Winter Garden Florida Homes for Rent

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View 6168 GLORY BOWER DRIVE Winter Garden, FL MLS# O6437622
$2,800
3

Beds

2.1

Baths

2,138

Sq.Ft.

6168 GLORY BOWER DRIVE

Winter Garden, FL

View 11018 SILVER SURFER ALLEY Winter Garden, FL MLS# O6437653
$2,850
3

Beds

2.1

Baths

2,124

Sq.Ft.

11018 SILVER SURFER ALLEY

Winter Garden, FL

View 15030 EVERGREEN OAK LOOP Winter Garden, FL MLS# O6437349
  • Recently Listed with Virtual Tour
1 of 49
$3,400
4

Beds

3.1

Baths

2,570

Sq.Ft.

15030 EVERGREEN OAK LOOP

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 17819 TWISTED MANDARIN ALLEY Winter Garden, FL MLS# O6435914
  • Recently Listed with Virtual Tour
1 of 27
$3,300
3

Beds

2.1

Baths

2,134

Sq.Ft.

17819 TWISTED MANDARIN ALLEY

Winter Garden, FL

View 467 WINTER GROVE BOULEVARD Winter Garden, FL MLS# S5156515
  • Recently Listed with Virtual Tour
1 of 48
$4,995
5

Beds

3.1

Baths

3,643

Sq.Ft.

467 WINTER GROVE BOULEVARD

Winter Garden, FL

Courtesy of NEWKEY REAL ESTATE LLC
View 218 WINTER NELLIS CIRCLE Winter Garden, FL MLS# O6436614
  • Recently Listed with Virtual Tour
1 of 38
$2,295
3

Beds

2.1

Baths

1,647

Sq.Ft.

218 WINTER NELLIS CIRCLE

Winter Garden, FL

View 15045 GROVESIDE ROAD Winter Garden, FL MLS# S5156528
  • Recently Listed with Virtual Tour
1 of 45
$3,350
4

Beds

3.1

Baths

1,846

Sq.Ft.

15045 GROVESIDE ROAD

Winter Garden, FL

Courtesy of NEWKEY REAL ESTATE LLC
View 200 SOUTHERN PECAN CIRCLE 206 Winter Garden, FL MLS# O6437594
  • Recently Listed with Virtual Tour
1 of 53
$1,850
2

Beds

2.0

Baths

1,276

Sq.Ft.

200 SOUTHERN PECAN CIRCLE 206

Winter Garden, FL

View 1841 EAGLE BEAM ROAD Winter Garden, FL MLS# O6437392
  • Recently Listed with Virtual Tour
1 of 18
$2,500
3

Beds

2.1

Baths

1,342

Sq.Ft.

1841 EAGLE BEAM ROAD

Winter Garden, FL

View 14537 GOLDEN HARBOR LANE Winter Garden, FL MLS# S5156226
  • Recently Listed with Virtual Tour
1 of 19
$2,850
4

Beds

2.1

Baths

1,868

Sq.Ft.

14537 GOLDEN HARBOR LANE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 7840 MINUTEMEN LOOP Winter Garden, FL MLS# O6436819
  • Recently Listed with Virtual Tour
1 of 28
$2,975
3

Beds

2.0

Baths

2,278

Sq.Ft.

7840 MINUTEMEN LOOP

Winter Garden, FL

Courtesy of TRUSTHOME PROPERTIES INC
View 1007 CAROL ANDERSON DRIVE Winter Garden, FL MLS# S5156254
  • Recently Listed with Virtual Tour
1 of 10
$2,250
4

Beds

2.0

Baths

1,300

Sq.Ft.

1007 CAROL ANDERSON DRIVE

Winter Garden, FL

View 15517 BAY BRIDGE STREET Winter Garden, FL MLS# O6436419
  • Recently Listed with Virtual Tour
1 of 28
$2,900
3

Beds

2.1

Baths

1,691

Sq.Ft.

15517 BAY BRIDGE STREET

Winter Garden, FL

View 960 CHASE COURT Winter Garden, FL MLS# O6436480
  • Recently Listed with Virtual Tour
1 of 16
$3,000
5

Beds

2.1

Baths

2,981

Sq.Ft.

960 CHASE COURT

Winter Garden, FL

View 7036 BOLANZO ALLEY Winter Garden, FL MLS# O6436508
  • Recently Listed with Virtual Tour
1 of 16
$3,000
4

Beds

3.1

Baths

1,920

Sq.Ft.

7036 BOLANZO ALLEY

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 13193 CALMING BREEZE WAY Winter Garden, FL MLS# S5156370
  • Recently Listed with Virtual Tour
1 of 21
$2,700
3

Beds

2.1

Baths

1,644

Sq.Ft.

13193 CALMING BREEZE WAY

Winter Garden, FL

View 4753 TERRACE BLUFF STREET Winter Garden, FL MLS# O6436376
$3,950
4

Beds

4.1

Baths

2,817

Sq.Ft.

4753 TERRACE BLUFF STREET

Winter Garden, FL

View 16237 QUIET VISTA DRIVE Winter Garden, FL MLS# O6436637
  • Recently Listed with Virtual Tour
1 of 19
$2,550
3

Beds

2.1

Baths

1,568

Sq.Ft.

16237 QUIET VISTA DRIVE

Winter Garden, FL

View 15607 PORTER ROAD Winter Garden, FL MLS# S5155368
  • Recently Listed with Virtual Tour
1 of 42
$3,295
4

Beds

2.1

Baths

2,727

Sq.Ft.

15607 PORTER ROAD

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 17951 DANGLER ROAD Winter Garden, FL MLS# O6434145
  • Recently Listed with Virtual Tour
1 of 34
$4,500
4

Beds

3.0

Baths

1,693

Sq.Ft.

17951 DANGLER ROAD

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

1,029

Estimated median home price

$608,000
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

PriceCount
$0 - 100K1
$100K - 200K22
$200K - 300K89
$300K - 400K78
$400K - 500K153
$500K - 600K168
$600K - 700K112
$700K - 800K113
$800K - 900K112
$900K - 1M62
$1M - Max119

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family715
Townhouse145
Condo133
Commercial9
Rental188
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/29/2026)

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 8/29/2026.