Homes for Sale in Winter Park, FL
24 listings available right now — swipe to find your perfect match.
Start Swiping in Winter Park24
Active Listings
$729,358
Avg. Price
$115,000
Starting From
$3,100,000
Up To
Featured Listings in Winter Park
$1,375,0002015 Summerfield Rd
Winter Park, FL
$2,249,9001205 Mayfield Ave
Winter Park, FL
$650,0001489 Aster Ct
Winter Park, FL
$150,000126 Scottsdale Sq Unit 126
Winter Park, FL
$250,0007707 Country Pl Unit 4
Winter Park, FL
$3,100,000457 E New England Ave
Winter Park, FL
$295,0002336 Sun Valley Cir Unit BLDG20
Winter Park, FL
$179,9007340 Daniel Webster Dr
Winter Park, FL
$899,000731 Midget Dr
Winter Park, FL
$450,000640 N Park Ave Apt 5
Winter Park, FL
$209,999851 Miles Ave Apt 13
Winter Park, FL
$444,9001951 Canny Cv
Winter Park, FL
$630,0002612 Roxbury Rd
Winter Park, FL
$849,0001780 Bryan Ave
Winter Park, FL
$115,0001695 Lee Rd Apt E204
Winter Park, FL
$218,000200 Saint Andrews Blvd Apt 3001
Winter Park, FL
$2,184,0002503 Versailles Ave
Winter Park, FL
$139,000151 Lewfield Cir Unit 4
Winter Park, FL
$430,0001914 Bonanza Ct
Winter Park, FL
$925,000560 Ololu Dr
Winter Park, FL
$750,000676 Dunblane Dr
Winter Park, FL
$675,0001127 Wildmeadow Run
Winter Park, FL
$116,0003057 Aaron Burr Ave Unit 1
Winter Park, FL
$219,9007771 Country Pl Unit 7
Winter Park, FL
Find Your Dream Home in Winter Park
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Start Swiping in Winter ParkAbout Homes in Winter Park, FL
Winter Park is one of the most sought-after real estate markets in the Orlando area of Florida. Whether you are a first-time buyer looking for a starter home or an experienced investor seeking luxury property, Winter Park has something for everyone. The local market features a diverse mix of architectural styles, from contemporary builds to classic designs, set among the distinctive neighborhoods that make Winter Park special. HomeSwipr makes it easy to explore every listing — simply swipe right on the homes you love and left on the ones that are not quite right. Our AI learns your taste with every swipe and surfaces better matches over time, so you spend less time scrolling and more time scheduling tours.