View 15568 BLACKBEAD STREET Winter Garden, FL MLS# O6408861
$448,000
4

Beds

3.0

Baths

1,861

Sq.Ft.

15568 BLACKBEAD STREET

Winter Garden, FL

Courtesy of MARK SPAIN REAL ESTATE
View 9652 AMBER CHESTNUT WAY Winter Garden, FL MLS# O6409704
  • Recently Listed with Virtual Tour
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 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

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 15591 HONEYBELL DRIVE Winter Garden, FL MLS# O6408635
  • Recently Listed with Virtual Tour
1 of 48
$389,900
3

Beds

2.1

Baths

1,584

Sq.Ft.

15591 HONEYBELL DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 16564 BARBOURS CREEK WAY Winter Garden, FL MLS# O6408256
  • New Construction with Virtual Tour
1 of 18
$459,990
3

Beds

2.1

Baths

1,817

Sq.Ft.

16564 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 14501 GROVE RESORT AVE 1535 1535 Winter Garden, FL MLS# S5150001
  • Recently Listed with Virtual Tour
1 of 19
$410,990
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVE 1535 1535

Winter Garden, FL

Courtesy of SACKS REALTY GROUP, INC.
View 342 WINDFORD COURT Winter Garden, FL MLS# O6407632
  • Recently Listed with Virtual Tour
1 of 17
$349,900
3

Beds

2.0

Baths

1,194

Sq.Ft.

342 WINDFORD COURT

Winter Garden, FL

Courtesy of RE/MAX 200 REALTY
View 14002 AVENUE OF THE GROVES Winter Garden, FL MLS# S5149866
  • Recently Listed with Virtual Tour
1 of 38
$345,000
2

Beds

2.1

Baths

1,271

Sq.Ft.

14002 AVENUE OF THE GROVES

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 15615 HONEYBELL DRIVE Winter Garden, FL MLS# O6406267
  • Recently Listed with Virtual Tour
1 of 37
$389,900
3

Beds

2.1

Baths

1,584

Sq.Ft.

15615 HONEYBELL DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 14501 Grove Resort 1304 Winter Garden, FL MLS# A12022081
  • Recently Listed with Virtual Tour
1 of 57
$350,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 Grove Resort 1304

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 11072 SILVER SURFER ALLEY Winter Garden, FL MLS# O6406656
  • Recently Listed with Virtual Tour
1 of 33
$460,000
3

Beds

2.1

Baths

1,770

Sq.Ft.

11072 SILVER SURFER ALLEY

Winter Garden, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 13299 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5112134
  • Recently Listed with Virtual Tour
1 of 26
$449,990
3

Beds

2.1

Baths

1,729

Sq.Ft.

13299 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
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 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 833 BENDING OAK TRAIL Winter Garden, FL MLS# O6403683
  • Recently Listed with Virtual Tour
1 of 31
OPEN HOUSE: Thursday 5/21 5:00 PM - 7:00 PM
$399,000
3

Beds

2.1

Baths

1,789

Sq.Ft.

833 BENDING OAK TRAIL

Winter Garden, FL

Courtesy of GLOBAL FLORIDA REALTY
View 10294 MERRYMEETING BAY DRIVE Winter Garden, FL MLS# O6407798
  • Recently Listed with Virtual Tour
1 of 58
$468,900
3

Beds

2.0

Baths

1,689

Sq.Ft.

10294 MERRYMEETING BAY DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 17025 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5112007
$456,554
3

Beds

2.1

Baths

1,697

Sq.Ft.

17025 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17736 PORTER ROAD Winter Garden, FL MLS# G5112009
  • New Construction with Virtual Tour
1 of 25
$451,542
3

Beds

3.0

Baths

1,715

Sq.Ft.

17736 PORTER ROAD

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
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 15140 WINDFLOWER ALLEY Winter Garden, FL MLS# S5149180
  • Recently Listed with Virtual Tour
1 of 34
$410,000
3

Beds

2.1

Baths

1,536

Sq.Ft.

15140 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of LIFESTYLE INTERNATIONAL REALTY

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

1,037

Estimated median home price

$609,990
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 - 300K100
$300K - 400K80
$400K - 500K140
$500K - 600K165
$600K - 700K128
$700K - 800K120
$800K - 900K85
$900K - 1M76
$1M - Max120

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family712
Townhouse139
Condo144
Commercial10
Rental214
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 5/20/2026)

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 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 5/21/2026.

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 5/21/2026.