You'll find classical charm around every corner in this beautiful Victorian farmhouse nestled in the town of Cheshire. The main residence showcases timeless details including hardwood floors, granite countertops, original millwork, and beautifully preserved staircases and trim. The living space features three bedrooms, a full bath, formal dining room, living room and den. An attached two-bedroom guest house or in-law suite provides ideal accommodations for guests or multi-generational living and can also serve as a potential income-producing apartment. Situated on almost a half acre with an oversized barn-style garage. Relax and enjoy Berkshire summer evenings on the spacious front porch, the perfect spot for a hot coffee and a good book.

Designer style one level living garden bungalow with beautiful Berkshire bucolic pastoral and mountain views! Easy living and low maintenance with 2 bedrooms and 2 full bathrooms, conveniently located on the Lenox/Pittsfield line. Beautifully renovated with open floor plan, spacious living room, beautiful kitchen and dining room w/amazing views. Primary bedroom leads to back deck with large primary bathroom. Pastoral views from front deck and October Mountain views from large back deck. Beautifully landscaped. Cottage potting shed, cedar fence and much more. Convenient to Tanglewood and all cultural and recreational venues the Berkshires has to offer! Natural gas heating system and central air. Turnkey home!

Perched on a gentle hill, this charming ranch offers the perfect blend of comfort and privacy. Surrounded by woods in the backyard, you'll enjoy peaceful views and the beauty of the nature right outside your door. This inviting home features three spacious bedrooms and two full baths, providing plenty of room for family and guests. With its quiet setting and warm, welcoming layout, this hilltop retreat is ideal for anyone looking to enjoy simple living with a scenic backdrop.

Welcome to this charming Cape-style home, set on 3.8 acres of peaceful, wooded land. With five bedrooms and two bathrooms, this spacious residence is perfect for a large family or hosting guests. The primary bathroom features a luxurious whirlpool tub, offering a perfect retreat for relaxation. Additional highlights include a walkout basement, providing extra living space or storage potential, and a wheelchair-accessible front entrance for added convenience. Stay connected with high-speed Internet from Spectrum while enjoying the privacy and natural beauty of this serene property - a true gem in a picturesque setting

Proudly offered for the first time, this well-cared-for one-owner Colonial is set in a highly desirable neighborhood on corner lot. Offering 4 spacious bedrooms and 2.5 baths, the home features gleaming hardwood floors and a classic, timeless layout ideal for both everyday living and entertaining. Step outside to a large, lush backyard perfect for relaxing, play, or gatherings. Thoughtfully maintained over the years, this home combines warmth, space, and location, presenting a wonderful opportunity to enjoy a true neighborhood setting in a home that has been genuinely loved. Natural gas, multi zoned heating, and underground utilities.

Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street--where every cafe, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life.Over 1,800 sq. ft. of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that evoke another era. Every detail--from the textured walls to the light pouring in at all hours--creates a sense of romance and possibility.The home is thoughtfully divided: one wing offers a spacious bedroom and lounge with guest alcove, while the other wing hosts a dining area, kitchen, and charming nook for work or rest.

Welcome to this charming, freshly painted throughout and carpeted, 3-bedroom, 2 -bathroom condominium located in the desirable Greylock Village. This end unit offers comfort, convenience, and access to a peaceful and picturesque setting in the heart of the Berkshires. Whether you're looking for a full-time residence or a vacation getaway, this property is perfect for all lifestyles. The large living and dining areas are perfect for entertaining or relaxing at home. The living room offers a fireplace for those winter snow storms, plenty of counter space for meal preparation in the large kitchen area. There are three generously sized bedrooms: The primary bedroom is on the first floor with a full bathroom and linen closet. Two bedrooms and full bath complete the upper level.

Indian Lakes property with gorgeous lakes two beaches for swimming or kayaking &clay tennis courts. This log sided 3 bedrooms 2bath cabin sits in the Hill towns of Becket, Middle of the Berkshires easy to get to Stockbridge, Gt Barrington 3 ski areas 7 lakes and October State forest.2 new baths and new kitchen with stainless appliances and granite counter tops is ready to show. Cozy up to the wood burning fireplace. Two bedrooms and full bath on the main level, Kitchen living room and dining are all open under a vaulted wood ceiling.The downstairs has a full bath & Bedroom with a wood stove and large den. I love the little screened in Porch off the kitchenand a large Barbecue deck off to the side all facing the woods about 8 mins' from I-90 Lee, Stockbridge /Lenox exit.

Beautifully renovated home with plenty of space for everyone. This home offers 4 bedrooms, 2.5 baths, and a huge yard. Fully finished walkout basement adds another living room, 1/2 bath, and 4th bedroom. There is no sign yet on the property. The sale of this property is contingent upon the seller closing on their next home which is already under contract and scheduled to close on or before April 16th, 2026. Ring camera on the property.

Live in the center of Great Barrington with a private backyard of almost 3 acres on the river! This renovated farmhouse has an inviting kitchen with cozy wood stove, first floor primary suite and 2 spacious bedrooms with a shared bath on second floor. Beautiful wide-plank floors and built-ins preserve this home's history. A solar rooftop system brings energy efficiency and electricity credits. Front porch, back deck and two car garage with second story and an EV charger complete this in-town gem!

