219 total properties
Did you mean the neighborhood Winter Park?
View 1404 BORDER DRIVE Winter Park, FL MLS# O6412140
  • Virtual Tour
1 of 38
$1,100,000
4

Beds

4.0

Baths

2,469

Sq.Ft.

1404 BORDER DRIVE

Winter Park, FL

View 1768 MONDRIAN CIRCLE Winter Park, FL MLS# O6375723
  • Virtual Tour
1 of 26
$1,099,000
3

Beds

3.1

Baths

2,193

Sq.Ft.

1768 MONDRIAN CIRCLE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1120 WISCONSIN AVENUE Winter Park, FL MLS# O6406800
$1,084,000
3

Beds

3.1

Baths

2,213

Sq.Ft.

1120 WISCONSIN AVENUE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 632 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6250417
$1,050,000
3

Beds

2.0

Baths

2,342

Sq.Ft.

632 COUNTRY CLUB DRIVE

Winter Park, FL

View 2702 PARKLAND DRIVE Winter Park, FL MLS# O6397997
  • Virtual Tour
1 of 48
$1,049,000
5

Beds

3.0

Baths

2,656

Sq.Ft.

2702 PARKLAND DRIVE

Winter Park, FL

View 1138 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6420090
$1,025,000
3

Beds

3.0

Baths

2,434

Sq.Ft.

1138 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1725 CAROLLEE LANE Winter Park, FL MLS# O6402656
  • Virtual Tour
1 of 41
$1,005,000
3

Beds

2.0

Baths

2,335

Sq.Ft.

1725 CAROLLEE LANE

Winter Park, FL

View 2667 COCHISE TRAIL Winter Park, FL MLS# O6429844
  • Recently Listed with Virtual Tour
1 of 92
$1,000,050
4

Beds

3.0

Baths

2,868

Sq.Ft.

2667 COCHISE TRAIL

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1836 GRINNELL TERRACE Winter Park, FL MLS# O6380457
$999,000
3

Beds

2.0

Baths

1,907

Sq.Ft.

1836 GRINNELL TERRACE

Winter Park, FL

View 1836 GRINNELL TERRACE Winter Park, FL MLS# O6395188
$999,000
Studio

Beds

0.0

Baths

1836 GRINNELL TERRACE

Winter Park, FL

View 616 BRECHIN DRIVE Winter Park, FL MLS# O6409911
  • Virtual Tour
1 of 44
$999,000
4

Beds

4.1

Baths

2,638

Sq.Ft.

616 BRECHIN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1741 MIZELL AVENUE Winter Park, FL MLS# O6410059
  • Virtual Tour
1 of 41
$998,000
3

Beds

2.0

Baths

2,015

Sq.Ft.

1741 MIZELL AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1611 CHESTNUT AVENUE Winter Park, FL MLS# O6402502
  • Virtual Tour
1 of 51
$995,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

1611 CHESTNUT AVENUE

Winter Park, FL

View 241 W LAKE SUE AVENUE Winter Park, FL MLS# O6411621
$995,000
3

Beds

2.1

Baths

2,304

Sq.Ft.

241 W LAKE SUE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1800 MAGNOLIA AVENUE Winter Park, FL MLS# NS1087637
$994,000
4

Beds

2.1

Baths

2,431

Sq.Ft.

1800 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 269 E CANTON AVENUE 269 Winter Park, FL MLS# O6404706
$989,500
1

Beds

1.1

Baths

1,109

Sq.Ft.

269 E CANTON AVENUE 269

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 731 MIDGET DRIVE Winter Park, FL MLS# O6368705
  • Virtual Tour
1 of 7
$940,000
Studio

Beds

0.0

Baths

731 MIDGET DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 1310 FAIRVIEW AVENUE Winter Park, FL MLS# O6424108
  • Virtual Tour
1 of 14
$925,000
4

Beds

2.1

Baths

2,552

Sq.Ft.

1310 FAIRVIEW AVENUE

Winter Park, FL

Courtesy of FLORIDA PROPERTY SPECIALIST
View Lot #21 KAROLINA AVE Winter Park, FL MLS# O6387812
  • New Construction with Virtual Tour
1 of 9
$918,000
4

Beds

2.1

Baths

2,662

Sq.Ft.

Lot #21 KAROLINA AVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6398302
  • Virtual Tour
1 of 18
$899,900
Studio

Beds

0.0

Baths

2823 WRIGHT AVENUE

Winter Park, FL

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

359

Estimated median home price

$725,000
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 7
$100K - 200K 41
$200K - 300K 23
$300K - 400K 15
$400K - 500K 34
$500K - 600K 25
$600K - 700K 32
$700K - 800K 15
$800K - 900K 12
$900K - 1M 10
$1M - Max 145

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 217
Townhouse 21
Condo 80
Commercial 10
Rental 74
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 8/4/2026)

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 Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes 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 8/4/2026.

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 8/4/2026.