one-level living, oak hardwood floors throughout, elegant crown molding, and an abundance of natural light pouring through French doors set the tone for refined sophistication. Entertain effortlessly in the grand living area with a sprawling balcony adorned with Chicago brick and stone railing. Kitchen includes wood cabinet, granite, Monogram refrigerator, convection oven and microwave. The versatile split-bedroom floor plan ensures ultimate privacy, with the lavish primary suite accessed through double doors, walk-in closet, private balcony access, and an opulent spa bath featuring dual vanities, a soaking tub, walk-in shower. A designated office with wall-to-wall built-ins, a formal dining room accommodating up to twelve guests, a private two-car garage, and meticulously maintained landscaping. The Versailles of Winter Park is the ultimate expression of luxury living offering an unparalleled lifestyle just moments from the finest dining, boutique shopping, art festivals, and cultural events that makes Winter Park one of Florida's most desirable destinations.

200 S Interlachen Avenue Unit 350, Winter Park

2626 Ambergate Road, Winter Park
$380,000
3 Beds ⋅ 1 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
Mid-century style meets modern convenience in this beautifully updated Winter Park home, offering a move in opportunity with no HOA. Extensively improved since 2022, the home features refinished terrazzo floors, a full repipe, updated electrical panel, new water heater, new roof with fascia and soffit, gutters, new garage door, and a renovated open kitchen with dual induction burner and beautiful cabinetry. Additional improvements include new fencing, exterior and interior paint, drainage enhancements, new sidewalk and stepping stones, updated lighting and ceiling fans, and more. Side yard access allows ample space for boat, trailer, etc. Additional storage in the 1.5 car oversized garage. This home has been meticulously updated with love, and the sellers will contribute $10,000 towards closing costs, interest rate buy down, or home updates. Ideally located near the Winter Park YMCA, Baldwin Park, dog park, local hospitals, and zoned for Winter Park High School. Enjoy easy access to Park Avenue, with its exceptional restaurants, shopping, and charming downtown atmosphere just minutes away.

2626 Ambergate Road, Winter Park

2275 Island Run, Winter Park
$299,990
3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code
Great opportunity in the established Windward Square community of Winter Park! This END-UNIT home offers 3 bedrooms, 2 full bathrooms and approximately 1,467 square feet of living space, with added privacy and plenty of potential. ROOF REPLACED IN 2017! 10K seller contribution for the floor. The home is ready for some TLC and personal updates, giving the next owner the opportunity to renovate and make it their own. The spacious living and dining areas gives a functional layout, while the large screened porch provides additional space to relax, entertain, and enjoy Florida living. Being located at the end provides additional privacy and a more open feel compared with interior units. The community offers amenities including a swimming pool and tennis courts. Conveniently located near shopping, dining and major roadways, with easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this property offers great potential and an excellent opportunity to add value through your own improvements. Bring your vision and make this home your own!

2275 Island Run, Winter Park

508 Brechin Drive, Winter Park
$629,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code
Completely renovated and move-in ready, this beautifully updated Winter Park home offers a fresh, modern interior without the hassle of renovations. The brand-new kitchen features new cabinetry, quartz countertops and all new appliances, while both bathrooms have been fully renovated with new finishes and fixtures. New luxury vinyl plank flooring runs throughout the home, complemented by fresh interior paint. The roof was replaced in April 2022, providing added peace of mind for today's buyer. With 3 bedrooms, 2 bathrooms and approximately 1,785 square feet of living space, this home offers a comfortable and functional floor plan in an established Winter Park location. The spacious yard offers plenty of room for outdoor enjoyment and the opportunity to create your own ideal landscaping. Enjoy easy access to Cady Way Park and the Cady Way Trail, perfect for walking, biking and recreation. Just minutes from the restaurants, shopping and charm of Park Avenue, as well as the popular Baldwin Park area. Conveniently located near AdventHealth Winter Park and numerous dining, shopping and recreational options. Agent owned property.

