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Winter Park Real Estate & Winter Park, FL Homes For Sale | Page 2

484 Homes
 
2215 Woodcrest Dr, Winter Park, FL 32792
  • $675,000
  • 4Bd
  • 2Ba
  • 1,688 Sq Ft
Open THU 04-6
167 Jergo Rd, Winter Park, FL 32792
  • $530,000
  • 4Bd
  • 4Ba
  • 925 Sq Ft
1386 Clematis Ln, Winter Park, FL 32792
  • $427,000
  • 4Bd
  • 3Ba
  • 1,714 Sq Ft
2345 Brookshire Ave, Winter Park, FL 32792
  • $850,000
  • 3Bd
  • 3Ba
  • 2,488 Sq Ft
3209 Heartwood Ave, Winter Park, FL 32792
  • $449,900
  • 4Bd
  • 2Ba
  • 1,627 Sq Ft
7302 Swallow Run #7302, Winter Park, FL 32792
  • $134,900
  • 2Bd
  • 2Ba
  • 756 Sq Ft
2417 Chantilly Ave, Winter Park, FL 32789
  • $1,579,000
  • 4Bd
  • 4Ba
  • 2,718 Sq Ft
1271 Palmer Ave, Winter Park, FL 32789
  • $2,195,000
  • 4Bd
  • 5Ba
  • 2,850 Sq Ft
Open SUN 12-2
504 W Swoope Ave, Winter Park, FL 32789
  • $1,300,000
  • 3Bd
  • 3Ba
  • 2,563 Sq Ft
7560 Aloma Pines Ct, Winter Park, FL 32792
  • $365,000
  • 3Bd
  • 3Ba
  • 1,866 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
  • $895,000
  • 4Bd
  • 3Ba
  • 1,876 Sq Ft
Open SUN 11-2
447 N Phelps Ave, Winter Park, FL 32789
  • $960,000
  • 2Bd
  • 1Ba
  • 1,290 Sq Ft
2301 Conifer Ave, Winter Park, FL 32792
  • $440,000
  • 4Bd
  • 2Ba
  • 2,189 Sq Ft
$10K
913 Moss Ln, Winter Park, FL 32789
  • $950,000
  • 3Bd
  • 2Ba
  • 1,887 Sq Ft
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
4870 Seminole Ave, Winter Park, FL 32792
  • $380,000
  • 3Bd
  • 2Ba
  • 1,277 Sq Ft
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
  • $825,000
  • 0.16 Acre
2410 Sherbrooke Rd, Winter Park, FL 32792
  • $789,000
  • 4Bd
  • 3Ba
  • 2,141 Sq Ft
Open SAT 1-4
311 E Morse Blvd #1-5, Winter Park, FL 32789
  • $2,475,000
  • 3Bd
  • 3Ba
  • 2,316 Sq Ft
250 W Reading Way, Winter Park, FL 32789
  • $4,325,000
  • 5Bd
  • 5Ba
  • 4,853 Sq Ft
7476 Woodburn Ct #38, Winter Park, FL 32792
  • $170,000
  • 2Bd
  • 3Ba
  • 1,031 Sq Ft
1256 S Pennsylvania Ave #9, Winter Park, FL 32789
  • $950,000
  • 3Bd
  • 3Ba
  • 1,957 Sq Ft
$15K
2302 Barbados Dr, Winter Park, FL 32792
  • $295,000
  • 2Bd
  • 2Ba
  • 1,544 Sq Ft
822 Symonds Ave, Winter Park, FL 32789
  • $599,999
  • 0.25 Acre
2260 Mulbry Dr, Winter Park, FL 32789
  • $1,925,000
  • 5Bd
  • 4Ba
  • 3,246 Sq Ft
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
1257 Wading Waters Cir, Winter Park, FL 32792
  • $1,600,000
  • 6Bd
  • 5Ba
  • 5,239 Sq Ft
2260 Coldstream Dr, Winter Park, FL 32792
  • $699,000
  • 4Bd
  • 2Ba
  • 1,509 Sq Ft
2622 Lake Howell Ln, Winter Park, FL 32792
  • $3,750,000
  • 4Bd
  • 3Ba
  • 3,377 Sq Ft
2136 Linden Rd, Winter Park, FL 32792
  • $365,000
  • 3Bd
  • 2Ba
  • 1,185 Sq Ft
698 N New York Ave, Winter Park, FL 32789
  • $6,195,000
  • 5Bd
  • 6Ba
  • 5,096 Sq Ft
$5K
2661 Via Tuscany, Winter Park, FL 32789
  • $5,999,990
  • 4Bd
  • 5Ba
  • 3,880 Sq Ft
3651 N Goldenrod Rd #C109, Winter Park, FL 32792
  • $165,000
  • 2Bd
  • 2Ba
  • 840 Sq Ft
200 S Interlachen Ave #350, Winter Park, FL 32789
  • $2,350,000
  • 3Bd
  • 4Ba
  • 3,110 Sq Ft
274 N Ranger Blvd, Winter Park, FL 32792
  • $659,900
  • 3Bd
  • 2Ba
  • 1,420 Sq Ft
Open SAT 11-3
1250 S Denning Dr #127, Winter Park, FL 32789
  • $245,000
  • 2Bd
  • 2Ba
  • 908 Sq Ft
2626 Ambergate Rd, Winter Park, FL 32792
  • $380,000
  • 3Bd
  • 1Ba
  • 1,143 Sq Ft
2275 Island Run, Winter Park, FL 32792
  • $299,990
  • 3Bd
  • 2Ba
  • 1,467 Sq Ft
508 Brechin Dr, Winter Park, FL 32792
  • $629,000
  • 3Bd
  • 2Ba
  • 1,783 Sq Ft
$10K
1922 Hammerlin Ave, Winter Park, FL 32789
  • $1,095,000
  • 3Bd
  • 3Ba
  • 1,873 Sq Ft
$205K
2349 Shadowland Loop, Winter Park, FL 32792
  • $425,000
  • 3Bd
  • 3Ba
  • 1,755 Sq Ft
7839 University Garden Dr, Winter Park, FL 32792
  • $1,000,000
  • 3.8 Acre
2122 Ridge Dr, Winter Park, FL 32792
  • $360,000
  • 4Bd
  • 3Ba
  • 1,664 Sq Ft
2500 Lee Rd #143, Winter Park, FL 32789
  • $130,000
  • 1Bd
  • 1Ba
  • 645 Sq Ft
901 Golfview Ter, Winter Park, FL 32789
  • $6,995,000
  • 5Bd
  • 6Ba
  • 5,479 Sq Ft
51 - 100 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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