View 14038 JOMATT LOOP Winter Garden, FL MLS# O6394977
$1,059,000
4

Beds

3.1

Baths

4,105

Sq.Ft.

14038 JOMATT LOOP

Winter Garden, FL

Courtesy of INFINITY REALTY GROUP LLC
View 17368 WILD DAISY DRIVE Winter Garden, FL MLS# G5110440
$909,778
6

Beds

4.0

Baths

4,236

Sq.Ft.

17368 WILD DAISY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15255 MARITIME PINE DRIVE Winter Garden, FL MLS# G5110443
$923,250
4

Beds

3.1

Baths

3,498

Sq.Ft.

15255 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View Address not provided Winter Garden, FL MLS# G5110454
$955,893
6

Beds

4.0

Baths

4,236

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 419 WINTER GROVE BOULEVARD Winter Garden, FL MLS# O6395693
  • New Construction with Virtual Tour
1 of 35
$874,990
5

Beds

3.1

Baths

2,650

Sq.Ft.

419 WINTER GROVE BOULEVARD

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 14254 SUNRIDGE BOULEVARD Winter Garden, FL MLS# TB8489171
$1,150,000
5

Beds

3.1

Baths

4,004

Sq.Ft.

14254 SUNRIDGE BOULEVARD

Winter Garden, FL

Courtesy of PAULINO GLOBAL REAL ESTATE
View 1646 HOLCOMB CREEK STREET Winter Garden, FL MLS# O6394506
$929,000
4

Beds

4.1

Baths

3,841

Sq.Ft.

1646 HOLCOMB CREEK STREET

Winter Garden, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 17549 SEIDNER ROAD Winter Garden, FL MLS# O6392430
$950,000
3

Beds

2.1

Baths

2,130

Sq.Ft.

17549 SEIDNER ROAD

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 14187 JOMATT LOOP Winter Garden, FL MLS# O6393373
$949,900
6

Beds

3.1

Baths

4,181

Sq.Ft.

14187 JOMATT LOOP

Winter Garden, FL

Courtesy of ELEVATE REAL ESTATE BROKERS
View 16006 GILDEN WAY Winter Garden, FL MLS# O6392997
$1,084,999
5

Beds

4.0

Baths

3,617

Sq.Ft.

16006 GILDEN WAY

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 6261 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5110034
$890,955
6

Beds

4.0

Baths

4,236

Sq.Ft.

6261 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 11205 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6392839
  • New Construction with Virtual Tour
1 of 31
$939,990
4

Beds

3.1

Baths

3,327

Sq.Ft.

11205 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 12965 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6392975
  • New Construction with Virtual Tour
1 of 31
$882,932
5

Beds

4.1

Baths

3,101

Sq.Ft.

12965 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of TAYLOR MORRISON REALTY OF FLORIDA INC
View 14354 WABASSO LOOP Winter Garden, FL MLS# O6392378
$939,000
4

Beds

4.0

Baths

2,881

Sq.Ft.

14354 WABASSO LOOP

Winter Garden, FL

Courtesy of HOUWZER INC
View 17090 HAGGERTY HOLLOW ESTATE Winter Garden, FL MLS# G5109783
$1,130,987
6

Beds

4.1

Baths

3,412

Sq.Ft.

17090 HAGGERTY HOLLOW ESTATE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8216 TOPSAIL PLACE Winter Garden, FL MLS# O6391155
$974,900
4

Beds

3.1

Baths

3,055

Sq.Ft.

8216 TOPSAIL PLACE

Winter Garden, FL

Courtesy of REALTY ONE GROUP MVP
View 14766 ELLINGSWORTH LANE Winter Garden, FL MLS# O6390518
$1,099,000
5

Beds

4.1

Baths

4,661

Sq.Ft.

14766 ELLINGSWORTH LANE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 617 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6389100
$1,150,000
4

Beds

4.1

Baths

3,624

Sq.Ft.

617 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 6243 FLOWERIND CHERRY BEND Winter Garden, FL MLS# G5109529
$946,950
6

Beds

4.0

Baths

4,236

Sq.Ft.

6243 FLOWERIND CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15377 MARITIME PINE DRIVE Winter Garden, FL MLS# G5109533
$999,315
6

Beds

4.0

Baths

4,222

Sq.Ft.

15377 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC

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

$609,990
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 - 200K25
$200K - 300K92
$300K - 400K80
$400K - 500K140
$500K - 600K172
$600K - 700K129
$700K - 800K113
$800K - 900K89
$900K - 1M71
$1M - Max125

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family718
Townhouse135
Condo143
Commercial10
Rental213
Lots and Land27
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 6/1/2026)

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 6/1/2026.