View 15381 AVENUE OF THE ARBORS Winter Garden, FL MLS# O6426190
  • Recently Listed with Virtual Tour
1 of 32
$2,800
4

Beds

2.1

Baths

1,999

Sq.Ft.

15381 AVENUE OF THE ARBORS

Winter Garden, FL

View 14075 FRASIER STREET Winter Garden, FL MLS# S5117084
  • New Construction with Virtual Tour
1 of 14
$2,799
4

Beds

2.1

Baths

2,082

Sq.Ft.

14075 FRASIER STREET

Winter Garden, FL

Courtesy of JASON MITCHELL REAL ESTATE FLO
View 1335 PRIORY CIRCLE Winter Garden, FL MLS# O6388888
$2,790
3

Beds

2.1

Baths

1,898

Sq.Ft.

1335 PRIORY CIRCLE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1519 PRIORY CIRCLE Winter Garden, FL MLS# O6382465
$2,775
3

Beds

2.1

Baths

1,956

Sq.Ft.

1519 PRIORY CIRCLE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 13881 EASDALE ALLEY Winter Garden, FL MLS# O6413642
$2,750
3

Beds

2.1

Baths

1,996

Sq.Ft.

13881 EASDALE ALLEY

Winter Garden, FL

Courtesy of LOVELAND PROPERTIES
View 16525 OUTTER GROVE ALLEY Winter Garden, FL MLS# O6421516
  • Recently Listed with Virtual Tour
1 of 17
$2,750
3

Beds

2.1

Baths

1,814

Sq.Ft.

16525 OUTTER GROVE ALLEY

Winter Garden, FL

View 7387 MEZZANO LANE DRIVE Winter Garden, FL MLS# O6424792
  • Recently Listed with Virtual Tour
1 of 19
$2,750
3

Beds

2.1

Baths

1,843

Sq.Ft.

7387 MEZZANO LANE DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 15467 SUGAR CITRUS DRIVE Winter Garden, FL MLS# S5121940
$2,700
4

Beds

3.0

Baths

1,853

Sq.Ft.

15467 SUGAR CITRUS DRIVE

Winter Garden, FL

View 17061 WATER SPRING BOULEVARD Winter Garden, FL MLS# O6304776
$2,700
3

Beds

2.1

Baths

1,568

Sq.Ft.

17061 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 13193 CALMING BREEZE WAY Winter Garden, FL MLS# S5151579
$2,700
3

Beds

2.1

Baths

1,644

Sq.Ft.

13193 CALMING BREEZE WAY

Winter Garden, FL

Courtesy of MELIN REALTY LLC
View 17332 SWEET MORO DRIVE Winter Garden, FL MLS# S5151783
  • New Construction with Virtual Tour
1 of 47
$2,700
3

Beds

2.1

Baths

1,624

Sq.Ft.

17332 SWEET MORO DRIVE

Winter Garden, FL

View 17344 SWEET MORO DRIVE Winter Garden, FL MLS# O6418154
$2,700
3

Beds

2.1

Baths

1,584

Sq.Ft.

17344 SWEET MORO DRIVE

Winter Garden, FL

View 1944 PORTCASTLE CIRCLE Winter Garden, FL MLS# O6421978
$2,700
3

Beds

2.1

Baths

1,857

Sq.Ft.

1944 PORTCASTLE CIRCLE

Winter Garden, FL

View 13286 PONTOON RD Winter Garden, FL MLS# S5153099
  • Recently Listed
1 of 6
$2,700
3

Beds

2.1

Baths

1,568

Sq.Ft.

13286 PONTOON RD

Winter Garden, FL

View 10738 RHETT BUTLER ALLEY Winter Garden, FL MLS# S5153938
  • Recently Listed with Virtual Tour
1 of 36
$2,700
3

Beds

2.1

Baths

1,636

Sq.Ft.

10738 RHETT BUTLER ALLEY

Winter Garden, FL

View 11193 HANLON TERRACE ALLEY Winter Garden, FL MLS# O6426402
  • Recently Listed with Virtual Tour
1 of 51
$2,700
3

Beds

2.1

Baths

1,868

Sq.Ft.

11193 HANLON TERRACE ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS LEGACY REALTY
View 6561 CALAMONDIN DRIVE Winter Garden, FL MLS# O6414224
$2,695
3

Beds

2.1

Baths

1,609

Sq.Ft.

6561 CALAMONDIN DRIVE

Winter Garden, FL

View 1631 SHERBOURNE STREET Winter Garden, FL MLS# O6422395
  • Recently Listed with Virtual Tour
1 of 21
$2,680
4

Beds

2.1

Baths

1,709

Sq.Ft.

1631 SHERBOURNE STREET

Winter Garden, FL

Courtesy of YORK MILLS REALTY LLC
View 224 FAULKNER STREET Winter Garden, FL MLS# O6411344
$2,665
3

Beds

2.0

Baths

1,591

Sq.Ft.

224 FAULKNER STREET

Winter Garden, FL

View 13071 INKWELL ALLEY Winter Garden, FL MLS# S5148709
$2,650
4

Beds

3.0

Baths

2,042

Sq.Ft.

13071 INKWELL ALLEY

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

951

Estimated median home price

$611,610
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 - 300K93
$300K - 400K61
$400K - 500K129
$500K - 600K161
$600K - 700K99
$700K - 800K113
$800K - 900K92
$900K - 1M63
$1M - Max117

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family654
Townhouse126
Condo138
Commercial11
Rental210
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/19/2026)

Information deemed reliable but not guaranteed.

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 7/19/2026.