A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and restaurants. Nestled amidst beautiful, well-maintained grounds, this residence exudes curb appeal. The apartments have all been thoughtfully updated and come equipped with outdoor space, access to laundry facilities, and exceptional parking.

A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and restaurants. Nestled amidst beautiful, well-maintained grounds, this residence exudes curb appeal. The apartments have all been thoughtfully updated and come equipped with outdoor space, access to laundry facilities, and exceptional parking.

Immaculate Center Hall Colonial in one of Lee's most desirable neighborhoods. Beautifully maintained and move-in ready, this inviting home offers 3 bedrooms, 2.5 baths, plus a spacious game/bonus room. The first floor features a wonderful eat-in kitchen with granite counters and abundant cabinetry for the home chef, a large living room with fireplace, formal dining room, and gleaming hardwood floors. Upstairs, the en-suite primary provides a comfortable private retreat with two additional bedrooms. An attached two-car garage adds everyday convenience. Set on a beautiful residential street with a deck--perfect for grilling, morning coffee, or a glass of wine at the end of the day. Exceptionally well cared for plus, need more space, there is a walk out lower level waiting to be finished.

Experience year-round magic at this classic 1925 lakefront cottage, set on a private point of Shaw Pond with 60' of direct shoreline. Panoramic water and mountain views unfold from the screened porch, while a stone fire pit sets the scene for sunset gatherings. Inside, renovated, light-filled spaces include an open living room with stone fireplace, fully equipped kitchen, updated full bath, and laundry. Upstairs, three cozy bedrooms and a half bath offer a peaceful retreat. A private summer dock invites kayaking, paddleboarding, and motorized boating, while winter brings ice fishing and skating. Just 13 minutes to downtown Lee, 24 minutes to Tanglewood, and 20 minutes to Jacob's Pillow. Berkshire lakefront living at its best, in every season!

Welcome to 365 Deer Run, a beautifully refreshed four bedroom, 3.5-bathroom home tucked into the sought-after Otis Woodlands community. Inside, 2,297 square feet of cedar-wrapped warmth unfolds beneath cathedral ceilings and skylights, with east-facing windows that bring beautiful morning light into the home throughout the year. A window-lined three-season porch extends the living space and offers an inviting place to linger through spring, summer, and fall. The home is designed for both comfort and ease, with features including soapstone countertops, gas heat with Nest controls, a private sauna, and a brand-new roof. Thoughtfully updated and move-in ready, it offers the rare combination of character, modern comfort, and minimal fuss.

This 1860's Italianate has been thoughtfully restored and improved over the years. With nearly 3800sq ft, this magnificent home offers ample space and a flexible floor plan. Gleaming hardwood floors, timeless trims and mouldings, and decorative fireplaces adorn many of the rooms. A beautifully remodeled, eat-in kitchen is ideal for those who love to cook! There are 3 full bathrooms, and 5 spacious bedrooms. The Main Suite includes a walk in closet with custom cabinetry, and a full bath with a soaking tub. An option for a first floor bedroom opens up possibilities for multi-generational living. The second floor offers a bonus space perfect for a family or media room. Need a home office or studio? There are plenty of suitable options. Many recent improvements add value and convenience to

A rare c.1780 estate poised for a spectacular second chapter. Perched above the village of Monterey, Ledgehurst offers a canvas for the ultimate Berkshires compound: a main house with room to create the private, en-suite retreat of your imagining, an indoor pool and sauna complex ready to be reborn as a true wellness escape, plus two barns that open the door to possibilities few properties can match. A guest house, a creative studio, a multi-generational haven; the vision is yours to shape. With over an acre of grounds, a short stroll to Lake Garfield's sandy beach, and downtown Great Barrington just 15 minutes away, this is a once-in-a-generation opportunity to bring true Berkshires living to life. Sold as-is; buyers encouraged to perform due diligence on scope and permitting.

Open House Sunday August 2 From 2:30 to 4:00. Looking to enjoy lakeside living year round? This one bedroom home sits on three contiguous lots which provide the opportunity to expand your living space in the future. It overlooks it's own private lake lot allowing you to enjoy lakefront activities and everything that Ashmere Lake has to offer The home features an open floor plan with large windows overlooking the lake. At one end of the cathedral ceiling, a ship's ladder leads to an enclosed bonus room above the large bedroom The lower level walkout has a foyer entrance, multipurpose room, including the laundry room and a mechanical room Outside you'll find a separate deck, fire pit, and a large grassy yard with plenty of room for a garden.

Charming open-concept Ranch includes a separate abutting building lot in the heart of the Berkshires on a quiet non-through street! This beautiful, move-in ready Ranch offers 1,959 sq ft of bright, inviting living space on the main level. Finished 1159 sq ft basement with full bath adds extra space, perfect for a game room, holiday gatherings. The dining area connects to a large kitchen with newer quartz countertops. Great room features a natural gas fireplace. With 3 spacious bedrooms,3 full bathrooms, there's plenty of room for everyone. Outside, enjoy a welcoming front porch with nice landscaping or host a barbecue on the large back deck. Complete with an attached 2-car garage. Close to Berkshire attractions, 15 minutes to Tanglewood, and minutes to shopping, this home truly has it all!

Welcome home to this beautifully maintained and thoughtfully cared-for residence, ideally situated on one of Southeast Pittsfield's most desirable dead-end streets. Offering exceptional curb appeal, mature landscaping, and a peaceful garden-like setting with a wonderfully private backyard, this charming home showcases quality craftsmanship, timeless character, and pride of ownership throughout. Designed for both everyday living and entertaining, the spacious sunroom is filled with natural light and overlooks the backyard, creating the perfect place to relax or gather with family and friends. Step outside to enjoy the inviting in-ground pool, private patio, and tranquil outdoor setting.

