View 208 3RD STREET Winter Garden, FL MLS# O6435263
$435,000
0.0

Baths

208 3RD STREET

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 208 3RD STREET Winter Garden, FL MLS# O6435284
$435,000
8

Beds

3.0

Baths

1,750

Sq.Ft.

208 3RD STREET

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 300 ERON WAY 1 Winter Garden, FL MLS# O6434883
  • Virtual Tour
1 of 30
$224,000
2

Beds

2.0

Baths

840

Sq.Ft.

300 ERON WAY 1

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 27 WINDTREE LANE 102 Winter Garden, FL MLS# G5116462
$219,990
2

Beds

2.0

Baths

918

Sq.Ft.

27 WINDTREE LANE 102

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15038 WINDFLOWER ALLEY Winter Garden, FL MLS# O6434050
$440,000
3

Beds

2.1

Baths

1,536

Sq.Ft.

15038 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 1221 PRIORY CIRCLE Winter Garden, FL MLS# S5155802
$380,000
3

Beds

2.1

Baths

1,675

Sq.Ft.

1221 PRIORY CIRCLE

Winter Garden, FL

Courtesy of AROD PARTNERS REALTY
View 10648 WORDS DRIVE Winter Garden, FL MLS# O6433944
$418,400
3

Beds

2.1

Baths

1,636

Sq.Ft.

10648 WORDS DRIVE

Winter Garden, FL

Courtesy of INDEPENDENCE REALTY GROUP LLC
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 16306 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# O6433563
$398,000
3

Beds

2.1

Baths

1,792

Sq.Ft.

16306 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 14501 GROVE RESORT AVENUE 3215 Winter Garden, FL MLS# S5155653
$199,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 3215

Winter Garden, FL

Courtesy of TEAM DONOVAN
View 16534 BARBOURS CREEK WAY Winter Garden, FL MLS# O6433686
  • New Construction with Virtual Tour
1 of 18
$454,990
3

Beds

2.1

Baths

1,817

Sq.Ft.

16534 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA 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 844 KLONDIKE STREET Winter Garden, FL MLS# O6431531
$199,999
1

Beds

1.0

Baths

1,300

Sq.Ft.

844 KLONDIKE STREET

Winter Garden, FL

Courtesy of ALVARENGA REALTY LLC
View 15014 WINDFLOWER ALLEY Winter Garden, FL MLS# O6433433
$424,990
3

Beds

2.1

Baths

1,536

Sq.Ft.

15014 WINDFLOWER ALLEY

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
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
View 233 SOUTHERN PECAN CIRCLE 101 Winter Garden, FL MLS# G5116347
$219,900
2

Beds

1.0

Baths

966

Sq.Ft.

233 SOUTHERN PECAN CIRCLE 101

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 8013 BASILICA LANE Winter Garden, FL MLS# O6432456
$410,000
3

Beds

2.1

Baths

1,860

Sq.Ft.

8013 BASILICA LANE

Winter Garden, FL

Courtesy of MARKET CONNECT REALTY LLC
View 14501 GROVE RESORT AVE 1707 Winter Garden, FL MLS# O6432157
$239,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVE 1707

Winter Garden, FL

Courtesy of HOPKEY REALTY
View 17723 JAPONICA BLOOM DRIVE Winter Garden, FL MLS# O6432610
$394,999
3

Beds

2.1

Baths

1,584

Sq.Ft.

17723 JAPONICA BLOOM DRIVE

Winter Garden, FL

Courtesy of Longwood - WEICHERT, REALTORS® - Hallmark Properties

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

997

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 - 200K33
$200K - 300K75
$300K - 400K78
$400K - 500K150
$500K - 600K172
$600K - 700K114
$700K - 800K115
$800K - 900K105
$900K - 1M55
$1M - Max99

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family690
Townhouse150
Condo119
Commercial6
Rental230
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 10/19/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

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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 10/20/2026.

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 10/20/2026.