42 total properties
Did you mean the neighborhood Winter Park?
View 2824 PRINCE JOHN ROAD Winter Park, FL MLS# O6435708
  • Recently Listed
1 of 18
$475,000
2

Beds

2.0

Baths

1,438

Sq.Ft.

2824 PRINCE JOHN ROAD

Winter Park, FL

View 2765 ABBEY ROAD Winter Park, FL MLS# O6434420
  • Virtual Tour
1 of 5
$430,000
3

Beds

2.0

Baths

1,620

Sq.Ft.

2765 ABBEY ROAD

Winter Park, FL

View 2183 CRANDON AVENUE Winter Park, FL MLS# O6433521
  • Recently Listed
1 of 28
$499,000
4

Beds

2.0

Baths

1,200

Sq.Ft.

2183 CRANDON AVENUE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1955 ELAND AVENUE Winter Park, FL MLS# O6433345
  • Recently Listed with Virtual Tour
1 of 19
$439,000
3

Beds

2.0

Baths

1,494

Sq.Ft.

1955 ELAND AVENUE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 351 STARLING ROAD Winter Park, FL MLS# O6429698
$499,900
3

Beds

1.1

Baths

1,979

Sq.Ft.

351 STARLING ROAD

Winter Park, FL

View 2781 ABBEY ROAD Winter Park, FL MLS# O6429991
  • Virtual Tour
1 of 29
$520,000
3

Beds

2.0

Baths

1,596

Sq.Ft.

2781 ABBEY ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1061 ARAGON AVENUE 1061 Winter Park, FL MLS# S5152353
$510,000
3

Beds

2.1

Baths

1,669

Sq.Ft.

1061 ARAGON AVENUE 1061

Winter Park, FL

Courtesy of WATSON REALTY CORP
View 2552 BROOKSHIRE AVENUE Winter Park, FL MLS# O6428975
$530,000
3

Beds

1.1

Baths

1,314

Sq.Ft.

2552 BROOKSHIRE AVENUE

Winter Park, FL

View 405 Lake Fair Lane Winter Park, FL MLS# A12062271
  • Virtual Tour
1 of 18
$434,990
3

Beds

2.0

Baths

405 Lake Fair Lane

Winter Park, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 651 DARCEY DRIVE Winter Park, FL MLS# O6428379
$500,000
4

Beds

2.0

Baths

1,866

Sq.Ft.

651 DARCEY DRIVE

Winter Park, FL

View 2826 AMBERGATE ROAD Winter Park, FL MLS# O6427973
  • Virtual Tour
1 of 46
$460,000
3

Beds

2.0

Baths

1,521

Sq.Ft.

2826 AMBERGATE ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2007 CORNELL AVENUE Winter Park, FL MLS# O6428423
  • Recently Listed with Virtual Tour
1 of 35
$449,000
3

Beds

2.0

Baths

1,154

Sq.Ft.

2007 CORNELL AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 230 STRATHY LANE Winter Park, FL MLS# O6426909
$499,000
920

Sq.Ft.

230 STRATHY LANE

Winter Park, FL

View 2231 NAIRN DRIVE Winter Park, FL MLS# O6426997
$499,000
1,088

Sq.Ft.

2231 NAIRN DRIVE

Winter Park, FL

View 1909 TAYLOR AVENUE Winter Park, FL MLS# O6426549
$425,000
Studio

Beds

0.0

Baths

1909 TAYLOR AVENUE

Winter Park, FL

View 2568 LOTAFUN AVENUE Winter Park, FL MLS# W7887744
  • Virtual Tour
1 of 25
$409,900
3

Beds

2.0

Baths

1,201

Sq.Ft.

2568 LOTAFUN AVENUE

Winter Park, FL

View 1134 WASHINGTON AVENUE 13C Winter Park, FL MLS# O6416746
$525,000
3

Beds

3.1

Baths

2,195

Sq.Ft.

1134 WASHINGTON AVENUE 13C

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 4437 GLENMOOR COURT Winter Park, FL MLS# O6424511
  • Virtual Tour
1 of 32
$525,000
3

Beds

2.0

Baths

2,633

Sq.Ft.

4437 GLENMOOR COURT

Winter Park, FL

View 7509 GLENMOOR LANE Winter Park, FL MLS# O6421887
  • Virtual Tour
1 of 45
$499,500
3

Beds

2.0

Baths

2,067

Sq.Ft.

7509 GLENMOOR LANE

Winter Park, FL

View 2041 JEWELL AVENUE Winter Park, FL MLS# O6420660
  • Virtual Tour
1 of 30
$439,900
3

Beds

1.0

Baths

1,508

Sq.Ft.

2041 JEWELL AVENUE

Winter Park, FL

Courtesy of IAD REAL ESTATE

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

373

Estimated median home price

$695,000
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 32
$500K - 600K 34
$600K - 700K 38
$700K - 800K 14
$800K - 900K 11
$900K - 1M 11
$1M - Max 147

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 226
Townhouse 22
Condo 85
Commercial 9
Rental 80
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 5
Mobile Home 0
Farms 0

(Data as of 8/22/2026)

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 8/23/2026.