A Charming Southeast Pittsfield Cape with classic character and an inviting sense of ease. This three bedroom and one bathroom home offers a spacious living room, dedicated dining room and an inviting country kitchen. A first floor bedroom and bathroom provides flexibility while two additional bedrooms are upstairs. Outside, a sweet backyard with a stone wall creates a lovely setting for relaxing or entertaining. This is comfortable and warm home with plenty of appeal and ready to be enjoyed. Open houses: Friday, September 11th 4:30pm - 6pm and Saturday, September 12th 10am - 11:30am.

Beach days, porch evenings and Tanglewood concerts make this the perfect three-season Berkshire cottage. Vaulted ceilings and a fieldstone fireplace anchor the living room, while two bedrooms and a versatile loft provide comfortable space for family and friends. The screened in-porch extends the living space for long summer afternoons and evenings, while the dining room is filled with windows that bring nature inside. Set in the welcoming community of Mahkeenac Heights, this cottage is just a short walk to the town beach at Stockbridge Bowl and close to the Berkshires' many cultural attractions. A wonderful retreat for enjoying all the Berkshires have to offer!

Bring your contractors and your imagination to this unique fixer-upper, an old carriage barn with an attached apartment. The spacious barn features original beams with large open areas. The lush grounds are complemented by charming rock walls and rustic outbuildings. With a convenient location close to all the Berkshire attractions, this property is ideal for transformation into a one-of-a-kind retreat!!

A charming year round cottage just steps from the private community beach. This irresistible one bedroom and one bathroom cottage delivers the best of waterfront living without the waterfront maintenance. It is warm, inviting with gorgeous water views and an abundance of character making it an idyllic four season escape for quiet mornings by the lake, summer afternoons on the beach, crisp autumn weekends and cozy winter getaways. Simple arrive, settle in and enjoy the best of the Berkshire or you can make this enchanting cottage your year round home.

Don't miss this rare opportunity to own this private, meticulously maintained waterfront sanctuary. The grounds feature a charming English garden, an expansive deck and a private dock for launching kayaks, offering outdoor living at its best. The main level features an eat-in kitchen with custom cabinetry, a living room, sunroom ideal for gatherings, an office, mudroom with laundry and a first-floor primary suite with full bath, providing convenient single-level living. This home includes central AC and a backup generator for year round comfort and peace of mind. With beautiful views and just moments from downtown, this property blends privacy, comfort and convenience in a truly special setting.

Light, airy & effortlessly inviting this 4 bedroom & 3 full bath home is made for Berkshire Living. Walls of windows & a sun filled sunroom bring the surrounding woodlands into nearly every room, while a brand new oversized deck sets the stage for long summer dinners & relaxing afternoons. A separate grilling deck offers the perfect spot for outdoor cooking & easy entertaining. Spacious interior rooms, abundance of natural light & multiple gathering spaces make this an exceptional year round retreat. Then there's the Otis Wood Lands lifestyle w/ an incredible array of amenities including a private lake, clubhouse, swimming pool, tennis/pickleball & playground. It's the perfect pairing of a beautiful home & a welcoming community offering everything you need to relax, play and entertain.

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket doors that provide charm and flexibility. Every detail has been curated to embody warmth and sophistication, creating an inviting ambiance that is both refined and welcoming. Ideally located just moments from downtown Lenox, Tanglewood, a local municipal airport and a charming farm, HomeFarm, directly across the street. Highwick offers an unparalleled sanctuary in the heart of the Berkshires!