View 18344 OLIVER TWIST WAY Winter Garden, FL MLS# S5140531
  • Recently Listed with Virtual Tour
1 of 34
$789,990
4

Beds

3.0

Baths

2,924

Sq.Ft.

18344 OLIVER TWIST WAY

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 5983 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5102280
$789,515
5

Beds

3.0

Baths

2,879

Sq.Ft.

5983 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6019 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5104654
$789,344
4

Beds

3.1

Baths

2,688

Sq.Ft.

6019 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 9282 WOODCRANE DRIVE Winter Garden, FL MLS# TB8455422
  • Recently Listed with Virtual Tour
1 of 69
OPEN HOUSE: Sunday 1/4 1:00 PM - 3:00 PM
$789,000
4

Beds

3.1

Baths

2,650

Sq.Ft.

9282 WOODCRANE DRIVE

Winter Garden, FL

Courtesy of DOUGLAS ELLIMAN
View 9062 SONOMA COAST DRIVE Winter Garden, FL MLS# O6352763
$785,000
4

Beds

3.0

Baths

2,909

Sq.Ft.

9062 SONOMA COAST DRIVE

Winter Garden, FL

Courtesy of AAA GLOBAL VENTURES PA
View 14602 WINTER STAY DRIVE Winter Garden, FL MLS# O6287859
$780,000
4

Beds

3.1

Baths

3,433

Sq.Ft.

14602 WINTER STAY DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 12886 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6327290
  • New Construction with Virtual Tour
1 of 43
$780,000
5

Beds

4.1

Baths

3,101

Sq.Ft.

12886 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 9150 BRADLEIGH DRIVE Winter Garden, FL MLS# O6360797
$775,000
4

Beds

3.1

Baths

3,087

Sq.Ft.

9150 BRADLEIGH DRIVE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 417 S MAIN STREET Winter Garden, FL MLS# O6361513
$775,000
3

Beds

2.1

Baths

2,172

Sq.Ft.

417 S MAIN STREET

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 15075 TEA TREE DRIVE Winter Garden, FL MLS# G5102184
$773,260
4

Beds

3.0

Baths

3,038

Sq.Ft.

15075 TEA TREE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 18309 OLIVER TWIST WAY Winter Garden, FL MLS# O6310963
$770,000
5

Beds

4.0

Baths

2,832

Sq.Ft.

18309 OLIVER TWIST WAY

Winter Garden, FL

Courtesy of CORCORAN CONNECT LLC
View 16150 PARKWYN STREET Winter Garden, FL MLS# S5121096
$769,990
4

Beds

3.1

Baths

3,093

Sq.Ft.

16150 PARKWYN STREET

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 17877 PHIL C PETERS ROAD Winter Garden, FL MLS# O6328962
$765,000
3

Beds

2.0

Baths

2,501

Sq.Ft.

17877 PHIL C PETERS ROAD

Winter Garden, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 17877 PHIL C PETERS ROAD Winter Garden, FL MLS# O6328963
$765,000
Studio

Beds

0.0

Baths

17877 PHIL C PETERS ROAD

Winter Garden, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 18386 Oliver Twist WAY Winter Garden, FL MLS# O6173842
  • New Construction with Virtual Tour
1 of 36
$761,166
4

Beds

3.0

Baths

2,924

Sq.Ft.

18386 Oliver Twist WAY

Winter Garden, FL

Courtesy of D R HORTON REALTY OF CENTRAL FLORIDA LLC
View 14710 SCOTT KEY DRIVE Winter Garden, FL MLS# S5138514
$759,000
5

Beds

3.1

Baths

2,935

Sq.Ft.

14710 SCOTT KEY DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 11175 HOLLOW BAY WAY Winter Garden, FL MLS# O6367441
  • Recently Listed with Virtual Tour
1 of 30
$758,841
4

Beds

3.0

Baths

2,113

Sq.Ft.

11175 HOLLOW BAY WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 15293 NIGHT HERON DRIVE Winter Garden, FL MLS# O6350632
$755,000
5

Beds

3.1

Baths

3,956

Sq.Ft.

15293 NIGHT HERON DRIVE

Winter Garden, FL

Courtesy of RATIO REAL ESTATE, LLC
View 15807 SWEET LEMON WAY Winter Garden, FL MLS# O6361039
$752,000
5

Beds

4.0

Baths

2,867

Sq.Ft.

15807 SWEET LEMON WAY

Winter Garden, FL

Courtesy of SUNNY 365 REALTY GROUP
View 214 S MAIN STREET Winter Garden, FL MLS# G5099655
$750,000
4

Beds

4.0

Baths

2,268

Sq.Ft.

214 S MAIN STREET

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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.