Homes Recently Sold in Winter Park, FL

price
-
1-41 of 325 Homes
Sold, last 90 days
front view of a house with a yard
Sold 5/11/26

$530,000

3
Bedrooms
1,275
Square Feet
0.22
Acres

1921 Kimbrace Place, Winter Park, FL 32792

SVGUnlock more homes you won't find anywhere else
Listings are only private online. All buyers & agents can access in our offices or by contacting Compass.
a front view of a house with a yard and potted plants
1/55
Sold 6/30/26

$735,000

3
Bedrooms
1,739
Square Feet
0.22
Acres

738 South Pennsylvania Avenue, Winter Park, FL 32789

a view of a house with a yard and sitting area
Sold 5/22/26

$775,000

4
Bedrooms
2,112
Square Feet
0.17
Acres

521 Fairfax Avenue, Winter Park, FL 32789

$2,570,000 | 135 West Swoope Avenue, Winter Park, FL 32789
Sold 5/12/26

$2,570,000

3
Bedrooms
2,667
Square Feet
0.08
Acres

135 West Swoope Avenue, Winter Park, FL 32789

$610,000 | 1860 Staunton Avenue, Winter Park, FL 32789
Sold 4/13/26

$610,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.31
Acres

1860 Staunton Avenue, Winter Park, FL 32789

$2,100,000 | 2503 Versailles Avenue, Winter Park, FL 32789
1/53
Sold 6/11/26

$2,100,000

5
Bedrooms
4,026
Square Feet
0.35
Acres

2503 Versailles Avenue, Winter Park, FL 32789

a front view of house with yard and green space
Sold 5/15/26Virtual Tour

$3,000,000

5
Bedrooms
4,296
Square Feet
0.31
Acres

473 Fletcher Place, Winter Park, FL 32789

front view of house with a yard
Sold 5/7/26Virtual Tour

$776,533

3
Bedrooms
1,566
Square Feet
0.21
Acres

781 Northwood Circle, Winter Park, FL 32789

$287,500 | 4428 Steed Terrace, Winter Park, FL 32792
Sold 6/29/26

$287,500

3
Bedrooms
1,800
Square Feet
0.31
Acres

4428 Steed Terrace, Winter Park, FL 32792

a front view of house with yard and green space
Sold 5/14/26

$700,000

5
Bedrooms
2,765
Square Feet
0.37
Acres

1106 Golfside Drive, Winter Park, FL 32792

a front view of a house with a garden
Sold 4/10/26

$560,000

4
Bedrooms
2,035
Square Feet
0.16
Acres

1517 Harmon Avenue, Winter Park, FL 32789

a front view of a house with garden
Sold 4/15/26

$1,850,000

4
Bedrooms
3,670
Square Feet
0.34
Acres

1713 Elizabeths Walk, Winter Park, FL 32789

a front view of a house with garden
Sold 5/29/26

$4,500,000

4
Bedrooms
3,922
Square Feet
0.36
Acres

1521 Harris Circle, Winter Park, FL 32789

front view of house with a yard and plants
1/48
Sold 6/24/26

$5,125,000

5
Bedrooms
5,164
Square Feet
0.34
Acres

1221 Richmond Road, Winter Park, FL 32789

$845,000 | 2208 Howard Drive, Winter Park, FL 32789
Sold 6/12/26

$845,000

3
Bedrooms
2,155
Square Feet
0.27
Acres

2208 Howard Drive, Winter Park, FL 32789

$390,000 | 7517 Laurel Springs Drive, Winter Park, FL 32792
1/53
Sold 6/11/26

$390,000

3
Bedrooms
1,678
Square Feet
0.19
Acres

7517 Laurel Springs Drive, Winter Park, FL 32792

$519,000 | 1944 Natalen Road, Winter Park, FL 32792
1/27
Sold 6/30/26

$519,000

3
Bedrooms
1,380
Square Feet
0.22
Acres

1944 Natalen Road, Winter Park, FL 32792

$385,000 | 610 Ellendale Drive, Winter Park, FL 32792
1/29
Sold 6/30/26

$385,000

4
Bedrooms
1,359
Square Feet
0.19
Acres

610 Ellendale Drive, Winter Park, FL 32792

$2,280,000 | 436 North Knowles Avenue, Winter Park, FL 32789
Sold 6/8/26

$2,280,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.26
Acres

436 North Knowles Avenue, Winter Park, FL 32789

$1,549,900 | 1516 Miller Avenue, Winter Park, FL 32789
1/8
Sold 6/30/26

$1,549,900

4
Bedrooms
3,144
Square Feet
0.16
Acres

1516 Miller Avenue, Winter Park, FL 32789

