Winter Park Homes for Sale

Sort Option
  • _score
  • Price ↓
  • Newest Listings First
  • Square Footage ↓
  • Year Built ↓
Grid
List
Map

Single Family

858 DOUGLAS AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
1Bathroom(s)
25Picture(s)
1,225Sqft
Charming 3 bed 1 bath home located in the heart of Winter Park. This property has so much potential located on an oversized double lot. Walking distance to Park Avenue restaurants, shopping, and more.
$360,000

Single Family

1442 MILLER AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
1Parking(s)
20Picture(s)
2,250Sqft
Under Construction. (Under Construction) Winter Park luxury living at its absolute finest! Multiple Award-Winning Builder Ira Kitograd of IBK Construction, who has over twenty-five years of building in the Winter Park area, has created another custom residence that will surely exceed your expectations. The two-story home has three bedrooms, each with its own en-suite bathroom.
$770,000

Single Family

1751 GOODRICH AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,170Sqft
This almost-new light and bright home with top of the line finishes was fully renovated in 2019. Seller will provide 1 year home warranty. 2,172 sq ft under air, 4 Beds, 3.5 bathrooms and 2 car garage, this home has no details left behind. Full of upgrades and technology, this smart home will do things for you.
$815,000

Single Family

1555 GRANVILLE DRIVE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,634Sqft
OVERSIZED CORNER LOT....WELCOME TO PARK GROVE, ONE OF WINTER PARK'S HOTTEST NEIGHBORHOODS. RECENTLY APPRAISED. LOCATED ON A BEAUTIFUL TREE LINED STREET ONE BLOCK OFF PARK AVE, THIS ONE STORY HOME SITS ON AN OVERSIZED CORNER LOT WITH OVER 3600 SF. AS YOU ENTER THE CIRCULAR PAVED DRIVEWAY, YOU IMMEDIATELY NOTICE THE WELL MANICURED LANDSCAPING.
$1,299,000

Lots And Land

1136 OAKS BOULEVARD, WINTER PARK, Florida 32789

14Picture(s)
0.36Acre
This is a perfect location to build your custom home on this oversized lot off Park Avenue in Winter Park. The property measures 15,836 square feet with lot dimensions of 107-feet frontage by 148-feet deep. It is located in a quiet community, just minutes from the award-winning restaurants and boutique shops of Park Avenue.
$695,000

Single Family

1136 OAKS BOULEVARD, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
21Picture(s)
2,012Sqft
Remodel existing home or it is a perfect location to build your custom home on this oversized lot off Park Avenue in Winter Park. The property measures 15,836 square feet with lot dimensions of 107-feet frontage by 148-feet deep. It is located in a quiet community, just minutes from the award-winning restaurants and boutique shops of Park Avenue.
$695,000

Townhouse

1267 MICHIGAN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
10Picture(s)
1,866Sqft
Stunning new townhome community in the Heart of Winter Park! Multiple units available. This particular unit is the model home. Built by award-winning Osprey Custom Home Builders, this 3 bedroom, 2.5 bath home has been designated a Florida Green Certified Home and offers a highly-desirable, open-concept layout with designer finishes throughout.
$469,900

Single Family

1435 SUNNYSIDE DRIVE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
25Picture(s)
1,376Sqft
Stop the car and bring your suitcase! This Winter Park updated bungalow with 3 bedrooms and 2 baths is move in ready! Front walkway welcomes friends and family members into the open living room with an abundance of natural light and hard wood floors. Nearby is a spacious dining area and kitchen with stainless appliances, granite counters and custom cabinetry.
$399,000

Single Family

740 PALMER AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
4,810Sqft
If you’re looking for the quintessential Winter Park Lakefront Estate Home this is it! Designed by acclaimed architect Gamble Rogers this magnificent home has double waterfrontage on both Lake Osceola and the Venetian Canal.
$2,950,000

