View 13562 PEARL BEACH STREET Winter Garden, FL MLS# O6362827
  • Adult Community with Virtual Tour
1 of 36
$412,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

13562 PEARL BEACH STREET

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View Address not provided Winter Garden, FL MLS# TB8453450
  • New Construction with Virtual Tour
1 of 30
$524,990
3

Beds

3.1

Baths

2,072

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View Address not provided Winter Garden, FL MLS# O6364817
$299,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of WELCOME HOME REALTY GROUP LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 15216 CHAPTER WAY Winter Garden, FL MLS# S5139219
$499,900
4

Beds

3.0

Baths

2,042

Sq.Ft.

15216 CHAPTER WAY

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 12036 HOLYSTONE STREET Winter Garden, FL MLS# S5139531
$455,000
3

Beds

2.1

Baths

1,817

Sq.Ft.

12036 HOLYSTONE STREET

Winter Garden, FL

Courtesy of NAIM REAL ESTATE LLC
View 13545 PEARL BEACH STREET Winter Garden, FL MLS# S5139428
  • Adult Community with Virtual Tour
1 of 40
$415,000
2

Beds

2.0

Baths

1,579

Sq.Ft.

13545 PEARL BEACH STREET

Winter Garden, FL

Courtesy of IMAGINATION REALTY, INC
View 14501 GROVE RESORT AVENUE 2536 Winter Garden, FL MLS# O6364192
$314,900
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 2536

Winter Garden, FL

Courtesy of MBI REALTY LLC
View 15688 ORANGE HARVEST LOOP Winter Garden, FL MLS# O6364300
$485,000
3

Beds

2.1

Baths

2,012

Sq.Ft.

15688 ORANGE HARVEST LOOP

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 634 FOSTER AVENUE Winter Garden, FL MLS# TB8451057
$285,000
2

Beds

1.0

Baths

696

Sq.Ft.

634 FOSTER AVENUE

Winter Garden, FL

Courtesy of FLAT FEE MLS REALTY
View 14227 AVENUE OF THE GROVES RUN Winter Garden, FL MLS# O6339064
$359,000
2

Beds

2.1

Baths

1,266

Sq.Ft.

14227 AVENUE OF THE GROVES RUN

Winter Garden, FL

Courtesy of CT HOMES REALTY CORPORATION
View 16180 ARBOR CREST ALLEY Winter Garden, FL MLS# A4673607
$389,000
3

Beds

2.1

Baths

1,996

Sq.Ft.

16180 ARBOR CREST ALLEY

Winter Garden, FL

Courtesy of SAVVY AVENUE, LLC
View 13266 HARBOR SHORE LANE Winter Garden, FL MLS# O6358126
$295,000
2

Beds

2.1

Baths

1,240

Sq.Ft.

13266 HARBOR SHORE LANE

Winter Garden, FL

Courtesy of LAWYERS REAL ESTATE
View 15663 KINNOW MANDARIN LANE Winter Garden, FL MLS# O6363767
$424,000
3

Beds

2.1

Baths

1,868

Sq.Ft.

15663 KINNOW MANDARIN LANE

Winter Garden, FL

Courtesy of REAL LIVING R E SOLUTIONS
View 500 TEACUP SPRINGS COURT Winter Garden, FL MLS# S5139281
$530,000
4

Beds

3.0

Baths

2,397

Sq.Ft.

500 TEACUP SPRINGS COURT

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 16125 AZURE KEY STREET Winter Garden, FL MLS# O6364171
  • Virtual Tour
1 of 49
OPEN HOUSE: Sunday 1/25 1:00 PM - 3:00 PM
$490,000
3

Beds

2.0

Baths

1,685

Sq.Ft.

16125 AZURE KEY STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 14501 GROVE RESORT AVENUE 1407 Winter Garden, FL MLS# O6362982
$299,900
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 1407

Winter Garden, FL

Courtesy of MBI REALTY LLC
View 16154 TREADWELL STREET Winter Garden, FL MLS# G5104842
$439,900
3

Beds

2.1

Baths

1,829

Sq.Ft.

16154 TREADWELL STREET

Winter Garden, FL

Courtesy of TOUCHSTONE REAL ESTATE
View 10231 MEADOW BROOK DRIVE Winter Garden, FL MLS# O6363279
  • Virtual Tour
1 of 46
OPEN HOUSE: Sunday 1/25 12:00 PM - 4:00 PM
$475,000
3

Beds

2.0

Baths

1,685

Sq.Ft.

10231 MEADOW BROOK DRIVE

Winter Garden, FL

Courtesy of A BETTER CHOICE REALTY, INC.
View 18117 CIDER MILL LANE Winter Garden, FL MLS# O6362486
  • New Construction with Virtual Tour
1 of 15
$485,500
3

Beds

2.1

Baths

1,817

Sq.Ft.

18117 CIDER MILL LANE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 16354 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6362599
$459,000
3

Beds

2.1

Baths

1,818

Sq.Ft.

16354 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

Courtesy of FOLIO 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

814

Estimated median home price

$589,945
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 - 100K7
$100K - 200K12
$200K - 300K72
$300K - 400K83
$400K - 500K142
$500K - 600K118
$600K - 700K97
$700K - 800K76
$800K - 900K67
$900K - 1M49
$1M - Max91

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family526
Townhouse129
Condo117
Commercial7
Rental239
Lots and Land33
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/22/2026)

Information deemed reliable but not guaranteed.

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

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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

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

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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

Data is updated as of 1/25/2026.

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 1/25/2026.