58 total properties
Did you mean the neighborhood Winter Park?
View 1037 N VIRGINIA AVENUE Winter Park, FL MLS# O6419694
  • Recently Listed with Virtual Tour
1 of 35
$649,000
3

Beds

1.0

Baths

1,101

Sq.Ft.

1037 N VIRGINIA AVENUE

Winter Park, FL

View 1037 N VIRGINIA AVENUE Winter Park, FL MLS# O6419696
$649,000
Studio

Beds

0.0

Baths

1037 N VIRGINIA AVENUE

Winter Park, FL

View 981 ARAGON AVENUE Winter Park, FL MLS# O6420093
  • Recently Listed with Virtual Tour
1 of 7
$535,000
2

Beds

1.0

Baths

857

Sq.Ft.

981 ARAGON AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 2774 BANCHORY ROAD Winter Park, FL MLS# O6418821
  • Recently Listed
1 of 34
$645,000
3

Beds

2.0

Baths

1,560

Sq.Ft.

2774 BANCHORY ROAD

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1003 LAKE BELL DRIVE Winter Park, FL MLS# O6418278
$649,900
3

Beds

2.0

Baths

1,837

Sq.Ft.

1003 LAKE BELL DRIVE

Winter Park, FL

View 2652 ABBEY ROAD Winter Park, FL MLS# O6419026
  • Virtual Tour
1 of 44
$625,000
5

Beds

2.0

Baths

1,938

Sq.Ft.

2652 ABBEY ROAD

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 332 FLEET ROAD Winter Park, FL MLS# O6414829
  • Virtual Tour
1 of 35
$595,000
4

Beds

2.0

Baths

2,355

Sq.Ft.

332 FLEET ROAD

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 4053 COOL WATER COURT Winter Park, FL MLS# O6419831
$549,000
3

Beds

2.0

Baths

1,930

Sq.Ft.

4053 COOL WATER COURT

Winter Park, FL

View 2361 ROXBURY ROAD Winter Park, FL MLS# O6418164
  • Recently Listed with Virtual Tour
1 of 34
$599,000
3

Beds

2.0

Baths

1,723

Sq.Ft.

2361 ROXBURY ROAD

Winter Park, FL

View 528 SAINT DUNSTAN WAY Winter Park, FL MLS# O6414677
  • Recently Listed with Virtual Tour
1 of 35
$535,000
3

Beds

2.0

Baths

1,656

Sq.Ft.

528 SAINT DUNSTAN WAY

Winter Park, FL

View 685 OVERSPIN DRIVE Winter Park, FL MLS# O6415537
$629,000
3

Beds

2.1

Baths

2,112

Sq.Ft.

685 OVERSPIN DRIVE

Winter Park, FL

View 1250 FORMOSA AVENUE Winter Park, FL MLS# O6412954
$560,000
3

Beds

3.1

Baths

1,937

Sq.Ft.

1250 FORMOSA AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 860 N DENNING DRIVE Winter Park, FL MLS# O6412589
$699,900
3

Beds

2.1

Baths

1,411

Sq.Ft.

860 N DENNING DRIVE

Winter Park, FL

View 508 DUNRAVEN DRIVE Winter Park, FL MLS# O6412363
$595,000
3

Beds

2.0

Baths

1,370

Sq.Ft.

508 DUNRAVEN DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 2157 LAKE DRIVE Winter Park, FL MLS# O6412258
  • Virtual Tour
1 of 45
$689,000
3

Beds

3.0

Baths

2,124

Sq.Ft.

2157 LAKE DRIVE

Winter Park, FL

Courtesy of SHORES REAL ESTATE
View 840 W CANTON AVENUE Winter Park, FL MLS# O6412754
$675,000
3

Beds

2.0

Baths

1,370

Sq.Ft.

840 W CANTON AVENUE

Winter Park, FL

View 1946 STRATHAVEN ROAD Winter Park, FL MLS# O6411329
$650,000
4

Beds

2.0

Baths

2,102

Sq.Ft.

1946 STRATHAVEN ROAD

Winter Park, FL

View 1821 KILLARNEY DRIVE Winter Park, FL MLS# O6410660
$599,999
Studio

Beds

0.0

Baths

1821 KILLARNEY DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 333 CORNWALL ROAD Winter Park, FL MLS# O6409379
$579,000
4

Beds

2.0

Baths

1,660

Sq.Ft.

333 CORNWALL ROAD

Winter Park, FL

View 1009 LAKE BELL DRIVE Winter Park, FL MLS# O6409849
$650,000
3

Beds

2.0

Baths

1,467

Sq.Ft.

1009 LAKE BELL DRIVE

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

404

Estimated median home price

$742,000
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

PriceCount
$0 - 100K3
$100K - 200K48
$200K - 300K25
$300K - 400K20
$400K - 500K33
$500K - 600K30
$600K - 700K34
$700K - 800K19
$800K - 900K13
$900K - 1M9
$1M - Max170

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family258
Townhouse16
Condo94
Commercial7
Rental71
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 6/30/2026)

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 7/1/2026.

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 7/1/2026.