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 14031 PICARD ALLEY Winter Garden, FL MLS# O6421215
$349,000
3

Beds

2.1

Baths

1,789

Sq.Ft.

14031 PICARD ALLEY

Winter Garden, FL

Courtesy of ELITE INTERNATIONAL REALTY INC
View 14501 GROVE RESORT 1723 Winter Garden, FL MLS# S5159130
$344,900
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT 1723

Winter Garden, FL

Courtesy of LPT REALTY, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 14501 GROVE RESORT AVENUE 2623 Winter Garden, FL MLS# O6329943
$340,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 2623

Winter Garden, FL

Courtesy of MBI REALTY LLC
View 15625 BOGGY OAK CIRCLE 108B Winter Garden, FL MLS# G5112579
$335,000
3

Beds

2.1

Baths

1,419

Sq.Ft.

15625 BOGGY OAK CIRCLE 108B

Winter Garden, FL

Courtesy of SCATES REALTY & INVESTMENT PRO
View 14501 GROVE RESORT AVE 3701 Winter Garden, FL MLS# O6433198
$335,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVE 3701

Winter Garden, FL

Courtesy of MRI REALTY GROUP
View 483 PENNSYLVANIA AVENUE Winter Garden, FL MLS# O6398208
$334,000
2

Beds

2.0

Baths

1,008

Sq.Ft.

483 PENNSYLVANIA AVENUE

Winter Garden, FL

Courtesy of STIRLING INTERNATIONAL REAL ES
View 14766 PEEKSKILL DRIVE Winter Garden, FL MLS# O6440912
$332,500
2

Beds

2.1

Baths

1,406

Sq.Ft.

14766 PEEKSKILL DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 14066 AVENUE OF THE GROVES Winter Garden, FL MLS# O6447744
$329,000
2

Beds

2.1

Baths

1,077

Sq.Ft.

14066 AVENUE OF THE GROVES

Winter Garden, FL

Courtesy of RAZZANI INTERNATIONAL REALTY
View 14501 GROVE RESORT AVENUE 1220 Winter Garden, FL MLS# O6279431
$325,890
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 1220

Winter Garden, FL

Courtesy of MBI REALTY LLC
View 14501 GROVE RESORT AVENUE 3205 Winter Garden, FL MLS# O6157343
$325,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 3205

Winter Garden, FL

Courtesy of ALL SELLERS & BUYERS REALTY INC
View Address not provided Winter Garden, FL MLS# O6390273
$325,000
1,700

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of Clermont - WEICHERT, REALTORS® - Hallmark Properties
View 14501 GROVE RESORT AVENUE 1614 Winter Garden, FL MLS# O6398376
$325,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 1614

Winter Garden, FL

Courtesy of LIVE MVRK LLC
View 338 WINDFORD COURT Winter Garden, FL MLS# O6413058
$325,000
3

Beds

2.0

Baths

1,050

Sq.Ft.

338 WINDFORD COURT

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 13232 DANIELS LANDING CIRCLE Winter Garden, FL MLS# G5112999
$325,000
2

Beds

2.1

Baths

1,232

Sq.Ft.

13232 DANIELS LANDING CIRCLE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 14501 GROVE RESORT AVENUE 2342 Winter Garden, FL MLS# O6432384
$319,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 2342

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
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 13349 HARBOR SHORE LANE Winter Garden, FL MLS# G5114466
$307,000
2

Beds

2.1

Baths

1,236

Sq.Ft.

13349 HARBOR SHORE LANE

Winter Garden, FL

Courtesy of LIST NOW REALTY, LLC
View 14501 GROVE RESORT AVENUE 1105 Winter Garden, FL MLS# O6365470
$304,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 1105

Winter Garden, FL

Courtesy of MBI REALTY LLC
View 14501 GROVE RESORT AVENUE 3109 Winter Garden, FL MLS# O6386655
$299,900
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 3109

Winter Garden, FL

Courtesy of MBI 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

947

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

PriceCount
$0 - 100K1
$100K - 200K37
$200K - 300K73
$300K - 400K67
$400K - 500K143
$500K - 600K146
$600K - 700K115
$700K - 800K102
$800K - 900K103
$900K - 1M54
$1M - Max106

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family648
Townhouse142
Condo116
Commercial5
Rental249
Lots and Land28
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home1
Farms0

(Data as of 11/12/2026)

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 11/12/2026.

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 11/12/2026.