Versatile mixed-use property pairing a sophisticated second-floor apartment with a flexible first-floor residence that doubles as an ideal commercial or gallery space. Overlooking a tranquil year-round brook and a private backyard, the offering sits right downtown Egremont and includes the convenience of an ample garage. Property Highlights Second-Floor Apartment: Sophisticated, charming living quarters featuring high-quality finishes, total privacy, and serene views of the brook and grounds. First-Floor Mixed-Use Space: Currently configured as a comfortable residential apartment while offering incredible potential for an art gallery, retail boutique, or commercial enterprise. Ample Garage: Generous garage space providing excellent storage, parking, or workshop potential.

Versatile mixed-use property pairing a sophisticated second-floor apartment with a flexible first-floor residence that doubles as an ideal commercial or gallery space. Overlooking a tranquil year-round brook and a private backyard, the offering sits right downtown Egremont and includes the convenience of an ample garage. Property Highlights Second-Floor Apartment: Sophisticated, charming living quarters featuring high-quality finishes, total privacy, and serene views of the brook and grounds. First-Floor Mixed-Use Space: Currently configured as a comfortable residential apartment while offering incredible potential for an art gallery, retail boutique, or commercial enterprise. Ample Garage: Generous garage space providing excellent storage, parking, or workshop potential.

NEW PRICE! Beautiful 2021-built ranch privately situated on 7.74 acres in Otis, offering the perfect blend of modern comfort, privacy, and Berkshire outdoor living. This 3-bedroom, 2-bath home features an open floor plan, vaulted ceilings, hardwood floors, central air, open kitchen with granite countertops, stainless appliances, and a stunning stone fireplace. The spacious primary suite and attached 2-car garage add everyday convenience. Outside, enjoy a 30' x 30' detached garage, fire pit, apple trees, wooded privacy, and plenty of room for recreation. Big Pond and the town beach are just around the corner, making this an ideal year-round home or Berkshire getaway. A newer home, substantial acreage, two garages, central air, and recreation access--all in one property.

Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 &3 all in 2023.Can also be purchased as part of a investment portfolio 13 Park Street Stockbridge, MA MLS#249532

'Located in Great Barrington's coveted residential neighborhood surrounded by million-dollar-plus estates, this home offers an unbeatable entry point into luxury Berkshire living. Designed with distinct living zones, the two-level layout provides the ultimate setup for weekend guests, remote working, family room or great potential for multi-generational living. The main living level features bright, flowing living space framed by natural views, perfect for effortless entertaining after a day in town or on the trails. Enjoy beautiful mature landscaping, outdoor living spaces and prime proximity to downtown Great Barrington at an accessible price point

Quitessential 1830's side hall Colonial....charming home located in the village of Interlaken in the town of Stockbridge, MA....just minutes to Lenox, Stockbridge center and the Berkshire Botanical Center. Listen to the babbeling water from the Larrywaug Brook and walk just steps to the small town park.....sit on the deck or around the firepit to soak in the atmosphere of privacy and peacefullness. This 3 bedroom, 1.5 bath house has been miticulously updated including: roof, windows, deck, painting, kitchen, baths, cement clapboard, wood flooring, laundry on main level. Full walkout basement, oil heat, central air, town water, town sewer.....garage is partitioned for a workshop but can easily be converted to a one car garage again.

This beautiful home offers an abundance of natural light through its large, expansive windows, creating a warm and inviting atmosphere throughout. Post and beam construction, well equipped kitchen open to living room (with 30' ceilings) and dining room create ease of entertaining. First floor primary en-suite with a private deck overlooking the back yard and beautiful view. This home also offers a private, spacious first floor in-law suite, plenty of closet space, and sliders leading out to the pool, ideal for extended family or guests. The den is a comfortable meeting space between the in-law suite and the main part of the home where you can sit by then fire on chilly days. Between the hot tub, in-ground pool, and yard it's a complete package! 20 minutes to Williamstown, MA.

Cable Mills, industrial mill buildings restored into beautiful homes with 12ft to 16ft tall ceilings, massive windows, and exposed brick and beam, steel and timber throughout, stainless appliances, granite countertops, gas ranges, generous closets and in home laundry. Cable Mills offers stunning views of the 'Purple Mountains' and the Green River. Homes are one, two or three bedrooms in single level flats, lofts and townhome styles totaling 61 residences. Outdoor spaces including the Outdoor Living Room with a fire pit, grills and seating along the river walk. The main building offers a community lounge, fitness center, interior bike storage, package delivery room, dog wash and on-site professional management. Photos of similar home. #TownhomesWilliamstownMA #MillBuildingCondo

Nestled in the heart of the Berkshires, this exceptional Williamstown residence offers more than 4,000 square feet of thoughtfully designed living space, featuring 4 spacious bedrooms and 3 bathrooms. Enjoy breathtaking mountain views from the expansive wrap-around deck--an ideal setting for morning coffee, outdoor entertaining, or simply taking in the beauty of every season. Inside, generous living spaces provide the perfect balance of comfort and elegance, making this home equally suited for everyday living or hosting family and friends. Ideally located just minutes from the cultural and recreational attractions that make Williamstown one of New England's most desirable destinations.

Ben's of Lee is an iconic downtown store and a familiar Main Street destination that has served generations of Berkshire residents and visitors. This rare mixed-use offering includes the prominent brick commercial building, the established business, inventory, furniture, fixtures, and equipment--providing a turnkey opportunity for its next owner. The ground-floor retail space features excellent visibility, large display windows, and a classic storefront with tremendous character. Four one-bedroom apartments upstairs provide additional rental income and strengthen the property's investment appeal. Located in the heart of downtown Lee, near shops, restaurants, cultural attractions, and the Massachusetts Turnpike,