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$1,600,000
Original: $1,800,000
Active
241 N DILLARD STREET
WINTER GARDEN, FL 34787 — J L DILLARD SUB 3
3 Beds
3 Baths
3,507 sqft
0.64 acres
Built 1953
About This Property
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 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.
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
Basics
- Property Type
- Residential
- Property Subtype
- Single Family Residence
- MLS Number
- O6353975
- Days on Market
- 162
- Year Built
- 1953
- Levels
- One
- Architectural Style
- Traditional
- Additional Rooms
- Bonus Room,Inside Utility
- Direction Faces
- West
- Occupant Type
- Owner
Size & Structure
- Living Area
- 3,507 sqft
- Total Area
- 4,671 sqft
- Lot Size
- 0.64 acres
- Lot Sq Ft
- 27,988 sqft
- Bedrooms
- 3
- Full Baths
- 3
Interior
- Flooring
- Carpet, Wood
- Appliances
- Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer
- 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
- Laundry
- Inside, Laundry Room
- Fireplace
- Yes — Other, Wood Burning
- A/C
- Central Air
- Heating
- Central, Electric
Exterior & Lot
- Exterior Features
- Courtyard, French Doors, Garden, Lighting, Sidewalk, Storage
- Construction
- Block, Concrete
- Roof
- Shingle
- Foundation
- Slab
- Patio/Porch
- Patio, Porch, Rear Porch
- Lot Features
- Corner Lot, City Limits, In County, Landscaped, Level, Oversized Lot, Sidewalk, Paved
Water & Pool
Community & HOA
- HOA
- No
- Pets Allowed
- Yes
- Homestead
- Yes
Utilities & Systems
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Sewer Connected, Water Connected
- Cooling
- Central Air
- Heating
- Central, Electric
- Flood Zone
- X
- Parking
- Covered, Driveway, Garage Faces Side
Financial
- List Price
- $1,600,000
- Original Price
- $1,800,000
- Annual Taxes
- $2,959
- Tax Year
- 2024
- Listing Terms
- Cash, Conventional, VA Loan
- Special Conditions
- None
Schools
- Elementary
- Dillard Street Elem
- Middle School
- Lakeview Middle
- High School
- West Orange High