This exceptional 47± acre waterfront farm is located just outside Historic St. Michaels, offering a rare combination of productive farmland, extensive improvements and water views across Leadenham Creek. Encompassing approximately 42± tillable acres, the property is ideally suited for agricultural use, hunting and a serves as a stunning waterfront retreat. A tree-lined blacktop drive leads to the beautifully renovated brick main residence. Updated in 2017, the 3,500± square foot home is filled with natural light and thoughtfully designed to capture the property's attractive waterfront setting. Luxury vinyl plank flooring flows throughout the open-concept floor plan, where expansive windows frame sweeping views of the creek and surrounding farmland. The spacious kitchen, features white cabinetry, quartz countertops, stainless steel appliances, a large center island with bar seating, a beverage bar and a dining space suitable for a large farmhouse table. The adjoining living room provides comfortable everyday living, while the waterside family room is the heart of the home, serving as a showpiece with cathedral ceilings, exposed wood beams, skylights, a gas fireplace and floor-to-ceiling windows creating a seamless connection to the waterfront landscape and farm fields beyond. The waterfront primary suite offers a luxurious en-suite bath featuring dual sink vanity, a glass-enclosed tile shower and a spacious walk-in closet. Three additional guest bedrooms provide ample accommodations, complemented by a full bath with a dual sink vanity. A waterside office with pocket doors offers flexibility as a sitting room or space for additional guests. Completing the home is a large mudroom/laundry room, abundant storage space, an additional full bath and an oversized two-car garage. Outdoor living is equally impressive. A rear patio leads to the waterside in-ground pool surrounded by expansive hardscaping, creating the perfect setting for entertaining or relaxing while enjoying the tranquil views. The private dock, equipped with electric and a boat lift, provides direct access to the creeks, rivers and surrounding tributaries of the Chesapeake Bay. A separate 2,700± square foot guest house offers even more versatility, featuring 3-4 bedrooms and 2-baths. Ideal for extended family, guests, farm staff or potential rental income, it provides comfortable accommodations while maintaining privacy from the main residence. Supporting the farm operation are numerous outbuildings, including a substantial 40'x60' enclosed equipment barn with electric, plumbing and a 12’x30’ open lean-to, a 50’x120’ open equipment building and a 24'x40' barn with attached 12’x24’ lean-to. Once operated as a beef farm, this versatile property presents endless opportunities for farming, livestock, equestrian use or the creation of a multi-generational family compound. Currently leased and farmed by a local farmer, the tillable acreage allows owners to enjoy the charm and scenic beauty of a working farm, along with the agricultural tax benefits without the time commitment and responsibilities of the farm operations. For hunters and outdoor enthusiasts, the farm offers excellent habitat for deer, turkey and geese, while the waterfront location provides easy access to boating and fishing. Properties rarely come available that offer this combination of acreage, waterfront, extensive improvements and a prime location just minutes from the shops, restaurants and the maritime charm of downtown St. Michaels. This is Eastern Shore living at its finest.