View 14629 BAHAMA SWALLOW BOULEVARD Winter Garden, FL MLS# O6421797
  • Recently Listed with Virtual Tour
1 of 25
$484,900
3

Beds

2.0

Baths

2,223

Sq.Ft.

14629 BAHAMA SWALLOW BOULEVARD

Winter Garden, FL

View 6843 POINT HANCOCK DRIVE Winter Garden, FL MLS# G5114589
$435,000
3

Beds

2.0

Baths

1,720

Sq.Ft.

6843 POINT HANCOCK DRIVE

Winter Garden, FL

View 7467 JOHN HANCOCK DRIVE Winter Garden, FL MLS# O6421848
$1,350,000
4

Beds

3.1

Baths

3,964

Sq.Ft.

7467 JOHN HANCOCK DRIVE

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 8873 FOUNTAIN PALM ALLEY Winter Garden, FL MLS# O6423477
  • Recently Listed with Virtual Tour
1 of 45
$565,000
3

Beds

2.1

Baths

2,162

Sq.Ft.

8873 FOUNTAIN PALM ALLEY

Winter Garden, FL

View 7840 WINTER WREN STREET Winter Garden, FL MLS# O6421167
$525,900
3

Beds

2.1

Baths

2,004

Sq.Ft.

7840 WINTER WREN STREET

Winter Garden, FL

View 6207 SUNNY TIME AVENUE Winter Garden, FL MLS# O6421162
  • New Construction with Virtual Tour
1 of 23
$547,190
3

Beds

2.1

Baths

1,628

Sq.Ft.

6207 SUNNY TIME AVENUE

Winter Garden, FL

View 2006 WINTERMERE POINTE DRIVE Winter Garden, FL MLS# O6420951
$750,000
5

Beds

4.0

Baths

3,011

Sq.Ft.

2006 WINTERMERE POINTE DRIVE

Winter Garden, FL

View 6137 WATERSIDE ISLAND LANE Winter Garden, FL MLS# O6418786
$599,900
4

Beds

3.1

Baths

2,607

Sq.Ft.

6137 WATERSIDE ISLAND LANE

Winter Garden, FL

View 16082 HAMPTON CROSSING DRIVE Winter Garden, FL MLS# O6420606
  • Recently Listed with Virtual Tour
1 of 60
OPEN HOUSE: Saturday 7/25 12:00 PM - 4:00 PM
$739,900
4

Beds

3.0

Baths

2,240

Sq.Ft.

16082 HAMPTON CROSSING DRIVE

Winter Garden, FL

Courtesy of Lake Mary - WEICHERT, REALTORS® - Hallmark Properties
View 15162 SPINNAKER COVE LANE Winter Garden, FL MLS# S5152807
$765,000
5

Beds

3.0

Baths

3,902

Sq.Ft.

15162 SPINNAKER COVE LANE

Winter Garden, FL

Courtesy of SERHANT
View 15063 GROVESIDE ROAD Winter Garden, FL MLS# O6420626
  • New Construction with Virtual Tour
1 of 19
$516,430
3

Beds

2.1

Baths

1,846

Sq.Ft.

15063 GROVESIDE ROAD

Winter Garden, FL

Courtesy of DRB GROUP REALTY, LLC
View 12632 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# S5152652
  • Recently Listed with Virtual Tour
1 of 20
$575,000
4

Beds

2.1

Baths

2,148

Sq.Ft.

12632 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

View 502 PALM DRIVE Winter Garden, FL MLS# O6415316
  • Virtual Tour
1 of 59
$710,000
4

Beds

2.1

Baths

3,009

Sq.Ft.

502 PALM DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 13361 SUNNY RETREAT LANE Winter Garden, FL MLS# O6419110
  • Adult Community with Virtual Tour
1 of 74
$859,900
4

Beds

3.0

Baths

3,172

Sq.Ft.

13361 SUNNY RETREAT LANE

Winter Garden, FL

View 14543 GOLDEN HARBOR LANE Winter Garden, FL MLS# O6420711
    1 of 44
    OPEN HOUSE: Friday 7/24 1:00 PM - 6:00 PM
    $525,000
    3

    Beds

    2.1

    Baths

    2,039

    Sq.Ft.

    14543 GOLDEN HARBOR LANE

    Winter Garden, FL

    View 17059 HARBOR OAK PARKWAY Winter Garden, FL MLS# G5114379
    • Virtual Tour
    1 of 67
    OPEN HOUSE: Saturday 7/25 12:00 PM - 2:00 PM
    $620,000
    4

    Beds

    3.0

    Baths

    2,692

    Sq.Ft.

    17059 HARBOR OAK PARKWAY

    Winter Garden, FL

    Courtesy of ERA GRIZZARD REAL ESTATE
    View 14301 WHITE MOSS WAY Winter Garden, FL MLS# G5114391
    • Virtual Tour
    1 of 66
    OPEN HOUSE: Saturday 7/25 1:30 PM - 3:30 PM
    $949,999
    5

    Beds

    3.1

    Baths

    4,053

    Sq.Ft.

    14301 WHITE MOSS WAY

    Winter Garden, FL

    View 9976 BEACH PORT DRIVE Winter Garden, FL MLS# O6420960
    $1,274,000
    5

    Beds

    3.1

    Baths

    3,910

    Sq.Ft.

    9976 BEACH PORT DRIVE

    Winter Garden, FL

    Courtesy of CHARLES RUTENBERG REALTY ORLANDO
    View 14591 BLACK QUILL DRIVE Winter Garden, FL MLS# O6420836
    $1,335,000
    4

    Beds

    3.1

    Baths

    4,057

    Sq.Ft.

    14591 BLACK QUILL DRIVE

    Winter Garden, FL

    View 13175 SUNNY RETREAT LANE Winter Garden, FL MLS# O6420975
    $795,000
    3

    Beds

    2.0

    Baths

    2,054

    Sq.Ft.

    13175 SUNNY RETREAT LANE

    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

    989

    Estimated median home price

    $610,000
    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 - 200K20
    $200K - 300K93
    $300K - 400K62
    $400K - 500K141
    $500K - 600K170
    $600K - 700K104
    $700K - 800K115
    $800K - 900K100
    $900K - 1M63
    $1M - Max120

    Homes for Sale by Type in Winter Garden, FL

    Property TypeCount
    Single Family688
    Townhouse131
    Condo136
    Commercial11
    Rental215
    Lots and Land20
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home1
    Farms0

    (Data as of 7/22/2026)

    Information deemed reliable but not guaranteed.

    The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

    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.

    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 7/23/2026.