View 1808 WESTERN TRAILWAY DRIVE Winter Garden, FL MLS# S5152973
  • Recently Listed with Virtual Tour
1 of 34
$599,000
3

Beds

2.0

Baths

1,860

Sq.Ft.

1808 WESTERN TRAILWAY DRIVE

Winter Garden, FL

Courtesy of FLORIDA IN MOTION REALTY INC
View 12026 SHINE VIEW LANE Winter Garden, FL MLS# O6405058
  • New Construction with Virtual Tour
1 of 7
$596,190
3

Beds

2.1

Baths

2,216

Sq.Ft.

12026 SHINE VIEW LANE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 16031 SCARPETTA STREET Winter Garden, FL MLS# O6373345
$595,000
4

Beds

3.1

Baths

2,474

Sq.Ft.

16031 SCARPETTA STREET

Winter Garden, FL

Courtesy of VALSTAR REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 13212 SOCIAL LANE Winter Garden, FL MLS# O6398708
$595,000
4

Beds

2.1

Baths

2,526

Sq.Ft.

13212 SOCIAL LANE

Winter Garden, FL

Courtesy of PMI PRIME HOME
View 15143 BLUE PEACOCK LANE Winter Garden, FL MLS# O6414996
$595,000
4

Beds

3.0

Baths

2,420

Sq.Ft.

15143 BLUE PEACOCK LANE

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 16827 HOBE SOUND COURT Winter Garden, FL MLS# O6376919
  • New Construction with Virtual Tour
1 of 21
$594,990
4

Beds

3.1

Baths

2,489

Sq.Ft.

16827 HOBE SOUND COURT

Winter Garden, FL

View 12451 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# O6411261
$594,990
4

Beds

3.0

Baths

2,500

Sq.Ft.

12451 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

View 12915 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6381156
$594,000
4

Beds

3.0

Baths

2,143

Sq.Ft.

12915 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 15043 PIGEON PLUM LANE Winter Garden, FL MLS# S5143009
$594,000
4

Beds

3.1

Baths

2,695

Sq.Ft.

15043 PIGEON PLUM LANE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View Address not provided Winter Garden, FL MLS# O6399369
$594,000
3

Beds

2.0

Baths

1,827

Sq.Ft.

Address not provided

Winter Garden, FL

View 12566 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6389532
$592,000
4

Beds

3.0

Baths

2,420

Sq.Ft.

12566 WESTHAVEN OAK DRIVE

Winter Garden, FL

View 6339 WILD PERSIMMON WAY Winter Garden, FL MLS# G5102274
$591,830
4

Beds

3.0

Baths

2,102

Sq.Ft.

6339 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 7573 SPRING VALLEY STREET Winter Garden, FL MLS# G5113551
$590,715
4

Beds

3.0

Baths

2,102

Sq.Ft.

7573 SPRING VALLEY STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 7679 SILVER MEADOW STREET Winter Garden, FL MLS# G5109150
$590,490
3

Beds

2.0

Baths

1,772

Sq.Ft.

7679 SILVER MEADOW STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15367 GILLIGAN COURT Winter Garden, FL MLS# O6417175
$590,000
4

Beds

2.1

Baths

2,156

Sq.Ft.

15367 GILLIGAN COURT

Winter Garden, FL

View 14542 BLACK CHERRY TRAIL Winter Garden, FL MLS# O6410574
$589,900
4

Beds

2.1

Baths

2,234

Sq.Ft.

14542 BLACK CHERRY TRAIL

Winter Garden, FL

View 1085 CHASE DRIVE Winter Garden, FL MLS# O6417827
$587,000
4

Beds

3.0

Baths

2,967

Sq.Ft.

1085 CHASE DRIVE

Winter Garden, FL

View 6475 BREEZE FILLED LANE Winter Garden, FL MLS# O6416512
$585,000
5

Beds

3.0

Baths

2,231

Sq.Ft.

6475 BREEZE FILLED LANE

Winter Garden, FL

Courtesy of ONLI REALTY GROUP LLC
View 8937 LAKESHORE POINTE DRIVE Winter Garden, FL MLS# O6420679
  • Recently Listed with Virtual Tour
1 of 39
$585,000
3

Beds

2.1

Baths

2,052

Sq.Ft.

8937 LAKESHORE POINTE DRIVE

Winter Garden, FL

View 7673 SILVER MEADOW STREET Winter Garden, FL MLS# G5108953
$584,880
4

Beds

3.0

Baths

2,102

Sq.Ft.

7673 SILVER MEADOW STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC

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 - 200K21
$200K - 300K89
$300K - 400K64
$400K - 500K134
$500K - 600K163
$600K - 700K103
$700K - 800K94
$800K - 900K87
$900K - 1M63
$1M - Max118

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family638
Townhouse130
Condo135
Commercial11
Rental198
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 7/12/2026)

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.