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 12144 STONELEIGH ALLEY Winter Garden, FL MLS# O6384252
$2,600
3

Beds

2.0

Baths

1,588

Sq.Ft.

12144 STONELEIGH ALLEY

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 15915 MARINA BAY DRIVE Winter Garden, FL MLS# O6390934
$2,600
3

Beds

2.1

Baths

1,804

Sq.Ft.

15915 MARINA BAY DRIVE

Winter Garden, FL

Courtesy of JULIAN PROPERTIES, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 12032 HOLYSTONE STREET Winter Garden, FL MLS# O6401473
$2,600
3

Beds

2.1

Baths

1,568

Sq.Ft.

12032 HOLYSTONE STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 5417 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# O6403708
$2,600
3

Beds

2.1

Baths

1,506

Sq.Ft.

5417 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
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

Courtesy of DEFINITIVE GROUP LLC
View 7254 DUXBURY LN Winter Garden, FL MLS# O6407524
  • Recently Listed with Virtual Tour
1 of 18
$2,600
2

Beds

2.1

Baths

1,752

Sq.Ft.

7254 DUXBURY LN

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 16587 BARBOURS CREEK WAY Winter Garden, FL MLS# S5146245
  • New Construction with Virtual Tour
1 of 55
$2,590
3

Beds

2.1

Baths

1,567

Sq.Ft.

16587 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of WATSON REALTY CORP.
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 10030 SALT POINT DRIVE Winter Garden, FL MLS# O6393755
$2,550
3

Beds

2.1

Baths

1,568

Sq.Ft.

10030 SALT POINT DRIVE

Winter Garden, FL

Courtesy of CT HOMES REALTY CORPORATION
View 13323 PONTOON ROAD Winter Garden, FL MLS# S5147574
$2,550
3

Beds

2.1

Baths

1,451

Sq.Ft.

13323 PONTOON ROAD

Winter Garden, FL

Courtesy of LA ROSA REALTY INTERNACIONAL L
View 525 GARDEN HEIGHTS DR Winter Garden, FL MLS# O6407564
$2,550
3

Beds

2.0

Baths

1,693

Sq.Ft.

525 GARDEN HEIGHTS DR

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 16917 TESLA ALLEY Winter Garden, FL MLS# O6392623
$2,500
3

Beds

2.1

Baths

1,568

Sq.Ft.

16917 TESLA ALLEY

Winter Garden, FL

Courtesy of YORK MILLS REALTY LLC
View 16374 TURNING TIDE WAY Winter Garden, FL MLS# O6397885
$2,500
3

Beds

2.1

Baths

1,568

Sq.Ft.

16374 TURNING TIDE WAY

Winter Garden, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 16039 JUNIPER INLET ALLEY Winter Garden, FL MLS# O6408214
  • Recently Listed with Virtual Tour
1 of 21
$2,500
3

Beds

2.1

Baths

1,568

Sq.Ft.

16039 JUNIPER INLET ALLEY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 14454 PRUNNINGWOOD PLACE Winter Garden, FL MLS# S5150579
  • Recently Listed with Virtual Tour
1 of 30
$2,500
2

Beds

2.1

Baths

1,157

Sq.Ft.

14454 PRUNNINGWOOD PLACE

Winter Garden, FL

Courtesy of RIVA REALTY GROUP LLC
View 8019 JEREMY JOSEPH ALLEY 8019 Winter Garden, FL MLS# O6379718
  • New Construction with Virtual Tour
1 of 23
$2,495
3

Beds

2.1

Baths

1,691

Sq.Ft.

8019 JEREMY JOSEPH ALLEY 8019

Winter Garden, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
View 2040 PORTCASTLE CIRCLE Winter Garden, FL MLS# O6397668
$2,495
4

Beds

2.1

Baths

1,606

Sq.Ft.

2040 PORTCASTLE CIRCLE

Winter Garden, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 17207 OCEAN HILL DRIVE Winter Garden, FL MLS# O6392177
$2,490
3

Beds

2.0

Baths

1,692

Sq.Ft.

17207 OCEAN HILL DRIVE

Winter Garden, FL

Courtesy of U KEY REALTY
View 15146 WINDFLOWER ALLEY Winter Garden, FL MLS# O6386816
$2,450
3

Beds

2.1

Baths

1,536

Sq.Ft.

15146 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE

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

1,040

Estimated median home price

$609,306
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 - 200K25
$200K - 300K96
$300K - 400K79
$400K - 500K142
$500K - 600K172
$600K - 700K127
$700K - 800K114
$800K - 900K87
$900K - 1M72
$1M - Max125

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family718
Townhouse136
Condo143
Commercial10
Rental214
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 5/29/2026)

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 5/29/2026.