Move-in ready and filled with upgrades, this southeast Pittsfield colonial home offers five bedrooms and flexible living space. The first floor includes a bedroom and full bath, while the second floor features a primary ensuite plus three additional spacious bedrooms. Enjoy a beautifully landscaped, very private backyard with an above-ground pool and convenient access from the kitchen deck--perfect for summer entertaining. The finished basement recreation room w/660 sq.ft. is included in total sq.ft. Centrally located, the home is approximately 10 minutes from major shopping centers and less than 10 minutes to Lenox center and Tanglewood.

Meticulously maintained and lovingly cared for, this spacious four-bedroom, two-and-a-half-bath home offers the perfect combination of comfort, quality, and location. Featuring generously sized rooms throughout, this home provides ample space for both everyday living and entertaining. Pristine wood floors lie beneath the carpeting, offering the opportunity to uncover their timeless beauty. Recent improvements, including a new roof, providing peace of mind, while gas heat and central air conditioning ensure year-round comfort. Set in one of the area's most desirable neighborhoods and within a highly sought after school district, this property offers a truly special connection to its surroundings.

Welcome to 551 Tamarack Road! A beautifully updated and maintained Cape-style home, nestled on 1.28 acres in picturesque Pittsfield, MA!This charming 4-bedroom,2-bath residence boasts a perfect blend of modern amenities and classic charm. Step inside to discover a spacious, light-filled living area, ideal for gatherings and relaxation.The eat in kitchen features contemporary finishes and ample storage, seamlessly connecting to the dining area. Enjoy the convenience of 2 well-appointed bathrooms and generously sized bedrooms, perfect for family and guests.Outside, the expansive yard offers endless possibilities for outdoor activities, gardening, or simply enjoying nature.Meticulously maintained and set in a peaceful setting, this home is a true gem just waiting for you to make it your own!

Little Acorn House - a warm and inviting Otis Wood Lands Contemporary with three bedrooms and three full bathrooms. The dappled morning light brightens the open kitchen/living/dining area. A spacious four-season room, bedroom and full bath complete the main floor. Second floor includes two bedrooms and a full bathroom. Walk-out lower level with great game room space, office/den and full bathroom. New roof 08/2026. Association amenities include pool, tennis/pickleball courts, fitness room, lodge, playground, beach, and lake for non-motorized boats. $4,000 reserve fund fee due from buyer at closing. Dishwasher does not work. Wood stove disconnected prior to closing.

This immaculate Lion's Head condominium is a perfect pied a terre or weekend residence. The inviting living room features custom shelving, a propane fireplace, and sliders to a private deck overlooking a wooded setting. The updated kitchen is equipped with stone countertops, and high-end Bosch appliances, including a range and microwave/convection oven. A dining area with vaulted ceiling and skylight adds to the bright, airy feel. Upstairs, both bedrooms feature vaulted ceilings and new windows. Additional highlights include central air, engineered wood flooring, and attached one-car garage. Lion's Head amenities include a Gunite pool and tennis court and its central location allows for easy access to town. Near private schools, restaurants, and Metro-North at Wassaic. A true gem!

4,008+/- sqft 1850 Greek Revival in excellent condition w/large, open, bright rooms on 1st level incl wood-burning F/P, eat-in Cherry kitchen w/Shaker cabinetry - updated/bright lighting thuout- 2nd flr w/4lg BRS. 1 full, 2 half baths, period hardwood floors throughout, private rear deck. POST & BEAM BARN. Lg parking area... in hamlet center moments to Old Chatham, Berkshires, Chatham Village and half-hour to Capital District via I90/Parkway exit one mile away. Property leased through November 2027. Arrangements for earlier availability may be possible but not guaranteed. As a matter of brkrage policy, any co-op brokr comm, if offered, is payable solely and exclusively to a lic re brkr/brkrage company. Showings M-F 9AM-3PM, no wknd showings granted.

Welcome to this stately raised ranch nestled in one of Pittsfield's most sought-after neighborhoods--Barkerville. Offering 1,896 square feet of thoughtfully designed living space, this home blends comfort, efficiency, and natural beauty in a truly special setting. Set on a cozy, private lot, the property is framed by mature evergreen trees, classic stone walls, and a peaceful brook flowing through the backyard. A grand entrance and custom walkway create a striking first impression, while the home abuts conservation land, providing direct access to scenic hiking trails and a serene, nature-filled backdrop year-round. Ideally located in the heart of the Berkshires, you're just minutes from world-renowned destinations including Tanglewood, the summer home of the Boston Symphony

Set along a bucolic country road, this charming New England Farm House offers wonderful space, character, and a host of recent updates. The inviting floor plan features large, comfortable rooms with wood floors throughout. The updated kitchen includes new countertops and appliances, creating a fresh and functional gathering space. Relax on the screened porch or entertain on the deck while enjoying the peaceful country setting. Ideal for outdoor enthusiasts with excellent biking, hiking and walking right from the property. Skiing and town center are just minutes away, offering recreation and convenience.

On the Dalton/Hinsdale line atop Tully Mountain! A wonderful chalet style raised ranch on just over 5 acres offering the kind of privacy, space, and versatility that makes a home feel truly special! Built and maintained by its original owners, this is a solid, well-constructed home that has been exceptionally well cared for over the years. Generous rooms, abundant closet space, and seasonal mountain views add to its appeal! The main level features an inviting living and dining area centered around a wood burning fireplace with a substantial hearth and sturdy mantel. Sliders from both the living room and dining room open to the wonderful south facing composite deck, creating an effortless connection between the interior and outdoor living spaces.

