View 6162 GLORY BOWER DRIVE Winter Garden, FL MLS# O6428754
$3,000
3

Beds

2.1

Baths

1,881

Sq.Ft.

6162 GLORY BOWER DRIVE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 17739 SHARP PUMMELO ALLEY Winter Garden, FL MLS# O6428033
$3,000
3

Beds

2.0

Baths

1,788

Sq.Ft.

17739 SHARP PUMMELO ALLEY

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
View 15742 SWEET LIMETTA DRIVE Winter Garden, FL MLS# O6428553
$3,600
4

Beds

3.0

Baths

2,369

Sq.Ft.

15742 SWEET LIMETTA DRIVE

Winter Garden, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 2052 SOLAR DRIVE Winter Garden, FL MLS# O6424337
  • Recently Listed with Virtual Tour
1 of 33
$4,275
5

Beds

3.0

Baths

3,711

Sq.Ft.

2052 SOLAR DRIVE

Winter Garden, FL

View 12893 HARVEST RAIN AVENUE Winter Garden, FL MLS# S5154412
  • Recently Listed with Virtual Tour
1 of 53
$4,500
5

Beds

4.1

Baths

3,165

Sq.Ft.

12893 HARVEST RAIN AVENUE

Winter Garden, FL

View 16238 WIND VIEW LANE Winter Garden, FL MLS# O6428206
$4,150
4

Beds

3.1

Baths

2,772

Sq.Ft.

16238 WIND VIEW LANE

Winter Garden, FL

View 1470 BROKEN OAK DRIVE 27C Winter Garden, FL MLS# O6428198
  • Recently Listed with Virtual Tour
1 of 84
$2,450
3

Beds

2.1

Baths

1,699

Sq.Ft.

1470 BROKEN OAK DRIVE 27C

Winter Garden, FL

View 2413 PRAIRIE VIEW Winter Garden, FL MLS# O6427839
  • Recently Listed with Virtual Tour
1 of 55
$4,300
4

Beds

3.0

Baths

3,000

Sq.Ft.

2413 PRAIRIE VIEW

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 7591 TANGERINE KNOLL LOOP Winter Garden, FL MLS# O6427588
  • Recently Listed with Virtual Tour
1 of 13
$3,450
4

Beds

3.1

Baths

2,697

Sq.Ft.

7591 TANGERINE KNOLL LOOP

Winter Garden, FL

Courtesy of TRUVISION REAL ESTATE LLC
View 14186 TITLE WAY Winter Garden, FL MLS# O6427672
  • Recently Listed with Virtual Tour
1 of 13
$3,000
4

Beds

3.1

Baths

2,508

Sq.Ft.

14186 TITLE WAY

Winter Garden, FL

View 14252 TITLE WAY Winter Garden, FL MLS# O6427693
  • Recently Listed with Virtual Tour
1 of 26
$3,000
4

Beds

3.1

Baths

2,475

Sq.Ft.

14252 TITLE WAY

Winter Garden, FL

View 8 E CYPRESS STREET Winter Garden, FL MLS# O6427158
  • Recently Listed with Virtual Tour
1 of 14
$2,200
2

Beds

2.0

Baths

1,220

Sq.Ft.

8 E CYPRESS STREET

Winter Garden, FL

View 15175 CHAPTER WAY Winter Garden, FL MLS# O6428136
  • Recently Listed with Virtual Tour
1 of 71
$3,550
4

Beds

3.1

Baths

2,307

Sq.Ft.

15175 CHAPTER WAY

Winter Garden, FL

Courtesy of ALLIVE REALTY
View 211 N HIGHLAND AVENUE Winter Garden, FL MLS# O6427252
$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 15026 SUMMER HARVEST STREET Winter Garden, FL MLS# S5154214
  • Recently Listed with Virtual Tour
1 of 12
$4,500
4

Beds

4.1

Baths

2,667

Sq.Ft.

15026 SUMMER HARVEST STREET

Winter Garden, FL

Courtesy of MOSAIC PARTNERS GROUP
View 123 PENNSYLVANIA AVENUE Winter Garden, FL MLS# O6427304
  • Recently Listed with Virtual Tour
1 of 14
$1,650
2

Beds

1.0

Baths

1,066

Sq.Ft.

123 PENNSYLVANIA AVENUE

Winter Garden, FL

View 15167 NEWTONIA STREET Winter Garden, FL MLS# O6427490
  • Recently Listed with Virtual Tour
1 of 28
$3,100
4

Beds

3.1

Baths

2,306

Sq.Ft.

15167 NEWTONIA STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
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

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

1,063

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 - 200K24
$200K - 300K93
$300K - 400K68
$400K - 500K154
$500K - 600K184
$600K - 700K111
$700K - 800K128
$800K - 900K103
$900K - 1M66
$1M - Max131

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family751
Townhouse140
Condo139
Commercial10
Rental218
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/28/2026)

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 7/28/2026.