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Winter Park Real Estate & Winter Park, FL Homes For Sale | Page 9

440 Homes
 
160 W Rockwood Way, Winter Park, FL 32789
  • $3,395,000
  • 5Bd
  • 6Ba
  • 4,015 Sq Ft
2430 Chantilly Ave, Winter Park, FL 32789
  • $1,550,000
  • 4Bd
  • 4Ba
  • 2,916 Sq Ft
2126 Albert Lee Pkwy, Winter Park, FL 32789
  • $415,000
  • 3Bd
  • 2Ba
  • 1,187 Sq Ft
751 Pansy Ave, Winter Park, FL 32789
  • $1,875,000
  • 3Bd
  • 4Ba
  • 2,703 Sq Ft
1486 Hyde Park Dr, Winter Park, FL 32792
  • $429,900
  • 3Bd
  • 2Ba
  • 1,518 Sq Ft
1016 Aragon Ave, Winter Park, FL 32789
  • $650,000
  • 4Bd
  • 4Ba
  • 1,840 Sq Ft
2824 Prince John Rd, Winter Park, FL 32792
  • $475,000
  • 2Bd
  • 2Ba
  • 1,438 Sq Ft
285 Lewfield Cir #285, Winter Park, FL 32792
  • $147,000
  • 1Bd
  • 1Ba
  • 678 Sq Ft
7525 Lodge Pole Trl, Winter Park, FL 32792
  • $550,000
  • 4Bd
  • 2Ba
  • 1,936 Sq Ft
943 Fairway Dr, Winter Park, FL 32792
  • $650,000
  • 4Bd
  • 3Ba
  • 2,067 Sq Ft
565 Huntington Ave #565, Winter Park, FL 32789
  • $635,000
  • 3Bd
  • 3Ba
  • 2,015 Sq Ft
1256 Melissa Ct, Winter Park, FL 32789
  • $660,000
  • 3Bd
  • 3Ba
  • 1,690 Sq Ft
250 Carolina Ave #205, Winter Park, FL 32789
  • $739,000
  • 2Bd
  • 2Ba
  • 1,311 Sq Ft
2286 Marsh Sedge Ln, Winter Park, FL 32792
  • $770,000
  • 4Bd
  • 3Ba
  • 2,192 Sq Ft
609 S Phelps Ave, Winter Park, FL 32789
  • $2,800,000
  • 5Bd
  • 5Ba
  • 4,018 Sq Ft
7384 Grand Ave, Winter Park, FL 32792
  • $385,000
  • 3Bd
  • 2Ba
  • 1,162 Sq Ft
1652 Berkshire Ave, Winter Park, FL 32789
  • $429,000
  • 3Bd
  • 2Ba
  • 1,498 Sq Ft
1915 Carrigan Ave, Winter Park, FL 32792
  • $299,900
  • 3Bd
  • 1Ba
  • 1,520 Sq Ft
2370 Barbados Dr, Winter Park, FL 32792
  • $305,000
  • 3Bd
  • 2Ba
  • 1,467 Sq Ft
1840 Bryan Ave, Winter Park, FL 32789
  • $1,725,000
  • 4Bd
  • 4Ba
  • 3,727 Sq Ft
1525 Granville Dr, Winter Park, FL 32789
  • $4,595,000
  • 5Bd
  • 6Ba
  • 5,211 Sq Ft
1909 Taylor Ave, Winter Park, FL 32792
  • $425,000
  • 0.19 Acre
1562 Arbor Park Dr, Winter Park, FL 32789
  • $775,000
  • 4Bd
  • 3Ba
  • 1,899 Sq Ft
885 Carnation Dr, Winter Park, FL 32792
  • $368,000
  • 4Bd
  • 2Ba
  • 1,240 Sq Ft
724 Monmouth Way, Winter Park, FL 32792
  • $759,675
  • 5Bd
  • 4Ba
  • 2,832 Sq Ft
2189 Sussex Rd, Winter Park, FL 32792
  • $375,000
  • 4Bd
  • 3Ba
  • 1,776 Sq Ft
1754 Taylor Ave, Winter Park, FL 32789
  • $2,569,999
  • 5Bd
  • 5Ba
  • 3,670 Sq Ft
722 S Ranger Blvd, Winter Park, FL 32792
  • $775,000
  • 4Bd
  • 3Ba
  • 2,164 Sq Ft
2501 Lafayette Ave, Winter Park, FL 32789
  • $1,795,000
  • 4Bd
  • 4Ba
  • 2,819 Sq Ft
1420 Magnolia Ave, Winter Park, FL 32789
  • $1,690,000
  • 4Bd
  • 4Ba
  • 3,174 Sq Ft
723 Symonds Ave, Winter Park, FL 32789
  • $1,600,000
  • 4Bd
  • 4Ba
  • 3,065 Sq Ft
1821 Killarney Dr, Winter Park, FL 32789
  • $599,999
  • 0.38 Acre
525 Ololu Dr, Winter Park, FL 32789
  • $490,900
  • 3Bd
  • 3Ba
  • 1,786 Sq Ft
1741 Westchester Ave, Winter Park, FL 32789
  • $524,900
  • 3Bd
  • 2Ba
  • 1,434 Sq Ft
5143 Lazy Oaks Dr #5143, Winter Park, FL 32792
  • $275,000
  • 2Bd
  • 2Ba
  • 1,008 Sq Ft
102 Bell Pl, Winter Park, FL 32792
  • $1,299,000
  • 4Bd
  • 4Ba
  • 2,459 Sq Ft
950 Hanover Ave, Winter Park, FL 32789
  • $439,000
  • 3Bd
  • 2Ba
  • 1,606 Sq Ft
541 W Canton Ave, Winter Park, FL 32789
  • $2,495,000
  • 4Bd
  • 4Ba
  • 3,553 Sq Ft
2412 Chantilly Ave, Winter Park, FL 32789
  • $2,394,500
  • 5Bd
  • 7Ba
  • 4,506 Sq Ft
1885 Temple Dr, Winter Park, FL 32789
  • $2,195,000
  • 5Bd
  • 4Ba
  • 3,691 Sq Ft
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Winter Park, FL real estate market trends

Statistics as of November 2026
$575K
Avg. list price
$333/Sqft
Avg. price/sqft
430
Homes for sale
1,836 Sqft
Avg. home size
70 Days
Avg. days on market
Movoto makes it easy to track market trends in Winter Park, FL. Whether you’re entering the market or planning your next move, understanding these key metrics can guide smart decisions. Looking for more detailed housing market stats in Winter Park, FL?
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