35 total properties
Did you mean the neighborhood Winter Park?
View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6390670
  • Virtual Tour
1 of 19
$899,900
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 325 N PHELPS AVENUE Winter Park, FL MLS# O6388118
  • Virtual Tour
1 of 6
$795,000
Studio

Beds

0.0

Baths

325 N PHELPS AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1405 MILLER AVENUE Winter Park, FL MLS# O6386405
  • Virtual Tour
1 of 46
$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
  • Virtual Tour
1 of 68
$825,000
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
$999,000
3

Beds

2.0

Baths

1,907

Sq.Ft.

1836 GRINNELL TERRACE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 675 OVERSPIN DRIVE Winter Park, FL MLS# O6378975
  • Virtual Tour
1 of 32
$775,000
4

Beds

3.1

Baths

3,062

Sq.Ft.

675 OVERSPIN DRIVE

Winter Park, FL

Courtesy of WEMERT GROUP REALTY LLC
View 521 FAIRFAX AVENUE Winter Park, FL MLS# O6399909
  • Virtual Tour
1 of 16
$790,000
4

Beds

2.0

Baths

2,112

Sq.Ft.

521 FAIRFAX AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 520 FITZWALTER DRIVE Winter Park, FL MLS# O6380171
  • Virtual Tour
1 of 47
$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
  • Virtual Tour
1 of 7
$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
  • Virtual Tour
1 of 8
$849,000
4

Beds

2.0

Baths

1,617

Sq.Ft.

1780 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1822 GREENWICH AVENUE Winter Park, FL MLS# A4669605
$995,000
3

Beds

2.0

Baths

1,627

Sq.Ft.

1822 GREENWICH AVENUE

Winter Park, FL

Courtesy of FLATFEE.COM
View 100 S INTERLACHEN AVENUE 503 Winter Park, FL MLS# O6343006
$879,000
2

Beds

2.0

Baths

1,143

Sq.Ft.

100 S INTERLACHEN AVENUE 503

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 560 OLOLU DRIVE Winter Park, FL MLS# O6344540
  • Virtual Tour
1 of 29
$925,000
2

Beds

2.0

Baths

1,086

Sq.Ft.

560 OLOLU DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1018 TURNER ROAD Winter Park, FL MLS# O6314546
  • Virtual Tour
1 of 39
$835,000
3

Beds

2.0

Baths

2,237

Sq.Ft.

1018 TURNER ROAD

Winter Park, FL

Courtesy of WEMERT GROUP REALTY LLC

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

389

Estimated median home price

$790,000
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

Price Count
$0 - 100K 2
$100K - 200K 48
$200K - 300K 24
$300K - 400K 23
$400K - 500K 29
$500K - 600K 22
$600K - 700K 29
$700K - 800K 20
$800K - 900K 15
$900K - 1M 10
$1M - Max 167

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 246
Townhouse 15
Condo 87
Commercial 7
Rental 73
Lots and Land 27
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/25/2026)

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 5/25/2026.