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Winter Park, FL Homes for Sale & Luxury Real Estate
Welcome to Winter Park, Florida—Central Florida’s premier destination for historic charm, cultural depth, and prestigious estate living. Renowned for the brick-lined pathways of Park Avenue, the legacy of Rollins College, and the stunning Winter Park Chain of Lakes (including Lake Virginia and Lake Osceola), this community remains a crown jewel among the top luxury communities in Orlando. Explore all active single-family homes and luxury properties across ZIP codes 32789 and 32792 mapped below. For a sophisticated, metrics-driven approach to acquiring or divesting a high-end asset in this competitive market, connect with real estate strategist Yousef Zeidan of RE/MAX Prime Properties today.
- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
- List
- Mixed
- Map
98 Properties Available
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
$2,195,000
942 ENCLAVE PL, Winter Park, FL 32792
Listed by Matthew Burks CORCORAN PREMIER REALTY
$2,175,000
946 ENCLAVE PL, Winter Park, FL 32792
Listed by Matthew Burks CORCORAN PREMIER REALTY
$2,125,000
950 ENCLAVE PL, Winter Park, FL 32792
Listed by Laura Earl CORCORAN PREMIER REALTY
$2,235,000
926 ENCLAVE PL, Winter Park, FL 32792
Listed by Laura Earl CORCORAN PREMIER REALTY
$2,099,000
938 ENCLAVE PL, Winter Park, FL 32792
Listed by Laura Earl CORCORAN PREMIER REALTY
$1,899,000
910 ENCLAVE PL, Winter Park, FL 32792
Listed by Laura Earl CORCORAN PREMIER REALTY
$2,050,000
930 ENCLAVE PL, Winter Park, FL 32792
Listed by Matthew Burks CORCORAN PREMIER REALTY
$2,200,000
1130 PARK NORTH PLACE, Winter Park, FL 32789
Listed by Jennifer King CORCORAN PREMIER REALTY
$1,895,000
914 ENCLAVE PL, Winter Park, FL 32792
Listed by Matthew Burks CORCORAN PREMIER REALTY
$639,000
1908 CYRIL CT, Winter Park, FL 32792
Listed by Marina Dyachkova COLDWELL BANKER REALTY
$2,569,999
1754 TAYLOR AVE, Winter Park, FL 32789
Listed by Christopher Christensen ONE LUXURY INTERNATIONAL LLC
$4,900,000
1180 VIA LUGANO, Winter Park, FL 32789
Listed by Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
$2,549,000
1823 SUNSET DR, Winter Park, FL 32789
Listed by Christopher Christensen ONE LUXURY INTERNATIONAL LLC
$849,000
439 N CAPEN AVE, Winter Park, FL 32789
Listed by Brian Rotenberger COMPASS FLORIDA LLC
$770,000
730 W SWOOPE AVE, Winter Park, FL 32789
Listed by Carolina Mejia AROD PARTNERS REALTY
$1,249,000
3006 NORTHWOOD BLVD, Winter Park, FL 32789
Listed by Daren Ellington ORLANDO HOMES GROUP LLC
$614,990
4353 STEED TER, Winter Park, FL 32792
Listed by Barbara Robinson DALTON WADE INC
$719,900
2344 WOODCREST DR, Winter Park, FL 32792
Listed by Shannon Lee EXPLORE FLORIDA REALTY SERVICES LLC
$1,725,000
2914 REEF KNOT PL, Winter Park, FL 32792
Listed by Lianna Dangelo SOTERA LIVING
$3,995,000
1600 LEGION DR, Winter Park, FL 32789
Listed by Brian Teach COLDWELL BANKER REALTY
$5,500,000
313 SYLVAN DR, Winter Park, FL 32789
Listed by Mick Night PREMIER SOTHEBY'S INTL. REALTY
$725,000
1316 BLUE STEM LN, Winter Park, FL 32792
Listed by Matthew Fong AFFINITY REALTY LLC
$3,500,000
1836 WHITEHALL DR, Winter Park, FL 32789
Listed by Bianca Khoury PREMIER SOTHEBY'S INTL. REALTY
$4,950,000
231 CHELTON CIR, Winter Park, FL 32789
Listed by Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
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