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

211 Properties Found. Page 1 of 5.
Photo of Listing #O6012672
WINTER PARK
MLS® # O6012672
7 Beds, 7 Baths, 12,475 Sf
Photo of Listing #O6039038
Reduced 3.2%
WINTER PARK
MLS® # O6039038
8 Beds, 10 Baths, 19,619 Sf
Photo of Listing #O6011692
Reduced 10.1%

1311 Via Tuscany

$8,950,000
WINTER PARK
MLS® # O6011692
7 Beds, 8 Baths, 10,997 Sf
Photo of Listing #O6041348
Reduced 3.7%

227 Genius Drive

$5,299,000
WINTER PARK
MLS® # O6041348
5 Beds, 7 Baths, 7,568 Sf
Photo of Listing #O6030728

870 Georgia Avenue

$4,950,000
WINTER PARK
MLS® # O6030728
5 Beds, 7 Baths, 6,010 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 #O6043192

1106 Palmer Avenue

$4,325,000
WINTER PARK
MLS® # O6043192
4 Beds, 6 Baths, 6,500 Sf
Photo of Listing #O6043840
WINTER PARK
MLS® # O6043840
5 Beds, 7 Baths, 5,035 Sf
Photo of Listing #O6058333
WINTER PARK
MLS® # O6058333
5 Beds, 6 Baths, 4,844 Sf
Photo of Listing #O6002375
Reduced 4.5%

502 Genius Drive

$3,150,000
WINTER PARK
MLS® # O6002375
6 Beds, 5 Baths, 4,735 Sf
Photo of Listing #O6034931
WINTER PARK
MLS® # O6034931
5 Beds, 7 Baths, 4,905 Sf
Photo of Listing #O5998797
WINTER PARK
MLS® # O5998797
3 Beds, 2 Baths, 1,552 Sf
Photo of Listing #O6054210
Reduced 6.4%

1466 Alabama Drive

$2,995,000
WINTER PARK
MLS® # O6054210
4 Beds, 5 Baths, 3,668 Sf
Photo of Listing #O6056060

1223 Harding Street

$2,695,000
WINTER PARK
MLS® # O6056060
4 Beds, 6 Baths, 4,309 Sf
Photo of Listing #O6058796
WINTER PARK
MLS® # O6058796
6 Beds, 6 Baths, 4,517 Sf
Photo of Listing #O6051378
WINTER PARK
MLS® # O6051378
5 Beds, 6 Baths, 4,985 Sf
Photo of Listing #O6045522

1851 Windsor Drive

$2,490,000
WINTER PARK
MLS® # O6045522
5 Beds, 7 Baths, 3,961 Sf
Photo of Listing #O6026019
Reduced 4.4%
WINTER PARK
MLS® # O6026019
4 Beds, 5 Baths, 3,617 Sf
Photo of Listing #O5996920
WINTER PARK
MLS® # O5996920
5 Beds, 7 Baths, 4,500 Sf
Photo of Listing #R4906032
Reduced 11.5%

965 Lakeview Drive

$2,300,000
WINTER PARK
MLS® # R4906032
4 Beds, 4 Baths, 2,199 Sf
Photo of Listing #O6048734
WINTER PARK
MLS® # O6048734
4 Beds, 5 Baths, 3,706 Sf
Photo of Listing #O5987208
WINTER PARK
MLS® # O5987208
5 Beds, 6 Baths, 4,214 Sf
Photo of Listing #O6026944
Reduced 4.2%

1300 Raintree Place

$2,199,000
WINTER PARK
MLS® # O6026944
5 Beds, 5 Baths, 4,295 Sf
Photo of Listing #O6060503

281 Brewer Avenue

$2,000,000
WINTER PARK
MLS® # O6060503
5 Beds, 5 Baths, 4,029 Sf
Photo of Listing #S5065768

2723 Norris Avenue

$1,999,999
WINTER PARK
MLS® # S5065768
4 Beds, 4 Baths, 3,914 Sf
Photo of Listing #O6035314

