View 15811 TOLLINGTON ALLEY Winter Garden, FL MLS# O6422177
$2,625
3

Beds

2.1

Baths

1,688

Sq.Ft.

15811 TOLLINGTON ALLEY

Winter Garden, FL

View 1914 SHERBOURNE STREET Winter Garden, FL MLS# O6432877
$2,625
3

Beds

2.1

Baths

1,356

Sq.Ft.

1914 SHERBOURNE STREET

Winter Garden, FL

Courtesy of THE LISTING REAL ESTATE MANAGEMENT
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

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
$2,600
3

Beds

2.1

Baths

1,568

Sq.Ft.

12007 HOLYSTONE STREET

Winter Garden, FL

Courtesy of MR VARGAS PROPERTY MANAGEMENT LLC
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 1944 PORTCASTLE CIRCLE Winter Garden, FL MLS# O6421978
$2,600
3

Beds

2.1

Baths

1,857

Sq.Ft.

1944 PORTCASTLE CIRCLE

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 1241 PRIORY CIRCLE Winter Garden, FL MLS# S5153101
$2,600
3

Beds

2.1

Baths

1,884

Sq.Ft.

1241 PRIORY CIRCLE

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 9321 JAYWOOD ROAD Winter Garden, FL MLS# S5154781
  • Recently Listed with Virtual Tour
1 of 15
$2,600
3

Beds

2.0

Baths

1,685

Sq.Ft.

9321 JAYWOOD ROAD

Winter Garden, FL

View 13882 TITLE WAY Winter Garden, FL MLS# S5155410
  • Recently Listed with Virtual Tour
1 of 23
$2,590
3

Beds

2.1

Baths

1,518

Sq.Ft.

13882 TITLE WAY

Winter Garden, FL

Courtesy of K REALTY
View 16347 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# S5149540
$2,550
3

Beds

2.1

Baths

1,793

Sq.Ft.

16347 PRAIRIE SCHOOL 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

Courtesy of MULTI CHOICE REALTY LLC
View 16237 QUIET VISTA DRIVE Winter Garden, FL MLS# O6436637
  • Recently Listed with Virtual Tour
1 of 19
$2,550
3

Beds

2.1

Baths

1,568

Sq.Ft.

16237 QUIET VISTA DRIVE

Winter Garden, FL

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
$2,500
3

Beds

2.1

Baths

1,518

Sq.Ft.

11019 BOOKMARK LANE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 1841 EAGLE BEAM ROAD Winter Garden, FL MLS# O6437392
  • Recently Listed with Virtual Tour
1 of 18
$2,500
3

Beds

2.1

Baths

1,342

Sq.Ft.

1841 EAGLE BEAM ROAD

Winter Garden, FL

View 1470 BROKEN OAK DRIVE 27C Winter Garden, FL MLS# O6428198
$2,450
3

Beds

2.1

Baths

1,699

Sq.Ft.

1470 BROKEN OAK DRIVE 27C

Winter Garden, FL

View Address not provided Winter Garden, FL MLS# O6421793
$2,409
4

Beds

2.1

Baths

1,606

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of TAH FLORIDA LLC
View 15000 STRATUS LOOP B2 Winter Garden, FL MLS# O6308749
$2,375
2

Beds

2.0

Baths

1,130

Sq.Ft.

15000 STRATUS LOOP B2

Winter Garden, FL

View 13527 DANIELS LANDING CIRCLE Winter Garden, FL MLS# S5148507
$2,300
3

Beds

2.1

Baths

1,365

Sq.Ft.

13527 DANIELS LANDING CIRCLE

Winter Garden, FL

Courtesy of Kissimmee - WEICHERT, REALTORS® - Hallmark Properties
View 218 WINTER NELLIS CIRCLE Winter Garden, FL MLS# O6436614
  • Recently Listed with Virtual Tour
1 of 38
$2,295
3

Beds

2.1

Baths

1,647

Sq.Ft.

218 WINTER NELLIS CIRCLE

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

1,029

Estimated median home price

$608,000
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 - 200K22
$200K - 300K89
$300K - 400K78
$400K - 500K153
$500K - 600K168
$600K - 700K112
$700K - 800K113
$800K - 900K112
$900K - 1M62
$1M - Max119

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family715
Townhouse145
Condo133
Commercial9
Rental188
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/29/2026)

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 8/29/2026.