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Homes Recently Sold in
Winter Park, FL
| Page 6
2,684 Homes
Price
$/Sqft
Bd
Ba
Sqft
Lot
Size
On Movoto
1092 Wading Waters Cir,
Winter Park, FL 32792
$1,088,000
4
Bd
3
Ba
3,057
Sq Ft
SOLD
01/13/26
319 Santiago Dr,
Winter Park, FL 32789
$1,900,000
4
Bd
5
Ba
3,515
Sq Ft
SOLD
01/13/26
1429 Chapman Cir,
Winter Park, FL 32789
$1,280,000
4
Bd
4
Ba
3,116
Sq Ft
SOLD
01/13/26
1840 Shiloh Ln,
Winter Park, FL 32789
$1,025,000
0.28
Acre
SOLD
01/12/26
2432 Barbados Dr,
Winter Park, FL 32792
$249,000
2
Bd
2
Ba
1,020
Sq Ft
SOLD
01/12/26
850 Juanita Rael,
Winter Park, FL 32789
$1,425,000
4
Bd
3
Ba
2,306
Sq Ft
SOLD
01/11/26
1932 Houndslake Dr,
Winter Park, FL 32792
$450,000
3
Bd
2
Ba
1,671
Sq Ft
SOLD
01/11/26
1655 Tremont Ln,
Winter Park, FL 32792
$387,000
3
Bd
2
Ba
1,592
Sq Ft
SOLD
01/10/26
3028 George Mason Ave #7,
Winter Park, FL 32792
$60,000
2
Bd
2
Ba
1,088
Sq Ft
SOLD
01/10/26
1742 Willa Cir,
Winter Park, FL 32792
$460,000
4
Bd
2
Ba
2,313
Sq Ft
SOLD
01/10/26
801 Audubon Ln,
Winter Park, FL 32789
$850,000
2
Bd
2
Ba
1,320
Sq Ft
SOLD
01/08/26
636 Dunblane Dr,
Winter Park, FL 32792
$714,000
3
Bd
2
Ba
1,803
Sq Ft
SOLD
01/08/26
1816 Azalea Ave,
Winter Park, FL 32789
$369,900
3
Bd
2
Ba
1,584
Sq Ft
SOLD
01/08/26
2817 Fitzooth Dr,
Winter Park, FL 32792
$600,000
3
Bd
2
Ba
1,619
Sq Ft
SOLD
01/08/26
1245 Wading Waters Cir,
Winter Park, FL 32792
$1,075,000
4
Bd
3
Ba
3,050
Sq Ft
SOLD
01/08/26
1250 S Denning Dr #213,
Winter Park, FL 32789
$260,000
2
Bd
2
Ba
908
Sq Ft
SOLD
01/08/26
151 N Orlando Ave #204,
Winter Park, FL 32789
$234,000
2
Bd
1
Ba
710
Sq Ft
SOLD
01/08/26
200 Saint Andrews Blvd #1905,
Winter Park, FL 32792
$172,500
2
Bd
2
Ba
987
Sq Ft
SOLD
01/06/26
300 Carolina Ave #201,
Winter Park, FL 32789
$702,050
2
Bd
2
Ba
1,305
Sq Ft
SOLD
01/05/26
265 E Canton Ave #GE,
Winter Park, FL 32789
$586,000
2
Bd
2
Ba
1,057
Sq Ft
SOLD
01/05/26
1701 Palmer Ave,
Winter Park, FL 32789
$1,100,000
4
Bd
3
Ba
2,841
Sq Ft
SOLD
12/30/25
900 Carver St,
Winter Park, FL 32789
$409,000
3
Bd
2
Ba
1,794
Sq Ft
SOLD
12/30/25
3651 N Goldenrod Rd #E102,
Winter Park, FL 32792
$160,000
2
Bd
2
Ba
840
Sq Ft
SOLD
12/30/25
641 Bonita Dr,
Winter Park, FL 32789
$4,800,000
5
Bd
6
Ba
6,699
Sq Ft
SOLD
12/29/25
359 Beloit Ave,
Winter Park, FL 32789
$1,250,000
