206 total properties
Did you mean the neighborhood Winter Park?
View 2889 ROUEN AVENUE Winter Park, FL MLS# L4961275
$399,500
3

Beds

2.0

Baths

1,144

Sq.Ft.

2889 ROUEN AVENUE

Winter Park, FL

Courtesy of HELLOSOLD LLC
View 3651 N GOLDENROD ROAD D102 Winter Park, FL MLS# O6401114
$160,000
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD D102

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1261 INDIANA AVENUE Winter Park, FL MLS# O6400698
  • Virtual Tour
1 of 29
OPEN HOUSE: Saturday 5/30 1:00 PM - 3:00 PM
$539,000
3

Beds

2.1

Baths

1,660

Sq.Ft.

1261 INDIANA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
View 1307 FORMOSA AVENUE Winter Park, FL MLS# O6400711
  • Virtual Tour
1 of 33
$373,800
2

Beds

1.0

Baths

1,150

Sq.Ft.

1307 FORMOSA AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 1010 GARDEN DRIVE Winter Park, FL MLS# O6400287
  • Virtual Tour
1 of 37
$485,000
Studio

Beds

0.0

Baths

1010 GARDEN DRIVE

Winter Park, FL

Courtesy of WATSON REALTY CORP.
View 1319 BESSMOR ROAD Winter Park, FL MLS# O6400395
  • Virtual Tour
1 of 13
$595,000
3

Beds

2.0

Baths

1,126

Sq.Ft.

1319 BESSMOR ROAD

Winter Park, FL

Courtesy of GALLOWAY REAL ESTATE
View 814 DENSMORE DR Winter Park, FL MLS# O6399773
  • Virtual Tour
1 of 24
$425,000
4

Beds

2.0

Baths

1,610

Sq.Ft.

814 DENSMORE DR

Winter Park, FL

Courtesy of ORANGE SLICE PROPERTIES
View 1741 WESTCHESTER AVENUE Winter Park, FL MLS# O6399014
$595,000
3

Beds

2.0

Baths

1,434

Sq.Ft.

1741 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 811 OVERSPIN DRIVE Winter Park, FL MLS# O6400009
  • Virtual Tour
1 of 9
$349,000
2

Beds

1.0

Baths

749

Sq.Ft.

811 OVERSPIN DRIVE

Winter Park, FL

Courtesy of RICK SINGH REAL ESTATE
View 1830 EDWIN BOULEVARD Winter Park, FL MLS# O6400055
  • Virtual Tour
1 of 52
OPEN HOUSE: Friday 5/29 3:00 PM - 5:00 PM
$649,800
3

Beds

2.0

Baths

1,287

Sq.Ft.

1830 EDWIN BOULEVARD

Winter Park, FL

Courtesy of ZEN LIVING HOMES LLC
View 927 FAIRWAY DRIVE Winter Park, FL MLS# TB8498515
  • Virtual Tour
1 of 29
$680,000
4

Beds

3.0

Baths

1,918

Sq.Ft.

927 FAIRWAY DRIVE

Winter Park, FL

Courtesy of FLAT FEE MLS REALTY
View 3028 GEORGE MASON AVENUE J-7E Winter Park, FL MLS# O6398380
$105,000
2

Beds

2.0

Baths

1,088

Sq.Ft.

3028 GEORGE MASON AVENUE J-7E

Winter Park, FL

Courtesy of EXP REALTY LLC
View 3172 CROWN JEWEL COURT Winter Park, FL MLS# O6397498
$339,900
3

Beds

2.1

Baths

1,406

Sq.Ft.

3172 CROWN JEWEL COURT

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1785 WALNUT AVENUE Winter Park, FL MLS# O6399577
  • Virtual Tour
1 of 35
$825,000
Studio

Beds

0.0

Baths

1785 WALNUT AVENUE

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 7454 WYNNEWOOD SQUARE 188 Winter Park, FL MLS# O6386578
  • Adult Community with Virtual Tour
1 of 29
$229,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

7454 WYNNEWOOD SQUARE 188

Winter Park, FL

Courtesy of APPLE REALTY
View 7429 DANIEL WEBSTER DRIVE 14 (#C) Winter Park, FL MLS# O6400425
$133,000
2

Beds

2.0

Baths

1,036

Sq.Ft.

7429 DANIEL WEBSTER DRIVE 14 (#C)

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 2756 SHERIFF WAY Winter Park, FL MLS# O6402570
  • Recently Listed with Virtual Tour
1 of 48
$625,000
3

Beds

2.0

Baths

1,812

Sq.Ft.

2756 SHERIFF WAY

Winter Park, FL

Courtesy of PALM CIRCLE REALTY
View 1701 GOODRICH AVENUE Winter Park, FL MLS# O6400278
$739,000
3

Beds

2.0

Baths

1,528

Sq.Ft.

1701 GOODRICH AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1618 INDIANA AVENUE Winter Park, FL MLS# O6398673
  • Virtual Tour
1 of 31
$675,000
4

Beds

2.0

Baths

1,604

Sq.Ft.

1618 INDIANA AVENUE

Winter Park, FL

Courtesy of NATIONAL REAL ESTATE
View 3054 BLUEBROOK DRIVE Winter Park, FL MLS# O6398450
  • Virtual Tour
1 of 27
$410,000
3

Beds

2.0

Baths

1,939

Sq.Ft.

3054 BLUEBROOK DRIVE

Winter Park, FL

Courtesy of WEATHERSPOON REALTY INC

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

395

Estimated median home price

$789,000
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 2
$100K - 200K 46
$200K - 300K 24
$300K - 400K 25
$400K - 500K 29
$500K - 600K 23
$600K - 700K 30
$700K - 800K 21
$800K - 900K 15
$900K - 1M 10
$1M - Max 170

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 254
Townhouse 15
Condo 85
Commercial 7
Rental 80
Lots and Land 28
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/28/2026)

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 5/28/2026.

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 5/28/2026.

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 5/28/2026.

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 5/28/2026.