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

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

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

The time to sell is now! THE TIME TO SELL IS NOW!
View 1646 HOLCOMB CREEK STREET Winter Garden, FL MLS# O6394506
  • Virtual Tour
1 of 49
OPEN HOUSE: Saturday 8/29 12:00 PM - 2:00 PM
$851,500
5

Beds

4.1

Baths

3,841

Sq.Ft.

1646 HOLCOMB CREEK STREET

Winter Garden, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 13412 FOX GLOVE STREET Winter Garden, FL MLS# G5110319
$829,900
5

Beds

2.1

Baths

3,954

Sq.Ft.

13412 FOX GLOVE STREET

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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

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

View 6063 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5109530
$832,470
5

Beds

4.1

Baths

3,076

Sq.Ft.

6063 FLOWERING CHERRY BEND

Winter Garden, FL

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

View 6039 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5109534
$859,460
5

Beds

4.1

Baths

3,076

Sq.Ft.

6039 FLOWERING CHERRY BEND

Winter Garden, FL

View 16545 BROADWATER AVENUE Winter Garden, FL MLS# O6389243
$824,900
4

Beds

3.0

Baths

3,036

Sq.Ft.

16545 BROADWATER AVENUE

Winter Garden, FL

View 9218 HOLLISTON CREEK PLACE Winter Garden, FL MLS# O6386394
$880,000
4

Beds

3.1

Baths

3,087

Sq.Ft.

9218 HOLLISTON CREEK PLACE

Winter Garden, FL

View 276 SUMMER PINE STREET Winter Garden, FL MLS# O6384565
  • New Construction with Virtual Tour
1 of 25
$873,000
5

Beds

3.0

Baths

3,147

Sq.Ft.

276 SUMMER PINE STREET

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 15184 TEA TREE DRIVE Winter Garden, FL MLS# G5108559
$925,990
4

Beds

3.1

Baths

3,498

Sq.Ft.

15184 TEA TREE DRIVE

Winter Garden, FL

View 6340 WILD PERSIMMON WAY Winter Garden, FL MLS# G5108490
$879,760
6

Beds

4.0

Baths

4,236

Sq.Ft.

6340 WILD PERSIMMON WAY

Winter Garden, FL

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

View 6267 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5108489
$980,295
6

Beds

4.0

Baths

4,236

Sq.Ft.

6267 FLOWERING CHERRY BEND

Winter Garden, FL

View 17606 LAKE STAR ROAD Winter Garden, FL MLS# O6382909
$870,000
4

Beds

3.1

Baths

2,605

Sq.Ft.

17606 LAKE STAR ROAD

Winter Garden, FL

View 6376 WILD PERSIMMON WAY Winter Garden, FL MLS# G5108436
$951,803
6

Beds

4.0

Baths

4,236

Sq.Ft.

6376 WILD PERSIMMON WAY

Winter Garden, FL

View 17222 DANCY ORANGE COURT Winter Garden, FL MLS# O6383910
$949,000
5

Beds

4.1

Baths

3,787

Sq.Ft.

17222 DANCY ORANGE COURT

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

1,018

Estimated median home price

$613,300
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 - 200K22
$200K - 300K86
$300K - 400K76
$400K - 500K154
$500K - 600K162
$600K - 700K116
$700K - 800K112
$800K - 900K107
$900K - 1M65
$1M - Max117

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family703
Townhouse148
Condo131
Commercial9
Rental183
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 8/26/2026)

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 8/27/2026.