View 231 DOE RUN DRIVE Winter Garden, FL MLS# O6412284
$498,995
4

Beds

2.0

Baths

1,972

Sq.Ft.

231 DOE RUN DRIVE

Winter Garden, FL

View 7279 DUXBURY LANE Winter Garden, FL MLS# O6405682
$424,900
3

Beds

2.1

Baths

1,895

Sq.Ft.

7279 DUXBURY LANE

Winter Garden, FL

View 7030 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6410364
$469,000
4

Beds

3.1

Baths

1,920

Sq.Ft.

7030 TWILIGHT BAY DRIVE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 15806 GEM VIEW ST Winter Garden, FL MLS# A12029648
  • Adult Community with Virtual Tour
1 of 37
$495,000
2

Beds

2.0

Baths

15806 GEM VIEW ST

Winter Garden, FL

Courtesy of FAST ACTION REALTY INC
View 15025 EVERGREEN OAK LOOP Winter Garden, FL MLS# O6410108
$490,000
4

Beds

3.1

Baths

2,477

Sq.Ft.

15025 EVERGREEN OAK LOOP

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 15135 GROVESIDE ROAD Winter Garden, FL MLS# O6410287
$483,930
3

Beds

2.1

Baths

1,881

Sq.Ft.

15135 GROVESIDE ROAD

Winter Garden, FL

Courtesy of DRB GROUP REALTY, LLC
View 14200 AVALON ROAD 409 Winter Garden, FL MLS# O6410860
$229,000
2

Beds

2.0

Baths

1,253

Sq.Ft.

14200 AVALON ROAD 409

Winter Garden, FL

View 13759 GOLDEN RUSSET DRIVE Winter Garden, FL MLS# O6409757
$309,000
3

Beds

2.1

Baths

1,647

Sq.Ft.

13759 GOLDEN RUSSET DRIVE

Winter Garden, FL

View 16533 BARBOURS CREEK WAY Winter Garden, FL MLS# O6409798
  • New Construction with Virtual Tour
1 of 18
$470,500
3

Beds

2.1

Baths

1,817

Sq.Ft.

16533 BARBOURS CREEK WAY

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 3429 Winter Garden, FL MLS# O6401719
$317,900
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3429

Winter Garden, FL

View 1503 COLUSO DRIVE Winter Garden, FL MLS# O6410109
$443,000
3

Beds

2.0

Baths

2,187

Sq.Ft.

1503 COLUSO DRIVE

Winter Garden, FL

View 330 SOUTHERN PECAN CIRCLE 205 Winter Garden, FL MLS# S5150108
$289,000
3

Beds

2.0

Baths

1,453

Sq.Ft.

330 SOUTHERN PECAN CIRCLE 205

Winter Garden, FL

Courtesy of US REALTY HUB LLC
View 14501 GROVE RESORT AVENUE 3211 Winter Garden, FL MLS# O6408877
$271,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3211

Winter Garden, FL

View 15625 BOGGY OAK CIRCLE 108B Winter Garden, FL MLS# G5112579
$340,000
3

Beds

2.1

Baths

1,419

Sq.Ft.

15625 BOGGY OAK CIRCLE 108B

Winter Garden, FL

View 9652 AMBER CHESTNUT WAY Winter Garden, FL MLS# O6409704
$430,000
4

Beds

2.1

Baths

1,948

Sq.Ft.

9652 AMBER CHESTNUT WAY

Winter Garden, FL

View 17013 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112484
  • New Construction with Virtual Tour
1 of 5
$455,752
3

Beds

2.1

Baths

1,772

Sq.Ft.

17013 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

View 11 WINDTREE LANE B Winter Garden, FL MLS# O6409169
$195,000
2

Beds

2.0

Baths

918

Sq.Ft.

11 WINDTREE LANE B

Winter Garden, FL

View 17001 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112433
$485,705
3

Beds

2.1

Baths

1,644

Sq.Ft.

17001 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

View 17007 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112438
$491,490
3

Beds

2.1

Baths

1,764

Sq.Ft.

17007 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

View 7280 WINDY WILLOW STREET Winter Garden, FL MLS# G5112439
  • New Construction with Virtual Tour
1 of 5
$493,583
3

Beds

2.1

Baths

1,772

Sq.Ft.

7280 WINDY WILLOW STREET

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

1,082

Estimated median home price

$618,500
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 - 200K23
$200K - 300K95
$300K - 400K67
$400K - 500K156
$500K - 600K184
$600K - 700K115
$700K - 800K133
$800K - 900K104
$900K - 1M68
$1M - Max136

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family766
Townhouse142
Condo139
Commercial11
Rental226
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/24/2026)

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.

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 7/25/2026.