Winter Park Homes for Sale

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Single Family

2034 EAST END AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
1Parking(s)
25Picture(s)
2,714Sqft
New listing! Check out this amazing, newly built home by Barefoot Brothers, just steps from the East End Market. Built in 2019, this 3-bedroom, 3.5 bath home features an open floor plan with an oversized 1-car garage.
$1,049,000

Single Family

1281 WOODMERE DRIVE, WINTER PARK, Florida 32789

5Bedroom(s)
6Bathroom(s)
2Parking(s)
37Picture(s)
4,027Sqft
The definition of relaxed elegance. A remarkable collaboration by Phil Kean Design Group and Scout & Co. Lifestyle + Design resulted in a dreamy 4,027 SF custom built home in The Vias area, featuring five bedrooms, five full bathrooms, one half bathroom, a two car garage, a detached casita and a pool.
$2,095,000

Townhouse

503 W CANTON AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
22Picture(s)
2,319Sqft
Under Construction. Enjoy luxury living and premium sought after location at Vilasa Homes, the newest construction in Winter Park, FL 32789. February-March 2022 opening for models. Taking presales now.
$875,000

Townhouse

501 W CANTON AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
21Picture(s)
2,349Sqft
Under Construction. Enjoy luxury living and premium sought after location at Vilasa Homes, the newest construction in Winter Park, FL 32789. February-March 2022 opening for models. Taking presales now.
$875,000

Single Family

541 W CANTON AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
6Picture(s)
884Sqft
Build your dream home on a corner lot in the highly desired 32789 zip code. The lot dimensions are 78'x112'. It is located with walking distance from Park Avenue, The Winter Park Village, Rollins College, the new library, and public transportation. The house is rented until 3/2022. Please do not approach the house without verification first.
$450,000

Townhouse

777 S DENNING DRIVE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
27Picture(s)
1,661Sqft
Location, location, location! Check out this fully renovated, fully furnished, 3/3 modern/industrial/rustic townhouse within the confines of the charming Winter Park and Rollins College. The unique upgrades in all three bathrooms along with the show-stopper custom kitchen make this the perfect gathering spot for watching Rollins baseball home games from your balcony.
$549,999

Lots And Land

2341 MULBRY DRIVE, WINTER PARK, Florida 32789

25Picture(s)
0.16Acre
Welcome home to the most sought after area in Central Florida. Only steps away from Blue Jacket Park, minutes from Park Avenue and one block from Baldwin Park. Did we mention TOP RATED SCHOOLS? This wonderful Winter Park location has been blossoming with million dollar custom homes. With the land alone being worth over $400,000, this beauty will not last long.
$389,000

Single Family

511 W CANTON AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
7Bathroom(s)
5Parking(s)
25Picture(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.
$3,500,000

Single Family

460 CLARENDON AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
5Bathroom(s)
2Parking(s)
5Picture(s)
3,412Sqft
Pre-Construction. To be built. A Winter Park dream…walking distance to Park Avenue, deeded lake access and the opportunity to pick your own finishes. This home blends modern design with hand crafted touches. This spacious, light-filled open floor plan includes 5 bedrooms and 4.5 bathrooms. This Luxury pool home is perfect for entertaining.
$1,460,000

Single Family

670 N PENNSYLVANIA AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
3Bathroom(s)
1Parking(s)
25Picture(s)
2,112Sqft
Craving a project? Make West Winter Park your new home with this blank canvas of a house and its grandfathered-in garage apartment, 500-feet away from million-dollar zero-lot-line homes. The owner has building plans designed to make the principal residence a three-bedroom, three-bathroom home and to make the garage apartment into a two-bedroom, two-bathroom, with two garage spaces below.
$449,900

Single Family

1217 HARDING STREET, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
3,002Sqft
Welcome to this stunning, tucked away, four-bedroom Winter Park home built in 2016 by renowned Z Properties. When you pull into the driveway the first thing you'll see is a detached, 2 car garage - the second floor is a spacious studio that includes a bedroom with a seating area, a full bathroom, a private entrance, and lots of natural light.
$1,750,000

