View 17106 BEACHGRASS ALLEY Winter Garden, FL MLS# O6407735
  • Recently Listed with Virtual Tour
1 of 33
$799,990
3

Beds

2.1

Baths

1,983

Sq.Ft.

17106 BEACHGRASS ALLEY

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 1692 HIGHBANKS CIRCLE Winter Garden, FL MLS# O6408620
  • Recently Listed with Virtual Tour
1 of 41
$760,000
4

Beds

3.1

Baths

2,848

Sq.Ft.

1692 HIGHBANKS CIRCLE

Winter Garden, FL

Courtesy of VESTI LLC
View 5443 BOWMAN DRIVE Winter Garden, FL MLS# O6408812
  • Recently Listed with Virtual Tour
1 of 73
$649,000
4

Beds

4.1

Baths

2,656

Sq.Ft.

5443 BOWMAN DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 14525 WHITTRIDGE DRIVE Winter Garden, FL MLS# O6407375
  • Recently Listed with Virtual Tour
1 of 45
$629,000
4

Beds

4.0

Baths

3,487

Sq.Ft.

14525 WHITTRIDGE DRIVE

Winter Garden, FL

Courtesy of DON ASHER & ASSOCIATES, INC.
View 15111 DRIFTWOOD BEND STREET Winter Garden, FL MLS# O6408574
  • Recently Listed with Virtual Tour
1 of 57
$628,000
4

Beds

3.1

Baths

2,573

Sq.Ft.

15111 DRIFTWOOD BEND STREET

Winter Garden, FL

Courtesy of TOPSKY REALTY INC
View 1157 VINSETTA CIRCLE Winter Garden, FL MLS# O6403597
  • Recently Listed with Virtual Tour
1 of 64
$800,000
5

Beds

3.1

Baths

3,598

Sq.Ft.

1157 VINSETTA CIRCLE

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 14784 FIELD DAISY DRIVE Winter Garden, FL MLS# O6408277
  • Recently Listed with Virtual Tour
1 of 48
$690,000
4

Beds

4.1

Baths

2,841

Sq.Ft.

14784 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 7302 TWILIGHT BAY DRIVE Winter Garden, FL MLS# O6407453
  • Recently Listed with Virtual Tour
1 of 50
$749,000
4

Beds

3.0

Baths

2,810

Sq.Ft.

7302 TWILIGHT BAY DRIVE

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 13958 MAGNOLIA RIDGE LOOP Winter Garden, FL MLS# O6406860
  • Recently Listed with Virtual Tour
1 of 58
$600,000
3

Beds

2.0

Baths

2,075

Sq.Ft.

13958 MAGNOLIA RIDGE LOOP

Winter Garden, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 16185 TALIESIN STREET Winter Garden, FL MLS# O6407177
  • Recently Listed
1 of 43
$660,000
4

Beds

3.0

Baths

2,372

Sq.Ft.

16185 TALIESIN STREET

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 14531 CEDAR HILL DRIVE Winter Garden, FL MLS# O6408070
  • Recently Listed with Virtual Tour
1 of 51
$799,000
5

Beds

4.0

Baths

3,510

Sq.Ft.

14531 CEDAR HILL DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 8866 BISMARCK PALM DRIVE Winter Garden, FL MLS# O6408155
  • Recently Listed with Virtual Tour
1 of 64
$795,000
5

Beds

4.0

Baths

3,174

Sq.Ft.

8866 BISMARCK PALM DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 15025 PIGEON PLUM LANE Winter Garden, FL MLS# O6404948
$599,990
4

Beds

2.1

Baths

2,605

Sq.Ft.

15025 PIGEON PLUM LANE

Winter Garden, FL

Courtesy of BLOOM HOME GROUP REALTY LLC
View 7549 SPRING VALLEY STREET Winter Garden, FL MLS# G5112279
$730,791
4

Beds

3.1

Baths

2,515

Sq.Ft.

7549 SPRING VALLEY STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17422 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5112284
$671,415
4

Beds

2.1

Baths

2,235

Sq.Ft.

17422 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 708 ORANGE BELT LOOP Winter Garden, FL MLS# G5112211
  • Recently Listed with Virtual Tour
1 of 46
$745,000
3

Beds

2.0

Baths

1,916

Sq.Ft.

708 ORANGE BELT LOOP

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5978 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5112233
  • Recently Listed with Virtual Tour
1 of 5
$681,240
4

Beds

2.1

Baths

2,802

Sq.Ft.

5978 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 7922 WINTER WREN STREET Winter Garden, FL MLS# O6406681
  • Recently Listed with Virtual Tour
1 of 53
$765,900
4

Beds

3.1

Baths

3,391

Sq.Ft.

7922 WINTER WREN STREET

Winter Garden, FL

Courtesy of YORK MILLS REALTY LLC
View 6153 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5112171
$680,030
4

Beds

2.1

Baths

2,235

Sq.Ft.

6153 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 921 Westcliffe Drive Winter Garden, FL MLS# B26027811
  • Recently Listed with Virtual Tour
1 of 16
$750,000
4

Beds

2.1

Baths

2,354

Sq.Ft.

921 Westcliffe 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

1,037

Estimated median home price

$609,999
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 99
$300K - 400K 78
$400K - 500K 144
$500K - 600K 163
$600K - 700K 128
$700K - 800K 119
$800K - 900K 84
$900K - 1M 81
$1M - Max 118

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 711
Townhouse 142
Condo 141
Commercial 10
Rental 216
Lots and Land 30
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 2
Farms 0

(Data as of 5/18/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 5/19/2026.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 5/19/2026.