88 Old Roxbury Road Roxbury CT

c.1790/1800 Colonial-Federal-style farmhouse located on a whisper-quiet and unpaved scenic country road in one of the most desirable areas of Roxbury. The character-loaded 3-story clapboard house is sited on a perfectly level 23+- acre property that includes a 19th century former smokehouse, and a historically significant English U-shaped barn framing a central courtyard that opens to the south, with open pastures and paddocks to the north, a stream running along the west boundary to the pond, and pine forest to the northeast. The property is accented by fieldstone walls and abuts Roxbury Land Trust, offering privacy within walking distance to nature preserves and trails.

Located a mere 90 miles from NYC you will feel a world away in this renovated antique home with its sophisticated feel and a sense of history as you note many lovely period details throughout. These include exposed hand-hewn beams, original hardwood flooring, four wood-burning fireplaces, and oversized 12-over-12 windows that allow natural light to bathe each room. The interior features a central fireplace surrounded by public rooms, including a formal dining room, library/sitting room, and formal living room. The country kitchen, complete with designer appliances and butler’s pantry, is located off the formal dining room in its own wing with cathedral ceiling. The kitchen opens to an informal dining area and keeping room that is flooded with natural light thanks to skylights and five sets of glass sliders that open to the gardens.

The primary bedroom on the second floor is en suite and has its own wood burning fireplace and all amenities. Two nicely scaled additional bedrooms share a full bath, and a flexible office bedroom completes this floor. On the third floor, two additional bedrooms share a full bath. Throughout the home are wide board floors, architectural details reflecting the period, and a sense of historic integrity.

A 12-by-26-foot guest studio/office, formerly a smokehouse, is a short walk from the main entrance. The 1.5-story structure has 2 rooms with a central brick fireplace, and boasts original finishes such as hardwood flooring, cathedral ceiling, exposed wood beams, and built-in shelving. The building is heated and cooled with split systems.

Further to the west is the English barn, a U-shaped structure formed by three wings attached with connecting structures. The exterior has a unified appearance, and construction is post-and-beam framing with primarily fieldstone foundation. Parking for more than 6 cars is possible, plus additional loft and storage space is available. Original horse stables remain and a temperature controlled locked room is included for wine storage or sensitive documents.

The three-building complex is a rare combination of tranquility, charm, and open space with plenty of natural light. The land is mostly flat, with two lawn areas leading to a pond.

A truly rare & exciting opportunity to own a piece of Roxbury history and one of the original homes in the area.

Other features include 3-zone air conditioning, oil heat, cedar shake roofing on all buildings, a split system in the smoke house, a temperature-controlled room in the barn, barn garage doors that are more than 8 feet tall, stream and pond. The deed restricts parcel across the street from building within 4-acre envelope (no one can build in front of this house). Abuts Roxbury Land Trust to the north, a stream to the west, and a mixed wood forest to the east provide complete privacy. Originally 220 acres.