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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

216 Properties Found. Page 1 of 5.
Photo of Listing #O6183317

1210 Via Capri

$7,370,000
WINTER PARK
MLS® # O6183317
5 Beds, 7 Baths, 6,774 Sf
Photo of Listing #O6173028

2161 Sharon Road

$5,538,500
WINTER PARK
MLS® # O6173028
5 Beds, 7 Baths, 6,475 Sf
Photo of Listing #O6120809

2228 Azalea Place

$5,400,000
WINTER PARK
MLS® # O6120809
5 Beds, 6 Baths, 5,072 Sf
Photo of Listing #O6153641
Reduced 4.9%

421 Lakewood Drive

$4,995,000
WINTER PARK
MLS® # O6153641
5 Beds, 9 Baths, 5,847 Sf
Photo of Listing #O6187383
New

1444 Grove Terrace

$4,950,000
WINTER PARK
MLS® # O6187383
6 Beds, 7 Baths, 4,442 Sf
Photo of Listing #O6178451
WINTER PARK
MLS® # O6178451
3 Beds, 5 Baths, 4,237 Sf
Photo of Listing #O6154240
Reduced 5%

2379 Forrest Road

$3,795,000
WINTER PARK
MLS® # O6154240
5 Beds, 7 Baths, 4,483 Sf
Photo of Listing #O6143278
Reduced 10%
WINTER PARK
MLS® # O6143278
3 Beds, 3 Baths, 2,143 Sf
Photo of Listing #O6157505

1635 Highland Road

$3,500,000
WINTER PARK
MLS® # O6157505
5 Beds, 6 Baths, 4,325 Sf
Photo of Listing #O6183188

1255 Via Lugano

$3,499,000
WINTER PARK
MLS® # O6183188
6 Beds, 6 Baths, 4,551 Sf
Photo of Listing #O6186543
New
WINTER PARK
MLS® # O6186543
3 Beds, 4 Baths, 3,355 Sf
Photo of Listing #O6166894
Reduced 2.9%
WINTER PARK
MLS® # O6166894
5 Beds, 6 Baths, 5,066 Sf
Photo of Listing #O6179619
WINTER PARK
MLS® # O6179619
5 Beds, 7 Baths, 4,500 Sf
Photo of Listing #O6182544
WINTER PARK
MLS® # O6182544
6 Beds, 5 Baths, 4,522 Sf
Photo of Listing #O6187136
New

210 E Lake Sue

$3,141,000
WINTER PARK
MLS® # O6187136
5 Beds, 6 Baths, 4,188 Sf
Photo of Listing #O6178928
Reduced 6.3%

1254 Via Estrella

$2,950,000
WINTER PARK
MLS® # O6178928
4 Beds, 5 Baths, 3,924 Sf
Photo of Listing #O6185001
New
WINTER PARK
MLS® # O6185001
5 Beds, 5 Baths, 4,770 Sf
Photo of Listing #O6168201

1851 Windsor Drive

$2,755,000
WINTER PARK
MLS® # O6168201
5 Beds, 6 Baths, 4,000 Sf
Photo of Listing #O6172818
Reduced 0.9%

1411 Border Drive

$2,675,000
WINTER PARK
MLS® # O6172818
4 Beds, 6 Baths, 4,638 Sf
Photo of Listing #O6187903
New

1655 Barcelona Way

$2,575,000
WINTER PARK
MLS® # O6187903
5 Beds, 5 Baths, 5,429 Sf
Photo of Listing #O6174225

360 Cortland Avenue

$2,495,000
WINTER PARK
MLS® # O6174225
4 Beds, 7 Baths, 4,240 Sf
Photo of Listing #O6179918
WINTER PARK
MLS® # O6179918
3 Beds, 4 Baths, 3,074 Sf
Photo of Listing #O6177110
WINTER PARK
MLS® # O6177110
4 Beds, 4 Baths, 3,980 Sf
Photo of Listing #O6176048
Reduced 5.8%
WINTER PARK
MLS® # O6176048
6 Beds, 6 Baths, 4,182 Sf
Photo of Listing #G5077473
Reduced 1.8%

