$1,800,000
241 N Dillard Street Winter Garden, FL 34787
For Sale MLS# O6353975
3 beds 3 baths 3,507 sq ft Single Family
Details for 241 N Dillard Street
MLS# O6353975
Description for 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 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.
Listing Information
Property Type: Residential, Single Family Residence
Status: Active
Bedrooms: 3
Bathrooms: 3
Lot Size: 0.64 Acres
Square Feet: 3,507 sq ft
Year Built: 1953
Stories: 1 Story
Construction: Block,Concrete
Subdivision: J L Dillard Sub 3
Foundation: Slab
County: Orange
School Information
Elementary: Dillard Street Elem
Middle: Lakeview Middle
High: West Orange High
Room Information
Main Floor
Bedroom 3:
Bedroom 2:
Primary Bedroom:
Kitchen:
Living Room:
Dining Room:
Family Room:
Bathrooms
Full Baths: 2
1/2 Baths: 1
Additonal Room Information
Laundry: Laundry Room, Inside
Interior Features
Appliances: Washer, Gas Water Heater, Built-In Oven, Refrigerator, Range Hood, Microwave, Cooktop, Dishwasher, Disposal, Dryer
Flooring: Carpet,Wood
Fireplaces: Other, Wood Burning
Additional Interior Features: Eat-In Kitchen, Ceiling Fan(s), Kitchen/Family Room Combo, Open Floorplan, Stone Counters, Living/Dining Room, High Ceilings, Crown Molding
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Cable Connected,Electricity Connected,Natural Gas Connected,High Speed Internet Available,Phone Available,Sewer Connected,Water Connected
Cooling: Ceiling Fan(s), Central Air
Heating: Electric, Central
Exterior / Lot Features
Parking Description: Covered, driveway, Garage Faces Side
Roof: Shingle
Additional Exterior/Lot Features: French Patio Doors, Sprinkler/Irrigation, Garden, Storage, Courtyard, Lighting, Patio, Porch, Rear Porch, Flat, Level, Corner Lot, Landscaped, City Lot, Oversized Lot, Outside City Limits
Community Features
Community Features: Sidewalks
Driving Directions
Head west on State Rte 50 W. Turn right onto S Dillard St. In 1.2 mi. property will be on the right.
Financial Considerations
Terms: Cash,Conventional,VA Loan
Tax/Property ID: 27-22-14-2088-00-010
Tax Amount: 2959
Tax Year: 2024
A broker reciprocity listing courtesy: HOMEVEST REALTY
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Payment Calculator
Interest rate and annual percentage rate (APR) are based on current market conditions, are for informational purposes only, are subject to change without notice and may be subject to pricing add-ons related to property type, loan amount, loan-to-value, credit score and other variables. Estimated closing costs used in the APR calculation are assumed to be paid by the borrower at closing. If the closing costs are financed, the loan, APR and payment amounts will be higher. If the down payment is less than 20%, mortgage insurance may be required and could increase the monthly payment and APR. Contact us for details. Additional loan programs may be available. Accuracy is not guaranteed, and all products may not be available in all borrower's geographical areas and are based on their individual situation. This is not a credit decision or a commitment to lend.
Sales History & Tax Summary for 241 N Dillard Street
Sales History
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Tax Summary
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Data powered by ATTOM Data Solutions. Copyright© 2025. Information deemed reliable but not guaranteed.
Schools
Schools nearby 241 N Dillard Street
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Data powered by ATTOM Data Solutions. Copyright© 2025. Information deemed reliable but not guaranteed.
The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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