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

176 Properties Found. Page 1 of 4.
Photo of Listing #O5949590

1411 Via Tuscany

$18,500,000
WINTER PARK
MLS® # O5949590
5 Beds, 10 Baths, 9,092 Sf
Photo of Listing #O5937062

1000 Genius Drive

$12,495,000
WINTER PARK
MLS® # O5937062
10 Beds, 12 Baths, 13,855 Sf
Photo of Listing #O5932285
Reduced 5.8%

55 Trismen Terrace

$4,895,000
WINTER PARK
MLS® # O5932285
4 Beds, 6 Baths, 6,690 Sf
Photo of Listing #O5933713
Reduced 3.5%

171 Genius Drive

$3,950,000
WINTER PARK
MLS® # O5933713
4 Beds, 6 Baths, 5,273 Sf
Photo of Listing #O5948908
WINTER PARK
MLS® # O5948908
3 Beds, 5 Baths, 4,390 Sf
Photo of Listing #O5935400
WINTER PARK
MLS® # O5935400
4 Beds, 5 Baths, 4,901 Sf
Photo of Listing #O5941194
WINTER PARK
MLS® # O5941194
5 Beds, 7 Baths, 8,910 Sf
Photo of Listing #O5919481
Reduced 90%
WINTER PARK
MLS® # O5919481
3 Beds, 4 Baths, 2,363 Sf
Photo of Listing #O5952385
New

541 Virginia Drive

$3,499,000
WINTER PARK
MLS® # O5952385
4 Beds, 4 Baths, 4,586 Sf
Photo of Listing #O5936507
Reduced 8.6%

1210 Alberta Drive

$3,195,000
WINTER PARK
MLS® # O5936507
4 Beds, 6 Baths, 5,449 Sf
Photo of Listing #O5930531
WINTER PARK
MLS® # O5930531
3 Beds, 5 Baths, 4,160 Sf
Photo of Listing #O5943412

1570 Bryan Avenue

$2,750,000
WINTER PARK
MLS® # O5943412
6 Beds, 7 Baths, 4,627 Sf
Photo of Listing #O5942281

1851 Via Tuscany

$2,650,000
WINTER PARK
MLS® # O5942281
4 Beds, 7 Baths, 4,445 Sf
Photo of Listing #O5948906

N/A

$2,500,000
WINTER PARK
MLS® # O5948906
4 Beds, 5 Baths, 4,288 Sf
Photo of Listing #O5945090

2615 Oglesby Avenue

$2,500,000
WINTER PARK
MLS® # O5945090
7 Beds, 8 Baths, 6,700 Sf
Photo of Listing #O5940425

200 Oakwood Way

$2,500,000
WINTER PARK
MLS® # O5940425
5 Beds, 6 Baths, 4,370 Sf
Photo of Listing #O5922251
Reduced 3.8%

210 Virginia Drive

$2,500,000
WINTER PARK
MLS® # O5922251
5 Beds, 7 Baths, 3,749 Sf
Photo of Listing #O5896286

1660 Palmer Avenue

$2,415,000
WINTER PARK
MLS® # O5896286
4 Beds, 6 Baths, 5,400 Sf
Photo of Listing #O5932669

2550 Venetian Way

$2,400,000
WINTER PARK
MLS® # O5932669
4 Beds, 5 Baths, 4,875 Sf
Photo of Listing #O5951693
New

1667 Lasbury Avenue

$2,250,000
WINTER PARK
MLS® # O5951693
4 Beds, 5 Baths, 4,821 Sf
Photo of Listing #O5930516
WINTER PARK
MLS® # O5930516
3 Beds, 5 Baths, 3,244 Sf
Photo of Listing #O5903824

138 Detmar Drive

$2,250,000
WINTER PARK
MLS® # O5903824
6 Beds, 8 Baths, 5,430 Sf
Photo of Listing #O5941598

780 Pinetree Road

$1,995,000
WINTER PARK
MLS® # O5941598
4 Beds, 5 Baths, 4,553 Sf
Photo of Listing #O5948992
WINTER PARK
MLS® # O5948992
4 Beds, 5 Baths, 5,114 Sf
Photo of Listing #O5949313
Reduced 32%

