26 total properties
Did you mean the neighborhood Winter Park?
View 1960 WINTER PARK ROAD Winter Park, FL MLS# O6398264
$899,000
Studio

Beds

0.0

Baths

1960 WINTER PARK ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6398302
  • Recently Listed with Virtual Tour
1 of 5
$929,900
Studio

Beds

0.0

Baths

2823 WRIGHT AVENUE

Winter Park, FL

Courtesy of TAL BUSIDAN PA
View 1507 GOLFSIDE DRIVE Winter Park, FL MLS# O6395355
  • Recently Listed with Virtual Tour
1 of 44
OPEN HOUSE: Sunday 4/19 12:00 PM - 2:00 PM
$975,000
3

Beds

2.0

Baths

2,003

Sq.Ft.

1507 GOLFSIDE DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
View 422 BALMORAL ROAD Winter Park, FL MLS# R4910985
$899,000
3

Beds

2.0

Baths

1,800

Sq.Ft.

422 BALMORAL ROAD

Winter Park, FL

Courtesy of CENTRAL FLORIDA REAL ESTATE CE
View 1836 GRINNELL TERRACE Winter Park, FL MLS# O6395188
$1,050,000
Studio

Beds

0.0

Baths

1836 GRINNELL TERRACE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 250 CORTLAND AVENUE Winter Park, FL MLS# O6395137
  • Recently Listed with Virtual Tour
1 of 46
$950,000
3

Beds

2.0

Baths

2,114

Sq.Ft.

250 CORTLAND AVENUE

Winter Park, FL

Courtesy of CREEGAN GROUP
View 668 OVERSPIN DRIVE Winter Park, FL MLS# O6392301
$875,000
4

Beds

3.0

Baths

2,509

Sq.Ft.

668 OVERSPIN DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2119 HOWARD DRIVE Winter Park, FL MLS# O6390345
$850,000
4

Beds

2.0

Baths

2,479

Sq.Ft.

2119 HOWARD DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6390670
  • Virtual Tour
1 of 19
OPEN HOUSE: Sunday 4/19 1:00 PM - 4:00 PM
$929,900
3

Beds

2.0

Baths

1,536

Sq.Ft.

2823 WRIGHT AVENUE

Winter Park, FL

Courtesy of TAL BUSIDAN PA
View Lot #21 KAROLINA AVE Winter Park, FL MLS# O6387812
  • New Construction with Virtual Tour
1 of 9
$944,890
4

Beds

3.1

Baths

2,662

Sq.Ft.

Lot #21 KAROLINA AVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1768 MONDRIAN CIRCLE Winter Park, FL MLS# O6375723
$1,099,000
3

Beds

3.1

Baths

2,193

Sq.Ft.

1768 MONDRIAN CIRCLE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 628 DUNBLANE DRIVE Winter Park, FL MLS# O6387091
$849,000
3

Beds

2.1

Baths

2,114

Sq.Ft.

628 DUNBLANE DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1405 MILLER AVENUE Winter Park, FL MLS# O6386405
$899,000
3

Beds

2.1

Baths

1,884

Sq.Ft.

1405 MILLER AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1927 ELAND AVENUE Winter Park, FL MLS# O6381009
$850,000
5

Beds

3.0

Baths

2,242

Sq.Ft.

1927 ELAND AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1836 GRINNELL TERRACE Winter Park, FL MLS# O6380457
$1,050,000
3

Beds

2.0

Baths

1,907

Sq.Ft.

1836 GRINNELL TERRACE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1541 WESTCHESTER AVENUE Winter Park, FL MLS# O6374409
$1,100,000
3

Beds

2.1

Baths

2,578

Sq.Ft.

1541 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1541 WESTCHESTER AVENUE Winter Park, FL MLS# O6374414
$1,100,000
Studio

Beds

0.0

Baths

1541 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 520 FITZWALTER DRIVE Winter Park, FL MLS# O6380171
$1,000,000
3

Beds

2.0

Baths

2,111

Sq.Ft.

520 FITZWALTER DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 731 MIDGET DRIVE Winter Park, FL MLS# O6368705
$940,000
Studio

Beds

0.0

Baths

731 MIDGET DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 1780 BRYAN AVENUE Winter Park, FL MLS# O6365369
$849,000
4

Beds

2.0

Baths

1,617

Sq.Ft.

1780 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK

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

$795,000
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 - 100K4
$100K - 200K50
$200K - 300K22
$300K - 400K18
$400K - 500K29
$500K - 600K19
$600K - 700K23
$700K - 800K14
$800K - 900K13
$900K - 1M10
$1M - Max153

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family215
Townhouse14
Condo89
Commercial3
Rental91
Lots and Land27
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 4/16/2026)

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 4/16/2026.