Single Family

1080 KENWOOD AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,317Sqft
Under Construction. BRAND NEW CONSTRUCTION IN WINTER PARK! Scheduled to be completed in October 2020 this stunning modern farmhouse was designed and built by Homes by Carmen Dominguez. Every detail of this home has been thoughtfully planned and executed to perfection. The fantastic layout, which was a 2020 Parade of Homes Winner for best design feature, offers 3,317 Sf of open living space.
$1,250,000

Single Family

1650 DALE AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
1Parking(s)
25Picture(s)
4,577Sqft
Set on an oversized 0.45 acre lot (125’x157’) this sprawling Winter Park home features 4,577 sf of interior living space complimented by beautiful hardwood floors, high ceilings, an open layout and so much more. As you enter the home you’ll find a large living/dining room to the left of the foyer and an office/den to the right.
$1,295,000

Single Family

1050 ALOMA AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
2,112Sqft
Stunning 3 bedroom 2 bath pool home minutes to the prestigious Park Avenue. This home sits on a large lot with a huge driveway and two car garage. Step inside to an amazing open concept living room with dark wood floors, modern fireplace and vaulted ceilings. Formal dining space and a gorgeous renovated kitchen with center island and additional dining space perfect for gatherings.
$519,900

Lots And Land

1681 WALNUT, WINTER PARK, Florida 32789

3Picture(s)
0.15Acre
Build your dream home or move in to this adorable 3 bedroom, 2 bath bungalow home is a rare find in one of Winter Park's most sought-after neighborhoods. Located on a shady, brick street surrounded by upscale houses, this home features an attractive kitchen opening into a family room with a fireplace and separate dining room.
$475,000

Single Family

280 STIRLING AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,428Sqft
WATERFRONT ESTATE: .58 acre tree canopied property framed by 249 feet on Howell Creek (with riparian rights, fishing platform, wildlife feeder & canoe) & wooded lot is the perfect setting for this charming yet elegant 4 bedroom/3.5 bath, 2 story beauty complete with 2400 sf of porches & balconies (rear decking recently replaced with pressure treated pine).
$1,950,000

Single Family

1690 DALE AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
2Bathroom(s)
25Picture(s)
1,474Sqft
RECENTLY RENOVATED. New kitchen cabinets with granite counter tops, brand new stainless steel appliances, updated bathrooms with custom tile work, fresh paint inside and out, new lighting fixtures, new flooring throughout, NEW ROOF AND WINDOWS. Home features an impressive owner’s suite with a large walk in closet and private entrance to the oversized deck.
$449,000

Lots And Land

715 DOUGLAS AVENUE, WINTER PARK, Florida 32789

21Picture(s)
0.08Acre
This lot is cleared and ready for you to build your dream home! Douglas Avenue is a quiet street and a must see.
$275,000

Single Family

1211 VIA ESTRELLA, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,770Sqft
Picturesque luxury. This delightful 4 bedroom, 3 bathroom house, plus office, marries the charm of a timeless transitional home with all of the hi-tech modern conveniences you can think of! Bevelo gas lanterns create a warm, rich ambience, while the clever use of space means that while expansive, the home manages to feel grounded and even cozy despite the high ceilings and generous room sizes.
$1,994,000

Lots And Land

280 STIRLING AVENUE, WINTER PARK, Florida 32789

15Picture(s)
0.58Acre
WATERFRONT .58 acre tree canopied property framed by 249 feet on Howell Creek & wooded lot is the perfect setting to build your dream home. OUTSTANDING LOCATION! Scenic stroll to Rollins College, Park Avenue's shoppes & restaurants and all that Downtown Winter Park has to offer! Howell Creek offers a quiet retreat to fish or begin your canoe/paddleboard journey to Lake Virginia.
$1,950,000

Single Family

1532 GRANVILLE DRIVE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,264Sqft
Welcome to Park Grove! Here is your opportunity to live in Winter Park's most desired neighborhood! Park Grove, with it's tree lined streets, has been Winter Park's most favorite neighborhood with it's close proximity to Park Avenue's fine restaurants and shops, the Winter Park Village, art museums and Winter Park's own Central Park! This traditional split-plan home has been loved for over 28 year
$801,000

