View 2015 SANDY GARDEN LANE Winter Garden, FL MLS# O6370025
  • Recently Listed with Virtual Tour
1 of 39
$799,900
4

Beds

4.1

Baths

3,871

Sq.Ft.

2015 SANDY GARDEN LANE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 5074 BREEZY ACRES STREET Winter Garden, FL MLS# O6369788
  • Recently Listed with Virtual Tour
1 of 56
OPEN HOUSE: Sunday 1/4 7:00 AM - 8:00 AM
$900,000
7

Beds

4.1

Baths

4,720

Sq.Ft.

5074 BREEZY ACRES STREET

Winter Garden, FL

Courtesy of NEW HEIGHTS REALTY GROUP
View 873 GAYLE MILL DRIVE Winter Garden, FL MLS# O6368964
$940,000
4

Beds

3.1

Baths

2,677

Sq.Ft.

873 GAYLE MILL DRIVE

Winter Garden, FL

Courtesy of DENIZ REALTY PARTNERS LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 18344 OLIVER TWIST WAY Winter Garden, FL MLS# S5140531
  • Recently Listed with Virtual Tour
1 of 34
$789,990
4

Beds

3.0

Baths

2,924

Sq.Ft.

18344 OLIVER TWIST WAY

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 17309 MARSH ROAD Winter Garden, FL MLS# O6369686
  • Recently Listed with Virtual Tour
1 of 7
$800,000
Studio

Beds

0.0

Baths

17309 MARSH ROAD

Winter Garden, FL

Courtesy of UPSIDE REAL ESTATE INC
View 10551 PETRILLO WAY Winter Garden, FL MLS# O6368778
  • Recently Listed with Virtual Tour
1 of 91
$960,000
5

Beds

4.1

Baths

3,358

Sq.Ft.

10551 PETRILLO WAY

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 17309 MARSH ROAD Winter Garden, FL MLS# O6369367
  • Recently Listed with Virtual Tour
1 of 24
$800,000
4

Beds

2.0

Baths

1,685

Sq.Ft.

17309 MARSH ROAD

Winter Garden, FL

Courtesy of UPSIDE REAL ESTATE INC
View Address not provided Winter Garden, FL MLS# O6367937
  • Recently Listed with Virtual Tour
1 of 38
$810,000
3

Beds

2.1

Baths

2,278

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of EMPIRE NETWORK REALTY
View 18049 MILLHOUSE WAY Winter Garden, FL MLS# O6367428
  • Recently Listed with Virtual Tour
1 of 31
$880,200
4

Beds

3.1

Baths

3,327

Sq.Ft.

18049 MILLHOUSE WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 11145 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6367437
  • Recently Listed with Virtual Tour
1 of 31
$912,271
4

Beds

3.2

Baths

3,327

Sq.Ft.

11145 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 11175 HOLLOW BAY WAY Winter Garden, FL MLS# O6367441
  • Recently Listed with Virtual Tour
1 of 30
$758,841
4

Beds

3.0

Baths

2,113

Sq.Ft.

11175 HOLLOW BAY WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 17561 SEIDNER ROAD Winter Garden, FL MLS# G5105438
$900,000
4

Beds

4.0

Baths

2,850

Sq.Ft.

17561 SEIDNER ROAD

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 14505 BREAKWATER WAY Winter Garden, FL MLS# O6362926
$859,900
6

Beds

3.1

Baths

3,942

Sq.Ft.

14505 BREAKWATER WAY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 15372 GILLIGAN COURT Winter Garden, FL MLS# O6367059
  • Recently Listed with Virtual Tour
1 of 34
$884,500
4

Beds

3.1

Baths

2,781

Sq.Ft.

15372 GILLIGAN COURT

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 13214 DENDY WAY Winter Garden, FL MLS# O6366658
  • New Construction with Virtual Tour
1 of 71
$920,000
5

Beds

4.1

Baths

3,719

Sq.Ft.

13214 DENDY WAY

Winter Garden, FL

Courtesy of KICANTO REALTY
View 9282 WOODCRANE DRIVE Winter Garden, FL MLS# TB8455422
  • Recently Listed with Virtual Tour
1 of 69
OPEN HOUSE: Sunday 1/4 1:00 PM - 3:00 PM
$789,000
4

Beds

3.1

Baths

2,650

Sq.Ft.

9282 WOODCRANE DRIVE

Winter Garden, FL

Courtesy of DOUGLAS ELLIMAN
View 14282 CREEKBED CIRCLE Winter Garden, FL MLS# O6365928
  • Recently Listed with Virtual Tour
1 of 45
$939,900
4

Beds

4.0

Baths

3,479

Sq.Ft.

14282 CREEKBED CIRCLE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 6152 MERIWETHER CRESCENT Winter Garden, FL MLS# O6365054
$814,900
5

Beds

3.1

Baths

3,367

Sq.Ft.

6152 MERIWETHER CRESCENT

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 14931 LEBEAU LOOP Winter Garden, FL MLS# O6364989
$849,000
4

Beds

3.1

Baths

2,832

Sq.Ft.

14931 LEBEAU LOOP

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 13374 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5105157
  • New Construction with Virtual Tour
1 of 28
$814,990
5

Beds

4.0

Baths

3,076

Sq.Ft.

13374 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC

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

767

Estimated median home price

$587,000
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 - 100K7
$100K - 200K8
$200K - 300K64
$300K - 400K82
$400K - 500K131
$500K - 600K121
$600K - 700K85
$700K - 800K67
$800K - 900K61
$900K - 1M49
$1M - Max92

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family496
Townhouse117
Condo110
Commercial10
Rental223
Lots and Land30
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/2/2026)

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 1/3/2026.