View 10180 LOVE STORY STREET Winter Garden, FL MLS# A4657855
$680,000
4

Beds

3.0

Baths

2,662

Sq.Ft.

10180 LOVE STORY STREET

Winter Garden, FL

Courtesy of FLORIDA MORNING REALTY LLC
View 8060 BOWERY DRIVE Winter Garden, FL MLS# O6359786
$680,000
5

Beds

3.0

Baths

3,013

Sq.Ft.

8060 BOWERY DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS LEGACY REALTY
View 2022 TILLMAN AVE Winter Garden, FL MLS# O6363253
$680,000
4

Beds

4.0

Baths

2,981

Sq.Ft.

2022 TILLMAN AVE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 47 OAK STREET Winter Garden, FL MLS# O6370459
  • Recently Listed with Virtual Tour
1 of 7
$679,000
Studio

Beds

0.0

Baths

47 OAK STREET

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 15143 KIRSTY ALLEY Winter Garden, FL MLS# O6344886
$678,000
5

Beds

3.1

Baths

2,934

Sq.Ft.

15143 KIRSTY ALLEY

Winter Garden, FL

Courtesy of ARION REALTY
View 6333 WILD PERSIMMON WAY Winter Garden, FL MLS# G5102272
$677,702
3

Beds

3.1

Baths

2,515

Sq.Ft.

6333 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 10031 BEDTIME STORY DRIVE Winter Garden, FL MLS# O6329801
$675,000
4

Beds

4.0

Baths

2,722

Sq.Ft.

10031 BEDTIME STORY DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 14246 CREEKBED CIRCLE Winter Garden, FL MLS# O6341945
$675,000
4

Beds

3.0

Baths

2,418

Sq.Ft.

14246 CREEKBED CIRCLE

Winter Garden, FL

Courtesy of LEGACY PLUS REALTY
View 5937 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5102276
$674,475
4

Beds

2.1

Baths

2,235

Sq.Ft.

5937 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6007 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5105905
$674,475
4

Beds

2.1

Baths

2,235

Sq.Ft.

6007 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15456 GILLIGAN COURT Winter Garden, FL MLS# A4660262
$674,000
3

Beds

3.0

Baths

2,571

Sq.Ft.

15456 GILLIGAN COURT

Winter Garden, FL

Courtesy of NEXTHOME CASA BELLA ELITE
View 6315 WILD PERSIMMON WAY Winter Garden, FL MLS# G5105013
$668,990
4

Beds

3.0

Baths

2,102

Sq.Ft.

6315 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6351 WILD PERSIMMON WAY Winter Garden, FL MLS# G5102275
$666,985
4

Beds

2.1

Baths

2,802

Sq.Ft.

6351 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17305 BEACHGRASS ALLEY Winter Garden, FL MLS# O6365499
$665,935
4

Beds

3.0

Baths

2,543

Sq.Ft.

17305 BEACHGRASS ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 2510 BLACK LAKE BOULEVARD Winter Garden, FL MLS# O6330638
$665,000
4

Beds

3.0

Baths

3,022

Sq.Ft.

2510 BLACK LAKE BOULEVARD

Winter Garden, FL

Courtesy of TEAMCONNECT REALTY LLC
View 5290 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6358664
$664,000
4

Beds

3.0

Baths

2,080

Sq.Ft.

5290 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 16271 SILVER GROVE BLVD Winter Garden, FL MLS# O6299810
  • New Construction with Virtual Tour
1 of 46
$660,000
4

Beds

2.1

Baths

2,093

Sq.Ft.

16271 SILVER GROVE BLVD

Winter Garden, FL

Courtesy of CELEBRITY GLOBAL REALTY LLC
View 15518 SUNQUAT DRIVE Winter Garden, FL MLS# O6334225
$660,000
4

Beds

3.1

Baths

2,502

Sq.Ft.

15518 SUNQUAT DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 12626 CLEAR SAPPHIRE DRIVE Winter Garden, FL MLS# O6365821
$660,000
4

Beds

3.0

Baths

2,500

Sq.Ft.

12626 CLEAR SAPPHIRE DRIVE

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
View 15388 ARCADIA BLUFF LOOP Winter Garden, FL MLS# O6361770
$659,990
3

Beds

4.1

Baths

2,640

Sq.Ft.

15388 ARCADIA BLUFF LOOP

Winter Garden, FL

Courtesy of DOUBLE M GROUP COMPANY

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

753

Estimated median home price

$589,000
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 - 100K6
$100K - 200K8
$200K - 300K60
$300K - 400K80
$400K - 500K131
$500K - 600K117
$600K - 700K82
$700K - 800K68
$800K - 900K61
$900K - 1M48
$1M - Max92

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family489
Townhouse115
Condo104
Commercial9
Rental221
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/4/2026)

Information deemed reliable but not guaranteed.

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.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

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

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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.

Data is updated as of 1/5/2026.

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 1/5/2026.