View 14807 WINTER STAY DRIVE Winter Garden, FL MLS# O6434655
  • Recently Listed with Virtual Tour
1 of 67
$6,500
5

Beds

4.0

Baths

3,856

Sq.Ft.

14807 WINTER STAY DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 9321 JAYWOOD ROAD Winter Garden, FL MLS# S5154781
  • Recently Listed with Virtual Tour
1 of 15
$2,800
3

Beds

2.0

Baths

1,685

Sq.Ft.

9321 JAYWOOD ROAD

Winter Garden, FL

View 9566 BOLERO ROAD Winter Garden, FL MLS# O6434084
  • Recently Listed with Virtual Tour
1 of 38
$5,200
5

Beds

3.1

Baths

3,910

Sq.Ft.

9566 BOLERO ROAD

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 9652 AMBER CHESTNUT WAY Winter Garden, FL MLS# O6434085
$3,000
4

Beds

2.1

Baths

1,948

Sq.Ft.

9652 AMBER CHESTNUT WAY

Winter Garden, FL

Courtesy of FL PRO BROKERS LLC
View 14610 SETON CREEK BOULEVARD Winter Garden, FL MLS# O6434094
$3,100
3

Beds

2.1

Baths

1,916

Sq.Ft.

14610 SETON CREEK BOULEVARD

Winter Garden, FL

Courtesy of FL PRO BROKERS LLC
View 6230 SUNNY TIME AVENUE Winter Garden, FL MLS# O6434114
  • Recently Listed with Virtual Tour
1 of 22
$3,000
3

Beds

2.1

Baths

1,770

Sq.Ft.

6230 SUNNY TIME AVENUE

Winter Garden, FL

Courtesy of FL PRO BROKERS LLC
View 531 CLANCY STREET Winter Garden, FL MLS# O6434348
  • Recently Listed
1 of 41
$2,900
4

Beds

2.1

Baths

2,208

Sq.Ft.

531 CLANCY STREET

Winter Garden, FL

View 13613 LARSEN LANE Winter Garden, FL MLS# O6434112
  • Recently Listed with Virtual Tour
1 of 24
$3,400
5

Beds

4.0

Baths

3,812

Sq.Ft.

13613 LARSEN LANE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 92 WINDTREE LANE L Winter Garden, FL MLS# O6434051
  • Recently Listed with Virtual Tour
1 of 10
$1,650
2

Beds

2.0

Baths

918

Sq.Ft.

92 WINDTREE LANE L

Winter Garden, FL

View 11045 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6433890
  • Recently Listed with Virtual Tour
1 of 25
$3,900
4

Beds

3.0

Baths

2,113

Sq.Ft.

11045 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC
View 12761 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6434282
  • Recently Listed with Virtual Tour
1 of 17
$1,475
1

Beds

1.0

Baths

500

Sq.Ft.

12761 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 15347 GILLIGAN COURT Winter Garden, FL MLS# S5155641
  • Recently Listed with Virtual Tour
1 of 9
$1,600
1

Beds

1.0

Baths

620

Sq.Ft.

15347 GILLIGAN COURT

Winter Garden, FL

Courtesy of MOSAIC PARTNERS GROUP
View 16576 BARBOURS CREEK WAY Winter Garden, FL MLS# O6433577
  • Recently Listed with Virtual Tour
1 of 93
$2,950
3

Beds

2.1

Baths

1,567

Sq.Ft.

16576 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 16588 BARBOURS CREEK WAY Winter Garden, FL MLS# O6433580
  • Recently Listed with Virtual Tour
1 of 93
$2,950
3

Beds

2.1

Baths

1,567

Sq.Ft.

16588 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 16570 BARBOURS CREEK WAY Winter Garden, FL MLS# O6433586
  • Recently Listed with Virtual Tour
1 of 93
$2,950
3

Beds

2.1

Baths

1,567

Sq.Ft.

16570 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 5923 CYPRESS HILL ROAD Winter Garden, FL MLS# O6433661
  • Recently Listed with Virtual Tour
1 of 23
$3,100
4

Beds

2.1

Baths

2,466

Sq.Ft.

5923 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View Address not provided Winter Garden, FL MLS# O6433852
  • Recently Listed with Virtual Tour
1 of 16
$2,999
4

Beds

2.0

Baths

2,022

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of TAH FLORIDA LLC
View 8313 TOPSAIL PLACE Winter Garden, FL MLS# O6433253
$3,600
3

Beds

2.0

Baths

2,170

Sq.Ft.

8313 TOPSAIL PLACE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 225 SOUTHERN PECAN CIRCLE 205 Winter Garden, FL MLS# O6433382
  • Recently Listed with Virtual Tour
1 of 28
$2,200
2

Beds

2.0

Baths

1,264

Sq.Ft.

225 SOUTHERN PECAN CIRCLE 205

Winter Garden, FL

View 15155 CANOE PLACE Winter Garden, FL MLS# O6433426
  • Recently Listed with Virtual Tour
1 of 38
$6,000
5

Beds

4.1

Baths

4,045

Sq.Ft.

15155 CANOE PLACE

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

1,018

Estimated median home price

$611,805
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 - 100K2
$100K - 200K21
$200K - 300K89
$300K - 400K78
$400K - 500K147
$500K - 600K164
$600K - 700K110
$700K - 800K117
$800K - 900K108
$900K - 1M63
$1M - Max119

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family702
Townhouse144
Condo136
Commercial9
Rental177
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 8/19/2026)

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 8/19/2026.