View 950 S DILLARD STREET Winter Garden, FL MLS# O6359585
  • New Construction with Virtual Tour
1 of 7
$552,900
4,909

Sq.Ft.

950 S DILLARD STREET

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 7159 AVALON ROAD 6 Winter Garden, FL MLS# G5097039
  • New Construction with Virtual Tour
1 of 21
$463,632
9,736

Sq.Ft.

7159 AVALON ROAD 6

Winter Garden, FL

Courtesy of MORRIS REALTY AND INVESTMENTS
View 776 BUSINESS PARK BOULEVARD Winter Garden, FL MLS# G5092094
$155,100
10,340

Sq.Ft.

776 BUSINESS PARK BOULEVARD

Winter Garden, FL

Courtesy of ENGEL & VOLKERS CLERMONT
The time to sell is now! THE TIME TO SELL IS NOW!
View 12324 W COLONIAL DRIVE Winter Garden, FL MLS# O6264561
  • New Construction with Virtual Tour
1 of 19
$53,988
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 595 9TH STREET 115 Winter Garden, FL MLS# O6398346
$42,000
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
$34,800
1,204

Sq.Ft.

595 9TH STREET

Winter Garden, FL

Courtesy of ENGEL & VOELKERS LAKELAND
View 215 CENTER STREET 225/227 Winter Garden, FL MLS# O6398301
  • New Construction with Virtual Tour
1 of 19
$32,400
2,304

Sq.Ft.

215 CENTER STREET 225/227

Winter Garden, FL

Courtesy of PREICO REALTY SERVICES INC
View 7556 JOHN HANCOCK DRIVE Winter Garden, FL MLS# O6380128
  • New Construction with Virtual Tour
1 of 95
$18,000
5

Beds

6.1

Baths

5,108

Sq.Ft.

7556 JOHN HANCOCK DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 16870 SANCTUARY DRIVE Winter Garden, FL MLS# O6394261
  • Recently Listed 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 595 9TH STREET 116 Winter Garden, FL MLS# O6398351
$12,000
1,204

Sq.Ft.

595 9TH STREET 116

Winter Garden, FL

Courtesy of ENGEL & VOELKERS LAKELAND
View 15704 MARINA BAY DRIVE Winter Garden, FL MLS# O6380878
$11,500
5

Beds

5.1

Baths

5,005

Sq.Ft.

15704 MARINA BAY DRIVE

Winter Garden, FL

Courtesy of DOUBLE M GROUP COMPANY
View 12927 CANOPY WOODS WAY Winter Garden, FL MLS# S5136184
$9,250
5

Beds

4.1

Baths

4,671

Sq.Ft.

12927 CANOPY WOODS WAY

Winter Garden, FL

Courtesy of B LIVE COMMERCIAL AND RESIDENT
View 1021 TEMPLE GROVE PLACE Winter Garden, FL MLS# O6407353
  • Recently Listed with Virtual Tour
1 of 66
$8,500
4

Beds

4.1

Baths

3,185

Sq.Ft.

1021 TEMPLE GROVE PLACE

Winter Garden, FL

Courtesy of MAINFRAME REAL ESTATE
View 17342 GLOSSY POMELO WAY Winter Garden, FL MLS# O6406397
  • Recently Listed with Virtual Tour
1 of 81
$6,500
5

Beds

5.1

Baths

4,977

Sq.Ft.

17342 GLOSSY POMELO WAY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16031 SILVER BROOK WAY Winter Garden, FL MLS# O6409094
  • Recently Listed with Virtual Tour
1 of 37
$6,500
5

Beds

4.1

Baths

3,979

Sq.Ft.

16031 SILVER BROOK WAY

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 5301 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6372658
$6,000
5

Beds

4.1

Baths

3,871

Sq.Ft.

5301 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of CELEBRITY GLOBAL REALTY LLC
View 10264 LOVE STORY STREET Winter Garden, FL MLS# O6409006
  • Recently Listed with Virtual Tour
1 of 35
$6,000
5

Beds

3.0

Baths

3,359

Sq.Ft.

10264 LOVE STORY STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 64 N PARK AVENUE Winter Garden, FL MLS# O6394825
$5,995
4

Beds

4.0

Baths

2,225

Sq.Ft.

64 N PARK AVENUE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 9240 WOODCRANE DRIVE Winter Garden, FL MLS# O6396748
$5,499
5

Beds

4.0

Baths

3,760

Sq.Ft.

9240 WOODCRANE DRIVE

Winter Garden, FL

Courtesy of HAMPTON & HAMPTON MGMT LEASING

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

1,037

Estimated median home price

$609,990
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 - 300K100
$300K - 400K80
$400K - 500K140
$500K - 600K165
$600K - 700K128
$700K - 800K120
$800K - 900K85
$900K - 1M76
$1M - Max120

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family712
Townhouse139
Condo144
Commercial10
Rental214
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 5/20/2026)

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 5/21/2026.