Welcome to this beautiful and inviting home in Pittsfield's most sought-after Southeast neighborhood. This is a unique opportunity to live at Wellesley Park, a small city-owned and beautifully maintained park, where homes rarely come on the market because once you live in this community, you will never move again! This well maintained, light-filled 2,100 square foot home boasts a large formal living room with over-sized picture windows at each end and fireplace; a very large kitchen with five-burner cooktop and double wall ovens; an office, half bath; dining room; and den making up the downstairs.

Nestled in the Historic District of picturesque Heath, this unique former artist loft blends character, space, and tranquility in a truly special setting. Offering over 3,300 sq ft, the thoughtfully expanded home features 3 bedrooms, 3 baths, and soaring light-filled spaces throughout. A spacious kitchen wing overlooks the private yard, while the second-floor deck offers peaceful views of the surrounding landscape. The property also includes over 2 acres of open meadow and a small barn, perfect for hobby farming, horses, or gardening. Tucked away in a serene and private location, this distinctive retreat captures the charm and beauty of Hilltown living.

Year round retreat in the Lake Buel Community. Thoughtfully designed spaces, cozy & unpretentious. The living area, comfortable for family & guests, has vaulted ceiling and Gas Fireplace, making this home just as inviting in the cooler months. Kitchen is functional, attractive and updated. Simple lines, wainscoting, wood floors, ductless A/C units. The Sunroom is perfect for Dining, board games or snuggling up with a book. Wonderful sunny deck, and a grassy lawn with fire pit. Upgrades include fenced yard & Generator! A shed to store your kayaks & bikes. Deeded Lake access. Minutes to Great Barrington town center, Butternut Ski Area & Hiking Trails. Easy access to Lake, just over the knoll.

Set on 16 private acres, this four-bedroom, one-and-a-half-bath home has been lovingly updated while preserving its rustic warmth and character. Soulful wood floors, cozy living spaces, and a versatile attic retreat give this home an authenticity you simply cannot manufacture. A two-story wood stove heated barn bursting with natural light makes for an ideal studio or creative workspace. Step outside to a spring-fed pond reaching ten feet at its deepest and perfect for a summer float, a morning swim, or simply watching the light dance across the water. A gazebo offers a quiet perch to read, sketch, or simply breathe it all in. And when the day calls for deeper restoration, a private sauna awaits. Close to Jacob's Pillow, Becket Arts Center, Lee, and Tanglewood. A true sanctuary.

Bring your vision and finish this one-of-a-kind Savoy home your way! Privately set on 3.5 wooded acres with mountain views, this seller-built home offers nearly 2,900 sq. ft. of flexible living space and an oversized two-car garage below. Much of the heavy lifting is complete, including sheetrock, electrical, plumbing and heating systems. Choose the flooring, kitchen, bath fixtures and exterior decking to reflect your own style. The versatile layout offers three bedrooms, with the lower-level bedroom equally suited for use as a spacious family room. Vaulted ceilings, abundant natural light, pellet heat and an outbuilding add even more appeal. A rare opportunity to complete a newer home in a peaceful Berkshire setting!

Surrounded by nature with 21 acres of private trails to roam. This architecturally striking 3BR/2BA home features a soaring cathedral-ceiling great room opening to a wrap deck, plus a lower-level hangout space perfect after a day outdoors. Central air, efficient propane systems, and an oversized 2-car garage make it easy to enjoy in every season. Minutes to Queechy Lake, Chatham, Hudson, the Berkshires, and skiing just 15 miles away. A private retreat with huge redecorating potential -- ideal for year-round adventure or a high-demand AirBnB escape. Short notice showings may be possible.

