View 13341 PONTOON ROAD Winter Garden, FL MLS# S5150810
$2,650
3

Beds

2.1

Baths

1,814

Sq.Ft.

13341 PONTOON ROAD

Winter Garden, FL

View Address not provided Winter Garden, FL MLS# O6418382
$2,650
3

Beds

2.1

Baths

1,451

Sq.Ft.

Address not provided

Winter Garden, FL

View 18197 CIDER MILL LANE Winter Garden, FL MLS# O6420189
  • New Construction with Virtual Tour
1 of 61
$2,650
3

Beds

2.1

Baths

1,567

Sq.Ft.

18197 CIDER MILL LANE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 12007 HOLYSTONE STREET Winter Garden, FL MLS# O6421376
  • New Construction with Virtual Tour
1 of 32
$2,650
3

Beds

2.1

Baths

1,568

Sq.Ft.

12007 HOLYSTONE STREET

Winter Garden, FL

Courtesy of MR VARGAS PROPERTY MANAGEMENT LLC
View 15381 HONEYBELL DRIVE Winter Garden, FL MLS# O6420906
$2,650
4

Beds

3.0

Baths

2,034

Sq.Ft.

15381 HONEYBELL DRIVE

Winter Garden, FL

View 15811 TOLLINGTON ALLEY Winter Garden, FL MLS# O6422177
  • Recently Listed with Virtual Tour
1 of 30
$2,625
3

Beds

2.1

Baths

1,688

Sq.Ft.

15811 TOLLINGTON ALLEY

Winter Garden, FL

View 13519 SAGESTONE DRIVE Winter Garden, FL MLS# O6364941
  • New Construction with Virtual Tour
1 of 37
$2,600
3

Beds

2.1

Baths

1,567

Sq.Ft.

13519 SAGESTONE DRIVE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 1221 PRIORY CIRCLE Winter Garden, FL MLS# O6397929
$2,600
3

Beds

2.1

Baths

1,675

Sq.Ft.

1221 PRIORY CIRCLE

Winter Garden, FL

View 16347 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# S5149540
$2,600
3

Beds

2.1

Baths

1,793

Sq.Ft.

16347 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

View 9496 BAUER ALLEY Winter Garden, FL MLS# O6417010
  • New Construction with Virtual Tour
1 of 23
$2,600
3

Beds

2.1

Baths

1,567

Sq.Ft.

9496 BAUER ALLEY

Winter Garden, FL

View 15555 HONEYBELL DRIVE Winter Garden, FL MLS# O6418371
$2,600
3

Beds

2.1

Baths

1,584

Sq.Ft.

15555 HONEYBELL DRIVE

Winter Garden, FL

View 13453 SAGESTONE DRIVE Winter Garden, FL MLS# O6421534
$2,600
3

Beds

2.1

Baths

1,567

Sq.Ft.

13453 SAGESTONE DRIVE

Winter Garden, FL

Courtesy of MR VARGAS PROPERTY MANAGEMENT LLC
View 16258 MERRY ALLEY Winter Garden, FL MLS# O6383652
  • New Construction with Virtual Tour
1 of 24
$2,550
3

Beds

2.1

Baths

1,683

Sq.Ft.

16258 MERRY ALLEY

Winter Garden, FL

Courtesy of POINTON REALTY INC
View 17741 JAPONICA BLOOM DRIVE Winter Garden, FL MLS# O6404413
$2,550
3

Beds

2.1

Baths

1,466

Sq.Ft.

17741 JAPONICA BLOOM DRIVE

Winter Garden, FL

View 11056 GREAT ROCK STREET Winter Garden, FL MLS# S5150368
$2,550
3

Beds

2.1

Baths

1,817

Sq.Ft.

11056 GREAT ROCK STREET

Winter Garden, FL

View Address not provided Winter Garden, FL MLS# O6421793
$2,549
4

Beds

2.1

Baths

1,606

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of TAH FLORIDA LLC
View Address not provided Winter Garden, FL MLS# O6421784
$2,519
3

Beds

2.1

Baths

1,651

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of TAH FLORIDA LLC
View 16097 PEBBLE BLUFF LOOP Winter Garden, FL MLS# O6417837
$2,500
3

Beds

2.1

Baths

1,624

Sq.Ft.

16097 PEBBLE BLUFF LOOP

Winter Garden, FL

View 11019 BOOKMARK LANE Winter Garden, FL MLS# O6424463
  • Recently Listed with Virtual Tour
1 of 28
$2,500
3

Beds

2.1

Baths

1,518

Sq.Ft.

11019 BOOKMARK LANE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 16545 BARBOURS CREEK WAY Winter Garden, FL MLS# O6427167
  • Recently Listed with Virtual Tour
1 of 19
$2,500
3

Beds

2.1

Baths

1,567

Sq.Ft.

16545 BARBOURS CREEK WAY

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

1,076

Estimated median home price

$612,805
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 - 100K1
$100K - 200K24
$200K - 300K96
$300K - 400K68
$400K - 500K156
$500K - 600K184
$600K - 700K113
$700K - 800K129
$800K - 900K104
$900K - 1M66
$1M - Max135

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family759
Townhouse143
Condo141
Commercial10
Rental221
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/27/2026)

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 7/28/2026.