654 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 16271 HONEY HARVEST STREET Winter Garden, FL MLS# O6386199
$696,000
5

Beds

4.1

Baths

2,812

Sq.Ft.

16271 HONEY HARVEST STREET

Winter Garden, FL

View 5966 CYPRESS HILL ROAD Winter Garden, FL MLS# O6376219
$695,000
4

Beds

3.1

Baths

2,839

Sq.Ft.

5966 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of DALTON WADE INC
View 13062 SUNSET GARDEN LANE Winter Garden, FL MLS# O6400441
  • New Construction with Virtual Tour
1 of 7
$693,270
5

Beds

4.0

Baths

2,686

Sq.Ft.

13062 SUNSET GARDEN LANE

Winter Garden, FL

Courtesy of ORLANDO TBI REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 7580 SPRING VALLEY STREET Winter Garden, FL MLS# G5111519
$693,230
4

Beds

3.1

Baths

2,515

Sq.Ft.

7580 SPRING VALLEY STREET

Winter Garden, FL

View 14784 FIELD DAISY DRIVE Winter Garden, FL MLS# O6408277
  • New Construction with Virtual Tour
1 of 45
$690,000
4

Beds

4.1

Baths

2,841

Sq.Ft.

14784 FIELD DAISY DRIVE

Winter Garden, FL

View 6110 MERIWETHER CRESCENT Winter Garden, FL MLS# O6411208
$690,000
5

Beds

2.1

Baths

2,830

Sq.Ft.

6110 MERIWETHER CRESCENT

Winter Garden, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 15174 FIELD DAISY DRIVE Winter Garden, FL MLS# O6415990
$689,000
4

Beds

3.1

Baths

2,686

Sq.Ft.

15174 FIELD DAISY DRIVE

Winter Garden, FL

Courtesy of REALTY ONE GROUP INSPIRATION
View 1743 FULLERS OAK LOOP Winter Garden, FL MLS# O6419299
$689,000
4

Beds

2.1

Baths

2,536

Sq.Ft.

1743 FULLERS OAK LOOP

Winter Garden, FL

View Address not provided Winter Garden, FL MLS# G5110452
$688,789
5

Beds

4.1

Baths

3,117

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17054 HAGGERTY HOLLOW DRIVE Winter Garden, FL MLS# G5109477
$688,324
4

Beds

2.1

Baths

2,235

Sq.Ft.

17054 HAGGERTY HOLLOW DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17440 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5109764
$688,324
4

Beds

2.1

Baths

2,235

Sq.Ft.

17440 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17404 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5108715
$685,645
4

Beds

2.1

Baths

2,235

Sq.Ft.

17404 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 12438 CLEAR SAPPHIRE DRIVE 223 Winter Garden, FL MLS# O6393877
$684,990
4

Beds

4.0

Baths

3,460

Sq.Ft.

12438 CLEAR SAPPHIRE DRIVE 223

Winter Garden, FL

Courtesy of K HOVNANIAN FLORIDA REALTY
View 5978 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5112233
  • New Construction with Virtual Tour
1 of 5
$681,240
4

Beds

2.1

Baths

2,802

Sq.Ft.

5978 FLOWERING CHERRY BEND

Winter Garden, FL

View 6153 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5112171
$680,030
4

Beds

2.1

Baths

2,235

Sq.Ft.

6153 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 16271 SILVER GROVE BLVD Winter Garden, FL MLS# O6299810
  • New Construction with Virtual Tour
1 of 46
$680,000
4

Beds

2.1

Baths

2,093

Sq.Ft.

16271 SILVER GROVE BLVD

Winter Garden, FL

Courtesy of CELEBRITY GLOBAL REALTY LLC
View 4918 WILDWOOD POINTE ROAD Winter Garden, FL MLS# S5150274
$680,000
5

Beds

3.1

Baths

2,868

Sq.Ft.

4918 WILDWOOD POINTE ROAD

Winter Garden, FL

View 14494 BREAKWATER WAY Winter Garden, FL MLS# S5139023
$679,000
5

Beds

3.0

Baths

3,638

Sq.Ft.

14494 BREAKWATER WAY

Winter Garden, FL

Courtesy of NUMBER 1 BROKER, LLC
View 8721 BAYVIEW CROSSING DRIVE Winter Garden, FL MLS# G5111855
$679,000
4

Beds

3.1

Baths

2,842

Sq.Ft.

8721 BAYVIEW CROSSING DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY
View 2022 BOSS HEWETT STREET Winter Garden, FL MLS# O6417697
  • Recently Listed with Virtual Tour
1 of 36
$679,000
4

Beds

3.0

Baths

2,281

Sq.Ft.

2022 BOSS HEWETT STREET

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

1,083

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 - 300K94
$300K - 400K77
$400K - 500K144
$500K - 600K188
$600K - 700K124
$700K - 800K117
$800K - 900K103
$900K - 1M75
$1M - Max136

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family766
Townhouse136
Condo144
Commercial11
Rental206
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 6/30/2026)

Information deemed reliable but not guaranteed.

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 6/30/2026.

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 6/30/2026.