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 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 14591 BLACK QUILL DRIVE Winter Garden, FL MLS# O6420836
  • Recently Listed with Virtual Tour
1 of 60
$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 1144 HULL ISLAND DRIVE Winter Garden, FL MLS# O6418306
$1,699,000
5

Beds

4.1

Baths

4,102

Sq.Ft.

1144 HULL ISLAND DRIVE

Winter Garden, FL

View 15591 PANTHER LAKE DRIVE Winter Garden, FL MLS# O6416459
  • Recently Listed with Virtual Tour
1 of 66
$1,395,000
5

Beds

3.1

Baths

3,932

Sq.Ft.

15591 PANTHER LAKE DRIVE

Winter Garden, FL

View 121 W MAPLE STREET Winter Garden, FL MLS# O6417649
$1,725,000
4

Beds

3.1

Baths

3,243

Sq.Ft.

121 W MAPLE STREET

Winter Garden, FL

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 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 9103 MORGANA COURT Winter Garden, FL MLS# O6409652
$1,599,999
5

Beds

4.1

Baths

4,376

Sq.Ft.

9103 MORGANA COURT

Winter Garden, FL

Courtesy of HAMMOND REALTY GROUP LLC
View 1101 EAGLES PASS WAY Winter Garden, FL MLS# O6408835
$1,649,999
6

Beds

5.0

Baths

4,104

Sq.Ft.

1101 EAGLES PASS WAY

Winter Garden, FL

View 325 CRYSTAL WOOD DRIVE Winter Garden, FL MLS# O6408089
$1,600,000
5

Beds

5.0

Baths

4,442

Sq.Ft.

325 CRYSTAL WOOD DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 15554 PANTHER LAKE DRIVE Winter Garden, FL MLS# O6405046
$1,350,000
5

Beds

4.1

Baths

4,345

Sq.Ft.

15554 PANTHER LAKE DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 279 ZACHARY WADE STREET Winter Garden, FL MLS# O6408014
$1,675,000
5

Beds

3.1

Baths

4,473

Sq.Ft.

279 ZACHARY WADE STREET

Winter Garden, FL

Courtesy of INDEPENDENCE REALTY GROUP LLC
View 9827 BEACH PORT DRIVE Winter Garden, FL MLS# O6405480
$1,374,990
5

Beds

3.1

Baths

3,910

Sq.Ft.

9827 BEACH PORT DRIVE

Winter Garden, FL

Courtesy of SERHANT
View 398 WINTER GROVE BOULEVARD Winter Garden, FL MLS# O6405194
  • New Construction with Virtual Tour
1 of 52
$1,498,440
5

Beds

5.0

Baths

4,442

Sq.Ft.

398 WINTER GROVE BOULEVARD

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 1698 JUNIPER HAMMOCK STREET Winter Garden, FL MLS# V4948569
$1,399,000
7

Beds

4.0

Baths

4,700

Sq.Ft.

1698 JUNIPER HAMMOCK STREET

Winter Garden, FL

Courtesy of Longwood - WEICHERT, REALTORS® - Hallmark Properties
View 720 LAKE BRIM DRIVE Winter Garden, FL MLS# O6387519
$1,699,000
4

Beds

4.0

Baths

3,781

Sq.Ft.

720 LAKE BRIM DRIVE

Winter Garden, FL

Courtesy of BHHS FLORIDA 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

947

Estimated median home price

$609,611
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 - 300K92
$300K - 400K64
$400K - 500K127
$500K - 600K164
$600K - 700K102
$700K - 800K98
$800K - 900K92
$900K - 1M64
$1M - Max121

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family650
Townhouse125
Condo137
Commercial11
Rental200
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 7/9/2026)

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 7/9/2026.