Single Family

2235 HOWARD DRIVE, WINTER PARK, Florida 32789

4Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
2,420Sqft
A gorgeous urban oasis sitting on Lake Forest right in the middle of Winter Park! Zoned for Audubon Park K-8 and Winter Park High School, this home sits on Lake Forest with 4 bedrooms, 2 updated bathrooms and loads of charm! Spanish tile flows throughout this light and bright home with a wall of glass doors opening into a spacious family room with wooden bar and brick flooring, anchored by a larg
$749,000

Townhouse

1003 S KENTUCKY AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
21Picture(s)
1,803Sqft
Granite counter tops/Stainless steel appliances with natural gas burners. Living area features gas fireplace,bamboo hardwood floors and surround sound speakers. Private court yard/Great for entertaining. Large Master suite with walk in closet. Located near shopping and Park Ave entertainment.
$486,000

Single Family

677 W SWOOPE AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
2Picture(s)
754Sqft
Location, Location, Location. Right in the heart of Winter Park. This property is the perfect opportunity to build a new home. Close to the Winter Park Village, Rollins College, Hannibal Square, Sun Rail, and many Fine Restaurants. Not far from Downtown Orlando. Excellent Schools. SOLD AS IS NO HOA Buyer to independently verify all measurements and condition.
$315,000

Single Family

1861 TAYLOR AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
5Bathroom(s)
2Parking(s)
4Picture(s)
3,150Sqft
Pre-Construction. To be built. Take a deep breath because you're home in this fantastic Winter Park new-build, located minutes away from Rollins College, Park Avenue, shopping and restaurants. The generous floor plan offers a vast amount of functional living area, storage and sleeping space.
$1,460,000

Single Family

915 N KENTUCKY AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
1Picture(s)
3,166Sqft
Pre-Construction. To be built. Excellent opportunity to build a modern coastal custom home with a 2 car rear entry garage in a very desirable location. This 3148 square foot home is perfect for entertaining guests yet comfortable for your everyday lifestyle.
$1,485,000

Single Family

2341 MULBRY DRIVE, WINTER PARK, Florida 32789

3Bedroom(s)
1Bathroom(s)
1Parking(s)
25Picture(s)
1,165Sqft
Welcome home to the most sought after area in Central Florida. Only steps away from Blue Jacket Park, minutes from Park Avenue and one block from Baldwin Park. Did we mention TOP RATED SCHOOLS? This wonderful Winter Park location has been blossoming with MILLION DOLLAR custom homes. With the land alone being worth over $400,000, this beauty will not last long.
$389,000

Single Family

1620 WESTCHESTER AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,915Sqft
First time on the market! Luxury buyers seeking high quality custom construction in the Winter Park, Orwin Manor, College Park areas will want to preview this gorgeous open floor plan estate-level home conveniently located in the heart of Downtown Orlando's most sought after living districts.
$1,179,500

Condominium

151 N ORLANDO AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
24Picture(s)
1,875Sqft
Welcome Home to this immaculately maintained and one-of-a-kind double condo in the heart of Winter Park! Conveniently located near shopping, entertainment, dining, and a short drive away from Downtown, you'll love calling this serene setting, home! The expansive unit features remarkable water views of the lake from all rooms!! As you enter the home, you will love the open floor concept that welco
$650,000

Single Family

1591 CARDINAL COURT, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,523Sqft
WINTER PARK-Walk to Park Avenue-Beautiful four-bedroom, three full baths + office, single-story home in the Heart of Winter Park. Tucked away behind Park Grove, this spacious 3,500+ SF home sits on a large corner lot in a quiet neighborhood and is zoned for some of the best schools. Inside you will find an open and inviting layout with a split bedroom floor plan.
$1,015,000

Single Family

1551 NORFOLK AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
3Bathroom(s)
1Parking(s)
25Picture(s)
2,740Sqft
FABULOUS LOCATION! Key West style 5 Bedroom/3 Bath POOL home nestled in a lovely tree lined street in the neighborhood of Orwin Manor in Winter Park. Charming curb appeal on an OVERSIZED CORNER LOT w/ lush landscaping. Walk into the large Living Room w/ wood-burning Fireplace & built-in shelving which flows into the 24’ slate floored Dining Room.
$675,000

