11 total properties
Did you mean the neighborhood Winter Park?
View 313 SYLVAN DRIVE Winter Park, FL MLS# O6407606
  • Recently Listed with Virtual Tour
1 of 10
$5,500,000
4

Beds

4.1

Baths

4,775

Sq.Ft.

313 SYLVAN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2228 AZALEA PLACE Winter Park, FL MLS# O6416342
  • Recently Listed with Virtual Tour
1 of 72
$5,600,000
5

Beds

5.1

Baths

5,152

Sq.Ft.

2228 AZALEA PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1571 WOODLAND AVENUE Winter Park, FL MLS# O6411706
  • Virtual Tour
1 of 75
$6,000,000
5

Beds

6.2

Baths

7,397

Sq.Ft.

1571 WOODLAND AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 2661 Via Tuscany Winter Park, FL MLS# B26030158
  • New Construction with Virtual Tour
1 of 44
$6,888,888
4

Beds

4.1

Baths

4,636

Sq.Ft.

2661 Via Tuscany

Winter Park, FL

View 1260 ALABAMA DRIVE Winter Park, FL MLS# O6387200
$6,900,000
6

Beds

5.2

Baths

6,396

Sq.Ft.

1260 ALABAMA DRIVE

Winter Park, FL

View 1200 VIA SALERNO Winter Park, FL MLS# O6381761
  • Virtual Tour
1 of 47
$5,995,000
5

Beds

5.1

Baths

5,476

Sq.Ft.

1200 VIA SALERNO

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 40 PALMER AVENUE Winter Park, FL MLS# O6380444
  • New Construction
1 of 17
$6,950,000
5

Beds

5.1

Baths

5,905

Sq.Ft.

40 PALMER AVENUE

Winter Park, FL

View 550 PALMER AVENUE Winter Park, FL MLS# O6349188
  • New Construction with Virtual Tour
1 of 76
$6,495,000
5

Beds

6.1

Baths

5,939

Sq.Ft.

550 PALMER AVENUE

Winter Park, FL

View 2211 Azalea Pl Winter Park, FL MLS# A11824988
  • Virtual Tour
1 of 98
$5,250,000
5

Beds

6.1

Baths

7,278

Sq.Ft.

2211 Azalea Pl

Winter Park, FL

Courtesy of FORTUNE CHRISTIE'S INTERNATIONAL REAL ESTATE
View 2211 Azalea Place Winter Park, FL MLS# A11824988
  • Adult Community with Virtual Tour
1 of 394
$5,250,000
5

Beds

6.1

Baths

7,278

Sq.Ft.

2211 Azalea Place

Winter Park, FL

View 2211 AZALEA PLACE Winter Park, FL MLS# O6319674
  • Virtual Tour
1 of 99
$5,250,000
5

Beds

6.1

Baths

7,278

Sq.Ft.

2211 AZALEA PLACE

Winter Park, FL

Courtesy of FORTUNE INTERNATIONAL REALTY

About Winter Park

Long considered one of the most desirable addresses in Central Florida, Winter Park has been experiencing a wave of new construction along with revitalization of historic areas.  In some instances, developers are choosing to raze older buildings and replace them with luxurious new homes, some that surpass the $1 million price range.  Handsome new residential villages can include exceptional amenities like lakefront parks, pools, and nature preserves.  Winter Park offers a number of amenities that are unusual for a smaller town, including the Rollins College.  This highly respected, private, liberal arts college with its lush campus enriches the entire community educationally, culturally, and economically.  However, the college is not the town's only point of pride.  One of the world's most comprehensive collections of the works of Louis Comfort Tiffany is permanently housed in the Charles Hosmer Morse Museum of American Art.  Aficionados of shopping are drawn to Park Avenue, a quaint district where an oak-shaded park and bandstand are surrounded by art galleries, museums, clothing stores, retail outlets, and wonderful boutiques.  

Listings in Winter Park, FL

395

Estimated median home price

$750,000
Winter Park FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Park, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Park, FL.

Homes for Sale by Price in Winter Park, FL

Price Count
$0 - 100K 3
$100K - 200K 48
$200K - 300K 26
$300K - 400K 19
$400K - 500K 30
$500K - 600K 29
$600K - 700K 34
$700K - 800K 17
$800K - 900K 12
$900K - 1M 9
$1M - Max 168

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 248
Townhouse 17
Condo 94
Commercial 7
Rental 67
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/2/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

Listing information courtesy of My Florida Regional MLS DBA 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; availability of any listing should always be independently verified. Listing information is provided for consumer 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.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 7/2/2026.