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 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 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

The time to sell is now! THE TIME TO SELL IS NOW!
View 333 CORNWALL ROAD Winter Park, FL MLS# O6429868
$3,650
4

Beds

2.0

Baths

1,660

Sq.Ft.

333 CORNWALL ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 677 SELKIRK DRIVE Winter Park, FL MLS# O6433867
$3,650
3

Beds

2.0

Baths

2,183

Sq.Ft.

677 SELKIRK DRIVE

Winter Park, FL

View 7864 BROKEN ARROW TRAIL Winter Park, FL MLS# O6406209
$3,200
4

Beds

2.1

Baths

2,219

Sq.Ft.

7864 BROKEN ARROW TRAIL

Winter Park, FL

View 1830 STAUNTON AVENUE Winter Park, FL MLS# O6424087
  • Adult Community with Virtual Tour
1 of 14
$3,200
3

Beds

2.1

Baths

1,774

Sq.Ft.

1830 STAUNTON AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1409 MICHIGAN AVENUE Winter Park, FL MLS# O6430070
$3,150
3

Beds

2.1

Baths

1,803

Sq.Ft.

1409 MICHIGAN AVENUE

Winter Park, FL

View 2401 ALBERT LEE PARKWAY Winter Park, FL MLS# O6428494
$3,050
3

Beds

2.0

Baths

1,450

Sq.Ft.

2401 ALBERT LEE PARKWAY

Winter Park, FL

View 1816 MIZELL AVENUE Winter Park, FL MLS# O6433140
$3,000
3

Beds

1.0

Baths

1,732

Sq.Ft.

1816 MIZELL 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 1627 ORANGE AVENUE Winter Park, FL MLS# O6424429
$2,750
3

Beds

2.0

Baths

1,302

Sq.Ft.

1627 ORANGE AVENUE

Winter Park, FL

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 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6421961
$2,695
2

Beds

2.1

Baths

1,428

Sq.Ft.

630 KILLARNEY BAY COURT 3

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 2530 PASSAMONTE DRIVE 10E Winter Park, FL MLS# O6400096
$2,600
3

Beds

2.1

Baths

1,837

Sq.Ft.

2530 PASSAMONTE DRIVE 10E

Winter Park, FL

Courtesy of EXP REALTY LLC
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 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 Address not provided Winter Park, FL MLS# O6435262
$2,500
Studio

Beds

0.0

Baths

Address not provided

Winter Park, FL

View 887 EASTBROOK BOULEVARD Winter Park, FL MLS# O6420055
$2,450
4

Beds

2.0

Baths

1,701

Sq.Ft.

887 EASTBROOK BOULEVARD

Winter Park, FL

View 521 OHIO STREET Winter Park, FL MLS# O6421429
  • Virtual Tour
1 of 25
$2,400
3

Beds

2.5

Baths

1,852

Sq.Ft.

521 OHIO STREET

Winter Park, FL

Courtesy of RE/MAX CENTRAL REALTY

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 8/23/2026.