View 16554 POINT ROCK DRIVE Winter Garden, FL MLS# O6295043
$590,000
4

Beds

3.1

Baths

2,474

Sq.Ft.

16554 POINT ROCK DRIVE

Winter Garden, FL

Courtesy of JOHN SILVA REALTY & ASSOCIATES
View 16472 ANGEL FISH ROAD Winter Garden, FL MLS# O6351523
$590,000
4

Beds

3.1

Baths

2,500

Sq.Ft.

16472 ANGEL FISH ROAD

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 17098 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6357599
$590,000
4

Beds

3.1

Baths

2,484

Sq.Ft.

17098 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of ORLANDO BROTHERS REAL ESTATE LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 4122 SHEPPERDS HOLLOW ALLEY Winter Garden, FL MLS# O6370363
  • Recently Listed with Virtual Tour
1 of 44
OPEN HOUSE: Sunday 1/11 2:00 PM - 4:00 PM
$589,900
3

Beds

3.1

Baths

2,459

Sq.Ft.

4122 SHEPPERDS HOLLOW ALLEY

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 10625 ATWATER BAY DRIVE Winter Garden, FL MLS# O6357589
$589,000
4

Beds

3.1

Baths

2,477

Sq.Ft.

10625 ATWATER BAY DRIVE

Winter Garden, FL

Courtesy of HOUWZER INC
View 15929 MOONLIGHT BAY STREET Winter Garden, FL MLS# S5137355
$588,000
4

Beds

3.1

Baths

2,290

Sq.Ft.

15929 MOONLIGHT BAY STREET

Winter Garden, FL

Courtesy of VALSTAR REALTY LLC
View 15008 LEBEAU LOOP Winter Garden, FL MLS# O6364976
$587,990
3

Beds

2.1

Baths

1,972

Sq.Ft.

15008 LEBEAU LOOP

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 6475 BREEZE FILLED LANE Winter Garden, FL MLS# O6351829
$585,000
5

Beds

3.0

Baths

2,231

Sq.Ft.

6475 BREEZE FILLED LANE

Winter Garden, FL

Courtesy of ONLI REALTY GROUP LLC
View 16140 HARBOR MIST ALLEY Winter Garden, FL MLS# O6365057
$585,000
4

Beds

3.1

Baths

2,477

Sq.Ft.

16140 HARBOR MIST ALLEY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 7825 BOSTONIAN DRIVE Winter Garden, FL MLS# O6368837
  • Recently Listed with Virtual Tour
1 of 54
$585,000
3

Beds

2.0

Baths

2,270

Sq.Ft.

7825 BOSTONIAN DRIVE

Winter Garden, FL

Courtesy of GENSTONE REALTY
View Address not provided Winter Garden, FL MLS# G5099741
  • New Construction
1 of 62
$584,990
3

Beds

3.0

Baths

2,083

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15107 KIRSTY ALLEY Winter Garden, FL MLS# O6360875
  • Virtual Tour
1 of 24
$584,800
4

Beds

2.1

Baths

2,292

Sq.Ft.

15107 KIRSTY ALLEY

Winter Garden, FL

Courtesy of KAZA REAL ESTATE LLC
View 16602 POINT ROCK DRIVE Winter Garden, FL MLS# O6348038
$584,500
4

Beds

3.1

Baths

2,474

Sq.Ft.

16602 POINT ROCK DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 16833 HOBE SOUND COURT Winter Garden, FL MLS# O6367151
  • New Construction with Virtual Tour
1 of 7
$581,190
3

Beds

2.1

Baths

2,216

Sq.Ft.

16833 HOBE SOUND COURT

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 7500 LAKE HANCOCK BOULEVARD Winter Garden, FL MLS# O6327015
$580,000
3

Beds

2.0

Baths

2,270

Sq.Ft.

7500 LAKE HANCOCK BOULEVARD

Winter Garden, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 15433 PORTER ROAD Winter Garden, FL MLS# O6346995
  • Virtual Tour
1 of 46
OPEN HOUSE: Thursday 1/8 12:00 PM - 2:00 PM
$580,000
5

Beds

3.0

Baths

2,455

Sq.Ft.

15433 PORTER ROAD

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 15607 CAMP DUBOIS CRESCENT Winter Garden, FL MLS# O6360056
$580,000
4

Beds

3.1

Baths

2,818

Sq.Ft.

15607 CAMP DUBOIS CRESCENT

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 102 VALENCIA SHORES DRIVE Winter Garden, FL MLS# G5103373
$579,900
3

Beds

2.0

Baths

1,910

Sq.Ft.

102 VALENCIA SHORES DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER HUBBARD HANSEN
View 6345 WILD PERSIMMON WAY Winter Garden, FL MLS# G5102273
  • New Construction
1 of 2
$579,285
3

Beds

2.0

Baths

1,772

Sq.Ft.

6345 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 9263 QUEST ALLEY ALLEY Winter Garden, FL MLS# O6342586
$579,000
4

Beds

3.1

Baths

2,500

Sq.Ft.

9263 QUEST ALLEY ALLEY

Winter Garden, FL

Courtesy of UNITED REAL ESTATE PREFERRED

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

763

Estimated median home price

$585,000
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

Price Count
$0 - 100K 6
$100K - 200K 10
$200K - 300K 64
$300K - 400K 80
$400K - 500K 135
$500K - 600K 115
$600K - 700K 82
$700K - 800K 70
$800K - 900K 62
$900K - 1M 48
$1M - Max 91

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 491
Townhouse 119
Condo 107
Commercial 9
Rental 223
Lots and Land 33
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 1
Farms 0

(Data as of 1/6/2026)

Information deemed reliable but not guaranteed.

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 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

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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 1/7/2026.

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 1/7/2026.