Nestled on scenic Mount Washington, this beautifully maintained contemporary home offers the perfect blend of privacy, comfort, and modern updates. The thoughtfully designed floor plan features 3 bedrooms, including a desirable first-floor primary suite with a private bath and direct access to a secluded deck. With 3.5 bathrooms, this home provides exceptional space for family and guests.The light-filled interior showcases beautiful cherry and maple peg hardwood floors, oversized windows, and sliding glass doors that seamlessly connect the indoor and outdoor living spaces. The inviting living room features a fireplace with a wood stove insert, creating a warm and welcoming atmosphere.The well-appointed kitchen is designed for both everyday living and entertaining, complete with

Tucked into the rolling hills of Great Barrington just minutes from downtown and the slopes of Ski Butternut, The Turning Point is a storied 3,600-square-foot Berkshire landmark operating as an active short-term rental. Steeped in history dating back to its 1800s stagecoach tavern roots, the property showcases an enduring dual-facade of classic New England brick and weathered clapboard. Inside, original period charm takes center stage with wide-plank wood floors and glowing fireplaces, perfectly paired with a rare, substantial footprint featuring 7 generous bedrooms and 6.5 bathrooms. Designed for effortless hosting, this expansive retreat offers an incredible canvas for a lucrative rental investment, a boutique bed-and-breakfast, or a magnificent private country compound.

Location, location, location! Ideally situated within easy walking distance of the village, elementary school, and Tanglewood, this charming ranch offers comfortable single-level living in a quiet, desirable neighborhood. The large, level and semi-private backyard provides plenty of room to relax, entertain, garden, or enjoy the above-ground pool. Inside, the home features a spacious open living area currently used as a dining and family room, separate living room, eat-in kitchen, three bedrooms, and a full bath with tub. Step directly from the kitchen onto the deck overlooking the pool and expansive backyard. Additional highlights include an attached two-car garage, full basement with four versatile rooms, and a designated laundry space complete with a laundry chute!

Tucked well back from the road on 3.5 private acres, this modern, lightly used home offers an effortless blend of low-maintenance living, single-story convenience, and quintessential Berkshires charm. Designed with an open, light-filled layout, the main level features gleaming hardwood floors and an seamless flow throughout the common living areas. At the heart of the main floor is a inviting living room with a gas fireplace framed by a stone surround and hearth, an updated kitchen, and a generous primary suite complete with a large walk-in closet.Enjoy indoor-outdoor living with a covered front porch, a spacious screened porch, and an expansive wrap-around deck perfect for entertaining or taking in the peaceful surroundings.The expansive finished walk-out lower level extends your living

Discover the epitome of lakeside living in this exceptional 4-bedroom, 2-bath home nestled in the desirable Otis Wood Lands community. This fully furnished residence seamlessly combines comfort and entertainment, featuring bright, spacious rooms and an expansive deck perfect for relaxation or hosting gatherings. Enjoy modern conveniences such as energy-efficient heat pumps, remote-controlled security systems, and Alexa-compatible features, all designed to enhance your lifestyle. Step outside to find a private beach and swimming area just moments away, ideal for launching your canoe or kayak. The community offers a wealth of recreational amenities, including a lodge for social events, a fitness center, tennis and pickleball courts, and a heated outdoor pool.

OPEN HOUSE CANCELLED! Experience the perfect blend of professional utility and luxurious comfort at 1 Almon Ave., a beautifully constructed and impeccably maintained retreat located in a BG-zoned area. This home offers an exceptional opportunity for those looking to operate a business or maintain a home-office setup without sacrificing lifestyle quality. The main residence provides four spacious bedrooms, including a convenient first-floor bedroom w/ a walk-in closet, complemented by four full bathrooms. At the heart of the home, the gourmet kitchen showcases custom hickory cabinetry paired with solid granite countertops. The second floor--which, along with the stairs, will feature new carpet--includes three additional bedrooms, a family room, a full bath with laundry, and a

Escape to your own island retreat where each day is a peaceful, waterfront sojourn. Nestled on an island in Big Pond, this tranquil waterfront property offers extraordinary privacy, natural beauty and modern comfort. Thoughtfully updated, the home features a masterfully renovated kitchen and bath, a first-floor bedroom and distinctive architectural details including cedar shakes, that create warmth and character throughout. All furnishings to stay. Mornings of seasonal birdsong and the delicate beauty of the new day invite ease and comfort both on the screened, full-windowed porch or on the two outdoor decks. Breathtaking views of the lake encourage leisurely relaxation while winding garden paths and natural stone walls enhance the property's timeless appeal

There is something wonderfully easy about Loft 209. Soft north light, restored wood floors, exposed brick and original mill columns give this 1,345 SF one-bedroom + study residence its character, while a thoughtful layout makes it exceptionally comfortable to actually live in. Conceived by celebrated architects LATENT Productions, Greylock WORKS reflects an uncommon respect for the historic mill, its architecture and its Berkshire setting. Original materials and industrial details have been preserved and celebrated, while highly custom modern interventions bring a quiet timelessness to the spaces. The result has a genuine sense of place--architecture that could only belong here.

Welcome to 4 Filomena Drive, where comfort meets the natural beauty of the Berkshires! Tucked away in a peaceful Southeast Pittsfield neighborhood, this inviting home offers a wonderful connection to the outdoors. Enjoy the tranquil backyard, bordered by a year round brook and beautiful views of the surrounding natural landscape. Whether you are grilling on the deck, entertaining on the patio, or simply enjoying the sights and sounds of nature, this property offers a perfect place to unwind. Inside, you'll find welcoming living spaces, an enormous finished basement, and plenty of room to make yourself at home. Enjoy the serenity of your own backyard retreat while staying just minutes from all the Berkshires has to offer!