View 418 WESTPOINT GARDEN CIRCLE Winter Garden, FL MLS# O6369108
  • Recently Listed with Virtual Tour
1 of 5
$2,250
3

Beds

2.1

Baths

1,588

Sq.Ft.

418 WESTPOINT GARDEN CIRCLE

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 15000 STRATUS LOOP B1 Winter Garden, FL MLS# O6308743
$2,284
2

Beds

2.0

Baths

1,023

Sq.Ft.

15000 STRATUS LOOP B1

Winter Garden, FL

Courtesy of THE APARTMENT BROTHERS LLC
View 316 SOUTHERN PECAN CIRCLE 205 Winter Garden, FL MLS# O6363602
$2,350
3

Beds

2.0

Baths

1,453

Sq.Ft.

316 SOUTHERN PECAN CIRCLE 205

Winter Garden, FL

Courtesy of MBA REALTY GROUP, INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 7054 BROOMSHEDGE TRAIL TRAIL Winter Garden, FL MLS# S5139900
$2,370
2

Beds

2.1

Baths

1,200

Sq.Ft.

7054 BROOMSHEDGE TRAIL TRAIL

Winter Garden, FL

Courtesy of LA ROSA REALTY KISSIMMEE
View 15000 STRATUS LOOP B3 Winter Garden, FL MLS# O6308749
$2,372
2

Beds

2.0

Baths

1,055

Sq.Ft.

15000 STRATUS LOOP B3

Winter Garden, FL

Courtesy of THE APARTMENT BROTHERS LLC
View 1150 CHASE DRIVE Winter Garden, FL MLS# O6367573
$2,375
4

Beds

2.0

Baths

1,852

Sq.Ft.

1150 CHASE DRIVE

Winter Garden, FL

Courtesy of PREMIER MANAGEMENT GROUP INC
View 399 WINTER NELLIS CIRCLE Winter Garden, FL MLS# O6364179
$2,400
3

Beds

2.1

Baths

1,592

Sq.Ft.

399 WINTER NELLIS CIRCLE

Winter Garden, FL

Courtesy of JAMIESON PROPERTIES, INC.
View 13352 HARBOR SHORE LANE 13352 Winter Garden, FL MLS# O6368717
  • Recently Listed with Virtual Tour
1 of 18
$2,400
2

Beds

2.1

Baths

1,234

Sq.Ft.

13352 HARBOR SHORE LANE 13352

Winter Garden, FL

Courtesy of FLORIDA PRESTIGIOUS HOMES INC
View 12028 HOLYSTONE STREET 12028 Winter Garden, FL MLS# O6338923
$2,449
3

Beds

2.1

Baths

1,451

Sq.Ft.

12028 HOLYSTONE STREET 12028

Winter Garden, FL

Courtesy of ORLANDO KEY REALTY LLC
View 1118 PRIORY CIRCLE Winter Garden, FL MLS# O6349927
$2,450
3

Beds

2.1

Baths

1,625

Sq.Ft.

1118 PRIORY CIRCLE

Winter Garden, FL

Courtesy of JOY ESTATE ENTERPRISE INC
View 15002 WINDFLOWER ALLEY Winter Garden, FL MLS# O6360807
$2,475
3

Beds

2.1

Baths

1,536

Sq.Ft.

15002 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 13078 SERENE GLADE ROAD Winter Garden, FL MLS# O6344472
$2,499
3

Beds

2.1

Baths

1,644

Sq.Ft.

13078 SERENE GLADE ROAD

Winter Garden, FL

Courtesy of KRESSLER REAL ESTATE
View 1519 PRIORY CIRCLE Winter Garden, FL MLS# O6332308
$2,500
3

Beds

2.1

Baths

1,916

Sq.Ft.

1519 PRIORY CIRCLE

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 15074 WINDFLOWER ALLEY Winter Garden, FL MLS# O6357962
  • New Construction with Virtual Tour
1 of 18
$2,500
3

Beds

2.1

Baths

1,536

Sq.Ft.

15074 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of PRISTINE INTERNATIONAL REALTY LLC
View 17592 NORTHLAKE GROVE DRIVE Winter Garden, FL MLS# S5140376
$2,500
3

Beds

3.0

Baths

1,577

Sq.Ft.

17592 NORTHLAKE GROVE DRIVE

Winter Garden, FL

Courtesy of CELEBRATION RENTAL GROUP
View Address not provided Winter Garden, FL MLS# TB8457506
  • Recently Listed with Virtual Tour
1 of 18
$2,549
4

Beds

2.1

Baths

2,013

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of TAH FLORIDA LLC
View 1933 PORTCASTLE CIRCLE Winter Garden, FL MLS# O6351607
$2,550
3

Beds

2.1

Baths

1,857

Sq.Ft.

1933 PORTCASTLE CIRCLE

Winter Garden, FL

Courtesy of RED DOOR INVESTMENT GRP LLC
View 1529 SPRING RIDGE CIRCLE Winter Garden, FL MLS# O6361655
$2,550
4

Beds

2.0

Baths

1,897

Sq.Ft.

1529 SPRING RIDGE CIRCLE

Winter Garden, FL

Courtesy of WATSON REALTY CORP
View 13483 SAGESTONE DRIVE Winter Garden, FL MLS# O6365207
$2,550
3

Beds

2.1

Baths

1,568

Sq.Ft.

13483 SAGESTONE DRIVE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 12071 HOLYSTONE STREET Winter Garden, FL MLS# O6362698
$2,590
3

Beds

2.1

Baths

1,814

Sq.Ft.

12071 HOLYSTONE STREET

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION

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

763

Estimated median home price

$585,000
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 - 100K6
$100K - 200K10
$200K - 300K64
$300K - 400K80
$400K - 500K135
$500K - 600K115
$600K - 700K82
$700K - 800K70
$800K - 900K62
$900K - 1M48
$1M - Max91

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family491
Townhouse119
Condo107
Commercial9
Rental223
Lots and Land33
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/6/2026)

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 1/7/2026.