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

210 Properties Found. Page 1 of 5.
Photo of Listing #O5916191
New

55 Trismen Ter

$6,595,000
Winter Park
MLS® # O5916191
4 Beds, 6 Baths, 6,690 Sf
Photo of Listing #O5910921

1001 Anchorage Ct

$5,750,000
Winter Park
MLS® # O5910921
5 Beds, 7 Baths, 9,277 Sf
Photo of Listing #O5809404
Reduced 1.2%
Winter Park
MLS® # O5809404
10 Beds, 14 Baths, 8,325 Sf
Photo of Listing #O5902307
Winter Park
MLS® # O5902307
5 Beds, 7 Baths, 6,444 Sf
Photo of Listing #O5815144

668 W Morse Blvd

$3,485,000
Winter Park
MLS® # O5815144
4 Beds, 6 Baths, 5,819 Sf
Photo of Listing #O5808325
Reduced 4.3%

511 W Canton Ave

$3,350,000
Winter Park
MLS® # O5808325
5 Beds, 7 Baths, 8,910 Sf
Photo of Listing #O5903134

1300 N Park Ave

$3,295,000
Winter Park
MLS® # O5903134
5 Beds, 7 Baths, 6,214 Sf
Photo of Listing #O5509686
Reduced 7.1%

740 Palmer Ave

$2,950,000
Winter Park
MLS® # O5509686
5 Beds, 5 Baths, 4,810 Sf
Photo of Listing #O5911224

661 Columbia Dr

$2,795,000
Winter Park
MLS® # O5911224
4 Beds, 5 Baths, 4,349 Sf
Photo of Listing #O5918622
New
Winter Park
MLS® # O5918622
6 Beds, 6 Baths, 5,921 Sf
Photo of Listing #O5896286

1660 Palmer Ave

$2,295,000
Winter Park
MLS® # O5896286
4 Beds, 6 Baths, 5,400 Sf
Photo of Listing #O5903824

138 Detmar Dr

$2,250,000
Winter Park
MLS® # O5903824
6 Beds, 8 Baths, 5,430 Sf
Photo of Listing #O5876353
Reduced 2.1%

2400 Venetian Way

$2,150,000
Winter Park
MLS® # O5876353
5 Beds, 5 Baths, 4,293 Sf
Photo of Listing #O5876425

4245 Bear Gully Rd

$2,150,000
Winter Park
MLS® # O5876425
5 Beds, 5 Baths, 5,528 Sf
Photo of Listing #O5917629
New

2156 Talman Ct

$1,950,000
Winter Park
MLS® # O5917629
5 Beds, 8 Baths, 7,762 Sf
Photo of Listing #O5891473
Reduced 9%

280 Stirling Avenue

$1,950,000
Winter Park
MLS® # O5891473
4 Beds, 4 Baths, 3,428 Sf
Photo of Listing #O5907400

2324 Randall Rd

$1,770,000
Winter Park
MLS® # O5907400
4 Beds, 5 Baths, 4,151 Sf
Photo of Listing #O5911729
Winter Park
MLS® # O5911729
3 Beds, 4 Baths, 3,276 Sf
Photo of Listing #O5917873
New

1228 Mayfield Ave

$1,740,000
Winter Park
MLS® # O5917873
4 Beds, 4 Baths, 4,013 Sf
Photo of Listing #O5899490

2023 Venetian Way

$1,700,000
Winter Park
MLS® # O5899490
4 Beds, 4 Baths, 3,326 Sf
Photo of Listing #O5889654
Reduced 3%

1730 Greenwich Ave

$1,697,000
Winter Park
MLS® # O5889654
4 Beds, 5 Baths, 4,611 Sf
Photo of Listing #O5898157
Reduced 5.3%

1022 Mckean Cir

$1,690,000
Winter Park
MLS® # O5898157
4 Beds, 4 Baths, 4,610 Sf
Photo of Listing #O5871398
Reduced 4.1%

1731 Oakhurst Ave

$1,625,000
Winter Park
MLS® # O5871398
5 Beds, 7 Baths, 4,398 Sf
Photo of Listing #O5903632

1210 Via Capri

$1,599,000
Winter Park
MLS® # O5903632
4 Beds, 4 Baths, 3,904 Sf
Photo of Listing #O5899896
Winter Park
MLS® # O5899896
3 Beds, 4 Baths, 3,174 Sf
Photo of Listing #O5880298
Reduced 0.9%