1156 Oaks Boulevard

$1,995,000
WINTER PARK
MLS® # O6035314
4 Beds, 5 Baths, 3,258 Sf
Photo of Listing #O6059682
New
WINTER PARK
MLS® # O6059682
4 Beds, 4 Baths, 3,338 Sf
Photo of Listing #O6038428
Reduced 1.5%

1531 Place Picardy

$1,950,000
WINTER PARK
MLS® # O6038428
4 Beds, 4 Baths, 3,964 Sf
Photo of Listing #O6035143

102 Bell Pl

$1,900,000
WINTER PARK
MLS® # O6035143
5 Beds, 5 Baths, 3,702 Sf
Photo of Listing #O6016484

130 Burks Circle

$1,899,000
WINTER PARK
MLS® # O6016484
4 Beds, 5 Baths, 3,733 Sf
Photo of Listing #O6045773
Reduced 5.5%

580 Palmer Avenue

$1,775,000
WINTER PARK
MLS® # O6045773
3 Beds, 3 Baths, 3,055 Sf
Photo of Listing #O5996629
Reduced 5.8%

234 Detmar Drive

$1,695,000
WINTER PARK
MLS® # O5996629
4 Beds, 5 Baths, 3,609 Sf
Photo of Listing #O5956869
WINTER PARK
MLS® # O5956869
4 Beds, 4 Baths, 4,130 Sf
Photo of Listing #O6061821
New
WINTER PARK
MLS® # O6061821
4 Beds, 4 Baths, 3,444 Sf
Photo of Listing #O6054133
WINTER PARK
MLS® # O6054133
4 Beds, 4 Baths, 3,440 Sf
Photo of Listing #O6043492
WINTER PARK
MLS® # O6043492
5 Beds, 5 Baths, 3,161 Sf
Photo of Listing #O6060012

1130 Palmer Avenue

$1,600,000
WINTER PARK
MLS® # O6060012
3 Beds, 3 Baths, 2,873 Sf
Photo of Listing #T3398325
Reduced 5.9%

780 Arjay Way

$1,599,999
WINTER PARK
MLS® # T3398325
5 Beds, 5 Baths, 3,205 Sf
Photo of Listing #O6053620

1251 Richmond Road

$1,595,000
WINTER PARK
MLS® # O6053620
3 Beds, 4 Baths, 3,613 Sf
Photo of Listing #O6036610
Reduced 7.1%

1209 Sharon Place

$1,579,000
WINTER PARK
MLS® # O6036610
4 Beds, 3 Baths, 2,079 Sf
Photo of Listing #O6027325
Reduced 1.6%

2926 Parkland Court

$1,525,000
WINTER PARK
MLS® # O6027325
4 Beds, 4 Baths, 3,132 Sf
Photo of Listing #O6052171

3580 Wilde Avenue

$1,500,000
WINTER PARK
MLS® # O6052171
6 Beds, 6 Baths, 4,367 Sf
Photo of Listing #O6052131

3520 Wilde Avenue

$1,500,000
WINTER PARK
MLS® # O6052131
6 Beds, 6 Baths, 4,367 Sf
Photo of Listing #O6047377
WINTER PARK
MLS® # O6047377
3 Beds, 3 Baths, 2,350 Sf
Photo of Listing #O6046368

1511 Palm Avenue

$1,399,000
WINTER PARK
MLS® # O6046368
4 Beds, 4 Baths, 2,460 Sf
Photo of Listing #O6043414
Reduced 4.1%

1750 Carollee Lane

$1,390,000
WINTER PARK
MLS® # O6043414
4 Beds, 4 Baths, 3,249 Sf
Photo of Listing #O6001417
Reduced 6%

910 Poinciana Lane

$1,387,000
WINTER PARK
MLS® # O6001417
4 Beds, 3 Baths, 2,008 Sf
Photo of Listing #O6011141

601 Ellen Drive

$1,349,000
WINTER PARK
MLS® # O6011141
4 Beds, 5 Baths, 2,783 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 28th, 2022 at 8:33pm EDT.