Homes Recently Sold in Winter Park, FL

price
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1-40 of 284 Homes
Sold, last 90 days
front view of a brick house with a small yard
Sold 12/9/25

$205,000

2
Bedrooms
1,219
Square Feet

200 St Andrews Boulevard, Unit 1707, Winter Park, FL 32792

$1,500,000 | 1460 Via Sangro Place, Winter Park, FL 32792
Sold 12/23/25Virtual Tour

$1,500,000

7
Bedrooms
5,111
Square Feet
0.52
Acres

1460 Via Sangro Place, Winter Park, FL 32792

a row of palm trees in front of house
Closed 10/15/25Virtual Tour

$1,206,400

4
Bedrooms
3,321
Square Feet
0.72
Acres

4048 Gilder Rose Place, Winter Park, FL 32792

$399,000 | 4959 Ardmore Drive, Winter Park, FL 32792
Closed 9/30/25

$399,000

3
Bedrooms
1,664
Square Feet
0.39
Acres

4959 Ardmore Drive, Winter Park, FL 32792

a front view of a house with a yard and garage
Sold 12/10/25

$1,063,303

4
Bedrooms
2,662
Square Feet
0.15
Acres

1835 Karolina Avenue, Winter Park, FL 32789

$956,809 | 20 Karolina Avenue, Winter Park, FL 32789
Sold 12/18/25

$956,809

4
Bedrooms
2,662
Square Feet
0.15
Acres

20 Karolina Avenue, Winter Park, FL 32789

a front view of a house with a yard
Closed 10/16/25

$358,000

3
Bedrooms
1,114
Square Feet
0.08
Acres

1827 Blaine Terrace, Winter Park, FL 32792

a view of a yard with a palm tree
Sold 12/5/25Virtual Tour

$6,111,000

5
Bedrooms
5,022
Square Feet
0.69
Acres

1860 Summerland Avenue, Winter Park, FL 32789

a front view of a house with garden
Sold 12/19/25

$1,042,500

4
Bedrooms
2,388
Square Feet
0.15
Acres

1341 Lyndale Boulevard, Winter Park, FL 32789

a front view of a house with a yard and a garage
Sold 12/11/25

$2,078,500

5
Bedrooms
4,328
Square Feet
0.25
Acres

715 Vía Bella, Winter Park, FL 32789

a front view of a house with a yard
Sold 10/24/25

$1,800,000

4
Bedrooms
2,950
Square Feet
0.18
Acres

1682 Arbor Park Drive, Winter Park, FL 32789

$1,250,000 | 359 Beloit Avenue, Winter Park, FL 32789
Sold 12/29/25

$1,250,000

3
Bedrooms
2,395
Square Feet
0.23
Acres

359 Beloit Avenue, Winter Park, FL 32789

$4,450,000 | 1812 Stonehurst Road, Winter Park, FL 32789
Sold 12/23/25

$4,450,000

5
Bedrooms
5,160
Square Feet
0.46
Acres

1812 Stonehurst Road, Winter Park, FL 32789

a view of a house with a yard and potted plants
Sold 11/13/25

$85,000

2
Bedrooms
1,085
Square Feet

110 Scottsdale Square, Unit 110, Winter Park, FL 32792

$325,000 | 260 Killarney Bay Court, Unit 6, Winter Park, FL 32789
Closed 10/3/25

$325,000

2
Bedrooms
1,140
Square Feet

260 Killarney Bay Court, Unit 6, Winter Park, FL 32789

a house view with a backyard space
Sold 12/10/25

$495,000

3
Bedrooms
1,370
Square Feet
0.21
Acres

625 South Lakemont Avenue, Winter Park, FL 32792

a view of outdoor space with trees
Sold 12/11/25

$1,300,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.35
Acres

751 Williams Drive, Winter Park, FL 32789

a view of a house with a yard
Sold 11/26/25

$810,000

2
Bedrooms
1,738
Square Feet
0.15
Acres

1314 Canterbury Road, Winter Park, FL 32789

a front view of a house with a yard
Sold 12/12/25

$470,000

3
Bedrooms
1,125
Square Feet
0.22
Acres

502 Dunblane Drive, Winter Park, FL 32792

$320,000 | 5117 Cypress Court, Winter Park, FL 32792
Sold 12/23/25

