View 950 S DILLARD STREET Winter Garden, FL MLS# O6359585
  • New Construction with Virtual Tour
1 of 8
$538,350
4,909

Sq.Ft.

950 S DILLARD STREET

Winter Garden, FL

View 12143 STONEYBROOK WEST PARKWAY 101-102 Winter Garden, FL MLS# O6428942
  • New Construction with Virtual Tour
1 of 8
$394,200
7,300

Sq.Ft.

12143 STONEYBROOK WEST PARKWAY 101-102

Winter Garden, FL

View 12283 STONEYBROOK WEST PARKWAY B Winter Garden, FL MLS# O6425191
  • New Construction with Virtual Tour
1 of 17
$108,000
2,400

Sq.Ft.

12283 STONEYBROOK WEST PARKWAY B

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 12324 W COLONIAL DRIVE Winter Garden, FL MLS# O6264561
  • New Construction with Virtual Tour
1 of 19
$54,000
3,025

Sq.Ft.

12324 W COLONIAL DRIVE

Winter Garden, FL

View 705 HENNIS ROAD Winter Garden, FL MLS# O6390677
  • New Construction with Virtual Tour
1 of 18
$52,206
11,865

Sq.Ft.

705 HENNIS ROAD

Winter Garden, FL

View 215 CENTER STREET 227 Winter Garden, FL MLS# O6415984
$43,794
2,304

Sq.Ft.

215 CENTER STREET 227

Winter Garden, FL

View 595 9TH STREET 115 Winter Garden, FL MLS# O6398346
$42,000
1,204

Sq.Ft.

595 9TH STREET 115

Winter Garden, FL

View 595 9TH STREET Winter Garden, FL MLS# O6398340
  • Virtual Tour
1 of 17
$34,800
1,204

Sq.Ft.

595 9TH STREET

Winter Garden, FL

View 16870 SANCTUARY DRIVE Winter Garden, FL MLS# O6394261
  • Adult Community with Virtual Tour
1 of 100
$12,950
5

Beds

5.0

Baths

4,038

Sq.Ft.

16870 SANCTUARY DRIVE

Winter Garden, FL

Courtesy of FORTUNE GLOBAL REALTY
View 595 9TH STREET 116 Winter Garden, FL MLS# O6398351
$12,000
1,204

Sq.Ft.

595 9TH STREET 116

Winter Garden, FL

View 7573 GREEN MOUNTAIN WAY Winter Garden, FL MLS# O6423959
$8,000
4

Beds

3.1

Baths

3,333

Sq.Ft.

7573 GREEN MOUNTAIN WAY

Winter Garden, FL

View 7759 GREEN MOUNTAIN WAY Winter Garden, FL MLS# O6411481
$7,500
6

Beds

6.1

Baths

5,174

Sq.Ft.

7759 GREEN MOUNTAIN WAY

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 14807 WINTER STAY DRIVE Winter Garden, FL MLS# O6434655
  • Recently Listed with Virtual Tour
1 of 67
$6,500
5

Beds

4.0

Baths

3,856

Sq.Ft.

14807 WINTER STAY DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 353 LAKE AMBERLEIGH DRIVE Winter Garden, FL MLS# S5155795
$6,500
4

Beds

2.1

Baths

2,762

Sq.Ft.

353 LAKE AMBERLEIGH DRIVE

Winter Garden, FL

View 706 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6416527
$6,000
5

Beds

5.2

Baths

4,019

Sq.Ft.

706 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 15075 TEA TREE DRIVE Winter Garden, FL MLS# O6428708
  • Recently Listed with Virtual Tour
1 of 38
$6,000
4

Beds

3.0

Baths

3,038

Sq.Ft.

15075 TEA TREE DRIVE

Winter Garden, FL

View 14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL MLS# O6430003
  • Recently Listed with Virtual Tour
1 of 72
$6,000
4

Beds

3.2

Baths

4,010

Sq.Ft.

14411 HAMPSHIRE BAY CIRCLE

Winter Garden, FL

View 15155 CANOE PLACE Winter Garden, FL MLS# O6433426
  • Recently Listed with Virtual Tour
1 of 38
$6,000
5

Beds

4.1

Baths

4,045

Sq.Ft.

15155 CANOE PLACE

Winter Garden, FL

View 14612 GLADE HILL PARK WAY Winter Garden, FL MLS# S5151295
$5,900
5

Beds

4.1

Baths

3,892

Sq.Ft.

14612 GLADE HILL PARK WAY

Winter Garden, FL

View 9247 LEGADO DRIVE Winter Garden, FL MLS# O6433071
  • Recently Listed with Virtual Tour
1 of 100
$5,500
4

Beds

2.1

Baths

2,549

Sq.Ft.

9247 LEGADO DRIVE

Winter Garden, FL

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

1,018

Estimated median home price

$611,805
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

Price Count
$0 - 100K 2
$100K - 200K 21
$200K - 300K 89
$300K - 400K 78
$400K - 500K 147
$500K - 600K 164
$600K - 700K 110
$700K - 800K 117
$800K - 900K 108
$900K - 1M 63
$1M - Max 119

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 702
Townhouse 144
Condo 136
Commercial 9
Rental 177
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 8/19/2026)

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 8/19/2026.