Winter Park FL Homes & Real Estate

Welcome to Winter Park, FL, a treasure trove of enriching experiences that promises an exceptional lifestyle. Embark on the Chain of Lakes Boat Tour, a delightful journey through serene waters that unveils the city's scenic natural beauty. Immerse yourself in the legacy of Rollins College, where the spirit of Mr. Rogers himself once graced the campus. Stroll down the charming brick streets, adorned with Spanish moss and centuries-old trees, creating an enchanting atmosphere. Elevate your family's future with an A-rated school system, ensuring a top-tier education. Embrace the historical charm of a New England-style downtown that keeps timeless traditions alive through holiday parades and High School Homecoming festivities. Delight in the luxury of Park Ave Shopping and Five Star Dining, offering a lifestyle that marries sophistication with comfort. Winter Park invites you to a life enriched by history, culture, education, and the finer things that make every day exceptional.

Included below are homes for sale and real estate in Winter Park, FL. If you would like more information on any of these Winter Park real estate listings, just click on a property to access the full details. From there, you can request more information or schedule a tour. And we'd be happy to provide you with disclosures, past sales history, dates and prices of properties which have recently sold nearby, and more, so just let us know how we can help!

And, for your convenience, feel free to register for a free account to receive email alerts whenever new Winter Park listings come on the market that match your specific criteria.

Winter Park April 19, 2024
249
Listed
67
Avg. DOM
$399.20
Avg. $ / Sq.Ft.
$599,000
Med. List Price
249 Properties
Page 1 of 21
$185,000
Neighborhood: Whisperwood Condo 02
2
Beds
2
Baths
774
Sq.Ft.
1983
Year Built
1
Day on Site
S5102442
MLS
$1,895,000
Neighborhood: Osceola Shores Sec 01
4
Beds
3F11/2
Baths
3,504
Sq.Ft.
1999
Year Built
1
Day on Site
O6197555
MLS
Open 4/20
1340 Chestnut Ave Winter Park,  FL 32789
$2,450,000
Neighborhood: Lake Knowles Terrace
6
Beds
5F11/2
Baths
4,182
Sq.Ft.
1963
Year Built
1
Day on Site
O6176048
MLS
$1,800,000
Neighborhood: Lugano Terrace
4
Beds
3F21/2
Baths
3,404
Sq.Ft.
1990
Year Built
1
Day on Site
O6197726
MLS
$4,250,000
Neighborhood: Robert Dhu Macdonald Park
5
Beds
5F21/2
Baths
3,660
Sq.Ft.
1951
Year Built
1
Day on Site
O6193386
MLS
Open 4/20
2821 Little John Rd Winter Park,  FL 32792
$550,000
Neighborhood: Winter Park Pines
4
Beds
2
Baths
1,974
Sq.Ft.
1967
Year Built
2
Days on Site
O6196142
MLS
$725,000
Neighborhood: Quarters At Winter Park Condo
3
Beds
2F11/2
Baths
2,069
Sq.Ft.
1981
Year Built
2
Days on Site
O6197288
MLS
Open 4/20
2645 Galliano CIRCLE Winter Park,  FL 32792
$320,000
Neighborhood: Vistas At Lake Howell
2
Beds
2F11/2
Baths
1,550
Sq.Ft.
2004
Year Built
2
Days on Site
O6196797
MLS
$635,000
Neighborhood: Orangewood Park
3
Beds
2
Baths
1,376
Sq.Ft.
1954
Year Built
2
Days on Site
O6196291
MLS
$639,900
Neighborhood: Villas Of Aragon Condo
3
Beds
2F11/2
Baths
1,669
Sq.Ft.
1987
Year Built
2
Days on Site
O6196347
MLS
$749,900
Neighborhood: Tax Equities Inc Rep
2
Beds
2
Baths
1,370
Sq.Ft.
1952
Year Built
2
Days on Site
O6196093
MLS
Open 4/20
2710 Euston Rd Winter Park,  FL 32789
$625,000
Neighborhood: Glencoe Sub
4
Beds
3
Baths
1,946
Sq.Ft.
1950
Year Built
2
Days on Site
S5103315
MLS