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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.
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- $ 100,000
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- $ 600,000
- $ 1,000,000
- List
- Mixed
- Map
126 Properties Available
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
$2,299,000
1840 LAUREL RD, Winter Park, FL 32789
Listed by Matt Tomaszewski CORCORAN PREMIER REALTY
$1,749,000
2525 LAFAYETTE AVE, Winter Park, FL 32789
Listed by Matt Tomaszewski CORCORAN PREMIER REALTY
$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
$1,895,000
914 ENCLAVE PL, Winter Park, FL 32792
Listed by Matthew Burks CORCORAN PREMIER REALTY
$1,350,000
1117 WADING WATERS CIR, Winter Park, FL 32792
Listed by Brian Hyser THE AGENCY FL
$1,829,000
1550 PALM AVE, Winter Park, FL 32789
Listed by Brian Mitnik RE/MAX 200 REALTY
$3,600,000
276 DETMAR DR, Winter Park, FL 32789
Listed by Melanie Johnston CALL IT CLOSED INTL REALTY
$1,875,000
1661 LAUREL RD, Winter Park, FL 32789
Listed by Caroline Van Den Berg VAN DEN BERG REAL ESTATE GROUP
$689,000
900 CARVER ST, Winter Park, FL 32789
Listed by Farhad Haniff EXP REALTY LLC
$1,574,900
1526 MILLER AVE, Winter Park, FL 32789
Listed by Kim Griffin RE/MAX EXCLUSIVE COLLECTION
$899,000
1621 CHESTNUT AVE, Winter Park, FL 32789
Listed by Kelly Price KELLY PRICE & COMPANY LLC
$664,900
2333 WESTMINSTER CT, Winter Park, FL 32789
Listed by Steven Luppert COMPASS FLORIDA LLC
$600,000
7525 LODGE POLE TRL, Winter Park, FL 32792
Listed by Amy Turner KELLER WILLIAMS WINTER PARK
$689,900
943 FAIRWAY DR, Winter Park, FL 32792
Listed by Amy Turner KELLER WILLIAMS WINTER PARK
$860,000
120 LONGBRANCH RD, Winter Park, FL 32792
Listed by Karen Albright OPENDOOR BROKERAGE LLC
$750,000
1287 VERDANT GLADE PL, Winter Park, FL 32792
Listed by Renee Funk EXP REALTY LLC
$649,000
1409 SUNSET DR, Winter Park, FL 32789
Listed by TJ Tuzzeo KONA REALTY SERVICES LLC
$625,000
1871 BRYAN AVE, Winter Park, FL 32789
Listed by Nick McKee KELLER WILLIAMS WINTER PARK
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