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

440 Homes
 
1500 Harris Cir, Winter Park, FL 32789
  • $1,175,000
  • 3Bd
  • 3Ba
  • 2,096 Sq Ft
2038 Ponderosa Ave, Winter Park, FL 32792
  • $399,500
  • 3Bd
  • 2Ba
  • 1,360 Sq Ft
$15.5K
2718 Eastern Pkwy, Winter Park, FL 32789
  • $2,450,000
  • 4Bd
  • 5Ba
  • 3,308 Sq Ft
Open SUN 1-4
1825 Chilean Ln, Winter Park, FL 32792
  • $450,000
  • 5Bd
  • 3Ba
  • 1,636 Sq Ft
3027 Aaron Bur Ave #L1, Winter Park, FL 32792
  • $169,999
  • 2Bd
  • 3Ba
  • 1,090 Sq Ft
470 W Comstock Ave, Winter Park, FL 32789
  • $5,480,000
  • 6Bd
  • 7Ba
  • 6,134 Sq Ft
345 Beloit Ave, Winter Park, FL 32789
  • $1,625,000
  • 3Bd
  • 3Ba
  • 2,884 Sq Ft
Open SUN 03-5
2352 Sun Valley Cir, Winter Park, FL 32792
  • $280,000
  • 2Bd
  • 2Ba
  • 1,495 Sq Ft
1830 Gladiolas Dr, Winter Park, FL 32792
  • $375,000
  • 3Bd
  • 2Ba
  • 1,674 Sq Ft
1386 Clematis Ln, Winter Park, FL 32792
  • $417,000
  • 4Bd
  • 3Ba
  • 1,714 Sq Ft
7463 Canford Ct #15, Winter Park, FL 32792
  • $270,000
  • 3Bd
  • 3Ba
  • 1,580 Sq Ft
1940 Magnolia Ave, Winter Park, FL 32792
  • $1,190,000
  • 4Bd
  • 4Ba
  • 5,519 Sq Ft
1200 Via Salerno, Winter Park, FL 32789
  • $5,995,000
  • 5Bd
  • 6Ba
  • 5,476 Sq Ft
603 Carnation Dr, Winter Park, FL 32792
  • $399,900
  • 4Bd
  • 2Ba
  • 1,427 Sq Ft
$20K
506 Lander Rd, Winter Park, FL 32792
  • $450,000
  • 3Bd
  • 2Ba
  • 1,346 Sq Ft
2330 Westminster Ct, Winter Park, FL 32789
  • $985,000
  • 5Bd
  • 3Ba
  • 3,296 Sq Ft
1030 Bonita Dr, Winter Park, FL 32789
  • $1,100,000
  • 0.18 Acre
808 Densmore Dr, Winter Park, FL 32792
  • $509,999
  • 3Bd
  • 2Ba
  • 1,460 Sq Ft
1884 Jessica Ct, Winter Park, FL 32789
  • $699,900
  • 3Bd
  • 2Ba
  • 1,666 Sq Ft
1631 Hillcrest Ave, Winter Park, FL 32789
  • $4,500,000
  • 5Bd
  • 6Ba
  • 4,754 Sq Ft
4832 Tangerine Ave #4832, Winter Park, FL 32792
  • $188,800
  • 2Bd
  • 2Ba
  • 1,058 Sq Ft
1825 Whitehall Dr, Winter Park, FL 32789
  • $3,195,000
  • 4Bd
  • 6Ba
  • 4,311 Sq Ft
Open SUN 12-4
4786 Tangerine Ave #4786, Winter Park, FL 32792
  • $220,000
  • 2Bd
  • 2Ba
  • 1,281 Sq Ft
7641 Village Green Dr, Winter Park, FL 32792
  • $515,000
  • 3Bd
  • 3Ba
  • 1,602 Sq Ft
$14K
2887 Temple Trl, Winter Park, FL 32789
  • $695,000
  • 2Bd
  • 3Ba
  • 1,801 Sq Ft
5468 Bracken Ct, Winter Park, FL 32792