508 Brechin Drive, Winter Park

7839 University Garden Drive, Winter Park
$1,000,000
Harbor East SubDv. ⋅ 32792 Zip Code
REMARKABLE LAND OPPORTUNITY IN WINTER PARK! Welcome to an exceptional real estate offering situated on 4.93 level, usable acres in the highly desirable Winter Park area (Zip Code 32792). This unique property features both an existing mobile home and a separate concrete block home, presenting an incredible value-add situation for investors, developers, or buyers looking for a place to live while planning their next big project. The vast, cleared land is the ultimate blank canvas, perfect for building your custom luxury dream home, establishing a family compound, or exploring potential multi-family development opportunities (subject to Orange County zoning and approvals). Location is everything, and this property delivers: you are just minutes from the University of Central Florida (UCF), premier shopping centers, major dining, Orlando International Airport (OIA), and all the world-class entertainment that the greater Orlando area has. Whether you want a private sanctuary with acreage, a rental income generator, or a strategic land hold with high future upside, this rare find checks every box. Do not miss out on this extraordinary piece of Central Florida real estate!

7839 University Garden Drive, Winter Park

1320 Orchid Avenue, Winter Park
$1,350,000
4 Beds ⋅ 4 Baths ⋅ Elizabeth Heights Sub SubDv. ⋅ 32789 Zip Code
Modern Winter Park living meets exceptional convenience at this beautifully designed 2023 residence, ideally positioned near Park Avenue and just minutes from Downtown Orlando. Offering nearly 3,000 square feet of thoughtfully designed living space, this 4-bedroom, 4-bath home combines contemporary architecture, abundant natural light, and elevated finishes in one of Central Florida’s most sought-after locations. Oversized windows and an open-concept layout create a bright, seamless connection between the living, dining, and kitchen spaces—equally suited for everyday living and entertaining. At the heart of the home, the gourmet kitchen features premium stainless steel appliances, custom cabinetry, designer backsplash and lighting, and an oversized island with dramatic waterfall-edge quartz countertops and generous seating. The thoughtfully designed floor plan includes a first-floor guest suite and full bath, providing privacy and flexibility for overnight guests, multigenerational living, or a private home office. Upstairs, the spacious primary retreat features a spa-inspired bath with dual vanities, soaking tub, oversized walk-in shower, and a generous walk-in closet enhanced with a custom organization system. Two additional bedroom suites complete the second level. Outside, the fully fenced backyard and covered lanai with summer kitchen create an inviting extension of the home’s living space—perfect for outdoor dining and entertaining year-round. Additional highlights include designer LED lighting, abundant storage, a two-car garage, manicured landscaping, and no HOA. Located near shopping, dining, highly rated schools, Park Avenue, and the best of Winter Park and Orlando, 1320 Orchid Avenue offers the rare opportunity to enjoy newer construction, modern design, and an exceptional location without sacrificing space or privacy. Schedule your private showing today.

1320 Orchid Avenue, Winter Park

1850 Bryan Avenue, Winter Park
$725,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code
Tucked beneath mature oak trees, 1850 Bryan Avenue is a well-maintained home offering comfortable single-story living in Winter Park. Natural light and warm wood floors flow through the inviting living and dining spaces, while a flexible bonus room is well suited for a home office, den or creative space. The kitchen features wood cabinetry and ample counter space. The spacious primary suite offers a private retreat. Additional features include an indoor laundry room and an attached two-car garage. Outside, the fenced yard provides a peaceful setting for gardening, entertaining or relaxing beneath the trees. With shopping, dining, parks and other Winter Park amenities nearby, this home brings together character, comfort and a desirable location.

