360 total properties
Did you mean the neighborhood Winter Park?
View 901 GOLFVIEW TERRACE Winter Park, FL MLS# O6437917
  • Virtual Tour
1 of 49
$6,995,000
5

Beds

5.1

Baths

5,479

Sq.Ft.

901 GOLFVIEW TERRACE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1260 ALABAMA DRIVE Winter Park, FL MLS# O6387200
  • Virtual Tour
1 of 58
$6,900,000
6

Beds

5.2

Baths

6,396

Sq.Ft.

1260 ALABAMA DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 698 N NEW YORK AVENUE Winter Park, FL MLS# O6439388
  • New Construction with Virtual Tour
1 of 52
$6,195,000
5

Beds

5.1

Baths

5,096

Sq.Ft.

698 N NEW YORK AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
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
View 1011 MCKEAN CIRCLE Winter Park, FL MLS# O6449269
  • Recently Listed with Virtual Tour
1 of 70
$6,000,000
5

Beds

5.2

Baths

4,806

Sq.Ft.

1011 MCKEAN CIRCLE

Winter Park, FL

Courtesy of UNITED REAL ESTATE PREFERRED
View 2228 AZALEA PLACE Winter Park, FL MLS# O6416342
  • Virtual Tour
1 of 34
$5,600,000
5

Beds

5.1

Baths

5,152

Sq.Ft.

2228 AZALEA PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2661 VIA TUSCANY Winter Park, FL MLS# O6439181
  • New Construction with Virtual Tour
1 of 68
$5,500,000
4

Beds

4.1

Baths

3,880

Sq.Ft.

2661 VIA TUSCANY

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1166 PALMER AVENUE Winter Park, FL MLS# O6442798
  • New Construction with Virtual Tour
1 of 19
$5,500,000
5

Beds

5.2

Baths

5,181

Sq.Ft.

1166 PALMER AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
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 825 PALMER AVENUE Winter Park, FL MLS# O6435679
  • New Construction
1 of 7
$5,195,900
5

Beds

5.2

Baths

5,122

Sq.Ft.

825 PALMER AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 231 CHELTON CIRCLE Winter Park, FL MLS# O6414890
  • Virtual Tour
1 of 67
$4,700,000
4

Beds

5.2

Baths

5,550

Sq.Ft.

231 CHELTON CIRCLE

Winter Park, FL

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
View 617 N INTERLACHEN AVENUE Winter Park, FL MLS# R4912183
$4,695,000
11

Beds

7.1

Baths

3,615

Sq.Ft.

617 N INTERLACHEN AVENUE

Winter Park, FL

Courtesy of EASY REALTY
View 1525 GRANVILLE DRIVE Winter Park, FL MLS# O6422951
  • New Construction with Virtual Tour
1 of 56
$4,595,000
5

Beds

5.1

Baths

5,211

Sq.Ft.

1525 GRANVILLE DRIVE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 503 N INTERLACHEN AVENUE Winter Park, FL MLS# O6331207
$4,500,000
0.0

Baths

503 N INTERLACHEN AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 857 BROCK STREET Winter Park, FL MLS# O6432219
  • New Construction with Virtual Tour
1 of 11
$4,350,000
5

Beds

5.1

Baths

4,827

Sq.Ft.

857 BROCK STREET

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 2403 EUSTON ROAD Winter Park, FL MLS# O6434678
  • Virtual Tour
1 of 11
$4,299,000
0.0

Baths

2403 EUSTON ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 702 VIA BELLA Winter Park, FL MLS# O6437125
  • Virtual Tour
1 of 41
$4,250,000
4

Beds

5.1

Baths

3,720

Sq.Ft.

702 VIA BELLA

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1441 CARDINAL COURT Winter Park, FL MLS# O6399395
  • Virtual Tour
1 of 85
$3,995,000
4

Beds

5.1

Baths

4,066

Sq.Ft.

1441 CARDINAL COURT

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 540 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6431538
$3,950,000
0.0

Baths

540 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 540 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6436046
$3,950,000
4

Beds

2.0

Baths

1,652

Sq.Ft.

540 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER 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

357

Estimated median home price

$769,000
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 2
$100K - 200K 35
$200K - 300K 22
$300K - 400K 20
$400K - 500K 30
$500K - 600K 27
$600K - 700K 34
$700K - 800K 17
$800K - 900K 14
$900K - 1M 14
$1M - Max 142

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 210
Townhouse 20
Condo 77
Commercial 15
Rental 85
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 10/18/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

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

Data is updated as of 10/20/2026.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties 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 10/20/2026.