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

189 Properties Found. Page 1 of 4.
Photo of Listing #O5949590
Reduced 14.1%

1411 Via Tuscany

$15,900,000
WINTER PARK
MLS® # O5949590
5 Beds, 10 Baths, 9,092 Sf
Photo of Listing #A4508883

1106 Palmer Avenue

$4,350,000
WINTER PARK
MLS® # A4508883
4 Beds, 6 Baths, 6,500 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 #O5948908
Reduced 4%
WINTER PARK
MLS® # O5948908
4 Beds, 5 Baths, 4,390 Sf
Photo of Listing #O5969423
Reduced 1.8%

465 Genius Drive

$3,290,000
WINTER PARK
MLS® # O5969423
5 Beds, 6 Baths, 6,215 Sf
Photo of Listing #O5966216

1576 Williams Drive

$3,150,000
WINTER PARK
MLS® # O5966216
5 Beds, 7 Baths, 5,375 Sf
Photo of Listing #O5971004

1441 Cardinal Court

$2,795,000
WINTER PARK
MLS® # O5971004
4 Beds, 6 Baths, 3,992 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 #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 #O5896286

1660 Palmer Avenue

$2,415,000
WINTER PARK
MLS® # O5896286
4 Beds, 6 Baths, 5,400 Sf
Photo of Listing #O5932669
Reduced 4.8%

2550 Venetian Way

$2,285,000
WINTER PARK
MLS® # O5932669
4 Beds, 5 Baths, 4,875 Sf
Photo of Listing #O5964359
Reduced 9.8%

1005 Lakeview Drive

$2,250,000
WINTER PARK
MLS® # O5964359
3 Beds, 4 Baths, 2,344 Sf
Photo of Listing #O5962076

1741 Glencoe Road

$2,250,000
WINTER PARK
MLS® # O5962076
4 Beds, 5 Baths, 4,692 Sf
Photo of Listing #O5971616

450 Ololu Drive

$2,199,500
WINTER PARK
MLS® # O5971616
5 Beds, 6 Baths, 4,988 Sf
Photo of Listing #O5958349
Reduced 12.5%

1281 Woodmere Drive

$2,095,000
WINTER PARK
MLS® # O5958349
5 Beds, 6 Baths, 4,027 Sf
Photo of Listing #O5957066
WINTER PARK
MLS® # O5957066
5 Beds, 6 Baths, 4,214 Sf
Photo of Listing #O5971275

1520 Mizell Avenue

$1,995,000
WINTER PARK
MLS® # O5971275
5 Beds, 5 Baths, 4,516 Sf
Photo of Listing #V4921147
New
WINTER PARK
MLS® # V4921147
3 Beds, 4 Baths, 3,226 Sf
Photo of Listing #O5961025
WINTER PARK
MLS® # O5961025
3 Beds, 4 Baths, 2,290 Sf
Photo of Listing #O5948992
WINTER PARK
MLS® # O5948992
4 Beds, 5 Baths, 5,114 Sf
Photo of Listing #O5969099

1780 Palmer Avenue

$1,825,000
WINTER PARK
MLS® # O5969099
4 Beds, 6 Baths, 3,542 Sf
Photo of Listing #O5944753

1540 Glencoe Road

$1,750,000
WINTER PARK
MLS® # O5944753
5 Beds, 4 Baths, 4,905 Sf
Photo of Listing #O5953044

1217 Harding Street

$1,750,000
WINTER PARK
MLS® # O5953044
4 Beds, 5 Baths, 3,002 Sf
Photo of Listing #O5971316

2224 Venetian Way

$1,650,000
WINTER PARK
MLS® # O5971316
4 Beds, 4 Baths, 3,673 Sf
Photo of Listing #O5964472
WINTER PARK
MLS® # O5964472
4 Beds, 4 Baths, 4,080 Sf
Photo of Listing #O5956869
WINTER PARK
MLS® # O5956869
4 Beds, 4 Baths, 4,130 Sf
Photo of Listing #O5963282
WINTER PARK
MLS® # O5963282
4 Beds, 4 Baths, 3,166 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, 3,150 Sf
Photo of Listing #O5947358
Reduced 3.3%

871 Mayfield Avenue

$1,450,000
WINTER PARK
MLS® # O5947358
5 Beds, 6 Baths, 4,488 Sf
Photo of Listing #O5969244
New
WINTER PARK
MLS® # O5969244
4 Beds, 4 Baths, 3,262 Sf
Photo of Listing #O5973062
New

4559 Whimbrel Place

$1,299,950
WINTER PARK
MLS® # O5973062
5 Beds, 4 Baths, 3,385 Sf
Photo of Listing #O5949470
WINTER PARK
MLS® # O5949470
4 Beds, 5 Baths, 2,950 Sf
Photo of Listing #O5956714
Reduced 2.2%

1570 Elm Avenue

$1,295,000
WINTER PARK
MLS® # O5956714
5 Beds, 4 Baths, 3,755 Sf
Photo of Listing #O5973018
New

628 Penn Place

$1,250,000
WINTER PARK
MLS® # O5973018
4 Beds, 4 Baths, 3,356 Sf
Photo of Listing #O5968166
Reduced 3.8%

629 Penn Place

$1,250,000
WINTER PARK
MLS® # O5968166
3 Beds, 3 Baths, 3,340 Sf
Photo of Listing #O5967683
Reduced 3.8%
WINTER PARK
MLS® # O5967683
4 Beds, 4 Baths, 2,941 Sf
Photo of Listing #O5951141
Reduced 3.9%

1024 Tuscany Place

$1,225,000
WINTER PARK
MLS® # O5951141
4 Beds, 4 Baths, 3,876 Sf
Photo of Listing #O5968400

1554 Harris Circle

$1,200,000
WINTER PARK
MLS® # O5968400
3 Beds, 3 Baths, 2,801 Sf
Photo of Listing #O5826371
WINTER PARK
MLS® # O5826371
5 Beds, 4 Baths, 3,768 Sf
Photo of Listing #O5951475
Reduced 40.1%

1021 Lincoln Circle

$1,195,000
WINTER PARK
MLS® # O5951475
3 Beds, 3 Baths, 2,284 Sf
Photo of Listing #O5972271
New
WINTER PARK
MLS® # O5972271
4 Beds, 4 Baths, 3,915 Sf
Photo of Listing #O5962697
Reduced 2.1%

446 Melrose Avenue

$1,175,000
WINTER PARK
MLS® # O5962697
4 Beds, 2 Baths, 2,640 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 September 18th, 2021 at 5:34am EDT.