3
Bd
3
Ba
2,395
Sq Ft
SOLD
12/29/25
5475 Bracken Ct,
Winter Park, FL 32792
$315,000
3
Bd
4
Ba
1,499
Sq Ft
SOLD
12/29/25
1400 S Pennsylvania Ave,
Winter Park, FL 32789
$1,300,000
4
Bd
3
Ba
2,310
Sq Ft
SOLD
12/29/25
824 Garrett Ct,
Winter Park, FL 32792
$440,900
4
Bd
2
Ba
1,738
Sq Ft
SOLD
12/28/25
1566 Lawndale Cir,
Winter Park, FL 32792
$390,000
3
Bd
2
Ba
1,592
Sq Ft
SOLD
12/28/25
1436 Auburn Green Loop,
Winter Park, FL 32792
$363,000
3
Bd
2
Ba
1,415
Sq Ft
SOLD
12/28/25
1611 Walnut Ave,
Winter Park, FL 32789
$1,150,000
4
Bd
3
Ba
2,635
Sq Ft
SOLD
12/27/25
5357 Orange Ave,
Winter Park, FL 32792
$400,000
3
Bd
2
Ba
1,356
Sq Ft
SOLD
12/24/25
623 Saint Johns Ct #623,
Winter Park, FL 32792
$192,000
2
Bd
2
Ba
1,120
Sq Ft
SOLD
12/24/25
4019 Quenita Dr,
Winter Park, FL 32792
$660,000
4
Bd
3
Ba
2,824
Sq Ft
SOLD
12/24/25
224 Lewfield Cir,
Winter Park, FL 32792
$165,000
2
Bd
2
Ba
953
Sq Ft
SOLD
12/24/25
5338 Tangerine Ave,
Winter Park, FL 32792
$425,000
4
Bd
2
Ba
2,195
Sq Ft
SOLD
12/24/25
1812 Stonehurst Rd,
Winter Park, FL 32789
$4,450,000
5
Bd
7
Ba
5,160
Sq Ft
SOLD
12/23/25
5563 Garden Grove Cir,
Winter Park, FL 32792
$385,000
3
Bd
2
Ba
1,436
Sq Ft
SOLD
12/23/25
2412 Middleton Ave,
Winter Park, FL 32792
$500,000
3
Bd
2
Ba
1,340
Sq Ft
SOLD
12/23/25
785 Mcintyre Ave #785,
Winter Park, FL 32789
$625,000
3
Bd
3
Ba
2,015
Sq Ft
SOLD
12/23/25
1405 Auburn Green Loop,
Winter Park, FL 32792
$300,000
2
Bd
2
Ba
1,126
Sq Ft
SOLD
12/23/25
560 Country Club Dr,
Winter Park, FL 32789
$2,600,000
6
Bd
7
Ba
3,946
Sq Ft
SOLD
12/22/25
595 Huntington Ave #4,
Winter Park, FL 32789
$637,500
3
Bd
3
Ba
1,951
Sq Ft
SOLD
12/21/25
2835 Bongart Rd,
Winter Park, FL 32792
$439,900
3
Bd
3
Ba
1,880
Sq Ft
SOLD
12/20/25
615 Warrenton Rd,
Winter Park, FL 32792
$315,000
2
Bd
2
Ba
1,221
Sq Ft
SOLD
12/19/25
3425 Ferndell Dr,
Winter Park, FL 32792
$405,000
3
Bd
2
Ba
1,516
Sq Ft
SOLD
12/19/25
1362 Tierra Cir,
Winter Park, FL 32792
$395,000
4
Bd
3
Ba
2,179
Sq Ft
SOLD
12/18/25
2804 Whispering Way,
Winter Park, FL 32792
$299,000
2
Bd
2
Ba
1,078
Sq Ft
SOLD
12/16/25
4876 Tangerine Ave #4876,
Winter Park, FL 32792
$150,000
1
Bd
1
Ba
763
Sq Ft
SOLD
12/16/25
2218 King Richards Ct,
Winter Park, FL 32792
$425,000
3
Bd
2
Ba
1,562
Sq Ft
SOLD
12/15/25
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