132 total properties
Did you mean the neighborhood Winter Park?
View 1259 INDIANA AVENUE Winter Park, FL MLS# O6434701
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1 of 67
OPEN HOUSE: Sunday 11/1 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
View 151 N ORLANDO AVENUE 242 Winter Park, FL MLS# O6437574
$269,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE 242

Winter Park, FL

Courtesy of COLONIALTOWN REALTY
View 283 SANDLEWOOD TRAIL 3 Winter Park, FL MLS# O6431475
$279,000
2

Beds

2.1

Baths

960

Sq.Ft.

283 SANDLEWOOD TRAIL 3

Winter Park, FL

Courtesy of RE/MAX INNOVATION
The time to sell is now! THE TIME TO SELL IS NOW!
View 2126 ALBERT LEE PARKWAY Winter Park, FL MLS# O6435973
$415,000
3

Beds

2.0

Baths

1,187

Sq.Ft.

2126 ALBERT LEE PARKWAY

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2824 PRINCE JOHN ROAD Winter Park, FL MLS# O6435708
$475,000
2

Beds

2.0

Baths

1,438

Sq.Ft.

2824 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 7525 LODGE POLE TRAIL Winter Park, FL MLS# O6417303
$550,000
4

Beds

2.0

Baths

1,936

Sq.Ft.

7525 LODGE POLE TRAIL

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 623 GRENADINE COURT 623 Winter Park, FL MLS# O6434195
$194,900
2

Beds

2.0

Baths

1,037

Sq.Ft.

623 GRENADINE COURT 623

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2641 CARVELL COURT Winter Park, FL MLS# O6430894
$525,000
4

Beds

2.0

Baths

2,126

Sq.Ft.

2641 CARVELL COURT

Winter Park, FL

Courtesy of CHAMBERLAIN REALTY LLC
View 2183 CRANDON AVENUE Winter Park, FL MLS# O6433521
$469,000
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
$184,900
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
$429,000
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
$242,500
2

Beds

2.0

Baths

913

Sq.Ft.

1250 S DENNING DR Unit 233

Winter Park, FL

Courtesy of STOCKWORTH REALTY GROUP
View 2627 AMBERGATE ROAD Winter Park, FL MLS# O6433352
$530,000
4

Beds

3.0

Baths

1,745

Sq.Ft.

2627 AMBERGATE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1955 ELAND AVENUE Winter Park, FL MLS# O6433345
$405,000
3

Beds

2.0

Baths

1,494

Sq.Ft.

1955 ELAND AVENUE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 1695 LEE ROAD D107 Winter Park, FL MLS# O6425124
$180,000
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD D107

Winter Park, FL

Courtesy of PRIMESTATE REALTY, INC.
View 7413 BELLE RIVER COURT 3 Winter Park, FL MLS# O6430667
$214,900
3

Beds

2.1

Baths

1,151

Sq.Ft.

7413 BELLE RIVER COURT 3

Winter Park, FL

Courtesy of OUTLET REALTY
View 4026 TENITA DRIVE Winter Park, FL MLS# O6430278
$599,000
3

Beds

2.0

Baths

2,031

Sq.Ft.

4026 TENITA DRIVE

Winter Park, FL

Courtesy of RUBY DAVIS, BROKER
View 669 W COMSTOCK AVENUE Winter Park, FL MLS# TB8535201
$210,000
0.0

Baths

669 W COMSTOCK AVENUE

Winter Park, FL

Courtesy of HOMECOIN.COM
View 351 STARLING ROAD Winter Park, FL MLS# O6429698
$499,900
3

Beds

1.1

Baths

1,979

Sq.Ft.

351 STARLING ROAD

Winter Park, FL

Courtesy of HOUWZER INC
View 1000 S SEMORAN BOULEVARD 302 Winter Park, FL MLS# O6428713
$97,000
1

Beds

1.0

Baths

796

Sq.Ft.

1000 S SEMORAN BOULEVARD 302

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III

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

363

Estimated median home price

$825,000
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

PriceCount
$0 - 100K3
$100K - 200K35
$200K - 300K21
$300K - 400K15
$400K - 500K31
$500K - 600K26
$600K - 700K33
$700K - 800K16
$800K - 900K17
$900K - 1M13
$1M - Max153

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family217
Townhouse23
Condo78
Commercial15
Rental90
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 10/31/2026)

Information deemed reliable but not guaranteed.

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 11/1/2026.