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

The time to sell is now! THE TIME TO SELL IS NOW!
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 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 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 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

View 16545 BARBOURS CREEK WAY Winter Garden, FL MLS# O6427167
  • Recently Listed with Virtual Tour
1 of 19
$2,500
3

Beds

2.1

Baths

1,567

Sq.Ft.

16545 BARBOURS CREEK WAY

Winter Garden, FL

View 12743 BRODLOVE LANE Winter Garden, FL MLS# O6427186
  • Recently Listed with Virtual Tour
1 of 36
$3,300
4

Beds

3.1

Baths

2,558

Sq.Ft.

12743 BRODLOVE LANE

Winter Garden, FL

Courtesy of ROBERT SLACK LLC
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

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

1,082

Estimated median home price

$618,500
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 - 200K23
$200K - 300K95
$300K - 400K67
$400K - 500K156
$500K - 600K184
$600K - 700K115
$700K - 800K133
$800K - 900K104
$900K - 1M68
$1M - Max136

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family766
Townhouse142
Condo139
Commercial11
Rental226
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 7/24/2026)

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 7/24/2026.