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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

Winter Park Homes for Sale - Page #2

230 Properties Found. Page 2 of 5.
Photo of Listing #O6157218
Reduced 5.6%
WINTER PARK
MLS® # O6157218
3 Beds, 4 Baths, 3,112 Sf
Photo of Listing #O6154133
Reduced 5.6%

1530 Via Tuscany

$1,695,000
WINTER PARK
MLS® # O6154133
4 Beds, 4 Baths, 3,341 Sf
Photo of Listing #O6199755
New

1801 Legion Drive

$1,690,000
WINTER PARK
MLS® # O6199755
5 Beds, 5 Baths, 3,518 Sf
Photo of Listing #O6200641
New

940 Moss Lane

$1,650,000
WINTER PARK
MLS® # O6200641
5 Beds, 3 Baths, 3,233 Sf
Photo of Listing #O6174985
Reduced 4.3%

1540 Wilbar Circle

$1,650,000
WINTER PARK
MLS® # O6174985
4 Beds, 4 Baths, 3,400 Sf
Photo of Listing #O6154620
Reduced 2.7%
WINTER PARK
MLS® # O6154620
4 Beds, 5 Baths, 3,448 Sf
Photo of Listing #O6200815
New
WINTER PARK
MLS® # O6200815
5 Beds, 4 Baths, 3,028 Sf
Photo of Listing #O6147977
Reduced 5.9%
WINTER PARK
MLS® # O6147977
4 Beds, 4 Baths, 2,829 Sf
Photo of Listing #O6167429
Reduced 3.9%
WINTER PARK
MLS® # O6167429
5 Beds, 4 Baths, 4,021 Sf
Photo of Listing #O6196984
WINTER PARK
MLS® # O6196984
3 Beds, 4 Baths, 3,118 Sf
Photo of Listing #O6180611
Reduced 6.2%
WINTER PARK
MLS® # O6180611
6 Beds, 6 Baths, 6,252 Sf
Photo of Listing #O6199613
New

580 Ololu Drive

$1,489,000
WINTER PARK
MLS® # O6199613
3 Beds, 3 Baths, 2,812 Sf
Photo of Listing #V4935671

251 Dana Way

$1,400,000
WINTER PARK
MLS® # V4935671
3 Beds, 3 Baths, 1,440 Sf
Photo of Listing #O6174319
Reduced 1.1%

1361 Place Vendome

$1,385,000
WINTER PARK
MLS® # O6174319
4 Beds, 4 Baths, 3,578 Sf
Photo of Listing #O6194226
Reduced 2.9%

1880 Windsor Drive

$1,360,000
WINTER PARK
MLS® # O6194226
5 Beds, 4 Baths, 3,074 Sf
Photo of Listing #O6198447
New

1340 Heavenly Cove

$1,320,000
WINTER PARK
MLS® # O6198447
5 Beds, 4 Baths, 3,248 Sf
Photo of Listing #O6180792
WINTER PARK
MLS® # O6180792
3 Beds, 4 Baths, 2,265 Sf
Photo of Listing #O6190753
Reduced 4.4%
WINTER PARK
MLS® # O6190753
3 Beds, 3 Baths, 2,199 Sf
Photo of Listing #O6187090
Reduced 2%
WINTER PARK
MLS® # O6187090
3 Beds, 3 Baths, 2,585 Sf
Photo of Listing #O6189285
Reduced 7.7%

1718 Demetree Drive

$1,200,000
WINTER PARK
MLS® # O6189285
4 Beds, 3 Baths, 2,752 Sf
Photo of Listing #O6182619
Reduced 6.3%
WINTER PARK
MLS® # O6182619
3 Beds, 3 Baths, 2,615 Sf
Photo of Listing #O6195768
Reduced 4.9%

