176 total properties
Did you mean the neighborhood Winter Park?
View 3302 ROYAL STREET Winter Park, FL MLS# O6437344
  • Recently Listed with Virtual Tour
1 of 17
$289,900
3

Beds

2.0

Baths

1,197

Sq.Ft.

3302 ROYAL STREET

Winter Park, FL

View 151 N ORLANDO AVENUE 242 Winter Park, FL MLS# O6437574
  • Recently Listed with Virtual Tour
1 of 25
$269,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE 242

Winter Park, FL

View 1259 INDIANA AVENUE Winter Park, FL MLS# O6434701
  • Recently Listed
1 of 1
OPEN HOUSE: Sunday 8/30 1:00 PM - 4:00 PM
$575,000
2

Beds

2.1

Baths

1,648

Sq.Ft.

1259 INDIANA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 2126 ALBERT LEE PARKWAY Winter Park, FL MLS# O6435973
  • Recently Listed with Virtual Tour
1 of 39
$425,000
3

Beds

2.0

Baths

1,187

Sq.Ft.

2126 ALBERT LEE PARKWAY

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1941 OGLESBY AVENUE Winter Park, FL MLS# N6145448
  • Recently Listed with Virtual Tour
1 of 30
$340,000
2

Beds

1.0

Baths

780

Sq.Ft.

1941 OGLESBY AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 2824 PRINCE JOHN ROAD Winter Park, FL MLS# O6435708
  • Recently Listed with Virtual Tour
1 of 28
OPEN HOUSE: Sunday 8/30 12:00 PM - 3:00 PM
$475,000
2

Beds

2.0

Baths

1,438

Sq.Ft.

2824 PRINCE JOHN ROAD

Winter Park, FL

View 151 N ORLANDO AVENUE 261 Winter Park, FL MLS# O6435092
  • Recently Listed with Virtual Tour
1 of 26
$239,999
1

Beds

1.0

Baths

582

Sq.Ft.

151 N ORLANDO AVENUE 261

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 1313 S DENNING DRIVE Winter Park, FL MLS# O6435470
  • Recently Listed with Virtual Tour
1 of 34
$589,900
3

Beds

2.0

Baths

1,700

Sq.Ft.

1313 S DENNING DRIVE

Winter Park, FL

View 3019 ANTIQUE OAKS CIRCLE 127 Winter Park, FL MLS# O6434819
$144,999
1

Beds

1.0

Baths

749

Sq.Ft.

3019 ANTIQUE OAKS CIRCLE 127

Winter Park, FL

View 565 HUNTINGTON AVENUE 565 Winter Park, FL MLS# O6434796
  • Recently Listed with Virtual Tour
1 of 27
OPEN HOUSE: Sunday 8/30 2:00 PM - 4:00 PM
$635,000
3

Beds

2.1

Baths

2,015

Sq.Ft.

565 HUNTINGTON AVENUE 565

Winter Park, FL

View 2765 ABBEY ROAD Winter Park, FL MLS# O6434420
$430,000
3

Beds

2.0

Baths

1,620

Sq.Ft.

2765 ABBEY ROAD

Winter Park, FL

View 623 GRENADINE COURT 623 Winter Park, FL MLS# O6434195
  • Recently Listed with Virtual Tour
1 of 36
$199,900
2

Beds

2.0

Baths

1,037

Sq.Ft.

623 GRENADINE COURT 623

Winter Park, FL

View 1409 SUNSET DRIVE Winter Park, FL MLS# O6433393
  • Recently Listed with Virtual Tour
1 of 33
$649,000
2

Beds

1.1

Baths

1,107

Sq.Ft.

1409 SUNSET DRIVE

Winter Park, FL

View 2183 CRANDON AVENUE Winter Park, FL MLS# O6433521
  • Recently Listed
1 of 28
$499,000
4

Beds

2.0

Baths

1,200

Sq.Ft.

2183 CRANDON AVENUE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 7468 CANFORD COURT 24 Winter Park, FL MLS# O6433680
  • Recently Listed with Virtual Tour
1 of 32
$189,900
2

Beds

1.1

Baths

1,365

Sq.Ft.

7468 CANFORD COURT 24

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 1652 BERKSHIRE AVENUE Winter Park, FL MLS# O6432617
  • Recently Listed with Virtual Tour
1 of 29
$499,000
3

Beds

2.0

Baths

1,498

Sq.Ft.

1652 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1250 S DENNING DR Unit 233 Winter Park, FL MLS# O6430611
  • Recently Listed with Virtual Tour
1 of 31
$245,000
2

Beds

2.0

Baths

913

Sq.Ft.

1250 S DENNING DR Unit 233

Winter Park, FL

View 2627 AMBERGATE ROAD Winter Park, FL MLS# O6433352
  • Recently Listed with Virtual Tour
1 of 16
$575,000
4

Beds

3.0

Baths

1,745

Sq.Ft.

2627 AMBERGATE ROAD

Winter Park, FL

View 1955 ELAND AVENUE Winter Park, FL MLS# O6433345
  • Recently Listed with Virtual Tour
1 of 19
$425,000
3

Beds

2.0

Baths

1,494

Sq.Ft.

1955 ELAND AVENUE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 2641 CARVELL COURT Winter Park, FL MLS# O6430894
  • Recently Listed with Virtual Tour
1 of 38
$575,000
4

Beds

2.0

Baths

2,126

Sq.Ft.

2641 CARVELL COURT

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

380

Estimated median home price

$697,250
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

PriceCount
$0 - 100K4
$100K - 200K42
$200K - 300K23
$300K - 400K13
$400K - 500K39
$500K - 600K32
$600K - 700K39
$700K - 800K12
$800K - 900K11
$900K - 1M11
$1M - Max154

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family232
Townhouse23
Condo81
Commercial9
Rental79
Lots and Land25
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 8/30/2026)

Information deemed reliable but not guaranteed.

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 8/30/2026.