View 508 VARSITY STREET Winter Garden, FL MLS# O6401722
$1,695
2

Beds

1.0

Baths

780

Sq.Ft.

508 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 16593 BARBOURS CREEK WAY Winter Garden, FL MLS# O6400540
  • New Construction with Virtual Tour
1 of 28
$3,000
3

Beds

2.1

Baths

1,567

Sq.Ft.

16593 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of KAZA REAL ESTATE LLC
View 13527 DANIELS LANDING CIRCLE Winter Garden, FL MLS# S5148507
$2,300
3

Beds

2.1

Baths

1,365

Sq.Ft.

13527 DANIELS LANDING CIRCLE

Winter Garden, FL

Courtesy of Kissimmee - WEICHERT, REALTORS® - Hallmark Properties
The time to sell is now! THE TIME TO SELL IS NOW!
View 16822 WINGSPREAD LOOP Winter Garden, FL MLS# O6402231
$3,950
4

Beds

3.0

Baths

2,470

Sq.Ft.

16822 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of ASSURANCE FLORIDA REALTY
View 15030 SUMMER HARVEST STREET Winter Garden, FL MLS# O6400523
  • New Construction with Virtual Tour
1 of 17
$3,800
4

Beds

3.1

Baths

2,861

Sq.Ft.

15030 SUMMER HARVEST STREET

Winter Garden, FL

Courtesy of KICANTO REALTY
View 12032 HOLYSTONE STREET Winter Garden, FL MLS# O6401473
$2,600
3

Beds

2.1

Baths

1,568

Sq.Ft.

12032 HOLYSTONE STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 15883 TOLLINGTON ALLEY Winter Garden, FL MLS# O6401288
$2,950
3

Beds

2.1

Baths

1,850

Sq.Ft.

15883 TOLLINGTON ALLEY

Winter Garden, FL

Courtesy of DALTON WADE INC
View 430 SOUTHERN PECAN CIRCLE 101 Winter Garden, FL MLS# O6401124
$2,000
2

Beds

2.0

Baths

1,152

Sq.Ft.

430 SOUTHERN PECAN CIRCLE 101

Winter Garden, FL

Courtesy of ORLANDO REAL ESTATE LLC
View 376 DOUGLAS WAY 73 Winter Garden, FL MLS# O6401072
$1,650
3

Beds

2.0

Baths

930

Sq.Ft.

376 DOUGLAS WAY 73

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 16350 HAMLIN VIEW STREET Winter Garden, FL MLS# O6400898
  • New Construction with Virtual Tour
1 of 67
$3,000
3

Beds

2.1

Baths

1,644

Sq.Ft.

16350 HAMLIN VIEW STREET

Winter Garden, FL

Courtesy of WEBB FLORIDA REALTY LLC
View 15465 HONEYBELL DRIVE Winter Garden, FL MLS# S5148254
$2,700
3

Beds

2.1

Baths

1,584

Sq.Ft.

15465 HONEYBELL DRIVE

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 16029 TOLLINGTON ALLEY Winter Garden, FL MLS# P4938381
$3,350
3

Beds

2.1

Baths

2,341

Sq.Ft.

16029 TOLLINGTON ALLEY

Winter Garden, FL

Courtesy of IAD FLORIDA LLC
View 12097 BRACCO STREET Winter Garden, FL MLS# O6396212
$2,850
3

Beds

2.1

Baths

1,770

Sq.Ft.

12097 BRACCO STREET

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 8056 JOHN HANCOCK DRIVE Winter Garden, FL MLS# O6399522
$3,195
3

Beds

2.1

Baths

2,199

Sq.Ft.

8056 JOHN HANCOCK DRIVE

Winter Garden, FL

Courtesy of BAHIA INTERNATIONAL REALTY
View 10042 SALT POINT DRIVE Winter Garden, FL MLS# O6399835
$2,600
3

Beds

2.1

Baths

1,451

Sq.Ft.

10042 SALT POINT DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 216 DEEPCOVE ROAD Winter Garden, FL MLS# O6399926
$2,100
2

Beds

2.1

Baths

1,236

Sq.Ft.

216 DEEPCOVE ROAD

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 15363 HAMLIN PARK DRIVE Winter Garden, FL MLS# O6401538
$3,300
3

Beds

3.1

Baths

1,936

Sq.Ft.

15363 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 16067 PEBBLE BLUFF LOOP Winter Garden, FL MLS# S5147791
$2,900
3

Beds

2.1

Baths

2,012

Sq.Ft.

16067 PEBBLE BLUFF LOOP

Winter Garden, FL

Courtesy of ACKLEY FLORIDA PROPERTY MANAGEMENT INC
View 456 SILVERDALE AVENUE Winter Garden, FL MLS# O6398638
$3,100
4

Beds

2.0

Baths

1,844

Sq.Ft.

456 SILVERDALE AVENUE

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 12506 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# S5148369
$1,600
1

Beds

1.0

Baths

2,900

Sq.Ft.

12506 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC

About Winter Garden

The balance between reverence for yesterday and vibrant growth is reflected in the Winter Garden slogan, "A City with a Future…Preserving Its Past."  Walking down historic Plant Street or catching a glimpse of landmark buildings like Tanner Hall immediately creates an image of small-town life at its finest in the heart of this quaint Main Street community. At the same time, redevelopment and growth are evident at every turn.  Antique stores, ice cream shops, and charming cafés combine with dynamic new businesses and residential development.  Covering approximately 17 square miles, Winter Garden offers access to the West Orange Trail for biking or jogging in a naturally beautiful setting.  Other amenities include large parks, a public boat ramp on Lake Apopka, and recreational complexes for tennis, swimming, and sports play.  This vast area once covered by citrus groves is rapidly transforming into a suburban environment that preserves the friendly, intimate spirit of yesterday.  Residents enjoy easy access to Highway 50, the East West Expressway, and the Florida Turnpike.

Listings in Winter Garden, FL

1,037

Estimated median home price

$609,999
Winter Garden FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Garden, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Garden, FL.

Homes for Sale by Price in Winter Garden, FL

PriceCount
$0 - 100K1
$100K - 200K22
$200K - 300K99
$300K - 400K78
$400K - 500K144
$500K - 600K163
$600K - 700K128
$700K - 800K119
$800K - 900K84
$900K - 1M81
$1M - Max118

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family711
Townhouse142
Condo141
Commercial10
Rental216
Lots and Land30
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 5/18/2026)

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 5/19/2026.