Turnkey perfection awaits on Partridge Road in Pittsfield. This beautifully renovated 4-bedroom, 2-bath raised ranch offers effortless modern living with gleaming hardwood floors, crisp interior paint, and an airy, sun-drenched open layout. The main living area flows seamlessly into the dining and kitchen spaces, creating an ideal setting for entertaining and everyday comfort. With four bedrooms and two fully updated bathrooms, there is abundant flexibility for guests, a dedicated home office, or multi-generational living. Step outside to your private backyard oasis, showcasing a spacious yard and a sparkling in-ground pool ready for summer gatherings and weekend relaxation. Highlighted by fresh exterior paint, updated finishes throughout, and true move-in readiness, this home delivers

Discover the timeless appeal of this beautifully renovated mid-century modern split-level home, thoughtfully designed across four spacious levels. Offering two bedrooms and two full bathrooms, this unique property features flexible living space with the potential for a third bedroom, home office, family room or hobby space to suit your needs. The stunning living room showcases soaring vaulted ceilings, hardwood floors, expansive windows and a french door leading to the deck, creating an open and inviting atmosphere. Situated on two scenic acres with breathtaking mountain views, this property offers the perfect blend of privacy and tranquility. Recent and extensive renovations provide a stylish move-in ready

Immaculate 3-bedroom ranch with additional 750 square feet of finished living space in lower level. Move in condition, cathedral ceiling in living room and 2 full baths, Prmary with ensuite. Set way back off Park Street North on 0.62 level acres. 8+ acres owned by Land Conservation in your back yard adds peace and privacy.

DON'T JUDGE A BOOK BY IT'S COVER! This is a must see. Beautifully renovated from 2020-2025, this 3-bedroom, 2-bath Ashmere Lake cottage offers an ideal blend of modern updates and timeless lake-house appeal. The open living, kitchen, and dining layout provides bright, flexible space, complemented by an enclosed front porch for additional seasonal enjoyment. Located just a short walk to the private association beach, this property also features an indoor wood stove and an inviting outdoor firepit area, making it a perfect year-round or seasonal getaway.

Envision waking up in this beautifully renovated New England farmhouse in quaint Lenoxdale Village. Enjoy morning sunrises on the front patio and quiet evening dinners on the terrace, all just minutes from the world-class culture of Tanglewood and the iconic downtowns of Lenox and Stockbridge. Inside, original hardwood floors flow throughout a versatile layout featuring 3-4 bedrooms, a cozy office space, and a spacious, freshly updated kitchen with a breakfast nook and extra pantry space. Outside, the large open yard is anchored by a charming car barn--ideal for summer projects, kayaks, bicycles, and flexible loft space. Come make this home your Berkshire dream!

Country Living at its best! Discover the perfect blend of space, comfort and opportunity with this large 4-bedroom, 2-bath home on 10 acres (consisting of two 5-acre lots). The welcoming layout includes a first floor bedroom and a convenient first floor laundry, making daily living easy and accessible. The great room boasts cathedral ceilings, creating an open and airy feel, perfect for gatherings. The spacious kitchen features ample counter space and cabinetry. Upstairs are three more bedrooms and a full bath. Need even more room? Theres an unfinished room over the 3-car garage just waiting for your finishing touches. Outside is a large fenced backyard with plenty of room for gardens, play and pets.

Set on two-thirds of an acre in a residential area, walkable to all Great Barrington has to offer, this versatile home offers 4+ bedrooms and 3 bathrooms. The main floor boasts two bedrooms, a dedicated office or guest space, one and a half baths, laundry, as well as the main living, dining, and kitchen areas. Upstairs you will find 2 additional bedrooms and another half bath. Wood-burning fireplace, exposed beams, hardwood floors, and a spacious three-season porch overlooking the stone patio all make this property a must-see. The lot offers a large yard as well as the patio, a two car garage and an additional outbuilding.

