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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

159 Properties Found. Page 1 of 4.
Photo of Listing #O6012672
WINTER PARK
MLS® # O6012672
7 Beds, 7 Baths, 12,475 Sf
Photo of Listing #O6039038
Reduced 11.9%
WINTER PARK
MLS® # O6039038
8 Beds, 10 Baths, 19,619 Sf
Photo of Listing #O6011692
Reduced 11.7%

1311 Via Tuscany

$7,900,000
WINTER PARK
MLS® # O6011692
7 Beds, 8 Baths, 10,997 Sf
Photo of Listing #O6071285

785 Via Lombardy

$5,650,000
WINTER PARK
MLS® # O6071285
5 Beds, 7 Baths, 6,736 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 #O6082781
WINTER PARK
MLS® # O6082781
4 Beds, 5 Baths, 4,901 Sf
Photo of Listing #O6082393
Reduced 3.7%

1290 Park Ave

$4,575,000
WINTER PARK
MLS® # O6082393
4 Beds, 5 Baths, 3,823 Sf
Photo of Listing #O6043192

1106 Palmer Avenue

$4,325,000
WINTER PARK
MLS® # O6043192
4 Beds, 6 Baths, 6,256 Sf
Photo of Listing #O6080006
WINTER PARK
MLS® # O6080006
4 Beds, 6 Baths, 5,819 Sf
Photo of Listing #O6084698
WINTER PARK
MLS® # O6084698
4 Beds, 7 Baths, 7,226 Sf
Photo of Listing #O6086964
New

2138 Lake Drive

$3,295,000
WINTER PARK
MLS® # O6086964
4 Beds, 4 Baths, 5,100 Sf
Photo of Listing #O6064908
Reduced 5.8%
WINTER PARK
MLS® # O6064908
6 Beds, 5 Baths, 4,522 Sf
Photo of Listing #O6034931
WINTER PARK
MLS® # O6034931
5 Beds, 7 Baths, 4,905 Sf
Photo of Listing #O6032132
Reduced 6.3%
WINTER PARK
MLS® # O6032132
4 Beds, 7 Baths, 4,014 Sf
Photo of Listing #O6032986
Reduced 17.1%
WINTER PARK
MLS® # O6032986
5 Beds, 5 Baths, 6,452 Sf
Photo of Listing #S5075342
WINTER PARK
MLS® # S5075342
4 Beds, 4 Baths, 3,500 Sf
Photo of Listing #O6081597
WINTER PARK
MLS® # O6081597
4 Beds, 5 Baths, 4,288 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 #O6058796
WINTER PARK
MLS® # O6058796
6 Beds, 6 Baths, 4,517 Sf
Photo of Listing #O6084405
WINTER PARK
MLS® # O6084405
3 Beds, 4 Baths, 3,286 Sf
Photo of Listing #O6045522

1851 Windsor Drive

$2,490,000
WINTER PARK
MLS® # O6045522
5 Beds, 7 Baths, 3,961 Sf
Photo of Listing #S5075338

1318 Morton Road

$2,360,000
WINTER PARK
MLS® # S5075338
4 Beds, 4 Baths, 2,579 Sf
Photo of Listing #O6086002
WINTER PARK
MLS® # O6086002
5 Beds, 6 Baths, 4,230 Sf
Photo of Listing #O6081797

2723 Norris Avenue

$2,199,999
WINTER PARK
MLS® # O6081797
4 Beds, 4 Baths, 4,000 Sf
Photo of Listing #O6026019
Reduced 10.6%
WINTER PARK
MLS® # O6026019
4 Beds, 5 Baths, 3,617 Sf
Photo of Listing #O6078219
WINTER PARK
MLS® # O6078219
4 Beds, 4 Baths, 3,502 Sf
Photo of Listing #O6035143

102 Bell Pl

$1,900,000
WINTER PARK
MLS® # O6035143
5 Beds, 5 Baths, 3,702 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 #O6088081
New

1531 Place Picardy

$1,895,000
WINTER PARK
MLS® # O6088081
4 Beds, 4 Baths, 3,964 Sf
Photo of Listing #O6080463
Reduced 2.4%

266 Detmar Drive

$1,850,000
WINTER PARK
MLS® # O6080463
4 Beds, 5 Baths, 3,805 Sf
Photo of Listing #O6072590
WINTER PARK
MLS® # O6072590
5 Beds, 6 Baths, 4,014 Sf
Photo of Listing #O6067141
Reduced 2.8%

1166 Oaks Boulevard

$1,750,000
WINTER PARK
MLS® # O6067141
4 Beds, 4 Baths, 2,812 Sf
Photo of Listing #O6081800

450 Ololu Drive

$1,699,000
WINTER PARK
MLS® # O6081800
5 Beds, 6 Baths, 4,518 Sf
Photo of Listing #O6075542

2234 Via Luna

$1,650,000
WINTER PARK
MLS® # O6075542
4 Beds, 4 Baths, 3,222 Sf
Photo of Listing #O6087707
New
WINTER PARK
MLS® # O6087707
4 Beds, 5 Baths, 4,625 Sf
Photo of Listing #O5996629
Reduced 4.1%

234 Detmar Drive

$1,625,000
WINTER PARK
MLS® # O5996629
4 Beds, 5 Baths, 3,609 Sf
Photo of Listing #O6060012

1130 Palmer Avenue

$1,600,000
WINTER PARK
MLS® # O6060012
3 Beds, 3 Baths, 2,873 Sf
Photo of Listing #O6071710
WINTER PARK
MLS® # O6071710
3 Beds, 3 Baths, 1,998 Sf
Photo of Listing #O6036610
Reduced 7.1%

1209 Sharon Place

$1,579,000
WINTER PARK
MLS® # O6036610
4 Beds, 3 Baths, 2,079 Sf
Photo of Listing #O6061821
Reduced 2.8%
WINTER PARK
MLS® # O6061821
4 Beds, 4 Baths, 3,444 Sf
Photo of Listing #O6052131

3520 Wilde Avenue

$1,500,000
WINTER PARK
MLS® # O6052131
6 Beds, 6 Baths, 4,367 Sf
Photo of Listing #O6084616

580 Ololu Drive

$1,495,000
WINTER PARK
MLS® # O6084616
3 Beds, 3 Baths, 2,812 Sf
Photo of Listing #O6087704
New

1016 Tuscany Place

$1,479,000
WINTER PARK
MLS® # O6087704
5 Beds, 4 Baths, 3,151 Sf
Photo of Listing #O6079806

1913 Sycamore Drive

$1,475,000
WINTER PARK
MLS® # O6079806
4 Beds, 5 Baths, 3,130 Sf
Photo of Listing #O6046368

1511 Palm Avenue

$1,399,000
WINTER PARK
MLS® # O6046368
4 Beds, 4 Baths, 2,460 Sf
Photo of Listing #O6011141

601 Ellen Drive

$1,399,000
WINTER PARK
MLS® # O6011141
4 Beds, 5 Baths, 2,783 Sf
Photo of Listing #O6070364
Reduced 2.1%

776 Mcintyre Avenue

$1,380,000
WINTER PARK
MLS® # O6070364
3 Beds, 4 Baths, 2,465 Sf
Photo of Listing #O6024210
WINTER PARK
MLS® # O6024210
4 Beds, 4 Baths, 2,700 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 February 6th, 2023 at 1:04pm EST.