View 14488 WHITTRIDGE DRIVE Winter Garden, FL MLS# O6404890
$3,000
4

Beds

3.0

Baths

2,328

Sq.Ft.

14488 WHITTRIDGE DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 14384 BRAEMAR STREET Winter Garden, FL MLS# O6400691
$2,800
3

Beds

2.1

Baths

2,000

Sq.Ft.

14384 BRAEMAR STREET

Winter Garden, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 16347 PRAIRIE SCHOOL DRIVE Winter Garden, FL MLS# S5149540
$2,600
3

Beds

2.1

Baths

1,793

Sq.Ft.

16347 PRAIRIE SCHOOL DRIVE

Winter Garden, FL

Courtesy of DEFINITIVE GROUP LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2827 SANCTUARY LANE Winter Garden, FL MLS# O6403747
$4,500
3

Beds

2.1

Baths

2,178

Sq.Ft.

2827 SANCTUARY LANE

Winter Garden, FL

Courtesy of GARCIA REALTY GROUP
View 5417 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# O6403708
$2,600
3

Beds

2.1

Baths

1,506

Sq.Ft.

5417 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 9158 SONOMA COAST DRIVE Winter Garden, FL MLS# TB8502828
$3,495
4

Beds

3.0

Baths

2,117

Sq.Ft.

9158 SONOMA COAST DRIVE

Winter Garden, FL

Courtesy of 7 BLUE LLC
View 502 S HIGHLAND AVENUE Winter Garden, FL MLS# O6403053
$2,800
3

Beds

1.0

Baths

2,102

Sq.Ft.

502 S HIGHLAND AVENUE

Winter Garden, FL

Courtesy of NEW SOLUTIONS REALTY INC
View 13071 INKWELL ALLEY Winter Garden, FL MLS# S5148709
$2,650
4

Beds

3.0

Baths

2,042

Sq.Ft.

13071 INKWELL ALLEY

Winter Garden, FL

View 17877 PHIL C PETERS RD Winter Garden, FL MLS# O6402176
$4,299
3

Beds

2.0

Baths

2,501

Sq.Ft.

17877 PHIL C PETERS RD

Winter Garden, FL

Courtesy of REIS E SILVA REALTY GROUP LLC
View 143 SOUTHERN PECAN CIRCLE 201 Winter Garden, FL MLS# O6402229
$2,350
3

Beds

2.0

Baths

1,453

Sq.Ft.

143 SOUTHERN PECAN CIRCLE 201

Winter Garden, FL

View 508 VARSITY STREET Winter Garden, FL MLS# O6401722
$1,695
2

Beds

1.0

Baths

780

Sq.Ft.

508 VARSITY STREET

Winter Garden, FL

Courtesy of CAPITAL REALTY GROUP FLORIDA
View 13527 DANIELS LANDING CIRCLE Winter Garden, FL MLS# S5148507
$2,300
3

Beds

2.1

Baths

1,365

Sq.Ft.

13527 DANIELS LANDING CIRCLE

Winter Garden, FL

Courtesy of Kissimmee - WEICHERT, REALTORS® - Hallmark Properties
View 16350 HAMLIN VIEW STREET Winter Garden, FL MLS# O6400898
  • New Construction with Virtual Tour
1 of 67
$2,950
3

Beds

2.1

Baths

1,644

Sq.Ft.

16350 HAMLIN VIEW STREET

Winter Garden, FL

Courtesy of WEBB FLORIDA REALTY LLC
View 15363 HAMLIN PARK DRIVE Winter Garden, FL MLS# O6401538
$3,200
3

Beds

3.1

Baths

1,936

Sq.Ft.

15363 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 12506 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# S5148369
$1,600
1

Beds

1.0

Baths

2,900

Sq.Ft.

12506 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 6148 WATERSIDE ISLAND LANE Winter Garden, FL MLS# O6398414
$3,500
5

Beds

3.1

Baths

3,468

Sq.Ft.

6148 WATERSIDE ISLAND LANE

Winter Garden, FL

Courtesy of JHY REALTY INVESTMENTS, LLC
View Address not provided Winter Garden, FL MLS# O6398448
$3,400
4

Beds

3.1

Baths

2,570

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of ORLANDO SUNSHINE REALTY
View 215 CENTER STREET 225/227 Winter Garden, FL MLS# O6398301
  • New Construction with Virtual Tour
1 of 19
$32,400
2,304

Sq.Ft.

215 CENTER STREET 225/227

Winter Garden, FL

Courtesy of PREICO REALTY SERVICES INC
View 7564 BISHOP SQUARE DRIVE Winter Garden, FL MLS# O6398382
$3,299
3

Beds

2.0

Baths

2,300

Sq.Ft.

7564 BISHOP SQUARE DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 595 9TH STREET Winter Garden, FL MLS# O6398340
  • Virtual Tour
1 of 17
$34,800
1,204

Sq.Ft.

595 9TH STREET

Winter Garden, FL

Courtesy of ENGEL & VOELKERS LAKELAND

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

1,073

Estimated median home price

$614,000
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 - 200K24
$200K - 300K95
$300K - 400K77
$400K - 500K141
$500K - 600K188
$600K - 700K123
$700K - 800K114
$800K - 900K100
$900K - 1M75
$1M - Max135

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family758
Townhouse133
Condo145
Commercial11
Rental204
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/1/2026)

Information deemed reliable but not guaranteed.

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 7/1/2026.