View 211 N HIGHLAND AVENUE Winter Garden, FL MLS# O6427252
  • Recently Listed with Virtual Tour
1 of 15
$2,150
2

Beds

1.0

Baths

980

Sq.Ft.

211 N HIGHLAND AVENUE

Winter Garden, FL

Courtesy of WATSON REALTY CORP
View 12597 ENCORE AT OVATION WAY Winter Garden, FL MLS# O6427276
  • Recently Listed with Virtual Tour
1 of 35
$2,900
3

Beds

2.1

Baths

2,322

Sq.Ft.

12597 ENCORE AT OVATION WAY

Winter Garden, FL

View 16331 SILVER GROVE BOULEVARD Winter Garden, FL MLS# O6427310
  • Recently Listed with Virtual Tour
1 of 49
$5,000
4

Beds

3.1

Baths

3,424

Sq.Ft.

16331 SILVER GROVE BOULEVARD

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 15026 SUMMER HARVEST STREET Winter Garden, FL MLS# S5154214
  • Recently Listed with Virtual Tour
1 of 12
$3,500
4

Beds

4.1

Baths

2,667

Sq.Ft.

15026 SUMMER HARVEST STREET

Winter Garden, FL

Courtesy of MOSAIC PARTNERS GROUP
View 6406 TABEBUIA PARKWAY Winter Garden, FL MLS# O6426916
  • Recently Listed with Virtual Tour
1 of 18
$2,750
3

Beds

2.1

Baths

1,661

Sq.Ft.

6406 TABEBUIA PARKWAY

Winter Garden, FL

View 12560 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6426960
  • Recently Listed with Virtual Tour
1 of 29
$3,500
4

Beds

3.0

Baths

2,148

Sq.Ft.

12560 WESTHAVEN OAK DRIVE

Winter Garden, FL

View 17823 ADRIFT ROAD Winter Garden, FL MLS# O6426062
  • Recently Listed with Virtual Tour
1 of 33
$3,450
4

Beds

2.1

Baths

2,027

Sq.Ft.

17823 ADRIFT ROAD

Winter Garden, FL

View 16435 HAMLIN HILLS ROAD Winter Garden, FL MLS# O6425950
  • Recently Listed with Virtual Tour
1 of 14
$2,980
3

Beds

2.1

Baths

1,736

Sq.Ft.

16435 HAMLIN HILLS ROAD

Winter Garden, FL

Courtesy of VALSTAR REALTY LLC
View 15691 ORANGE HARVEST LOOP Winter Garden, FL MLS# O6426462
  • Recently Listed with Virtual Tour
1 of 20
$3,300
3

Beds

2.1

Baths

2,444

Sq.Ft.

15691 ORANGE HARVEST LOOP

Winter Garden, FL

View Address not provided Winter Garden, FL MLS# O6426643
  • Recently Listed with Virtual Tour
1 of 37
$2,950
3

Beds

2.1

Baths

1,788

Sq.Ft.

Address not provided

Winter Garden, FL

View 15171 BRIDGEWATER CROSSINGS BOULEVARD Winter Garden, FL MLS# O6427348
  • Recently Listed with Virtual Tour
1 of 30
$2,950
3

Beds

2.1

Baths

1,973

Sq.Ft.

15171 BRIDGEWATER CROSSINGS BOULEVARD

Winter Garden, FL

Courtesy of YORK MILLS REALTY LLC
View 11170 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6426380
  • Recently Listed with Virtual Tour
1 of 39
$3,600
4

Beds

3.1

Baths

2,474

Sq.Ft.

11170 HOLLOW BAY DRIVE

Winter Garden, FL

View 430 SOUTHERN PECAN CIRCLE 207 Winter Garden, FL MLS# O6425239
$1,695
1

Beds

1.0

Baths

942

Sq.Ft.

430 SOUTHERN PECAN CIRCLE 207

Winter Garden, FL

View 205 S WOODLAND STREET Winter Garden, FL MLS# G5115261
  • Recently Listed with Virtual Tour
1 of 32
$3,850
3

Beds

2.0

Baths

2,502

Sq.Ft.

205 S WOODLAND STREET

Winter Garden, FL

View Address not provided Winter Garden, FL MLS# S5154024
  • Recently Listed with Virtual Tour
1 of 17
$1,850
2

Beds

1.0

Baths

966

Sq.Ft.

Address not provided

Winter Garden, FL

View 303 SOUTHERN PECAN CIRCLE 107 Winter Garden, FL MLS# O6426302
$1,650
1

Beds

1.0

Baths

838

Sq.Ft.

303 SOUTHERN PECAN CIRCLE 107

Winter Garden, FL

View 15381 AVENUE OF THE ARBORS Winter Garden, FL MLS# O6426190
  • Recently Listed with Virtual Tour
1 of 32
$2,800
4

Beds

2.1

Baths

1,999

Sq.Ft.

15381 AVENUE OF THE ARBORS

Winter Garden, FL

View 15349 SHONAN GOLD DRIVE Winter Garden, FL MLS# O6425756
  • Recently Listed with Virtual Tour
1 of 6
$3,200
4

Beds

3.0

Baths

2,204

Sq.Ft.

15349 SHONAN GOLD DRIVE

Winter Garden, FL

View 10738 RHETT BUTLER ALLEY Winter Garden, FL MLS# S5153938
  • Recently Listed with Virtual Tour
1 of 36
$2,700
3

Beds

2.1

Baths

1,636

Sq.Ft.

10738 RHETT BUTLER ALLEY

Winter Garden, FL

View 5043 LAKE HAMLIN TRAIL Winter Garden, FL MLS# O6426255
  • Recently Listed with Virtual Tour
1 of 11
$3,200
4

Beds

3.0

Baths

2,038

Sq.Ft.

5043 LAKE HAMLIN TRAIL

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

989

Estimated median home price

$610,000
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 - 200K20
$200K - 300K93
$300K - 400K62
$400K - 500K141
$500K - 600K170
$600K - 700K104
$700K - 800K115
$800K - 900K100
$900K - 1M63
$1M - Max120

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family688
Townhouse131
Condo136
Commercial11
Rental215
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/22/2026)

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 7/22/2026.