Knoll Rock is a rare compound in the Berkshire foothills of Canaan, NY, offering privacy, history and versatility on 10 + acres. Located on a quiet and desirable dirt road surrounded by other charming Shaker vernacular homes and estate properties, the compound includes two fully restored historic residences on separate lots, seamlessly blending 18th- and 19th-century architectural character with modern luxury. Both houses were sensitively renovated by its English owner, a master craftsman inspired by the Cotswold-like landscape that surrounds the property. Well-suited for income generation, multi-generational living, or live/work scenarios, Knoll Rock has been successfully operated as both a short-term rental (rated 5 stars on Airbnb) and longer-term seasonal rental, hosting artists at nearby cultural institutions in Lenox, Mass. The main Dutch Colonial home (c. 1760) boasts four bedrooms, four baths, two kitchens, original pre-Revolutionary ''shotgun'' chestnut beams, and wide-plank floors. The second farmhouse home (c. 1890) offers three bedrooms and two full bathrooms, including a first-floor primary suite, along with a detached guest cottage with kitchenette and bath. A picturesque barn and rustic shed add charm and functionality, while rolling meadows, mature trees, and deeded access to nearby Queechy Lake complete this idyllic country retreat. 91 Miller Road - A beautifully restored post-and-beam Dutch Colonial dating to 1760 and set on 2.79 acres, this distinctive property offers a rare opportunity to own a piece of early American architecture thoughtfully updated for modern living. Conveniently located between convenient the Berkshires and the Hudson Valley, the home features four bedrooms and four full bathrooms centered around a spacious open-concept living and dining area showcasing original ''shotgun'' chestnut beams and wide-plank wood floors - hallmarks of its 18th-century heritage - along with the contemporary addition of an eco-friendly bioethanol fireplace. The thoughtfully designed kitchen outfitted with premium appliances is complemented by a second full kitchen and upstairs guest suite, creating flexible options for extended family, guests, or rental use. A generous family room with an additional bioethanol fireplace provides added gathering space and may also function as a formal dining room or media room. All four bathrooms have been tastefully updated with European-style spa-like showers and contemporary fixtures, including one with a jetted tub. Outdoor features include a covered porch, a pergola with blue-stone patio, and mature landscaping that enhances the home's tranquil, wooded setting. 95 Miller Road - Set on 7.09 acres, this fully renovated 1890 farmhouse is rich in character, featuring original exposed ceiling beams and wide plank flooring throughout. The open kitchen and dining area were tastefully renovated in 2023, blending modern comfort with timeless appeal and anchored by a charming wood-burning stove with brick hearth. The home includes three bedrooms and two full bathrooms, with two bedrooms and one bath on the first floor. The primary bedroom offers direct access to a private outdoor deck. A third bedroom and full bathroom on the second floor - featuring a clawfoot soaking tub - provide added privacy, ideal for guests or a home office. The property also includes a separate guest cottage with its own kitchenette and full bath. Beyond, the land opens to a meadow offering versatile potential for agricultural use, livestock, a pool or a future building site. With the towns of Chatham, Lenox/Pittsfield, Hudson, Albany, and five ski resorts all within easy reach, this is a rare opportunity to own a turnkey compound in the Berkshire-Hudson Valley region offering exceptional charm, flexibility, and income potential. 91 Miller Road (MLS #20260630) and 95 Miller Road (MLS #20260630) can be sold together (MLS #20260628) or separately.