207 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 16662 WINGSPREAD LOOP Winter Garden, FL MLS# O6371940
$599,900
3

Beds

2.1

Baths

2,372

Sq.Ft.

16662 WINGSPREAD LOOP

Winter Garden, FL

Courtesy of PARK PLACE LENDING & INVESTMENTS INC
View 15633 WATER SPRING BOULEVARD Winter Garden, FL MLS# S5141422
$450,000
4

Beds

2.1

Baths

1,992

Sq.Ft.

15633 WATER SPRING BOULEVARD

Winter Garden, FL

Courtesy of FLORIDA HOMES REALTY & MORTGAGE
View 15345 HAMLIN PARK DRIVE Winter Garden, FL MLS# TB8461483
  • New Construction with Virtual Tour
1 of 49
$529,990
3

Beds

3.1

Baths

2,072

Sq.Ft.

15345 HAMLIN PARK DRIVE

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View Address not provided Winter Garden, FL MLS# G5106258
  • New Construction
1 of 28
OPEN HOUSE: Saturday 2/7 1:00 PM - 4:00 PM
$599,990
3

Beds

3.0

Baths

2,083

Sq.Ft.

Address not provided

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 16304 BRIGHT LEAF ROAD Winter Garden, FL MLS# O6371581
  • New Construction with Virtual Tour
1 of 28
$513,190
4

Beds

2.1

Baths

1,770

Sq.Ft.

16304 BRIGHT LEAF ROAD

Winter Garden, FL

Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
View 15508 BLACKBEAD STREET Winter Garden, FL MLS# O6371455
$445,000
3

Beds

2.1

Baths

1,754

Sq.Ft.

15508 BLACKBEAD STREET

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 707 MONTE VISTA WAY Winter Garden, FL MLS# O6371318
$485,000
4

Beds

3.1

Baths

3,030

Sq.Ft.

707 MONTE VISTA WAY

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 10624 WORDS DRIVE Winter Garden, FL MLS# O6370851
  • Virtual Tour
1 of 8
$460,000
4

Beds

2.1

Baths

1,992

Sq.Ft.

10624 WORDS DRIVE

Winter Garden, FL

Courtesy of SALVAMERICA, LLC
View 15274 GROVESIDE ROAD Winter Garden, FL MLS# O6369999
  • New Construction
1 of 4
$457,390
3

Beds

2.1

Baths

1,846

Sq.Ft.

15274 GROVESIDE ROAD

Winter Garden, FL

Courtesy of DRB GROUP REALTY, LLC
View 15232 GROVESIDE ROAD Winter Garden, FL MLS# O6369879
  • New Construction with Virtual Tour
1 of 8
$471,340
3

Beds

2.1

Baths

1,846

Sq.Ft.

15232 GROVESIDE ROAD

Winter Garden, FL

Courtesy of DRB GROUP REALTY, LLC
View 1504 E SPRING RIDGE CIRCLE Winter Garden, FL MLS# O6369221
$549,999
3

Beds

2.0

Baths

2,012

Sq.Ft.

1504 E SPRING RIDGE CIRCLE

Winter Garden, FL

Courtesy of HOMEVEST REALTY
View 4122 SHEPPERDS HOLLOW ALLEY Winter Garden, FL MLS# O6370363
$574,990
3

Beds

3.1

Baths

2,459

Sq.Ft.

4122 SHEPPERDS HOLLOW ALLEY

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 17490 NORTHLAKE GROVE DRIVE Winter Garden, FL MLS# TB8460402
  • New Construction with Virtual Tour
1 of 38
$499,990
3

Beds

2.1

Baths

1,675

Sq.Ft.

17490 NORTHLAKE GROVE DRIVE

Winter Garden, FL

Courtesy of ASHTON WOODS FLORIDA REALTY LLC
View 1373 WILLIAMS ROAD Winter Garden, FL MLS# O6370110
  • Virtual Tour
1 of 44
$539,990
4

Beds

3.1

Baths

2,492

Sq.Ft.

1373 WILLIAMS ROAD

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 16330 BRISK BREEZE ALLEY Winter Garden, FL MLS# G5106012
$575,000
3

Beds

2.1

Baths

2,170

Sq.Ft.

16330 BRISK BREEZE ALLEY

Winter Garden, FL

Courtesy of NARROW ROAD REALTY
View 15401 PORTER ROAD Winter Garden, FL MLS# S5140743
  • Virtual Tour
1 of 49
$558,000
5

Beds

3.0

Baths

2,322

Sq.Ft.

15401 PORTER ROAD

Winter Garden, FL

Courtesy of MULTI CHOICE REALTY LLC
View 64 ZACHARY WADE STREET Winter Garden, FL MLS# O6370095
$480,000
4

Beds

2.0

Baths

1,888

Sq.Ft.

64 ZACHARY WADE STREET

Winter Garden, FL

Courtesy of REALTY AND COMPANY INT., LLC
View 6837 Pasturelands Pl Winter Garden, FL MLS# A11936347
$465,000
3

Beds

2.0

Baths

1,650

Sq.Ft.

6837 Pasturelands Pl

Winter Garden, FL

Courtesy of SPACE REAL ESTATE AGENCY
View 16632 POINT ROCK DRIVE Winter Garden, FL MLS# OM715702
$550,000
4

Beds

3.1

Baths

2,292

Sq.Ft.

16632 POINT ROCK DRIVE

Winter Garden, FL

Courtesy of RE/MAX PREMIER REALTY
View 3136 IRISH PEACH DRIVE Winter Garden, FL MLS# O6367113
$599,900
3

Beds

2.0

Baths

2,136

Sq.Ft.

3136 IRISH PEACH DRIVE

Winter Garden, FL

Courtesy of CASTLE REALTY PROFESSIONAL GROUP 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

817

Estimated median home price

$590,000
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 7
$100K - 200K 11
$200K - 300K 78
$300K - 400K 82
$400K - 500K 137
$500K - 600K 116
$600K - 700K 101
$700K - 800K 74
$800K - 900K 67
$900K - 1M 55
$1M - Max 89

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 539
Townhouse 120
Condo 118
Commercial 7
Rental 237
Lots and Land 31
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 1
Farms 0

(Data as of 2/2/2026)

Information deemed reliable but not guaranteed.

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/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 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

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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 2/2/2026.

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 2/2/2026.