529 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 729 MEADOW GLADE DRIVE Winter Garden, FL MLS# O6407943
    1 of 34
    OPEN HOUSE: Saturday 6/20 11:00 AM - 1:00 PM
    $515,000
    3

    Beds

    2.0

    Baths

    2,070

    Sq.Ft.

    729 MEADOW GLADE DRIVE

    Winter Garden, FL

    View 16230 Carraway Bay Alley Winter Garden, FL MLS# 1226408
    $529,999
    4

    Beds

    3.1

    Baths

    2,474

    Sq.Ft.

    16230 Carraway Bay Alley

    Winter Garden, FL

    View 14755 MASTHEAD LANDING CIRCLE Winter Garden, FL MLS# O6408082
    $580,000
    4

    Beds

    2.0

    Baths

    2,258

    Sq.Ft.

    14755 MASTHEAD LANDING CIRCLE

    Winter Garden, FL

    Courtesy of SUSANA JORDAN STUTSMAN
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 15518 FOUNTAIN COVE COURT Winter Garden, FL MLS# O6407942
    $574,990
    3

    Beds

    3.0

    Baths

    2,040

    Sq.Ft.

    15518 FOUNTAIN COVE COURT

    Winter Garden, FL

    Courtesy of CHARLES RUTENBERG REALTY ORLANDO
    View 14501 GROVE RESORT AVE 1535 1535 Winter Garden, FL MLS# S5150001
    $410,990
    3

    Beds

    2.0

    Baths

    1,396

    Sq.Ft.

    14501 GROVE RESORT AVE 1535 1535

    Winter Garden, FL

    Courtesy of SACKS REALTY GROUP, INC.
    View 13527 DANIELS LANDING CIRCLE Winter Garden, FL MLS# O6408480
    $335,000
    3

    Beds

    2.1

    Baths

    1,365

    Sq.Ft.

    13527 DANIELS LANDING CIRCLE

    Winter Garden, FL

    Courtesy of LPT REALTY, LLC
    View 170 WINDTREE LANE Winter Garden, FL MLS# S5150050
    $204,900
    2

    Beds

    2.0

    Baths

    918

    Sq.Ft.

    170 WINDTREE LANE

    Winter Garden, FL

    Courtesy of LA ROSA REALTY LLC
    View 12597 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6407413
    $520,000
    3

    Beds

    2.0

    Baths

    2,322

    Sq.Ft.

    12597 ENCORE AT OVATION WAY

    Winter Garden, FL

    Courtesy of INTEREALTY SERVICE
    View 5545 BOWMAN DRIVE Winter Garden, FL MLS# O6407484
    • Virtual Tour
    1 of 29
    OPEN HOUSE: Saturday 6/20 9:00 AM - 7:00 PM
    $480,000
    2

    Beds

    2.1

    Baths

    1,998

    Sq.Ft.

    5545 BOWMAN DRIVE

    Winter Garden, FL

    View 441 E CYPRESS STREET Winter Garden, FL MLS# O6407560
    $320,000
    Studio

    Beds

    0.0

    Baths

    441 E CYPRESS STREET

    Winter Garden, FL

    Courtesy of NOVA REAL ESTATE SERVICES INC
    View 6044 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5112346
    $579,820
    4

    Beds

    3.0

    Baths

    2,102

    Sq.Ft.

    6044 FLOWERING CHERRY BEND

    Winter Garden, FL

    Courtesy of OLYMPUS EXECUTIVE REALTY INC
    View 342 WINDFORD COURT Winter Garden, FL MLS# O6407632
    $339,900
    3

    Beds

    2.0

    Baths

    1,194

    Sq.Ft.

    342 WINDFORD COURT

    Winter Garden, FL

    Courtesy of RE/MAX 200 REALTY
    View 14002 AVENUE OF THE GROVES Winter Garden, FL MLS# S5149866
    $345,000
    2

    Beds

    2.1

    Baths

    1,271

    Sq.Ft.

    14002 AVENUE OF THE GROVES

    Winter Garden, FL

    Courtesy of CENTURY 21 CARIOTI
    View 6102 WHISPERING GLEN Winter Garden, FL MLS# O6407803
    • New Construction with Virtual Tour
    1 of 28
    $576,890
    4

    Beds

    2.1

    Baths

    1,913

    Sq.Ft.

    6102 WHISPERING GLEN

    Winter Garden, FL

    Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
    View 6174 WHISPERING GLEN Winter Garden, FL MLS# O6407807
    • New Construction with Virtual Tour
    1 of 20
    $518,290
    3

    Beds

    2.1

    Baths

    1,628

    Sq.Ft.

    6174 WHISPERING GLEN

    Winter Garden, FL

    Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
    View 11117 BOSTWICK ALLEY Winter Garden, FL MLS# O6407552
    $507,000
    3

    Beds

    2.0

    Baths

    1,685

    Sq.Ft.

    11117 BOSTWICK ALLEY

    Winter Garden, FL

    View 15025 PIGEON PLUM LANE Winter Garden, FL MLS# O6404948
    $599,990
    4

    Beds

    2.1

    Baths

    2,605

    Sq.Ft.

    15025 PIGEON PLUM LANE

    Winter Garden, FL

    View 15615 HONEYBELL DRIVE Winter Garden, FL MLS# O6406267
    $389,900
    3

    Beds

    2.1

    Baths

    1,584

    Sq.Ft.

    15615 HONEYBELL DRIVE

    Winter Garden, FL

    Courtesy of KELLER WILLIAMS CLASSIC
    View 7667 SILVER MEADOW STREET Winter Garden, FL MLS# G5112278
    $551,130
    4

    Beds

    3.0

    Baths

    2,102

    Sq.Ft.

    7667 SILVER MEADOW STREET

    Winter Garden, FL

    Courtesy of OLYMPUS EXECUTIVE REALTY INC
    View 1015 WESTSIDE DRIVE Winter Garden, FL MLS# O6407229
    • Virtual Tour
    1 of 23
    OPEN HOUSE: Saturday 6/20 9:00 AM - 7:00 PM
    $224,000
    3

    Beds

    2.0

    Baths

    938

    Sq.Ft.

    1015 WESTSIDE DRIVE

    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

    1,085

    Estimated median home price

    $615,000
    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 - 300K90
    $300K - 400K77
    $400K - 500K147
    $500K - 600K189
    $600K - 700K132
    $700K - 800K116
    $800K - 900K101
    $900K - 1M73
    $1M - Max137

    Homes for Sale by Type in Winter Garden, FL

    Property TypeCount
    Single Family769
    Townhouse140
    Condo137
    Commercial11
    Rental202
    Lots and Land24
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home1
    Farms0

    (Data as of 6/19/2026)

    Information deemed reliable but not guaranteed.

    The data relating to real estate for sale/lease on this web site come in part from the New Smyrna Beach Board of REALTORS® Multiple Listing Service (MLS) in which this real estate firm (Broker) participates. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with the Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with the MLS IDX logo. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein or for their use or interpretation by the user. Federal law prohibits discrimination on the basis of race, color, sex, religion, handicap, familial status or national origin in the sale, rental or financing of housing.

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    IDX information 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.

    Some properties which appear for sale on this website may subsequently have sold and may no longer be available.

    © Copyright 2026 New Smyrna Beach Board of REALTORS, Inc. All rights Reserved.

    The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

    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.

    Data is updated as of 6/20/2026.

    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

    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.

    Copyright 2026 BeachesMLS, Inc. All rights reserved.

    All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

    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.

    Data is updated as of 6/20/2026.

    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 6/20/2026.