View 9652 AMBER CHESTNUT WAY Winter Garden, FL MLS# O6409704
  • Recently Listed
1 of 43
$445,000
4

Beds

2.1

Baths

1,948

Sq.Ft.

9652 AMBER CHESTNUT WAY

Winter Garden, FL

Courtesy of PRATT REALTY INC
View 16353 LAKELET ALLEY Winter Garden, FL MLS# O6316011
  • New Construction with Virtual Tour
1 of 32
$444,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16353 LAKELET ALLEY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 8113 RED STOPPER LANE Winter Garden, FL MLS# O6386525
$444,000
3

Beds

2.1

Baths

1,725

Sq.Ft.

8113 RED STOPPER LANE

Winter Garden, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 15907 MARINA BAY DRIVE Winter Garden, FL MLS# O6398406
$443,500
3

Beds

2.1

Baths

1,818

Sq.Ft.

15907 MARINA BAY DRIVE

Winter Garden, FL

Courtesy of SIMPSON REALTY LLC
View 15038 WINDFLOWER ALLEY Winter Garden, FL MLS# O6405201
  • Recently Listed with Virtual Tour
1 of 10
$441,000
3

Beds

2.1

Baths

1,536

Sq.Ft.

15038 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of DTB FLORIDA REALTY, INC.
View 17109 Water Spring BOULEVARD Winter Garden, FL MLS# O6192649
$440,000
3

Beds

2.1

Baths

1,568

Sq.Ft.

17109 Water Spring BOULEVARD

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 14095 TITLE WAY Winter Garden, FL MLS# O6382795
  • Virtual Tour
1 of 38
$440,000
3

Beds

2.1

Baths

1,628

Sq.Ft.

14095 TITLE WAY

Winter Garden, FL

Courtesy of ROMAN'S PRO REALTY LLC
View 16570 BARBOURS CREEK WAY Winter Garden, FL MLS# O6403257
  • New Construction with Virtual Tour
1 of 15
$439,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16570 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 13339 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5111849
  • New Construction with Virtual Tour
1 of 26
$439,990
3

Beds

2.1

Baths

1,729

Sq.Ft.

13339 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13295 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5112136
  • Recently Listed with Virtual Tour
1 of 25
$439,990
3

Beds

2.1

Baths

1,715

Sq.Ft.

13295 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6143 Elfin Herb WAY Winter Garden, FL MLS# O6191255
$438,900
3

Beds

2.1

Baths

1,560

Sq.Ft.

6143 Elfin Herb WAY

Winter Garden, FL

Courtesy of THE PROPERTY PROS REAL ESTATE, INC
View 13946 TITLE WAY Winter Garden, FL MLS# O6384098
  • Virtual Tour
1 of 44
$438,000
4

Beds

2.1

Baths

1,992

Sq.Ft.

13946 TITLE WAY

Winter Garden, FL

Courtesy of RC GROUP REALTY LLC
View 13307 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5112135
  • Recently Listed with Virtual Tour
1 of 53
$437,990
3

Beds

2.1

Baths

1,644

Sq.Ft.

13307 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14501 GROVE RESORT AVENUE 1535 Winter Garden, FL MLS# TB8447837
$435,999
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 1535

Winter Garden, FL

Courtesy of BY OWNER.COM
View 16425 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6383709
$435,000
3

Beds

2.1

Baths

1,662

Sq.Ft.

16425 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 1836 WINGED ELM PLACE Winter Garden, FL MLS# O6390771
$435,000
4

Beds

2.0

Baths

1,712

Sq.Ft.

1836 WINGED ELM PLACE

Winter Garden, FL

Courtesy of MARK SPAIN REAL ESTATE
View 15659 JUNGLE ALLEY Winter Garden, FL MLS# S5143684
  • Virtual Tour
1 of 16
$435,000
3

Beds

2.1

Baths

1,732

Sq.Ft.

15659 JUNGLE ALLEY

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 16413 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6397513
  • Virtual Tour
1 of 36
OPEN HOUSE: Saturday 5/23 1:00 PM - 4:00 PM
$434,900
3

Beds

2.1

Baths

1,626

Sq.Ft.

16413 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 15508 BLACKBEAD STREET Winter Garden, FL MLS# O6371455
$430,000
3

Beds

2.1

Baths

1,754

Sq.Ft.

15508 BLACKBEAD STREET

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 15334 MURCOTT BLOSSOM BOULEVARD Winter Garden, FL MLS# O6392207
$430,000
3

Beds

2.1

Baths

1,868

Sq.Ft.

15334 MURCOTT BLOSSOM BOULEVARD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE

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

1,050

Estimated median home price

$609,945
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 2
$100K - 200K 22
$200K - 300K 100
$300K - 400K 81
$400K - 500K 142
$500K - 600K 169
$600K - 700K 128
$700K - 800K 120
$800K - 900K 86
$900K - 1M 75
$1M - Max 125

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 722
Townhouse 141
Condo 146
Commercial 10
Rental 214
Lots and Land 28
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 2
Farms 0

(Data as of 5/22/2026)

Information deemed reliable but not guaranteed.

Copyright 2026 BeachesMLS, Inc. All rights reserved.

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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 5/23/2026.

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 5/23/2026.