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

163 Properties Found. Page 1 of 4.
Photo of Listing #O5916191
Reduced 1.6%
Winter Park
MLS® # O5916191
4 Beds, 6 Baths, 6,690 Sf
Photo of Listing #O5910921

1001 Anchorage Ct

$5,750,000
Winter Park
MLS® # O5910921
5 Beds, 7 Baths, 9,277 Sf
Photo of Listing #O5932285
Winter Park
MLS® # O5932285
4 Beds, 6 Baths, 6,690 Sf
Photo of Listing #O5933713
New

171 Genius Dr

$4,500,000
Winter Park
MLS® # O5933713
4 Beds, 6 Baths, 5,917 Sf
Photo of Listing #O5936694
New

674 W Morse Blvd

$4,250,000
Winter Park
MLS® # O5936694
3 Beds, 5 Baths, 4,390 Sf
Photo of Listing #O5919481
Reduced 90%
Winter Park
MLS® # O5919481
3 Beds, 4 Baths, 2,363 Sf
Photo of Listing #O5930531
Winter Park
MLS® # O5930531
3 Beds, 5 Baths, 4,160 Sf
Photo of Listing #O5916871
Winter Park
MLS® # O5916871
7 Beds, 6 Baths, 4,481 Sf
Photo of Listing #O5926906

2615 Oglesby Ave

$2,600,000
Winter Park
MLS® # O5926906
7 Beds, 8 Baths, 6,700 Sf
Photo of Listing #O5922251

210 Virginia Dr

$2,600,000
Winter Park
MLS® # O5922251
5 Beds, 7 Baths, 3,749 Sf
Photo of Listing #O5921279

2219 Venetian Way

$2,550,000
Winter Park
MLS® # O5921279
6 Beds, 6 Baths, 6,362 Sf
Photo of Listing #O5921489
Winter Park
MLS® # O5921489
4 Beds, 5 Baths, 3,603 Sf
Photo of Listing #O5896286

1660 Palmer Ave

$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 #O5935243

2229 Via Tuscany

$2,395,000
Winter Park
MLS® # O5935243
5 Beds, 6 Baths, 4,456 Sf
Photo of Listing #O5924824
Reduced 3.8%
Winter Park
MLS® # O5924824
3 Beds, 4 Baths, 2,709 Sf
Photo of Listing #O5934991

515 Lake Front Blvd

$2,385,000
Winter Park
MLS® # O5934991
4 Beds, 4 Baths, 4,023 Sf
Photo of Listing #O5930523
Winter Park
MLS® # O5930523
3 Beds, 5 Baths, 3,244 Sf
Photo of Listing #O5903824

138 Detmar Dr

$2,250,000
Winter Park
MLS® # O5903824
6 Beds, 8 Baths, 5,430 Sf
Photo of Listing #O5921960

141 N Virginia Ave

$2,150,000
Winter Park
MLS® # O5921960
5 Beds, 6 Baths, 4,018 Sf
Photo of Listing #O5876425

4245 Bear Gully Rd

$2,150,000
Winter Park
MLS® # O5876425
5 Beds, 5 Baths, 5,528 Sf
Photo of Listing #O5927438
Reduced 8.7%

1319 N New York Ave

$2,095,000
Winter Park
MLS® # O5927438
5 Beds, 5 Baths, 5,292 Sf
Photo of Listing #O5917629

2156 Talman Ct

$2,075,000
Winter Park
MLS® # O5917629
5 Beds, 8 Baths, 7,762 Sf
Photo of Listing #O5921508
Reduced 7.2%

1520 Highland Rd

$1,995,000
Winter Park
MLS® # O5921508
5 Beds, 7 Baths, 4,720 Sf
Photo of Listing #O5931342

1836 Grinnell Ter

$1,950,000
Winter Park
MLS® # O5931342
5 Beds, 5 Baths, 4,308 Sf
Photo of Listing #O5925078

