View 1112 JUNIPER HAMMOCK COURT Winter Garden, FL MLS# O6446330
$3,200
4

Beds

2.0

Baths

2,545

Sq.Ft.

1112 JUNIPER HAMMOCK COURT

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 16546 BARBOURS CREEK WAY Winter Garden, FL MLS# O6446369
  • New Construction with Virtual Tour
1 of 17
$2,500
3

Beds

2.1

Baths

1,567

Sq.Ft.

16546 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of WENDY MORRIS REALTY
View 15014 WINDFLOWER ALLEY Winter Garden, FL MLS# O6445294
$2,450
3

Beds

2.1

Baths

1,536

Sq.Ft.

15014 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 9374 BOLSHOI ALLEY Winter Garden, FL MLS# S5158415
$2,700
3

Beds

2.1

Baths

1,684

Sq.Ft.

9374 BOLSHOI ALLEY

Winter Garden, FL

Courtesy of LEVO REAL ESTATE LLC
View 14031 LOCHEND WAY Winter Garden, FL MLS# O6445511
$2,850
4

Beds

3.0

Baths

1,850

Sq.Ft.

14031 LOCHEND WAY

Winter Garden, FL

Courtesy of BB GROUP REALTY CORP
View 1415 SHERBOURNE STREET Winter Garden, FL MLS# O6445531
$2,650
3

Beds

2.1

Baths

1,369

Sq.Ft.

1415 SHERBOURNE STREET

Winter Garden, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 13019 TOLLCROSS WAY Winter Garden, FL MLS# O6445165
  • New Construction with Virtual Tour
1 of 32
$4,800
5

Beds

5.0

Baths

2,700

Sq.Ft.

13019 TOLLCROSS WAY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 1698 JUNIPER HAMMOCK STREET Winter Garden, FL MLS# O6445580
$7,500
7

Beds

4.0

Baths

4,700

Sq.Ft.

1698 JUNIPER HAMMOCK STREET

Winter Garden, FL

Courtesy of Lake Mary - WEICHERT, REALTORS® - Hallmark Properties
View 1938 SHERBOURNE STREET Winter Garden, FL MLS# O6445680
$2,299
3

Beds

2.0

Baths

1,260

Sq.Ft.

1938 SHERBOURNE STREET

Winter Garden, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 12615 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# O6445047
$3,000
3

Beds

2.0

Baths

1,533

Sq.Ft.

12615 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

Courtesy of JC FLORIDA REALTY LLC
View 8121 ATLANTIC PUFFIN STREET Winter Garden, FL MLS# O6444353
$3,500
4

Beds

2.1

Baths

2,697

Sq.Ft.

8121 ATLANTIC PUFFIN STREET

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 7001 CULTIVATION WAY Winter Garden, FL MLS# O6444850
$2,650
3

Beds

2.1

Baths

1,735

Sq.Ft.

7001 CULTIVATION WAY

Winter Garden, FL

Courtesy of BAHIA INTERNATIONAL REALTY
View 13345 meadow Bay loop Winter Garden, FL MLS# A12095632
$3,750
4

Beds

2.0

Baths

13345 meadow Bay loop

Winter Garden, FL

Courtesy of JMP INTERNATIONAL REALTY LLC
View 5358 BOWMAN DRIVE Winter Garden, FL MLS# O6444394
$6,800
4

Beds

4.0

Baths

3,445

Sq.Ft.

5358 BOWMAN DRIVE

Winter Garden, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 15345 HARROWGATE WAY Winter Garden, FL MLS# O6444485
$2,900
3

Beds

2.1

Baths

2,193

Sq.Ft.

15345 HARROWGATE WAY

Winter Garden, FL

Courtesy of U KEY REALTY
View 14501 GROVE RESORT AVENUE 3135 Winter Garden, FL MLS# O6444573
  • Virtual Tour
1 of 20
OPEN HOUSE: Thursday 10/29 2:00 PM - 5:00 PM
$2,500
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 3135

Winter Garden, FL

Courtesy of WELCOME HOME REALTY GROUP LLC
View 9129 PINCH SHOT DRIVE Winter Garden, FL MLS# O6444194
$3,250
5

Beds

3.0

Baths

2,638

Sq.Ft.

9129 PINCH SHOT DRIVE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 12295 BRACCO STREET Winter Garden, FL MLS# G5118149
$2,750
3

Beds

2.1

Baths

1,788

Sq.Ft.

12295 BRACCO STREET

Winter Garden, FL

Courtesy of SCATES REALTY & INVESTMENT PRO
View 405 SOUTHERN PECAN CIRCLE 108 Winter Garden, FL MLS# O6444286
$1,950
2

Beds

2.0

Baths

1,152

Sq.Ft.

405 SOUTHERN PECAN CIRCLE 108

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 12462 WESTFIELD LAKES CIRCLE Winter Garden, FL MLS# O6444402
$4,300
4

Beds

3.0

Baths

2,567

Sq.Ft.

12462 WESTFIELD LAKES CIRCLE

Winter Garden, FL

Courtesy of LPT REALTY, LLC

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

972

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 - 200K35
$200K - 300K73
$300K - 400K73
$400K - 500K150
$500K - 600K164
$600K - 700K112
$700K - 800K107
$800K - 900K108
$900K - 1M50
$1M - Max99

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family665
Townhouse149
Condo120
Commercial6
Rental241
Lots and Land25
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 10/28/2026)

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 10/29/2026.