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

Courtesy of CORCORAN PREMIER REALTY
View 12143 STONEYBROOK WEST PARKWAY 101-102 Winter Garden, FL MLS# O6428942
  • New Construction with Virtual Tour
1 of 8
$394,200
7,300

Sq.Ft.

12143 STONEYBROOK WEST PARKWAY 101-102

Winter Garden, FL

Courtesy of PROPERTY INVESTMENT BROKERS
View 981 VINELAND ROAD Winter Garden, FL MLS# O6364366
  • New Construction with Virtual Tour
1 of 6
$304,500
8,700

Sq.Ft.

981 VINELAND ROAD

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 12283 STONEYBROOK WEST PARKWAY B Winter Garden, FL MLS# O6425191
  • New Construction with Virtual Tour
1 of 17
$108,000
2,400

Sq.Ft.

12283 STONEYBROOK WEST PARKWAY B

Winter Garden, FL

Courtesy of REVEL REALTY LLC
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

Courtesy of ROI AVE LLC
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

Courtesy of ROI AVE LLC
View 215 CENTER STREET 227 Winter Garden, FL MLS# O6415984
$43,794
2,304

Sq.Ft.

215 CENTER STREET 227

Winter Garden, FL

Courtesy of THE KLR GROUP LLC
View 1002 S DILLARD STREET 110 Winter Garden, FL MLS# G5119281
$40,977
1,500

Sq.Ft.

1002 S DILLARD STREET 110

Winter Garden, FL

Courtesy of DENIZ REALTY PARTNERS LLC
View 595 9TH STREET 115 Winter Garden, FL MLS# O6398346
$30,000
1,204

Sq.Ft.

595 9TH STREET 115

Winter Garden, FL

Courtesy of ENGEL & VOELKERS LAKELAND
View 595 9TH STREET Winter Garden, FL MLS# O6398340
  • Virtual Tour
1 of 17
$27,600
1,204

Sq.Ft.

595 9TH STREET

Winter Garden, FL

Courtesy of ENGEL & VOELKERS LAKELAND
View 595 9TH STREET 116 Winter Garden, FL MLS# O6398351
$18,000
1,204

Sq.Ft.

595 9TH STREET 116

Winter Garden, FL

Courtesy of ENGEL & VOELKERS LAKELAND
View 7573 GREEN MOUNTAIN WAY Winter Garden, FL MLS# O6423959
$8,000
4

Beds

3.1

Baths

3,333

Sq.Ft.

7573 GREEN MOUNTAIN WAY

Winter Garden, FL

Courtesy of PRISTINE INTERNATIONAL REALTY LLC
View 1698 JUNIPER HAMMOCK STREET Winter Garden, FL MLS# O6445580
$7,500
7

Beds

4.0

Baths

4,700

Sq.Ft.

1698 JUNIPER HAMMOCK STREET

Winter Garden, FL

Courtesy of Lake Mary - WEICHERT, REALTORS® - Hallmark Properties
View 17546 LAKE STAR ROAD Winter Garden, FL MLS# S5157675
$6,900
5

Beds

4.1

Baths

3,767

Sq.Ft.

17546 LAKE STAR ROAD

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
View 5358 BOWMAN DRIVE Winter Garden, FL MLS# O6444394
$6,800
4

Beds

4.0

Baths

3,445

Sq.Ft.

5358 BOWMAN DRIVE

Winter Garden, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 12934 CANOPY WOODS WAY Winter Garden, FL MLS# O6447215
$6,800
4

Beds

4.1

Baths

3,636

Sq.Ft.

12934 CANOPY WOODS WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 14807 WINTER STAY DRIVE Winter Garden, FL MLS# O6434655
$6,500
5

Beds

4.0

Baths

3,856

Sq.Ft.

14807 WINTER STAY DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 16477 SILVER BROOK WAY Winter Garden, FL MLS# O6441878
$6,000
5

Beds

4.1

Baths

3,889

Sq.Ft.

16477 SILVER BROOK WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 14492 SUNBRIDGE CIRCLE Winter Garden, FL MLS# S5160315
$6,000
5

Beds

4.0

Baths

4,436

Sq.Ft.

14492 SUNBRIDGE CIRCLE

Winter Garden, FL

Courtesy of FLORIDA REALTY TEAM OF CENTRAL
View 14612 GLADE HILL PARK WAY Winter Garden, FL MLS# S5151295
$5,900
5

Beds

4.1

Baths

3,892

Sq.Ft.

14612 GLADE HILL PARK WAY

Winter Garden, FL

Courtesy of LA ROSA REALTY INTERNACIONAL L

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

982

Estimated median home price

$595,000
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 - 200K35
$200K - 300K74
$300K - 400K75
$400K - 500K151
$500K - 600K168
$600K - 700K113
$700K - 800K109
$800K - 900K107
$900K - 1M51
$1M - Max98

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family675
Townhouse148
Condo121
Commercial6
Rental237
Lots and Land25
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 10/27/2026)

Information deemed reliable but not guaranteed.

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

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 10/28/2026.