219 total properties
Did you mean the neighborhood Winter Park?
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 2251 NAIRN DRIVE Winter Park, FL MLS# O6429723
  • Recently Listed
1 of 38
$649,900
4

Beds

2.1

Baths

1,978

Sq.Ft.

2251 NAIRN DRIVE

Winter Park, FL

View 1695 LEE ROAD A101 Winter Park, FL MLS# O6429942
  • Recently Listed with Virtual Tour
1 of 22
$154,900
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD A101

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 351 STARLING ROAD Winter Park, FL MLS# O6429698
  • Recently Listed
1 of 30
$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
  • Recently Listed with 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
  • Recently Listed with Virtual Tour
1 of 7
$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 228 RIPPLING LANE Winter Park, FL MLS# O6429407
  • Recently Listed with Virtual Tour
1 of 55
$540,000
3

Beds

2.0

Baths

1,618

Sq.Ft.

228 RIPPLING LANE

Winter Park, FL

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
  • Recently Listed with Virtual Tour
1 of 18
$444,900
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 433 GILBERT ROAD Winter Park, FL MLS# O6428430
  • Recently Listed with Virtual Tour
1 of 36
$675,000
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
  • Recently Listed with Virtual Tour
1 of 22
$129,000
1

Beds

1.0

Baths

735

Sq.Ft.

1000 S SEMORAN BOULEVARD 305

Winter Park, FL

View 1850 BRYAN AVENUE Winter Park, FL MLS# R4911701
  • Recently Listed with Virtual Tour
1 of 33
$795,000
3

Beds

2.0

Baths

1,563

Sq.Ft.

1850 BRYAN AVENUE

Winter Park, FL

Courtesy of CENTRAL FLORIDA REAL ESTATE CE
View 2833 PRINCE JOHN ROAD Winter Park, FL MLS# O6427246
  • Recently Listed with Virtual Tour
1 of 31
$684,000
4

Beds

2.0

Baths

1,605

Sq.Ft.

2833 PRINCE JOHN ROAD

Winter Park, FL

View 200 SAINT ANDREWS BOULEVARD 2904 Winter Park, FL MLS# O6427536
  • Recently Listed with Virtual Tour
1 of 21
$230,000
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2904

Winter Park, FL

View 230 STRATHY LANE Winter Park, FL MLS# O6426909
  • Recently Listed
1 of 2
$499,000
920

Sq.Ft.

230 STRATHY LANE

Winter Park, FL

View 2231 NAIRN DRIVE Winter Park, FL MLS# O6426997
  • Recently Listed
1 of 2
$499,000
1,088

Sq.Ft.

2231 NAIRN DRIVE

Winter Park, FL

View 216 BLOSSOM LANE Winter Park, FL MLS# O6426403
  • Virtual Tour
1 of 63
$624,900
4

Beds

2.0

Baths

1,933

Sq.Ft.

216 BLOSSOM LANE

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

355

Estimated median home price

$725,000
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 - 200K40
$200K - 300K22
$300K - 400K15
$400K - 500K33
$500K - 600K25
$600K - 700K32
$700K - 800K15
$800K - 900K12
$900K - 1M10
$1M - Max144

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family215
Townhouse21
Condo79
Commercial10
Rental72
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 8/3/2026)

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 8/3/2026.

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 8/3/2026.