Just two miles from the center of Stockbridge, this beautiful four bedroom, three and a half bathroom home offers privacy, space and exceptional indoor outdoor living. The spacious primary suite features a large ensuite bath and separate his and her closets, and an additional closet with direct access to a full length deck shared access with the living room. The open floor plan connects the living room, dining area and kitchen, highlighted by soaring beamed ceilings abundant natural light, and a gas fireplace. A bright sunroom to choose a book from its floor to ceiling bookcases. The deck overlooks the mature landscaping, pool, and pool house. The walkout lower level includes a second kitchen, providing space for guests. A Berkshire retreat just minutes from the cultural attractions!

Lovely Carriage House in splendid location. Just minutes from prestigious Clark Art Institute with its world-renowned collection of French Impressionist and American Art, and the numerous trails wandering through the meadows and woodlands of its 140 acre campus, and a stone's throw from the outstanding Taconic Golf Club, this charming residence, once part of the Cluett Estate, affords privacy with its 1.4 acres as well as proximity to all Williamstown has to offer. The four bedroom, three and one half bath home features a stellar and spacious living room with large woodburning fireplace, a formal dining room opening to a screened porch overlooking the pleasing grounds, a warm bookcase-lined den with another fireplace, a kitchen with breakfast nook. and stone terraces. With ample room

Own a piece of Williamstown history with this beautifully preserved Greek Revival modern farmhouse, set along the Green River on just under 20 picturesque acres. This exceptional property offers a rare combination of historic charm and modern comfort, with ample acreage for farming or livestock, ponds, barns, an in-ground pool, and more. The main residence features 5 bedrooms and 4 bathrooms, while the attached guest house offers 2 bedrooms and 2 bathrooms, providing flexibility for extended family, guests, or multi-generational living. Step inside this timeless home to discover thoughtful modern upgrades designed for everyday living. A spacious mudroom at the rear entrance keeps daily life organized, while the stunning kitchen—complete with stainless steel appliances, granite countertops

Live, Love, & Play in Blythewood Estates priced favorable $250,000 less than assessed value for a quick sale to allow you enjoyment this beautiful Berkshire season. A private enclave near premier Lake Onota to experience idyllic living in the Berkshire hills while creating lasting memories. This stunning 6000+ sf, 5 Bedroom, 5.5 bath colonial is thoughtfully designed and beautifully set on 3.42 manageable acres with sweeping meadow views nestled perfectly to create peace in nature while centrally located minutes to the culture, arts, museums, eclectic dining and central to Tanglewood and The Clark Art. Three levels of living create a blend of fun and entertainment with a degree of separation on levels. First floor offers one level easy living with a dramatic two story primary bedroom suit

SPACIOUS, SINGLE-LEVEL CONTEMPORARY WITH PRIVACY AND HEATED IN-GROUND POOL in the coveted community of Harrington Woods. 6 bedrooms. 3.5 baths. Bright, open floor plan with a spacious kitchen open to the dining area. The Great room has a cathedral ceiling, a wood-burning fireplace, and glass doors leading to a large screened porch and deck. Primary bedroom suite with full bath has cathedral ceiling and glass doors leading to the deck. Finished walkout lower level is perfect for a gym, playroom, game room. In-ground heated pool surrounded by perennial gardens. Access to a community pool, and a tennis/pickleball court. Miles of hiking trails in the area and 15 minutes to swimming at Lake Garfield or kayaking at Lake Buel. 20 minutes to Ski Butternut. 10 minutes to Jacob's Pillow.

A remarkable offering of this restored 18th century Georgian home built in 1764 on almost 4 acres with the possibiilty of an additional building site as part of the listing price; with an early barn and shed opposite the Clark Art Institute. Once located on Main St where the College President's house now sits, it was moved by oxen to its current location in 1800. (RRBrooks.)Restoration efforts follow the Deerfield tradition of interior feather-edged sheathing and paneling, wide pine board flooring and a large colonial cooking fireplace with adjacent beehive oven in the keeping room. 4-5 bedrooms/3.5 baths.

Discover a prime commercial opportunity at 449 Pittsfield Road Lenox, MA. This expansive building boasts approximately 9,000 square feet and features eight versatile office suites, perfect for businesses of all sizes. With ample parking available, your clients and employees will enjoy easy access. Strategically located in a high-traffic area, this property benefits from excellent visibility and foot traffic, making it ideal for retail or professional services. Whether you're looking to invest or establish your business, this location offers a unique blend of functionality and convenience. Don't miss your chance to secure a spot in this vibrant commercial hub!

