185 total properties
Did you mean the neighborhood Winter Park?
View 2015 TAYLOR AVENUE Winter Park, FL MLS# O6436061
$430,000
3

Beds

2.0

Baths

1,439

Sq.Ft.

2015 TAYLOR AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 283 SANDLEWOOD TRAIL 3 Winter Park, FL MLS# O6431475
$285,000
2

Beds

2.1

Baths

960

Sq.Ft.

283 SANDLEWOOD TRAIL 3

Winter Park, FL

Courtesy of RE/MAX INNOVATION
View 4033 TENITA DRIVE Winter Park, FL MLS# O6424621
$569,000
4

Beds

2.0

Baths

2,022

Sq.Ft.

4033 TENITA DRIVE

Winter Park, FL

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 1695 LEE ROAD D107 Winter Park, FL MLS# O6425124
$180,000
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD D107

Winter Park, FL

Courtesy of PRIMESTATE REALTY, INC.
View 1333 S DENNING DRIVE Winter Park, FL MLS# O6431370
$299,000
2

Beds

1.0

Baths

702

Sq.Ft.

1333 S DENNING DRIVE

Winter Park, FL

View 7413 BELLE RIVER COURT 3 Winter Park, FL MLS# O6430667
$219,900
3

Beds

2.1

Baths

1,151

Sq.Ft.

7413 BELLE RIVER COURT 3

Winter Park, FL

View 4026 TENITA DRIVE Winter Park, FL MLS# O6430278
$599,000
3

Beds

2.0

Baths

2,031

Sq.Ft.

4026 TENITA DRIVE

Winter Park, FL

View 531 W SWOOPE AVENUE Winter Park, FL MLS# O6430119
$635,000
2

Beds

2.0

Baths

1,188

Sq.Ft.

531 W SWOOPE AVENUE

Winter Park, FL

View 669 W COMSTOCK AVENUE Winter Park, FL MLS# TB8535201
$249,000
Studio

Beds

0.0

Baths

669 W COMSTOCK AVENUE

Winter Park, FL

View 1695 LEE ROAD A101 Winter Park, FL MLS# O6429942
$154,900
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD A101

Winter Park, FL

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 1871 BRYAN AVENUE Winter Park, FL MLS# O6424945
$625,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

1871 BRYAN AVENUE

Winter Park, FL

View 1071 ARAGON AVENUE Winter Park, FL MLS# O6429215
$575,000
2

Beds

2.1

Baths

1,851

Sq.Ft.

1071 ARAGON AVENUE

Winter Park, FL

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 433 GILBERT ROAD Winter Park, FL MLS# O6428430
  • Virtual Tour
1 of 36
$669,900
3

Beds

2.0

Baths

1,770

Sq.Ft.

433 GILBERT ROAD

Winter Park, FL

View 2826 AMBERGATE ROAD Winter Park, FL MLS# O6427973
$460,000
3

Beds

2.0

Baths

1,521

Sq.Ft.

2826 AMBERGATE ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1000 S SEMORAN BOULEVARD 305 Winter Park, FL MLS# O6428044
$115,000
1

Beds

1.0

Baths

735

Sq.Ft.

1000 S SEMORAN BOULEVARD 305

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

358

Estimated median home price

$705,000
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 - 200K39
$200K - 300K22
$300K - 400K15
$400K - 500K37
$500K - 600K27
$600K - 700K36
$700K - 800K11
$800K - 900K10
$900K - 1M10
$1M - Max148

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family218
Townhouse21
Condo77
Commercial9
Rental78
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 9/5/2026)

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 9/5/2026.