View 15877 TOLLINGTON ALLEY Winter Garden, FL MLS# O6427665
  • Recently Listed with Virtual Tour
1 of 39
OPEN HOUSE: Saturday 8/22 1:00 PM - 3:00 PM
$493,500
3

Beds

2.1

Baths

1,835

Sq.Ft.

15877 TOLLINGTON ALLEY

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
View 300 S WOODLAND STREET Winter Garden, FL MLS# O6431568
$545,000
3

Beds

2.0

Baths

1,774

Sq.Ft.

300 S WOODLAND STREET

Winter Garden, FL

View 14501 Grove Resort Ave 3626 Winter Garden, FL MLS# A12074646
  • Recently Listed with Virtual Tour
1 of 29
$480,000
3

Beds

3.0

Baths

14501 Grove Resort Ave 3626

Winter Garden, FL

Courtesy of REAL ESTATE SALES FORCE
The time to sell is now! THE TIME TO SELL IS NOW!
View 1097 DEPOT COURT Winter Garden, FL MLS# O6425177
  • Recently Listed with Virtual Tour
1 of 40
$479,900
3

Beds

2.0

Baths

1,583

Sq.Ft.

1097 DEPOT COURT

Winter Garden, FL

View 8016 SWEET ORANGE AVENUE Winter Garden, FL MLS# O6434740
  • Recently Listed with Virtual Tour
1 of 49
$514,900
4

Beds

2.1

Baths

2,084

Sq.Ft.

8016 SWEET ORANGE AVENUE

Winter Garden, FL

View 618 BAINBRIDGE LOOP Winter Garden, FL MLS# O6433781
  • Recently Listed with Virtual Tour
1 of 32
$580,000
4

Beds

2.0

Baths

2,328

Sq.Ft.

618 BAINBRIDGE LOOP

Winter Garden, FL

View 14543 GOLDEN HARBOR LANE Winter Garden, FL MLS# O6433451
  • Recently Listed with Virtual Tour
1 of 75
$499,999
3

Beds

2.1

Baths

2,039

Sq.Ft.

14543 GOLDEN HARBOR LANE

Winter Garden, FL

View 16534 BARBOURS CREEK WAY Winter Garden, FL MLS# O6433686
  • Recently Listed with Virtual Tour
1 of 18
$464,990
3

Beds

2.1

Baths

1,817

Sq.Ft.

16534 BARBOURS CREEK WAY

Winter Garden, FL

View 15163 BOOK CLUB ROAD Winter Garden, FL MLS# O6432972
  • Recently Listed with Virtual Tour
1 of 25
$560,000
4

Beds

3.1

Baths

2,502

Sq.Ft.

15163 BOOK CLUB ROAD

Winter Garden, FL

Courtesy of PRIMESTATE REALTY, INC.
View 8111 PACIFIC LOON STREET Winter Garden, FL MLS# O6433324
  • Recently Listed with Virtual Tour
1 of 41
$610,000
5

Beds

2.1

Baths

2,668

Sq.Ft.

8111 PACIFIC LOON STREET

Winter Garden, FL

View 745 MARSH REED DRIVE W Winter Garden, FL MLS# O6433504
  • Recently Listed with Virtual Tour
1 of 17
$560,000
4

Beds

2.1

Baths

2,596

Sq.Ft.

745 MARSH REED DRIVE W

Winter Garden, FL

Courtesy of RE FLORIDA HOMES
View 15213 GROVESIDE ROAD Winter Garden, FL MLS# O6433072
  • Recently Listed with Virtual Tour
1 of 53
$480,085
3

Beds

2.1

Baths

1,846

Sq.Ft.

15213 GROVESIDE ROAD

Winter Garden, FL

Courtesy of DRB GROUP REALTY, LLC
View 231 E LAFAYETTE STREET Winter Garden, FL MLS# O6425940
  • Recently Listed with Virtual Tour
1 of 43
$479,900
4

Beds

3.0

Baths

1,608

Sq.Ft.

231 E LAFAYETTE STREET

Winter Garden, FL

View 10301 AUSTRINA OAK LOOP Winter Garden, FL MLS# G5116017
  • Recently Listed with Virtual Tour
1 of 18
$520,000
3

Beds

2.1

Baths

2,078

Sq.Ft.

10301 AUSTRINA OAK LOOP

Winter Garden, FL

View 16602 WINGSPREAD LOOP Winter Garden, FL MLS# O6429266
$599,900
3

Beds

2.1

Baths

2,372

Sq.Ft.

16602 WINGSPREAD LOOP

Winter Garden, FL

View 636 SIGLER DRIVE Winter Garden, FL MLS# O6431622
  • Recently Listed with Virtual Tour
1 of 13
$611,610
3

Beds

2.1

Baths

1,634

Sq.Ft.

636 SIGLER DRIVE

Winter Garden, FL

Courtesy of DAVILA HOMES
View 4855 PALMETTO PARK DRIVE Winter Garden, FL MLS# O6431798
$599,900
4

Beds

2.0

Baths

2,091

Sq.Ft.

4855 PALMETTO PARK DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 4981 CORAL BEAN ALLEY Winter Garden, FL MLS# O6430193
  • Recently Listed with Virtual Tour
1 of 53
$574,900
4

Beds

2.1

Baths

2,114

Sq.Ft.

4981 CORAL BEAN ALLEY

Winter Garden, FL

View 16954 TRADEWIND POINT Winter Garden, FL MLS# O6431248
$482,000
3

Beds

2.0

Baths

1,692

Sq.Ft.

16954 TRADEWIND POINT

Winter Garden, FL

View 9445 KOMIKA LANE Winter Garden, FL MLS# O6431357
  • Recently Listed with Virtual Tour
1 of 40
$549,000
4

Beds

3.1

Baths

2,477

Sq.Ft.

9445 KOMIKA LANE

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

1,019

Estimated median home price

$614,990
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 - 100K2
$100K - 200K21
$200K - 300K90
$300K - 400K77
$400K - 500K146
$500K - 600K164
$600K - 700K110
$700K - 800K117
$800K - 900K108
$900K - 1M65
$1M - Max119

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family703
Townhouse144
Condo136
Commercial9
Rental173
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 8/20/2026)

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 8/21/2026.