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241 N Dillard Street

WINTER GARDEN, FL 34787
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Bed 4

Bed

Bath 3

Bath

SqFt3,507

Sqft

Acres0.64

Acre(Lot)

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 tha t 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.

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Detail Ic Property Details

Property Type : Residential

Price : $1,499,999

AD Id : 67904806

MLS Id : MFRO6353975

Beds : 4

Lot Size : 0.64 Acre

Living Area Size : 3,507

Year Built : 1953

County : Orange

Subdivision: J L Dillard Sub 3

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Feature Features

  • Bedroom Information

    Total Bedroom: 4

    Bathroom Information

    Total Baths: 3 Full Baths: 3

    Interior Features

    Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Stone Counters Roof: Shingle Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer Laundry Features: Inside, Laundry Room

    Roofing Information

    Shingle
  • Flooring Information

    Flooring: Carpet, Wood Construction Materials: Block, Concrete
  • Heating & Cooling

    Heating: Central, Electric Cooling: Central Air WaterSource: Public

  • Building Information

    Year Built: 1953
  • Exterior Features

    Courtyard, French Doors, Garden, Lighting, Sidewalk, Storage Construction Materials: Block, Concrete Foundation Details: Slab

  • Lot Information

    Lot Description: Corner Lot, City Limits, In County, Landscaped, Level, Oversized Lot, Sidewalk, Paved Lot Square Feet: 27988 Lot Acres: 0.64 Lot Size (SqMt): 2600

    Property Information

    Property Type: Residential Sub Type: Single Family Residence Style: Traditional

  • Listing Price Information

    Original List Price:$1800000

  • Tax Information

    Tax Block: - Tax Book Number: R-36 Tax Lot: 1 Tax Legal Description: J L DILLARD SUB NO 3 R/36 LOTS 1 & 2 Annual Tax: $2959 Tax Year: 2024 Parcel Number: 27-22-14-2088-00-010

  • School Information

    Elementary School: Dillard Street Elem Junior High School: Lakeview Middle Senior High School: West Orange High
  • Utility Information

    BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Sewer Connected, Water Connected Sewer: Public Sewer Water Source: Public
  • Location Information

    Subdivision: J L DILLARD SUB 3 City: WINTER GARDEN Direction: Head west on State Rte 50 W. Turn right onto S Dillard St. In 1.2 mi. property will be on the right.
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
Undisclosed Address, Winter Garden, FL, 34787 $870,000 4 4 3,078 3,078 SqFt
15115 Pigeon Plum Lane, Winter Garden, FL, 34787 $505,000 3 2 1,728 1,728 SqFt
120 Blue Stone Circle, Winter Garden, FL, 34787 $737,900 4 3 2,529 2,529 SqFt
330 English Lake Drive, Winter Garden, FL, 34787 $1,090,000 4 3 3,047 3,047 SqFt
1701 E Bay Street, Winter Garden, FL, 34787 $289,000 2 2 825 825 SqFt
12513 Scarlett Sage Court, Winter Garden, FL, 34787 $839,000 5 3 3,570 3,570 SqFt
680 Dunbar Avenue, Winter Garden, FL, 34787 $465,000 4 2 1,713 1,713 SqFt
1672 Malcolm Pointe Drive, Winter Garden, FL, 34787 $479,900 3 2 2,035 2,035 SqFt
689 Bethune Avenue, Winter Garden, FL, 34787 $434,000 4 2 1,434 1,434 SqFt
1142 Dunbrooke Street, Winter Garden, FL, 34787 $515,000 4 3 2,068 2,068 SqFt
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ByOwner last updated this listing 07/26/2026 @ 18:20

MLS: MFRMLS #O6353975 LISTED BY: Erica Diaz, HOMEVEST REALTY 407-897-5400 SOURCE: MFRMLS (My Florida Regional MLS DBA Stellar MLS) (Listings courtesy of MFRMLS (My Florida Regional MLS DBA Stellar MLS) as distributed by MLS GRID)

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