J L Dillard Sub 3 Homes with Traditional Architectural style

J L Dillard Sub 3 Homes with Traditional Architectural style

Welcome to J.L. Dillard Subdivision 3, a hidden gem nestled in the heart of Winter Garden, Florida. This charming community is perfectly situated in Orange County, offering residents the ideal blend of suburban tranquility and vibrant city life. Known for its picturesque streets and friendly atmosphere, J.L. Dillard Sub 3 is a place where neighbors become friends and memories are made.

The homes in this delightful subdivision showcase traditional architectural styles that evoke a sense of timeless elegance. With their classic designs, these residences feature inviting front porches, gabled roofs, and beautifully landscaped yards, creating a warm and welcoming ambiance. Each home reflects a commitment to quality craftsmanship, offering spacious layouts that are perfect for family living or entertaining guests.

Living in J.L. Dillard Sub 3 means you’re just a stone's throw away from Winter Garden’s charming downtown area, where you can enjoy boutique shopping, delightful dining options, and community events that bring residents together. Additionally, the nearby West Orange Trail offers an abundance of outdoor recreational opportunities, perfect for those who enjoy biking, running, or leisurely strolls.

With its rich history, friendly community, and beautifully designed homes, J.L. Dillard Subdivision 3 is more than just a place to live; it’s a lifestyle. Whether you’re a first-time homebuyer or looking to downsize, this subdivision offers a unique opportunity to embrace the best of Florida living. Come and discover your dream home in J.L. Dillard Sub 3, where tradition meets modern convenience!

Newest J L Dillard Sub 3 Homes with Traditional Architectural style

$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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