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Winter Park is a charming city located in central Florida, just north of Orlando. The city is known for its tree-lined streets, beautiful parks, and historic architecture, as well as its vibrant arts and cultural scene. One of the most prominent features of Winter Park is its picturesque downtown area, which is filled with unique shops, galleries, and restaurants. The downtown area is also home to a number of museums, including the Morse Museum of American Art, which houses the world’s largest collection of works by Louis Comfort Tiffany. Winter Park is also known for its beautiful parks, which offer a variety of recreational activities, including boating, fishing, and hiking. One of the most popular parks in the city is Central Park, which features a beautiful rose garden, a fountain, and a stage that hosts live music performances and events throughout the year. In addition to its natural beauty and cultural attractions, Winter Park is home to a thriving business community, with a mix of small, locally-owned shops and larger, national retailers. The city is also home to several prestigious colleges and universities, including Rollins College, a top-ranked liberal arts college. Winter Park, Florida offers a variety of home communities, ranging from historic neighborhoods to modern developments. Here are some of the popular home communities in Winter Park:
  1. Windsong: A luxurious, gated community with custom-built homes, surrounded by nature preserves and waterways. The community features a private lake, clubhouse, and pool, as well as walking and biking trails.
  2. The Vias: An established neighborhood located in the heart of Winter Park, featuring beautiful homes with mature landscaping, oak trees, and brick streets. The Vias is known for its family-friendly atmosphere and easy access to Winter Park’s shopping and dining destinations.
  3. Lake Virginia: A prestigious neighborhood with a mix of historic and modern homes, many of which have waterfront views. The neighborhood is located near Rollins College and features a variety of outdoor recreational opportunities, including boating, fishing, and kayaking.
  4. Winter Park Village: A mixed-use development featuring luxury condos, townhomes, and apartments, as well as shops, restaurants, and a movie theater. The community offers a convenient location and a walkable lifestyle, with easy access to nearby parks and amenities.
  5. The Oaks of Maitland: A gated community located just outside of Winter Park, featuring custom-built homes on large lots. The community offers a tranquil setting with mature trees, a community pool, and tennis courts.
Overall, Winter Park is a vibrant and thriving city with a unique blend of natural beauty, cultural attractions, and business opportunities. Its small-town charm, coupled with its proximity to the larger city of Orlando, makes it a popular destination for visitors and a great place to call home.
Min. Price
Max. Price
Beds
Baths
1354 INDIANA AVENUE WINTER PARK, FL 32789
$589,900
3 Beds 2 Baths 1,269 SqFt Listing No. O6387500 Property Type: House camera Virtual Tour camera (39)
Details
1120 PRESERVE POINT DRIVE WINTER PARK, FL 32789
$8,950,000
7 Beds 9 | 2 Baths 11,255 SqFt Listing No. O6350054 Property Type: House camera Virtual Tour camera (89)
Details
40 PALMER AVENUE WINTER PARK, FL 32789
$6,950,000
5 Beds 5 | 1 Baths 5,905 SqFt Listing No. O6380444 Property Type: House camera (17)
Details
1260 ALABAMA DRIVE WINTER PARK, FL 32789
$6,900,000
6 Beds 5 | 2 Baths 6,396 SqFt Listing No. O6387200 Property Type: House camera (58)
Details
550 PALMER AVENUE WINTER PARK, FL 32789
$6,495,000
5 Beds 6 | 1 Baths 5,939 SqFt Listing No. O6349188 Property Type: House camera (76)
Details
1200 VIA SALERNO WINTER PARK, FL 32789
$5,995,000
5 Beds 5 | 1 Baths 5,476 SqFt Listing No. O6381761 Property Type: House camera Virtual Tour camera (47)
Details
2211 AZALEA PLACE WINTER PARK, FL 32789
$5,250,000
5 Beds 6 | 1 Baths 7,278 SqFt Listing No. O6319674 Property Type: House camera Virtual Tour camera (99)
Details
643 N PARK AVENUE WINTER PARK, FL 32789
$4,295,000
3 Beds 3 | 2 Baths 4,231 SqFt Listing No. O6403591 Property Type: Condo camera Virtual Tour camera (82)
Details
1441 CARDINAL COURT WINTER PARK, FL 32789
$4,285,000
4 Beds 5 | 1 Baths 4,066 SqFt Listing No. O6399395 Property Type: House camera Virtual Tour camera (85)
Details
141 W LAKE SUE AVENUE WINTER PARK, FL 32789
$4,200,000
5 Beds 5 | 2 Baths 5,500 SqFt Listing No. O6406437 Property Type: House camera Virtual Tour camera (5)
Details
1150 VIA SALERNO WINTER PARK, FL 32789
$4,195,000
4 Beds 5 | 1 Baths 3,850 SqFt Listing No. O6321143 Property Type: House camera Virtual Tour camera (62)
Details
1161 VALENCIA AVENUE WINTER PARK, FL 32789
$4,075,000
4 Beds 4 | 1 Baths 4,181 SqFt Listing No. O6330736 Property Type: House camera Virtual Tour camera (65)
Details
 1354 INDIANA AVENUE, WINTER PARK, FL 32789
camera VIRTUAL TOUR camera (39)
price

