8706 Crain Highway, Upper Marlboro, MD 20772Asking Price of: $769,900

Woodstock | Upper Marlboro, Maryland Introducing “Woodstock,” an extraordinary and historically significant estate dating to the 1800s, recognized among the oldest continuously inhabited residences in Prince George’s County. Rich in provenance, architectural character, and timeless elegance, this remarkable property presents a once-in-a-generation opportunity to own and preserve a distinguished piece of Maryland history. Privately set across approximately 8.19 scenic acres in Upper Marlboro, the offering also includes two additional parcels conveying with the sale: Outlot A (0.42 acres) and the Trumps Hill parcel (2.77 acres) - each separately deeded with its own Tax ID and legal description. The estate carries an agricultural designation, with historic designation documentation available within the disclosures. The stately main residence encompasses more than 3,000 square feet of living space and is filled with irreplaceable period details that speak to its storied past. Original architectural elements, multiple fireplaces, antique fixtures, rich millwork, and authentic historic craftsmanship create an atmosphere of warmth, sophistication, and enduring charm rarely found today. Offering five bedrooms and 3.5 bathrooms across multiple levels, the home provides exceptional scale and flexibility for refined country living, thoughtful restoration, or legacy ownership. Complementing the main residence is a separate cottage offering endless possibilities as a guest house, private studio, caretaker’s residence, executive office, or creative retreat. The grounds are equally captivating, featuring mature trees, expansive lawns, charming outbuildings, and picturesque surroundings that reflect generations of stewardship and care. Recent enhancements include a newly paved driveway completed with an investment of approximately $30,000, a renovated kitchen blending modern convenience with historic character, and the added security and comfort of a generator system. Perfectly balancing privacy and accessibility, Woodstock offers the tranquility of an estate setting while remaining conveniently positioned near major commuter routes, equestrian amenities, Washington, D.C., and the broader Maryland countryside. This is an estate sale and the property is being sold strictly as-is. A rare offering of historical significance, land, scale, and legacy - Woodstock presents an unparalleled opportunity to restore, preserve, and reimagine one of Prince George’s County’s most treasured and distinctive estates.