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Winter Park Real Estate & Winter Park, FL Homes For Sale | Page 3

484 Homes
 
1320 Orchid Ave, Winter Park, FL 32789
  • $1,350,000
  • 4Bd
  • 4Ba
  • 2,998 Sq Ft
3020 Nicholson Dr, Winter Park, FL 32792
  • $495,000
  • 4Bd
  • 2Ba
  • 1,756 Sq Ft
Photos coming soon
  • $739,777
  • 4Bd
  • 2Ba
  • 2,267 Sq Ft
7506 Cranes Creek Ct #30, Winter Park, FL 32792
  • $365,000
  • 3Bd
  • 3Ba
  • 1,861 Sq Ft
1850 Bryan Ave, Winter Park, FL 32789
  • $725,000
  • 3Bd
  • 2Ba
  • 1,563 Sq Ft
Open SUN 2-4
1021 N Pennsylvania Ave, Winter Park, FL 32789
  • $1,295,000
  • 0.51 Acre
3651 N Goldenrod Rd #C205, Winter Park, FL 32792
  • $159,900
  • 2Bd
  • 2Ba
  • 840 Sq Ft
$10K
2211 King Richards Ct, Winter Park, FL 32792
  • $529,000
  • 4Bd
  • 2Ba
  • 1,845 Sq Ft
$10K
702 Via Bella, Winter Park, FL 32789
  • $4,400,000
  • 4Bd
  • 6Ba
  • 3,720 Sq Ft
443 Broadview Ave, Winter Park, FL 32789
  • $1,095,000
  • 4Bd
  • 3Ba
  • 2,803 Sq Ft
7530 Cranes Creek Ct, Winter Park, FL 32792
  • $309,900
  • 3Bd
  • 3Ba
  • 1,545 Sq Ft
160 W Rockwood Way, Winter Park, FL 32789
  • $3,395,000
  • 5Bd
  • 6Ba
  • 4,015 Sq Ft
5108 Lazy Oaks Dr #5108, Winter Park, FL 32792
  • $269,000
  • 2Bd
  • 2Ba
  • 1,008 Sq Ft
1259 Indiana Ave, Winter Park, FL 32789
  • $575,000
  • 2Bd
  • 3Ba
  • 1,648 Sq Ft
Open SAT 1-4
1445 Via Sangro Pl, Winter Park, FL 32792
  • $1,350,000
  • 6Bd
  • 6Ba
  • 5,021 Sq Ft
471 Holt Ave, Winter Park, FL 32789
  • $975,000
  • 4Bd
  • 3Ba
  • 2,528 Sq Ft
$20.9K
151 N Orlando Ave #242, Winter Park, FL 32789
  • $269,000
  • 2Bd
  • 1Ba
  • 710 Sq Ft
1220 Howell Branch Rd, Winter Park, FL 32789
  • $999,500
  • 3Bd
  • 2Ba
  • 1,487 Sq Ft
$50.5K
2430 Chantilly Ave, Winter Park, FL 32789
  • $1,598,000
  • 4Bd
  • 4Ba
  • 2,916 Sq Ft
3302 Royal St, Winter Park, FL 32792
  • $269,900
  • 3Bd
  • 2Ba
  • 1,197 Sq Ft
$5K
1164 Dodd Rd, Winter Park, FL 32792
  • $775,000
  • 5Bd
  • 4Ba
  • 2,840 Sq Ft
$20K
2207 Kindel Ave, Winter Park, FL 32789
  • $1,600,000
  • 3Bd
  • 3Ba
  • 2,733 Sq Ft
1761 Legion Dr, Winter Park, FL 32789
  • $3,265,000
  • 5Bd
  • 6Ba
  • 4,949 Sq Ft
751 Pansy Ave, Winter Park, FL 32789
  • $1,950,000
  • 3Bd
  • 4Ba
  • 2,703 Sq Ft
1486 Hyde Park Dr, Winter Park, FL 32792
  • $429,900
  • 3Bd
  • 2Ba
  • 1,518 Sq Ft
222 Lewfield Cir, Winter Park, FL 32792
  • $189,900
  • 2Bd
  • 2Ba
  • 953 Sq Ft
1550 Palm Ave, Winter Park, FL 32789
