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

123 Properties Found. Page 1 of 3.
Photo of Listing #O6012672
WINTER PARK
MLS® # O6012672
7 Beds, 7 Baths, 12,475 Sf
Photo of Listing #O6011692
Reduced 5.2%

1311 Via Tuscany

$9,950,000
WINTER PARK
MLS® # O6011692
7 Beds, 8 Baths, 10,997 Sf
Photo of Listing #O5992925

227 Genius Drive

$5,600,000
WINTER PARK
MLS® # O5992925
5 Beds, 7 Baths, 7,568 Sf
Photo of Listing #O5999333
Reduced 8.7%

231 Chelton Circle

$5,500,000
WINTER PARK
MLS® # O5999333
5 Beds, 7 Baths, 5,754 Sf
Photo of Listing #O6001762
Reduced 3.3%

699 Osceola Avenue

$4,495,000
WINTER PARK
MLS® # O6001762
5 Beds, 4 Baths, 5,062 Sf
Photo of Listing #O6020788

1131 Via Lugano

$3,650,000
WINTER PARK
MLS® # O6020788
4 Beds, 5 Baths, 5,701 Sf
Photo of Listing #O6002375
Reduced 6%

502 Genius Drive

$3,450,000
WINTER PARK
MLS® # O6002375
6 Beds, 5 Baths, 4,735 Sf
Photo of Listing #O6019508

200 Oakwood Way

$3,275,000
WINTER PARK
MLS® # O6019508
5 Beds, 6 Baths, 4,370 Sf
Photo of Listing #O6012106
WINTER PARK
MLS® # O6012106
8 Beds, 6 Baths, 6,090 Sf
Photo of Listing #O6025012
New

1635 Highland Road

$2,890,000
WINTER PARK
MLS® # O6025012
5 Beds, 6 Baths, 4,325 Sf
Photo of Listing #O6022155
New

1215 Via Salerno

$2,800,000
WINTER PARK
MLS® # O6022155
4 Beds, 5 Baths, 3,669 Sf
Photo of Listing #O6026019
New
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 #O6018904

1109 Oaks Blvd

$2,300,000
WINTER PARK
MLS® # O6018904
5 Beds, 6 Baths, 3,731 Sf
Photo of Listing #O6022861
New

100 Stirling Avenue

$2,250,000
WINTER PARK
MLS® # O6022861
5 Beds, 4 Baths, 4,038 Sf
Photo of Listing #O5987208
WINTER PARK
MLS® # O5987208
5 Beds, 6 Baths, 4,214 Sf
Photo of Listing #O6024048
WINTER PARK
MLS® # O6024048
5 Beds, 5 Baths, 3,523 Sf
Photo of Listing #O5903824
Reduced 5%

138 Detmar Drive

$1,995,000
WINTER PARK
MLS® # O5903824
6 Beds, 8 Baths, 5,430 Sf
Photo of Listing #O6009501
WINTER PARK
MLS® # O6009501
5 Beds, 6 Baths, 4,014 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 #O6004320

2036 Via Tuscany

$1,795,000
WINTER PARK
MLS® # O6004320
3 Beds, 2 Baths, 2,148 Sf
Photo of Listing #O6025150
New
WINTER PARK
MLS® # O6025150
5 Beds, 5 Baths, 3,721 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 #O6001417
Reduced 2.9%

910 Poinciana Lane

$1,650,000
WINTER PARK
MLS® # O6001417
4 Beds, 3 Baths, 2,008 Sf
Photo of Listing #O5971616
Reduced 8.4%

450 Ololu Drive

$1,649,000
WINTER PARK
MLS® # O5971616
5 Beds, 6 Baths, 4,988 Sf
Photo of Listing #O6024871
New

1550 Elm Ave

$1,595,000
WINTER PARK
MLS® # O6024871
5 Beds, 5 Baths, 3,466 Sf
Photo of Listing #O5963282
WINTER PARK
MLS® # O5963282
4 Beds, 4 Baths, 3,166 Sf
Photo of Listing #O6019908
Reduced 11.2%

1731 Windsor Drive

$1,500,000
WINTER PARK
MLS® # O6019908
4 Beds, 4 Baths, 3,669 Sf
Photo of Listing #O6018130
WINTER PARK
MLS® # O6018130
2 Beds, 3 Baths, 2,750 Sf
Photo of Listing #O6002105
Reduced 3.2%

645 Pansy Avenue

$1,499,000
WINTER PARK
MLS® # O6002105
4 Beds, 5 Baths, 3,661 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 #O6020934
WINTER PARK
MLS® # O6020934
2 Beds, 2 Baths, 1,605 Sf
Photo of Listing #O6011141

601 Ellen Drive

$1,299,000
WINTER PARK
MLS® # O6011141
4 Beds, 5 Baths, 2,783 Sf
Photo of Listing #O5994313

603 Ellen Drive

$1,250,000
WINTER PARK
MLS® # O5994313
4 Beds, 5 Baths, 2,830 Sf
Photo of Listing #O5968400

1554 Harris Circle

$1,225,000
WINTER PARK
MLS® # O5968400
3 Beds, 3 Baths, 2,801 Sf
Photo of Listing #O6010529
New

1404 Border Drive

$1,200,000
WINTER PARK
MLS® # O6010529
4 Beds, 4 Baths, 2,505 Sf
Photo of Listing #O5970883
WINTER PARK
MLS® # O5970883
4 Beds, 5 Baths, 2,933 Sf
Photo of Listing #O6019082
WINTER PARK
MLS® # O6019082
3 Beds, 4 Baths, 2,843 Sf
Photo of Listing #O6025064
New
WINTER PARK
MLS® # O6025064
4 Beds, 4 Baths, 2,540 Sf
Photo of Listing #O6020176
WINTER PARK
MLS® # O6020176
5 Beds, 4 Baths, 2,400 Sf
Photo of Listing #O6024132
New
WINTER PARK
MLS® # O6024132
5 Beds, 4 Baths, 2,710 Sf
Photo of Listing #O6016347
WINTER PARK
MLS® # O6016347
3 Beds, 3 Baths, 1,954 Sf
Photo of Listing #O6025466
New

2149 Lake Drive

$899,000
WINTER PARK
MLS® # O6025466
4 Beds, 3 Baths, 2,110 Sf
Photo of Listing #O6005755
WINTER PARK
MLS® # O6005755
3 Beds, 4 Baths, 2,085 Sf
Photo of Listing #O6023652
Reduced 2.9%
WINTER PARK
MLS® # O6023652
4 Beds, 2 Baths, 2,369 Sf
Photo of Listing #O6023632
New

27 Stymie Place

$805,000
WINTER PARK
MLS® # O6023632
5 Beds, 3 Baths, 2,327 Sf
Photo of Listing #O6020681

25 Stymie Place

$805,000
WINTER PARK
MLS® # O6020681
5 Beds, 3 Baths, 2,327 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 May 19th, 2022 at 1:34pm EDT.