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Winter Park Real Estate Winter Park Orlando Florida

Located northeast of Downtown Orlando, Winter Park is a city of beautiful natural scenery and friendly small town villages. Winter Park real estate is populated by approximately 25,000 residents and nearly as many oak trees. Originally a sanctuary for artists and many of the countries most influential families, Winter Park provides its citizens with relaxing, upscale living with the comforts of nature and the nearby excitement of Central Florida's world-class attractions.

Winter Park Homes for Sale

207 Properties Found. Page 1 of 5.
Photo of Listing #O6112070
Reduced 15.6%

1461 Via Tuscany

$13,500,000
WINTER PARK
MLS® # O6112070
5 Beds, 6 Baths, 8,353 Sf
Photo of Listing #O6095179

4 Isle Of Sicily

$10,950,000
WINTER PARK
MLS® # O6095179
5 Beds, 8 Baths, 9,522 Sf
Photo of Listing #O6156666
WINTER PARK
MLS® # O6156666
5 Beds, 7 Baths, 8,883 Sf
Photo of Listing #O6133999
Reduced 11.2%
WINTER PARK
MLS® # O6133999
5 Beds, 8 Baths, 8,752 Sf
Photo of Listing #O6120809

2228 Azalea Place

$5,400,000
WINTER PARK
MLS® # O6120809
5 Beds, 6 Baths, 5,072 Sf
Photo of Listing #O6029085

550 Palmer Avenue

$4,900,000
WINTER PARK
MLS® # O6029085
5 Beds, 8 Baths, 5,952 Sf
Photo of Listing #O6152759

1391 Richmond Road

$4,220,000
WINTER PARK
MLS® # O6152759
4 Beds, 6 Baths, 4,635 Sf
Photo of Listing #O6034151
Reduced 4.6%

2056 Lake Drive

$3,999,999
WINTER PARK
MLS® # O6034151
5 Beds, 6 Baths, 5,907 Sf
Photo of Listing #O6154240

2379 Forrest Road

$3,995,000
WINTER PARK
MLS® # O6154240
5 Beds, 7 Baths, 4,483 Sf
Photo of Listing #O6143278
WINTER PARK
MLS® # O6143278
3 Beds, 3 Baths, 2,143 Sf
Photo of Listing #O6157505

1635 Highland Road

$3,500,000
WINTER PARK
MLS® # O6157505
5 Beds, 6 Baths, 4,325 Sf
Photo of Listing #O6127492
WINTER PARK
MLS® # O6127492
5 Beds, 6 Baths, 4,961 Sf
Photo of Listing #O6092664

1150 Via Salerno

$3,495,000
WINTER PARK
MLS® # O6092664
4 Beds, 5 Baths, 3,826 Sf
Photo of Listing #O6152119
Reduced 3.3%
WINTER PARK
MLS® # O6152119
6 Beds, 5 Baths, 4,522 Sf
Photo of Listing #O6146090

2080 Sharon Road

$3,350,000
WINTER PARK
MLS® # O6146090
4 Beds, 6 Baths, 4,080 Sf
Photo of Listing #O6152284
Reduced 3.3%

633 S Phelps Ave

$3,095,000
WINTER PARK
MLS® # O6152284
5 Beds, 5 Baths, 4,950 Sf
Photo of Listing #O6086964
Reduced 7.4%

2138 Lake Drive

$3,050,000
WINTER PARK
MLS® # O6086964
4 Beds, 4 Baths, 5,100 Sf
Photo of Listing #O6154348
WINTER PARK
MLS® # O6154348
4 Beds, 4 Baths, 4,413 Sf
Photo of Listing #O6145633

1741 Glencoe Road

$2,749,000
WINTER PARK
MLS® # O6145633
4 Beds, 5 Baths, 4,692 Sf
Photo of Listing #O6151600
WINTER PARK
MLS® # O6151600
3 Beds, 4 Baths, 3,110 Sf
Photo of Listing #O6143813

2100 Lake Drive

$2,275,000
WINTER PARK
MLS® # O6143813
4 Beds, 4 Baths, 3,555 Sf
Photo of Listing #O6154620
New
WINTER PARK
MLS® # O6154620
4 Beds, 5 Baths, 3,448 Sf
Photo of Listing #O6103239
WINTER PARK
MLS® # O6103239
7 Beds, 6 Baths, 4,517 Sf
Photo of Listing #O6155394

2701 Norris Avenue

$2,195,000
WINTER PARK
MLS® # O6155394
4 Beds, 4 Baths, 3,259 Sf
Photo of Listing #O6081797
Reduced 1.1%

2723 Norris Avenue

$2,175,000
WINTER PARK
MLS® # O6081797
4 Beds, 4 Baths, 4,000 Sf
Photo of Listing #O6150036

1800 Bryan Avenue

$1,995,000
WINTER PARK
MLS® # O6150036
4 Beds, 5 Baths, 2,951 Sf
Photo of Listing #O6138358

1731 Windsor Drive

$1,995,000
WINTER PARK
MLS® # O6138358
4 Beds, 4 Baths, 3,669 Sf
Photo of Listing #O6157218
WINTER PARK
MLS® # O6157218
3 Beds, 4 Baths, 3,112 Sf
Photo of Listing #O6147459
Reduced 89.8%