Single Family

1301 MAYFIELD AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,722Sqft
Don't miss out on this beautiful home located in a prime, tree-lined Winter Park neighborhood. A short walk from downtown Winter Park, Kraft Azalea Gardens on Lake Maitland, and Phelps Park, this 3722 square foot home features Brazilian cherry hardwood floors and crown molding throughout. A large entry foyer opens into a gorgeous open kitchen with all stainless appliances.
$979,000

Single Family

2687 MERRIE OAKS ROAD, WINTER PARK, Florida 32792

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,921Sqft
WOW! Incredible opportunity to own this 4 bedroom, 3 bath home located in the highly desirable Winter Park Pines Golf Community. Features include a driveway, tray ceilings, pool and fenced in backyard! As you enter through the home you are greeted with a spacious living room. Kitchen features include tray ceilings, a breakfast bar, appliances, and an eat-in nook.
$439,900

Commercial

1788 W FAIRBANKS AVENUE, WINTER PARK, Florida 32789

10Picture(s)
7,645Sqft
List Price is for 3 Parcels: This listing includes two other Parcels that are all being sold together. Parcel 12-22-29-5000-04-040, which is a parking lot that serves as this parcel's parking lot. Parcel 12-22-29-5000-04-050, is a two-story building also owned by the seller. See MLS Listing#O5852283 for further details. Both buildings are ADA compliant.
$3,950,000

Single Family

1737 OAKHURST AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
2,300Sqft
One or more photo(s) has been virtually staged. Charming home located in the heart of Winter Park Historical District. Split floor plan with upgraded laminate floors throughout. Newer roof, newer A/C, vaulted ceilings, updated kitchen including granite counter tops & stainless steel appliances.
$520,000

Residential

511 W CANTON AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
7Bathroom(s)
5Parking(s)
10Picture(s)
8,910Sqft
Masterful design and modern luxury are uniquely embodied in this Spectacular Mid-Century Modern Estate. Stylish simplicity, extensive use of glass, and open design forge a connection with nature. Expansive entertaining spaces flow outside to the Grande Courtyard.
$3,350,000

Condominium

100 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,267Sqft
The Cloisters! A fabulous Winter Park location! The Cloisters is just a short walk off Park Avenue, convenient to restaurants, shops, banking, bakeries, coffee shops, the library, the park. Sun Rail/Amtrak and so much more. Situated on Lake Osceola with on site docking for your boat available, this unit overlooks the pool, gardens and has a lake view.
$500,000

Lots And Land

641 NORTHWOOD CIRCLE, WINTER PARK, Florida 32789

4Picture(s)
0.18Acre
BUILD YOUR DREAM HOME FOR $899,000 ON THIS VACANT LOT WITH PLANS IN THE HEART OF WINTER PARK! EXISTING PLANS CALL FOR A 2751 SFT HOME TO BE BUILT ON THIS 83X97 LOT. COME PICK YOUR COLORS AND FINISHES, OWNER/BUILDER HAS APPROVED PLANS (ATTACHED) FROM THE CITY FOR THIS CUSTOM HOME. WALK TO PARK AVENUE FROM THIS QUIET NEIGHBORHOOD OFF OF PENNSYLVANIA AVENUE.
$319,900

Single Family

1550 CHESTNUT AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Parking(s)
16Picture(s)
1,155Sqft
Come see this adorable move in ready home in highly desirable Winter Park location. This lovely 3 bedroom, 2 bath home with detached studio offers an updated kitchen with granite countertops and all appliances. The cozy dining area is open to a spacious living room with laminate floors and sliding glass doors to the, covered and screened patio.
$396,000

Townhouse

1047 N KENTUCKY AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,786Sqft
Welcome Home! This stunning, modern townhome is perfectly located just minutes from Winter Park shops and restaurants. Designed by internationally recognized, and award-winning Architect Phil Kean, this unique 3 bedroom, 2.5 bathroom home with endless upgrades, on one of Winter Park's famous brick streets is ready for you to call it Home.
$695,000