Condominium

311 E MORSE BOULEVARD, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,214Sqft
Best location off Park Avenue in Winter Park! Custom 2/2 remodeled corner unit on first floor with almost 1500 square feet in Whispering Waters! Abundance of natural lighting with floor to ceiling views of ponds and landscaped grounds.
$649,000

Condominium

311 E MORSE BOULEVARD, WINTER PARK, Florida 32789

1Bedroom(s)
1Bathroom(s)
1Parking(s)
25Picture(s)
900Sqft
Fabulous turn-key living or second home in the heart of Winter Park! This Whispering Waters’ spacious 1/1 with designated parking space is ready for a new owner to enjoy this waterfront living complex with top restaurants, shops and activities a stone’s throw away! Entry way leads to the light and bright living room with floor to ceiling sliding glass doors into spacious scree
$386,000

Condominium

311 E MORSE BOULEVARD, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
18Picture(s)
2,350Sqft
MUST SELL!! 2350 sq ft ground floor condo facing the lake!! Awesome downtown location! Possible, rent with option to buy! ALL OFFERS CONSIDERED!! NEW KITCHEN!!l!! Large 1st floor renovated 3/3 condo on Winter Park chain of lakes!! Beautiful lake view from living room. HOA includes electricity! New kitchen, white shaker cabinets & gray veined white quartz counters.
$815,000

Lots And Land

715 DOUGLAS AVENUE, WINTER PARK, Florida 32789

18Picture(s)
0.08Acre
*AERIAL VIDEO AVAILABLE* This lot is cleared and ready for you to build your dream home! Douglas Avenue is a quiet street located within 1 block of Winter Park’s famous Hannibal Square, restaurants, and shopping. The sellers have worked with a local builder to design a ~1,100 square foot home to fit on the property.
$285,000

Single Family

532 WORTHINGTON DRIVE, WINTER PARK, Florida 32789

5Bedroom(s)
6Bathroom(s)
2Parking(s)
4Picture(s)
4,214Sqft
Pre-Construction. To be built. Here is the perfect opportunity to own your very own private sanctuary in the heart of Winter Park. This exquisite transitional modern home by Parade of Homes award winning builder Clarkson Concepts was designed with incredible details that will not disappoint. The home features a beautiful private courtyard entrance with a water feature.
$2,000,000

Single Family

1935 ALBERT LEE PARKWAY, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,316Sqft
Great 3/2 home plus Office or 4th Bedroom located in the quiet neighborhood of Albert Lee Ridge a highly desirable area of Winter Park. No HOA.
$319,900

Single Family

1409 CHAPMAN CIRCLE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,043Sqft
Just Listed! Stunning, Mediterranean-inspired pool home in Winter Park’s Windsong community. This exquisite 3-bedroom home offers over 3,000 SF of luxurious interior living space and an outdoor entertainment area complete with a cocktail pool and summer kitchen.
$1,150,000

Single Family

690 N NEW YORK AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
2Parking(s)
6Picture(s)
4,901Sqft
Pre-Construction. To be built. Greens at Park. This address says it all…690 N. New York Avenue, where unparalleled luxury meets quintessential Winter Park lifestyle. Iconic English cottage architecture. This is a once in a lifetime opportunity to own a single family (fee simple) luxury real estate home in the heart of Winter Park.
$3,850,000

Condominium

662 OSCEOLA AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,290Sqft
Welcome Home to PERLE DU LAC, One of Winter Parks most desirable luxury lake front communities. Located on the pristine Lake Virginia with its own private deeded boat slip, this property provides lakefront living at it's finest. Upon entering this beautiful 3 bedroom 3.5 Bathroom home, you are greeted with a completely remodeled Open concept floor plan with its focus on the Lake & Pool views.
$1,950,000
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Tony Johnson - Realtor - Greater Orlando FL Area Homes for Sale and Real Estate Listings