View 15340 OAK APPLE COURT COURT 16B Winter Garden, FL MLS# O6419809
  • Recently Listed with Virtual Tour
1 of 42
$350,000
3

Beds

2.1

Baths

1,544

Sq.Ft.

15340 OAK APPLE COURT COURT 16B

Winter Garden, FL

View 16594 BARBOURS CREEK WAY Winter Garden, FL MLS# O6420082
  • New Construction with Virtual Tour
1 of 67
$440,000
3

Beds

2.1

Baths

1,817

Sq.Ft.

16594 BARBOURS CREEK WAY

Winter Garden, FL

View 16509 BARBOURS CREEK WAY Winter Garden, FL MLS# O6420095
  • Recently Listed with Virtual Tour
1 of 63
$447,500
3

Beds

2.1

Baths

1,567

Sq.Ft.

16509 BARBOURS CREEK WAY

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 5863 CYPRESS HILL ROAD Winter Garden, FL MLS# TB8522840
  • Recently Listed with Virtual Tour
1 of 11
$390,000
2

Beds

2.1

Baths

1,594

Sq.Ft.

5863 CYPRESS HILL ROAD

Winter Garden, FL

View 14501 GROVE RESORT AVENUE 3227 Winter Garden, FL MLS# S5152479
  • Recently Listed with Virtual Tour
1 of 43
$365,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 3227

Winter Garden, FL

View 217 W STORY ROAD Winter Garden, FL MLS# O6417750
  • Recently Listed
1 of 27
$450,000
3

Beds

2.0

Baths

1,120

Sq.Ft.

217 W STORY ROAD

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 721 S WOODLAND STREET Winter Garden, FL MLS# O6419636
  • Recently Listed with Virtual Tour
1 of 24
$450,000
2

Beds

1.0

Baths

1,034

Sq.Ft.

721 S WOODLAND STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 1610 BEULAH ROAD Winter Garden, FL MLS# O6418153
  • Recently Listed with Virtual Tour
1 of 43
$450,000
4

Beds

2.0

Baths

2,210

Sq.Ft.

1610 BEULAH ROAD

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 12042 GRANDROSE ALLEY Winter Garden, FL MLS# S5152170
  • Recently Listed with Virtual Tour
1 of 21
$420,000
3

Beds

2.1

Baths

1,732

Sq.Ft.

12042 GRANDROSE ALLEY

Winter Garden, FL

View 15524 HONEYBELL DRIVE Winter Garden, FL MLS# O6416374
  • Recently Listed with Virtual Tour
1 of 43
$419,000
4

Beds

3.0

Baths

1,902

Sq.Ft.

15524 HONEYBELL DRIVE

Winter Garden, FL

View 1645 E SPRING RIDGE CIRCLE Winter Garden, FL MLS# O6416732
  • Recently Listed with Virtual Tour
1 of 42
$450,000
3

Beds

2.0

Baths

1,219

Sq.Ft.

1645 E SPRING RIDGE CIRCLE

Winter Garden, FL

Courtesy of PREFERRED RE BROKERS III
View 13303 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5113612
  • New Construction with Virtual Tour
1 of 25
$424,990
3

Beds

2.1

Baths

1,715

Sq.Ft.

13303 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14903 DRIFTWATER DRIVE Winter Garden, FL MLS# S5151359
  • Recently Listed with Virtual Tour
1 of 59
$380,000
3

Beds

2.1

Baths

1,745

Sq.Ft.

14903 DRIFTWATER DRIVE

Winter Garden, FL

View 5686 CYPRESS HILL ROAD Winter Garden, FL MLS# O6410760
$422,000
3

Beds

2.1

Baths

1,712

Sq.Ft.

5686 CYPRESS HILL ROAD

Winter Garden, FL

View 6131 ELFIN HERB WAY Winter Garden, FL MLS# O6414015
  • Recently Listed with Virtual Tour
1 of 36
$450,000
3

Beds

2.1

Baths

1,714

Sq.Ft.

6131 ELFIN HERB WAY

Winter Garden, FL

View 16461 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6414427
  • Recently Listed with Virtual Tour
1 of 59
$415,000
4

Beds

2.1

Baths

1,768

Sq.Ft.

16461 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

View 15511 CAMPDEN STREET Winter Garden, FL MLS# O6413461
$395,000
3

Beds

2.1

Baths

1,916

Sq.Ft.

15511 CAMPDEN STREET

Winter Garden, FL

Courtesy of SUSANA JORDAN STUTSMAN
View 2123 PORTCASTLE CIRCLE Winter Garden, FL MLS# O6412643
$389,000
4

Beds

2.1

Baths

1,606

Sq.Ft.

2123 PORTCASTLE CIRCLE

Winter Garden, FL

View 420 E CYPRESS STREET Winter Garden, FL MLS# O6412414
$420,000
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
$419,900
3

Beds

2.1

Baths

1,636

Sq.Ft.

11025 SUSPENSE DRIVE

Winter Garden, FL

Courtesy of SCATES REALTY & INVESTMENT PRO

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

1,098

Estimated median home price

$613,305
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 - 200K24
$200K - 300K91
$300K - 400K81
$400K - 500K153
$500K - 600K189
$600K - 700K126
$700K - 800K118
$800K - 900K103
$900K - 1M78
$1M - Max134

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family771
Townhouse146
Condo142
Commercial11
Rental211
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 6/26/2026)

Information deemed reliable but not guaranteed.

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 6/26/2026.

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 6/26/2026.