Winter Park Homes for Sale

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$1,750,000

1630 CHESTNUT AVENUE
WINTER PARK, FL 32789

1

3
Beds

4 | 1
Baths

3,164
SqFt

(55)

1630 CHESTNUT AVENUE, WINTER PARK, FL 32789 

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Open House: Nov 16, 2025, 2:00 PM - 4:00 PM

 

#O6360357 | House

 

$1,390,000

501 LAKEVIEW AVENUE
WINTER PARK, FL 32789

2

4
Beds

4 | 1
Baths

3,253
SqFt

(7)

501 LAKEVIEW AVENUE, WINTER PARK, FL 32789 

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#O6325192 | House

 

$1,390,000

525 LAKEVIEW AVENUE
WINTER PARK, FL 32789

3

4
Beds

4 | 1
Baths

3,253
SqFt

(7)

525 LAKEVIEW AVENUE, WINTER PARK, FL 32789 

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#O6325165 | House

 

$950,000

668 OVERSPIN DRIVE
WINTER PARK, FL 32789

4

4
Beds

3
Baths

2,509
SqFt

(54)

668 OVERSPIN DRIVE, WINTER PARK, FL 32789 

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#O6351255 | House

 

$749,000

2955 LOLISSA LANE
WINTER PARK, FL 32789

5

4
Beds

3
Baths

3,538
SqFt

(58)

2955 LOLISSA LANE, WINTER PARK, FL 32789 

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#O6345484 | House

 

$415,000

1872 BISCAYNE DRIVE
WINTER PARK, FL 32789

6

2
Beds

1
Baths

969
SqFt

(23)

1872 BISCAYNE DRIVE, WINTER PARK, FL 32789 

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Open House: Nov 16, 2025, 1:00 PM - 3:00 PM

 

#O6358984 | House

 

$8,950,000

1120 PRESERVE POINT DRIVE
WINTER PARK, FL 32789

7

7
Beds

9 | 2
Baths

11,255
SqFt

(85)

1120 PRESERVE POINT DRIVE, WINTER PARK, FL 32789 

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#O6350054 | House

 

$8,500,000

1112 PRESERVE POINT DRIVE
WINTER PARK, FL 32789

8

5
Beds

6
Baths

6,502
SqFt

(88)

1112 PRESERVE POINT DRIVE, WINTER PARK, FL 32789 

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#O6312768 | House

 

$7,200,000

550 PALMER AVENUE
WINTER PARK, FL 32789

9

5
Beds

6 | 1
Baths

5,939
SqFt

(62)

550 PALMER AVENUE, WINTER PARK, FL 32789 

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#O6349188 | House

 

$6,600,000

2661 VIA TUSCANY
WINTER PARK, FL 32789

10

4
Beds

4 | 1
Baths

4,636
SqFt

(100)

2661 VIA TUSCANY, WINTER PARK, FL 32789 

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#O6260493 | House

 

$5,900,000

887 GEORGIA AVENUE
WINTER PARK, FL 32789

11

6
Beds

5 | 1
Baths

5,759
SqFt

(51)

887 GEORGIA AVENUE, WINTER PARK, FL 32789 

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#O6331715 | House

 

$5,895,000

1400 ALABAMA DRIVE
WINTER PARK, FL 32789

12

5
Beds

5 | 4
Baths

7,916
SqFt

(84)

1400 ALABAMA DRIVE, WINTER PARK, FL 32789 

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#O6285791 | House

 

$5,675,000

1860 SUMMERLAND AVENUE
WINTER PARK, FL 32789

13

5
Beds

4 | 2
Baths

5,022
SqFt

(78)

1860 SUMMERLAND AVENUE, WINTER PARK, FL 32789 

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#O6358159 | House

 

$5,495,000

2211 AZALEA PLACE
WINTER PARK, FL 32789

14

5
Beds

6 | 1
Baths

7,278
SqFt

(99)

2211 AZALEA PLACE, WINTER PARK, FL 32789 

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Open House: Nov 23, 2025, 12:00 PM - 2:00 PM

 

#O6319674 | House

 

$5,450,000

1221 RICHMOND ROAD
WINTER PARK, FL 32789

15

5
Beds

5 | 1
Baths

5,164
SqFt

(52)

1221 RICHMOND ROAD, WINTER PARK, FL 32789 

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#O6321906 | House

 

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The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Stellar (MFR) data last updated at November 15, 2025, 12:52 AM ET