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

The time to sell is now! THE TIME TO SELL IS NOW!
View 9318 MCLAREN ALLEY Winter Garden, FL MLS# S5150019
$489,000
3

Beds

2.0

Baths

1,685

Sq.Ft.

9318 MCLAREN ALLEY

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 1439 Winter Garden, FL MLS# O6407410
$169,900
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1439

Winter Garden, FL

View 12103 EASTMOOR DRIVE Winter Garden, FL MLS# O6409071
$440,000
3

Beds

2.0

Baths

1,604

Sq.Ft.

12103 EASTMOOR DRIVE

Winter Garden, FL

View 14501 GROVE RESORT AVE 1535 Winter Garden, FL MLS# S5150001
$410,990
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVE 1535

Winter Garden, FL

View 13527 DANIELS LANDING CIRCLE Winter Garden, FL MLS# O6408480
$335,000
3

Beds

2.1

Baths

1,365

Sq.Ft.

13527 DANIELS LANDING CIRCLE

Winter Garden, FL

View 170 WINDTREE LANE Winter Garden, FL MLS# S5150050
$204,900
2

Beds

2.0

Baths

918

Sq.Ft.

170 WINDTREE LANE

Winter Garden, FL

View 12597 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6407413
$465,000
3

Beds

2.1

Baths

2,322

Sq.Ft.

12597 ENCORE AT OVATION WAY

Winter Garden, FL

View 5545 BOWMAN DRIVE Winter Garden, FL MLS# O6407484
  • Virtual Tour
1 of 29
OPEN HOUSE: Monday 7/27 9:00 AM - 7:00 PM
$465,000
2

Beds

2.1

Baths

1,998

Sq.Ft.

5545 BOWMAN DRIVE

Winter Garden, FL

View 441 E CYPRESS STREET Winter Garden, FL MLS# O6407560
$305,000
Studio

Beds

0.0

Baths

441 E CYPRESS STREET

Winter Garden, FL

View 342 WINDFORD COURT Winter Garden, FL MLS# O6407632
$319,900
3

Beds

2.0

Baths

1,194

Sq.Ft.

342 WINDFORD COURT

Winter Garden, FL

View 11117 BOSTWICK ALLEY Winter Garden, FL MLS# O6407552
$507,000
3

Beds

2.0

Baths

1,685

Sq.Ft.

11117 BOSTWICK ALLEY

Winter Garden, FL

View 1015 WESTSIDE DRIVE Winter Garden, FL MLS# O6407229
$224,000
3

Beds

2.0

Baths

938

Sq.Ft.

1015 WESTSIDE DRIVE

Winter Garden, FL

View 1431 VISCAYA COVE BOULEVARD Winter Garden, FL MLS# O6407306
$499,900
4

Beds

3.0

Baths

2,030

Sq.Ft.

1431 VISCAYA COVE BOULEVARD

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 243 FLORIDA AVENUE Winter Garden, FL MLS# S5149991
$335,000
2

Beds

2.0

Baths

1,100

Sq.Ft.

243 FLORIDA AVENUE

Winter Garden, FL

View 12308 BRACCO STREET Winter Garden, FL MLS# O6406923
$505,000
4

Beds

2.1

Baths

2,094

Sq.Ft.

12308 BRACCO STREET

Winter Garden, FL

Courtesy of ELITE INTERNATIONAL REALTY INC
View 1681 E SPRING RIDGE CIRCLE Winter Garden, FL MLS# B4902258
$469,000
4

Beds

2.0

Baths

1,858

Sq.Ft.

1681 E SPRING RIDGE CIRCLE

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 2315 Winter Garden, FL MLS# O6408406
$180,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 2315

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC

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

1,076

Estimated median home price

$612,805
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 - 200K24
$200K - 300K96
$300K - 400K68
$400K - 500K156
$500K - 600K184
$600K - 700K113
$700K - 800K129
$800K - 900K104
$900K - 1M66
$1M - Max135

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family759
Townhouse143
Condo141
Commercial10
Rental221
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/27/2026)

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 7/27/2026.