View 6587 OLD CARRIAGE ROAD Winter Garden, FL MLS# O6421933
$645,000
3

Beds

2.0

Baths

2,224

Sq.Ft.

6587 OLD CARRIAGE ROAD

Winter Garden, FL

View 15411 GILLIGAN COURT Winter Garden, FL MLS# O6418437
$569,900
4

Beds

2.1

Baths

2,152

Sq.Ft.

15411 GILLIGAN COURT

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 16681 SILVER BROOK WAY Winter Garden, FL MLS# O6419693
$539,790
4

Beds

2.1

Baths

1,896

Sq.Ft.

16681 SILVER BROOK WAY

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 14123 FRASIER STREET Winter Garden, FL MLS# S5151909
$550,000
4

Beds

2.1

Baths

2,082

Sq.Ft.

14123 FRASIER STREET

Winter Garden, FL

Courtesy of LEVO REAL ESTATE LLC
View 13023 TRANQUIL WATER ALLEY Winter Garden, FL MLS# O6419366
  • New Construction with Virtual Tour
1 of 51
$539,990
3

Beds

2.1

Baths

2,078

Sq.Ft.

13023 TRANQUIL WATER ALLEY

Winter Garden, FL

Courtesy of LPT REALTY LLC
View 1950 PANTHEON DRIVE Winter Garden, FL MLS# O6418888
$495,000
3

Beds

2.0

Baths

1,754

Sq.Ft.

1950 PANTHEON DRIVE

Winter Garden, FL

View 16950 ARROWHEAD BOULEVARD Winter Garden, FL MLS# S5152294
$620,000
2

Beds

2.0

Baths

1,514

Sq.Ft.

16950 ARROWHEAD BOULEVARD

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 15813 SWEET LEMON WAY Winter Garden, FL MLS# O6418559
$534,000
3

Beds

2.1

Baths

2,119

Sq.Ft.

15813 SWEET LEMON WAY

Winter Garden, FL

View 15587 HAMLIN BLOSSOM AVENUE Winter Garden, FL MLS# O6418163
$619,900
3

Beds

2.0

Baths

1,860

Sq.Ft.

15587 HAMLIN BLOSSOM AVENUE

Winter Garden, FL

View 16131 HAMPTON CROSSING DRIVE Winter Garden, FL MLS# O6417701
$649,900
4

Beds

3.0

Baths

2,117

Sq.Ft.

16131 HAMPTON CROSSING DRIVE

Winter Garden, FL

View 17049 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5113971
$568,191
3

Beds

2.0

Baths

1,772

Sq.Ft.

17049 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

View 15183 BRIDGEWATER CROSSINGS BOULEVARD Winter Garden, FL MLS# O6416462
$520,000
3

Beds

2.1

Baths

1,998

Sq.Ft.

15183 BRIDGEWATER CROSSINGS BOULEVARD

Winter Garden, FL

View 15587 MURCOTT BLOSSOM BOULEVARD Winter Garden, FL MLS# O6415333
$640,000
4

Beds

2.1

Baths

2,751

Sq.Ft.

15587 MURCOTT BLOSSOM BOULEVARD

Winter Garden, FL

View 7558 BISHOP SQUARE DRIVE Winter Garden, FL MLS# O6417556
$536,500
4

Beds

2.0

Baths

1,952

Sq.Ft.

7558 BISHOP SQUARE DRIVE

Winter Garden, FL

View 13037 SERENE GLADE ROAD Winter Garden, FL MLS# G5113926
  • New Construction with Virtual Tour
1 of 34
$559,990
3

Beds

2.1

Baths

1,836

Sq.Ft.

13037 SERENE GLADE ROAD

Winter Garden, FL

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 6316 MANUSCRIPT STREET Winter Garden, FL MLS# O6409661
$599,000
4

Beds

2.1

Baths

2,608

Sq.Ft.

6316 MANUSCRIPT STREET

Winter Garden, FL

View 13019 SERENE GLADE ROAD Winter Garden, FL MLS# G5113698
  • New Construction with Virtual Tour
1 of 61
$549,990
3

Beds

2.1

Baths

2,078

Sq.Ft.

13019 SERENE GLADE ROAD

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

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

920

Estimated median home price

$609,920
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 - 300K92
$300K - 400K64
$400K - 500K130
$500K - 600K147
$600K - 700K100
$700K - 800K101
$800K - 900K90
$900K - 1M59
$1M - Max115

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family624
Townhouse127
Condo136
Commercial11
Rental204
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/17/2026)

Information deemed reliable but not guaranteed.

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.

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 7/18/2026.