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

133 Properties Found. Page 1 of 3.
Photo of Listing #O5984097

1411 Via Tuscany

$15,900,000
WINTER PARK
MLS® # O5984097
5 Beds, 10 Baths, 10,734 Sf
Photo of Listing #O5984671
WINTER PARK
MLS® # O5984671
5 Beds, 7 Baths, 9,277 Sf
Photo of Listing #A4508883

1106 Palmer Avenue

$4,350,000
WINTER PARK
MLS® # A4508883
4 Beds, 6 Baths, 6,500 Sf
Photo of Listing #O5919481
WINTER PARK
MLS® # O5919481
3 Beds, 4 Baths, 2,363 Sf
Photo of Listing #O5984079
WINTER PARK
MLS® # O5984079
4 Beds, 5 Baths, 4,390 Sf
Photo of Listing #O5966216

1576 Williams Drive

$3,150,000
WINTER PARK
MLS® # O5966216
5 Beds, 7 Baths, 5,375 Sf
Photo of Listing #O5943412

1570 Bryan Avenue

$2,850,000
WINTER PARK
MLS® # O5943412
6 Beds, 7 Baths, 4,627 Sf
Photo of Listing #A4518427
WINTER PARK
MLS® # A4518427
4 Beds, 6 Baths, 9,011 Sf
Photo of Listing #O5948906

N/A

$2,500,000
WINTER PARK
MLS® # O5948906
4 Beds, 5 Baths, 4,288 Sf
Photo of Listing #O5964359

1005 Lakeview Drive

$2,250,000
WINTER PARK
MLS® # O5964359
3 Beds, 4 Baths, 2,344 Sf
Photo of Listing #O5962076
Reduced 2.4%

1741 Glencoe Road

$2,195,000
WINTER PARK
MLS® # O5962076
4 Beds, 5 Baths, 4,692 Sf
Photo of Listing #O5987208
New
WINTER PARK
MLS® # O5987208
5 Beds, 6 Baths, 4,214 Sf
Photo of Listing #V4921147
WINTER PARK
MLS® # V4921147
3 Beds, 4 Baths, 3,226 Sf
Photo of Listing #O5971616
Reduced 2.6%

450 Ololu Drive

$1,899,000
WINTER PARK
MLS® # O5971616
5 Beds, 6 Baths, 4,988 Sf
Photo of Listing #O5971275
Reduced 2.6%

1520 Mizell Avenue

$1,845,000
WINTER PARK
MLS® # O5971275
5 Beds, 5 Baths, 4,516 Sf
Photo of Listing #O5917629

2156 Talman Court

$1,825,000
WINTER PARK
MLS® # O5917629
5 Beds, 8 Baths, 7,762 Sf
Photo of Listing #O5969099
Reduced 1.4%

1780 Palmer Avenue

$1,799,000
WINTER PARK
MLS® # O5969099
4 Beds, 6 Baths, 3,542 Sf
Photo of Listing #O5982450

715 Via Bella

$1,790,000
WINTER PARK
MLS® # O5982450
4 Beds, 4 Baths, 4,328 Sf
Photo of Listing #O5986766
New

301 Beloit Avenue

$1,695,000
WINTER PARK
MLS® # O5986766
3 Beds, 3 Baths, 2,774 Sf
Photo of Listing #O5987577

1691 Palm Avenue

$1,695,000
WINTER PARK
MLS® # O5987577
4 Beds, 4 Baths, 3,075 Sf
Photo of Listing #O5971316
Reduced 3.6%

2224 Venetian Way

$1,590,000
WINTER PARK
MLS® # O5971316
4 Beds, 4 Baths, 3,673 Sf
Photo of Listing #O5976053
Reduced 1.9%

