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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
118 Properties Available
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
$1,699,900
2613 LAFAYETTE AVE, Winter Park, FL 32789
Listed by Matt Tomaszewski CORCORAN PREMIER REALTY
$2,125,000
918 ENCLAVE PL, Winter Park, FL 32792
Listed by Laura Earl CORCORAN PREMIER REALTY
$3,195,000
2119 HOWARD DR, Winter Park, FL 32789
Listed by Laura Earl CORCORAN PREMIER REALTY
$5,195,900
825 PALMER AVE, Winter Park, FL 32789
Listed by Laura Earl CORCORAN PREMIER REALTY
$725,000
1850 BRYAN AVE, Winter Park, FL 32789
Listed by Jennifer King CORCORAN PREMIER REALTY
$2,299,000
1840 LAUREL RD, Winter Park, FL 32789
Listed by Matt Tomaszewski CORCORAN PREMIER REALTY
$2,300,000
938 ENCLAVE PL, Winter Park, FL 32792
Listed by Laura Earl CORCORAN PREMIER REALTY
$2,275,000
930 ENCLAVE PL, Winter Park, FL 32792
Listed by Matthew Burks CORCORAN PREMIER REALTY
$2,070,000
914 ENCLAVE PL, Winter Park, FL 32792
Listed by Matthew Burks CORCORAN PREMIER REALTY
$1,399,900
1737 INDIANA AVE, Winter Park, FL 32789
Listed by Tori Nguyen LOKATION
$649,000
518 GILBERT RD, Winter Park, FL 32792
Listed by Monika Kenney PALMANO GROUP RE BROKERAGE LLC
$900,000
2052 WOOD THRUSH LN, Winter Park, FL 32792
Listed by Ron Verzaro, II KELLER WILLIAMS ADVANTAGE REALTY
$1,995,000
2007 EDWIN BLVD, Winter Park, FL 32792
Listed by Angela Rodriguez DREAM FINDERS REALTY GROUP CORP
$1,950,000
513 DUNRAVEN DR, Winter Park, FL 32792
Listed by Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
$724,900
266 N RANGER BLVD, Winter Park, FL 32792
Listed by Moises Rivera ELITE PROPERTY REAL ESTATE LLC
$769,900
1003 GOLFSIDE DR, Winter Park, FL 32792
Listed by Lina Paeres QP HOMES REALTY LLC
$6,195,000
698 N NEW YORK AVE, Winter Park, FL 32789
Listed by Mick Night PREMIER SOTHEBY'S INTL. REALTY
$780,000
739 ROUGHBEARD RD, Winter Park, FL 32792
Listed by John Harbuck SERHANT
$1,890,000
2614 PARKLAND DR, Winter Park, FL 32789
Listed by Ryan Gaston JW GASTON LLC
$2,990,000
532 LANGHOLM DR, Winter Park, FL 32789
Listed by Christopher Christensen ONE LUXURY INTERNATIONAL LLC
$1,250,000
120 BROADVIEW AVE, Winter Park, FL 32789
Listed by Catherine D'Amico FANNIE HILLMAN & ASSOCIATES
$659,000
5303 PINE LILY CIR, Winter Park, FL 32792
Listed by Jonathan Casique PM ELITE REALTY LLC
$3,695,999
1742 TEMPLE DR, Winter Park, FL 32789
Listed by Mark Anthony Buot ROI AVE LLC
$3,495,000
662 GRANVILLE DRIVE, Winter Park, FL 32789
Listed by Nathalie Bates PREMIER SOTHEBY'S INTL. REALTY
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