View 14711 WINTER STAY DRIVE Winter Garden, FL MLS# O6294212
$875,000
4

Beds

3.0

Baths

2,662

Sq.Ft.

14711 WINTER STAY DRIVE

Winter Garden, FL

Courtesy of THE FLORIDA LOUNGE REALTY LLC
View 13993 TITLE WAY Winter Garden, FL MLS# O6322118
$875,000
4

Beds

3.0

Baths

3,072

Sq.Ft.

13993 TITLE WAY

Winter Garden, FL

Courtesy of GARCIA REALTY GROUP
View 15504 SANDFIELD LOOP Winter Garden, FL MLS# O6339899
$875,000
4

Beds

3.1

Baths

4,126

Sq.Ft.

15504 SANDFIELD LOOP

Winter Garden, FL

Courtesy of HOMEVEST REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 15245 BLUE PEACOCK LANE Winter Garden, FL MLS# O6345559
$875,000
4

Beds

3.1

Baths

3,225

Sq.Ft.

15245 BLUE PEACOCK LANE

Winter Garden, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 15378 GILLIGAN COURT Winter Garden, FL MLS# O6355206
$874,500
5

Beds

4.1

Baths

3,672

Sq.Ft.

15378 GILLIGAN COURT

Winter Garden, FL

Courtesy of LOKATION
View 6019 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5102292
$867,899
4

Beds

3.1

Baths

2,688

Sq.Ft.

6019 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 18037 MILLHOUSE WAY Winter Garden, FL MLS# O6359641
  • New Construction with Virtual Tour
1 of 10
$867,800
5

Beds

4.0

Baths

2,866

Sq.Ft.

18037 MILLHOUSE WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 9414 EMERALD BERRY DRIVE Winter Garden, FL MLS# O6348107
$867,000
4

Beds

3.1

Baths

2,921

Sq.Ft.

9414 EMERALD BERRY DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 15183 SERENADE DRIVE Winter Garden, FL MLS# O6336025
$860,900
7

Beds

4.0

Baths

4,438

Sq.Ft.

15183 SERENADE DRIVE

Winter Garden, FL

Courtesy of COMPLETE FLORIDA REALTY LLC
View 327 S LAKEVIEW AVENUE Winter Garden, FL MLS# G5100180
$860,000
3

Beds

3.0

Baths

2,225

Sq.Ft.

327 S LAKEVIEW AVENUE

Winter Garden, FL

Courtesy of Clermont - WEICHERT, REALTORS® - Hallmark Properties
View 1016 HUNTSPOINT STREET Winter Garden, FL MLS# O6363691
$859,900
3

Beds

2.1

Baths

2,421

Sq.Ft.

1016 HUNTSPOINT STREET

Winter Garden, FL

Courtesy of LOKATION
View 14505 BREAKWATER WAY Winter Garden, FL MLS# O6362926
$859,900
6

Beds

3.1

Baths

3,942

Sq.Ft.

14505 BREAKWATER WAY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 15093 TEA TREE DRIVE Winter Garden, FL MLS# G5102279
$852,342
6

Beds

4.1

Baths

3,412

Sq.Ft.

15093 TEA TREE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 18055 MILLHOUSE WAY Winter Garden, FL MLS# O6361609
  • New Construction with Virtual Tour
1 of 41
$852,001
5

Beds

4.0

Baths

2,866

Sq.Ft.

18055 MILLHOUSE WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 5284 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6296617
$850,805
4

Beds

3.1

Baths

3,300

Sq.Ft.

5284 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of MERITAGE HOMES OF FL REALTY
View 595 9TH STREET Winter Garden, FL MLS# O6271548
  • Virtual Tour
1 of 24
$850,000
1,204

Sq.Ft.

595 9TH STREET

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 15007 NIGHT HERON DRIVE Winter Garden, FL MLS# S5122837
$850,000
5

Beds

3.1

Baths

3,974

Sq.Ft.

15007 NIGHT HERON DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER SOLOMON
View 276 SUMMER PINE STREET Winter Garden, FL MLS# O6334729
  • New Construction with Virtual Tour
1 of 29
$850,000
5

Beds

3.0

Baths

3,147

Sq.Ft.

276 SUMMER PINE STREET

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 8124 RED CROSSBILL STREET Winter Garden, FL MLS# O6345400
$850,000
6

Beds

4.0

Baths

3,708

Sq.Ft.

8124 RED CROSSBILL STREET

Winter Garden, FL

Courtesy of REDFIN CORPORATION
View 1428 UNION CLUB DRIVE Winter Garden, FL MLS# O6351976
$850,000
4

Beds

3.1

Baths

2,548

Sq.Ft.

1428 UNION CLUB DRIVE

Winter Garden, FL

Courtesy of COMPASS FLORIDA 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

774

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 - 300K64
$300K - 400K82
$400K - 500K132
$500K - 600K123
$600K - 700K85
$700K - 800K68
$800K - 900K63
$900K - 1M49
$1M - Max94

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family502
Townhouse117
Condo110
Commercial9
Rental224
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/3/2026)

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 1/3/2026.

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 1/3/2026.