5 Bedroom Homes for Sale in Winter Park, FL

price
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1-41 of 49 Homes
5+ beds
$5,600,000 | 2228 Azalea Place, Winter Park, FL 32789
1/67
Listed By Compass

$5,600,000

5
Bedrooms
5,152
Square Feet
0.33
Acres

2228 Azalea Place, Winter Park, FL 32789

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a front view of a house with a yard and garage
1/8
Listed By Compass

$1,360,000

5
Bedrooms
3,735
Square Feet
0.19
Acres

420 Ohio Street, Winter Park, FL 32789

a view of backyard with a tub
1/37
Listed By Compass

$1,185,999

6
Bedrooms
4
Bathrooms
2,282
Square Feet
0.09
Acres

726 North Pennsylvania Avenue, Winter Park, FL 32789

$2,225,000 | 1885 Temple Drive, Winter Park, FL 32789
1/54
Listed By CompassVirtual Tour

$2,225,000

5
Bedrooms
3,691
Square Feet
0.24
Acres

1885 Temple Drive, Winter Park, FL 32789

$3,995,000 | 1600 Legion Drive, Winter Park, FL 32789
1/70
Listed By Coldwell Banker Realty

$3,995,000

5
Bedrooms
4,483
Square Feet
0.32
Acres

1600 Legion Drive, Winter Park, FL 32789

$2,499,000 | 426 Worthington Drive, Winter Park, FL 32789
1/46

$2,499,000

5
Bedrooms
3,520
Square Feet
0.23
Acres

426 Worthington Drive, Winter Park, FL 32789

$1,725,000 | 2914 Reef Knot Place, Winter Park, FL 32792
1/56

$1,725,000

6
Bedrooms
4,173
Square Feet
0.67
Acres

2914 Reef Knot Place, Winter Park, FL 32792

$3,500,000 | 1836 Whitehall Drive, Winter Park, FL 32789
1/70

$3,500,000

5
Bedrooms
4,168
Square Feet
0.25
Acres

1836 Whitehall Drive, Winter Park, FL 32789

$3,490,000 | 121 East Fawsett Road, Winter Park, FL 32789
1/11

$3,490,000

5
Bedrooms
4,191
Square Feet
0.28
Acres

121 East Fawsett Road, Winter Park, FL 32789

$1,988,888 | 2032 Kimbrace Place, Winter Park, FL 32792
1/78

$1,988,888

5
Bedrooms
3,382
Square Feet
0.25
Acres

2032 Kimbrace Place, Winter Park, FL 32792

$2,250,000 | 240 North Phelps Avenue, Winter Park, FL 32789
1/41

$2,250,000

5
Bedrooms
2,889
Square Feet
0.21
Acres

240 North Phelps Avenue, Winter Park, FL 32789

$1,429,000 | 1473 Berkshire Avenue, Winter Park, FL 32789
1/38

$1,429,000

5
Bedrooms
2,351
Square Feet
0.15
Acres

1473 Berkshire Avenue, Winter Park, FL 32789

$1,149,900 | 1448 Lake Florence Way, Winter Park, FL 32792
1/51
Virtual Tour

$1,149,900

5
Bedrooms
3,652
Square Feet
0.15
Acres

1448 Lake Florence Way, Winter Park, FL 32792

$2,125,000 | 950 Enclave Place, Winter Park, FL 32792
1/3

$2,125,000

5
Bedrooms
3,797
Square Feet
0.23
Acres

950 Enclave Place, Winter Park, FL 32792

$2,175,000 | 946 Enclave Place, Winter Park, FL 32792
1/3

$2,175,000

5
Bedrooms
3,989
Square Feet
0.19
Acres

946 Enclave Place, Winter Park, FL 32792

$2,195,000 | 942 Enclave Place, Winter Park, FL 32792
1/3

$2,195,000

5
Bedrooms
3,831
Square Feet
0.18
Acres

942 Enclave Place, Winter Park, FL 32792

a front view of a house with garden
1/44

$2,995,000

5
Bedrooms
3,523
Square Feet
0.33
Acres

1591 Cardinal Court, Winter Park, FL 32789

$6,000,000 | 1571 Woodland Avenue, Winter Park, FL 32789
1/74

$6,000,000

5
Bedrooms
7,397
Square Feet
0.38
Acres

1571 Woodland Avenue, Winter Park, FL 32789

$2,099,000 | 938 Enclave Place, Winter Park, FL 32792
1/5

$2,099,000

5
Bedrooms
3,865
Square Feet
0.21
Acres

938 Enclave Place, Winter Park, FL 32792

a front view of a house with a garden and plants
1/3

$2,235,000

5
Bedrooms
4,150
Square Feet
0.21
Acres

