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Homes Recently Sold in Winter Park, FL | Page 8

2,744 Homes
 
2500 Lee Rd #122, Winter Park, FL 32789
  • $160,000
  • 1Bd
  • 1Ba
  • 645 Sq Ft
SOLD 05/02/26
2922 Reef Knot Pl, Winter Park, FL 32792
  • $1,100,000
  • 4Bd
  • 4Ba
  • 3,153 Sq Ft
SOLD 05/02/26
1351 Magnolia Ave, Winter Park, FL 32789
  • $3,000,000
  • 5Bd
  • 5Ba
  • 3,460 Sq Ft
SOLD 05/01/26
2237 Woodcrest Dr, Winter Park, FL 32792
  • $490,000
  • 3Bd
  • 2Ba
  • 1,492 Sq Ft
SOLD 05/01/26
3053 George Mason Ave #8A, Winter Park, FL 32792
  • $73,500
  • 1Bd
  • 1Ba
  • 809 Sq Ft
SOLD 05/01/26
7761 Fox Knoll Pl, Winter Park, FL 32792
  • $410,000
  • 3Bd
  • 2Ba
  • 1,485 Sq Ft
SOLD 05/01/26
1010 Garden Dr, Winter Park, FL 32789
  • $450,000
  • 0.26 Acre
SOLD 05/01/26
517 Roughbeard Rd, Winter Park, FL 32792
  • $576,000
  • 3Bd
  • 2Ba
  • 1,873 Sq Ft
SOLD 05/01/26
150 Dana Way, Winter Park, FL 32789
  • $3,675,000
  • 5Bd
  • 5Ba
  • 4,451 Sq Ft
SOLD 05/01/26
1036 Manchester Cir, Winter Park, FL 32792
  • $390,000
  • 3Bd
  • 2Ba
  • 1,574 Sq Ft
SOLD 05/01/26
1117 Kenwood Ave, Winter Park, FL 32789
  • $3,755,000
  • 4Bd
  • 5Ba
  • 4,353 Sq Ft
SOLD 05/01/26
3651 N Goldenrod Rd #D101, Winter Park, FL 32792
  • $179,900
  • 2Bd
  • 2Ba
  • 840 Sq Ft
SOLD 05/01/26
101 S New York Ave #302, Winter Park, FL 32789
  • $1,000,000
  • 3Bd
  • 4Ba
  • 3,174 Sq Ft
SOLD 05/01/26
200 Saint Andrews Blvd #315, Winter Park, FL 32792
  • $165,000
  • 1Bd
  • 1Ba
  • 793 Sq Ft
SOLD 05/01/26
200 Saint Andrews Blvd, Winter Park, FL 32792
  • $165,000
  • 1Bd
  • 1Ba
  • 793 Sq Ft
SOLD 05/01/26
1781 Indiana Ave #A, Winter Park, FL 32789
  • $516,000
  • 3Bd
  • 3Ba
  • 1,616 Sq Ft
SOLD 05/01/26
1832 E Cheryl Dr, Winter Park, FL 32792
  • $445,000
  • 4Bd
  • 2Ba
  • 1,808 Sq Ft
SOLD 04/30/26
7120 Brookside Trl, Winter Park, FL 32792
  • $470,000
  • 4Bd
  • 2Ba
  • 1,753 Sq Ft
SOLD 04/30/26
1780 Mondrian Cir, Winter Park, FL 32789
  • $1,300,000
  • 3Bd
  • 4Ba
  • 2,310 Sq Ft
SOLD 04/30/26
841 W Swoope Ave, Winter Park, FL 32789
  • $450,000
  • 2Bd
  • 1Ba
  • 1,396 Sq Ft
SOLD 04/30/26
7917 Pleasant Pine Cir, Winter Park, FL 32792
  • $581,000
  • 4Bd
  • 3Ba
  • 2,157 Sq Ft
SOLD 04/28/26
720 W Webster Ave, Winter Park, FL 32789
  • $500,000
  • 3Bd
  • 2Ba
  • 1,356 Sq Ft
SOLD 04/28/26
4790 Tangerine Ave #4790, Winter Park, FL 32792
  • $194,995
  • 2Bd
  • 2Ba
  • 1,058 Sq Ft
SOLD 04/28/26
1367 Tierra Cir, Winter Park, FL 32792
  • $424,900
  • 3Bd
  • 2Ba
  • 2,083 Sq Ft
SOLD 04/28/26
629 Country Club Dr, Winter Park, FL 32789
  • $1,655,000
  • 4Bd
  • 4Ba
  • 3,031 Sq Ft
SOLD 04/27/26
4864 Tangerine Ave #4864, Winter Park, FL 32792
  • $200,000
  • 2Bd
  • 2Ba
  • 1,059 Sq Ft
SOLD 04/27/26