1850 Bryan Avenue, Winter Park

443 Broadview Avenue, Winter Park
$999,000
4 Beds ⋅ 3 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code
A truly special property in Winter Park’s 32789 zip code, this renovated 1925 Craftsman is filled with character and charm. Set on an oversized 0.36-acre lot just one home from Lake Killarney, the property is 2803sf, with a 3/2 main residence (approximately 2200sf) plus a detached 1/1 guest cottage (approximately 600sf). Beautiful curb appeal and a glass-enclosed front porch with beadboard ceiling welcome you into the home. The original piano, which has been in the house since it was built, adds to its rich history and charm. Great layout for entertaining, with multiple sitting areas and an open floor plan with a dining room that flows to the family room and kitchen, all flooded with natural light and numerous windows and French doors. The kitchen offers bar seating, granite countertops, custom cabinetry and storage, stainless steel appliances, a natural-gas cooktop, glass tile backsplash, and tall ceilings. Glass French doors open to a brick patio and a walkway leading to the guest cottage. The two back bedrooms share a Jack-and-Jill bathroom, and the front bedroom with an adjacent hall bath connects to the enclosed sunroom, perfect for a nursery, office, or den. Additional details include original oak floors, crown molding, glass doorknobs, designer lighting, interior laundry with a new washer and dryer, and an upgraded security system. The expansive backyard features mature landscaping and ample space for outdoor enjoyment, with potential for a future pool. The metal-roofed carport includes a ceiling fan and string lights, and Lake Killarney is visible from several areas of the property. The guest cottage includes one bedroom, one bathroom, a living room, and a full kitchen—ideal for guests, extended family, a home office, or as a potential income-producing property. Recent improvements include the main-house roof in 2020; guest-cottage roof in 2022; two new guest-cottage A/C units installed in March 2023; security system in 2023; PVC water line and irrigation pump in 2024; main-house washer and dryer in June 2026; and exterior paint in August 2026. Additional updates include kitchen appliances, lighting and hardware, landscaping and irrigation system with well, interior paint, and a transferable termite bond. Conveniently located within easy walking distance of Hillstone, Trader Joe’s, numerous shops and restaurants, and quick access to I-4. All room dimensions, home & guest cottage square footage, and land square footage are approximate. Buyer to verify.

443 Broadview Avenue, Winter Park

7530 Cranes Creek Court, Winter Park
$309,900
3 Beds ⋅ 3 Baths ⋅ Cranes Crk SubDv. ⋅ 32792 Zip Code
Welcome home to this inviting 3-bedroom, 2.5-bath townhome offering a comfortable floor plan and several recent updates. All three bedrooms are conveniently located on the second floor and feature newly installed carpet, providing a fresh and comfortable feel. The main living areas feature easy-care ceramic tile throughout the living room and dining room, as well as in the bathrooms. The kitchen is equipped with new appliances, including a range/oven, dishwasher and microwave, making it ready for its next owner. An interior laundry area conveniently located near the kitchen helps make everyday chores a little easier. The interior has also been recently painted, giving the home a clean, refreshed appearance. Sliding glass doors from the dining room lead directly to the patio, providing a great spot for morning coffee, outdoor dining or simply enjoying some fresh Florida air. An attached one-car garage provides the added convenience of covered parking and additional storage. With new carpet, fresh interior paint, new kitchen appliances and a functional 3-bedroom layout, this townhome is ready for you to make it your own. Schedule your showing today!

7530 Cranes Creek Court, Winter Park

5108 Lazy Oaks Drive Unit 5108, Winter Park
$269,000
2 Beds ⋅ 2 Baths ⋅ Lazy Oaks Condo SubDv. ⋅ 32792 Zip Code
Welcome to 5108 Lazy Oaks Drive, a 2-bedroom, 2-bathroom condo in a desirable Winter Park location. This light-filled home has approximately 1,008 square feet of comfortable living space with a functional floor plan, abundant windows, skylight and sliding glass doors that bring in plenty of natural light. The spacious living room features a beautiful brick fireplace and sliding glass door access to the screened-in back patio. The patio can also be accessed directly from the primary bedroom, creating a wonderful private outdoor space to enjoy your morning coffee, relax, or entertain. The primary suite features an en-suite bathroom with a walk-in shower, spacious two-sink vanity, and plenty of closet space. The guest bedroom is conveniently located just two steps from the second full bathroom, providing an ideal setup for family, guests, or a home office. The well-maintained original kitchen includes an electric range and oven, refrigerator, dishwasher, and two-basin stainless steel sink. Well-maintained tile flooring runs throughout the home, offering durability and easy maintenance. The spacious one-car garage has more than just parking, with a washer and dryer and plenty of additional storage space. The HOA fee is $277 per month and includes lawn maintenance and responsibility for the entire exterior of the condo, including the roof, providing added convenience and peace of mind for the homeowner. With its fresh interior, abundant natural light, brick fireplace, screened-in patio, private primary suite, attached garage, and low-maintenance lifestyle, 5108 Lazy Oaks Drive is a wonderful opportunity to own a comfortable home in Winter Park.