Single Family

1420 CHAPMAN CIRCLE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,313Sqft
Take the virtual tour: https://my.matterport.com/show/?m=ti1mdHMXxU9. This gorgeous custom-built 4 bedroom, 3.5 bathroom home is located in the exclusive Windsong subdivision in Winter Park and features 3,313 sqft of perfectly planned living space.
$924,900

Townhouse

1149 S PENNSYLVANIA STREET, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,358Sqft
Located just minutes from Winter Park’s famed Park Avenue, this beautiful 3 bedroom, 2 1/2 bath townhome designed by the award winning, world-renowned Nasrallah Architectural Group is ready to be called your new home! Get ready to be immersed in the Winter Park lifestyle, with all the charm of its Oak lined Brick Streets.
$750,000

Single Family

1681 WALNUT AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
25Picture(s)
1,499Sqft
This adorable 3 bedroom, 2 bath bungalow home is a rare find in one of Winter Park's most sought-after neighborhoods. Located on a shady, brick street surrounded by upscale houses, this home features an attractive kitchen opening into a family room with a fireplace and separate dining room.
$475,000

Lots And Land

797 PINETREE ROAD, WINTER PARK, Florida 32789

11Picture(s)
0.94Acre
RARE opportunity to build your Estate Home on sought after Lake Maitland, on the WINTER PARK CHAIN OF LAKES! You will enjoy this phenomenal location that is in the of the heart of the Via’s neighborhood and tucked away on a quiet, peaceful street. Just a short stroll to the Winter Park Racquet Club and minutes to Downtown Park Ave restaurants and shops.
$2,749,000

Single Family

1661 ORANGE AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
3Picture(s)
2,652Sqft
Pre-Construction. To be built. Pre-construction! Perfectly situated - close to Winter Park shopping and dining, Mead Botanical Gardens, College Park and Lake Ivanhoe. Great transport links with I-4 access nearby and a short drive to Sun Rail stations. Plans for a stunning 4 bed, 3 bath, 2,652 sqft townhome have been developed by one of Winter Park’s premier custom home builders.
$819,000

Single Family

2607 LAFAYETTE AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,770Sqft
One or more photo(s) has been virtually staged. Move-in ready, 2018 newer construction home with spacious, open and flexible floorplan in convenient Winter Park location. The interior is light and bright, with clean lines and great flow.
$685,000

Condominium

104 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
21Picture(s)
1,283Sqft
Ideal location in the heart of downtown Winter Park. Approximately 2 blocks from Park Avenue which is renowned for shopping & dining. Orlando International Airport can be reached from the downtown Sun Rail Station. Unit 313 features updated baths & kitchen. Brazilian hardwood floors, crown molding, plantation shutters throughout. Washer and dryer in the unit.
$470,000

Single Family

1807 BARKER DRIVE, WINTER PARK, Florida 32789

5Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,804Sqft
Welcome to 1807 Barker Drive, a lakefront home that includes tranquil views of a natural habitat, with magnificent sunsets off the water. Approximately 40% of the shoreline on Lake Spier is undeveloped, and this home has the most perfect view in town. Custom-built in 2004 by Bill Felkel, this home remains loved by the original owners.
$1,625,000

Condominium

100 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,271Sqft
The wait is over. Sophisticated, light, bright, open and updated Spacious two bedroom/two bath at the Cloisters in Downtown Winter Park. Open kitchen with large island, Carrera marble counters and beautiful white cabinetry. Spacious living/dining area with gorgeous wood floors offers wonderful views of Lake Osceola and serene grounds. Sun room has windows on three sides.
$495,000

Single Family

1035 N KENTUCKY AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,983Sqft
NEW PRICE! Location and style, this Winter Park POOL home has it all. A transitional modern, newer construction home set among other new, luxury homes on a charming brick street with a lovely view of Lake Midget. From the cozy front porch to the stunning interior, this gorgeous home will impress.
$1,149,000

Condominium

1250 S DENNING DRIVE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
21Picture(s)
884Sqft
This nicely remodeled 2 bedroom, 2 bath condo is the end unit on the ground floor overlooking the swimming pool. This condo underwent a major remodel about 10 years ago at which time it was stripped down to the wall studs and everything from the drywall in was replaced. The unit was replumbed, the electrical system updated, new AC, a new water heater, and even new windows.
$209,900

