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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

150 Properties Found. Page 1 of 4.
Photo of Listing #O6012672
WINTER PARK
MLS® # O6012672
7 Beds, 7 Baths, 12,475 Sf
Photo of Listing #O6112070

1461 Via Tuscany

$16,000,000
WINTER PARK
MLS® # O6112070
5 Beds, 6 Baths, 8,353 Sf
Photo of Listing #O6095179

4 Isle Of Sicily

$10,950,000
WINTER PARK
MLS® # O6095179
5 Beds, 8 Baths, 9,522 Sf
Photo of Listing #O6039038
Reduced 11.9%
WINTER PARK
MLS® # O6039038
8 Beds, 10 Baths, 19,619 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 #O6104175
Reduced 9.1%

671 Via Lugano

$4,500,000
WINTER PARK
MLS® # O6104175
6 Beds, 9 Baths, 7,048 Sf
Photo of Listing #O6094004
Reduced 5.2%

466 Henkel Circle

$4,500,000
WINTER PARK
MLS® # O6094004
4 Beds, 5 Baths, 4,416 Sf
Photo of Listing #O6080006
WINTER PARK
MLS® # O6080006
4 Beds, 6 Baths, 5,819 Sf
Photo of Listing #O6102003

1106 Palmer Avenue

$4,250,000
WINTER PARK
MLS® # O6102003
4 Beds, 6 Baths, 6,256 Sf
Photo of Listing #O6034151
Reduced 4.6%

2056 Lake Drive

$3,999,999
WINTER PARK
MLS® # O6034151
5 Beds, 6 Baths, 5,907 Sf
Photo of Listing #O6092523
WINTER PARK
MLS® # O6092523
3 Beds, 5 Baths, 4,237 Sf
Photo of Listing #O6111531
WINTER PARK
MLS® # O6111531
5 Beds, 7 Baths, 5,475 Sf
Photo of Listing #O6113652
New

2080 Sharon Road

$3,595,000
WINTER PARK
MLS® # O6113652
4 Beds, 5 Baths, 4,080 Sf
Photo of Listing #O6098024
Reduced 10.3%

526 Genius Drive

$3,500,000
WINTER PARK
MLS® # O6098024
4 Beds, 5 Baths, 6,390 Sf
Photo of Listing #O6108900

617 Penn Place

$3,495,000
WINTER PARK
MLS® # O6108900
4 Beds, 5 Baths, 4,932 Sf
Photo of Listing #O6092664

1150 Via Salerno

$3,495,000
WINTER PARK
MLS® # O6092664
4 Beds, 5 Baths, 3,826 Sf
Photo of Listing #O6107391
Reduced 3.8%

1271 Via Capri

$3,150,000
WINTER PARK
MLS® # O6107391
5 Beds, 6 Baths, 4,455 Sf
Photo of Listing #O6086964
Reduced 7.4%

2138 Lake Drive

$3,050,000
WINTER PARK
MLS® # O6086964
4 Beds, 4 Baths, 5,100 Sf
Photo of Listing #O6108633
WINTER PARK
MLS® # O6108633
4 Beds, 4 Baths, 3,985 Sf
Photo of Listing #O6106374

1741 Glencoe Road

$2,850,000
WINTER PARK
MLS® # O6106374
4 Beds, 5 Baths, 4,692 Sf
Photo of Listing #O6081597
WINTER PARK
MLS® # O6081597
4 Beds, 5 Baths, 4,288 Sf
Photo of Listing #O6096452
Reduced 6.8%
WINTER PARK
MLS® # O6096452
4 Beds, 4 Baths, 3,680 Sf
Photo of Listing #O6032132
Reduced 5%
WINTER PARK
MLS® # O6032132
4 Beds, 7 Baths, 4,014 Sf
Photo of Listing #O6109071

1840 Via Genoa

$2,650,000
WINTER PARK
MLS® # O6109071
4 Beds, 5 Baths, 4,120 Sf
Photo of Listing #O6068470

