Welcome to a rare opportunity to acquire one of Southern Maryland's truly exceptional waterfront estates. Steeped in history that dates back to the mid-19th century, this remarkable property, historically known as Timerity Farm (also referred to as Westbury Farm), encompasses approximately 189 acres of farmland, mature woodland, and protected waterfront along School House Branch, with direct access to St. George Creek and the Potomac River. With approximately 5,000 linear feet of protected shoreline (GIS-derived estimate), the property offers an extraordinary combination of privacy, agricultural productivity, abundant wildlife, recreational boating, and timeless Chesapeake Bay character. The historic manor house is a charming one-and-one-half-story frame residence believed to date from the mid-1800s. The home retains much of its historic character, retaining rare historic pent chimneys, an increasingly uncommon architactural feature in Maryland. Designed on a traditional side-passage/double-parlor floor plan, the home features separate living and dining rooms, each with its own fireplace, hardwood flooring, and period painted moldings. The residence offers 3 bedrooms, including one on the main level and 2 upstairs along with two full bathrooms. The country kitchen adjoins a generous gathering area ideal for entertaining family and friends. A covered side porch overlooks the waterfront and provides the perfect setting for crab feasts, relaxing evenings, or simply enjoying the peaceful views across School House Branch. The private pier serving the residence extends into protected waters with an estimated water depth of approximately five feet at Mean Low Water (MLW) based upon available GIS mapping and aerial analysis, providing convenient access for a variety of recreational boats. The productive farmland is currently leased to a local farmer, providing agricultural income while preserving the property's rural heritage. In addition to the main residence, the property includes three cottages and four barns/outbuildings, offering numerous possibilities for agricultural operations, guest accommodations, storage, workshops, or future restoration. According to St. Mary's County Planning and Zoning, all Transferable Development Rights (TDRs) remain available and have not been exercised, presenting an important opportunity for future planning. Whether envisioned as a private family estate, working farm, sporting property, equestrian retreat, or waterfront sanctuary, this extraordinary offering combines historic significance, productive farmland, protected boating waters, and exceptional natural beauty into one remarkable Chesapeake Bay property. The protected waters of School House Branch provide easy access to St. George Creek and the Potomac River while offering a sheltered location for boating, fishing, kayaking, and paddleboarding. Disclaimer: Acreage is approximate. Shoreline footage (approximately 5,000 linear feet) and water depth at the pier (approximately 5 feet MLW) are estimates derived from publicly available GIS mapping, aerial imagery, and related public information and are not based on a boundary or hydrographic survey. Buyers should independently verify all measurements, water depths, development rights, zoning, and other material information to their satisfaction.