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Winter Park Real Estate & Winter Park, FL Homes For Sale | Page 4

440 Homes
 
2345 Brookshire Ave, Winter Park, FL 32792
  • $795,000
  • 3Bd
  • 3Ba
  • 2,488 Sq Ft
$30K
3209 Heartwood Ave, Winter Park, FL 32792
  • $439,900
  • 4Bd
  • 2Ba
  • 1,627 Sq Ft
$10K
1271 Palmer Ave, Winter Park, FL 32789
  • $2,125,000
  • 4Bd
  • 5Ba
  • 2,850 Sq Ft
$70K
504 W Swoope Ave, Winter Park, FL 32789
  • $1,300,000
  • 3Bd
  • 3Ba
  • 2,563 Sq Ft
2119 Howard Dr, Winter Park, FL 32789
  • $3,195,000
  • 5Bd
  • 6Ba
  • 4,139 Sq Ft
618 Blairshire Cir, Winter Park, FL 32792
  • $875,000
  • 4Bd
  • 3Ba
  • 1,876 Sq Ft
Open SUN 3-5
913 Moss Ln, Winter Park, FL 32789
  • $900,000
  • 3Bd
  • 2Ba
  • 1,887 Sq Ft
$50K
1803 Barker Dr, Winter Park, FL 32789
  • $2,190,000
  • 4Bd
  • 3Ba
  • 3,463 Sq Ft
786 W Canton Ave, Winter Park, FL 32789
  • $450,000
  • 0.11 Acre
540 N Pennsylvania Ave, Winter Park, FL 32789
  • $3,950,000
  • 4Bd
  • 2Ba
  • 1,652 Sq Ft
2383 Sun Valley Cir #2383, Winter Park, FL 32792
  • $234,900
  • 2Bd
  • 2Ba
  • 1,295 Sq Ft
1431 Palm Ave, Winter Park, FL 32789
  • $799,999
  • 0.16 Acre
$25K
2410 Sherbrooke Rd, Winter Park, FL 32792
  • $769,000
  • 4Bd
  • 3Ba
  • 2,141 Sq Ft
Open SUN 1-3
311 E Morse Blvd #1-5, Winter Park, FL 32789
  • $2,475,000
  • 3Bd
  • 3Ba
  • 2,316 Sq Ft
7476 Woodburn Ct #38, Winter Park, FL 32792
  • $170,000
  • 2Bd
  • 3Ba
  • 1,031 Sq Ft
822 Symonds Ave, Winter Park, FL 32789
  • $599,999
  • 0.25 Acre
825 Palmer Ave, Winter Park, FL 32789
  • $5,195,900
  • 5Bd
  • 7Ba
  • 5,122 Sq Ft
$200K
1773 Walnut Ave, Winter Park, FL 32789
  • $2,725,000
  • 5Bd
  • 5Ba
  • 3,784 Sq Ft
2260 Coldstream Dr, Winter Park, FL 32792
  • $675,000
  • 4Bd
  • 2Ba
  • 1,509 Sq Ft
$24K
2622 Lake Howell Ln, Winter Park, FL 32792
  • $3,400,000
  • 4Bd
  • 3Ba
  • 3,377 Sq Ft
$350K
698 N New York Ave, Winter Park, FL 32789
  • $5,995,000
  • 5Bd
  • 6Ba
  • 5,096 Sq Ft
$200K
2661 Via Tuscany, Winter Park, FL 32789
  • $5,500,000
  • 4Bd
  • 5Ba
  • 3,880 Sq Ft
$499K
200 S Interlachen Ave #350, Winter Park, FL 32789
  • $2,350,000
  • 3Bd
  • 4Ba
  • 3,110 Sq Ft
1250 S Denning Dr #127, Winter Park, FL 32789
  • $245,000
  • 2Bd
  • 2Ba
  • 908 Sq Ft
2275 Island Run, Winter Park, FL 32792
  • $279,999
  • 3Bd
  • 2Ba
  • 1,467 Sq Ft
$19.9K
508 Brechin Dr, Winter Park, FL 32792
  • $579,000
  • 3Bd
  • 2Ba
  • 1,783 Sq Ft
$20K
500 N Pennsylvania Ave #G, Winter Park, FL 32789
  • $344,500
  • 2Bd
  • 1Ba
  • 709 Sq Ft
$5K
901 Golfview Ter, Winter Park, FL 32789
  • $6,795,000
  • 5Bd
  • 6Ba
  • 5,479 Sq Ft
$200K
1320 Orchid Ave, Winter Park, FL 32789
  • $1,350,000
  • 4Bd
  • 4Ba
  • 2,998 Sq Ft
3020 Nicholson Dr, Winter Park, FL 32792
  • $470,000
  • 4Bd
  • 2Ba
  • 1,756 Sq Ft
$25K
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
  • $699,000
  • 3Bd
  • 2Ba
  • 1,563 Sq Ft
$26K
702 Via Bella, Winter Park, FL 32789
  • $4,090,000
  • 4Bd
  • 6Ba
  • 3,720 Sq Ft
$160K
443 Broadview Ave, Winter Park, FL 32789
  • $999,000
  • 4Bd
  • 3Ba
  • 2,803 Sq Ft
$96K
7530 Cranes Creek Ct, Winter Park, FL 32792
  • $306,900
  • 3Bd
  • 3Ba
  • 1,545 Sq Ft
$1K
2657 Exuma Way, Winter Park, FL 32792
  • $285,000
  • 3Bd
  • 2Ba
  • 1,467 Sq Ft
5108 Lazy Oaks Dr #5108, Winter Park, FL 32792
  • $255,000
  • 2Bd
  • 2Ba
  • 1,008 Sq Ft
$14K
1259 Indiana Ave, Winter Park, FL 32789
  • $575,000
  • 2Bd
  • 3Ba
  • 1,648 Sq Ft
Open SUN 01-4
471 Holt Ave, Winter Park, FL 32789
  • $925,000
  • 4Bd
  • 3Ba
  • 2,528 Sq Ft
Open SUN 12-4
151 N Orlando Ave #242, Winter Park, FL 32789
  • $269,000
  • 2Bd
  • 1Ba
  • 710 Sq Ft
1220 Howell Branch Rd, Winter Park, FL 32789
  • $950,000
  • 3Bd
  • 2Ba
  • 1,487 Sq Ft
$49.5K
1164 Dodd Rd, Winter Park, FL 32792
  • $740,000
  • 5Bd
  • 4Ba
  • 2,840 Sq Ft
$10K
2207 Kindel Ave, Winter Park, FL 32789
  • $1,575,000
  • 3Bd
  • 3Ba
  • 2,733 Sq Ft
Open SUN 2-4
1761 Legion Dr, Winter Park, FL 32789
  • $3,265,000
  • 5Bd
  • 6Ba
  • 4,949 Sq Ft
222 Lewfield Cir, Winter Park, FL 32792
  • $189,900
  • 2Bd
  • 2Ba
  • 953 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
2403 Euston Rd, Winter Park, FL 32789
  • $4,299,000
  • 40 Acre
150 E Reading Way, Winter Park, FL 32789
  • $1,349,000
  • 3Bd
  • 3Ba
  • 2,080 Sq Ft
$50K
151 - 200 of 440 Homes for sale in Winter Park, FL
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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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