View 1444 KENNY COURT Winter Garden, FL MLS# O6448407
  • Recently Listed with Virtual Tour
1 of 29
$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
  • Recently Listed with Virtual Tour
1 of 31
$299,900
2

Beds

2.0

Baths

1,216

Sq.Ft.

15613 BOGGY OAK CIRCLE 110A

Winter Garden, FL

Courtesy of COLEDEV REAL ESTATE LLC
View 1300 EASTERN PECAN PLACE 208 Winter Garden, FL MLS# O6449034
  • Recently Listed with Virtual Tour
1 of 63
$298,500
3

Beds

2.0

Baths

1,453

Sq.Ft.

1300 EASTERN PECAN PLACE 208

Winter Garden, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 345 E MAPLE STREET Winter Garden, FL MLS# O6448590
$295,000
2

Beds

1.0

Baths

556

Sq.Ft.

345 E MAPLE STREET

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 159 9TH STREET Winter Garden, FL MLS# O6448890
  • Recently Listed with Virtual Tour
1 of 32
$369,900
3

Beds

2.0

Baths

1,188

Sq.Ft.

159 9TH STREET

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1069 MILDRED DIXON WAY Winter Garden, FL MLS# O6441839
$275,000
3

Beds

2.0

Baths

1,036

Sq.Ft.

1069 MILDRED DIXON WAY

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 1723 Winter Garden, FL MLS# S5159130
  • Recently Listed with Virtual Tour
1 of 48
$344,900
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT 1723

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 15515 CAMPDEN STREET Winter Garden, FL MLS# O6444349
$359,900
3

Beds

2.1

Baths

1,956

Sq.Ft.

15515 CAMPDEN STREET

Winter Garden, FL

Courtesy of CLOCK TOWER REALTY
View 14169 AVENUE OF THE GROVES Winter Garden, FL MLS# O6444697
$369,000
2

Beds

2.1

Baths

1,476

Sq.Ft.

14169 AVENUE OF THE GROVES

Winter Garden, FL

Courtesy of THE SIMON SIMAAN GROUP
View 1017 Priory Circle Winter Garden, FL MLS# 12763710
$350,000
3

Beds

2.1

Baths

1,625

Sq.Ft.

1017 Priory Circle

Winter Garden, FL

MRED
Courtesy of COMPASS FLORIDA LLC
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 15279 HARROWGATE WAY Winter Garden, FL MLS# O6440200
$359,900
3

Beds

2.1

Baths

1,845

Sq.Ft.

15279 HARROWGATE WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 431 SOUTHERN PECAN CIRCLE 101 Winter Garden, FL MLS# O6439215
$274,500
3

Beds

2.0

Baths

1,340

Sq.Ft.

431 SOUTHERN PECAN CIRCLE 101

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 1017 PRIORY CIRCLE Winter Garden, FL MLS# O6438757
$350,000
3

Beds

2.1

Baths

1,625

Sq.Ft.

1017 PRIORY CIRCLE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 225 1ST STREET Winter Garden, FL MLS# TB8541424
$288,000
3

Beds

1.0

Baths

1,020

Sq.Ft.

225 1ST STREET

Winter Garden, FL

Courtesy of HOMERIVER GROUP
View ARROWHEAD BOULEVARD Winter Garden, FL MLS# S5155609
$299,900
0.0

Baths

ARROWHEAD BOULEVARD

Winter Garden, FL

Courtesy of FLORIDA REALTY RESULTS 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 1327 PRIORY CIRCLE 1327 Winter Garden, FL MLS# O6434028
$368,000
3

Beds

2.1

Baths

1,650

Sq.Ft.

1327 PRIORY CIRCLE 1327

Winter Garden, FL

Courtesy of INNOVATIVE REALTY, LLC
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

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

982

Estimated median home price

$595,000
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 - 200K35
$200K - 300K74
$300K - 400K75
$400K - 500K151
$500K - 600K168
$600K - 700K113
$700K - 800K109
$800K - 900K107
$900K - 1M51
$1M - Max98

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family675
Townhouse148
Condo121
Commercial6
Rental237
Lots and Land25
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 10/27/2026)

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 10/28/2026.

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 10/28/2026.