1814 Barker Drive

$1,950,000
WINTER PARK
MLS® # O6147459
5 Beds, 4 Baths, 4,100 Sf
Photo of Listing #O6156460
Reduced 5%
WINTER PARK
MLS® # O6156460
3 Beds, 2 Baths, 1,952 Sf
Photo of Listing #O6155758
WINTER PARK
MLS® # O6155758
2 Beds, 3 Baths, 2,778 Sf
Photo of Listing #O6154133

1530 Via Tuscany

$1,895,000
WINTER PARK
MLS® # O6154133
4 Beds, 4 Baths, 3,341 Sf
Photo of Listing #O6116410
Reduced 2.6%

431 Fletcher Place

$1,850,000
WINTER PARK
MLS® # O6116410
4 Beds, 4 Baths, 4,257 Sf
Photo of Listing #O6161030
New

2016 Lake Drive

$1,799,900
WINTER PARK
MLS® # O6161030
3 Beds, 2 Baths, 2,560 Sf
Photo of Listing #O6147977
Reduced 5.3%
WINTER PARK
MLS® # O6147977
4 Beds, 4 Baths, 2,829 Sf
Photo of Listing #O6155398
WINTER PARK
MLS® # O6155398
4 Beds, 4 Baths, 2,785 Sf
Photo of Listing #O6140784
Reduced 2.7%

600 Maiden Lane

$1,795,000
WINTER PARK
MLS® # O6140784
4 Beds, 5 Baths, 3,781 Sf
Photo of Listing #O6120431
Reduced 5.6%
WINTER PARK
MLS® # O6120431
4 Beds, 4 Baths, 3,723 Sf
Photo of Listing #O6129924
Reduced 8.3%

1871 Taylor Avenue

$1,649,000
WINTER PARK
MLS® # O6129924
4 Beds, 5 Baths, 3,401 Sf
Photo of Listing #O6150869
WINTER PARK
MLS® # O6150869
2 Beds, 2 Baths, 1,620 Sf
Photo of Listing #O6143105
WINTER PARK
MLS® # O6143105
2 Beds, 1 Baths, 924 Sf
Photo of Listing #O6087208
Reduced 3%

281 Brewer Avenue

$1,600,000
WINTER PARK
MLS® # O6087208
5 Beds, 5 Baths, 4,029 Sf
Photo of Listing #O6124486
Reduced 5.9%
WINTER PARK
MLS® # O6124486
5 Beds, 5 Baths, 4,137 Sf
Photo of Listing #O6141884
Reduced 8.9%

40 Palmer Avenue

$1,595,000
WINTER PARK
MLS® # O6141884
5 Beds, 5 Baths, 4,166 Sf
Photo of Listing #O6159101
WINTER PARK
MLS® # O6159101
4 Beds, 4 Baths, 3,052 Sf
Photo of Listing #O6144100
Reduced 3.1%

1600 Barcelona Way

$1,550,000
WINTER PARK
MLS® # O6144100
4 Beds, 4 Baths, 3,014 Sf
Photo of Listing #O6143102
Reduced 4.9%
WINTER PARK
MLS® # O6143102
3 Beds, 3 Baths, 2,734 Sf
Photo of Listing #O6147639

413 Balmoral Rd

$1,499,990
WINTER PARK
MLS® # O6147639
3 Beds, 3 Baths, 3,845 Sf

More about Winter Park

A journey into Winter Park reveals breathtaking luxury homes, gorgeous scenery, and an inviting community of towns with character and old world charm.  Packed with 70 different parks and a beautiful chain of lakes, Winter Park has earned a reputation as a one Central Florida's most relaxing and tranquil cities. Chartered in 1870, Winter Park gets its name from the wealthy northerners who visited the city to escape harsh and cold winters.  Fortunately, Winter Park has retained that aesthetic throughout the years.

Winter Park Luxury Real Estate

Winter Park is famous for its brick lined streets, tall oak trees, and European style thoroughfare. Blocks and blocks of boutique shops, sidewalk cafés, and courtyards populate the city. There is a wide range of fine dining restaurants, local theaters and museums, including the Charles Hosmer Morse Museum of American Art, housing the world's largest collection of Tiffany glass. Being a city rich in culture, residents enjoy year round festivals and events from the Sidewalk Art Festival to the Exotic Car Show to Saturday morning Farmers' markets. It is the city's beauty and sense of community that attracts these celebrations and makes them highly anticipated events.

Downtown Winter Park Orlando Florida

Thanks to the Winter Park Chain of Lakes, residents take advantage of plenty of water recreation from boating and fishing to swimming and water skiing. The shores of Lake Virginia are home to Florida's oldest institution of higher education, Rollins College. Home to the Cornell Fine Art museum and the world renowned Bach Festival Choir, Rollins College is recognized by U.S. News and World Report as one of  "America's Best Colleges." The local schools are considered to be some of Florida's finest, making Winter Park the perfect place to raise a family.

As special and unique as Winter Park is, citizens can easily travel to another one of Florida's most exciting places, Orlando. Just a short drive away, downtown Orlando has world class dining and entertainment, exquisite shopping opportunities, and an elegant night life. World famous theme parks such as Walt Disney World, Universal Studios, and Sea World are perfectly in reach for family getaways. Winter Park is so close to the excitement while remaining far enough away to be sheltered from the hustle and bustle associated with big city living.

Since its inception, Winter Park has been refuge for those looking for a comfortable yet exciting place to live, complete with picturesque parks, rich culture and history, and amazing educational opportunities.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on December 5th, 2023 at 9:10am EST.