241 N DILLARD STREET Winter Garden, FL $ 1,800,000
241 N DILLARD STREET
$ 1,800,000
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241 N DILLARD STREET

Winter Garden, FL, 34787
$ 1,800,000
Bedrooms3 Baths2.1 Sq 3,507

Monthly Estimate*

$ 11,230

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Single Family Home for sale in Winter Garden, FL

for $1,800,000 with 3 bedrooms and 2 full baths, 1 half bath. This 3,507 square foot home was built in 1953 on a lot size of 0.64.

Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and two-and-a-half baths, perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.

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Single Family Active

Price

$ 1,800,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 2,959

Style

Traditional

Lot Size

0.64

Year Built

1953

Town/City

Winter Garden

County/Region

Orange

MLS | Web ID

O6353975

Features
General
Sewer Public Sewer
Heating Central Electric
Cooling Central Air
Utilities BB/HS Internet Available Cable Connected Electricity Connected Natural Gas Connected Phone Available Sewer Connected Water Connected
Roof Shingle
Appliances Built-In Oven Cooktop Dishwasher Disposal Dryer Gas Water Heater Microwave Range Hood Refrigerator Washer
Zoning R-2
Patio/Porch Features Patio Porch Rear Porch
Architectural Style Traditional
Construction Materials Block Concrete
Pets Allowed Yes
Year Built 1953
Levels One
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
County Orange
New Construction false
Property Type Residential
Subdivision Name J L DILLARD SUB 3
Facing Direction West
Garage Y/N false
Total Rooms 7
Full Baths 2
Status Active
Directions Head west on State Rte 50 W. Turn right onto S Dillard St. In 1.2 mi. property will be on the right.
High School West Orange High
City WINTER GARDEN
Senior Community Y/N false
MLS Area 34787 - Winter Garden/Oakland
Lot Size Units Square Feet
Lot Size Square Feet 27988
Carport Spaces 3
Carport Y/N true
Listing Terms Cash Conventional VA Loan
Elementary School Dillard Street Elem
Land Lease Y/N false
Tax Annual Amount 2959
Middle/Junior High School Lakeview Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.zillow.com/view-imx/37f39412-fc82-4833-8cd6-c4ee120d5e6a?wl=true&setAttribution=mls&initialViewType=pano
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 1
Legal Description J L DILLARD SUB NO 3 R/36 LOTS 1 & 2
Minimum Lease 8-12 Months
Water Access Y/N false
Additional Rooms Bonus Room Inside Utility
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Ceiling Fan(s) Crown Molding Eating Space In Kitchen High Ceilings Kitchen/Family Room Combo Living Room/Dining Room Combo Open Floorplan Stone Counters
Flooring Carpet Hardwood
Fireplace Features Other Room Wood Burning
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 1
Laundry Features Inside Laundry Room
Total Bedrooms 3
Total Baths 3
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Exterior
Exterior Amenities Courtyard French Doors Garden Irrigation System Lighting Sidewalk Storage
Vegetation Mature Landscaping Oak Trees Trees/Landscaped
Parking Features Covered Driveway Garage Faces Side
Lot Features Corner Lot City Lot In County Landscaped Level Oversized Lot Sidewalk
Water Source Public
Lot Size Area 27988
Foundation Details Slab
Building Area Total 4671
Lot Size Acres 0.64
Road Surface Type Paved
Private Pool false
Waterfront Y/N false
Covered Spaces 3
Road Frontage Type Street Paved
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* Excluded Features
List By
Homevest Realty

Broker

erica@ericadiazteam.com

Email

Affordability Calculator

$11,476
Per Month
98%
2%
0%
Monthly Principal & Interest
$11,230
Monthly Property Taxes
$247
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
West Orange High High School High School
Pricing History
DatePricePrice ChangeDescription
12/19/2025$1,800,000 Listed Price

Map


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241 N DILLARD STREET, Winter Garden, FL, 34787 is a Single Family Home for sale at $1,800,000 with 3,507 sqft and a lot size of 0.64. 241 N DILLARD STREET has 3 bedrooms, 2.1 baths, and was built in 1953. The property's zip code is 34787 which is in Winter Garden, FL