View 20 E DIVISION STREET Winter Garden, FL MLS# O6413659
$1,080,000
4

Beds

3.0

Baths

2,729

Sq.Ft.

20 E DIVISION STREET

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1651 AMSEL FALLS PARK TERRACE Winter Garden, FL MLS# O6414027
$1,080,000
4

Beds

3.2

Baths

3,881

Sq.Ft.

1651 AMSEL FALLS PARK TERRACE

Winter Garden, FL

View 806 JOHNS POINT DRIVE Winter Garden, FL MLS# O6418276
$1,075,000
4

Beds

4.1

Baths

3,552

Sq.Ft.

806 JOHNS POINT DRIVE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 14312 SUNBRIDGE CIRCLE Winter Garden, FL MLS# O6414430
$1,060,000
5

Beds

4.0

Baths

4,225

Sq.Ft.

14312 SUNBRIDGE CIRCLE

Winter Garden, FL

View 14825 ELLINGSWORTH LANE Winter Garden, FL MLS# O6430917
  • Recently Listed with Virtual Tour
1 of 29
$1,050,000
5

Beds

4.1

Baths

4,732

Sq.Ft.

14825 ELLINGSWORTH LANE

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
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

Courtesy of LPT REALTY, LLC
View 15037 LAKE BESSIE LOOP Winter Garden, FL MLS# O6418541
$1,045,000
7

Beds

4.0

Baths

3,938

Sq.Ft.

15037 LAKE BESSIE LOOP

Winter Garden, FL

View 12904 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6381734
$1,032,000
5

Beds

4.1

Baths

3,894

Sq.Ft.

12904 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 9240 BRADLEIGH DRIVE Winter Garden, FL MLS# O6421967
$1,025,000
6

Beds

5.1

Baths

4,124

Sq.Ft.

9240 BRADLEIGH DRIVE

Winter Garden, FL

View 16104 SANDHILL ROAD Winter Garden, FL MLS# O6411589
$1,020,000
3

Beds

2.0

Baths

1,364

Sq.Ft.

16104 SANDHILL ROAD

Winter Garden, FL

View 6274 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5115512
$1,016,060
6

Beds

4.0

Baths

4,236

Sq.Ft.

6274 FLOWERING CHERRY BEND

Winter Garden, FL

View 13852 JOMATT LOOP Winter Garden, FL MLS# O6427925
$1,015,000
4

Beds

3.1

Baths

4,000

Sq.Ft.

13852 JOMATT LOOP

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 16149 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5104655
$1,005,995
5

Beds

3.1

Baths

3,764

Sq.Ft.

16149 LEYLAND CYPRESS LANE

Winter Garden, FL

View 851 9TH STREET Winter Garden, FL MLS# O6306969
$1,000,000
Studio

Beds

0.0

Baths

851 9TH STREET

Winter Garden, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 9207 BUSACO PARK WAY Winter Garden, FL MLS# O6366636
$1,000,000
5

Beds

4.0

Baths

3,291

Sq.Ft.

9207 BUSACO PARK WAY

Winter Garden, FL

View 6394 WILD PERSIMMON WAY Winter Garden, FL MLS# G5107546
$999,990
6

Beds

4.0

Baths

4,236

Sq.Ft.

6394 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6352 WILD PERSIMMON WAY Winter Garden, FL MLS# G5107315
$999,914
6

Beds

4.0

Baths

4,236

Sq.Ft.

6352 WILD PERSIMMON WAY

Winter Garden, FL

View 13536 SUNSET LAKES CIRCLE Winter Garden, FL MLS# O6399227
  • Virtual Tour
1 of 68
OPEN HOUSE: Saturday 8/22 2:00 PM - 4:00 PM
$999,900
5

Beds

4.0

Baths

3,389

Sq.Ft.

13536 SUNSET LAKES CIRCLE

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
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

View 289 CRYSTAL WOOD DRIVE Winter Garden, FL MLS# O6433103
  • Recently Listed with Virtual Tour
1 of 34
$999,270
4

Beds

3.1

Baths

3,370

Sq.Ft.

289 CRYSTAL WOOD 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

1,025

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 - 100K2
$100K - 200K21
$200K - 300K90
$300K - 400K78
$400K - 500K150
$500K - 600K166
$600K - 700K112
$700K - 800K115
$800K - 900K108
$900K - 1M64
$1M - Max119

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family706
Townhouse144
Condo137
Commercial9
Rental175
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/21/2026)

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 8/21/2026.