View 17060 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5109737
  • New Construction with Virtual Tour
1 of 7
$819,391
6

Beds

4.1

Baths

3,117

Sq.Ft.

17060 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 11253 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6405126
  • New Construction with Virtual Tour
1 of 18
$819,106
4

Beds

3.0

Baths

2,113

Sq.Ft.

11253 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 16331 TALIESIN STREET Winter Garden, FL MLS# O6385168
$815,000
4

Beds

3.1

Baths

3,104

Sq.Ft.

16331 TALIESIN STREET

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
The time to sell is now! THE TIME TO SELL IS NOW!
View 925 BAINBRIDGE LOOP Winter Garden, FL MLS# O6402075
$815,000
4

Beds

4.0

Baths

3,580

Sq.Ft.

925 BAINBRIDGE LOOP

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 18422 OLIVER TWIST WAY Winter Garden, FL MLS# O6412770
  • Recently Listed with Virtual Tour
1 of 66
$815,000
5

Beds

4.1

Baths

3,231

Sq.Ft.

18422 OLIVER TWIST WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 6388 WILD PERSIMMON WAY Winter Garden, FL MLS# G5108486
$814,990
4

Beds

2.1

Baths

2,752

Sq.Ft.

6388 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 3518 TURNINGWIND LANE Winter Garden, FL MLS# S5147067
$810,000
4

Beds

3.0

Baths

2,744

Sq.Ft.

3518 TURNINGWIND LANE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 11223 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6382359
  • New Construction with Virtual Tour
1 of 10
$809,990
5

Beds

4.0

Baths

2,866

Sq.Ft.

11223 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 11193 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6389839
  • New Construction with Virtual Tour
1 of 31
$809,990
4

Beds

3.1

Baths

3,327

Sq.Ft.

11193 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 15162 SPINNAKER COVE LANE Winter Garden, FL MLS# O6393190
$809,900
5

Beds

3.0

Baths

3,902

Sq.Ft.

15162 SPINNAKER COVE LANE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 1087 HUNTSPOINT STREET Winter Garden, FL MLS# O6379734
$800,000
3

Beds

2.0

Baths

1,932

Sq.Ft.

1087 HUNTSPOINT STREET

Winter Garden, FL

Courtesy of OAK AVENUE REAL ESTATE LLC
View 7720 SUMMERLAKE POINTE BOULEVARD Winter Garden, FL MLS# O6399030
$800,000
5

Beds

4.0

Baths

3,893

Sq.Ft.

7720 SUMMERLAKE POINTE BOULEVARD

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 1157 VINSETTA CIRCLE Winter Garden, FL MLS# O6403597
$800,000
5

Beds

3.1

Baths

3,598

Sq.Ft.

1157 VINSETTA CIRCLE

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 214 S WOODLAND STREET Winter Garden, FL MLS# O6413395
$800,000
4

Beds

2.0

Baths

2,868

Sq.Ft.

214 S WOODLAND STREET

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 15755 SWEET LIMETTA DRIVE Winter Garden, FL MLS# O6370049
$799,999
5

Beds

4.1

Baths

3,633

Sq.Ft.

15755 SWEET LIMETTA DRIVE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
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 15852 SHOREBIRD LANE Winter Garden, FL MLS# O6361580
  • Adult Community with Virtual Tour
1 of 71
$799,000
4

Beds

4.1

Baths

2,766

Sq.Ft.

15852 SHOREBIRD LANE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 14931 LEBEAU LOOP Winter Garden, FL MLS# O6364989
$799,000
4

Beds

3.1

Baths

2,832

Sq.Ft.

14931 LEBEAU LOOP

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 5211 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6373067
$799,000
4

Beds

3.1

Baths

2,909

Sq.Ft.

5211 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of MCO REALTY GROUP LLC
View 15563 ORCHID ROSE COURT Winter Garden, FL MLS# O6399638
  • Adult Community with Virtual Tour
1 of 35
$799,000
3

Beds

3.1

Baths

2,808

Sq.Ft.

15563 ORCHID ROSE COURT

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC

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

1,047

Estimated median home price

$615,000
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 - 300K88
$300K - 400K80
$400K - 500K145
$500K - 600K170
$600K - 700K129
$700K - 800K117
$800K - 900K92
$900K - 1M72
$1M - Max129

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family731
Townhouse139
Condo137
Commercial11
Rental197
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 6/7/2026)

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 6/8/2026.

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 6/8/2026.