Turnkey Berkshire Retreat Near Stockbridge Bowl & Tanglewood - Embrace effortless seasonal living in this beautifully maintained, vintage three-season cottage. Nestled on a quiet, unpaved lane in the desirable Mahkeenac Heights community, this two-bedroom home offers the quintessential Berkshires getaway. Recent thoughtful updates include fresh flooring and an opened-up floor plan that maximizes natural light and flow. Step outside onto expansive decking designed for alfresco dining. Whether you are spending your mornings at the local lake beach or your evenings taking in world-class music at nearby Tanglewood, this private haven offers prime proximity to the best of Lenox and Stockbridge.

Welcome to your own private slice of the Berkshires! Nestled on 3.09 picturesque acres in the town of Cheshire, MA, this beautifully maintained 3- bedroom, 2 bath home offers the perfect blend of comfort, privacy and natural beauty. From the moment you arrive, you'll appreciate the pride of ownership this well kept property. The inviting home features spacious living areas, comfortable bedrooms with the primary having a balcony to relax on. Step outside and discover what truly makes this property special. The expansive yard is beautifully landscaped, providing plenty of space for gardening and recreation, or simply relaxing while enjoying the peaceful surroundings. A tranquil pond adds to the property's charm.

This beautifully maintained 1,900 sq. ft. ranch offers comfortable single-level living with a bright, open floor plan and plenty of natural light. 3.21 Acres - Two Garages plus a Full Walkout Basement! The inviting kitchen features marble countertops, while beautiful hardwood floors and a custom fireplace add warmth and character throughout. The spacious walkout basement includes a Smith furnace and Fire Chief wood stove, providing flexible heating options. Set back from the road and abutting Crystal Pond, this peaceful private setting is the perfect place to enjoy the beautiful fall season. Property features two garages, two driveways, a barn, ample parking, and hookups for a future hot tub. Conveniently located just 34 minutes to Westfield, 19 minutes to Lee, and 26 minutes to Pittsfiel

Impeccably cared for and thoughtfully maintained, this sprawling ranch offers comfortable one-level living with a flexible layout and plenty of space both inside and out. The sun-filled living room welcomes you with abundant natural light and a wood-burning fireplace, creating a warm and inviting gathering space. There is a well-appointed kitchen and dining room, while a bright and peaceful sunroom provides the perfect spot to relax and enjoy the surrounding setting. The home features three bedrooms, including a primary suite with a recently remodeled bathroom. Another bedroom offers the convenience of its own three-quarter bath. The spacious dining room could easily be reimagined as a fourth bedroom, home office, den, or additional living space to suit your needs.

Completely renovated contemporary home on almost 10 acres of marvelous land. The home sits back from the road, offering tranquility and privacy. The first floor features two bedrooms and an additional room with a wood-burning fireplace which can be used as a recreation room or a third bedroom. Downstairs you will also find a large laundry room with epoxy flooring, and a brand new full bathroom. The second floor offers an open concept and features a brand new kitchen with quartz countertops, a great room with a wood stove, a cozy dining area and a new full bathroom with a jetted tub. You will feel like you are at a spa! Relax and enjoy nature from your tub or step outside to the new deck that wraps around the home.

Welcome to the historic Simmons Cottage located at 2 Melrose Street in Adams, MA. This Victorian gem, completed in 1901, perfectly blends its 19th-century character with modern convenience. Situated on a .24-acre lot in the heart of Adams, the 2,406-square-foot residence features 4 bedrooms, three bathrooms, office, and full attic. The home's historic elegance shines through its preserved curved front porch, original woodwork, stained-glass windows, and rare Lincrusta ceilings. This home has been updated to provide efficiency, including a new roof, upgraded heating system, and a modernized kitchen with top appliances. A standout feature is the unique historic carriage barn, relocated and repurposed into an incredible five-car detached garage for your vehicles and hobbies!

Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra storage. Inside, enjoy abundant natural light in the glassed-in sunroom or relax on the multiple porches and decks. A key feature is the large, private in-law apartment, perfect for multi-generational living or rental income. Ideally located in the heart of Sheffield village, you'll enjoy the comforts of downtown just steps from your doorstep.