View 15340 OAK APPLE COURT COURT 16B Winter Garden, FL MLS# O6419809
  • Recently Listed with Virtual Tour
1 of 42
$350,000
3

Beds

2.1

Baths

1,544

Sq.Ft.

15340 OAK APPLE COURT COURT 16B

Winter Garden, FL

View 8019 JEREMY JOSEPH ALLEY Winter Garden, FL MLS# O6415530
$400,000
3

Beds

2.1

Baths

1,696

Sq.Ft.

8019 JEREMY JOSEPH ALLEY

Winter Garden, FL

Courtesy of SAUNDERS PLAKON
View 5863 CYPRESS HILL ROAD Winter Garden, FL MLS# TB8522840
  • Recently Listed with Virtual Tour
1 of 11
$390,000
2

Beds

2.1

Baths

1,594

Sq.Ft.

5863 CYPRESS HILL ROAD

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 14501 GROVE RESORT AVENUE 3227 Winter Garden, FL MLS# S5152479
  • Recently Listed with Virtual Tour
1 of 43
$365,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 3227

Winter Garden, FL

View 12042 GRANDROSE ALLEY Winter Garden, FL MLS# S5152170
  • Recently Listed with Virtual Tour
1 of 21
$420,000
3

Beds

2.1

Baths

1,732

Sq.Ft.

12042 GRANDROSE ALLEY

Winter Garden, FL

View 15524 HONEYBELL DRIVE Winter Garden, FL MLS# O6416374
  • Recently Listed with Virtual Tour
1 of 43
$419,000
4

Beds

3.0

Baths

1,902

Sq.Ft.

15524 HONEYBELL DRIVE

Winter Garden, FL

View 13303 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5113612
  • New Construction with Virtual Tour
1 of 25
$424,990
3

Beds

2.1

Baths

1,715

Sq.Ft.

13303 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14903 DRIFTWATER DRIVE Winter Garden, FL MLS# S5151359
  • Recently Listed with Virtual Tour
1 of 59
OPEN HOUSE: Sunday 6/28 10:00 AM - 4:00 PM
$380,000
3

Beds

2.1

Baths

1,745

Sq.Ft.

14903 DRIFTWATER DRIVE

Winter Garden, FL

View 5686 CYPRESS HILL ROAD Winter Garden, FL MLS# O6410760
$422,000
3

Beds

2.1

Baths

1,712

Sq.Ft.

5686 CYPRESS HILL ROAD

Winter Garden, FL

View 16461 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6414427
$415,000
4

Beds

2.1

Baths

1,768

Sq.Ft.

16461 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

View 15511 CAMPDEN STREET Winter Garden, FL MLS# O6413461
$395,000
3

Beds

2.1

Baths

1,916

Sq.Ft.

15511 CAMPDEN STREET

Winter Garden, FL

Courtesy of SUSANA JORDAN STUTSMAN
View 420 E CYPRESS STREET Winter Garden, FL MLS# O6412414
$420,000
3

Beds

2.0

Baths

1,616

Sq.Ft.

420 E CYPRESS STREET

Winter Garden, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY
View 11025 SUSPENSE DRIVE Winter Garden, FL MLS# G5113196
$419,900
3

Beds

2.1

Baths

1,636

Sq.Ft.

11025 SUSPENSE DRIVE

Winter Garden, FL

Courtesy of SCATES REALTY & INVESTMENT PRO
View 6246 SUNNY TIME AVENUE Winter Garden, FL MLS# O6412223
  • New Construction with Virtual Tour
1 of 24
$424,490
3

Beds

2.1

Baths

1,553

Sq.Ft.

6246 SUNNY TIME AVENUE

Winter Garden, FL

View 338 WINDFORD COURT Winter Garden, FL MLS# O6413058
$330,000
3

Beds

2.0

Baths

1,050

Sq.Ft.

338 WINDFORD COURT

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 1437 SCARLET OAK LOOP Winter Garden, FL MLS# O6411620
$350,000
3

Beds

2.1

Baths

1,684

Sq.Ft.

1437 SCARLET OAK LOOP

Winter Garden, FL

View 13232 DANIELS LANDING CIRCLE Winter Garden, FL MLS# G5112999
$350,000
2

Beds

2.1

Baths

1,232

Sq.Ft.

13232 DANIELS LANDING CIRCLE

Winter Garden, FL

View 252 DANIELS POINTE DRIVE Winter Garden, FL MLS# O6410517
$375,000
3

Beds

2.0

Baths

1,345

Sq.Ft.

252 DANIELS POINTE DRIVE

Winter Garden, FL

Courtesy of THE C SMITH REAL ESTATE GROUP LLC
View 13759 GOLDEN RUSSET DRIVE Winter Garden, FL MLS# O6409757
$328,500
3

Beds

2.1

Baths

1,647

Sq.Ft.

13759 GOLDEN RUSSET DRIVE

Winter Garden, FL

View 15568 BLACKBEAD STREET Winter Garden, FL MLS# O6408861
$435,000
4

Beds

3.0

Baths

1,861

Sq.Ft.

15568 BLACKBEAD STREET

Winter Garden, FL

Courtesy of MARK SPAIN 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

1,096

Estimated median home price

$610,805
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 - 200K24
$200K - 300K92
$300K - 400K79
$400K - 500K154
$500K - 600K189
$600K - 700K125
$700K - 800K118
$800K - 900K104
$900K - 1M76
$1M - Max134

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family769
Townhouse145
Condo143
Commercial11
Rental207
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 6/27/2026)

Information deemed reliable but not guaranteed.

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 6/28/2026.

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 6/28/2026.