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 241 N DILLARD STREET Winter Garden, FL MLS# O6353975
$1,499,999
4

Beds

3.0

Baths

3,507

Sq.Ft.

241 N DILLARD STREET

Winter Garden, FL

Courtesy of HOMEVEST REALTY
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 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 16115 JOHNS LAKE OVERLOOK DRIVE Winter Garden, FL MLS# O6376626
$1,420,000
5

Beds

4.1

Baths

4,965

Sq.Ft.

16115 JOHNS LAKE OVERLOOK DRIVE

Winter Garden, FL

Courtesy of POWERHOUSE REAL ESTATE NETWORK
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 16669 VARONE COVE COURT Winter Garden, FL MLS# O6375749
$1,399,900
7

Beds

5.0

Baths

5,613

Sq.Ft.

16669 VARONE COVE COURT

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 16548 RAVEN ROCK PLACE Winter Garden, FL MLS# S5144064
$1,399,900
5

Beds

4.1

Baths

4,263

Sq.Ft.

16548 RAVEN ROCK PLACE

Winter Garden, FL

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 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 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 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 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 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 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 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 16776 BROADWATER AVENUE Winter Garden, FL MLS# O6407043
$1,299,900
5

Beds

4.1

Baths

3,713

Sq.Ft.

16776 BROADWATER AVENUE

Winter Garden, FL

View 8978 SONOMA COAST DRIVE Winter Garden, FL MLS# O6393744
$1,299,500
5

Beds

3.1

Baths

3,911

Sq.Ft.

8978 SONOMA COAST DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 7/12/2026.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 7/12/2026.