256 total properties
Did you mean the neighborhood Winter Park?
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
  • Virtual Tour
1 of 52
$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

The time to sell is now! THE TIME TO SELL IS NOW!
View 281 BREWER AVENUE Winter Park, FL MLS# O6424364
  • Recently Listed with Virtual Tour
1 of 54
$1,800,000
5

Beds

4.1

Baths

4,029

Sq.Ft.

281 BREWER AVENUE

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 436 W SWOOPE AVENUE Winter Park, FL MLS# O6423105
  • Recently Listed with Virtual Tour
1 of 59
$719,900
4

Beds

3.1

Baths

2,602

Sq.Ft.

436 W SWOOPE AVENUE

Winter Park, FL

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 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

View 708 BALMORAL ROAD Winter Park, FL MLS# O6423883
$1,690,000
4

Beds

3.0

Baths

2,786

Sq.Ft.

708 BALMORAL ROAD

Winter Park, FL

View 2803 RIDDLE DRIVE Winter Park, FL MLS# O6423829
  • Recently Listed
1 of 28
OPEN HOUSE: Sunday 7/26 1:00 PM - 2:00 PM
$569,000
3

Beds

2.1

Baths

1,709

Sq.Ft.

2803 RIDDLE DRIVE

Winter Park, FL

View 885 CARNATION DRIVE Winter Park, FL MLS# S5153456
  • Recently Listed with Virtual Tour
1 of 38
$375,000
4

Beds

2.0

Baths

1,240

Sq.Ft.

885 CARNATION DRIVE

Winter Park, FL

View 3360 ROYAL STREET Winter Park, FL MLS# O6423106
$179,900
2

Beds

2.0

Baths

981

Sq.Ft.

3360 ROYAL STREET

Winter Park, FL

View 1310 FAIRVIEW AVENUE Winter Park, FL MLS# O6424108
  • Recently Listed with Virtual Tour
1 of 14
$925,000
4

Beds

2.1

Baths

2,552

Sq.Ft.

1310 FAIRVIEW AVENUE

Winter Park, FL

Courtesy of FLORIDA PROPERTY SPECIALIST
View 2824 WOODSIDE AVENUE Winter Park, FL MLS# O6423146
$600,000
2

Beds

2.0

Baths

912

Sq.Ft.

2824 WOODSIDE AVENUE

Winter Park, FL

Courtesy of PARKSIDE PROPERTIES, 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

324

Estimated median home price

$844,000
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 38
$200K - 300K 18
$300K - 400K 15
$400K - 500K 23
$500K - 600K 21
$600K - 700K 26
$700K - 800K 10
$800K - 900K 14
$900K - 1M 8
$1M - Max 144

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 200
Townhouse 17
Condo 72
Commercial 6
Rental 68
Lots and Land 21
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/22/2026)

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 7/22/2026.

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 7/22/2026.