Tucked into a small neighborhood just outside of South Egremont village, this delightful renovated hip-roof cottage offers single level living convenient to everything. A mahogany and cedar finished front porch welcomes you into a bright living room open to an updated kitchen and cozy dining area, complete with a fireplace hearth. This slab built home boasts a primary suite with private bath with subway tile & marble floor. A 2nd bedroom is served by a hall bath, with 2 nearby bonus rooms - flexible space for an office, studio, or guests. The 16' x 24' deck and a 384-square-foot screened porch with mahogany decking and cedar paneling offer ideal space for enjoying the view of the spacious backyard. This property is being sold as-is. The seller will NOT provide a Title 5 Inspection.

Welcome to 40 Baldwin Avenue with over 2800 square feet of living space. The formal living room flooded with natural light features a pass through, wood burning fireplace. A versatile dining room, presently configured as a den, easily adapts to your needs. An expansive kitchen features ample storage, a desk area and a dining space. Additional first floor living spaces include a family room with fireplace and a mudroom/office area that leads to the newer, trex deck. There is also a full bathroom on the first floor. Located on the second floor are the primary ensuite with a recently renovated bathroom, a third full bathroom and three additional bedrooms, all with double closets. The home also features an aluminum lock shingle roof that is approximately 6 years

The Woolen House stands as a rare piece of prestigious Hinsdale history. Once the home of the Woolen Mill superintendent, it has been fully reimagined for modern living. The craftsmanship is unmistakable: original woodwork, 16 inch brick construction, and a sense of permanence rarely found today. Inside, five bedrooms, two full bathrooms, a spacious laundry, and a versatile first floor room offer function & flexibility. At its heart is a brand new kitchen with never used stainless steel appliances, custom cabinetry, & fresh finishes ready for its first chapter. Ten high-efficiency mini splits, each backed by a 7-year warranty, ensure comfort year-round. Set in a quiet rural corner of the Berkshires, yet an easy drive to Ashmere Lake, trails, Tanglewood, Jiminy Peak, & other cultural hubs.

This home is ready for its new owner. A complete professionally remodeled interior. New Septic System, New insulation, New Windows, New Kitchen and Appliances, Freshly Painted, Fiber Optic Internet available, New gravel Driveway, New Boiler, New hot water heater, Brand new LED lighting within the entire home. New tile work in the the 2 full baths. Laundry conveniently located on the same level as the bedrooms. No detail has been overlooked. You will not be disappointed with this remodeled home.

Multi-family in a convenient location, walking distance to town and shopping, bus line nearby.Well maintained. The perfect location, walking distance to restaurants and shopping, public transportation nearby.

Riverfront on Silverbrook, Feels like new. Beautiful Setting. 3 bedrooms 3 baths. Sit on the back deck and watch the water flow. Inside you will find a huge kitchen with stained concrete counter tops and Stainless appliances. Primary with full bath is on the main floor along with laundry and a 1/2 guest bath. Upstairs 2 large bedrooms with a full bath. The lower-level family room is partially finished with windows and a double glass door to back yard. A Beautiful Berkshire home. Move in ready. Low taxes, wood floors, front rocking porch. Perfect

Welcome to this well maintained one-level ranch style home located in a great neighborhood, offering comfort, efficiency, and thoughtful upgrades throughout. Enjoy the convenience of walkability to schools and downtown Lee, along with easy access to Mass. Pike, making commuting and travel effortless. This home features a new eat-in kitchen featuring stainless appliances, rich navy lower cabinets, and warm butcher block countertops. Open shelving for an airy, modern feel, blending style and function in a welcoming space perfect for everyday living. Three bedrooms and two full bathrooms, including a primary bedroom with a private primary bathroom. Cozy living room with hardwood floors, new front foyer with shiplap wall and bench seat. Oversized 2 car garage with high doors offers....

Mid-Century Classic with Timeless Appeal: Split-Level RanchStep back in time to the golden era of design with this beautifully preserved 1963 Split-Level Ranch. A true mid-century classic with a lot of character. It's ready for modern-day love and personal touches. This home perfectly blends the clean lines of the Ranch style with the functional, multi-level living of a split-level, offering distinct spaces for every activity. This 4-bedroom home has had multiple updates in the last 4-7years. Windows, roof, driveway & the kitchen with beautiful cabinets, counter tops & stainless appliances. Situated in a great, secluded neighborhood while remaining incredibly convenient--you're just minutes from town centers and all necessary shopping.

Welcome to this solid, well-built four-bedroom, two-bath raised ranch, built in 1969 and nestled in a wonderful neighborhood just minutes from beautiful Laurel Lake. The main living area features a beautiful brick fireplace anchored in the center of the room, hardwood floors throughout the first floor, offering warmth and timeless appeal. This home provides a functional and flexible layout with a large kitchen/ dining area and a finished lower level that includes an additional fireplace and bar, ideal for a recreation room. Separate office and finished laundry room, two car garage is conveniently located underneath. Deck overlooking the large fenced in backyard creates a great space for relaxing or hosting gatherings. A solid home with great bones, waiting for you to make it your own!

Build to suit. This new ranch construction modular home offers an open concept kitchen, dining & living room space, The home open, sun-filled spaces with an open floor plan that is designed to capture Pontoosuc lake and mountain views from every room on the main living level. 3 bedrooms 2 baths. Walkout lower level ready for additional finished space. Purchase as specked or chose upgrades to finish home to your desires. Lake access available within walking distance. Building plans available at request.