Stone steps rise through a hillside of pachysandra to a midcentury modern home nestled among the trees. Inside, the living room pairs high ceilings and warm wood paneling with beautiful ceramic tile floors and a wood-burning fireplace. Wide windows look into the surrounding branches, bringing the landscape into view. The living room opens to the kitchen and dining area, giving the main spaces an easy flow. A hallway leads to one bedroom with a full bath across from it. The bedroom at the back of the house has its own en suite bath, and a stackable washer and dryer are tucked into the layout. Outside, a slate patio offers a place to gather, while a one-car garage and off-street parking add convenience.

Built by Thomas Colt in 1865, 42 Wendell Avenue is a striking Italian Villa style property with a rich place in Pittsfield's history. Once owned by Simon England Sr., who deeded it in memory of his wife, the building later became the Women's Club of Pittsfield and most recently served as the Whitney Center for the Arts. The arched entrance opens to more than 7,700 square feet across 15 rooms. Soaring ceilings, inlaid hardwood floors, ornate fireplaces, carved wood mantels, and substantial original woodwork lend character throughout. Tall windows bring natural light into the rooms, and a sunroom offers a bright space overlooking the grounds. The property's scale and layout invite a range of possibilities. Rooms on both floors could accommodate professional offices or studios, while the

Built by Thomas Colt in 1865, 42 Wendell Avenue is a striking Italian Villa style property with a rich place in Pittsfield's history. Once owned by Simon England Sr., who deeded it in memory of his wife, the building later became the Women's Club of Pittsfield and most recently served as the Whitney Center for the Arts. The arched entrance opens to more than 7,700 square feet across 15 rooms. Soaring ceilings, inlaid hardwood floors, ornate fireplaces, carved wood mantels, and substantial original woodwork lend character throughout. Tall windows bring natural light into the rooms, and a sunroom offers a bright space overlooking the grounds. The property's scale and layout invite a range of possibilities. Rooms on both floors could accommodate professional offices or studios, while the

The sellers built this cottage in the woods in 1987 and have kept it beautifully ever since. It sits well back from the road under towering oaks, nearly surrounded by New England stone walls, on a lane most people don't know exists. Permanently protected land is across the way, and no other house can be seen. Wind moves through the trees, birds are everywhere, and turkeys, deer, foxes and hummingbirds cross the yard. Inside, a wood stove anchors one large open room, with two bedrooms and a full bath on the first floor. A screened porch keeps the evenings bug free, and the newer two-car garage has a finished room above. The Otis beach on Big Pond is a 0.7 mile walk, and Tanglewood for music is about 30 minutes away. Priced within reach for year-round residents and part-timers alike.

Fantastic investment opportunity on Wahconah St! This four-family property offers immediate income potential with two front, two bedroom units ready to rent while you complete the two rear, one bedroom units and build additional value. The front units feature attractive hardwood floors, tile in the kitchens and bathrooms, and a distinctive interior layout that adds charm and character. Outside, enjoy a spacious backyard with a utility shed and added privacy from neighboring properties on only one side and at the rear. Conveniently located within walking distance of BMC and North St., this property is full of potential for investors, owner-occupants, or buyers looking to expand their portfolio.

Own a Piece of History, Meticulously maintained by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both entertaining and intimate family life, this c1930, 6800 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately fireplaces anchor the formal living spaces. Enjoy panoramic views and privacy from the grand porch overlooking 4 pristine acres. A state-of-the-art kitchen featuring Wolf and Sub-Zero, and no expense spared Geo-Thermal heating/cooling, owned solar.

Tucked away in a peaceful, private setting, this charming mid-century ranch offers easy one -level living , warm and inviting. Featuring 3 bedrooms and 2 full baths, the home combines classic character with fresh updates. New oak floors throughout, fresh interior and exterior paint create a clean, move-in ready feel. Relax by the fire or enjoy time on the screened porch or deck. Minutes to town, Taft Farm, Guido's, Skiing and other notable Berkshire attractions.

COMMANDING VIEWS OVER LAKE GARFIELD WITH A STUNNING MOUNTAIN BACKDROP, this beautifully updated home offers charm with modern refinement. Original architectural character has been thoughtfully preserved, while expansive windows fill the home with light and frame the breathtaking scenery. Recently renovated chef's kitchen, first floor primary bedroom, and loads of closet space address today's needs. And could there be any better spot to watch sunsets than the expansive front porch? What's more, a well-appointed suite in the separate carriage house offers flexible space for guests, a home office, or artist's studio. Features include eight private acres, high speed internet, low Monterey taxes, and proximity to the Monterey bathing beach and the incomparable tomatoes at Anna's farm stand.

