View 11205 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6392839
  • Recently Listed with Virtual Tour
1 of 31
$969,091
4

Beds

3.1

Baths

3,327

Sq.Ft.

11205 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 12965 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6392975
$882,932
5

Beds

4.1

Baths

3,101

Sq.Ft.

12965 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 15432 GILLIGAN COURT Winter Garden, FL MLS# O6392254
$831,000
5

Beds

4.1

Baths

3,267

Sq.Ft.

15432 GILLIGAN COURT

Winter Garden, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
The time to sell is now! THE TIME TO SELL IS NOW!
View 1001 VINSETTA CIRCLE Winter Garden, FL MLS# O6392172
  • Recently Listed
1 of 57
$870,000
6

Beds

4.0

Baths

3,988

Sq.Ft.

1001 VINSETTA CIRCLE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 650 SETTING SUN DRIVE Winter Garden, FL MLS# O6390644
  • Recently Listed with Virtual Tour
1 of 60
$740,000
5

Beds

3.0

Baths

3,605

Sq.Ft.

650 SETTING SUN DRIVE

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 13001 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6391387
  • Recently Listed with Virtual Tour
1 of 55
$750,000
4

Beds

3.1

Baths

2,858

Sq.Ft.

13001 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 17060 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5109737
  • Recently Listed with Virtual Tour
1 of 7
OPEN HOUSE: Saturday 3/28 1:00 PM - 4:00 PM
$819,391
6

Beds

4.1

Baths

3,117

Sq.Ft.

17060 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17066 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5109739
  • Recently Listed
1 of 1
OPEN HOUSE: Saturday 3/28 1:00 PM - 4:00 PM
$765,377
4

Beds

3.0

Baths

3,038

Sq.Ft.

17066 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17416 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5109744
$784,490
4

Beds

2.1

Baths

2,688

Sq.Ft.

17416 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8216 TOPSAIL PLACE Winter Garden, FL MLS# O6391155
  • Recently Listed with Virtual Tour
1 of 67
$989,000
4

Beds

3.1

Baths

3,055

Sq.Ft.

8216 TOPSAIL PLACE

Winter Garden, FL

Courtesy of REALTY ONE GROUP MVP
View 16554 RAVEN ROCK PLACE Winter Garden, FL MLS# O6390742
  • Recently Listed
1 of 58
$875,000
4

Beds

3.0

Baths

3,032

Sq.Ft.

16554 RAVEN ROCK PLACE

Winter Garden, FL

Courtesy of INDEPENDENCE REALTY GROUP LLC
View 17361 CHANNEL WAY Winter Garden, FL MLS# O6390988
  • Recently Listed with Virtual Tour
1 of 69
$850,000
4

Beds

3.1

Baths

2,782

Sq.Ft.

17361 CHANNEL WAY

Winter Garden, FL

Courtesy of PALM CIRCLE REALTY
View 8807 SONOMA COAST Winter Garden, FL MLS# O6388886
  • Recently Listed with Virtual Tour
1 of 55
$819,000
5

Beds

4.0

Baths

2,840

Sq.Ft.

8807 SONOMA COAST

Winter Garden, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 7619 LOON AVENUE Winter Garden, FL MLS# O6388917
  • Virtual Tour
1 of 66
$750,000
4

Beds

2.1

Baths

2,691

Sq.Ft.

7619 LOON AVENUE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 6243 FLOWERIND CHERRY BEND Winter Garden, FL MLS# G5109529
$946,950
6

Beds

4.0

Baths

4,236

Sq.Ft.

6243 FLOWERIND CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6063 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5109530
$832,470
5

Beds

4.1

Baths

3,076

Sq.Ft.

6063 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6039 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5109534
$859,460
5

Beds

4.1

Baths

3,076

Sq.Ft.

6039 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 3089 IRISH PEACH DRIVE Winter Garden, FL MLS# S5145627
  • Recently Listed with Virtual Tour
1 of 54
$880,500
5

Beds

4.1

Baths

3,792

Sq.Ft.

3089 IRISH PEACH DRIVE

Winter Garden, FL

Courtesy of Kissimmee - WEICHERT, REALTORS® - Hallmark Properties
View 11193 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6389839
  • Recently Listed with Virtual Tour
1 of 31
$845,651
4

Beds

3.1

Baths

3,327

Sq.Ft.

11193 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 336 COURTLEA PARK DRIVE Winter Garden, FL MLS# S5145471
$789,000
4

Beds

4.0

Baths

2,640

Sq.Ft.

336 COURTLEA PARK DRIVE

Winter Garden, FL

Courtesy of WATSON REALTY CORP.

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

941

Estimated median home price

$588,900
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

Price Count
$0 - 100K 4
$100K - 200K 12
$200K - 300K 92
$300K - 400K 79
$400K - 500K 153
$500K - 600K 160
$600K - 700K 111
$700K - 800K 91
$800K - 900K 74
$900K - 1M 60
$1M - Max 105

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 644
Townhouse 135
Condo 126
Commercial 11
Rental 229
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 3/18/2026)

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 3/24/2026.