260 total properties
Did you mean the neighborhood Winter Park?
View 2504 FORFARSHIRE DRIVE Winter Park, FL MLS# O6424656
$630,000
3

Beds

2.0

Baths

1,915

Sq.Ft.

2504 FORFARSHIRE DRIVE

Winter Park, FL

Courtesy of RE/MAX CENTRAL REALTY
View 1351 ONECO AVENUE Winter Park, FL MLS# O6425827
  • Recently Listed
1 of 30
OPEN HOUSE: Saturday 7/18 1:00 PM - 3:00 PM
$1,150,000
4

Beds

3.0

Baths

2,474

Sq.Ft.

1351 ONECO AVENUE

Winter Park, FL

View 1562 ARBOR PARK DRIVE Winter Park, FL MLS# O6425628
  • Recently Listed with Virtual Tour
1 of 49
$775,000
4

Beds

2.1

Baths

1,899

Sq.Ft.

1562 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 145 SCOTTSDALE SQUARE Winter Park, FL MLS# O6424788
  • Recently Listed with Virtual Tour
1 of 33
$99,900
2

Beds

2.0

Baths

1,020

Sq.Ft.

145 SCOTTSDALE SQUARE

Winter Park, FL

View 1500 GAY ROAD 4D Winter Park, FL MLS# O6425078
  • Recently Listed with Virtual Tour
1 of 15
$175,000
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 4D

Winter Park, FL

View 1871 BARKER DRIVE Winter Park, FL MLS# O6425831
  • Recently Listed with Virtual Tour
1 of 36
OPEN HOUSE: Saturday 7/18 1:00 PM - 3:00 PM
$779,000
3

Beds

3.0

Baths

2,231

Sq.Ft.

1871 BARKER DRIVE

Winter Park, FL

View 922 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6424685
  • Recently Listed with Virtual Tour
1 of 30
$1,995,000
4

Beds

4.0

Baths

3,440

Sq.Ft.

922 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 462 W LYMAN AVENUE Winter Park, FL MLS# O6423842
  • Recently Listed with Virtual Tour
1 of 25
$1,595,000
3

Beds

2.1

Baths

1,944

Sq.Ft.

462 W LYMAN AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1778 MONDRIAN CIRCLE Winter Park, FL MLS# O6422941
  • Recently Listed with Virtual Tour
1 of 45
$1,339,000
3

Beds

3.1

Baths

2,377

Sq.Ft.

1778 MONDRIAN CIRCLE

Winter Park, FL

View 7450 WYNNEWOOD SQUARE 189 Winter Park, FL MLS# O6425486
  • Recently Listed with Virtual Tour
1 of 41
$185,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7450 WYNNEWOOD SQUARE 189

Winter Park, FL

View 263 SCOTTSDALE SQUARE 263 Winter Park, FL MLS# O6424619
$80,000
2

Beds

2.0

Baths

1,020

Sq.Ft.

263 SCOTTSDALE SQUARE 263

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2526 PASSAMONTE DRIVE 10F Winter Park, FL MLS# O6418710
  • Recently Listed with Virtual Tour
1 of 10
$335,000
3

Beds

2.1

Baths

1,790

Sq.Ft.

2526 PASSAMONTE DRIVE 10F

Winter Park, FL

View 1134 WASHINGTON AVENUE 13C Winter Park, FL MLS# O6416746
$525,000
3

Beds

3.1

Baths

2,195

Sq.Ft.

1134 WASHINGTON AVENUE 13C

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 724 MONMOUTH WAY Winter Park, FL MLS# O6424409
$849,999
5

Beds

3.1

Baths

2,832

Sq.Ft.

724 MONMOUTH WAY

Winter Park, FL

View 2010 SUMMERFIELD ROAD Winter Park, FL MLS# O6420140
  • Recently Listed with Virtual Tour
1 of 40
$594,500
3

Beds

2.0

Baths

1,889

Sq.Ft.

2010 SUMMERFIELD ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 303 SCOTTSDALE SQUARE 303 Winter Park, FL MLS# O6424296
$80,000
2

Beds

2.0

Baths

1,020

Sq.Ft.

303 SCOTTSDALE SQUARE 303

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 313L SYLVAN DRIVE Winter Park, FL MLS# O6424300
  • Recently Listed
1 of 4
$1,750,000
Studio

Beds

0.0

Baths

313L SYLVAN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 4437 GLENMOOR COURT Winter Park, FL MLS# O6424511
  • Recently Listed with Virtual Tour
1 of 37
$539,000
3

Beds

2.0

Baths

2,633

Sq.Ft.

4437 GLENMOOR COURT

Winter Park, FL

View 1477 W FAIRBANKS AVENUE Winter Park, FL MLS# O6422964
  • Recently Listed with Virtual Tour
1 of 70
$2,500,000
6,049

Sq.Ft.

1477 W FAIRBANKS AVENUE

Winter Park, FL

View 4965 ORANGE AVENUE Winter Park, FL MLS# O6423739
  • Recently Listed with Virtual Tour
1 of 29
$379,900
4

Beds

2.0

Baths

1,444

Sq.Ft.

4965 ORANGE AVENUE

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

303

Estimated median home price

$799,000
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 7
$100K - 200K 39
$200K - 300K 16
$300K - 400K 14
$400K - 500K 22
$500K - 600K 22
$600K - 700K 22
$700K - 800K 10
$800K - 900K 11
$900K - 1M 7
$1M - Max 133

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 185
Townhouse 13
Condo 72
Commercial 7
Rental 67
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/16/2026)

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 7/17/2026.

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.

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 7/17/2026.