View 9296 BOLERO ROAD Winter Garden, FL MLS# O6422122
$779,000
4

Beds

3.0

Baths

2,117

Sq.Ft.

9296 BOLERO ROAD

Winter Garden, FL

View 13158 BOUNTY AVENUE Winter Garden, FL MLS# O6421321
    1 of 46
    OPEN HOUSE: Saturday 8/1 1:00 PM - 4:00 PM
    $395,000
    3

    Beds

    2.1

    Baths

    1,567

    Sq.Ft.

    13158 BOUNTY AVENUE

    Winter Garden, FL

    View 1642 CHANDELLE LANE Winter Garden, FL MLS# G5114093
    $689,900
    5

    Beds

    3.0

    Baths

    2,918

    Sq.Ft.

    1642 CHANDELLE LANE

    Winter Garden, FL

    The time to sell is now! THE TIME TO SELL IS NOW!
    View 13349 HARBOR SHORE LANE Winter Garden, FL MLS# G5114466
    $316,000
    2

    Beds

    2.1

    Baths

    1,236

    Sq.Ft.

    13349 HARBOR SHORE LANE

    Winter Garden, FL

    View 1711 AMSEL FALLS PARK TERRACE Winter Garden, FL MLS# G5114517
    $1,046,000
    5

    Beds

    4.0

    Baths

    3,863

    Sq.Ft.

    1711 AMSEL FALLS PARK TERRACE

    Winter Garden, FL

    View 5330 LAKE VIRGINIA STREET Winter Garden, FL MLS# O6420269
    $579,000
    4

    Beds

    3.1

    Baths

    2,515

    Sq.Ft.

    5330 LAKE VIRGINIA STREET

    Winter Garden, FL

    View 547 SEASIDE COVE STREET Winter Garden, FL MLS# G5114554
    $715,000
    5

    Beds

    2.1

    Baths

    3,290

    Sq.Ft.

    547 SEASIDE COVE STREET

    Winter Garden, FL

    View 14629 BAHAMA SWALLOW BOULEVARD Winter Garden, FL MLS# O6421797
    $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
    View 7840 WINTER WREN STREET Winter Garden, FL MLS# O6421167
    $519,900
    3

    Beds

    2.1

    Baths

    2,004

    Sq.Ft.

    7840 WINTER WREN STREET

    Winter Garden, FL

    View 1152 PRADO LANE Winter Garden, FL MLS# O6413825
    • New Construction with Virtual Tour
    1 of 13
    $2,615,320
    6

    Beds

    6.1

    Baths

    4,658

    Sq.Ft.

    1152 PRADO LANE

    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
    $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
    $575,000
    4

    Beds

    2.1

    Baths

    2,148

    Sq.Ft.

    12632 CLEAR SAPPHIRE DRIVE

    Winter Garden, FL

    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

    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

    1,076

    Estimated median home price

    $612,805
    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 - 200K24
    $200K - 300K96
    $300K - 400K68
    $400K - 500K156
    $500K - 600K184
    $600K - 700K113
    $700K - 800K129
    $800K - 900K104
    $900K - 1M66
    $1M - Max135

    Homes for Sale by Type in Winter Garden, FL

    Property TypeCount
    Single Family759
    Townhouse143
    Condo141
    Commercial10
    Rental221
    Lots and Land20
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home1
    Farms0

    (Data as of 7/27/2026)

    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 7/27/2026.