View 14378 BLACK LAKE PRESERVE STREET Winter Garden, FL MLS# O6414181
  • Recently Listed with Virtual Tour
1 of 48
$764,900
4

Beds

4.0

Baths

3,167

Sq.Ft.

14378 BLACK LAKE PRESERVE STREET

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 13877 EASDALE ALLEY Winter Garden, FL MLS# O6413941
$656,545
4

Beds

4.0

Baths

2,593

Sq.Ft.

13877 EASDALE ALLEY

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
View 16466 OLIVE HILL DRIVE Winter Garden, FL MLS# O6409922
  • Recently Listed with Virtual Tour
1 of 43
$660,000
3

Beds

2.1

Baths

2,020

Sq.Ft.

16466 OLIVE HILL DRIVE

Winter Garden, FL

Courtesy of ON ME REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 214 S WOODLAND STREET Winter Garden, FL MLS# O6413395
$800,000
4

Beds

2.0

Baths

2,868

Sq.Ft.

214 S WOODLAND STREET

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 745 MARSH REED DRIVE Winter Garden, FL MLS# TB8514854
$635,000
4

Beds

2.0

Baths

2,596

Sq.Ft.

745 MARSH REED DRIVE

Winter Garden, FL

Courtesy of HOME SOLD REALTY LLC
View 6122 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5113307
$774,549
4

Beds

3.1

Baths

2,515

Sq.Ft.

6122 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 12427 CLEAR SAPPHIRE DRIVE 238 Winter Garden, FL MLS# O6413423
$608,223
4

Beds

3.0

Baths

2,200

Sq.Ft.

12427 CLEAR SAPPHIRE DRIVE 238

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 18422 OLIVER TWIST WAY Winter Garden, FL MLS# O6412770
  • Recently Listed with Virtual Tour
1 of 66
$815,000
5

Beds

4.1

Baths

3,231

Sq.Ft.

18422 OLIVER TWIST WAY

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 15149 CANOE PLACE Winter Garden, FL MLS# O6412776
  • Recently Listed with Virtual Tour
1 of 65
$799,000
4

Beds

3.1

Baths

3,081

Sq.Ft.

15149 CANOE PLACE

Winter Garden, FL

Courtesy of RE/MAX ASSURED
View 1143 HULL ISLAND DRIVE Winter Garden, FL MLS# O6413213
  • Recently Listed with Virtual Tour
1 of 63
$779,900
4

Beds

4.0

Baths

2,788

Sq.Ft.

1143 HULL ISLAND DRIVE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 11165 GREEN CITRON ALLEY Winter Garden, FL MLS# O6413226
  • Recently Listed with Virtual Tour
1 of 61
$649,000
4

Beds

3.0

Baths

2,043

Sq.Ft.

11165 GREEN CITRON ALLEY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 13959 JOMATT LOOP Winter Garden, FL MLS# O6412718
  • Recently Listed with Virtual Tour
1 of 83
$774,900
4

Beds

3.0

Baths

2,814

Sq.Ft.

13959 JOMATT LOOP

Winter Garden, FL

Courtesy of CLOCK TOWER REALTY
View 7841 ICELAND GULL STREET Winter Garden, FL MLS# O6413079
  • Recently Listed with Virtual Tour
1 of 67
$745,000
3

Beds

2.1

Baths

2,765

Sq.Ft.

7841 ICELAND GULL STREET

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 17379 CHANNEL WAY Winter Garden, FL MLS# O6412749
  • Recently Listed with Virtual Tour
1 of 61
$689,000
4

Beds

3.0

Baths

2,782

Sq.Ft.

17379 CHANNEL WAY

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 9717 WATERWAY PASSAGE DRIVE Winter Garden, FL MLS# O6413773
  • Recently Listed with Virtual Tour
1 of 54
$669,500
4

Beds

3.0

Baths

2,117

Sq.Ft.

9717 WATERWAY PASSAGE DRIVE

Winter Garden, FL

Courtesy of LIFESTYLE INTERNATIONAL REALTY
View 13843 LANYARD WAY Winter Garden, FL MLS# O6412130
  • Recently Listed with Virtual Tour
1 of 34
$648,000
4

Beds

3.1

Baths

2,568

Sq.Ft.

13843 LANYARD WAY

Winter Garden, FL

Courtesy of AAA GLOBAL VENTURES PA
View 213 S DILLARD STREET 230 Winter Garden, FL MLS# O6412912
  • Recently Listed with Virtual Tour
1 of 15
$799,000
1,448

Sq.Ft.

213 S DILLARD STREET 230

Winter Garden, FL

Courtesy of 21 NEW HOMES INC
View 5973 CYPRESS HILL ROAD Winter Garden, FL MLS# O6412179
  • Recently Listed with Virtual Tour
1 of 44
$700,000
5

Beds

3.1

Baths

3,532

Sq.Ft.

5973 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of NEARBY REALTY
View 12537 GRAPE CHARDONNAY ALLEY 219 Winter Garden, FL MLS# O6411681
$647,172
3

Beds

3.0

Baths

2,200

Sq.Ft.

12537 GRAPE CHARDONNAY ALLEY 219

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 7542 SUMMERLAKE GROVES STREET Winter Garden, FL MLS# O6411397
  • Recently Listed with Virtual Tour
1 of 21
$610,000
5

Beds

3.0

Baths

2,638

Sq.Ft.

7542 SUMMERLAKE GROVES STREET

Winter Garden, FL

Courtesy of EXP 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.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 6/7/2026.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 6/7/2026.