View 15216 CHAPTER WAY Winter Garden, FL MLS# S5139219
$515,000
4

Beds

3.0

Baths

2,042

Sq.Ft.

15216 CHAPTER WAY

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 14012 PEACH ORCHARD WAY Winter Garden, FL MLS# O6364564
$595,000
4

Beds

2.0

Baths

2,516

Sq.Ft.

14012 PEACH ORCHARD WAY

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 13398 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5105139
  • New Construction with Virtual Tour
1 of 28
$723,990
4

Beds

2.1

Baths

2,235

Sq.Ft.

13398 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 13386 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5105140
  • New Construction with Virtual Tour
1 of 28
$819,990
5

Beds

4.0

Baths

3,065

Sq.Ft.

13386 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13362 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5105141
  • New Construction with Virtual Tour
1 of 28
$809,990
5

Beds

4.2

Baths

3,076

Sq.Ft.

13362 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 12036 HOLYSTONE STREET Winter Garden, FL MLS# S5139531
$455,000
3

Beds

2.1

Baths

1,817

Sq.Ft.

12036 HOLYSTONE STREET

Winter Garden, FL

Courtesy of NAIM REAL ESTATE LLC
View 8019 RAIL STREET Winter Garden, FL MLS# O6365660
$734,900
3

Beds

2.1

Baths

2,707

Sq.Ft.

8019 RAIL STREET

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 13545 PEARL BEACH STREET Winter Garden, FL MLS# S5139428
  • Adult Community with Virtual Tour
1 of 40
$429,375
2

Beds

2.0

Baths

1,579

Sq.Ft.

13545 PEARL BEACH STREET

Winter Garden, FL

Courtesy of IMAGINATION REALTY, INC
View 934 MCKINNON SQUARE Winter Garden, FL MLS# O6362523
$795,500
3

Beds

2.1

Baths

2,536

Sq.Ft.

934 MCKINNON SQUARE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 15607 SYLVESTER PALM DRIVE Winter Garden, FL MLS# O6364144
$739,000
3

Beds

2.0

Baths

2,092

Sq.Ft.

15607 SYLVESTER PALM DRIVE

Winter Garden, FL

Courtesy of THE C SMITH REAL ESTATE GROUP LLC
View 10684 WORDS DRIVE Winter Garden, FL MLS# O6364184
$408,000
3

Beds

2.1

Baths

1,636

Sq.Ft.

10684 WORDS DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 14501 GROVE RESORT AVENUE 2536 Winter Garden, FL MLS# O6364192
$314,900
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 2536

Winter Garden, FL

Courtesy of MBI REALTY LLC
View 1527 VISCAYA COVE BOULEVARD Winter Garden, FL MLS# O6364279
    1 of 69
    OPEN HOUSE: Sunday 1/4 12:00 PM - 3:00 PM
    $569,000
    4

    Beds

    3.1

    Baths

    2,502

    Sq.Ft.

    1527 VISCAYA COVE BOULEVARD

    Winter Garden, FL

    Courtesy of EMPIRE NETWORK REALTY
    View 15688 ORANGE HARVEST LOOP Winter Garden, FL MLS# O6364300
    $485,000
    3

    Beds

    2.1

    Baths

    2,012

    Sq.Ft.

    15688 ORANGE HARVEST LOOP

    Winter Garden, FL

    Courtesy of EMPIRE NETWORK REALTY
    View 634 FOSTER AVENUE Winter Garden, FL MLS# TB8451057
    $315,000
    2

    Beds

    1.0

    Baths

    696

    Sq.Ft.

    634 FOSTER AVENUE

    Winter Garden, FL

    Courtesy of FLAT FEE MLS REALTY
    View 14227 AVENUE OF THE GROVES RUN Winter Garden, FL MLS# O6339064
    $359,000
    2

    Beds

    2.1

    Baths

    1,266

    Sq.Ft.

    14227 AVENUE OF THE GROVES RUN

    Winter Garden, FL

    Courtesy of CT HOMES REALTY CORPORATION
    View 14494 BREAKWATER WAY Winter Garden, FL MLS# S5139023
    $720,000
    5

    Beds

    3.0

    Baths

    3,638

    Sq.Ft.

    14494 BREAKWATER WAY

    Winter Garden, FL

    Courtesy of NUMBER 1 BROKER, LLC
    View 5526 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# O6365476
    $720,000
    5

    Beds

    3.0

    Baths

    2,240

    Sq.Ft.

    5526 NEW INDEPENDENCE PARKWAY

    Winter Garden, FL

    Courtesy of WRA BUSINESS & REAL ESTATE
    View 16180 ARBOR CREST ALLEY Winter Garden, FL MLS# A4673607
    $409,000
    3

    Beds

    2.1

    Baths

    1,996

    Sq.Ft.

    16180 ARBOR CREST ALLEY

    Winter Garden, FL

    Courtesy of SAVVY AVENUE, LLC
    View 13011 TRANQUIL WATER ALLEY Winter Garden, FL MLS# G5105040
    • New Construction with Virtual Tour
    1 of 61
    $599,989
    3

    Beds

    2.1

    Baths

    2,078

    Sq.Ft.

    13011 TRANQUIL WATER ALLEY

    Winter Garden, FL

    Courtesy of OLYMPUS EXECUTIVE REALTY INC

    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

    774

    Estimated median home price

    $589,000
    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 - 100K6
    $100K - 200K8
    $200K - 300K64
    $300K - 400K82
    $400K - 500K132
    $500K - 600K123
    $600K - 700K85
    $700K - 800K68
    $800K - 900K63
    $900K - 1M49
    $1M - Max94

    Homes for Sale by Type in Winter Garden, FL

    Property TypeCount
    Single Family502
    Townhouse117
    Condo110
    Commercial9
    Rental224
    Lots and Land32
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home1
    Farms0

    (Data as of 1/3/2026)

    Information deemed reliable but 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.

    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

    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 1/3/2026.

    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 1/3/2026.