311 total properties
Did you mean the neighborhood Winter Park?
View 2040 RANDALL CIRCLE Winter Park, FL MLS# O6386920
  • Recently Listed with Virtual Tour
1 of 39
$3,450,000
5

Beds

4.2

Baths

4,636

Sq.Ft.

2040 RANDALL CIRCLE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1354 INDIANA AVENUE Winter Park, FL MLS# O6387500
  • Recently Listed with 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 610 ELLENDALE DRIVE Winter Park, FL MLS# O6388157
  • Recently Listed with Virtual Tour
1 of 31
$400,000
4

Beds

3.0

Baths

1,359

Sq.Ft.

610 ELLENDALE DRIVE

Winter Park, FL

Courtesy of 4 ACRE REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 958 HANOVER AVENUE Winter Park, FL MLS# O6388088
  • Recently Listed with Virtual Tour
1 of 34
$490,000
4

Beds

3.0

Baths

1,378

Sq.Ft.

958 HANOVER AVENUE

Winter Park, FL

Courtesy of AGILE GROUP REALTY
View 2814 SHERIFF WAY Winter Park, FL MLS# O6383098
  • Recently Listed with Virtual Tour
1 of 48
OPEN HOUSE: Sunday 3/8 1:00 PM - 3:00 PM
$574,900
4

Beds

2.0

Baths

1,948

Sq.Ft.

2814 SHERIFF WAY

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 2708 LION HEART ROAD Winter Park, FL MLS# O6387685
  • Recently Listed with Virtual Tour
1 of 50
$635,000
3

Beds

2.0

Baths

1,785

Sq.Ft.

2708 LION HEART ROAD

Winter Park, FL

Courtesy of EQUITYPRO LLC
View 2501 WINTER PARK ROAD Winter Park, FL MLS# O6384756
  • Recently Listed
1 of 60
OPEN HOUSE: Friday 3/6 2:00 PM - 4:00 PM
$1,795,000
5

Beds

3.1

Baths

3,304

Sq.Ft.

2501 WINTER PARK ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 611 WILLIAMS DRIVE Winter Park, FL MLS# O6387016
  • Recently Listed with Virtual Tour
1 of 46
OPEN HOUSE: Friday 3/6 3:00 PM - 6:00 PM
$2,995,000
5

Beds

4.1

Baths

4,686

Sq.Ft.

611 WILLIAMS DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1260 ALABAMA DRIVE Winter Park, FL MLS# O6387200
  • Recently Listed
1 of 58
OPEN HOUSE: Saturday 3/7 1:00 PM - 3:00 PM
$6,900,000
6

Beds

5.2

Baths

6,396

Sq.Ft.

1260 ALABAMA DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1760 ALABAMA DRIVE Winter Park, FL MLS# O6386409
  • Recently Listed with Virtual Tour
1 of 50
$2,498,000
4

Beds

2.1

Baths

2,841

Sq.Ft.

1760 ALABAMA DRIVE

Winter Park, FL

Courtesy of DAILLAND REAL ESTATE
View 3227 CROWN JEWEL COURT Winter Park, FL MLS# W7883548
  • Recently Listed with Virtual Tour
1 of 28
$329,900
3

Beds

2.1

Baths

1,430

Sq.Ft.

3227 CROWN JEWEL COURT

Winter Park, FL

Courtesy of 1% LISTS CENTRAL FLORIDA
View 628 DUNBLANE DRIVE Winter Park, FL MLS# O6387091
  • Recently Listed with Virtual Tour
1 of 54
OPEN HOUSE: Saturday 3/7 11:00 AM - 3:00 PM
$849,000
3

Beds

2.1

Baths

2,114

Sq.Ft.

628 DUNBLANE DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 629 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6386610
  • Recently Listed with Virtual Tour
1 of 46
$1,695,000
4

Beds

3.1

Baths

3,031

Sq.Ft.

629 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of CLASSIC HOMES
View 2625 SUMMERFIELD ROAD Winter Park, FL MLS# O6384757
  • Recently Listed
1 of 47
OPEN HOUSE: Saturday 3/7 2:00 PM - 4:00 PM
$724,900
5

Beds

3.0

Baths

2,199

Sq.Ft.

2625 SUMMERFIELD ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1016 HOWELL BRANCH ROAD Winter Park, FL MLS# O6386288
  • Recently Listed with Virtual Tour
1 of 64
$1,749,000
4

Beds

3.0

Baths

3,142

Sq.Ft.

1016 HOWELL BRANCH ROAD

Winter Park, FL

Courtesy of PLAID PROPERTIES, LLC
View 1108 FAIRWAY DRIVE Winter Park, FL MLS# O6386266
  • Recently Listed with Virtual Tour
1 of 46
OPEN HOUSE: Saturday 3/7 2:00 PM - 4:00 PM
$725,000
3

Beds

2.0

Baths

1,677

Sq.Ft.

1108 FAIRWAY DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 7336 FOREST HILL COURT 240 Winter Park, FL MLS# O6386461
  • Recently Listed with Virtual Tour
1 of 23
OPEN HOUSE: Sunday 3/8 11:00 AM - 2:00 PM
$184,900
2

Beds

1.1

Baths

990

Sq.Ft.

7336 FOREST HILL COURT 240

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 456 CAROLINA AVENUE Winter Park, FL MLS# O6385625
  • Recently Listed with Virtual Tour
1 of 46
OPEN HOUSE: Saturday 3/7 12:00 PM - 3:00 PM
$1,010,000
3

Beds

3.0

Baths

1,615

Sq.Ft.

456 CAROLINA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1405 MILLER AVENUE Winter Park, FL MLS# O6386405
  • Recently Listed with Virtual Tour
1 of 46
$950,000
3

Beds

2.1

Baths

1,884

Sq.Ft.

1405 MILLER AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2500 LEE ROAD 122 Winter Park, FL MLS# O6384082
  • Recently Listed with Virtual Tour
1 of 25
$189,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 122

Winter Park, FL

Courtesy of PINEAPPLE PLACE REALTY, 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

306

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

Price Count
$0 - 100K 5
$100K - 200K 38
$200K - 300K 30
$300K - 400K 19
$400K - 500K 23
$500K - 600K 16
$600K - 700K 17
$700K - 800K 21
$800K - 900K 6
$900K - 1M 8
$1M - Max 123

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 174
Townhouse 14
Condo 83
Commercial 4
Rental 77
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 5
Mobile Home 0
Farms 0

(Data as of 3/5/2026)

Information deemed reliable but not guaranteed.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

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 3/6/2026.

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 3/6/2026.

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 3/6/2026.

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 3/6/2026.