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Winter Park Real Estate & Winter Park, FL Homes For Sale | Page 5

483 Homes
 
2703 Tierra Cir, Winter Park, FL 32792
  • $464,000
  • 3Bd
  • 2Ba
  • 1,737 Sq Ft
Open THU 4-6
2033 Canny Cv, Winter Park, FL 32792
  • $389,000
  • 3Bd
  • 3Ba
  • 1,907 Sq Ft
$10K
901 Harmon Ave, Winter Park, FL 32789
  • $650,000
  • 2Bd
  • 2Ba
  • 1,277 Sq Ft
281 Brewer Ave, Winter Park, FL 32789
  • $1,800,000
  • 5Bd
  • 5Ba
  • 4,029 Sq Ft
1927 S Lakemont Ave, Winter Park, FL 32792
  • $915,000
  • 3Bd
  • 4Ba
  • 2,093 Sq Ft
Open SAT 12-3
2568 Lotafun Ave, Winter Park, FL 32789
  • $395,000
  • 3Bd
  • 2Ba
  • 1,201 Sq Ft
$10K
230 Killarney Dr, Winter Park, FL 32789
  • $1,250,000
  • 4Bd
  • 1Ba
  • 1,260 Sq Ft
240 Killarney Dr, Winter Park, FL 32789
  • $1,275,000
  • 3Bd
  • 3Ba
  • 1,329 Sq Ft
1562 Arbor Park Dr, Winter Park, FL 32789
  • $775,000
  • 4Bd
  • 3Ba
  • 1,899 Sq Ft
2526 Passamonte Dr #10F, Winter Park, FL 32792
  • $335,000
  • 3Bd
  • 3Ba
  • 1,790 Sq Ft
7450 Wynnewood Sq #189, Winter Park, FL 32792
  • $170,000
  • 2Bd
  • 3Ba
  • 1,031 Sq Ft
$15K
1500 Gay Rd #4D, Winter Park, FL 32789
  • $164,500
  • 1Bd
  • 1Ba
  • 732 Sq Ft
$5.4K
2487 Harbour Way, Winter Park, FL 32792
  • $270,000
  • 3Bd
  • 3Ba
  • 1,803 Sq Ft
$20K
1401 Aster Ct, Winter Park, FL 32792
  • $414,900
  • 4Bd
  • 2Ba
  • 1,653 Sq Ft
$15K
250 Killarney, Winter Park, FL 32789
  • $1,600,000
  • 4Bd
  • 4Ba
  • 2,568 Sq Ft
922 N Pennsylvania Ave, Winter Park, FL 32789
  • $1,875,000
  • 4Bd
  • 4Ba
  • 3,440 Sq Ft
$120K
1418 Lone Feather Trl, Winter Park, FL 32792
  • $699,500
  • 4Bd
  • 3Ba
  • 2,197 Sq Ft
$25.5K
462 W Lyman Ave, Winter Park, FL 32789
  • $1,495,000
  • 3Bd
  • 3Ba
  • 1,944 Sq Ft
$100K
885 Carnation Dr, Winter Park, FL 32792
  • $368,000
  • 4Bd
  • 2Ba
  • 1,240 Sq Ft
$7K
724 Monmouth Way, Winter Park, FL 32792
  • $798,000
  • 5Bd
  • 4Ba
  • 2,832 Sq Ft
$50.9K
1415 Grove Ter, Winter Park, FL 32789
  • $2,200,000
  • 0.54 Acre
777 Halifax Ave, Winter Park, FL 32792
  • $1,449,000
  • 5Bd
  • 5Ba
  • 3,109 Sq Ft
$51K
2450 Grand Teton Cir #2450, Winter Park, FL 32792
  • $250,000
  • 3Bd
  • 2Ba
  • 1,311 Sq Ft
$5K
2189 Sussex Rd, Winter Park, FL 32792
  • $375,000
  • 4Bd
  • 3Ba
  • 1,776 Sq Ft
1823 Sunset Dr, Winter Park, FL 32789
  • $2,549,000
  • 5Bd
  • 5Ba
  • 3,479 Sq Ft
5184 Lazy Oaks Dr, Winter Park, FL 32792
