Homes Under $500K in Winter Park, FL
184 listings available — swipe to find your perfect match.
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$150,000126 Scottsdale Sq Unit 126
Winter Park, FL
$250,0007707 Country Pl Unit 4
Winter Park, FL
$295,0002336 Sun Valley Cir Unit BLDG20
Winter Park, FL
$179,9007340 Daniel Webster 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
$115,0001695 Lee Rd Apt E204
Winter Park, FL
$218,000200 Saint Andrews Blvd Apt 3001
Winter Park, FL
$139,000151 Lewfield Cir Unit 4
Winter Park, FL
$430,0001914 Bonanza Ct
Winter Park, FL
$116,0003057 Aaron Burr Ave Unit 1
Winter Park, FL
$219,9007771 Country Pl Unit 7
Winter Park, FL
$298,000151 N Orlando Ave Apt 115
Winter Park, FL
$124,9901695 Lee Rd Apt E211
Winter Park, FL
$315,000311 E Morse Blvd Apt 6-3
Winter Park, FL
$440,0001909 Edwin Blvd
Winter Park, FL
$320,0002401 Antilles Dr
Winter Park, FL
$109,900311 Scottsdale Sq Unit 311
Winter Park, FL
$89,0007309 Daniel Webster Dr Unit 0-2
Winter Park, FL
$317,500121 Stefanik Rd
Winter Park, FL
$465,0003312 Heartwood Ave
Winter Park, FL
$450,0002420 Firstlight Way
Winter Park, FL
$115,0001695 Lee Rd Apt C214
Winter Park, FL
There are currently 184 homes listed under $500,000 in Winter Park, FL. This price range is popular with first-time buyers and investors looking for value in the Winter Park market. HomeSwipr makes it easy to browse every listing — swipe right on the homes you love and our AI learns your taste to surface better matches over time.