View 14031 PICARD ALLEY Winter Garden, FL MLS# O6421215
$380,000
3

Beds

2.1

Baths

1,789

Sq.Ft.

14031 PICARD ALLEY

Winter Garden, FL

Courtesy of ELITE INTERNATIONAL REALTY 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 16931 RESEDA ALLEY Winter Garden, FL MLS# O6430332
$379,990
3

Beds

2.1

Baths

1,568

Sq.Ft.

16931 RESEDA ALLEY

Winter Garden, FL

Courtesy of MY REALTY GROUP, LLC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 1424 SCARLET OAK LOOP Winter Garden, FL MLS# O6436325
$379,000
3

Beds

2.1

Baths

1,737

Sq.Ft.

1424 SCARLET OAK LOOP

Winter Garden, FL

Courtesy of TEAMCONNECT REALTY LLC
View 14989 APOLLO BOND DRIVE Winter Garden, FL MLS# O6378685
$375,000
3

Beds

2.1

Baths

1,789

Sq.Ft.

14989 APOLLO BOND DRIVE

Winter Garden, FL

Courtesy of THE C SMITH REAL ESTATE GROUP LLC
View 5618 WATER ROSE ROAD Winter Garden, FL MLS# O6400788
$375,000
3

Beds

2.1

Baths

1,755

Sq.Ft.

5618 WATER ROSE ROAD

Winter Garden, FL

Courtesy of SUNNY 365 REALTY GROUP
View 14169 AVENUE OF THE GROVES Winter Garden, FL MLS# O6444697
  • Recently Listed with Virtual Tour
1 of 41
$375,000
2

Beds

2.1

Baths

1,476

Sq.Ft.

14169 AVENUE OF THE GROVES

Winter Garden, FL

Courtesy of THE SIMON SIMAAN GROUP
View 884 KLONDIKE STREET Winter Garden, FL MLS# O6389922
$372,500
4

Beds

2.0

Baths

1,485

Sq.Ft.

884 KLONDIKE STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14903 DRIFTWATER DRIVE Winter Garden, FL MLS# S5151359
$370,000
3

Beds

2.1

Baths

1,745

Sq.Ft.

14903 DRIFTWATER DRIVE

Winter Garden, FL

Courtesy of NUMBER 1 BROKER, LLC
View 14501 GROVE RESORT AVENUE 3535 Winter Garden, FL MLS# S5138632
$369,990
2

Beds

2.0

Baths

1,434

Sq.Ft.

14501 GROVE RESORT AVENUE 3535

Winter Garden, FL

Courtesy of SACKS REALTY GROUP, INC.
View 15510 CAMPDEN STREET Winter Garden, FL MLS# S5154448
$369,900
3

Beds

2.1

Baths

1,924

Sq.Ft.

15510 CAMPDEN STREET

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
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 13765 GOLDEN RUSSET DRIVE Winter Garden, FL MLS# O6428789
$365,000
3

Beds

2.1

Baths

1,600

Sq.Ft.

13765 GOLDEN RUSSET DRIVE

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
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 15515 CAMPDEN STREET Winter Garden, FL MLS# O6444349
  • Recently Listed with Virtual Tour
1 of 48
$359,900
3

Beds

2.1

Baths

1,956

Sq.Ft.

15515 CAMPDEN STREET

Winter Garden, FL

Courtesy of CLOCK TOWER REALTY
View 14501 GROVE RESORT AVENUE 2129 Winter Garden, FL MLS# O6311969
$359,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 2129

Winter Garden, FL

Courtesy of UNITED REALTY GROUP INC
View 14501 Grove Resort Ave 2129 Winter Garden, FL MLS# A11950039
$359,000
3

Beds

2.0

Baths

14501 Grove Resort Ave 2129

Winter Garden, FL

Courtesy of UNITED REALTY GROUP INC
View 14501 GROVE RESORT AVENUE 3619 Winter Garden, FL MLS# O6374077
$355,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3619

Winter Garden, FL

Courtesy of REALTY ONE GROUP ESTATES
View 5863 CYPRESS HILL ROAD Winter Garden, FL MLS# TB8522840
$355,000
2

Beds

2.1

Baths

1,594

Sq.Ft.

5863 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of ZENITH REALTY FIRM LLC
View 13855 GOLDEN RUSSET DRIVE Winter Garden, FL MLS# G5116589
$355,000
2

Beds

2.1

Baths

1,652

Sq.Ft.

13855 GOLDEN RUSSET DRIVE

Winter Garden, FL

Courtesy of ERA GRIZZARD 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

979

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 - 200K34
$200K - 300K69
$300K - 400K77
$400K - 500K158
$500K - 600K161
$600K - 700K105
$700K - 800K109
$800K - 900K102
$900K - 1M60
$1M - Max103

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family670
Townhouse152
Condo119
Commercial6
Rental226
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 10/9/2026)

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 10/11/2026.

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 10/11/2026.