926 Enclave Place, Winter Park, FL 32792

$800,000 | 739 Roughbeard Road, Winter Park, FL 32792
1/42

$800,000

5
Bedrooms
2,194
Square Feet
0.25
Acres

739 Roughbeard Road, Winter Park, FL 32792

$1,899,000 | 910 Enclave Place, Winter Park, FL 32792
1/4

$1,899,000

5
Bedrooms
3,620
Square Feet
0.16
Acres

910 Enclave Place, Winter Park, FL 32792

$2,050,000 | 930 Enclave Place, Winter Park, FL 32792
1/4

$2,050,000

5
Bedrooms
3,813
Square Feet
0.21
Acres

930 Enclave Place, Winter Park, FL 32792

a front view of a house with a garden
1/36

$630,000

6
Bedrooms
3,145
Square Feet
0.28
Acres

2600 Euston Road, Winter Park, FL 32789

$630,000 | 2612 Roxbury Road, Winter Park, FL 32789
1/30

$630,000

5
Bedrooms
2,472
Square Feet
0.20
Acres

2612 Roxbury Road, Winter Park, FL 32789

$1,499,999 | 1523 Miller Avenue, Winter Park, FL 32789
1/65

$1,499,999

5
Bedrooms
3,164
Square Feet
0.16
Acres

1523 Miller Avenue, Winter Park, FL 32789

$1,599,900 | 1510 Miller Avenue, Winter Park, FL 32789
1/70
Virtual Tour

$1,599,900

5
Bedrooms
3,252
Square Feet
0.16
Acres

1510 Miller Avenue, Winter Park, FL 32789

a view of a white house with a large tree and a yard in front of it
1/89

$8,950,000

7
Bedrooms
11,255
Square Feet
1.63
Acres

1120 Preserve Point Drive, Winter Park, FL 32789

$1,799,999 | 4469 Old Bear Run, Winter Park, FL 32792
1/77

$1,799,999

5
Bedrooms
4,288
Square Feet
0.74
Acres

4469 Old Bear Run, Winter Park, FL 32792

$3,300,000 | 1627 Mizell Avenue, Winter Park, FL 32789
1/24

$3,300,000

5
Bedrooms
3,421
Square Feet
0.23
Acres

1627 Mizell Avenue, Winter Park, FL 32789

$1,895,000 | 914 Enclave Place, Winter Park, FL 32792
1/3

$1,895,000

5
Bedrooms
3,617
Square Feet
0.17
Acres

914 Enclave Place, Winter Park, FL 32792

$1,599,000 | 1864 Grinnell Terrace, Winter Park, FL 32789
1/43

$1,599,000

5
Bedrooms
3,028
Square Feet
0.21
Acres

1864 Grinnell Terrace, Winter Park, FL 32789

$1,139,750 | 2702 Parkland Drive, Winter Park, FL 32789
1/48

$1,139,750

5
Bedrooms
2,656
Square Feet
0.22
Acres

2702 Parkland Drive, Winter Park, FL 32789

$2,500,000 | 450 Lakewood Drive, Winter Park, FL 32789
1/78

$2,500,000

5
Bedrooms
4,572
Square Feet
0.35
Acres

450 Lakewood Drive, Winter Park, FL 32789

a front view of a house with a blue gate
1/68

$820,000

5
Bedrooms
2,242
Square Feet
0.20
Acres

1927 Eland Avenue, Winter Park, FL 32789

$2,200,000 | 1130 Park N Place, Winter Park, FL 32789
1/39

$2,200,000

5
Bedrooms
4,011
Square Feet
0.40
Acres

1130 Park N Place, Winter Park, FL 32789

$1,649,000 | 2501 Winter Park Road, Winter Park, FL 32789
1/63

$1,649,000

5
Bedrooms
3,304
Square Feet
0.23
Acres

2501 Winter Park Road, Winter Park, FL 32789

$1,900,000 | 785 North Phelps Avenue, Winter Park, FL 32789
1/41

$1,900,000

5
Bedrooms
2,964
Square Feet
0.20
Acres

785 North Phelps Avenue, Winter Park, FL 32789

$2,399,000 | 2838 Wright Avenue, Winter Park, FL 32789
1/10

$2,399,000

5
Bedrooms
3,479
Square Feet
0.23
Acres

2838 Wright Avenue, Winter Park, FL 32789

$6,900,000 | 1260 Alabama Drive, Winter Park, FL 32789
1/58

$6,900,000

6
Bedrooms
6,396
Square Feet
0.57
Acres

1260 Alabama Drive, Winter Park, FL 32789

$2,829,000 | 609 South Phelps Avenue, Winter Park, FL 32789
1/23

$2,829,000

5
Bedrooms
4,018
Square Feet
0.26
Acres

609 South Phelps Avenue, Winter Park, FL 32789

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