$320,000

3
Bedrooms
1,534
Square Feet
0.23
Acres

5117 Cypress Court, Winter Park, FL 32792

a view of a house with a yard
Sold 12/22/25

$418,000

3
Bedrooms
1,050
Square Feet
0.19
Acres

1030 North Lakemont Avenue, Winter Park, FL 32792

a view of a house with a yard and potted plants
Sold 10/29/25

$110,000

3
Bedrooms
1,250
Square Feet

106 Scottsdale Square, Unit 106, Winter Park, FL 32792

a view of swimming pool with patio
Sold 9/30/25

$72,000

1
Bedrooms
785
Square Feet

339 Scottsdale Square, Unit 339, Winter Park, FL 32792

a view of backyard of house with green space
Sold 12/11/25

$1,000,500

3
Bedrooms
1,431
Square Feet
0.28
Acres

210 East Rockwood Way, Winter Park, FL 32789

a view of a house with a yard
Sold 11/14/25

$879,000

3
Bedrooms
2,227
Square Feet
0.10
Acres

451 Fairfax Avenue, Winter Park, FL 32789

a view of a car parked in front of a house
Closed 10/16/25

$455,500

3
Bedrooms
2,015
Square Feet
0.26
Acres

1317 Medinah Court, Winter Park, FL 32792

$405,000 | 1872 Biscayne Drive, Winter Park, FL 32789
Sold 12/22/25

$405,000

2
Bedrooms
969
Square Feet
0.15
Acres

1872 Biscayne Drive, Winter Park, FL 32789

$450,000 | 639 Friar Road, Winter Park, FL 32792
Sold 12/29/25

$450,000

4
Bedrooms
1,829
Square Feet
0.21
Acres

639 Friar Road, Winter Park, FL 32792

a front view of a house with a yard
Sold 12/9/25

$567,500

3
Bedrooms
1,453
Square Feet
0.16
Acres

1010 Aragon Avenue, Winter Park, FL 32789

a backyard of a house with table and chairs
Sold 11/25/25

$505,000

4
Bedrooms
2,002
Square Feet
0.37
Acres

1691 Bomi Circle, Winter Park, FL 32792

a front view of a house with a yard
Sold 11/20/25

$360,000

3
Bedrooms
1,145
Square Feet
0.13
Acres

611 Ololu Drive, Winter Park, FL 32789

a front view of a house with a yard
Sold 11/19/25

$750,000

3
Bedrooms
2,422
Square Feet
0.23
Acres

1681 Woodland Avenue, Winter Park, FL 32789

a front view of a house with a yard
Sold 10/30/25

$5,700,000

5
Bedrooms
4,735
Square Feet
1.94
Acres

374 Henkel Circle, Winter Park, FL 32789

front view of a house with a patio yard and a large tree
Sold 11/10/25

$1,430,000

3
Bedrooms
2,230
Square Feet
0.31
Acres

1011 McKean Circle, Winter Park, FL 32789

a front view of a house with a garden
Sold 11/25/25Virtual Tour

$528,000

4
Bedrooms
2,124
Square Feet
0.21
Acres

4991 Tangerine Avenue, Winter Park, FL 32792

$470,000 | 2381 Roxbury Road, Winter Park, FL 32789
Sold 12/23/25Virtual Tour

$470,000

3
Bedrooms
1,785
Square Feet
0.28
Acres

2381 Roxbury Road, Winter Park, FL 32789

a front view of a house with garden
Sold 12/12/25

$359,900

3
Bedrooms
1,283
Square Feet
0.16
Acres

780 Baffie Avenue, Winter Park, FL 32789

a front view of a house with a yard table and chairs
Sold 11/19/25

$699,450

4
Bedrooms
1,829
Square Feet
0.25
Acres

1346 Golfside Drive, Winter Park, FL 32792

$165,000 | 1000 South Semoran Boulevard, Unit 814, Winter Park, FL 32792
Sold 12/15/25

$165,000

2
Bedrooms
1,049
Square Feet

1000 South Semoran Boulevard, Unit 814, Winter Park, FL 32792

a view of front door of house
Sold 12/8/25

$119,000

2
Bedrooms
1,049
Square Feet

1000 South Semoran Boulevard, Unit 608, Winter Park, FL 32792

 
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