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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

259 Properties Found. Page 1 of 6.
Photo of Listing #O6199109

181 Virginia Drive

$11,795,000
WINTER PARK
MLS® # O6199109
5 Beds, 8 Baths, 8,188 Sf
Photo of Listing #O6183317

1210 Via Capri

$7,370,000
WINTER PARK
MLS® # O6183317
6 Beds, 7 Baths, 6,774 Sf
Photo of Listing #O6206309
New
WINTER PARK
MLS® # O6206309
4 Beds, 5 Baths, 4,581 Sf
Photo of Listing #O6156666
WINTER PARK
MLS® # O6156666
5 Beds, 7 Baths, 9,075 Sf
Photo of Listing #O6195529
Reduced 4.9%

1761 Pinetree Road

$6,650,000
WINTER PARK
MLS® # O6195529
5 Beds, 6 Baths, 4,792 Sf
Photo of Listing #O6173028

2161 Sharon Road

$5,566,500
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 #O6203847

1135 Lakeview Drive

$5,200,000
WINTER PARK
MLS® # O6203847
5 Beds, 5 Baths, 5,681 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 #O6199601
WINTER PARK
MLS® # O6199601
5 Beds, 6 Baths, 5,320 Sf
Photo of Listing #O6193386

985 Lincoln Circle

$4,250,000
WINTER PARK
MLS® # O6193386
5 Beds, 7 Baths, 3,660 Sf
Photo of Listing #O6199396

861 Bonita Drive

$4,150,000
WINTER PARK
MLS® # O6199396
6 Beds, 8 Baths, 6,939 Sf
Photo of Listing #O6152759
Reduced 2.1%

1391 Richmond Road

$4,130,000
WINTER PARK
MLS® # O6152759
4 Beds, 6 Baths, 4,635 Sf
Photo of Listing #O6191966

1820 Glencoe Road

$3,890,000
WINTER PARK
MLS® # O6191966
5 Beds, 7 Baths, 4,055 Sf
Photo of Listing #O6201756
WINTER PARK
MLS® # O6201756
4 Beds, 5 Baths, 5,159 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 #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 #O6143278
Reduced 8.4%
WINTER PARK
MLS® # O6143278
3 Beds, 3 Baths, 2,143 Sf
Photo of Listing #O6166894
Reduced 5.9%
WINTER PARK
MLS® # O6166894
5 Beds, 6 Baths, 5,066 Sf
Photo of Listing #O6187136

210 E Lake Sue

$3,141,000
WINTER PARK
MLS® # O6187136
5 Beds, 6 Baths, 4,188 Sf
Photo of Listing #O6203301
WINTER PARK
MLS® # O6203301
4 Beds, 5 Baths, 3,576 Sf
Photo of Listing #O6196961
Reduced 3.2%
WINTER PARK
MLS® # O6196961
5 Beds, 6 Baths, 4,216 Sf
Photo of Listing #O6182544
Reduced 5.6%
WINTER PARK
MLS® # O6182544
6 Beds, 5 Baths, 4,522 Sf
Photo of Listing #O6185001
WINTER PARK
MLS® # O6185001
5 Beds, 5 Baths, 4,770 Sf
Photo of Listing #O6206511
New
WINTER PARK
MLS® # O6206511
5 Beds, 7 Baths, 4,500 Sf
Photo of Listing #O6190641

1741 Glencoe Road

$2,749,000
WINTER PARK
MLS® # O6190641
4 Beds, 5 Baths, 4,692 Sf
Photo of Listing #O6168201
Reduced 2%

1851 Windsor Drive

$2,699,000
WINTER PARK
MLS® # O6168201
5 Beds, 6 Baths, 4,000 Sf
Photo of Listing #O6202078

1791 Taylor Avenue

$2,650,000
WINTER PARK
MLS® # O6202078
5 Beds, 6 Baths, 3,731 Sf
Photo of Listing #O6198338

1161 Lincoln Circle

$2,495,000
WINTER PARK
MLS® # O6198338
4 Beds, 4 Baths, 3,154 Sf
Photo of Listing #O6172818
Reduced 2%

1411 Border Drive

$2,475,000
WINTER PARK
MLS® # O6172818
4 Beds, 6 Baths, 4,638 Sf
Photo of Listing #O6176048
Reduced 5.8%
WINTER PARK
MLS® # O6176048
6 Beds, 6 Baths, 4,182 Sf
Photo of Listing #O6177110
WINTER PARK
MLS® # O6177110
4 Beds, 4 Baths, 3,989 Sf
Photo of Listing #O6202216
New
WINTER PARK
MLS® # O6202216
5 Beds, 5 Baths, 3,640 Sf
Photo of Listing #O6179257
Reduced 2.2%

451 Shepherd Ave.

$2,250,000
WINTER PARK
MLS® # O6179257
5 Beds, 5 Baths, 4,312 Sf
Photo of Listing #O6192372
Reduced 2.2%
WINTER PARK
MLS® # O6192372
4 Beds, 4 Baths, 3,276 Sf
Photo of Listing #O6190102
WINTER PARK
MLS® # O6190102
5 Beds, 4 Baths, 3,971 Sf
Photo of Listing #O6206386
New
WINTER PARK
MLS® # O6206386
3 Beds, 4 Baths, 3,027 Sf
Photo of Listing #O6181050
Reduced 4.4%

820 Mayfield Avenue

$2,150,000
WINTER PARK
MLS® # O6181050
4 Beds, 3 Baths, 3,102 Sf
Photo of Listing #V4934265
Reduced 6.8%
WINTER PARK
MLS® # V4934265
3 Beds, 4 Baths, 3,075 Sf
Photo of Listing #O6173337
Reduced 9.1%

1130 Kenwood Avenue

$2,000,000
WINTER PARK
MLS® # O6173337
4 Beds, 5 Baths, 4,162 Sf
Photo of Listing #G5077473
Reduced 9.3%

1362 Richmond Road

$1,995,000
WINTER PARK
MLS® # G5077473
5 Beds, 4 Baths, 2,925 Sf
Photo of Listing #O6181258
WINTER PARK
MLS® # O6181258
4 Beds, 4 Baths, 2,857 Sf
Photo of Listing #O6187113

2144 Sycamore Drive

$1,960,000
WINTER PARK
MLS® # O6187113
5 Beds, 5 Baths, 3,499 Sf
Photo of Listing #O6199494
WINTER PARK
MLS® # O6199494
4 Beds, 4 Baths, 2,701 Sf
Photo of Listing #O6205484
New

1540 Palm Avenue

$1,895,000
WINTER PARK
MLS® # O6205484
5 Beds, 4 Baths, 3,423 Sf
Photo of Listing #O6203731

1181 Via Capri

$1,895,000
WINTER PARK
MLS® # O6203731
3 Beds, 3 Baths, 3,653 Sf
Photo of Listing #O6202026

1250 Via Capri

$1,895,000
WINTER PARK
MLS® # O6202026
3 Beds, 3 Baths, 3,217 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 23rd, 2024 at 4:50pm EDT.