5108 Lazy Oaks Drive Unit 5108, Winter Park

1259 Indiana Avenue, Winter Park
$575,000
2 Beds ⋅ 3 Baths ⋅ Townhomes/Harper Place SubDv. ⋅ 32789 Zip Code
Virtually Staged. WINTER PARK, WITHIN REACH. A rare opportunity to step into one of Central Florida’s most coveted lifestyles. Bright, airy, remarkably spacious, this immaculate 2-bedroom townhome lives far larger than its approximately 1,600 sq.ft.suggests. Greet the day with a sunny disposition as morning light fills the oversized, east-facing primary bedroom. Step onto the private lanai with a latte, stretch into a little yoga, admire a garden of your own making. With plenty of room for herbs, vegetables & flowers—a quiet little corner of Winter Park to make entirely your own. Inside, real wood floors set a warm, welcoming tone throughout a surprisingly generous collection of living spaces. Formal living & dining rooms transition into an open kitchen w/island seating, breakfast area & family room, all with views toward the lanai & garden beyond. An immaculate townhome that lives large * Upstairs, a sense of space continues w/2 large primary suites. One features a a steeping tub, the other a shower, creating flexibility for guests, roommates, multigenerational living, or substantial home office beautifully accommodating overnight guests. Carpet is immaculate, but if your vision calls for something else, a $5,000 flooring credit is offered to make the space your own * Then step outside your front door. discover why Winter Park remains one of Central Florida’s most coveted communities. Michelin-acclaimed dining & AdventHealth’s primary medical campus within walking distance. Parks & green spaces surround you, while nearby Loch Haven Cultural Park puts the Orlando Museum of Art, Orlando Science Center and an extraordinary collection of theatrical & cultural venues practically in your backyard * Minutes away, celebrated Park Avenue & historic Hannibal Square invite you to linger over lunch at a sidewalk café, browse boutiques & galleries, meet friends for dinner, or simply wander beneath the canopy of one of Central Florida’s most beautiful communities. Saturday mornings are for the farmers market. Spring brings the nationally renowned Winter Park Sidewalk Art Festival. Central Park is an extension of the community’s backyard, while lakes, museums, theaters, restaurants & tree-lined streets create an unmistakable sense of place making Winter Park one of Florida’s most enduringly desirable addresses. When you’re ready to venture farther, leave the car behind. Rail connections put Downtown Orlando & Central Florida within easy reach, Brightline opens the door to West Palm Beach, Boca Raton, Fort Lauderdale & Miami.Amtrak connects Winter Park to destinations along the East Coast. Then come home. Fire up the grill, pull up a stool at the kitchen island, or settle into the family room for the game. With open views to the lanai & garden, you can keep an eye on the score—and watch the grill master sweat it out outside without missing a play. Dinner moves easily from kitchen to table to lanai. Stay outside for a glass of wine, enjoy the garden as evening settles in, then retreat upstairs to one of 2 wonderfully oversized primary suites. Even the practical details exceed expectations: a true two-car garage with a 220V outlet ready for EV charging, a substantial built-in storage system designed to handle everything you want to keep neatly tucked away. This isn’t simply an immaculate home. It’s an attainable doorway into the Winter Park lifestyle—a home that lives large, in a location that lets you live even larger. Click on the Virtual Tour to get the full picture

1259 Indiana Avenue, Winter Park

471 Holt Avenue, Winter Park
$950,000
4 Beds ⋅ 3 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Exceptional Winter Park Opportunity with In-Law Suite & Income Potential. THIS HOUSE IS AVAILABLE FOR LEASING OPTION. Discover the opportunity to own a versatile property in one of Central Florida’s most desirable locations. 471 Holt Ave. in Winter Park offers buyers something increasingly valuable: flexibility. With a private in-law suite, this property presents an exciting opportunity for multigenerational living, a guest suite, home office, or potential rental income. For homeowners, the additional living space provides the freedom to accommodate family members or guests while maintaining privacy and separation. For investors, the configuration creates the potential to generate supplemental income, subject to applicable local regulations and requirements. The property’s location adds to its appeal, placing you near Winter Park’s renowned dining, shopping, parks, cultural attractions, and vibrant community amenities. Also, just a short distance to Rollins College! Whether you’re looking to offset your mortgage, create an additional income stream, or simply secure a property with adaptable living options, this home offers a compelling combination of lifestyle and investment potential. Opportunities with this level of flexibility are hard to find. Live in the main residence, utilize the suite for family or guests, or explore its income-producing potential. 471 Holt Ave. offers the versatility today’s buyers are looking for and the potential long-term value investors appreciate. Don’t miss the opportunity to make this flexible Winter Park property your next home or investment.

471 Holt Avenue, Winter Park