308 N Main Street
Greensboro, MD 21639

Welcome to your very own historic waterfront retreat! The picturesque 'Leonard House', is a meticulously restored 18th-century gem nestled on a sprawling 1.3-acre lot along the Choptank River in the town of Greensboro. This enchanting residence boasts over 1700 square feet of living space, including three bedrooms and two baths. Steeped in history and charm, this remarkable property offers a rare opportunity to own a piece of Maryland's past while enjoying modern comforts and conveniences. As you step inside, you're greeted by original wide plank floors, the warmth of five inviting fireplaces, a formal dining area, a den, and sitting room, all whispering tales of bygone eras. The addition includes the primary suite on the second floor, laundry room, 2 full baths and a thoughtfully designed modern country kitchen with granite countertop and stainless steel appliances. As an added bonus there is a large butlers pantry complete with butlers bar allowing for plenty of room for storage. New Anderson windows and doors, refurbished hard wood floors, newer roof, and updated bathrooms, further enhance the home's appeal. The deck and gravel patio off the back invite you to savor a private oasis of mature landscaping native to Maryland. A spacious attached two-car garage provides ample parking and storage. For guests or potential rental income, a charming 500+ square foot, 19th-century guest cottage awaits. Complete with an updated kitchenette, river view deck, loft bedroom, full bath, wood burning stove, and original beams. This cozy retreat has been rented in the past, offering flexibility and versatility. Outdoors, indulge in nature and waterfront living along the Choptank River. Perfect for kayaking, canoeing, catching cat fish and making riverfront memories. The boat house with electric, 4-bay pole barn equipped with concrete floor, water, and electric, chicken coop and established gardens fed by underwater springs, are ideal for hobbyists or outdoor enthusiasts. This property provides endless opportunities to explore and connect with the natural beauty of the Choptank River. An additional parcel of land is included, currently serving as an established garden for native plants and vegetables. With potential for subdivision, buyers are encouraged to explore the possibilities with the appropriate authorities. There are endless possibilities awaiting you at the Leonard House - whether you're seeking a historic retreat, a waterfront haven, or a nature lover's paradise, this unique property offers it all and more. Don't miss your chance to make this extraordinary residence your own.