View 17546 LAKE STAR ROAD Winter Garden, FL MLS# S5157675
$6,900
5

Beds

4.1

Baths

3,767

Sq.Ft.

17546 LAKE STAR ROAD

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
View 17018 CLEAR MIND ALLEY Winter Garden, FL MLS# O6441101
$3,000
3

Beds

2.1

Baths

1,845

Sq.Ft.

17018 CLEAR MIND ALLEY

Winter Garden, FL

Courtesy of ALLUX REAL ESTATE LLC
View 16271 PEBBLE BLUFF LOOP Winter Garden, FL MLS# O6442568
$3,200
3

Beds

2.1

Baths

2,170

Sq.Ft.

16271 PEBBLE BLUFF LOOP

Winter Garden, FL

Courtesy of LIFESTYLE INTERNATIONAL REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 15382 ARCADIA BLUFF LOOP Winter Garden, FL MLS# O6439386
$3,595
4

Beds

3.1

Baths

2,441

Sq.Ft.

15382 ARCADIA BLUFF LOOP

Winter Garden, FL

Courtesy of CT HOMES REALTY CORPORATION
View 16477 SILVER BROOK WAY Winter Garden, FL MLS# O6441878
$6,000
5

Beds

4.1

Baths

3,889

Sq.Ft.

16477 SILVER BROOK WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 6466 OLD CARRIAGE ROAD Winter Garden, FL MLS# O6441884
$2,950
3

Beds

2.1

Baths

2,024

Sq.Ft.

6466 OLD CARRIAGE ROAD

Winter Garden, FL

Courtesy of THE FLORIDA LOUNGE REALTY LLC
View 17025 HAGGERTY HOLLOW Winter Garden, FL MLS# O6441499
  • New Construction with Virtual Tour
1 of 26
$2,700
3

Beds

2.1

Baths

1,644

Sq.Ft.

17025 HAGGERTY HOLLOW

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 17013 HAGGERTY HOLLOW Winter Garden, FL MLS# O6441500
  • New Construction with Virtual Tour
1 of 30
$2,750
3

Beds

2.1

Baths

1,744

Sq.Ft.

17013 HAGGERTY HOLLOW

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 17334 BEACHGRASS ALLEY Winter Garden, FL MLS# O6441006
  • New Construction with Virtual Tour
1 of 56
$3,100
3

Beds

2.1

Baths

1,983

Sq.Ft.

17334 BEACHGRASS ALLEY

Winter Garden, FL

Courtesy of ALLIVE REALTY
View 17049 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# O6440509
  • New Construction with Virtual Tour
1 of 25
$2,850
3

Beds

2.0

Baths

1,772

Sq.Ft.

17049 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 5506 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# O6440733
$3,200
5

Beds

3.1

Baths

2,369

Sq.Ft.

5506 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 16311 LAKELET ALLEY Winter Garden, FL MLS# O6441007
$2,400
3

Beds

2.1

Baths

1,567

Sq.Ft.

16311 LAKELET ALLEY

Winter Garden, FL

Courtesy of EAST PEARL REALTY
View 18228 OLIVER TWIST WAY Winter Garden, FL MLS# S5157296
  • New Construction with Virtual Tour
1 of 14
$3,400
4

Beds

4.0

Baths

2,722

Sq.Ft.

18228 OLIVER TWIST WAY

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 1239 DUNBROOKE STREET Winter Garden, FL MLS# O6440566
$2,995
4

Beds

2.0

Baths

2,047

Sq.Ft.

1239 DUNBROOKE STREET

Winter Garden, FL

Courtesy of PREMIUM PROPERTIES R.E SERVICE
View 1627 SHERBOURNE STREET Winter Garden, FL MLS# O6440760
$2,500
3

Beds

2.0

Baths

1,365

Sq.Ft.

1627 SHERBOURNE STREET

Winter Garden, FL

Courtesy of ROMAN REALTY GROUP, LLC
View 9049 BRADLEIGH DRIVE Winter Garden, FL MLS# O6438635
$4,500
5

Beds

4.1

Baths

3,258

Sq.Ft.

9049 BRADLEIGH DRIVE

Winter Garden, FL

Courtesy of MNT INTERNATIONAL
View 15543 WATERLEIGH COVE DRIVE Winter Garden, FL MLS# O6438571
$2,799
3

Beds

2.0

Baths

1,921

Sq.Ft.

15543 WATERLEIGH COVE DRIVE

Winter Garden, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 502 DUNBAR AVENUE Winter Garden, FL MLS# O6438802
$1,399
2

Beds

1.0

Baths

816

Sq.Ft.

502 DUNBAR AVENUE

Winter Garden, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 17736 PORTER ROAD Winter Garden, FL MLS# O6439463
  • New Construction with Virtual Tour
1 of 27
$2,995
3

Beds

2.1

Baths

1,764

Sq.Ft.

17736 PORTER ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 15134 WINDFLOWER ALLEY Winter Garden, FL MLS# S5157036
$2,300
2

Beds

2.1

Baths

1,195

Sq.Ft.

15134 WINDFLOWER ALLEY

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

963

Estimated median home price

$599,000
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 - 200K36
$200K - 300K73
$300K - 400K70
$400K - 500K149
$500K - 600K163
$600K - 700K110
$700K - 800K107
$800K - 900K108
$900K - 1M46
$1M - Max100

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family657
Townhouse148
Condo120
Commercial6
Rental236
Lots and Land25
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 10/30/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 10/31/2026.