Single Family

1731 OAKHURST AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
7Bathroom(s)
3Parking(s)
25Picture(s)
4,398Sqft
Under Construction. This custom 5-Bd/5-Ba/2-HBa contemporary/transitional luxury home has been uniquely designed with an exceptional selection of neutral materials, finishes, and lighting to create a warm and elegant atmosphere.
$1,625,000

Single Family

2605 WINTER PARK ROAD, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
2,365Sqft
Beautiful newly renovated 3 bedroom 2 bath single-family home on 1/4 acre lot, located in a private community in the heart of Winter Park! This home has been remodeled and converted to an open floor plan perfect for any family! Come see what this home has to offer with loads of upgrades such as gourgous Hickory Hardwood flooring throughout, Custom Yorktowne onyx cabinets, Calacatta quartz countert
$599,900

Condominium

102 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
1Parking(s)
25Picture(s)
1,802Sqft
One of the best remodels in the Cloisters. New kitchen and new bathrooms. Wood floors throughout this three bedroom, two and a half bath almost maintenance free condo. Perfect for someone looking for lock and leave capability. Split plan with bright and open rooms and a treetop city view from balcony. Just one block from magnificent Park Avenue shops and restaurants.
$750,000

Lots And Land

280 E LAKE SUE AVENUE, WINTER PARK, Florida 32789

10Picture(s)
0.45Acre
First offering in 30 years...Where can you find nearly 1/2 Acre in any city, much less, desirable Olde Winter Park? Potential lot split into 2 building sites (70 x 140)--charming elevated presence on a brick street corner. Build your dream home or two. The existing home was built in 1950 and overall age and functional design imparts negligible value. The value of this property is strictly land.
$711,000

Single Family

661 COLUMBIA DRIVE, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
4,349Sqft
One-hundred-four expansive feet of Lake Maitland lakefront awaits on a quiet Olde Winter Park street just minutes away from Park Avenue. The home in mid-renovation, sold as-is, sits on a 102' x 299' x 104' x 268' lot (68,457 total square feet/1.57 acres). Here is the ideal opportunity to build the lakefront home of your dreams.
$2,795,000

Lots And Land

661 COLUMBIA DRIVE, WINTER PARK, Florida 32789

25Picture(s)
1.57Acre
One-hundred-four expansive feet of Lake Maitland lakefront awaits on a quiet Olde Winter Park street just minutes away from Park Avenue. The home in mid-renovation, sold as-is, sits on a 102' x 299' x 104' x 268' lot (68,457 total square feet/1.57 acres). Here is the ideal opportunity to build the lakefront home of your dreams. <br><br> Lake Maitland direct waterfront lot.
$2,795,000

Single Family

2880 ROXBURY ROAD, WINTER PARK, Florida 32789

3Bedroom(s)
1Bathroom(s)
1Parking(s)
25Picture(s)
1,348Sqft
Fantastic 2 bed, 1 Bath + Bonus Room home located in Winter Park. Conveniently nestled between all the shops and dining College Park AND Winter Park have to offer. Cute as a button and full of character and charm. Upon entry to this unbelievably WELL MAINTAINED home, you’re greeted to a lovely bonus room drenched in sunlight.
$299,000

Single Family

741 DIXIE PARKWAY, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,989Sqft
New listing in Green Oaks/Park Grove neighborhood. Beautiful traditional home with amazing curb appeal and large, oversized lot. Interior features approximately 3,000 SF including 4 bedrooms, 2.5 baths, formal living and dining rooms, a gathering room with fireplace, and charming kitchen with eat-in space. Wood floors flow throughout most of the interior, including the bedrooms.
$922,500

Condominium

140 E MORSE BOULEVARD, WINTER PARK, Florida 32789

2Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,450Sqft
Luxury living in the Landmark Building - Winter Park’s premiere address for privacy and proximity to all Park Ave has to offer.
$1,575,000
120 Results returned.Per Page
Do NOT follow this link or you will be banned from the site!