View 2010 BOSS HEWETT STREET Winter Garden, FL MLS# O6423216
  • Recently Listed with Virtual Tour
1 of 94
$1,500,000
5

Beds

4.0

Baths

3,781

Sq.Ft.

2010 BOSS HEWETT STREET

Winter Garden, FL

Courtesy of RE/MAX ASSURED
View 15619 GIANT FOXTAIL COURT Winter Garden, FL MLS# O6422589
  • Recently Listed with Virtual Tour
1 of 69
$1,450,000
4

Beds

3.1

Baths

3,086

Sq.Ft.

15619 GIANT FOXTAIL COURT

Winter Garden, FL

View 10198 MERRYMEETING BAY DRIVE Winter Garden, FL MLS# O6421817
  • Recently Listed with Virtual Tour
1 of 42
OPEN HOUSE: Saturday 7/11 12:00 PM - 3:00 PM
$1,200,000
5

Beds

3.1

Baths

3,911

Sq.Ft.

10198 MERRYMEETING BAY DRIVE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 7467 JOHN HANCOCK DRIVE Winter Garden, FL MLS# O6421848
  • Recently Listed with Virtual Tour
1 of 90
$1,350,000
4

Beds

3.1

Baths

3,964

Sq.Ft.

7467 JOHN HANCOCK DRIVE

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 9976 BEACH PORT DRIVE Winter Garden, FL MLS# O6420960
$1,274,000
5

Beds

3.1

Baths

3,910

Sq.Ft.

9976 BEACH PORT DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 14591 BLACK QUILL DRIVE Winter Garden, FL MLS# O6420836
  • Recently Listed with Virtual Tour
1 of 61
$1,335,000
4

Beds

3.1

Baths

4,057

Sq.Ft.

14591 BLACK QUILL DRIVE

Winter Garden, FL

View 15264 SHONAN GOLD DRIVE Winter Garden, FL MLS# O6418870
  • Recently Listed with Virtual Tour
1 of 74
$1,399,999
4

Beds

3.1

Baths

4,000

Sq.Ft.

15264 SHONAN GOLD DRIVE

Winter Garden, FL

View 844 OAKLAND PARK BOULEVARD Winter Garden, FL MLS# O6419976
  • Recently Listed with Virtual Tour
1 of 74
$1,225,000
5

Beds

4.0

Baths

3,525

Sq.Ft.

844 OAKLAND PARK BOULEVARD

Winter Garden, FL

View 9969 LOST CREEK DRIVE Winter Garden, FL MLS# O6419414
  • Recently Listed with Virtual Tour
1 of 84
$1,299,000
5

Beds

3.1

Baths

3,910

Sq.Ft.

9969 LOST CREEK DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 15591 PANTHER LAKE DRIVE Winter Garden, FL MLS# O6416459
$1,299,000
5

Beds

3.1

Baths

3,932

Sq.Ft.

15591 PANTHER LAKE DRIVE

Winter Garden, FL

View 15741 SWEET LEMON WAY Winter Garden, FL MLS# O6417058
$1,165,000
5

Beds

4.1

Baths

3,624

Sq.Ft.

15741 SWEET LEMON WAY

Winter Garden, FL

View 925 EASLEY AVENUE Winter Garden, FL MLS# O6412977
$1,175,000
4

Beds

3.1

Baths

2,667

Sq.Ft.

925 EASLEY AVENUE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
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 16614 HARBOR SAIL WAY Winter Garden, FL MLS# O6414639
$1,495,000
6

Beds

5.1

Baths

4,882

Sq.Ft.

16614 HARBOR SAIL WAY

Winter Garden, FL

View 8530 BAYVIEW CROSSING DRIVE Winter Garden, FL MLS# O6413249
$1,499,000
4

Beds

4.0

Baths

4,130

Sq.Ft.

8530 BAYVIEW CROSSING DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 650 MEDORA WAY Winter Garden, FL MLS# O6413464
  • New Construction with Virtual Tour
1 of 12
$1,157,190
4

Beds

3.0

Baths

2,902

Sq.Ft.

650 MEDORA WAY

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
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 15326 JOHNS LAKE POINTE BOULEVARD Winter Garden, FL MLS# S5150851
$1,385,000
4

Beds

3.1

Baths

3,495

Sq.Ft.

15326 JOHNS LAKE POINTE BOULEVARD

Winter Garden, FL

View 9189 BUSACO PARK WAY Winter Garden, FL MLS# O6410698
$1,300,000
4

Beds

4.0

Baths

3,424

Sq.Ft.

9189 BUSACO PARK WAY

Winter Garden, FL

View 16217 LAKE JOHNS CIRCLE Winter Garden, FL MLS# O6409098
$1,200,000
5

Beds

5.0

Baths

4,659

Sq.Ft.

16217 LAKE JOHNS CIRCLE

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

937

Estimated median home price

$599,990
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 - 300K89
$300K - 400K65
$400K - 500K132
$500K - 600K163
$600K - 700K102
$700K - 800K95
$800K - 900K87
$900K - 1M62
$1M - Max119

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family637
Townhouse130
Condo135
Commercial11
Rental199
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 7/11/2026)

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 7/11/2026.