29 total properties
Did you mean the neighborhood Winter Park?
View 1941 OGLESBY AVENUE Winter Park, FL MLS# N6145448
  • Recently Listed with Virtual Tour
1 of 30
$340,000
2

Beds

1.0

Baths

780

Sq.Ft.

1941 OGLESBY AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 2765 ABBEY ROAD Winter Park, FL MLS# O6434420
$430,000
3

Beds

2.0

Baths

1,620

Sq.Ft.

2765 ABBEY ROAD

Winter Park, FL

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
The time to sell is now! THE TIME TO SELL IS NOW!
View 310 GRANADA DRIVE Winter Park, FL MLS# TB8536242
$354,999
3

Beds

2.0

Baths

1,344

Sq.Ft.

310 GRANADA DRIVE

Winter Park, FL

Courtesy of A-WARD WINNING REALTY LLC
View 405 Lake Fair Lane Winter Park, FL MLS# A12062271
$434,990
3

Beds

2.0

Baths

405 Lake Fair Lane

Winter Park, FL

Courtesy of AGENT TRUST REALTY CORPORATION
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 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
$409,900
3

Beds

2.0

Baths

1,201

Sq.Ft.

2568 LOTAFUN AVENUE

Winter Park, FL

View 2526 PASSAMONTE DRIVE 10F Winter Park, FL MLS# O6418710
$335,000
3

Beds

2.1

Baths

1,790

Sq.Ft.

2526 PASSAMONTE DRIVE 10F

Winter Park, FL

View 4965 ORANGE AVENUE Winter Park, FL MLS# O6423739
$370,000
4

Beds

2.0

Baths

1,444

Sq.Ft.

4965 ORANGE AVENUE

Winter Park, FL

View 885 CARNATION DRIVE Winter Park, FL MLS# S5153456
$385,000
4

Beds

2.0

Baths

1,240

Sq.Ft.

885 CARNATION DRIVE

Winter Park, FL

View 2041 JEWELL AVENUE Winter Park, FL MLS# O6420660
$439,900
3

Beds

1.0

Baths

1,508

Sq.Ft.

2041 JEWELL AVENUE

Winter Park, FL

Courtesy of IAD REAL ESTATE
View 644 N KNOWLES AVENUE 3 Winter Park, FL MLS# O6420484
$424,400
1

Beds

1.0

Baths

767

Sq.Ft.

644 N KNOWLES AVENUE 3

Winter Park, FL

View JESSICA COURT Winter Park, FL MLS# O6419256
  • Virtual Tour
1 of 11
$449,000
Studio

Beds

0.0

Baths

JESSICA COURT

Winter Park, FL

View 2323 DEVON COURT Winter Park, FL MLS# O6418530
  • Virtual Tour
1 of 35
$429,000
4

Beds

2.0

Baths

2,403

Sq.Ft.

2323 DEVON COURT

Winter Park, FL

View 316 BECKETT COURT Winter Park, FL MLS# O6411108
$450,000
4

Beds

2.0

Baths

1,651

Sq.Ft.

316 BECKETT COURT

Winter Park, FL

Courtesy of VINTAGE REALTY SOLUTIONS
View 700 MELROSE AVENUE J24 Winter Park, FL MLS# R4911307
  • Adult Community with Virtual Tour
1 of 28
$350,000
1

Beds

1.0

Baths

987

Sq.Ft.

700 MELROSE AVENUE J24

Winter Park, FL

View 1092 EASTBROOK BOULEVARD Winter Park, FL MLS# O6407251
$399,000
3

Beds

2.0

Baths

1,122

Sq.Ft.

1092 EASTBROOK BOULEVARD

Winter Park, FL

View 2482 ROXBURY ROAD Winter Park, FL MLS# O6406443
$375,000
2

Beds

1.0

Baths

913

Sq.Ft.

2482 ROXBURY ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
$425,000
940

Sq.Ft.

157 E NEW ENGLAND AVENUE 302

Winter Park, FL

Courtesy of SANDRONI HOLDINGS REAL ESTATE LLC

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

376

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

PriceCount
$0 - 100K7
$100K - 200K41
$200K - 300K23
$300K - 400K15
$400K - 500K34
$500K - 600K34
$600K - 700K38
$700K - 800K14
$800K - 900K11
$900K - 1M11
$1M - Max148

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family229
Townhouse22
Condo85
Commercial9
Rental80
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 8/23/2026)

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 8/24/2026.