View 9107 GRAND ISLAND WAY Winter Garden, FL MLS# O6391117
$499,900
3

Beds

2.1

Baths

2,082

Sq.Ft.

9107 GRAND ISLAND WAY

Winter Garden, FL

Courtesy of FHG REALTY, LLC
View 107 TRADITIONS DRIVE Winter Garden, FL MLS# S5145650
$474,975
3

Beds

2.0

Baths

1,582

Sq.Ft.

107 TRADITIONS DRIVE

Winter Garden, FL

Courtesy of WATSON REALTY CORP
View 680 DUNBAR AVENUE Winter Garden, FL MLS# O6389210
  • New Construction with Virtual Tour
1 of 6
$465,000
4

Beds

2.0

Baths

1,713

Sq.Ft.

680 DUNBAR AVENUE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 884 KLONDIKE STREET Winter Garden, FL MLS# O6389922
$375,000
4

Beds

2.0

Baths

1,485

Sq.Ft.

884 KLONDIKE STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6530 PASTURELANDS PLACE Winter Garden, FL MLS# O6390459
$479,999
3

Beds

2.1

Baths

2,067

Sq.Ft.

6530 PASTURELANDS PLACE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 8156 WOOD SAGE DRIVE Winter Garden, FL MLS# V4947783
  • Adult Community with Virtual Tour
1 of 42
$449,000
3

Beds

2.1

Baths

1,853

Sq.Ft.

8156 WOOD SAGE DRIVE

Winter Garden, FL

Courtesy of APARO-GRIFFIN PROPERTIES INC
View 16149 WIND VIEW LANE Winter Garden, FL MLS# O6389892
$495,000
3

Beds

2.1

Baths

2,036

Sq.Ft.

16149 WIND VIEW LANE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 13837 LANYARD WAY Winter Garden, FL MLS# O6388993
  • Virtual Tour
1 of 38
$485,000
3

Beds

2.1

Baths

1,994

Sq.Ft.

13837 LANYARD WAY

Winter Garden, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 2621 SHIREHALL LANE Winter Garden, FL MLS# O6386585
$475,000
3

Beds

2.0

Baths

1,960

Sq.Ft.

2621 SHIREHALL LANE

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 15182 SUNRISE GROVE COURT Winter Garden, FL MLS# O6382211
$384,990
3

Beds

2.1

Baths

1,844

Sq.Ft.

15182 SUNRISE GROVE COURT

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 7007 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6388545
$465,000
3

Beds

2.1

Baths

1,845

Sq.Ft.

7007 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 14095 TITLE WAY Winter Garden, FL MLS# O6382795
  • Virtual Tour
1 of 38
$420,000
3

Beds

2.1

Baths

1,628

Sq.Ft.

14095 TITLE WAY

Winter Garden, FL

Courtesy of ROMAN'S PRO REALTY LLC
View 5706 CYPRESS HILL ROAD Winter Garden, FL MLS# O6386620
$460,000
3

Beds

2.1

Baths

1,712

Sq.Ft.

5706 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16563 BARBOURS CREEK WAY Winter Garden, FL MLS# O6386283
  • New Construction with Virtual Tour
1 of 14
$414,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16563 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 18167 CIDER MILL LANE Winter Garden, FL MLS# O6386278
  • New Construction with Virtual Tour
1 of 15
$469,990
3

Beds

2.1

Baths

1,817

Sq.Ft.

18167 CIDER MILL LANE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 13291 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5108893
  • New Construction with Virtual Tour
1 of 53
$428,405
3

Beds

2.1

Baths

1,644

Sq.Ft.

13291 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8113 RED STOPPER LANE Winter Garden, FL MLS# O6386525
$444,000
3

Beds

2.1

Baths

1,725

Sq.Ft.

8113 RED STOPPER LANE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 648 ORANGE BELT LOOP Winter Garden, FL MLS# S5144591
$499,990
3

Beds

2.1

Baths

1,688

Sq.Ft.

648 ORANGE BELT LOOP

Winter Garden, FL

Courtesy of CORCORAN CONNECT LLC
View 1401 N FULLERS CROSS ROAD Winter Garden, FL MLS# O6385497
$395,000
Studio

Beds

0.0

Baths

1401 N FULLERS CROSS ROAD

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 14058 FRASIER STREET Winter Garden, FL MLS# V4947394
$459,000
4

Beds

2.1

Baths

1,996

Sq.Ft.

14058 FRASIER STREET

Winter Garden, FL

Courtesy of EXP 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

1,046

Estimated median home price

$615,000
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

Price Count
$0 - 100K 1
$100K - 200K 23
$200K - 300K 89
$300K - 400K 79
$400K - 500K 146
$500K - 600K 171
$600K - 700K 129
$700K - 800K 115
$800K - 900K 92
$900K - 1M 72
$1M - Max 129

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 731
Townhouse 139
Condo 136
Commercial 11
Rental 199
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 1
Farms 0

(Data as of 6/8/2026)

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 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 6/8/2026.

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 6/8/2026.