View 9240 WOODCRANE DRIVE Winter Garden, FL MLS# O6396748
$4,799
5

Beds

4.0

Baths

3,760

Sq.Ft.

9240 WOODCRANE DRIVE

Winter Garden, FL

View 595 9TH STREET 116 Winter Garden, FL MLS# O6398351
$12,000
1,204

Sq.Ft.

595 9TH STREET 116

Winter Garden, FL

View 1220 PRIORY CIRCLE Winter Garden, FL MLS# O6395601
$2,900
3

Beds

2.1

Baths

1,971

Sq.Ft.

1220 PRIORY CIRCLE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 16870 SANCTUARY DRIVE Winter Garden, FL MLS# O6394261
  • Adult Community with Virtual Tour
1 of 100
$12,950
5

Beds

5.0

Baths

4,038

Sq.Ft.

16870 SANCTUARY DRIVE

Winter Garden, FL

Courtesy of FORTUNE GLOBAL REALTY
View 165 WINDTREE LANE U Winter Garden, FL MLS# O6392506
$1,650
2

Beds

2.0

Baths

918

Sq.Ft.

165 WINDTREE LANE U

Winter Garden, FL

View 705 HENNIS ROAD Winter Garden, FL MLS# O6390677
  • New Construction with Virtual Tour
1 of 18
$52,206
11,865

Sq.Ft.

705 HENNIS ROAD

Winter Garden, FL

View 15489 HAMLIN PARK DRIVE Winter Garden, FL MLS# O6390003
$3,150
3

Beds

3.1

Baths

2,072

Sq.Ft.

15489 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 1519 PRIORY CIRCLE Winter Garden, FL MLS# O6382465
$2,725
3

Beds

2.1

Baths

1,956

Sq.Ft.

1519 PRIORY CIRCLE

Winter Garden, FL

View 15010 SUMMER HARVEST STREET Winter Garden, FL MLS# O6371081
  • New Construction with Virtual Tour
1 of 35
$3,200
4

Beds

3.1

Baths

2,322

Sq.Ft.

15010 SUMMER HARVEST STREET

Winter Garden, FL

View Address not provided Winter Garden, FL MLS# O6378945
$1,895
2

Beds

2.0

Baths

1,152

Sq.Ft.

Address not provided

Winter Garden, FL

View 16771 TURTLE HATCH DRIVE D Winter Garden, FL MLS# O6365612
$4,500
4

Beds

3.1

Baths

2,954

Sq.Ft.

16771 TURTLE HATCH DRIVE D

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 11163 GREAT ROCK STREET Winter Garden, FL MLS# O6364381
$4,999
5

Beds

3.0

Baths

3,393

Sq.Ft.

11163 GREAT ROCK STREET

Winter Garden, FL

Courtesy of MANAGER PROP
View 981 VINELAND ROAD Winter Garden, FL MLS# O6364366
  • New Construction with Virtual Tour
1 of 6
$0
8,700

Sq.Ft.

981 VINELAND ROAD

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 186 S MAIN STREET Winter Garden, FL MLS# O6359871
  • New Construction with Virtual Tour
1 of 7
$0
16,000

Sq.Ft.

186 S MAIN STREET

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 17865 ADRIFT ROAD Winter Garden, FL MLS# O6359041
$3,700
4

Beds

3.1

Baths

2,484

Sq.Ft.

17865 ADRIFT ROAD

Winter Garden, FL

View 950 S DILLARD STREET Winter Garden, FL MLS# O6359585
  • New Construction with Virtual Tour
1 of 8
$538,350
4,909

Sq.Ft.

950 S DILLARD STREET

Winter Garden, FL

View 15000 STRATUS LOOP C1 Winter Garden, FL MLS# O6308729
$2,855
3

Beds

2.0

Baths

1,324

Sq.Ft.

15000 STRATUS LOOP C1

Winter Garden, FL

View 15000 STRATUS LOOP A2 Winter Garden, FL MLS# O6308743
$1,880
1

Beds

1.0

Baths

873

Sq.Ft.

15000 STRATUS LOOP A2

Winter Garden, FL

View 15000 STRATUS LOOP B2 Winter Garden, FL MLS# O6308749
$2,375
2

Beds

2.0

Baths

1,130

Sq.Ft.

15000 STRATUS LOOP B2

Winter Garden, FL

View 12324 W COLONIAL DRIVE Winter Garden, FL MLS# O6264561
  • New Construction with Virtual Tour
1 of 19
$54,000
3,025

Sq.Ft.

12324 W COLONIAL 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

1,016

Estimated median home price

$614,995
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 - 300K86
$300K - 400K78
$400K - 500K151
$500K - 600K160
$600K - 700K113
$700K - 800K112
$800K - 900K109
$900K - 1M65
$1M - Max119

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family700
Townhouse146
Condo133
Commercial9
Rental179
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/24/2026)

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 8/24/2026.