View 96 WINDTREE LANE 203 Winter Garden, FL MLS# O6366344
$1,750
2

Beds

2.0

Baths

918

Sq.Ft.

96 WINDTREE LANE 203

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 5637 WATER ROSE ROAD Winter Garden, FL MLS# O6366225
$2,850
3

Beds

2.1

Baths

1,617

Sq.Ft.

5637 WATER ROSE ROAD

Winter Garden, FL

Courtesy of THE FLORIDA LOUNGE REALTY LLC
View 6314 HAMLIN RESERVE BOULEVARD Winter Garden, FL MLS# S5139917
$2,600
3

Beds

2.1

Baths

1,568

Sq.Ft.

6314 HAMLIN RESERVE BOULEVARD

Winter Garden, FL

Courtesy of ALTIS REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 5144 CITRUS LEAF BOULEVARD Winter Garden, FL MLS# O6365901
$3,500
4

Beds

3.0

Baths

2,072

Sq.Ft.

5144 CITRUS LEAF BOULEVARD

Winter Garden, FL

Courtesy of TREE REALTY
View 7054 BROOMSHEDGE TRAIL TRAIL Winter Garden, FL MLS# S5139900
$2,370
2

Beds

2.1

Baths

1,200

Sq.Ft.

7054 BROOMSHEDGE TRAIL TRAIL

Winter Garden, FL

Courtesy of LA ROSA REALTY KISSIMMEE
View 12524 WESTHAVEN OAK DRIVE Winter Garden, FL MLS# O6364959
  • New Construction with Virtual Tour
1 of 33
$3,500
5

Beds

3.1

Baths

2,200

Sq.Ft.

12524 WESTHAVEN OAK DRIVE

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 16771 TURTLE HATCH DRIVE D Winter Garden, FL MLS# O6365612
$4,500
4

Beds

3.1

Baths

2,954

Sq.Ft.

16771 TURTLE HATCH DRIVE D

Winter Garden, FL

Courtesy of LA ROSA REALTY LLC
View 11168 HANLON TERRACE ALLEY Winter Garden, FL MLS# O6365800
$2,850
4

Beds

3.0

Baths

2,037

Sq.Ft.

11168 HANLON TERRACE ALLEY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 13172 CALMING BREEZE WAY Winter Garden, FL MLS# O6365137
  • New Construction with Virtual Tour
1 of 58
$2,800
3

Beds

2.1

Baths

1,720

Sq.Ft.

13172 CALMING BREEZE WAY

Winter Garden, FL

Courtesy of PREMIUM PROPERTIES R.E. SERVICE
View 12632 CHARMED DRIVE Winter Garden, FL MLS# O6364273
$2,800
3

Beds

2.1

Baths

1,814

Sq.Ft.

12632 CHARMED DRIVE

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 12767 HARVEST RAIN AVENUE Winter Garden, FL MLS# O6364632
  • New Construction with Virtual Tour
1 of 20
$3,380
4

Beds

2.1

Baths

2,441

Sq.Ft.

12767 HARVEST RAIN AVENUE

Winter Garden, FL

Courtesy of MS LAND & BUILDING LLC
View 15331 HAYWORTH DRIVE Winter Garden, FL MLS# G5105332
$3,000
4

Beds

3.0

Baths

2,971

Sq.Ft.

15331 HAYWORTH DRIVE

Winter Garden, FL

Courtesy of THE FLORIDA PROPERTY SHOP SALE
View 11163 GREAT ROCK STREET Winter Garden, FL MLS# O6364381
$5,350
5

Beds

3.0

Baths

3,393

Sq.Ft.

11163 GREAT ROCK STREET

Winter Garden, FL

Courtesy of MANAGER PROP
View 162 WINDTREE LANE 204 Winter Garden, FL MLS# G5105117
$1,595
2

Beds

2.0

Baths

918

Sq.Ft.

162 WINDTREE LANE 204

Winter Garden, FL

Courtesy of RE/MAX TITANIUM GROUP
View 12664 CHARMED DRIVE Winter Garden, FL MLS# O6358668
  • New Construction
1 of 22
$2,650
3

Beds

2.1

Baths

1,568

Sq.Ft.

12664 CHARMED DRIVE

Winter Garden, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 1500 BROKEN OAK DRIVE 25B Winter Garden, FL MLS# S5139230
$2,200
3

Beds

2.1

Baths

1,544

Sq.Ft.

1500 BROKEN OAK DRIVE 25B

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 13817 LUNA HARVEST AVENUE Winter Garden, FL MLS# O6364255
$3,200
4

Beds

3.0

Baths

2,163

Sq.Ft.

13817 LUNA HARVEST AVENUE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 981 VINELAND ROAD Winter Garden, FL MLS# O6364366
  • New Construction with Virtual Tour
1 of 6
$0
8,700

Sq.Ft.

981 VINELAND ROAD

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 6725 MARMALADE ALLEY Winter Garden, FL MLS# S5139516
$2,700
4

Beds

3.0

Baths

1,718

Sq.Ft.

6725 MARMALADE ALLEY

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 399 WINTER NELLIS CIRCLE Winter Garden, FL MLS# O6364179
$2,400
3

Beds

2.1

Baths

1,592

Sq.Ft.

399 WINTER NELLIS CIRCLE

Winter Garden, FL

Courtesy of JAMIESON PROPERTIES, 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

814

Estimated median home price

$589,945
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 - 200K12
$200K - 300K72
$300K - 400K83
$400K - 500K142
$500K - 600K118
$600K - 700K97
$700K - 800K76
$800K - 900K67
$900K - 1M49
$1M - Max91

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family526
Townhouse129
Condo117
Commercial7
Rental239
Lots and Land33
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/22/2026)

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 1/25/2026.