126 total properties
Did you mean the neighborhood Winter Park?
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5137596
  • Virtual Tour
1 of 30
$630,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5139410
  • Virtual Tour
1 of 37
$630,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
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

The time to sell is now! THE TIME TO SELL IS NOW!
View 1946 STRATHAVEN ROAD Winter Park, FL MLS# O6411329
  • Virtual Tour
1 of 37
$625,000
4

Beds

2.0

Baths

2,102

Sq.Ft.

1946 STRATHAVEN ROAD

Winter Park, FL

View 2708 LION HEART ROAD Winter Park, FL MLS# O6387685
  • Virtual Tour
1 of 47
$615,000
3

Beds

2.0

Baths

1,785

Sq.Ft.

2708 LION HEART ROAD

Winter Park, FL

View 2824 WOODSIDE AVENUE Winter Park, FL MLS# O6423146
$600,000
2

Beds

2.0

Baths

912

Sq.Ft.

2824 WOODSIDE AVENUE

Winter Park, FL

Courtesy of PARKSIDE PROPERTIES, LLC
View 2758 BANCHORY ROAD Winter Park, FL MLS# O6329628
  • Virtual Tour
1 of 37
$598,000
3

Beds

2.1

Baths

1,539

Sq.Ft.

2758 BANCHORY ROAD

Winter Park, FL

Courtesy of MR VARGAS PROPERTY MANAGEMENT LLC
View 1741 WESTCHESTER AVENUE Winter Park, FL MLS# O6399014
$595,000
3

Beds

2.0

Baths

1,434

Sq.Ft.

1741 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
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 2010 SUMMERFIELD ROAD Winter Park, FL MLS# O6420140
  • Recently Listed with Virtual Tour
1 of 40
$594,500
3

Beds

2.0

Baths

1,889

Sq.Ft.

2010 SUMMERFIELD ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1319 BESSMOR ROAD Winter Park, FL MLS# O6400395
  • Virtual Tour
1 of 13
$589,000
3

Beds

2.0

Baths

1,126

Sq.Ft.

1319 BESSMOR ROAD

Winter Park, FL

Courtesy of GALLOWAY REAL ESTATE
View 2803 RIDDLE DRIVE Winter Park, FL MLS# O6423829
  • Recently Listed
1 of 35
$589,000
3

Beds

2.1

Baths

1,637

Sq.Ft.

2803 RIDDLE DRIVE

Winter Park, FL

View 333 CORNWALL ROAD Winter Park, FL MLS# O6409379
  • Virtual Tour
1 of 32
$579,000
4

Beds

2.0

Baths

1,660

Sq.Ft.

333 CORNWALL ROAD

Winter Park, FL

View 1122 WASHINGTON AVENUE 7B Winter Park, FL MLS# O6421299
  • Recently Listed with Virtual Tour
1 of 53
$575,000
2

Beds

2.1

Baths

1,556

Sq.Ft.

1122 WASHINGTON AVENUE 7B

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 1354 INDIANA AVENUE Winter Park, FL MLS# O6387500
  • Virtual Tour
1 of 39
$574,900
3

Beds

2.0

Baths

1,269

Sq.Ft.

1354 INDIANA AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 517 ROUGHBEARD ROAD Winter Park, FL MLS# O6399029
  • Virtual Tour
1 of 53
$565,000
3

Beds

2.0

Baths

1,873

Sq.Ft.

517 ROUGHBEARD ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1250 FORMOSA AVENUE Winter Park, FL MLS# O6412954
  • Virtual Tour
1 of 37
$560,000
3

Beds

3.1

Baths

1,937

Sq.Ft.

1250 FORMOSA AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1809 HAMMERLIN AVENUE Winter Park, FL MLS# O6373616
$549,000
3

Beds

2.1

Baths

1,818

Sq.Ft.

1809 HAMMERLIN AVENUE

Winter Park, FL

View 4033 YACHT COURT Winter Park, FL MLS# O6379135
  • Virtual Tour
1 of 26
$549,000
3

Beds

2.0

Baths

2,268

Sq.Ft.

4033 YACHT COURT

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
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

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

306

Estimated median home price

$735,000
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 4
$100K - 200K 41
$200K - 300K 18
$300K - 400K 14
$400K - 500K 25
$500K - 600K 21
$600K - 700K 24
$700K - 800K 11
$800K - 900K 11
$900K - 1M 5
$1M - Max 132

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 186
Townhouse 14
Condo 73
Commercial 7
Rental 72
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/10/2026)

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 7/11/2026.