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$299,900
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code
Charming 4-bedroom, 2-bath single-story home in the established Eastbrook neighborhood of Winter Park. Built in 1959 and situated on a 0.19-acre lot, this home features an open living and kitchen area with vaulted ceilings and wood-look laminate flooring. The kitchen offers stainless steel range and microwave, tile countertops, and tile backsplash. All bedrooms feature carpet and ceiling fans, with the primary suite offering an en-suite bath with a walk-in tiled shower. Enjoy the covered back patio and fully fenced backyard. Roof is approximately 5 years old. Interior laundry closet. Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High.

3484 Seagrape Drive, Winter Park
$1,095,000
4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Some houses impress you. This one welcomes you. A fully remodeled Victorian in Winter Park, reimagined from top to bottom and minutes from Park Avenue shopping and dining. The kitchen is the heart of it all, wrapped in Calacatta Viola quartz with a full height backsplash, cabinet lighting that glows after dark, and all new Bosch appliances. The open first floor flows naturally from kitchen to dining to living, anchored by a fireplace made for slow evenings, and new engineered hardwood flooring runs throughout the entire house. All 3.5 baths are completely redone with marble floors, designer tile, and brass fixtures, including a first floor half bath with wall paneling and a one of a kind vanity that stops people mid tour. This remodel went beyond the pretty parts. A brand new roof covers the entire house and detached garage, all outlets and switches were replaced throughout, and the plumbing was redone for the kitchen and all bathrooms. The water heater is new, and the laundry room has a new stacked washer and dryer too. You move in and live, nothing to fix, nothing to update. Upstairs and down, every bedroom is spacious and has custom built in closet systems, and the stairway shows off custom oak newels and handrails with black metal balusters. Outside, the charm continues with a herringbone brick-tile front porch, balconies and back porch made for morning coffee, fresh paint inside and out, new landscaping, a new paver driveway, and a detached two car garage with a newly stained concrete floor. This is not a quick flip. Every finish was chosen with intention, and every detail was completed with care. 4 bedrooms, 3.5 baths, 2,135 sq ft of living space on a 7,151 sq ft lot, in one of Winter Park's most loved pockets. This is a home you will feel from the first moment you walk in.

1517 Harmon Avenue, Winter Park
$750,000
Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
Prime Winter Park builder and luxury custom home opportunity with rare dual access! Nestled in this Winter Park enclave just one block from the Via Streets, this location offers a massive competitive advantage and features a dedicated rear easement providing direct vehicle or construction access to the adjacent side street (Sunset). Whether you are an investor looking for a high-end project or designing your private sanctuary, this unique dual-access point is a designer’s dream—opening up incredible architectural flexibility, private rear-loading/garage options, or seamless construction staging. The property boasts an unobstructed view of the serene park setting at the intersection of Chestnut and Sunset, providing a picturesque backdrop for custom luxury home architecture. Surrounding properties are rapidly redeveloping into spectacular modern estates. Bring your custom builder and your vision to claim one of Winter Park's unique footprints. Property is being sold As-Is with value in the land. One car garage at rear of property with access thru deeded easement. Shed next to garage.

1421 Chestnut Avenue, Winter Park
$249,000
3 Beds ⋅ 3 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Virtually Staged. Don't miss this incredible opportunity in one of Winter Park's most desirable locations! This spacious 2-story condo offers over 1,700 square feet of living space, featuring an open floor plan that's perfect for everyday living and entertaining. A dedicated office space adds flexibility for remote work or a home study a rare find at this price point. While the home could use some updating, the bones and layout make this a fantastic canvas to add your personal touch and build instant equity. Currently occupied by a great tenant, this property is a perfect turnkey opportunity for investors looking to add a cash-flowing asset to their portfolio, or for buyers ready to move in once the lease ends on June 2027. With its unbeatable location near Winter Parks shopping, dining, and entertainment, this is the kind of opportunity that won't last long at $249,000. Don't miss this and make your appointment today!