  • $299,000
  • 3Bd
  • 3Ba
  • 1,602 Sq Ft
$10K
220 Killarney Bay Ct #6-2, Winter Park, FL 32789
  • $335,000
  • 2Bd
  • 2Ba
  • 1,140 Sq Ft
$4K
1600 Legion Dr, Winter Park, FL 32789
  • $3,495,000
  • 5Bd
  • 6Ba
  • 4,483 Sq Ft
2913 Clever Ln, Winter Park, FL 32792
  • $425,000
  • 3Bd
  • 3Ba
  • 1,907 Sq Ft
1681 Woodland Ave, Winter Park, FL 32789
  • $2,629,000
  • 5Bd
  • 5Ba
  • 3,682 Sq Ft
1939 Woodcrest Dr, Winter Park, FL 32792
  • $1,349,000
  • 4Bd
  • 4Ba
  • 2,575 Sq Ft
Open SUN 11-1
1445 Via Sangro Pl, Winter Park, FL 32792
  • $1,249,000
  • 6Bd
  • 6Ba
  • 5,021 Sq Ft
8061 Pleasant Pine Cir, Winter Park, FL 32792
  • $750,000
  • 5Bd
  • 4Ba
  • 3,496 Sq Ft
1011 Mckean Cir, Winter Park, FL 32789
  • $6,000,000
  • 5Bd
  • 7Ba
  • 4,806 Sq Ft
1355 Hibiscus Ave, Winter Park, FL 32789
  • $2,100,000
  • 5Bd
  • 6Ba
  • 4,155 Sq Ft
216 Lewfield Cir #216, Winter Park, FL 32792
  • $230,000
  • 3Bd
  • 2Ba
  • 1,268 Sq Ft
2219 Winter Woods Blvd, Winter Park, FL 32792
  • $479,999
  • 3Bd
  • 3Ba
  • 1,776 Sq Ft
1611 Chestnut Ave, Winter Park, FL 32789
  • $985,000
  • 4Bd
  • 4Ba
  • 2,916 Sq Ft
Open SUN 2-4
1411 Devon Rd, Winter Park, FL 32789
  • $950,000
  • 2Bd
  • 2Ba
  • 1,947 Sq Ft
1407 Broad Wing Ln, Winter Park, FL 32792
  • $482,000
  • 3Bd
  • 3Ba
  • 2,308 Sq Ft
$9K
1737 Indiana Ave, Winter Park, FL 32789
  • $1,399,900
  • 4Bd
  • 4Ba
  • 2,984 Sq Ft
Open SUN 12-4
731 Bongart Rd, Winter Park, FL 32792
  • $519,900
  • 4Bd
  • 3Ba
  • 1,842 Sq Ft
2036 Via Tuscany, Winter Park, FL 32789
  • $2,100,000
  • 0.36 Acre
3479 Seagrape, Winter Park, FL 32792
  • $350,000
  • 3Bd
  • 1Ba
  • 1,115 Sq Ft
4882 Tangerine Ave #4882, Winter Park, FL 32792
  • $185,000
  • 2Bd
  • 2Ba
  • 1,281 Sq Ft
700 Melrose Ave #M23, Winter Park, FL 32789
  • $289,000
  • 2Bd
  • 2Ba
  • 1,074 Sq Ft
Open SUN 1-4
1500 Gay Rd #26-C, Winter Park, FL 32789
  • $255,000
  • 2Bd
  • 2Ba
  • 1,026 Sq Ft
2228 King Charles Ct, Winter Park, FL 32792
  • $575,000
  • 4Bd
  • 3Ba
  • 2,551 Sq Ft
2067 Poinciana Rd, Winter Park, FL 32792
  • $548,000
  • 4Bd
  • 2Ba
  • 2,352 Sq Ft
$12K
3307 Amber Wood Way #106, Winter Park, FL 32792
  • $169,000
  • 2Bd
  • 3Ba
  • 1,031 Sq Ft
51 - 100 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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