5275 Pine Lily Cir, Winter Park, FL 32792
  • $660,000
  • 5Bd
  • 4Ba
  • 3,152 Sq Ft
SOLD 04/27/26
2834 Bright Bird Ln, Winter Park, FL 32792
  • $405,500
  • 3Bd
  • 3Ba
  • 1,907 Sq Ft
SOLD 04/27/26
2503 Versailles Ave, Winter Park, FL 32789
  • $2,100,000
  • 5Bd
  • 4Ba
  • 4,026 Sq Ft
SOLD 04/27/26
1807 Magnolia Ave, Winter Park, FL 32789
  • $1,199,000
  • 5Bd
  • 3Ba
  • 2,618 Sq Ft
SOLD 04/25/26
2530 Leeward Way, Winter Park, FL 32792
  • $265,000
  • 2Bd
  • 2Ba
  • 1,199 Sq Ft
SOLD 04/25/26
1210 Fairway Dr, Winter Park, FL 32792
  • $480,000
  • 3Bd
  • 2Ba
  • 1,737 Sq Ft
SOLD 04/24/26
259 E Canton Ave #259, Winter Park, FL 32789
  • $612,500
  • 2Bd
  • 2Ba
  • 1,040 Sq Ft
SOLD 04/24/26
5473 Bracken Ct, Winter Park, FL 32792
  • $292,175
  • 3Bd
  • 2Ba
  • 1,178 Sq Ft
SOLD 04/24/26
665 Lyman Ave, Winter Park, FL 32789
  • $475,000
  • 3Bd
  • 2Ba
  • 1,119 Sq Ft
SOLD 04/23/26
2020 Cocos Ct, Winter Park, FL 32792
  • $452,000
  • 3Bd
  • 2Ba
  • 1,715 Sq Ft
SOLD 04/23/26
989 Eastbrook Blvd, Winter Park, FL 32792
  • $350,000
  • 3Bd
  • 2Ba
  • 1,140 Sq Ft
SOLD 04/23/26
2713 Eastern Pkwy, Winter Park, FL 32789
  • $625,090
  • 3Bd
  • 2Ba
  • 1,304 Sq Ft
SOLD 04/22/26
2305 Coldstream Dr, Winter Park, FL 32792
  • $1,825,000
  • 5Bd
  • 6Ba
  • 3,655 Sq Ft
SOLD 04/22/26
851 Miles Ave #13, Winter Park, FL 32789
  • $195,000
  • 2Bd
  • 1Ba
  • 808 Sq Ft
SOLD 04/22/26
2500 Lee Rd #229, Winter Park, FL 32789
  • $237,500
  • 2Bd
  • 2Ba
  • 956 Sq Ft
SOLD 04/21/26
2020 Via Tuscany, Winter Park, FL 32789
  • $3,978,550
  • 4Bd
  • 5Ba
  • 4,665 Sq Ft
SOLD 04/20/26
3028 George Mason Ave #J-7E, Winter Park, FL 32792
  • $99,000
  • 2Bd
  • 2Ba
  • 1,088 Sq Ft
SOLD 04/20/26
2681 Fitzhugh Rd, Winter Park, FL 32792
  • $765,000
  • 4Bd
  • 3Ba
  • 2,375 Sq Ft
SOLD 04/20/26
1792 Chilean Ln, Winter Park, FL 32792
  • $310,000
  • 3Bd
  • 1Ba
  • 984 Sq Ft
SOLD 04/20/26
639 Friar Rd, Winter Park, FL 32792
  • $795,000
  • 4Bd
  • 3Ba
  • 1,950 Sq Ft
SOLD 04/19/26
2501 Tahoe Cir, Winter Park, FL 32792
  • $255,000
  • 2Bd
  • 2Ba
  • 1,495 Sq Ft
SOLD 04/19/26
638 Blairshire Cir, Winter Park, FL 32792
  • $650,000
  • 3Bd
  • 2Ba
  • 1,701 Sq Ft
SOLD 04/18/26
300 Carolina Ave #207, Winter Park, FL 32789
  • $400,000
  • 1Bd
  • 2Ba
  • 1,149 Sq Ft
SOLD 04/18/26
521 Fairfax Ave, Winter Park, FL 32789
  • $775,000
  • 4Bd
  • 2Ba
  • 2,112 Sq Ft
SOLD 04/18/26
351 - 400 of 2,744 Homes in Winter Park, FL
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Winter Park, FL real estate market trends

Statistics as of September 2026
$556K
Avg. list price
$332/Sqft
Avg. price/sqft
439
Homes for sale
1,770 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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