73 total properties
Did you mean the neighborhood Winter Park?
View 344 STARLING ROAD Winter Park, FL MLS# O6424771
  • Recently Listed
1 of 43
$4,500
3

Beds

3.0

Baths

1,345

Sq.Ft.

344 STARLING ROAD

Winter Park, FL

View 648 FITZWALTER DRIVE Winter Park, FL MLS# O6421916
  • Recently Listed with Virtual Tour
1 of 27
$4,400
3

Beds

2.0

Baths

1,554

Sq.Ft.

648 FITZWALTER DRIVE

Winter Park, FL

View 1815 BARKER DRIVE Winter Park, FL MLS# O6429070
  • Recently Listed with Virtual Tour
1 of 88
$4,000
4

Beds

2.0

Baths

1,548

Sq.Ft.

1815 BARKER DRIVE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View Address not provided Winter Park, FL MLS# O6429868
  • Recently Listed
1 of 40
$3,950
4

Beds

2.0

Baths

1,660

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of EXP REALTY LLC
View 438 LAKEVIEW AVENUE Winter Park, FL MLS# O6396001
$3,200
2

Beds

1.0

Baths

1,250

Sq.Ft.

438 LAKEVIEW AVENUE

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 2401 ALBERT LEE PARKWAY Winter Park, FL MLS# O6428494
$3,150
3

Beds

2.0

Baths

1,450

Sq.Ft.

2401 ALBERT LEE PARKWAY

Winter Park, FL

View 2251 NAIRN DRIVE Winter Park, FL MLS# O6422217
  • Virtual Tour
1 of 34
$3,100
4

Beds

2.1

Baths

1,978

Sq.Ft.

2251 NAIRN DRIVE

Winter Park, FL

View 540 W COMSTOCK AVENUE Winter Park, FL MLS# GC538622
$2,900
3

Beds

1.0

Baths

1,056

Sq.Ft.

540 W COMSTOCK AVENUE

Winter Park, FL

View 508 DUNBLANE DRIVE Winter Park, FL MLS# O6423719
$2,900
3

Beds

2.0

Baths

1,600

Sq.Ft.

508 DUNBLANE DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 912 CARVELL DRIVE Winter Park, FL MLS# O6429936
  • Recently Listed with Virtual Tour
1 of 22
$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
  • Recently Listed with Virtual Tour
1 of 36
$2,750
3

Beds

2.0

Baths

1,302

Sq.Ft.

1627 ORANGE AVENUE

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

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

View 151 N ORLANDO AVENUE 238 Winter Park, FL MLS# O6415735
$2,600
2

Beds

1.0

Baths

768

Sq.Ft.

151 N ORLANDO AVENUE 238

Winter Park, FL

View 7514 LAUREL SPRINGS DRIVE Winter Park, FL MLS# O6429608
  • Recently Listed with Virtual Tour
1 of 37
$2,600
4

Beds

2.0

Baths

1,677

Sq.Ft.

7514 LAUREL SPRINGS DRIVE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 521 OHIO STREET Winter Park, FL MLS# O6421429
  • Virtual Tour
1 of 25
$2,500
3

Beds

3.0

Baths

1,852

Sq.Ft.

521 OHIO STREET

Winter Park, FL

Courtesy of RE/MAX CENTRAL REALTY
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 150 KILLARNEY BAY COURT 5-5 Winter Park, FL MLS# O6421106
$2,450
2

Beds

2.0

Baths

1,140

Sq.Ft.

150 KILLARNEY BAY COURT 5-5

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

355

Estimated median home price

$725,000
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 - 200K40
$200K - 300K22
$300K - 400K15
$400K - 500K33
$500K - 600K25
$600K - 700K32
$700K - 800K15
$800K - 900K12
$900K - 1M10
$1M - Max144

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family215
Townhouse21
Condo79
Commercial10
Rental72
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 8/3/2026)

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 8/3/2026.