View 5971 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5107163
$849,970
5

Beds

4.1

Baths

3,076

Sq.Ft.

5971 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5949 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5107173
$845,340
5

Beds

4.1

Baths

3,076

Sq.Ft.

5949 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15672 SHOREBIRD LANE Winter Garden, FL MLS# O6375411
  • Recently Listed with Virtual Tour
1 of 79
$869,900
4

Beds

3.1

Baths

2,799

Sq.Ft.

15672 SHOREBIRD LANE

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 16377 ORANGE SEED LANE Winter Garden, FL MLS# O6376161
  • Recently Listed with Virtual Tour
1 of 42
$830,000
5

Beds

3.1

Baths

3,599

Sq.Ft.

16377 ORANGE SEED LANE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 5966 CYPRESS HILL ROAD Winter Garden, FL MLS# O6376219
  • Recently Listed with Virtual Tour
1 of 30
$719,000
4

Beds

3.1

Baths

2,839

Sq.Ft.

5966 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of DALTON WADE INC
View 12378 CLEAR SAPPHIRE DRIVE 262 Winter Garden, FL MLS# O6374226
$812,519
5

Beds

4.0

Baths

3,045

Sq.Ft.

12378 CLEAR SAPPHIRE DRIVE 262

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 15784 SWEET LIMETTA DRIVE Winter Garden, FL MLS# O6375259
  • Recently Listed with Virtual Tour
1 of 58
$875,000
5

Beds

4.1

Baths

3,635

Sq.Ft.

15784 SWEET LIMETTA DRIVE

Winter Garden, FL

Courtesy of REALTY HUB
View 15087 TEA TREE DRIVE Winter Garden, FL MLS# G5107020
$698,466
4

Beds

2.1

Baths

2,235

Sq.Ft.

15087 TEA TREE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 11120 ROBERT FROST DRIVE Winter Garden, FL MLS# O6374443
$779,900
4

Beds

3.1

Baths

3,436

Sq.Ft.

11120 ROBERT FROST DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 11229 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6375011
  • Recently Listed with Virtual Tour
1 of 48
$807,201
5

Beds

4.1

Baths

3,225

Sq.Ft.

11229 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 15716 SWEET LEMON WAY Winter Garden, FL MLS# O6375190
  • Recently Listed with Virtual Tour
1 of 63
$795,000
4

Beds

3.1

Baths

2,945

Sq.Ft.

15716 SWEET LEMON WAY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 16839 HOBE SOUND COURT Winter Garden, FL MLS# O6374451
  • New Construction with Virtual Tour
1 of 18
$673,170
4

Beds

3.1

Baths

2,489

Sq.Ft.

16839 HOBE SOUND COURT

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 131 OAK LAUREL DRIVE Winter Garden, FL MLS# O6374501
  • Recently Listed with Virtual Tour
1 of 42
$895,000
3

Beds

3.1

Baths

1,906

Sq.Ft.

131 OAK LAUREL DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1826 JEAN MARIE DRIVE Winter Garden, FL MLS# O6375791
  • Recently Listed with Virtual Tour
1 of 64
$810,000
5

Beds

4.0

Baths

3,435

Sq.Ft.

1826 JEAN MARIE DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 2394 BARONSMEDE COURT Winter Garden, FL MLS# O6373715
  • Recently Listed with Virtual Tour
1 of 42
$745,000
3

Beds

2.0

Baths

2,310

Sq.Ft.

2394 BARONSMEDE COURT

Winter Garden, FL

Courtesy of TEAMCONNECT REALTY LLC
View 9611 LOST CREEK DRIVE Winter Garden, FL MLS# O6373845
  • Recently Listed with Virtual Tour
1 of 57
$860,000
4

Beds

3.0

Baths

2,909

Sq.Ft.

9611 LOST CREEK DRIVE

Winter Garden, FL

Courtesy of M2M REALTY
View 6375 WILD PERSIMMON WAY Winter Garden, FL MLS# G5106743
$767,985
4

Beds

3.0

Baths

2,102

Sq.Ft.

6375 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 14123 LARKSPUR LAKE DRIVE Winter Garden, FL MLS# O6372991
  • Recently Listed with Virtual Tour
1 of 36
$775,000
4

Beds

3.1

Baths

3,130

Sq.Ft.

14123 LARKSPUR LAKE DRIVE

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 5211 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6373067
  • Recently Listed with Virtual Tour
1 of 57
$819,000
4

Beds

3.1

Baths

2,909

Sq.Ft.

5211 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of MCO REALTY GROUP LLC
View 607 E OAKLAND AVENUE Winter Garden, FL MLS# O6372870
$875,000
4

Beds

3.1

Baths

3,406

Sq.Ft.

607 E OAKLAND AVENUE

Winter Garden, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY

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

814

Estimated median home price

$589,995
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 - 100K7
$100K - 200K11
$200K - 300K74
$300K - 400K80
$400K - 500K145
$500K - 600K114
$600K - 700K101
$700K - 800K75
$800K - 900K68
$900K - 1M49
$1M - Max90

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family530
Townhouse127
Condo116
Commercial7
Rental239
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/26/2026)

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 1/26/2026.