140 E Morse Blvd #c

$1,575,000
Winter Park
MLS® # O5880298
2 Beds, 3 Baths, 2,450 Sf
Photo of Listing #O5913456
Reduced 5.2%

1807 Barker Dr

$1,540,000
Winter Park
MLS® # O5913456
5 Beds, 3 Baths, 3,804 Sf
Photo of Listing #O5918165

1637 Magnolia Ave

$1,489,000
Winter Park
MLS® # O5918165
4 Beds, 5 Baths, 3,616 Sf
Photo of Listing #O5905890
Reduced 1.3%
Winter Park
MLS® # O5905890
3 Beds, 4 Baths, 2,806 Sf
Photo of Listing #O5918975
New

2214 Via Luna

$1,425,000
Winter Park
MLS® # O5918975
4 Beds, 6 Baths, 3,667 Sf
Photo of Listing #O5916753

1750 Edwin Blvd

$1,425,000
Winter Park
MLS® # O5916753
5 Beds, 5 Baths, 4,108 Sf
Photo of Listing #O5849798
Reduced 6.1%

1640 Palmer Ave

$1,395,000
Winter Park
MLS® # O5849798
4 Beds, 4 Baths, 4,299 Sf
Photo of Listing #O5914456

1640 Hillcrest Ave

$1,385,000
Winter Park
MLS® # O5914456
4 Beds, 5 Baths, 3,050 Sf
Photo of Listing #O5902548

511 Fairfax Ave

$1,375,000
Winter Park
MLS® # O5902548
4 Beds, 3 Baths, 3,463 Sf
Photo of Listing #O5910773

4355 Gabriella Ln

$1,340,000
Winter Park
MLS® # O5910773
4 Beds, 3 Baths, 2,620 Sf
Photo of Listing #O5908014
Reduced 7.1%

1205 Mayfield Ave

$1,300,000
Winter Park
MLS® # O5908014
6 Beds, 5 Baths, 3,948 Sf
Photo of Listing #O5883686

1555 Granville Dr

$1,299,000
Winter Park
MLS® # O5883686
4 Beds, 3 Baths, 3,634 Sf
Photo of Listing #O5916069

1601 Legion Dr

$1,295,000
Winter Park
MLS® # O5916069
3 Beds, 4 Baths, 2,281 Sf
Photo of Listing #O5914997

2206 Venetian Way

$1,295,000
Winter Park
MLS® # O5914997
5 Beds, 4 Baths, 4,701 Sf
Photo of Listing #O5898624
Reduced 3.7%

1650 Dale Ave

$1,295,000
Winter Park
MLS® # O5898624
4 Beds, 5 Baths, 4,577 Sf
Photo of Listing #O5892520
Reduced 0.8%

1970 Laurel Rd

$1,290,000
Winter Park
MLS® # O5892520
4 Beds, 4 Baths, 3,440 Sf
Photo of Listing #O5894524

1080 Kenwood Ave

$1,250,000
Winter Park
MLS® # O5894524
4 Beds, 4 Baths, 3,317 Sf
Photo of Listing #O5903269
New

2174 Talman Ct

$1,195,000
Winter Park
MLS® # O5903269
4 Beds, 5 Baths, 4,998 Sf
Photo of Listing #O5917041

467 Carolina Ave

$1,195,000
Winter Park
MLS® # O5917041
4 Beds, 3 Baths, 2,710 Sf
Photo of Listing #O5911311

1437 Chapman Cir

$1,195,000
Winter Park
MLS® # O5911311
5 Beds, 4 Baths, 3,732 Sf
Photo of Listing #O5914421

2700 Wright Ave

$1,125,000
Winter Park
MLS® # O5914421
4 Beds, 5 Baths, 2,692 Sf
Photo of Listing #O5911233

911 Osceola Ave

$1,125,000
Winter Park
MLS® # O5911233
3 Beds, 4 Baths, 2,244 Sf
Photo of Listing #O5878089

2728 Eastern Pkwy

$1,100,000
Winter Park
MLS® # O5878089
3 Beds, 4 Baths, 2,833 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 January 24th, 2021 at 3:30pm EST.