241 N DILLARD STREET, WINTER GARDEN, FL 34787

Description of 241 N DILLARD STREET, WINTER GARDEN, FL 34787

Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. 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 three bathrooms 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.

Property Details for 241 N DILLARD STREET, WINTER GARDEN, FL 34787

Bathrooms Full

3

Bathrooms Half

0

Interior Features

Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Stone Counters

Appliances

Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer

Flooring

Carpet, Hardwood

Heating

Central, Electric

Cooling

Central Air

Architectural Style

Traditional

Parking Features

Covered, Driveway, Garage Faces Side

Pool Private

No

Direction Faces

West

Building Information for 241 N DILLARD STREET, WINTER GARDEN, FL 34787

Building Area Total

4671

Building Area Units

Square Feet

Association

No

Pets Allowed

Yes

Property Information for 241 N DILLARD STREET, WINTER GARDEN, FL 34787

Lot Features

Corner Lot, City Lot, In County, Landscaped, Level, Oversized Lot, Sidewalk

Lot Size Square Feet

27,988

Waterfront

No

View

No

Construction Materials

Block, Concrete

Roof

Shingle

Exterior Features

Courtyard, French Doors, Garden, Irrigation System, Lighting, Sidewalk, Storage

Sewer

Public Sewer

Water Source

Public

New Construction

No

Public Records for 241 N DILLARD STREET, WINTER GARDEN, FL 34787

Parcel Number

272214208800010

Tax Annual Amount

$2,959

Tax Year

2024

Tax Legal Description

J L DILLARD SUB NO 3 R/36 LOTS 1 & 2

Zoning

R-2

County Or Parish

Orange

Schools Near 241 N DILLARD STREET, WINTER GARDEN, FL 34787

Elementary School

Dillard Street Elem

Middle School

Lakeview Middle

High School

West Orange High

School assignments are provided by the listing and should be independently verified.

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