80 total properties
Did you mean the neighborhood Winter Park?
View 1625 TIOGA TRAIL Winter Park, FL MLS# O6431784
  • Recently Listed with Virtual Tour
1 of 46
$4,295
4

Beds

3.0

Baths

2,134

Sq.Ft.

1625 TIOGA TRAIL

Winter Park, FL

Courtesy of SUN PROPERTIES, INC.
View 7446 WYNNEWOOD SQUARE 190 Winter Park, FL MLS# R4911800
  • Recently Listed with Virtual Tour
1 of 22
$1,850
2

Beds

2.1

Baths

1,031

Sq.Ft.

7446 WYNNEWOOD SQUARE 190

Winter Park, FL

View 1695 LEE ROAD E116 Winter Park, FL MLS# O6432102
  • Recently Listed with Virtual Tour
1 of 36
$1,800
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD E116

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 2366 COLDSTREAM DRIVE Winter Park, FL MLS# O6431985
  • Recently Listed with Virtual Tour
1 of 18
$2,595
4

Beds

2.0

Baths

1,409

Sq.Ft.

2366 COLDSTREAM DRIVE

Winter Park, FL

View 1600 INDIANA AVENUE Winter Park, FL MLS# O6431665
  • Recently Listed with Virtual Tour
1 of 5
$1,350
1

Beds

1.0

Baths

620

Sq.Ft.

1600 INDIANA AVENUE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 1303 CANTERBURY ROAD Winter Park, FL MLS# O6431332
$2,750
3

Beds

2.0

Baths

1,030

Sq.Ft.

1303 CANTERBURY ROAD

Winter Park, FL

View 419 WARRENTON ROAD 419 Winter Park, FL MLS# O6430293
$1,850
2

Beds

2.0

Baths

1,043

Sq.Ft.

419 WARRENTON ROAD 419

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 1136 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6430077
$6,000
3

Beds

3.0

Baths

2,434

Sq.Ft.

1136 S PENNSYLVANIA AVENUE

Winter Park, FL

View 1409 MICHIGAN AVENUE Winter Park, FL MLS# O6430070
  • Recently Listed
1 of 18
$3,150
3

Beds

2.1

Baths

1,803

Sq.Ft.

1409 MICHIGAN AVENUE

Winter Park, FL

View 1815 BARKER DRIVE Winter Park, FL MLS# O6429070
$4,000
4

Beds

2.0

Baths

1,548

Sq.Ft.

1815 BARKER DRIVE

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6429868
$3,950
4

Beds

2.0

Baths

1,660

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of EXP REALTY LLC
View 835 W CANTON AVENUE Winter Park, FL MLS# O6429943
$6,300
3

Beds

3.1

Baths

2,415

Sq.Ft.

835 W CANTON AVENUE

Winter Park, FL

View 912 CARVELL DRIVE Winter Park, FL MLS# O6429936
$2,800
3

Beds

2.0

Baths

1,614

Sq.Ft.

912 CARVELL DRIVE

Winter Park, FL

Courtesy of INTOP REALTY LLC
View 616 ELLENDALE DRIVE Winter Park, FL MLS# O6428076
  • Recently Listed with Virtual Tour
1 of 23
$4,000
4

Beds

2.0

Baths

1,405

Sq.Ft.

616 ELLENDALE DRIVE

Winter Park, FL

View 612 TRINIDAD COURT 612 Winter Park, FL MLS# O6429437
$1,750
2

Beds

2.0

Baths

1,037

Sq.Ft.

612 TRINIDAD COURT 612

Winter Park, FL

View 7514 LAUREL SPRINGS DRIVE Winter Park, FL MLS# O6429608
$2,600
4

Beds

2.0

Baths

1,677

Sq.Ft.

7514 LAUREL SPRINGS DRIVE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1434 MINNESOTA AVENUE Winter Park, FL MLS# O6429250
$1,495
2

Beds

1.0

Baths

1,000

Sq.Ft.

1434 MINNESOTA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1368 HIBISCUS AVENUE Winter Park, FL MLS# O6429182
$7,500
4

Beds

2.1

Baths

2,394

Sq.Ft.

1368 HIBISCUS AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 3035 GEORGE MASON AVENUE D20 Winter Park, FL MLS# S5154582
$1,250
1

Beds

1.0

Baths

549

Sq.Ft.

3035 GEORGE MASON AVENUE D20

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1442 PALM AVENUE Winter Park, FL MLS# O6421394
  • Virtual Tour
1 of 33
$9,900
5

Beds

6.0

Baths

2,735

Sq.Ft.

1442 PALM 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

373

Estimated median home price

$695,000
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 - 100K7
$100K - 200K41
$200K - 300K23
$300K - 400K15
$400K - 500K32
$500K - 600K34
$600K - 700K38
$700K - 800K14
$800K - 900K11
$900K - 1M11
$1M - Max147

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family226
Townhouse22
Condo85
Commercial9
Rental80
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 8/22/2026)

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 8/22/2026.