View 6001 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5108236
$954,990
6

Beds

4.0

Baths

4,236

Sq.Ft.

6001 FLOWERING CHERRY BEND

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 12940 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6381140
$919,000
5

Beds

4.1

Baths

3,894

Sq.Ft.

12940 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 15327 HERON HIDEAWAY CIRCLE Winter Garden, FL MLS# G5107891
$839,000
7

Beds

4.0

Baths

4,267

Sq.Ft.

15327 HERON HIDEAWAY CIRCLE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 12916 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6379926
$844,000
4

Beds

3.1

Baths

3,005

Sq.Ft.

12916 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
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 15219 MARITIME PINE DRIVE Winter Garden, FL MLS# G5107311
$998,124
6

Beds

4.0

Baths

4,236

Sq.Ft.

15219 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6511 SHORE JUNIPER STREET Winter Garden, FL MLS# G5107313
$961,170
6

Beds

4.0

Baths

4,236

Sq.Ft.

6511 SHORE JUNIPER STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 16143 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5107301
$875,595
4

Beds

3.0

Baths

2,740

Sq.Ft.

16143 LEYLAND CYPRESS LANE

Winter Garden, FL

View 5971 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5107163
$849,970
5

Beds

4.1

Baths

3,076

Sq.Ft.

5971 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5949 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5107173
$845,340
5

Beds

4.1

Baths

3,076

Sq.Ft.

5949 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15672 SHOREBIRD LANE Winter Garden, FL MLS# O6375411
$849,900
4

Beds

3.1

Baths

2,800

Sq.Ft.

15672 SHOREBIRD LANE

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
View 131 OAK LAUREL DRIVE Winter Garden, FL MLS# O6374501
$834,000
3

Beds

3.1

Baths

1,906

Sq.Ft.

131 OAK LAUREL DRIVE

Winter Garden, FL

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

Courtesy of COLDWELL BANKER REALTY
View 5217 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6363382
$899,000
4

Beds

3.1

Baths

3,144

Sq.Ft.

5217 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
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 14327 WABASSO LOOP Winter Garden, FL MLS# O6347454
$869,990
5

Beds

4.0

Baths

3,710

Sq.Ft.

14327 WABASSO LOOP

Winter Garden, FL

Courtesy of KARDOSH REALTY
View 17552 LAKE STAR ROAD Winter Garden, FL MLS# O6344668
$999,000
4

Beds

3.1

Baths

2,605

Sq.Ft.

17552 LAKE STAR ROAD

Winter Garden, FL

View 15213 MARITIME PINE DRIVE Winter Garden, FL MLS# G5102285
$899,360
4

Beds

3.0

Baths

2,879

Sq.Ft.

15213 MARITIME PINE DRIVE

Winter Garden, FL

View 15280 MARITIME PINE DRIVE Winter Garden, FL MLS# G5102291
$979,990
6

Beds

3.0

Baths

3,550

Sq.Ft.

15280 MARITIME PINE DRIVE

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

1,026

Estimated median home price

$610,805
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 - 200K21
$200K - 300K86
$300K - 400K77
$400K - 500K155
$500K - 600K166
$600K - 700K116
$700K - 800K113
$800K - 900K109
$900K - 1M64
$1M - Max118

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family711
Townhouse148
Condo131
Commercial9
Rental182
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/27/2026)

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 8/28/2026.