a front view of a house with a yard
Sold 5/21/26

$73,500

1
Bedrooms
809
Square Feet

3053 George Mason Avenue, Unit 8A, Winter Park, FL 32792

a house with a outdoor space
1/2
Sold 6/29/26

$550,000

3
Bedrooms
1,280
Square Feet
0.08
Acres

650 Douglas Avenue, Winter Park, FL 32789

$299,000 | 2529 Windward Way, Winter Park, FL 32792
1/20
Sold 6/17/26

$299,000

3
Bedrooms
1,105
Square Feet
0.09
Acres

2529 Windward Way, Winter Park, FL 32792

a front view of a house with yard outdoor seating and barbeque oven
Sold 4/17/26

$649,000

4
Bedrooms
1,936
Square Feet
0.24
Acres

1523 Golfside Drive, Winter Park, FL 32792

$399,000 | 2808 Bright Bird Lane, Winter Park, FL 32792
1/35
Sold 6/30/26

$399,000

3
Bedrooms
1,907
Square Feet
0.04
Acres

2808 Bright Bird Lane, Winter Park, FL 32792

a front view of a house with a yard and garage
Sold 5/18/26Virtual Tour

$410,000

3
Bedrooms
1,485
Square Feet
0.12
Acres

7761 Fox Knoll Place, Winter Park, FL 32792

$499,000 | 1871 Bryan Avenue, Winter Park, FL 32789
1/3
Sold 6/24/26

$499,000

3
Bedrooms
1,232
Square Feet
0.15
Acres

1871 Bryan Avenue, Winter Park, FL 32789

$786,000 | 2940 De Brocy Way, Winter Park, FL 32792
1/55
Sold 6/9/26Virtual Tour

$786,000

3
Bedrooms
2,679
Square Feet
0.26
Acres

2940 De Brocy Way, Winter Park, FL 32792

a front view of a house with garden
1/10
Sold 6/4/26

$406,000

4
Bedrooms
1,048
Square Feet
0.16
Acres

1812 Killarney Drive, Winter Park, FL 32789

$377,500 | 3505 Corrine Drive, Orlando, FL 32803
1/22
Sold 5/21/26

$377,500

2
Bedrooms
987
Square Feet
0.20
Acres

3505 Corrine Drive, Orlando, FL 32803

front view of a house with a yard
Sold 4/16/26

$630,000

4
Bedrooms
1,943
Square Feet
0.22
Acres

649 Berwick Drive, Winter Park, FL 32792

front view of a house
Sold 4/30/26

$310,000

2
Bedrooms
1,320
Square Feet
0.10
Acres

736 Warrenton Road, Winter Park, FL 32792

$375,000 | 819 Densmore Drive, Winter Park, FL 32792
1/39
Sold 6/12/26

$375,000

3
Bedrooms
1,300
Square Feet
0.23
Acres

819 Densmore Drive, Winter Park, FL 32792

$887,500 | 627 Dunblane Drive, Winter Park, FL 32792
1/36
Sold 6/11/26Virtual Tour

$887,500

4
Bedrooms
2,086
Square Feet
0.21
Acres

627 Dunblane Drive, Winter Park, FL 32792

$420,000 | 1611 Little Wren Lane, Winter Park, FL 32792
1/29
Sold 6/11/26Virtual Tour

$420,000

3
Bedrooms
1,755
Square Feet
0.06
Acres

1611 Little Wren Lane, Winter Park, FL 32792

$470,000 | 3167 Ash Park Loop, Winter Park, FL 32792
1/62
Sold 6/5/26

$470,000

4
Bedrooms
1,906
Square Feet
0.22
Acres

3167 Ash Park Loop, Winter Park, FL 32792

a front view of a house with a yard and garage
Sold 5/21/26

$480,000

3
Bedrooms
1,737
Square Feet
0.23
Acres

1210 Fairway Drive, Winter Park, FL 32792

$379,000 | 1433 Aster Court, Winter Park, FL 32792
1/30
Sold 6/25/26

$379,000

3
Bedrooms
1,363
Square Feet
0.22
Acres

1433 Aster Court, Winter Park, FL 32792

front view of a house with a yard
1/20
Closed 5/1/26

$215,000

2
Bedrooms
1,085
Square Feet
Unavailable
Acres

200 St Andrews, Unit 3001, Winter Park, FL 32792

a front view of a house with yard and green space
Sold 5/15/26

$7,164,000

5
Bedrooms
5,006
Square Feet
0.56
Acres

1821 Pinetree Road, Winter Park, FL 32789

front view of a house with a yard
Sold 4/29/26Virtual Tour

$421,000

3
Bedrooms
1,400
Square Feet
0.23
Acres

633 Lander Road, Winter Park, FL 32792

For Sale:

Discover Your Perfect Home

Explore Nearby Homes

Looking for Rentals?

Homes and Apartments for Rent in Winter Park