View 12427 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# O6413423
$499,990
4

Beds

3.0

Baths

2,200

Sq.Ft.

12427 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 1906 SHERBOURNE STREET Winter Garden, FL MLS# S5151079
$477,000
4

Beds

2.1

Baths

2,029

Sq.Ft.

1906 SHERBOURNE STREET

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 17035 HARBOR OAK PARKWAY Winter Garden, FL MLS# O6411409
$485,000
3

Beds

2.0

Baths

1,692

Sq.Ft.

17035 HARBOR OAK PARKWAY

Winter Garden, FL

Courtesy of DALTON WADE INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 420 E CYPRESS STREET Winter Garden, FL MLS# O6412414
$410,000
3

Beds

2.0

Baths

1,616

Sq.Ft.

420 E CYPRESS STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY
View 11025 SUSPENSE DRIVE Winter Garden, FL MLS# G5113196
$410,000
3

Beds

2.1

Baths

1,636

Sq.Ft.

11025 SUSPENSE DRIVE

Winter Garden, FL

View 15806 GEM VIEW ST Winter Garden, FL MLS# C7526682
  • Adult Community with Virtual Tour
1 of 37
$495,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

15806 GEM VIEW ST

Winter Garden, FL

View 16596 POINT ROCK DRIVE Winter Garden, FL MLS# O6412721
$534,900
3

Beds

2.1

Baths

2,216

Sq.Ft.

16596 POINT ROCK DRIVE

Winter Garden, FL

View 2241 WHITE FEATHER LOOP Winter Garden, FL MLS# O6411576
$525,000
3

Beds

2.1

Baths

2,152

Sq.Ft.

2241 WHITE FEATHER LOOP

Winter Garden, FL

View 12253 S BRACCO STREET Winter Garden, FL MLS# S5150840
$499,000
3

Beds

2.1

Baths

1,788

Sq.Ft.

12253 S BRACCO STREET

Winter Garden, FL

Courtesy of LIFESTYLE INTERNATIONAL REALTY
View 14501 GROVE 3425 Winter Garden, FL MLS# A12025972
$420,000
2

Beds

2.0

Baths

14501 GROVE 3425

Winter Garden, FL

Courtesy of MIAMI LIFE REALTY LLC
View 1158 ORANGE SEASON LANE Winter Garden, FL MLS# O6402123
$525,000
3

Beds

2.1

Baths

2,444

Sq.Ft.

1158 ORANGE SEASON LANE

Winter Garden, FL

View 516 S HIGHLAND AVENUE Winter Garden, FL MLS# O6409675
$500,000
3

Beds

2.0

Baths

1,716

Sq.Ft.

516 S HIGHLAND AVENUE

Winter Garden, FL

View 231 DOE RUN DRIVE Winter Garden, FL MLS# O6412284
$494,995
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

Courtesy of EXP REALTY LLC
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 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 33 TIMBERCREEK PINES CIRCLE Winter Garden, FL MLS# O6408941
$525,000
3

Beds

2.0

Baths

1,600

Sq.Ft.

33 TIMBERCREEK PINES CIRCLE

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 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

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

1,026

Estimated median home price

$610,805
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 - 200K21
$200K - 300K86
$300K - 400K77
$400K - 500K155
$500K - 600K166
$600K - 700K116
$700K - 800K113
$800K - 900K109
$900K - 1M64
$1M - Max118

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family711
Townhouse148
Condo131
Commercial9
Rental182
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/27/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

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. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

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 8/28/2026.