View 13184 DENDY WAY Winter Garden, FL MLS# O6384386
  • New Construction with Virtual Tour
1 of 46
$664,000
4

Beds

2.1

Baths

2,211

Sq.Ft.

13184 DENDY WAY

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
View Address not provided Winter Garden, FL MLS# G5113600
$663,645
4

Beds

2.1

Baths

2,235

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14517 BLACK LAKE PRESERVE STREET Winter Garden, FL MLS# A4674838
$660,000
4

Beds

2.1

Baths

2,569

Sq.Ft.

14517 BLACK LAKE PRESERVE STREET

Winter Garden, FL

Courtesy of DALTON WADE INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 16466 OLIVE HILL DRIVE Winter Garden, FL MLS# O6409922
$660,000
3

Beds

2.1

Baths

2,020

Sq.Ft.

16466 OLIVE HILL DRIVE

Winter Garden, FL

Courtesy of ON ME REALTY
View 1209 CASTLEPORT ROAD Winter Garden, FL MLS# O6390760
$659,000
5

Beds

3.0

Baths

2,812

Sq.Ft.

1209 CASTLEPORT ROAD

Winter Garden, FL

Courtesy of THE PROPERTY STOP LLC
View 14006 FRASIER STREET Winter Garden, FL MLS# O6398760
$658,000
4

Beds

2.1

Baths

2,098

Sq.Ft.

14006 FRASIER STREET

Winter Garden, FL

View 8878 BISMARCK PALM DRIVE Winter Garden, FL MLS# O6418128
$656,500
4

Beds

3.1

Baths

2,581

Sq.Ft.

8878 BISMARCK PALM DRIVE

Winter Garden, FL

View 15143 KIRSTY ALLEY Winter Garden, FL MLS# O6344886
$654,900
5

Beds

3.1

Baths

2,934

Sq.Ft.

15143 KIRSTY ALLEY

Winter Garden, FL

Courtesy of ARION REALTY
View 14008 JOMATT LOOP Winter Garden, FL MLS# O6376903
$650,000
4

Beds

3.0

Baths

2,952

Sq.Ft.

14008 JOMATT LOOP

Winter Garden, FL

Courtesy of THE AGENCY FL
View 8060 BOWERY DRIVE Winter Garden, FL MLS# O6421395
  • Recently Listed with Virtual Tour
1 of 48
$650,000
5

Beds

3.0

Baths

3,013

Sq.Ft.

8060 BOWERY DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS LEGACY REALTY
View 11036 ROBERT FROST DRIVE Winter Garden, FL MLS# O6410350
$649,990
4

Beds

3.0

Baths

2,136

Sq.Ft.

11036 ROBERT FROST DRIVE

Winter Garden, FL

View 16131 HAMPTON CROSSING DRIVE Winter Garden, FL MLS# O6417701
$649,900
4

Beds

3.0

Baths

2,117

Sq.Ft.

16131 HAMPTON CROSSING DRIVE

Winter Garden, FL

View 16622 PARABLE WAY Winter Garden, FL MLS# O6376696
$649,000
4

Beds

3.0

Baths

2,136

Sq.Ft.

16622 PARABLE WAY

Winter Garden, FL

View 15403 MURCOTT HARVEST LOOP Winter Garden, FL MLS# O6386748
$649,000
5

Beds

3.0

Baths

2,834

Sq.Ft.

15403 MURCOTT HARVEST LOOP

Winter Garden, FL

View 921 Westcliffe Drive Winter Garden, FL MLS# B26027811
$649,000
4

Beds

2.1

Baths

2,354

Sq.Ft.

921 Westcliffe Drive

Winter Garden, FL

View 914 TROWMAN ALLEY Winter Garden, FL MLS# O6410871
$649,000
3

Beds

2.1

Baths

1,642

Sq.Ft.

914 TROWMAN ALLEY

Winter Garden, FL

View 12732 SUNSET WALK DRIVE Winter Garden, FL MLS# O6415777
  • New Construction with Virtual Tour
1 of 13
$649,000
4

Beds

4.0

Baths

2,593

Sq.Ft.

12732 SUNSET WALK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 12537 GRAPE CHARDONNAY ALLEY Winter Garden, FL MLS# O6411681
$647,172
3

Beds

3.0

Baths

2,200

Sq.Ft.

12537 GRAPE CHARDONNAY ALLEY

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 17031 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5110934
$646,090
5

Beds

4.0

Baths

2,680

Sq.Ft.

17031 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6587 OLD CARRIAGE ROAD Winter Garden, FL MLS# O6421933
$645,000
3

Beds

2.0

Baths

2,224

Sq.Ft.

6587 OLD CARRIAGE ROAD

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

937

Estimated median home price

$599,990
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 - 100K1
$100K - 200K22
$200K - 300K89
$300K - 400K65
$400K - 500K132
$500K - 600K163
$600K - 700K102
$700K - 800K95
$800K - 900K87
$900K - 1M62
$1M - Max119

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family637
Townhouse130
Condo135
Commercial11
Rental199
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 7/11/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

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.

Data is updated as of 7/12/2026.

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 7/12/2026.