2463 Grand Teton Circle Unit 2463, Winter Park
$439,900
3 Beds ⋅ 2 Baths ⋅ Tanglewood Rep SubDv. ⋅ 32792 Zip Code
FABULOUS WINTER PARK LOCATION!!! This 3 BEDROOM, 2 BATH, 1873sf CONCRETE BLOCK HOME represents QUALITY FROM THE PAST, and is CENTRALLY LOCATED in the heart of Winter Park. You can walk to the Winter Park YMCA or Interlachen Golf and Country Club, while the exclusive shoppes and restaurants on Winter Park’s famed “Park Avenue” are just 5 minutes away as well as Central Park, Rollins College, and Advent Health’s Winter Park Hospital. Nestled among several “million-dollar homes” and just two houses away from the gated “Reserve at Interlachen” community, this property has high potential! From the moment you enter, you will notice pride of ownership in the classic décor and cleanliness. The Kitchen features two breakfast bars, one of which is a pass-thru to the living room, along with copious (25) light birch cabinetry with roll out shelving and undermount lighting. The 19’ by 12’ Kitchen opens to a 10’x12’ Dinette area which opens to the living room. There is also a separate and formal 11’x12’ Dining Room. The expansive 31’x18’ Living Room features a dramatic wood-burning fireplace with a mantle and hearth encased in a beautiful brick accent wall which also houses built-in shelving and cabinetry. Sky lights serve to bring in an abundance of natural light. The Primary Bedroom is En Suite. The Guest Bathroom has been renovated with granite counters, decorative inset tile in the tub area, and updated fixtures. Additional features of this home include an attic fan, recently replaced hurricane rated garage door and opener, newer exterior electrical box (interior electrical box will be replaced prior to closing), a 10’x20’ screened porch, a .22-acre lot with a fully fenced back yard and single gate access on each side of the home. The entire house has been ripped, and the roof is less than 8 years old. Don’t miss this opportunity to live in the heart of Winter Park! Call us today for your private showing!

1818 Dover Road, Winter Park
$2,190,000
4 Beds ⋅ 3 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code
A rare opportunity awaits to own a slice of paradise on Lake Spier in beautiful Winter Park! Set on over two acres and surrounded by mature landscaping, this stunning property offers a secluded setting that feels worlds away, while world-class dining and shopping, trails and parks, and the vibrant Village Center of renowned Baldwin Park are just moments from your door. Inside, you'll find luxury finishes and appliances, expansive hurricane-impact windows, all-new HVAC and a whole-house water filtration system, along with double master suites with vaulted ceilings and distinctive architectural details throughout. Step outside, where 158 feet of lakeshore and your private dock invite you to enjoy the water at its best, from boating and waterskiing to beautiful sunrises and sunsets on the water. With approximately 3,400 square feet, four bedrooms, three baths, a detached garage/workshop and no HOA, this is a truly unique offering in one of Winter Park's most desirable locations.

1803 Barker Drive, 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
$750,000
3 Beds ⋅ 1 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
Prime Winter Park builder and luxury custom home opportunity with rare dual access! Nestled in this Winter Park enclave just one block from the Via Streets, this location offers a massive competitive advantage and features a dedicated rear easement providing direct vehicle or construction access to the adjacent side street (Sunset). Whether you are an investor looking for a high-end project or designing your private sanctuary, this unique dual-access point is a designer’s dream—opening up incredible architectural flexibility, private rear-loading/garage options, or seamless construction staging. The property boasts an unobstructed view of the serene park setting at the intersection of Chestnut and Sunset, providing a picturesque backdrop for custom luxury home architecture. Surrounding properties are rapidly redeveloping into spectacular modern estates. Bring your custom builder and your vision to claim one of Winter Park's unique footprints. Property is being sold As-Is with value in the land. One car garage at rear of property with access thru deeded easement. Shed next to garage.

