241 N Dillard St, Winter Garden, FL 34787 | For Sale

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For Sale $1,800,000 ($513.26 per Sq Ft)

$1,800,000 ($513.26 per Sq Ft)
  • (0)
  • 3 Bedrooms
  • 3 Bathrooms
  • 3,507 Sq Ft
  • 27,988 Sq Ft

Description

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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Amenities

Garage
Pool
Garden
Security System
Internet
Telephone
Heating
Fireplace
Balcony & Patio
TV / Cable
Laundry
Hardwood Floors
Spa
Air Conditioning
Solar Power
Floor Plan
Great Views
Natural Light
Quiet
Water View
Elevator
Guest Unit(s)
Furnished
220 Volt

Income

Rental Units


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Expenses

Property Details

List Price $1,800,000
Property Type Single Family Homes
Usable Sqft 3,507
Number of Stories 0 stories
Parking Spots 3 spots
Year Built 1953
Last Sold Unknown
Sold Price Unknown
APN # 272214208800010
MLS # O6353975
Property ID 317168256
Lot Sqft 27,988
Zoning R-2
Days on Market 111
Original List Price $1,800,000
Applicances Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer%
Date Updated November 20, 2025
Date Created October 20, 2025
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Listing Provided By

Erica Diaz an agent of . Lic #3301261


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