2172 Temple Drive

$2,650,000
WINTER PARK
MLS® # O6068470
5 Beds, 4 Baths, 3,507 Sf
Photo of Listing #O6111525
WINTER PARK
MLS® # O6111525
5 Beds, 7 Baths, 4,500 Sf
Photo of Listing #O6088994
Reduced 3.8%
WINTER PARK
MLS® # O6088994
5 Beds, 5 Baths, 4,191 Sf
Photo of Listing #G5069117
New

2156 Talman Court

$2,495,000
WINTER PARK
MLS® # G5069117
5 Beds, 8 Baths, 7,762 Sf
Photo of Listing #O6089598
Reduced 9.2%
WINTER PARK
MLS® # O6089598
3 Beds, 5 Baths, 3,244 Sf
Photo of Listing #O6094313
WINTER PARK
MLS® # O6094313
3 Beds, 4 Baths, 3,286 Sf
Photo of Listing #O6110772

2819 Parkland Drive

$2,395,000
WINTER PARK
MLS® # O6110772
4 Beds, 5 Baths, 3,995 Sf
Photo of Listing #O6103545

1022 Mckean Circle

$2,395,000
WINTER PARK
MLS® # O6103545
4 Beds, 4 Baths, 4,610 Sf
Photo of Listing #S5085738
New

1460 Sunset Drive

$2,299,000
WINTER PARK
MLS® # S5085738
5 Beds, 3 Baths, 3,155 Sf
Photo of Listing #O6112581
WINTER PARK
MLS® # O6112581
5 Beds, 5 Baths, 3,850 Sf
Photo of Listing #O6112887
WINTER PARK
MLS® # O6112887
3 Beds, 4 Baths, 3,027 Sf
Photo of Listing #O6103519
WINTER PARK
MLS® # O6103519
4 Beds, 4 Baths, 4,318 Sf
Photo of Listing #O6103239
WINTER PARK
MLS® # O6103239
7 Beds, 6 Baths, 4,517 Sf
Photo of Listing #O6081797
Reduced 1.1%

2723 Norris Avenue

$2,175,000
WINTER PARK
MLS® # O6081797
4 Beds, 4 Baths, 4,000 Sf
Photo of Listing #O6109944

1461 Palm Avenue

$2,100,000
WINTER PARK
MLS® # O6109944
4 Beds, 5 Baths, 3,436 Sf
Photo of Listing #O6030728
Reduced 3.7%

870 Georgia Avenue

$2,095,000
WINTER PARK
MLS® # O6030728
3 Beds, 3 Baths, 2,709 Sf
Photo of Listing #O6103790
Reduced 4.8%
WINTER PARK
MLS® # O6103790
3 Beds, 4 Baths, 2,903 Sf
Photo of Listing #O6108514
WINTER PARK
MLS® # O6108514
4 Beds, 5 Baths, 3,617 Sf
Photo of Listing #O6088081

1531 Place Picardy

$1,895,000
WINTER PARK
MLS® # O6088081
4 Beds, 4 Baths, 3,964 Sf
Photo of Listing #O6103005
WINTER PARK
MLS® # O6103005
6 Beds, 6 Baths, 6,252 Sf
Photo of Listing #O6064031
Reduced 23.4%
WINTER PARK
MLS® # O6064031
3 Beds, 2 Baths, 1,552 Sf
Photo of Listing #O6104853
WINTER PARK
MLS® # O6104853
3 Beds, 4 Baths, 3,778 Sf
Photo of Listing #O6113129
WINTER PARK
MLS® # O6113129
5 Beds, 4 Baths, 3,853 Sf
Photo of Listing #O6113882
New

1640 Mayfield Ave

$1,725,000
WINTER PARK
MLS® # O6113882
3 Beds, 3 Baths, 2,907 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 June 3rd, 2023 at 6:19am EDT.