View 11283 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6405091
  • New Construction with Virtual Tour
1 of 7
$909,466
5

Beds

4.1

Baths

3,225

Sq.Ft.

11283 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 403 WINTER GROVE BOULEVARD Winter Garden, FL MLS# O6405130
  • New Construction with Virtual Tour
1 of 39
$999,961
5

Beds

3.1

Baths

2,681

Sq.Ft.

403 WINTER GROVE BOULEVARD

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
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
The time to sell is now! THE TIME TO SELL IS NOW!
View 13780 FRESH IVY STREET Winter Garden, FL MLS# O6403387
  • Adult Community with Virtual Tour
1 of 51
$865,000
4

Beds

3.0

Baths

2,862

Sq.Ft.

13780 FRESH IVY STREET

Winter Garden, FL

Courtesy of WEMERT GROUP REALTY LLC
View 15078 CANOPY COVER DRIVE Winter Garden, FL MLS# O6404208
  • Adult Community with Virtual Tour
1 of 35
$975,000
3

Beds

2.1

Baths

2,270

Sq.Ft.

15078 CANOPY COVER DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 5150 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6404827
$995,000
5

Beds

4.1

Baths

3,461

Sq.Ft.

5150 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
View 11271 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6403252
  • New Construction with Virtual Tour
1 of 7
$869,996
5

Beds

4.0

Baths

2,866

Sq.Ft.

11271 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 17085 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5111738
$939,880
5

Beds

4.1

Baths

3,409

Sq.Ft.

17085 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 461 GERANIUM PARK WAY Winter Garden, FL MLS# O6403758
$900,000
3

Beds

3.1

Baths

2,432

Sq.Ft.

461 GERANIUM PARK WAY

Winter Garden, FL

Courtesy of THE ROSENBLOOM TEAM
View 15734 SWEET LEMON WAY Winter Garden, FL MLS# O6401408
$950,000
5

Beds

4.1

Baths

3,635

Sq.Ft.

15734 SWEET LEMON WAY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 10174 MERRYMEETING BAY DRIVE Winter Garden, FL MLS# O6402434
$1,050,000
4

Beds

3.1

Baths

2,758

Sq.Ft.

10174 MERRYMEETING BAY DRIVE

Winter Garden, FL

Courtesy of LUXE PROPERTIES LLC
View 16827 SANCTUARY DRIVE Winter Garden, FL MLS# S5148416
$998,000
4

Beds

3.0

Baths

2,281

Sq.Ft.

16827 SANCTUARY DRIVE

Winter Garden, FL

Courtesy of EASY REALTY SERVICES INC
View 17406 HONEYBELL TANGELO COURT Winter Garden, FL MLS# O6402286
  • New Construction with Virtual Tour
1 of 54
$845,000
5

Beds

4.1

Baths

3,427

Sq.Ft.

17406 HONEYBELL TANGELO COURT

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 9942 SUMMERLAKE GROVES STREET Winter Garden, FL MLS# O6402319
$899,000
4

Beds

3.1

Baths

2,935

Sq.Ft.

9942 SUMMERLAKE GROVES STREET

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
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 12513 SCARLETT SAGE COURT Winter Garden, FL MLS# O6393138
$875,000
5

Beds

3.0

Baths

3,570

Sq.Ft.

12513 SCARLETT SAGE COURT

Winter Garden, FL

Courtesy of KARDOSH REALTY
View 15976 CITRUS KNOLL DRIVE Winter Garden, FL MLS# O6399342
$909,000
5

Beds

3.1

Baths

2,953

Sq.Ft.

15976 CITRUS KNOLL DRIVE

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 17876 ADRIFT ROAD Winter Garden, FL MLS# O6400461
$899,000
5

Beds

4.0

Baths

2,866

Sq.Ft.

17876 ADRIFT ROAD

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 12529 DALLINGTON TERRACE Winter Garden, FL MLS# O6400678
$869,990
5

Beds

3.1

Baths

3,519

Sq.Ft.

12529 DALLINGTON TERRACE

Winter Garden, FL

Courtesy of BHHS FLORIDA REALTY
View 12928 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6400451
$1,032,000
5

Beds

4.1

Baths

3,626

Sq.Ft.

12928 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY 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.

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.