View 14838 DRIFTWATER DRIVE Winter Garden, FL MLS# O6454429
  • Recently Listed with Virtual Tour
1 of 48
$389,900
3

Beds

2.1

Baths

1,748

Sq.Ft.

14838 DRIFTWATER DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 1351 & 1359 AVALON ROAD Winter Garden, FL MLS# TB8565873
  • Recently Listed with Virtual Tour
1 of 7
$265,000
0.0

Baths

1351 & 1359 AVALON ROAD

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View Address not provided Winter Garden, FL MLS# O6456209
  • Recently Listed with Virtual Tour
1 of 6
$155,000
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 14501 GROVE RESORT AVENUE 1516 Winter Garden, FL MLS# S5160899
  • Recently Listed with Virtual Tour
1 of 11
$283,800
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 1516

Winter Garden, FL

Courtesy of SACKS REALTY GROUP, INC.
View 271 DANIELS POINTE DRIVE Winter Garden, FL MLS# O6455616
  • Recently Listed with Virtual Tour
1 of 37
$355,000
3

Beds

2.0

Baths

1,300

Sq.Ft.

271 DANIELS POINTE DRIVE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 215 S WOODLAND STREET Winter Garden, FL MLS# O6455445
$425,000
4

Beds

2.0

Baths

1,685

Sq.Ft.

215 S WOODLAND STREET

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 15316 OAK APPLE COURT B Winter Garden, FL MLS# O6455495
$285,000
3

Beds

2.1

Baths

1,544

Sq.Ft.

15316 OAK APPLE COURT B

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 6266 SUNNY TIME AVENUE Winter Garden, FL MLS# O6454896
  • Recently Listed with Virtual Tour
1 of 26
$429,890
3

Beds

2.1

Baths

1,683

Sq.Ft.

6266 SUNNY TIME AVENUE

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 14501 GROVE RESORT AVENUE 3618 Winter Garden, FL MLS# S5160518
  • Recently Listed with Virtual Tour
1 of 12
$430,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 3618

Winter Garden, FL

Courtesy of SACKS REALTY GROUP, INC.
View Address not provided Winter Garden, FL MLS# O6454154
  • Recently Listed with Virtual Tour
1 of 25
$239,900
3

Beds

1.0

Baths

814

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 159 9TH STREET Winter Garden, FL MLS# O6453622
  • Recently Listed with Virtual Tour
1 of 40
$369,900
3

Beds

2.0

Baths

1,188

Sq.Ft.

159 9TH STREET

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 14501 GROVE RESORT AVENUE 3239 Winter Garden, FL MLS# S5160379
  • Recently Listed with Virtual Tour
1 of 37
$165,000
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 3239

Winter Garden, FL

Courtesy of FLARE PROPERTIES LLC
View 13537 SPLASHING ISLA DRIVE Winter Garden, FL MLS# TB8560424
  • Recently Listed with Virtual Tour
1 of 66
$430,000
3

Beds

2.0

Baths

1,574

Sq.Ft.

13537 SPLASHING ISLA DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS-PLANT CITY
View 5705 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# O6452416
  • Recently Listed with Virtual Tour
1 of 26
$399,900
3

Beds

2.0

Baths

1,751

Sq.Ft.

5705 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

Courtesy of MARK SPAIN REAL ESTATE
View 87 WINDTREE LANE K Winter Garden, FL MLS# O6450975
  • Recently Listed with Virtual Tour
1 of 19
$189,000
2

Beds

2.0

Baths

918

Sq.Ft.

87 WINDTREE LANE K

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 10606 WORDS DRIVE Winter Garden, FL MLS# O6448083
$420,000
4

Beds

2.1

Baths

1,863

Sq.Ft.

10606 WORDS DRIVE

Winter Garden, FL

Courtesy of C23 REALTY LLC
View 14501 GROVE RESORT AVENUE 1440 Winter Garden, FL MLS# S5159866
$159,999
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 1440

Winter Garden, FL

Courtesy of TEAM DONOVAN
View 1444 KENNY COURT Winter Garden, FL MLS# O6448407
$350,000
3

Beds

2.0

Baths

1,352

Sq.Ft.

1444 KENNY COURT

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
View 15613 BOGGY OAK CIRCLE 110A Winter Garden, FL MLS# O6450253
$279,000
2

Beds

2.0

Baths

1,216

Sq.Ft.

15613 BOGGY OAK CIRCLE 110A

Winter Garden, FL

Courtesy of COLEDEV REAL ESTATE LLC
View 1210 BRANDY LAKE VIEW CIRCLE Winter Garden, FL MLS# O6449523
$425,000
3

Beds

2.0

Baths

1,502

Sq.Ft.

1210 BRANDY LAKE VIEW CIRCLE

Winter Garden, FL

Courtesy of HOMEVEST REALTY

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

943

Estimated median home price

$609,481
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 - 100K2
$100K - 200K36
$200K - 300K73
$300K - 400K67
$400K - 500K142
$500K - 600K148
$600K - 700K114
$700K - 800K104
$800K - 900K99
$900K - 1M54
$1M - Max104

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family644
Townhouse141
Condo118
Commercial5
Rental244
Lots and Land27
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home1
Farms0

(Data as of 11/10/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Weichert Realtors are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. 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.

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Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Copyright © 2026 Midwest Real Estate Data LLC.

Data is updated as of 11/11/2026.

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 11/11/2026.