View 16006 GILDEN WAY Winter Garden, FL MLS# O6392997
$1,084,999
5

Beds

4.0

Baths

3,617

Sq.Ft.

16006 GILDEN WAY

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 6261 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5110034
$890,955
6

Beds

4.0

Baths

4,236

Sq.Ft.

6261 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 11205 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6392839
  • New Construction with Virtual Tour
1 of 31
$939,990
4

Beds

3.1

Baths

3,327

Sq.Ft.

11205 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 12965 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6392975
  • New Construction with Virtual Tour
1 of 31
$882,932
5

Beds

4.1

Baths

3,101

Sq.Ft.

12965 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 14354 WABASSO LOOP Winter Garden, FL MLS# O6392378
$939,000
4

Beds

4.0

Baths

2,881

Sq.Ft.

14354 WABASSO LOOP

Winter Garden, FL

Courtesy of HOUWZER INC
View 17090 HAGGERTY HOLLOW ESTATE Winter Garden, FL MLS# G5109783
$1,130,987
6

Beds

4.1

Baths

3,412

Sq.Ft.

17090 HAGGERTY HOLLOW ESTATE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8216 TOPSAIL PLACE Winter Garden, FL MLS# O6391155
$974,900
4

Beds

3.1

Baths

3,055

Sq.Ft.

8216 TOPSAIL PLACE

Winter Garden, FL

Courtesy of REALTY ONE GROUP MVP
View 14766 ELLINGSWORTH LANE Winter Garden, FL MLS# O6390518
$1,099,000
5

Beds

4.1

Baths

4,661

Sq.Ft.

14766 ELLINGSWORTH LANE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 617 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6389100
    1 of 53
    OPEN HOUSE: Sunday 6/7 12:00 PM - 2:00 PM
    $1,139,000
    4

    Beds

    4.1

    Baths

    3,624

    Sq.Ft.

    617 CANOPY ESTATES DRIVE

    Winter Garden, FL

    Courtesy of HOMEVEST REALTY
    View 6243 FLOWERIND CHERRY BEND Winter Garden, FL MLS# G5109529
    $946,950
    6

    Beds

    4.0

    Baths

    4,236

    Sq.Ft.

    6243 FLOWERIND CHERRY BEND

    Winter Garden, FL

    Courtesy of OLYMPUS EXECUTIVE REALTY INC
    View 15377 MARITIME PINE DRIVE Winter Garden, FL MLS# G5109533
    $999,315
    6

    Beds

    4.0

    Baths

    4,222

    Sq.Ft.

    15377 MARITIME PINE DRIVE

    Winter Garden, FL

    Courtesy of OLYMPUS EXECUTIVE REALTY INC
    View 16071 BARKLY RIDGE COURT Winter Garden, FL MLS# O6390569
    $1,150,000
    4

    Beds

    3.0

    Baths

    2,986

    Sq.Ft.

    16071 BARKLY RIDGE COURT

    Winter Garden, FL

    Courtesy of WRA BUSINESS & REAL ESTATE
    View 744 LAKE BRIM DRIVE Winter Garden, FL MLS# O6388775
    $949,000
    4

    Beds

    3.1

    Baths

    2,667

    Sq.Ft.

    744 LAKE BRIM DRIVE

    Winter Garden, FL

    Courtesy of BHHS FLORIDA REALTY
    View 6221 ARGENT WOOD DRIVE Winter Garden, FL MLS# O6388355
    • New Construction with Virtual Tour
    1 of 54
    $930,000
    5

    Beds

    4.1

    Baths

    3,878

    Sq.Ft.

    6221 ARGENT WOOD DRIVE

    Winter Garden, FL

    Courtesy of MS LAND & BUILDING LLC
    View 156 STANTON ESTATES CIRCLE Winter Garden, FL MLS# O6384801
    $1,149,950
    4

    Beds

    4.0

    Baths

    3,170

    Sq.Ft.

    156 STANTON ESTATES CIRCLE

    Winter Garden, FL

    Courtesy of FATHOM REALTY FL LLC
    View 1689 CRANLEIGH DR Winter Garden, FL MLS# O6387674
    $875,000
    4

    Beds

    4.0

    Baths

    2,937

    Sq.Ft.

    1689 CRANLEIGH DR

    Winter Garden, FL

    Courtesy of HOMEVEST REALTY
    View 13037 SANDCASTLE DRIVE Winter Garden, FL MLS# O6387932
    • Adult Community with Virtual Tour
    1 of 50
    $994,295
    3

    Beds

    3.0

    Baths

    2,902

    Sq.Ft.

    13037 SANDCASTLE DRIVE

    Winter Garden, FL

    Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
    View 9409 EMERALD BERRY DRIVE Winter Garden, FL MLS# S5144953
    $875,000
    4

    Beds

    3.1

    Baths

    2,923

    Sq.Ft.

    9409 EMERALD BERRY DRIVE

    Winter Garden, FL

    Courtesy of LA ROSA REALTY LLC
    View 9218 HOLLISTON CREEK PLACE Winter Garden, FL MLS# O6386394
    $920,000
    4

    Beds

    3.1

    Baths

    3,087

    Sq.Ft.

    9218 HOLLISTON CREEK PLACE

    Winter Garden, FL

    Courtesy of WRA BUSINESS & REAL ESTATE
    View 64 N PARK AVENUE Winter Garden, FL MLS# O6385285
    $1,095,000
    4

    Beds

    4.0

    Baths

    2,225

    Sq.Ft.

    64 N PARK AVENUE

    Winter Garden, FL

    Courtesy of CORCORAN PREMIER REALTY

    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

    1,052

    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 - 200K24
    $200K - 300K87
    $300K - 400K80
    $400K - 500K145
    $500K - 600K174
    $600K - 700K130
    $700K - 800K117
    $800K - 900K91
    $900K - 1M73
    $1M - Max130

    Homes for Sale by Type in Winter Garden, FL

    Property TypeCount
    Single Family736
    Townhouse138
    Condo138
    Commercial11
    Rental199
    Lots and Land26
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home1
    Farms0

    (Data as of 6/6/2026)

    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 6/6/2026.