Your private Berkshire retreat! Sweeping views of Squaw Peak, surrounding mountains, 42 beautiful acres with trails, seasonal brook, room for pool, tennis court, family compound. Warm, welcoming 4BR, 4.5 bath, home with room for family, friends, gathering or quiet escapes. Sun-filled fireplaced LR with picture window, cozy window seat framing the view; elegant formal DR with window wall and fireplace. Spacious chef's kitchen with island, dining area, TV area, comfy wood stove, leading to the large screened porch and expansive deck--perfect for morning coffee, summer dinners or simply relaxing. 3 main-level BRs include ensuite primary. Above-grade LL offers office, 4th BR, bath, inviting fireplaced family room. 2-car garage. 1 mile to downtown Great Barrington.

Move right into this stunning single-family home at highly desirable Berkshire Country Meadows. Nearly new and impeccably maintained, this spacious home offers the ease of condominium living with the feel of a private residence. The open-concept design features a beautiful kitchen, dining area, and living room with a cozy gas fireplace, perfect for entertaining or everyday living, and a separate first floor office with French doors for privacy. The first-floor primary suite boasts a walk-in closet and en suite bath while the walkout lower level expands the living space with a generous family room, two additional bedrooms, full bath and private patio. With 4 bedrooms, 4 full baths, and exceptional space throughout, this home is simply gorgeous and ready to enjoy. Clubhouse, pool, tennis.

Move right into this stunning single-family home at highly desirable Berkshire Country Meadows. Nearly new and impeccably maintained, this spacious home offers the ease of condominium living with the feel of a private residence. The open-concept design features a beautiful kitchen, dining area, and living room with a cozy gas fireplace, perfect for entertaining or everyday living, and a separate first floor office with French doors for privacy. The first-floor primary suite boasts a walk-in closet and en suite bath while the walkout lower level expands the living space with a generous family room, two additional bedrooms, full bath and private patio. With 4 bedrooms, 4 full baths, and exceptional space throughout, this home is simply gorgeous and ready to enjoy. Clubhouse, pool, tennis.

Discover your dream space blending blending comfort, convenience and style. This well maintained four room, 2 bedroom, 1.5 bath Condominium offers a harmonious blend of features and thoughtful upgrades. The Kitchen beckons with a stylish center island, perfect for culinary explorations and casual dining. Enjoy the flexible living spaces including a versatile, mostly finished basement that could be ideal for a home office, entertainment hub or a serene retreat. The home provides privacy and a sense of community. Recent upgrades include designed for modern peace of mind. New HVAC system installed in 2024. New Water Heater installed in 2025. Roof covering replaced in 2025. Embrace out of doors with your own private patio that offers tranquility for morning coffee and evening relaxation.

Welcome home to 68 Doreen Street! This inviting 3-bedroom, 1-bath ranch offers comfortable one-level living in one of Pittsfield's most desirable neighborhoods. The spacious eat in kitchen features granite counter tops and stainless steel appliances and opens nicely into the living room. Step outside to discover a truly special private backyard, beautifully enclosed with a full fence and designed for relaxing and entertaining. Enjoy two spacious decks, unwind in the hot tub, or take advantage of the shed for extra storage. A one-car detached garage adds convenience and functionality. With its welcoming feel, fantastic outdoor space, and desirable location, this home is ready to create years of wonderful memories!

Welcome home to this cozy two-bedroom, one-bath home nestled on a quiet street. Full of charm and inviting spaces, this home offers a comfortable layout and the perfect blend of character and convenience. Enjoy your morning coffee or unwind in the evening on the lovely front porch, a welcoming spot to relax and enjoy the neighborhood. Out back, the fenced-in backyard provides a private space for entertaining, gardening, pets, or simply enjoying the outdoors. A garage adds valuable parking and storage space, while the peaceful street offers a quiet residential setting. Whether you're a first-time buyer or looking for a comfortable place to call home, this property is ready to welcome you. Come take a look at what this home has to offer!

Offering a flexible layout and convenient first-floor living. The main level features two bedrooms and a full bathroom with a newer tub surround, along with hardwood floors, granite countertops, and vinyl replacement windows. Upstairs, you will find two additional walk-through rooms offering plenty of flexibility for a bedroom, home office, playroom, or bonus space. The basement features high ceilings and offers great potential for future finished living space, with a slider providing direct walkout access to the driveway. A brand-new heating system adds to the home's appeal and provides peace of mind for the next owner. Conveniently located near the desirable Lanesboro Elementary School. Call today to view!