  • $1,829,000
  • 4Bd
  • 4Ba
  • 2,706 Sq Ft
276 Detmar Dr, Winter Park, FL 32789
  • $3,600,000
  • 4Bd
  • 5Ba
  • 4,202 Sq Ft
2181 Linden Rd, Winter Park, FL 32792
  • $419,990
  • 5Bd
  • 3Ba
  • 1,442 Sq Ft
$30K
1016 Aragon Ave, Winter Park, FL 32789
  • $660,000
  • 4Bd
  • 4Ba
  • 1,840 Sq Ft
2403 Euston Rd, Winter Park, FL 32789
  • $4,299,000
  • 40 Acre
150 E Reading Way, Winter Park, FL 32789
  • $1,449,000
  • 3Bd
  • 3Ba
  • 2,080 Sq Ft
$46K
2824 Prince John Rd, Winter Park, FL 32792
  • $475,000
  • 2Bd
  • 2Ba
  • 1,438 Sq Ft
1416 Border Dr, Winter Park, FL 32789
  • $620,000
  • 0.16 Acre
$40K
7605 Aloma Pines Ct, Winter Park, FL 32792
  • $359,000
  • 3Bd
  • 3Ba
  • 1,872 Sq Ft
900 Carver St, Winter Park, FL 32789
  • $664,000
  • 3Bd
  • 3Ba
  • 1,794 Sq Ft
$25K
1526 Miller Ave, Winter Park, FL 32789
  • $1,574,900
  • 5Bd
  • 5Ba
  • 3,252 Sq Ft
Open THU 1-4
285 Lewfield Cir #285, Winter Park, FL 32792
  • $147,000
  • 1Bd
  • 1Ba
  • 678 Sq Ft
7525 Lodge Pole Trl, Winter Park, FL 32792
  • $575,000
  • 4Bd
  • 2Ba
  • 1,936 Sq Ft
Open SUN 11-2
623 Grenadine Ct #623, Winter Park, FL 32792
  • $194,900
  • 2Bd
  • 2Ba
  • 1,037 Sq Ft
$5K
2112 Eastbrook Blvd, Winter Park, FL 32792
  • $423,000
  • 3Bd
  • 2Ba
  • 1,470 Sq Ft
$6.99K
1621 Chestnut Ave, Winter Park, FL 32789
  • $899,000
  • 3Bd
  • 3Ba
  • 2,022 Sq Ft
943 Fairway Dr, Winter Park, FL 32792
  • $650,000
  • 4Bd
  • 3Ba
  • 2,067 Sq Ft
$39.9K
720 Pansy Ave, Winter Park, FL 32789
  • $1,295,000
  • 3Bd
  • 4Ba
  • 2,191 Sq Ft
$55K
3019 Antique Oaks Cir #127, Winter Park, FL 32792
  • $143,500
  • 1Bd
  • 1Ba
  • 749 Sq Ft
$1K
1133 Bella Lago Cv, Winter Park, FL 32792
  • $1,999,900
  • 6.64 Acre
$100K
1660 Gladiolas Dr, Winter Park, FL 32792
  • $495,000
  • 3Bd
  • 2Ba
  • 2,047 Sq Ft
$14.9K
2857 Clever Ln, Winter Park, FL 32792
  • $399,995
  • 3Bd
  • 3Ba
  • 1,782 Sq Ft
$9.9K
1278 S Pennsylvania Ave #13, Winter Park, FL 32789
  • $799,000
  • 3Bd
  • 3Ba
  • 1,957 Sq Ft
1842 Puritan Ave, Winter Park, FL 32792
  • $419,000
  • 4Bd
  • 2Ba
  • 1,836 Sq Ft
101 - 150 of 484 Homes for sale in Winter Park, FL
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Winter Park, FL real estate market trends

Statistics as of October 2026
$599K
Avg. list price
$346/Sqft
Avg. price/sqft
445
Homes for sale
1,786 Sqft
Avg. home size
67 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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