  • $275,000
  • 2Bd
  • 2Ba
  • 1,008 Sq Ft
$5K
2305 Sun Valley Cir Winter Park #FL 32792, Winter Park, FL 32792
  • $279,900
  • 2Bd
  • 2Ba
  • 1,295 Sq Ft
2372 Sun Valley Cir #2372, Winter Park, FL 32792
  • $285,000
  • 2Bd
  • 2Ba
  • 1,495 Sq Ft
341 E Reading Way, Winter Park, FL 32789
  • $1,525,000
  • 4Bd
  • 4Ba
  • 3,723 Sq Ft
$40K
1000 S Semoran Blvd #408, Winter Park, FL 32792
  • $138,000
  • 1Bd
  • 1Ba
  • 776 Sq Ft
$10K
1000 S Semoran Blvd #404, Winter Park, FL 32792
  • $138,000
  • 1Bd
  • 1Ba
  • 776 Sq Ft
$10K
1000 S Semoran Blvd #306, Winter Park, FL 32792
  • $138,000
  • 1Bd
  • 1Ba
  • 796 Sq Ft
$10K
2041 Jewell Ave, Winter Park, FL 32789
  • $439,900
  • 3Bd
  • 1Ba
  • 1,508 Sq Ft
$30.1K
2228 Azalea Pl, Winter Park, FL 32789
  • $5,600,000
  • 5Bd
  • 6Ba
  • 5,152 Sq Ft
981 Aragon Ave, Winter Park, FL 32789
  • $494,999
  • 2Bd
  • 1Ba
  • 857 Sq Ft
$4K
1138 S Pennsylvania Ave, Winter Park, FL 32789
  • $925,000
  • 3Bd
  • 3Ba
  • 2,434 Sq Ft
$74K
3006 Northwood Blvd, Winter Park, FL 32789
  • $950,000
  • 4Bd
  • 3Ba
  • 2,075 Sq Ft
Open SAT 1-3
1003 Lake Bell Dr, Winter Park, FL 32789
  • $549,900
  • 3Bd
  • 2Ba
  • 1,837 Sq Ft
$30K
259 Orange Terrace Dr, Winter Park, FL 32789
  • $449,900
  • 3Bd
  • 2Ba
  • 1,248 Sq Ft
$10K
660 W Morse Blvd, Winter Park, FL 32789
  • $2,800,000
  • 3Bd
  • 4Ba
  • 3,286 Sq Ft
7488 Whisperwood Dr #28, Winter Park, FL 32792
  • $199,000
  • 2Bd
  • 3Ba
  • 1,578 Sq Ft
$11K
1564 Lawndale Cir, Winter Park, FL 32792
  • $450,000
  • 4Bd
  • 3Ba
  • 1,980 Sq Ft
2712 Tortoise Cv, Winter Park, FL 32792
  • $235,000
  • 2Bd
  • 1Ba
  • 924 Sq Ft
Jessica Court, Winter Park, FL 32789
  • $449,000
  • 0.14 Acre
1591 Cardinal Ct, Winter Park, FL 32789
  • $2,995,000
  • 5Bd
  • 3Ba
  • 3,523 Sq Ft
2914 Reef Knot Pl, Winter Park, FL 32792
  • $1,725,000
  • 6Bd
  • 6Ba
  • 4,173 Sq Ft
2015 Summerfield Rd, Winter Park, FL 32792
  • $1,262,500
  • 4Bd
  • 4Ba
  • 3,024 Sq Ft
Open SAT 12-3
1500 Gay Rd #3C, Winter Park, FL 32789
  • $235,000
  • 2Bd
  • 2Ba
  • 1,026 Sq Ft
$3K
512 W Swoope Ave, Winter Park, FL 32789
  • $1,399,000
  • 3Bd
  • 3Ba
  • 2,585 Sq Ft
101 S New York Ave #311, Winter Park, FL 32789
  • $1,775,000
  • 3Bd
  • 4Ba
  • 3,112 Sq Ft
$74.9K
201 - 250 of 483 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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