172 total properties
Did you mean the neighborhood Winter Park?
View 630 SAINT DUNSTAN WAY Winter Park, FL MLS# O6376860
$675,000
5

Beds

2.0

Baths

2,240

Sq.Ft.

630 SAINT DUNSTAN WAY

Winter Park, FL

Courtesy of EXP REALTY LLC
View 352 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6375545
$650,000
5

Beds

3.0

Baths

1,917

Sq.Ft.

352 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 352 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6377540
$650,000
5

Beds

3.0

Baths

1,917

Sq.Ft.

352 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1760 GREENWICH AVENUE Winter Park, FL MLS# O6392001
  • Recently Listed with Virtual Tour
1 of 18
$650,000
3

Beds

2.0

Baths

1,610

Sq.Ft.

1760 GREENWICH AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2330 COLDSTREAM DRIVE Winter Park, FL MLS# O6384436
  • Recently Listed with Virtual Tour
1 of 20
$650,000
4

Beds

2.0

Baths

1,750

Sq.Ft.

2330 COLDSTREAM DRIVE

Winter Park, FL

Courtesy of DTB FLORIDA REALTY, INC.
View 1926 NATALEN ROAD Winter Park, FL MLS# O6388308
  • Virtual Tour
1 of 44
$649,900
3

Beds

2.0

Baths

1,469

Sq.Ft.

1926 NATALEN ROAD

Winter Park, FL

Courtesy of JAMIESON PROPERTIES, INC.
View 1523 GOLFSIDE DRIVE Winter Park, FL MLS# O6392204
  • Virtual Tour
1 of 27
$649,000
4

Beds

2.0

Baths

1,936

Sq.Ft.

1523 GOLFSIDE DRIVE

Winter Park, FL

Courtesy of BALDWIN PARK REALTY LLC
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5137596
  • Virtual Tour
1 of 30
$645,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1134 WASHINGTON AVENUE 13 Winter Park, FL MLS# O6362206
$645,000
3

Beds

3.1

Baths

2,083

Sq.Ft.

1134 WASHINGTON AVENUE 13

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5139410
  • Virtual Tour
1 of 37
$645,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1137 OAKS BOULEVARD Winter Park, FL MLS# O6379388
$634,900
2

Beds

1.1

Baths

1,149

Sq.Ft.

1137 OAKS BOULEVARD

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 2708 LION HEART ROAD Winter Park, FL MLS# O6387685
  • Virtual Tour
1 of 47
$634,500
3

Beds

2.0

Baths

1,785

Sq.Ft.

2708 LION HEART ROAD

Winter Park, FL

Courtesy of EQUITYPRO LLC
View 1860 STAUNTON AVENUE Winter Park, FL MLS# O6378461
  • Virtual Tour
1 of 11
$630,000
Studio

Beds

0.0

Baths

1860 STAUNTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 513 CORNWALL ROAD Winter Park, FL MLS# O6372577
$629,000
3

Beds

2.0

Baths

1,735

Sq.Ft.

513 CORNWALL ROAD

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 259 E CANTON AVENUE 259 Winter Park, FL MLS# O6389246
  • Recently Listed with Virtual Tour
1 of 36
$629,000
2

Beds

2.0

Baths

1,040

Sq.Ft.

259 E CANTON AVENUE 259

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 649 BERWICK DRIVE Winter Park, FL MLS# O6388752
  • Recently Listed
1 of 34
$610,000
4

Beds

2.0

Baths

1,943

Sq.Ft.

649 BERWICK DRIVE

Winter Park, FL

Courtesy of MAINFRAME REAL ESTATE
View 1399 ALOMA AVENUE Winter Park, FL MLS# O6304495
  • Virtual Tour
1 of 38
$600,000
3

Beds

2.0

Baths

1,804

Sq.Ft.

1399 ALOMA AVENUE

Winter Park, FL

Courtesy of FLORIDA HOMES REALTY & MORTGAGE
View 218 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6388723
  • Recently Listed with Virtual Tour
1 of 29
$600,000
3

Beds

2.0

Baths

1,618

Sq.Ft.

218 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 1354 INDIANA AVENUE Winter Park, FL MLS# O6387500
  • Virtual Tour
1 of 39
$599,900
3

Beds

2.0

Baths

1,269

Sq.Ft.

1354 INDIANA AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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

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

331

Estimated median home price

$750,000
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 46
$200K - 300K 23
$300K - 400K 14
$400K - 500K 30
$500K - 600K 15
$600K - 700K 23
$700K - 800K 16
$800K - 900K 9
$900K - 1M 9
$1M - Max 142

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 197
Townhouse 17
Condo 85
Commercial 3
Rental 81
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 3/27/2026)

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 3/30/2026.

The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

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 3/30/2026.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include 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 3/30/2026.

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 3/30/2026.