$589,900

beds

3 3 Beds

baths

2 2 Baths

lot size

1,269 SqFt 1,269 SqFt

listing no.

O6387500 Listing No. O6387500

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (39)

 1120 PRESERVE POINT DRIVE, WINTER PARK, FL 32789
camera VIRTUAL TOUR camera (89)
price

$8,950,000

beds

7 7 Beds

baths

9 | 2 9 | 2 Baths

lot size

11,255 SqFt 11,255 SqFt

listing no.

O6350054 Listing No. O6350054

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (89)

 40 PALMER AVENUE, WINTER PARK, FL 32789
camera (17)
price

$6,950,000

beds

5 5 Beds

baths

5 | 1 5 | 1 Baths

lot size

5,905 SqFt 5,905 SqFt

listing no.

O6380444 Listing No. O6380444

property type

House Property Type: House

gallery photos

camera (17)

 1260 ALABAMA DRIVE, WINTER PARK, FL 32789
camera (58)
price

$6,900,000

beds

6 6 Beds

baths

5 | 2 5 | 2 Baths

lot size

6,396 SqFt 6,396 SqFt

listing no.

O6387200 Listing No. O6387200

property type

House Property Type: House

gallery photos

camera (58)

 550 PALMER AVENUE, WINTER PARK, FL 32789
camera (76)
price

$6,495,000

beds

5 5 Beds

baths

6 | 1 6 | 1 Baths

lot size

5,939 SqFt 5,939 SqFt

listing no.

O6349188 Listing No. O6349188

property type

House Property Type: House

gallery photos

camera (76)

 1200 VIA SALERNO, WINTER PARK, FL 32789
camera VIRTUAL TOUR camera (47)
price

$5,995,000

beds

5 5 Beds

baths

5 | 1 5 | 1 Baths

lot size

5,476 SqFt 5,476 SqFt

listing no.

O6381761 Listing No. O6381761

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (47)

 2211 AZALEA PLACE, WINTER PARK, FL 32789
camera VIRTUAL TOUR camera (99)
price

$5,250,000

beds

5 5 Beds

baths

6 | 1 6 | 1 Baths

lot size

7,278 SqFt 7,278 SqFt

listing no.

O6319674 Listing No. O6319674

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (99)

 643 N PARK AVENUE, WINTER PARK, FL 32789
camera VIRTUAL TOUR camera (82)
price

$4,295,000

beds

3 3 Beds

baths

3 | 2 3 | 2 Baths

lot size

4,231 SqFt 4,231 SqFt

listing no.

O6403591 Listing No. O6403591

property type

Condo Property Type: Condo

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (82)

 1441 CARDINAL COURT, WINTER PARK, FL 32789
camera VIRTUAL TOUR camera (85)
price

$4,285,000

beds

4 4 Beds

baths

5 | 1 5 | 1 Baths

lot size

4,066 SqFt 4,066 SqFt

listing no.

O6399395 Listing No. O6399395

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (85)

 141 W LAKE SUE AVENUE, WINTER PARK, FL 32789
camera VIRTUAL TOUR camera (5)
price

$4,200,000

beds

5 5 Beds

baths

5 | 2 5 | 2 Baths

lot size

5,500 SqFt 5,500 SqFt

listing no.

O6406437 Listing No. O6406437

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (5)

 1150 VIA SALERNO, WINTER PARK, FL 32789
camera VIRTUAL TOUR camera (62)
price

$4,195,000

beds

4 4 Beds

baths

5 | 1 5 | 1 Baths

lot size

3,850 SqFt 3,850 SqFt

listing no.

O6321143 Listing No. O6321143

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (62)

 1161 VALENCIA AVENUE, WINTER PARK, FL 32789
camera VIRTUAL TOUR camera (65)
price

$4,075,000

beds

4 4 Beds

baths

4 | 1 4 | 1 Baths

lot size

4,181 SqFt 4,181 SqFt

listing no.

O6330736 Listing No. O6330736

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (65)

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Stellar (MFR) data last updated at May 28, 2026, 1:25 AM ET
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