Winter Garden Florida Homes for Rent

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View 8056 JOHN HANCOCK DRIVE Winter Garden, FL MLS# O6399522
  • Recently Listed with Virtual Tour
1 of 33
$3,195
3

Beds

2.1

Baths

2,199

Sq.Ft.

8056 JOHN HANCOCK DRIVE

Winter Garden, FL

Courtesy of BAHIA INTERNATIONAL REALTY
View 14971 APOLLO BOND DRIVE Winter Garden, FL MLS# O6399621
  • Recently Listed with Virtual Tour
1 of 46
$2,550
3

Beds

2.1

Baths

1,655

Sq.Ft.

14971 APOLLO BOND DRIVE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 16942 TRADEWIND POINT Winter Garden, FL MLS# O6399808
  • Recently Listed with Virtual Tour
1 of 23
$2,500
3

Beds

2.0

Baths

1,692

Sq.Ft.

16942 TRADEWIND POINT

Winter Garden, FL

Courtesy of PARK PLACE REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 11153 GREEN CITRON ALLEY Winter Garden, FL MLS# O6399918
  • Recently Listed with Virtual Tour
1 of 22
$3,350
3

Beds

2.1

Baths

2,091

Sq.Ft.

11153 GREEN CITRON ALLEY

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 12548 ENCORE AT OVATION WAY Winter Garden, FL MLS# S5147778
  • Recently Listed with Virtual Tour
1 of 10
$2,950
3

Beds

2.1

Baths

1,994

Sq.Ft.

12548 ENCORE AT OVATION WAY

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
View 16067 PEBBLE BLUFF LOOP Winter Garden, FL MLS# S5147791
  • Recently Listed with Virtual Tour
1 of 45
$3,000
3

Beds

2.1

Baths

2,012

Sq.Ft.

16067 PEBBLE BLUFF LOOP

Winter Garden, FL

Courtesy of ACKLEY FLORIDA PROPERTY MANAGEMENT INC
View 149 S PARK AVENUE Winter Garden, FL MLS# O6397983
  • Recently Listed with Virtual Tour
1 of 20
$5,200
3

Beds

2.1

Baths

2,938

Sq.Ft.

149 S PARK AVENUE

Winter Garden, FL

Courtesy of GECKO REALTY, INC
View 456 SILVERDALE AVENUE Winter Garden, FL MLS# O6398638
  • Recently Listed
1 of 31
$3,100
4

Beds

2.0

Baths

1,844

Sq.Ft.

456 SILVERDALE AVENUE

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
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
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 595 9TH STREET Winter Garden, FL MLS# O6398340
  • Recently Listed with Virtual Tour
1 of 17
$34,800
1,204

Sq.Ft.

595 9TH STREET

Winter Garden, FL

Courtesy of ENGEL & VOELKERS LAKELAND
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

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

974

Estimated median home price

$599,900
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 80
$400K - 500K 148
$500K - 600K 152
$600K - 700K 119
$700K - 800K 100
$800K - 900K 88
$900K - 1M 65
$1M - Max 107

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 673
Townhouse 134
Condo 129
Commercial 12
Rental 231
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 4/16/2026)

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 4/17/2026.