1421 Chestnut Avenue, Winter Park
$530,000
4 Beds ⋅ 4 Baths ⋅ Monroe SubDv. ⋅ 32792 Zip Code
Duplex on Two Separate Lots with No HOA! Excellent opportunity for an investor or owner-occupant! This 2-bedroom, 2-bathroom duplex offers flexibility with each unit situated on its own separate lot and no HOA. One unit is currently tenant occupied, providing immediate rental income, while the second unit is vacant and ready for a new tenant or owner-occupant. The vacant unit features an updated kitchen, giving it a fresh, move-in-ready feel. The property has also been freshly painted on the exterior, enhancing its curb appeal and making it ready for its next owner. With two separate lots, an existing income-producing unit, a vacant updated unit, and no HOA, this property offers multiple possibilities for a buyer looking to add to a rental portfolio, live in one side while renting the other, or explore the advantages of the property's existing separate lot configuration. Highlights include: 2 bedrooms and 2 bathrooms in each unit, two separate lots, one occupied income-producing unit, one vacant unit with an updated kitchen, freshly painted exterior, and no HOA. A versatile Central Florida investment opportunity with immediate income and plenty of potential!

167 Jergo Road, Winter Park
$427,000
4 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 06 SubDv. ⋅ 32792 Zip Code
LOCATION! LOCATION! Winter Park property located in Seminole County. Proximity to Rollins, Full Sail, UCF, and Valencia colleges. Great income producer, with "Flex Space" as a two income rental or live on one side and rent the other. Main area has 3 bedrooms and 2 full baths, flex space has a private entrance, 1 bedroom and full bath, kitchenette, and it's own laundry area. Two driveways and parking pad for your use. Great side and separate rear yard, with lard storage shed, Home was recnently updated, with fresh paint, granite countertops, shaker cabinets, updated bathrooms, new windows, new mini-splits in flex space and tankless water heater. Fully fenced in backyard and mature trees. Plumbing has already been updated to PEX, cast iron wasteline has been updated to PVC. New flooring in main house, new baseboards installed, and freshly painted. MOVE IN READY!

1386 Clematis Lane, 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
$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
$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
$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
$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
$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
$825,000
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
$789,000
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
$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
$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
$1,250,000
32792 Zip Code
Prime Investment Opportunity on Aloma Avenue! Fully occupied strip plaza featuring five established tenants, offering immediate rental income and strong investment potential. Ideally located on Aloma Avenue in the desirable Winter Park/Orlando area, with excellent visibility, convenient access, and a strong surrounding residential and commercial base. This property provides the opportunity to generate income from day one without the hassle of finding tenants. A great addition to any investor?s portfolio?don?t miss this well-located, income-producing commercial property.

7448 Aloma Avenue, Winter Park
$699,000
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
$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
$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
$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
$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
$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! 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
$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
$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
$360,000
4 Beds ⋅ 3 Baths ⋅ Ridge High Sub SubDv. ⋅ 32792 Zip Code
Solid, mid-century modern house for growing family, in need of a little love, located in a quiet Winter Park neighborhood. HUGE backyard, with large covered open patio. One of the largest lots in the subdivision, with best configuration for possible growth opportunities. Mature trees in peaceful, fully fenced backyard. 4 bedroom, 2.5 bath with a split floor plan. Also, a possible redevelopment opportunity for builders and investors. New roof 2025, new HVAC system 2020, new water heater 2024, upgraded electric panel, re-piping of water system with Pex in 2010. Terrazzo and concrete flooring. Priced as-is for buyer to provide own upgrades. Located in Seminole County, just minutes from downtown Winter Park, YMCA, hospital, Rollins, Full Sail and UCF universities. Short distance to downtown Orlando, Orlando International Airport, Sanford Airport, theme parks and easy access to beaches on both coasts.

2122 Ridge Drive, Winter Park