View 14591 BLACK QUILL DRIVE Winter Garden, FL MLS# O6420836
$1,335,000
4

Beds

3.1

Baths

4,057

Sq.Ft.

14591 BLACK QUILL DRIVE

Winter Garden, FL

Courtesy of TOP TIER RESORT REALTY
View 243 ZACHARY WADE STREET Winter Garden, FL MLS# O6391909
$1,300,000
5

Beds

3.1

Baths

3,097

Sq.Ft.

243 ZACHARY WADE STREET

Winter Garden, FL

View 15554 PANTHER LAKE DRIVE Winter Garden, FL MLS# O6405046
$1,299,000
5

Beds

4.1

Baths

4,345

Sq.Ft.

15554 PANTHER LAKE DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 8530 BAYVIEW CROSSING DRIVE Winter Garden, FL MLS# O6413249
$1,299,000
4

Beds

4.0

Baths

4,130

Sq.Ft.

8530 BAYVIEW CROSSING DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 8506 BAYVIEW CROSSING DRIVE Winter Garden, FL MLS# O6421255
$1,299,000
5

Beds

5.0

Baths

3,966

Sq.Ft.

8506 BAYVIEW CROSSING DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 217 W BAY STREET Winter Garden, FL MLS# S5149527
  • Virtual Tour
1 of 89
$1,295,000
5

Beds

4.0

Baths

2,800

Sq.Ft.

217 W BAY STREET

Winter Garden, FL

View 16689 TOCCOA ROW Winter Garden, FL MLS# O6379132
  • Virtual Tour
1 of 97
$1,290,000
5

Beds

5.0

Baths

3,458

Sq.Ft.

16689 TOCCOA ROW

Winter Garden, FL

Courtesy of CHARISMA REALTY CORP
View 16894 WINGSPREAD LOOP Winter Garden, FL MLS# O6362090
$1,270,000
5

Beds

3.1

Baths

3,906

Sq.Ft.

16894 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of THE BRAHMIN GROUP
View 14240 COLONIAL POINTE DRIVE Winter Garden, FL MLS# O6412255
$1,250,000
6

Beds

5.1

Baths

4,816

Sq.Ft.

14240 COLONIAL POINTE DRIVE

Winter Garden, FL

View 5513 THOMAS SQUARE DRIVE Winter Garden, FL MLS# O6428640
$1,250,000
4

Beds

3.1

Baths

3,941

Sq.Ft.

5513 THOMAS SQUARE DRIVE

Winter Garden, FL

Courtesy of SERHANT
View 1734 AMSEL FALLS PARK TERRACE Winter Garden, FL MLS# O6427494
$1,249,990
5

Beds

3.2

Baths

4,305

Sq.Ft.

1734 AMSEL FALLS PARK TERRACE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 13217 TOLLCROSS WAY Winter Garden, FL MLS# O6285385
  • New Construction
1 of 78
$1,249,000
6

Beds

5.0

Baths

4,152

Sq.Ft.

13217 TOLLCROSS WAY

Winter Garden, FL

View 706 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6394059
$1,225,000
5

Beds

5.2

Baths

4,019

Sq.Ft.

706 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 15594 SHOREBIRD LANE Winter Garden, FL MLS# S5147208
$1,219,000
4

Beds

3.1

Baths

3,022

Sq.Ft.

15594 SHOREBIRD LANE

Winter Garden, FL

View 15838 CITRUS GROVE LOOP Winter Garden, FL MLS# S5153907
$1,219,000
5

Beds

4.0

Baths

3,505

Sq.Ft.

15838 CITRUS GROVE LOOP

Winter Garden, FL

View 205 SURPRISE DRIVE Winter Garden, FL MLS# O6365188
  • Virtual Tour
1 of 32
$1,200,000
4

Beds

2.1

Baths

2,171

Sq.Ft.

205 SURPRISE DRIVE

Winter Garden, FL

View 1812 LAKE ROBERTS LANDING DRIVE Winter Garden, FL MLS# O6415935
$1,200,000
6

Beds

4.0

Baths

4,247

Sq.Ft.

1812 LAKE ROBERTS LANDING DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 9969 LOST CREEK DRIVE Winter Garden, FL MLS# O6419414
$1,199,000
5

Beds

3.1

Baths

3,910

Sq.Ft.

9969 LOST CREEK DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 9189 BUSACO PARK WAY Winter Garden, FL MLS# O6410698
$1,198,000
4

Beds

4.0

Baths

3,424

Sq.Ft.

9189 BUSACO PARK WAY

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 844 OAKLAND PARK BOULEVARD Winter Garden, FL MLS# O6419976
$1,195,000
5

Beds

4.0

Baths

3,525

Sq.Ft.

844 OAKLAND PARK BOULEVARD

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY

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

1,023

Estimated median home price

$605,000
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 1
$100K - 200K 22
$200K - 300K 90
$300K - 400K 78
$400K - 500K 153
$500K - 600K 167
$600K - 700K 109
$700K - 800K 113
$800K - 900K 110
$900K - 1M 62
$1M - Max 118

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 709
Townhouse 145
Condo 133
Commercial 9
Rental 189
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 1
Farms 0

(Data as of 8/30/2026)

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 8/30/2026.