1362 Richmond Road

$2,449,000
WINTER PARK
MLS® # G5077473
5 Beds, 4 Baths, 2,925 Sf
Photo of Listing #O6173337

1130 Kenwood Avenue

$2,400,000
WINTER PARK
MLS® # O6173337
4 Beds, 5 Baths, 4,162 Sf
Photo of Listing #O6180741
New
WINTER PARK
MLS® # O6180741
4 Beds, 5 Baths, 3,897 Sf
Photo of Listing #O6169205
WINTER PARK
MLS® # O6169205
5 Beds, 6 Baths, 4,435 Sf
Photo of Listing #O6179257

451 Shepherd Ave.

$2,300,000
WINTER PARK
MLS® # O6179257
5 Beds, 5 Baths, 4,312 Sf
Photo of Listing #O6161682
Reduced 6.3%

1860 Via Contessa

$2,245,000
WINTER PARK
MLS® # O6161682
7 Beds, 6 Baths, 6,854 Sf
Photo of Listing #O6172574
WINTER PARK
MLS® # O6172574
5 Beds, 5 Baths, 2,943 Sf
Photo of Listing #V4934265
WINTER PARK
MLS® # V4934265
3 Beds, 4 Baths, 3,075 Sf
Photo of Listing #O6168950
Reduced 4.1%
WINTER PARK
MLS® # O6168950
4 Beds, 4 Baths, 4,308 Sf
Photo of Listing #O6138358

1731 Windsor Drive

$1,995,000
WINTER PARK
MLS® # O6138358
4 Beds, 4 Baths, 3,669 Sf
Photo of Listing #O6167155
Reduced 7%
WINTER PARK
MLS® # O6167155
5 Beds, 4 Baths, 3,703 Sf
Photo of Listing #O6150036
Reduced 0.2%

1800 Bryan Avenue

$1,995,000
WINTER PARK
MLS® # O6150036
4 Beds, 5 Baths, 3,361 Sf
Photo of Listing #O6181258
WINTER PARK
MLS® # O6181258
4 Beds, 4 Baths, 2,857 Sf
Photo of Listing #O6187113
New

2144 Sycamore Drive

$1,960,000
WINTER PARK
MLS® # O6187113
5 Beds, 5 Baths, 3,499 Sf
Photo of Listing #O6180987
Reduced 2.5%

1661 Hillcrest Ave

$1,899,777
WINTER PARK
MLS® # O6180987
4 Beds, 4 Baths, 3,161 Sf
Photo of Listing #O6176414
Reduced 2.8%
WINTER PARK
MLS® # O6176414
3 Beds, 4 Baths, 2,290 Sf
Photo of Listing #O6172852

1101 Kenwood Avenue

$1,875,000
WINTER PARK
MLS® # O6172852
4 Beds, 4 Baths, 2,955 Sf
Photo of Listing #O6174985
Reduced 10%

1540 Wilbar Circle

$1,800,000
WINTER PARK
MLS® # O6174985
4 Beds, 4 Baths, 3,400 Sf
Photo of Listing #O6154620
Reduced 5.3%
WINTER PARK
MLS® # O6154620
4 Beds, 5 Baths, 3,448 Sf
Photo of Listing #O6182800
WINTER PARK
MLS® # O6182800
2 Beds, 2 Baths, 2,304 Sf
Photo of Listing #O6154133
Reduced 5.3%

1530 Via Tuscany

$1,795,000
WINTER PARK
MLS® # O6154133
4 Beds, 4 Baths, 3,341 Sf
Photo of Listing #O6163891
Reduced 0.8%

1631 Lasbury Avenue

$1,779,900
WINTER PARK
MLS® # O6163891
3 Beds, 3 Baths, 2,651 Sf
Photo of Listing #O6180799
WINTER PARK
MLS® # O6180799
6 Beds, 7 Baths, 4,173 Sf
Photo of Listing #O6178427
Reduced 1.7%

1016 Tuscany Place

$1,700,000
WINTER PARK
MLS® # O6178427
5 Beds, 4 Baths, 3,151 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 March 18th, 2024 at 10:19pm EDT.