View 2040 PORTCASTLE CIRCLE Winter Garden, FL MLS# O6397668
  • Recently Listed with Virtual Tour
1 of 18
$2,495
4

Beds

2.1

Baths

1,606

Sq.Ft.

2040 PORTCASTLE CIRCLE

Winter Garden, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 9906 SUNNY MEWS ALLEY Winter Garden, FL MLS# S5147715
  • Recently Listed with Virtual Tour
1 of 12
$2,800
3

Beds

2.1

Baths

1,654

Sq.Ft.

9906 SUNNY MEWS ALLEY

Winter Garden, FL

Courtesy of MBT REALTY LLC
View 9469 MEADOW HUNT WAY Winter Garden, FL MLS# O6398645
  • Recently Listed with Virtual Tour
1 of 34
$2,800
4

Beds

2.1

Baths

1,868

Sq.Ft.

9469 MEADOW HUNT WAY

Winter Garden, FL

Courtesy of HANG SENG REALTY , INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 13170 BOUNTY AVENUE Winter Garden, FL MLS# O6398807
  • Recently Listed with Virtual Tour
1 of 23
$2,550
3

Beds

2.1

Baths

1,568

Sq.Ft.

13170 BOUNTY AVENUE

Winter Garden, FL

Courtesy of MAY HO REALTY
View 7007 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6398823
  • Recently Listed with Virtual Tour
1 of 20
$2,700
3

Beds

2.1

Baths

1,845

Sq.Ft.

7007 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 6148 WATERSIDE ISLAND LANE Winter Garden, FL MLS# O6398414
  • Recently Listed with Virtual Tour
1 of 20
$3,500
5

Beds

3.1

Baths

3,468

Sq.Ft.

6148 WATERSIDE ISLAND LANE

Winter Garden, FL

Courtesy of JHY REALTY INVESTMENTS, LLC
View Address not provided Winter Garden, FL MLS# O6398448
  • Recently Listed with Virtual Tour
1 of 57
$3,400
4

Beds

3.1

Baths

2,570

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of ORLANDO SUNSHINE REALTY
View 215 CENTER STREET 225/227 Winter Garden, FL MLS# O6398301
  • Recently Listed with Virtual Tour
1 of 19
$32,400
2,304

Sq.Ft.

215 CENTER STREET 225/227

Winter Garden, FL

Courtesy of PREICO REALTY SERVICES INC
View 7564 BISHOP SQUARE DRIVE Winter Garden, FL MLS# O6398382
  • Recently Listed with Virtual Tour
1 of 70
$3,999
3

Beds

2.0

Baths

2,300

Sq.Ft.

7564 BISHOP SQUARE DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 530 SETTING SUN DRIVE Winter Garden, FL MLS# O6398374
  • Recently Listed
1 of 32
$3,450
3

Beds

2.0

Baths

2,365

Sq.Ft.

530 SETTING SUN DRIVE

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
View 1221 PRIORY CIRCLE Winter Garden, FL MLS# O6397929
  • Recently Listed with Virtual Tour
1 of 12
$2,800
3

Beds

2.1

Baths

1,675

Sq.Ft.

1221 PRIORY CIRCLE

Winter Garden, FL

Courtesy of ROMAN'S PRO REALTY LLC
View 15542 GWINNETT DRIVE Winter Garden, FL MLS# O6397981
  • Recently Listed with Virtual Tour
1 of 26
$3,700
4

Beds

3.1

Baths

2,879

Sq.Ft.

15542 GWINNETT DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 10247 LOVE STORY STREET Winter Garden, FL MLS# O6397731
  • Recently Listed with Virtual Tour
1 of 37
$3,100
4

Beds

3.1

Baths

2,502

Sq.Ft.

10247 LOVE STORY STREET

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 13323 PONTOON ROAD Winter Garden, FL MLS# S5147574
  • Recently Listed with Virtual Tour
1 of 26
$2,750
3

Beds

2.1

Baths

1,451

Sq.Ft.

13323 PONTOON ROAD

Winter Garden, FL

Courtesy of LA ROSA REALTY INTERNACIONAL L
View 16743 HERONGATE DRIVE Winter Garden, FL MLS# O6397844
  • Recently Listed with Virtual Tour
1 of 39
$2,950
3

Beds

2.0

Baths

1,705

Sq.Ft.

16743 HERONGATE DRIVE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 16374 TURNING TIDE WAY Winter Garden, FL MLS# O6397885
  • Recently Listed
1 of 28
$2,650
3

Beds

2.1

Baths

1,568

Sq.Ft.

16374 TURNING TIDE WAY

Winter Garden, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View Address not provided Winter Garden, FL MLS# O6396812
  • Recently Listed with Virtual Tour
1 of 26
$3,000
4

Beds

3.0

Baths

2,286

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 15713 SWEET LIMETTA DRIVE Winter Garden, FL MLS# O6397517
$5,000
4

Beds

4.1

Baths

3,377

Sq.Ft.

15713 SWEET LIMETTA DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 15512 SUNQUAT DRIVE Winter Garden, FL MLS# O6397578
  • Recently Listed with Virtual Tour
1 of 40
$4,490
3

Beds

2.0

Baths

1,979

Sq.Ft.

15512 SUNQUAT DRIVE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 15367 GILLIGAN COURT Winter Garden, FL MLS# O6397119
  • Recently Listed with Virtual Tour
1 of 30
$3,500
4

Beds

2.1

Baths

2,156

Sq.Ft.

15367 GILLIGAN COURT

Winter Garden, FL

Courtesy of PAK HOME 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

959

Estimated median home price

$591,000
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 1
$100K - 200K 19
$200K - 300K 95
$300K - 400K 79
$400K - 500K 147
$500K - 600K 157
$600K - 700K 115
$700K - 800K 97
$800K - 900K 82
$900K - 1M 64
$1M - Max 103

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 659
Townhouse 135
Condo 128
Commercial 12
Rental 228
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 4/13/2026)

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

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 4/14/2026.