66 total properties
Did you mean the neighborhood Winter Park?
View 330 W MORSE BLVD 104 Winter Park, FL MLS# O6416951
$93,080
1,790

Sq.Ft.

330 W MORSE BLVD 104

Winter Park, FL

View 687 HAROLD AVENUE Winter Park, FL MLS# O6387921
  • New Construction
1 of 3
$84,000
4,500

Sq.Ft.

687 HAROLD AVENUE

Winter Park, FL

View 1501 W FAIRBANKS AVENUE Winter Park, FL MLS# O6419718
  • Recently Listed with Virtual Tour
1 of 8
$72,000
1,649

Sq.Ft.

1501 W FAIRBANKS AVENUE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 2035 GLENWOOD DRIVE Winter Park, FL MLS# O6403420
$47,400
3,718

Sq.Ft.

2035 GLENWOOD DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3029 FORSYTH ROAD Winter Park, FL MLS# O6348919
$42,000
1,500

Sq.Ft.

3029 FORSYTH ROAD

Winter Park, FL

Courtesy of C BRENNER INC
View 663 HAROLD AVENUE Winter Park, FL MLS# O6387903
$42,000
10,429

Sq.Ft.

663 HAROLD AVENUE

Winter Park, FL

View 7307 SANDSCOVE COURT 5 Winter Park, FL MLS# O6392725
$37,800
23,760

Sq.Ft.

7307 SANDSCOVE COURT 5

Winter Park, FL

Courtesy of FUSILIER MANAGEMENT GROUP
View 2306 LEE ROAD Winter Park, FL MLS# O6390092
  • Virtual Tour
1 of 7
$29,150
550

Sq.Ft.

2306 LEE ROAD

Winter Park, FL

Courtesy of CENTURY 21 CARIOTI
View 1814 BARKER DRIVE Winter Park, FL MLS# O6395037
$10,000
5

Beds

4.0

Baths

4,200

Sq.Ft.

1814 BARKER DRIVE

Winter Park, FL

View 660 OSCEOLA AVENUE 101 Winter Park, FL MLS# O6420593
  • Recently Listed with Virtual Tour
1 of 27
$9,500
3

Beds

3.1

Baths

2,714

Sq.Ft.

660 OSCEOLA AVENUE 101

Winter Park, FL

View 2234 HOWARD DRIVE Winter Park, FL MLS# O6427633
  • Recently Listed with Virtual Tour
1 of 25
$8,295
4

Beds

5.1

Baths

3,295

Sq.Ft.

2234 HOWARD DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 527 LANGHOLM DRIVE Winter Park, FL MLS# O6387427
$6,750
4

Beds

3.1

Baths

3,276

Sq.Ft.

527 LANGHOLM DRIVE

Winter Park, FL

Courtesy of WOODRUFF REALTY, INC.
View 2075 JEWELL AVENUE Winter Park, FL MLS# O6386721
$6,600
5

Beds

4.0

Baths

2,918

Sq.Ft.

2075 JEWELL AVENUE

Winter Park, FL

Courtesy of URBANISTA BROKERS
View 1049 N KENTUCKY AVENUE Winter Park, FL MLS# O6373029
$6,000
3

Beds

2.1

Baths

2,112

Sq.Ft.

1049 N KENTUCKY AVENUE

Winter Park, FL

View 301 W COMSTOCK AVENUE Winter Park, FL MLS# O6385827
  • New Construction with Virtual Tour
1 of 12
$6,000
2

Beds

2.1

Baths

1,500

Sq.Ft.

301 W COMSTOCK AVENUE

Winter Park, FL

View 1791 SPRUCE AVENUE Winter Park, FL MLS# O6420234
$4,900
3

Beds

2.0

Baths

1,776

Sq.Ft.

1791 SPRUCE AVENUE

Winter Park, FL

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 7864 BROKEN ARROW TRAIL Winter Park, FL MLS# O6406209
$3,400
4

Beds

2.1

Baths

2,219

Sq.Ft.

7864 BROKEN ARROW TRAIL

Winter Park, FL

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

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

375

Estimated median home price

$759,000
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 - 100K8
$100K - 200K43
$200K - 300K24
$300K - 400K18
$400K - 500K31
$500K - 600K24
$600K - 700K31
$700K - 800K15
$800K - 900K14
$900K - 1M10
$1M - Max157

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family229
Townhouse19
Condo83
Commercial11
Rental66
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 7/25/2026)

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 7/25/2026.