View 15142 MASTHEAD LANDING CIRCLE Winter Garden, FL MLS# O6421619
$3,350
4

Beds

3.0

Baths

1,886

Sq.Ft.

15142 MASTHEAD LANDING CIRCLE

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 16125 PARKWYN STREET Winter Garden, FL MLS# O6421567
$3,200
3

Beds

2.1

Baths

2,020

Sq.Ft.

16125 PARKWYN STREET

Winter Garden, FL

View 2205 WINTERMERE POINTE DRIVE Winter Garden, FL MLS# O6420747
$3,850
5

Beds

3.0

Baths

3,747

Sq.Ft.

2205 WINTERMERE POINTE DRIVE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 200 SOUTHERN PECAN CIRCLE 203 Winter Garden, FL MLS# S5152842
$1,830
2

Beds

2.0

Baths

1,276

Sq.Ft.

200 SOUTHERN PECAN CIRCLE 203

Winter Garden, FL

View 884 KLONDIKE STREET Winter Garden, FL MLS# O6416439
$2,800
4

Beds

2.0

Baths

1,485

Sq.Ft.

884 KLONDIKE STREET

Winter Garden, FL

View 14654 WATOWAN ALLEY Winter Garden, FL MLS# TB8523613
$3,000
3

Beds

2.1

Baths

1,911

Sq.Ft.

14654 WATOWAN ALLEY

Winter Garden, FL

Courtesy of DOUGLAS ELLIMAN
View 720 PARKMONT PLACE Winter Garden, FL MLS# O6419049
$3,700
3

Beds

2.0

Baths

2,210

Sq.Ft.

720 PARKMONT PLACE

Winter Garden, FL

Courtesy of WINTER GARDEN REAL ESTATE
View Address not provided Winter Garden, FL MLS# O6418382
$2,650
3

Beds

2.1

Baths

1,451

Sq.Ft.

Address not provided

Winter Garden, FL

View 10224 ATWATER BAY DRIVE Winter Garden, FL MLS# S5152340
$4,195
5

Beds

3.1

Baths

3,227

Sq.Ft.

10224 ATWATER BAY DRIVE

Winter Garden, FL

Courtesy of NAIM REAL ESTATE LLC
View 806 LOST GROVE CIRCLE Winter Garden, FL MLS# S5152166
$3,495
5

Beds

3.0

Baths

3,462

Sq.Ft.

806 LOST GROVE CIRCLE

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 16097 PEBBLE BLUFF LOOP Winter Garden, FL MLS# O6417837
$2,500
3

Beds

2.1

Baths

1,624

Sq.Ft.

16097 PEBBLE BLUFF LOOP

Winter Garden, FL

View 273 AVALON ROAD Winter Garden, FL MLS# G5113807
  • Virtual Tour
1 of 32
$2,850
4

Beds

2.0

Baths

2,459

Sq.Ft.

273 AVALON ROAD

Winter Garden, FL

View 15501 HAMLIN PARK DRIVE Winter Garden, FL MLS# S5152008
$3,200
3

Beds

3.1

Baths

2,072

Sq.Ft.

15501 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of CELEBRATION RENTAL GROUP
View 2158 WINTERMERE POINTE DRIVE Winter Garden, FL MLS# O6417265
$3,600
4

Beds

3.0

Baths

2,966

Sq.Ft.

2158 WINTERMERE POINTE DRIVE

Winter Garden, FL

View 10126 SALT POINT DRIVE Winter Garden, FL MLS# S5151937
$2,750
3

Beds

2.1

Baths

1,888

Sq.Ft.

10126 SALT POINT DRIVE

Winter Garden, FL

View 9496 BAUER ALLEY Winter Garden, FL MLS# O6417010
  • New Construction with Virtual Tour
1 of 23
$2,600
3

Beds

2.1

Baths

1,567

Sq.Ft.

9496 BAUER ALLEY

Winter Garden, FL

View 417 SOUTHERN PECAN CIRCLE 207 Winter Garden, FL MLS# S5151779
$1,650
1

Beds

1.0

Baths

942

Sq.Ft.

417 SOUTHERN PECAN CIRCLE 207

Winter Garden, FL

View 304 SOUTHERN PECAN CIRCLE 208 Winter Garden, FL MLS# S5151743
$1,900
2

Beds

2.0

Baths

1,264

Sq.Ft.

304 SOUTHERN PECAN CIRCLE 208

Winter Garden, FL

View 706 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6416527
$6,000
5

Beds

5.2

Baths

4,019

Sq.Ft.

706 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 215 CENTER STREET 227 Winter Garden, FL MLS# O6415984
$43,794
2,304

Sq.Ft.

215 CENTER STREET 227

Winter Garden, FL

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

1,014

Estimated median home price

$613,495
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

Price Count
$0 - 100K 1
$100K - 200K 22
$200K - 300K 86
$300K - 400K 78
$400K - 500K 151
$500K - 600K 160
$600K - 700K 114
$700K - 800K 112
$800K - 900K 107
$900K - 1M 64
$1M - Max 119

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 698
Townhouse 146
Condo 133
Commercial 9
Rental 178
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 1
Farms 0

(Data as of 8/23/2026)

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 8/24/2026.