25 HIGH STREET · BROOKEVILLE, MARYLAND
Caleb Bentley was a Quaker silversmith and the first postmaster of Brookeville.
Henrietta Bentley, his wife, was a lifelong friend of Dolley Madison and the unofficial center of social life in the village. Their house on Market Street – the post office, the silver shop, and the family home all in one – was where President Madison spent the night of August 26, 1814.
The original Bentley house still stands, two blocks from this estate. The Bentley Manor is its neighbor in spirit and, by design, the first estate a visitor encounters when arriving on High Street.
The Bentley House is inspired by the legacy of Caleb and Henrietta Bentley and is not the original Bentley residence. The historic Bentley home, where President James Madison spent the night of August 26, 1814, remains privately owned within the Town of Brookeville and is located just a short walk from Madison Manor. This residence honors that history while respectfully acknowledging the original home’s continued private ownership.
Inspired by the warmth and generosity associated with the Bentley family, The Bentley House is a residence designed for gathering, connection, and everyday living. Thoughtfully crafted by GTM Architects, it balances welcoming spaces for entertaining with the comfort and ease of a home meant to be lived in for generations.
Positioned at the entrance to Madison Manor, The Bentley House occupies a distinctive homesite that naturally welcomes residents and guests alike. Its prominent location reflects the home’s role as the gateway to the community while providing a peaceful setting for daily life.
Rooted in classic American residential design, The Bentley House is distinguished by balanced proportions, authentic materials, inviting porches, and carefully crafted architectural details. Every element has been thoughtfully composed to create a home that feels welcoming, refined, and deeply connected to its surroundings.
Designed to bring people together, the home’s flowing interior creates comfortable spaces for conversation, celebration, and everyday family life. Whether hosting friends, sharing a meal, or enjoying a quiet evening at home, every room reflects a spirit of warmth, generosity, and connection.
Thoughtfully integrated technology, energy-efficient systems, and contemporary conveniences enhance everyday living while preserving the home’s classic architectural character. The result is a residence that feels both welcoming and effortlessly suited to modern life.
The Bentley Manor is the estate for the buyer who wants to anchor the street.
It is the first home a visitor sees. It carries the name most closely tied to the historical event itself. It is, in the most literal sense, the doorway to Madison Manor – the home that defines what the rest of the street is.
The right buyer for the Bentley Manor is someone who understands what that role is worth.
