View 729 MEADOW GLADE DRIVE Winter Garden, FL MLS# O6407943
$515,000
3

Beds

2.0

Baths

2,070

Sq.Ft.

729 MEADOW GLADE DRIVE

Winter Garden, FL

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

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVE 1535 1535

Winter Garden, FL

Courtesy of SACKS REALTY GROUP, INC.
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

The time to sell is now! THE TIME TO SELL IS NOW!
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

Courtesy of LA ROSA REALTY LLC
View 12597 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6407413
$475,000
3

Beds

2.0

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: Tuesday 7/14 9:00 AM - 7:00 PM
$475,000
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 6174 WHISPERING GLEN Winter Garden, FL MLS# O6407807
  • New Construction with Virtual Tour
1 of 20
$518,290
3

Beds

2.1

Baths

1,628

Sq.Ft.

6174 WHISPERING GLEN

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
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
$515,000
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

Courtesy of MY REALTY GROUP, LLC.
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

Courtesy of CRAIG BURKE REAL ESTATE GROUP, LLC
View 14501 Grove Resort 1304 Winter Garden, FL MLS# A12022081
$350,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 Grove Resort 1304

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 11072 SILVER SURFER ALLEY Winter Garden, FL MLS# O6406656
$440,000
3

Beds

2.1

Baths

1,770

Sq.Ft.

11072 SILVER SURFER ALLEY

Winter Garden, FL

View 13552 AUTUMN HARVEST AVENUE Winter Garden, FL MLS# O6404264
$515,000
3

Beds

3.0

Baths

1,955

Sq.Ft.

13552 AUTUMN HARVEST AVENUE

Winter Garden, FL

Courtesy of REALTY ONE GROUP EVOLUTION
View 15051 GROVESIDE ROAD Winter Garden, FL MLS# O6406358
  • New Construction with Virtual Tour
1 of 6
$490,575
3

Beds

2.1

Baths

1,846

Sq.Ft.

15051 GROVESIDE ROAD

Winter Garden, FL

View 13299 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5112134
  • New Construction with Virtual Tour
1 of 26
$449,990
3

Beds

2.1

Baths

1,729

Sq.Ft.

13299 PEACEFUL MELODY DRIVE

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

939

Estimated median home price

$599,999
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 - 700K105
$700K - 800K95
$800K - 900K86
$900K - 1M63
$1M - Max118

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family640
Townhouse130
Condo135
Commercial11
Rental199
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 7/13/2026)

Information deemed reliable but not guaranteed.

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

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 7/14/2026.