View 16006 GILDEN WAY Winter Garden, FL MLS# O6392997
$1,024,999
5

Beds

4.0

Baths

3,617

Sq.Ft.

16006 GILDEN WAY

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 16104 SANDHILL ROAD Winter Garden, FL MLS# O6411589
$1,020,000
3

Beds

2.0

Baths

1,364

Sq.Ft.

16104 SANDHILL ROAD

Winter Garden, FL

View 16149 LEYLAND CYPRESS LANE Winter Garden, FL MLS# G5104655
$1,005,995
5

Beds

3.1

Baths

3,764

Sq.Ft.

16149 LEYLAND CYPRESS LANE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 851 9TH STREET Winter Garden, FL MLS# O6306969
$1,000,000
Studio

Beds

0.0

Baths

851 9TH STREET

Winter Garden, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 9207 BUSACO PARK WAY Winter Garden, FL MLS# O6366636
$1,000,000
5

Beds

4.0

Baths

3,291

Sq.Ft.

9207 BUSACO PARK WAY

Winter Garden, FL

View 10007 LITTLE ALCOVE LOOP Winter Garden, FL MLS# S5132434
$999,990
4

Beds

3.1

Baths

2,921

Sq.Ft.

10007 LITTLE ALCOVE LOOP

Winter Garden, FL

Courtesy of MBT REALTY LLC
View 6394 WILD PERSIMMON WAY Winter Garden, FL MLS# G5107546
$999,990
6

Beds

4.0

Baths

4,236

Sq.Ft.

6394 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 403 WINTER GROVE BOULEVARD Winter Garden, FL MLS# O6405130
  • New Construction with Virtual Tour
1 of 39
$999,961
5

Beds

3.1

Baths

2,681

Sq.Ft.

403 WINTER GROVE BOULEVARD

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 6352 WILD PERSIMMON WAY Winter Garden, FL MLS# G5107315
$999,914
6

Beds

4.0

Baths

4,236

Sq.Ft.

6352 WILD PERSIMMON WAY

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
View 9493 EMERALD BERRY DRIVE Winter Garden, FL MLS# O6325653
$999,000
4

Beds

3.1

Baths

3,211

Sq.Ft.

9493 EMERALD BERRY DRIVE

Winter Garden, FL

View 17552 LAKE STAR ROAD Winter Garden, FL MLS# O6344668
$999,000
4

Beds

3.1

Baths

2,605

Sq.Ft.

17552 LAKE STAR ROAD

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 15219 MARITIME PINE DRIVE Winter Garden, FL MLS# G5107311
$998,124
6

Beds

4.0

Baths

4,236

Sq.Ft.

15219 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 9319 BRADLEIGH DRIVE Winter Garden, FL MLS# O6362694
$995,000
5

Beds

4.1

Baths

3,602

Sq.Ft.

9319 BRADLEIGH DRIVE

Winter Garden, FL

Courtesy of THE PROPERTY STOP LLC
View 15154 TEA TREE DRIVE Winter Garden, FL MLS# G5113803
$994,733
5

Beds

4.1

Baths

3,839

Sq.Ft.

15154 TEA TREE DRIVE

Winter Garden, FL

View 13037 SANDCASTLE DRIVE Winter Garden, FL MLS# O6387932
  • Adult Community with Virtual Tour
1 of 50
$994,295
3

Beds

3.0

Baths

2,902

Sq.Ft.

13037 SANDCASTLE DRIVE

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 15280 MARITIME PINE DRIVE Winter Garden, FL MLS# G5102291
$988,539
5

Beds

3.0

Baths

3,550

Sq.Ft.

15280 MARITIME PINE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
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

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 440 TIERRA VERDE LANE Winter Garden, FL MLS# O6412260
$980,000
4

Beds

3.0

Baths

3,512

Sq.Ft.

440 TIERRA VERDE LANE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2106 BLACK LAKE BOULEVARD Winter Garden, FL MLS# TB8523029
  • Recently Listed with Virtual Tour
1 of 85
$980,000
5

Beds

4.0

Baths

4,111

Sq.Ft.

2106 BLACK LAKE BOULEVARD

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

939

Estimated median home price

$599,999
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 - 200K21
$200K - 300K89
$300K - 400K64
$400K - 500K134
$500K - 600K163
$600K - 700K105
$700K - 800K95
$800K - 900K86
$900K - 1M63
$1M - Max118

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family640
Townhouse130
Condo135
Commercial11
Rental199
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 7/13/2026)

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 7/13/2026.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

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 7/13/2026.