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$1,499,999
4 Beds ⋅ 3 Baths ⋅ J L Dillard Sub 3 SubDv. ⋅ 34787 Zip Code
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.

241 N Dillard Street, Winter Garden
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Orange County › Winter Garden › J L Dillard Subdivision

J L Dillard Subdivision, Winter Garden

Where J L Dillard Subdivision is

J L Dillard Subdivision, centered at 28.568996, -81.583285. Drag to explore.
Street level, inside the neighborhood. Drag to look around.

Drive times below are measured on the road network from the center of J L Dillard Subdivision, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving toTimeMiles
Downtown Orlando24 min17.1
Walt Disney World29 min24.1
Orlando International Airport29 min25.5
Universal Orlando24 min16.1

Public schools nearby

  • Dillard Street Elementary School 0 min, 0.1 mi
  • SLV High School 3 min, 0.5 mi
  • Maxey Elementary School 4 min, 1.2 mi
  • St Lillie V High School 4 min, 1.3 mi

Private schools nearby

  • Foundation Academy, Plant Street Campus 1 min, 0.2 mi

Parks and recreation

  • Dr. Bradford Memorial Park 3 min, 0.6 mi
  • Maple Street Park 2 min, 0.6 mi
  • Newton Park 3 min, 0.6 mi
  • Veterans Memorial Park 4 min, 1.3 mi

Groceries and errands

  • D J Discount Market 2 min, 0.3 mi
  • Tn Food & Grocery 2 min, 0.3 mi
  • Tea Bar 2 min, 0.4 mi
  • The Ancient Olive Gourmet of Winter Garden 2 min, 0.4 mi

Nearest is not the same as zoned. The schools above are the closest ones to J L Dillard Subdivision by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in J L Dillard Subdivision actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 0 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated September 2026.

Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.

What homes sold for in J L Dillard Subdivision

n/aMedian sale price
n/aMedian per square foot
n/aMedian days to contract
0Homes sold in 12 months

Questions about a specific home in J L Dillard Subdivision, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for J L Dillard Subdivision in Winter Garden, Orange County, covering closed sales from 25 September 2025 through 20 September 2026, refreshed monthly and current as of September 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.