1016 Mckean Cir

$1,890,000
Winter Park
MLS® # O5925078
4 Beds, 5 Baths, 3,443 Sf
Photo of Listing #O5889654
Reduced 3%

1730 Greenwich Ave

$1,625,000
Winter Park
MLS® # O5889654
4 Beds, 5 Baths, 4,611 Sf
Photo of Listing #O5935762
New

1470 Place Picardy

$1,600,000
Winter Park
MLS® # O5935762
5 Beds, 6 Baths, 4,227 Sf
Photo of Listing #O5922949
Winter Park
MLS® # O5922949
3 Beds, 4 Baths, 3,118 Sf
Photo of Listing #O5899896
Reduced 6.3%
Winter Park
MLS® # O5899896
3 Beds, 4 Baths, 3,174 Sf
Photo of Listing #O5919292

1251 Richmond Rd

$1,475,000
Winter Park
MLS® # O5919292
3 Beds, 4 Baths, 3,613 Sf
Photo of Listing #O5905890
Reduced 1.8%
Winter Park
MLS® # O5905890
3 Beds, 4 Baths, 2,806 Sf
Photo of Listing #O5849798
Reduced 6.1%

1640 Palmer Ave

$1,395,000
Winter Park
MLS® # O5849798
4 Beds, 4 Baths, 4,299 Sf
Photo of Listing #O5935506
New

543 Shepherd Ave

$1,300,000
Winter Park
MLS® # O5935506
4 Beds, 4 Baths, 3,707 Sf
Photo of Listing #O5920257
Reduced 1.8%

451 W Comstock Ave

$1,275,000
Winter Park
MLS® # O5920257
4 Beds, 5 Baths, 3,549 Sf
Photo of Listing #O5892520
Reduced 3.5%

1970 Laurel Rd

$1,245,000
Winter Park
MLS® # O5892520
4 Beds, 4 Baths, 3,440 Sf
Photo of Listing #O5913456
Reduced 8.5%

1807 Barker Dr

$1,189,000
Winter Park
MLS® # O5913456
5 Beds, 3 Baths, 3,804 Sf
Photo of Listing #O5914421

2700 Wright Ave

$1,175,000
Winter Park
MLS® # O5914421
4 Beds, 5 Baths, 2,692 Sf
Photo of Listing #O5935754
New

2034 East End Ave

$1,135,000
Winter Park
MLS® # O5935754
3 Beds, 4 Baths, 2,714 Sf
Photo of Listing #O5936512
New

1651 Summerland Ave

$1,080,000
Winter Park
MLS® # O5936512
4 Beds, 3 Baths, 3,023 Sf
Photo of Listing #O5886784
Reduced 1.8%

1442 Palm Ave

$1,079,990
Winter Park
MLS® # O5886784
6 Beds, 6 Baths, 3,611 Sf
Photo of Listing #O5928937

865 W Canton Ave

$1,050,000
Winter Park
MLS® # O5928937
4 Beds, 3 Baths, 2,803 Sf
Photo of Listing #O5907204
Reduced 2.3%

453 Fletcher Pl

$1,050,000
Winter Park
MLS® # O5907204
5 Beds, 4 Baths, 3,737 Sf
Photo of Listing #O5911233
Reduced 4.5%

911 Osceola Ave

$1,049,000
Winter Park
MLS® # O5911233
3 Beds, 4 Baths, 2,244 Sf
Photo of Listing #O5927223
Reduced 1.3%

1820 Anzle Avenue

$1,025,000
Winter Park
MLS® # O5927223
4 Beds, 4 Baths, 3,289 Sf
Photo of Listing #O5936636
New

1370 Alberta Dr

$999,000
Winter Park
MLS® # O5936636
4 Beds, 6 Baths, 3,483 Sf
Photo of Listing #O5905310
Winter Park
MLS® # O5905310
5 Beds, 4 Baths, 3,257 Sf
Photo of Listing #O5927710
Winter Park
MLS® # O5927710
2 Beds, 2 Baths, 1,602 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 April 13th, 2021 at 11:17am EDT.