580 Ololu Drive

$1,577,700
WINTER PARK
MLS® # O5976053
3 Beds, 3 Baths, 2,812 Sf
Photo of Listing #O5963282
WINTER PARK
MLS® # O5963282
4 Beds, 4 Baths, 3,166 Sf
Photo of Listing #O5944228
WINTER PARK
MLS® # O5944228
5 Beds, 5 Baths, 3,412 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 #O5988710
New

1624 Roundelay Lane

$1,450,000
WINTER PARK
MLS® # O5988710
5 Beds, 4 Baths, 4,720 Sf
Photo of Listing #O5952901

1550 Dodd Road

$1,380,000
WINTER PARK
MLS® # O5952901
4 Beds, 6 Baths, 5,220 Sf
Photo of Listing #O5974120

1817 Dover Road

$1,360,000
WINTER PARK
MLS® # O5974120
3 Beds, 4 Baths, 3,730 Sf
Photo of Listing #O5982483
Reduced 2.9%
WINTER PARK
MLS® # O5982483
3 Beds, 3 Baths, 1,754 Sf
Photo of Listing #O5988265
New
WINTER PARK
MLS® # O5988265
4 Beds, 5 Baths, 2,732 Sf
Photo of Listing #O5949470
WINTER PARK
MLS® # O5949470
4 Beds, 5 Baths, 2,950 Sf
Photo of Listing #O5981558

1430 Aloma Avenue

$1,289,000
WINTER PARK
MLS® # O5981558
3 Beds, 3 Baths, 2,855 Sf
Photo of Listing #O5973062
Reduced 3.9%

4559 Whimbrel Place

$1,249,900
WINTER PARK
MLS® # O5973062
5 Beds, 4 Baths, 3,385 Sf
Photo of Listing #O5972895
WINTER PARK
MLS® # O5972895
5 Beds, 5 Baths, 3,200 Sf
Photo of Listing #O5975765
WINTER PARK
MLS® # O5975765
4 Beds, 4 Baths, 3,819 Sf
Photo of Listing #O5968400

1554 Harris Circle

$1,200,000
WINTER PARK
MLS® # O5968400
3 Beds, 3 Baths, 2,801 Sf
Photo of Listing #O5982558
WINTER PARK
MLS® # O5982558
2 Beds, 2 Baths, 1,514 Sf
Photo of Listing #O5981375

1880 Windsor Drive

$1,175,000
WINTER PARK
MLS® # O5981375
5 Beds, 4 Baths, 3,074 Sf
Photo of Listing #O5965932
Reduced 2.7%

1409 Chapman Circle

$1,119,000
WINTER PARK
MLS® # O5965932
3 Beds, 4 Baths, 3,043 Sf
Photo of Listing #O5973305
Reduced 4.3%
WINTER PARK
MLS® # O5973305
3 Beds, 3 Baths, 1,954 Sf
Photo of Listing #O5970012

2121 Loch Lomond

$1,099,000
WINTER PARK
MLS® # O5970012
4 Beds, 3 Baths, 2,855 Sf
Photo of Listing #A4512747
Reduced 4.4%

420 Sylvan Drive

$1,075,000
WINTER PARK
MLS® # A4512747
3 Beds, 4 Baths, 2,673 Sf
Photo of Listing #O5974338
WINTER PARK
MLS® # O5974338
2 Beds, 2 Baths, 1,599 Sf
Photo of Listing #O5988435
New
WINTER PARK
MLS® # O5988435
4 Beds, 4 Baths, 3,298 Sf
Photo of Listing #O5956929
WINTER PARK
MLS® # O5956929
3 Beds, 3 Baths, 2,319 Sf
Photo of Listing #O5947895
WINTER PARK
MLS® # O5947895
4 Beds, 4 Baths, 2,811 Sf
Photo of Listing #O5987307
WINTER PARK
MLS® # O5987307
4 Beds, 4 Baths, 3,040 Sf
Photo of Listing #O5986307

524 Lander Road

$795,000
WINTER PARK
MLS® # O5986307
3 Beds, 3 Baths, 2,718 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 December 1st, 2021 at 9:37pm EST.