1203 Germaine Drive

$1,117,500
WINTER PARK
MLS® # O6195768
3 Beds, 2 Baths, 2,797 Sf
Photo of Listing #O6135942
Reduced 0.4%
WINTER PARK
MLS® # O6135942
3 Beds, 4 Baths, 2,085 Sf
Photo of Listing #O6193168
WINTER PARK
MLS® # O6193168
4 Beds, 3 Baths, 3,057 Sf
Photo of Listing #O6192592
WINTER PARK
MLS® # O6192592
3 Beds, 4 Baths, 2,245 Sf
Photo of Listing #O6179037
Reduced 4.1%
WINTER PARK
MLS® # O6179037
4 Beds, 3 Baths, 2,472 Sf
Photo of Listing #O6168879
Reduced 7%
WINTER PARK
MLS® # O6168879
4 Beds, 4 Baths, 2,610 Sf
Photo of Listing #V4935714
WINTER PARK
MLS® # V4935714
2 Beds, 1 Baths, 962 Sf
Photo of Listing #O6087546
Reduced 2.1%
WINTER PARK
MLS® # O6087546
4 Beds, 3 Baths, 2,867 Sf
Photo of Listing #T3512402
Reduced 1.1%
WINTER PARK
MLS® # T3512402
3 Beds, 3 Baths, 1,957 Sf
Photo of Listing #O6185675
WINTER PARK
MLS® # O6185675
3 Beds, 4 Baths, 2,063 Sf
Photo of Listing #O6192818
WINTER PARK
MLS® # O6192818
3 Beds, 3 Baths, 1,957 Sf
Photo of Listing #O6178122
Reduced 3.1%
WINTER PARK
MLS® # O6178122
3 Beds, 3 Baths, 1,829 Sf
Photo of Listing #O6191177
WINTER PARK
MLS® # O6191177
3 Beds, 3 Baths, 1,957 Sf
Photo of Listing #O6194284
Reduced 0.7%
WINTER PARK
MLS® # O6194284
3 Beds, 3 Baths, 2,354 Sf
Photo of Listing #O6180386
WINTER PARK
MLS® # O6180386
4 Beds, 4 Baths, 2,861 Sf
Photo of Listing #O6174101
Reduced 2.7%

1612 Neola Trail

$870,000
WINTER PARK
MLS® # O6174101
3 Beds, 3 Baths, 2,029 Sf
Photo of Listing #A4589811
Reduced 0.6%
WINTER PARK
MLS® # A4589811
3 Beds, 3 Baths, 1,957 Sf
Photo of Listing #O6183345
Reduced 5.6%
WINTER PARK
MLS® # O6183345
3 Beds, 3 Baths, 2,447 Sf
Photo of Listing #O6190685
WINTER PARK
MLS® # O6190685
2 Beds, 2 Baths, 1,351 Sf
Photo of Listing #O6178648
Reduced 2.8%
WINTER PARK
MLS® # O6178648
3 Beds, 2 Baths, 1,628 Sf
Photo of Listing #O6157948
Reduced 4.7%
WINTER PARK
MLS® # O6157948
4 Beds, 3 Baths, 2,124 Sf
Photo of Listing #O6199197
New
WINTER PARK
MLS® # O6199197
4 Beds, 4 Baths, 2,822 Sf
Photo of Listing #T3520666
WINTER PARK
MLS® # T3520666
4 Beds, 4 Baths, 2,137 Sf
Photo of Listing #O6201034
New
WINTER PARK
MLS® # O6201034
5 Beds, 4 Baths, 3,496 Sf
Photo of Listing #O6185776
Reduced 2.5%
WINTER PARK
MLS® # O6185776
3 Beds, 2 Baths, 1,715 Sf
Photo of Listing #O6195037
WINTER PARK
MLS® # O6195037
3 Beds, 2 Baths, 1,669 Sf
Photo of Listing #O6195581
WINTER PARK
MLS® # O6195581
4 Beds, 4 Baths, 3,394 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 3rd, 2024 at 4:48am EDT.