214 W Chestnut Street 202

Where History Lives Beautifully Some homes simply provide shelter. Others tell a story. Behind the stately brick façade of the historic Ulster Academy lies a residence that celebrates both the craftsmanship of another era and the ease of modern loft living. Originally constructed in 1870 as Ulster County's largest school, this remarkable landmark has been thoughtfully reimagined into one of Kingston's most distinctive residential addresses. Perched on the second floor, this light-filled 1,078-square-foot loft is defined by its remarkable sense of volume. Twelve-foot ceilings lift the space skyward while oversized windows bathe the interior in changing natural light throughout the day, creating an atmosphere that feels at once expansive, serene, and inspiring. The open floor plan offers exceptional flexibility, inviting you to shape the home around your own vision--whether as an elegant primary residence, a sophisticated weekend retreat, a creative studio, or a seamless live-work environment. Wide doorways, elevator access, and dedicated off-street parking make everyday living as effortless as it is beautiful. Above it all, a 3rd story shared rooftop terrace offers sweeping views across Kingston's rooftops and the surrounding hills--a quiet place to greet the morning, watch the seasons change, or linger over an evening glass of wine as the city glows below. Step outside and become part of the Rondout's enduring rhythm. Wander along the historic waterfront, where centuries-old architecture now houses celebrated restaurants, intimate cafés, independent galleries, boutiques, and music venues. Watch boats drift through the marina, spend Saturday mornings at the farmers market, or discover a new favorite corner with every stroll. Here, history isn't confined to museums--it is woven into daily life. For those drawn to places with authenticity, architectural character, and creative energy, Ulster Academy Lofts offers something increasingly rare: a home that feels as inspiring as the neighborhood that surrounds it. This is more than a loft. It is an opportunity to become part of one of Kingston's most storied buildings and one of the Hudson Valley's most vibrant communities. Monthly HOA Fee: 400.