995 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 16894 WINGSPREAD LOOP Winter Garden, FL MLS# O6362090
$1,270,000
5

Beds

3.1

Baths

3,906

Sq.Ft.

16894 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of THE BRAHMIN GROUP
View 14048 LARKSPUR LAKE DRIVE Winter Garden, FL MLS# O6432377
$1,255,000
4

Beds

3.0

Baths

2,464

Sq.Ft.

14048 LARKSPUR LAKE DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 706 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6394059
$1,225,000
5

Beds

5.2

Baths

4,019

Sq.Ft.

706 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 243 ZACHARY WADE STREET Winter Garden, FL MLS# O6391909
$1,220,000
5

Beds

3.1

Baths

3,097

Sq.Ft.

243 ZACHARY WADE STREET

Winter Garden, FL

Courtesy of REGENCY REAL ESTATE LLC
View 205 SURPRISE DRIVE Winter Garden, FL MLS# O6365188
  • Virtual Tour
1 of 32
$1,200,000
4

Beds

2.1

Baths

2,171

Sq.Ft.

205 SURPRISE DRIVE

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 1812 LAKE ROBERTS LANDING DRIVE Winter Garden, FL MLS# O6415935
$1,200,000
6

Beds

4.0

Baths

4,247

Sq.Ft.

1812 LAKE ROBERTS LANDING DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 14807 WINTER STAY DRIVE Winter Garden, FL MLS# O6448906
  • Recently Listed with Virtual Tour
1 of 55
$1,200,000
5

Beds

4.0

Baths

3,856

Sq.Ft.

14807 WINTER STAY DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 16795 TURTLE HATCH DRIVE Winter Garden, FL MLS# O6438512
$1,199,990
5

Beds

5.0

Baths

3,615

Sq.Ft.

16795 TURTLE HATCH DRIVE

Winter Garden, FL

Courtesy of LIVE MVRK LLC
View 15594 SHOREBIRD LANE Winter Garden, FL MLS# O6443596
  • Recently Listed with Virtual Tour
1 of 47
$1,199,000
4

Beds

3.1

Baths

3,022

Sq.Ft.

15594 SHOREBIRD LANE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 10048 BEACH PORT DRIVE Winter Garden, FL MLS# O6446829
  • Recently Listed with Virtual Tour
1 of 67
$1,199,000
5

Beds

3.1

Baths

3,910

Sq.Ft.

10048 BEACH PORT DRIVE

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 9189 BUSACO PARK WAY Winter Garden, FL MLS# O6410698
$1,198,000
4

Beds

4.0

Baths

3,424

Sq.Ft.

9189 BUSACO PARK WAY

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 844 OAKLAND PARK BOULEVARD Winter Garden, FL MLS# O6419976
$1,195,000
5

Beds

4.0

Baths

3,525

Sq.Ft.

844 OAKLAND PARK BOULEVARD

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 17588 LAKE STAR ROAD Winter Garden, FL MLS# O6387269
$1,185,000
5

Beds

4.0

Baths

4,026

Sq.Ft.

17588 LAKE STAR ROAD

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 8836 LAKESHORE POINTE DRIVE Winter Garden, FL MLS# O6421088
  • Recently Listed with Virtual Tour
1 of 45
$1,175,000
4

Beds

3.1

Baths

2,914

Sq.Ft.

8836 LAKESHORE POINTE DRIVE

Winter Garden, FL

Courtesy of THE AGENCY FL
View 8222 TOPSAIL PLACE Winter Garden, FL MLS# O6430527
  • Virtual Tour
1 of 52
$1,170,000
5

Beds

4.1

Baths

4,199

Sq.Ft.

8222 TOPSAIL PLACE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 10198 MERRYMEETING BAY DRIVE Winter Garden, FL MLS# O6421817
$1,160,000
5

Beds

3.1

Baths

3,911

Sq.Ft.

10198 MERRYMEETING BAY DRIVE

Winter Garden, FL

Courtesy of LOKATION
View 5074 BREEZY ACRES STREET Winter Garden, FL MLS# O6442063
$1,159,900
7

Beds

4.1

Baths

4,720

Sq.Ft.

5074 BREEZY ACRES STREET

Winter Garden, FL

Courtesy of CREEGAN GROUP
View 16753 TURTLE HATCH DRIVE Winter Garden, FL MLS# O6438081
$1,159,000
4

Beds

3.1

Baths

2,954

Sq.Ft.

16753 TURTLE HATCH DRIVE

Winter Garden, FL

Courtesy of REALTY WORLD PREFERRED
View 650 MEDORA WAY Winter Garden, FL MLS# O6431624
  • New Construction with Virtual Tour
1 of 12
$1,157,190
4

Beds

3.0

Baths

2,902

Sq.Ft.

650 MEDORA WAY

Winter Garden, FL

Courtesy of DAVILA HOMES
View 16071 BARKLY RIDGE COURT Winter Garden, FL MLS# O6390569
$1,150,000
4

Beds

3.0

Baths

2,986

Sq.Ft.

16071 BARKLY RIDGE COURT

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE

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

993

Estimated median home price

$595,000
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

Price Count
$0 - 100K 1
$100K - 200K 33
$200K - 300K 72
$300K - 400K 79
$400K - 500K 155
$500K - 600K 169
$600K - 700K 108
$700K - 800K 114
$800K - 900K 102
$900K - 1M 57
$1M - Max 103

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 686
Townhouse 150
Condo 120
Commercial 6
Rental 228
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 10/13/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

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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 real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Weichert Realtors are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. 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.

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Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Copyright © 2026 Midwest Real Estate Data LLC.

Data is updated as of 10/13/2026.

The data relating to real estate for sale/lease on this web site come in part from the New Smyrna Beach Board of REALTORS® Multiple Listing Service (MLS) in which this real estate firm (Broker) participates. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with the Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with the MLS IDX logo. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein or for their use or interpretation by the user. Federal law prohibits discrimination on the basis of race, color, sex, religion, handicap, familial status or national origin in the sale, rental or financing of housing.

This data updated periodically, at an interval not to exceed 7 days.

IDX information 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.

Some properties which appear for sale on this website may subsequently have sold and may no longer be available.

© Copyright 2026 New Smyrna Beach Board of REALTORS, Inc. All rights Reserved.

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 10/13/2026.

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 10/13/2026.