1707 Temple Drive

$1,850,000
WINTER PARK
MLS® # O5949313
6 Beds, 5 Baths, 3,926 Sf
Photo of Listing #O5917629
Reduced 10.8%

2156 Talman Court

$1,850,000
WINTER PARK
MLS® # O5917629
5 Beds, 8 Baths, 7,762 Sf
Photo of Listing #O5952372
New

285 Rippling Lane

$1,600,000
WINTER PARK
MLS® # O5952372
2 Beds, 3 Baths, 2,849 Sf
Photo of Listing #O5948695
WINTER PARK
MLS® # O5948695
3 Beds, 4 Baths, 2,291 Sf
Photo of Listing #O5949544
New

420 Alberta Drive

$1,575,000
WINTER PARK
MLS® # O5949544
4 Beds, 5 Baths, 3,915 Sf
Photo of Listing #O5947358
Reduced 6.3%

871 Mayfield Avenue

$1,500,000
WINTER PARK
MLS® # O5947358
5 Beds, 6 Baths, 4,488 Sf
Photo of Listing #O5952117
New

2224 Venetian Way

$1,499,000
WINTER PARK
MLS® # O5952117
4 Beds, 4 Baths, 3,673 Sf
Photo of Listing #O5952301
New
WINTER PARK
MLS® # O5952301
5 Beds, 3 Baths, 3,318 Sf
Photo of Listing #O5919292

1251 Richmond Road

$1,475,000
WINTER PARK
MLS® # O5919292
3 Beds, 4 Baths, 3,613 Sf
Photo of Listing #O5944228
WINTER PARK
MLS® # O5944228
5 Beds, 5 Baths, 3,412 Sf
Photo of Listing #O5943990

1861 Taylor Avenue

$1,460,000
WINTER PARK
MLS® # O5943990
5 Beds, 5 Baths, 3,545 Sf
Photo of Listing #O5948216

1701 Walnut Avenue

$1,450,000
WINTER PARK
MLS® # O5948216
4 Beds, 4 Baths, 4,200 Sf
Photo of Listing #O5922949
Reduced 3.3%
WINTER PARK
MLS® # O5922949
3 Beds, 4 Baths, 3,118 Sf
Photo of Listing #O5950597
Reduced 4.8%
WINTER PARK
MLS® # O5950597
4 Beds, 4 Baths, 3,370 Sf
Photo of Listing #O5951141
New

1024 Tuscany Place

$1,348,000
WINTER PARK
MLS® # O5951141
4 Beds, 4 Baths, 4,000 Sf
Photo of Listing #O5949470
WINTER PARK
MLS® # O5949470
4 Beds, 5 Baths, 2,950 Sf
Photo of Listing #O5951475
New

1021 Lincoln Circle

$1,295,000
WINTER PARK
MLS® # O5951475
3 Beds, 3 Baths, 2,284 Sf
Photo of Listing #O5943523
WINTER PARK
MLS® # O5943523
6 Beds, 5 Baths, 4,531 Sf
Photo of Listing #O5935506
Reduced 2.3%

543 Shepherd Avenue

$1,250,000
WINTER PARK
MLS® # O5935506
4 Beds, 4 Baths, 3,707 Sf
Photo of Listing #O5940017
Reduced 3.9%

2550 Temple Drive

$1,240,000
WINTER PARK
MLS® # O5940017
4 Beds, 3 Baths, 3,227 Sf
Photo of Listing #O5952091
New

1220 Via Del Mar

$1,195,000
WINTER PARK
MLS® # O5952091
4 Beds, 5 Baths, 3,993 Sf
Photo of Listing #O5947349
New

1320 Heavenly Cove

$1,099,000
WINTER PARK
MLS® # O5947349
7 Beds, 5 Baths, 5,120 Sf
Photo of Listing #O5935754
Reduced 3.5%
WINTER PARK
MLS® # O5935754
3 Beds, 4 Baths, 2,714 Sf
Photo of Listing #O5945404
WINTER PARK
MLS® # O5945404
2 Beds, 2 Baths, 1,605 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 June 19th, 2021 at 10:46pm EDT.