Nestled on over 3 private acres with an extraordinary 650 feet of frontage on Hayes Pond, this exceptional waterfront retreat offers sweeping elevated views, a private dock, sandy beach, and direct access to swimming, kayaking, and fishing. Designed to embrace its stunning natural setting, the home features expansive windows and multiple outdoor living spaces, including a wraparound deck, waterside gazebo, and screened porch with hot tub connection--perfect for entertaining or relaxing in every season. The bright open-concept interior includes 4 bedrooms and 3 full baths, highlighted by a dramatic great room with knotty pine ceilings, a wood-burning stove with stone hearth, and direct deck access overlooking the water. The spacious primary suite also opens to the deck and features its own

To Be Built Home - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 8.94-acre lot (MLS #248342), featuring a private well, installed septic system, underground electric, and a 1,000-gallon underground propane tank. A proposed septic easement accommodates an abutting lot. Lots may be purchased separately. HOA maintains driveway and common land. Covenants require a minimum 2,000 sq. ft. home with two-car garage. Taxes shown are for land only.

Hidden at the end of a long winding drive, this wonderful three-story Greek Revival home was built in 2001 and sits on over 34 private acres. The main level offers a living room, dining room, kitchen, half bath and a screened porch. Upstairs are two bedrooms and a full bath - all with hardwood floors, while the walkout lower level serves as either a third bedroom or a den, along with the laundry and utility rooms. Hike through your own woodland, then enjoy the area's renowned cultural attractions and outstanding dining, including the Old Inn on the Green and the Southfield Store Café. Nearby Umpachene Falls and York Lake offer swimming, while picturesque Rhoades and Bailey Road is one of the Berkshires' most scenic country roads, lined with beautiful homes, of which many are secluded.

Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly Views of October Mountain. Plenty of room for family and friends.

Income producing 8-family home with detached 3-bay garage , located on an almost half an acre corner lot ! The property is fully occupied, and the 3 garage bays are rented as well, offering additional income. The apartments have separate heat, hot water and electricity and there is plenty of off-street parking. This is a great opportunity to own a great rental property in a desirable town and convenient location, close to shops, restaurants. and other Easthampton attractions!

Income producing 8-family home with detached 3-bay garage , located on an almost half an acre corner lot ! The property is fully occupied, and the 3 garage bays are rented as well, offering additional income. The apartments have separate heat, hot water and electricity and there is plenty of off-street parking. This is a great opportunity to own a great rental property in a desirable town and convenient location, close to shops, restaurants. and other Easthampton attractions!

14 Unit investment opportunity! Located just outside of downtown Pittsfield and within walking distance to shops, restaurants, and the Colonial Theater. Classic brick exterior and excellent off street parking. All units feature one bedroom and separate utilities. Coin-op laundry located on site for additional income.

A prominent downtown Great Barrington location with an established professional tenant mix. Offering 6,121 square feet of commercial space on 0.48 acres. Built in 1900 and spanning two floors, the property features four office spaces and seven half bathrooms, providing a flexible configuration for professional and service-oriented uses. The building is fully occupied. Located in the heart of downtown Great Barrington with excellent visibility. Surrounded by an established mix of restaurants, shops, professional services, and cultural destinations. With its prominent location, existing tenancy, parking, and flexible two-story layout, 168 Main St. presents a distinctive commercial investment opportunity in the Berkshires.

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite—pool, fitness center, clubhouse, and tennis—all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite—pool, fitness center, clubhouse, and tennis—all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.

This iconic building has been home to one of the Berkshires most beloved businesses for over 50 years. Built in 1731 as the Egremont Tavern stage coach stop, it was expanded in the 1960s. The 2.2 acre lot provides substantial parking. The historic front section offers unique features like stone floors and exposed beams and fireplaces. The rest of the building consists of a series of lovely rambling spaces with rustic elements on the main and lower levels, and two rental apartments upstairs (one 3/1, one 1/1). This property offers a buyer an extraordinary opportunity: own an incredible income producing property in the bustling town of South Egremont.

Set on 60+ acres of manicured Berkshire grounds, this four-bedroom, five-and-a-half-bath single-owner home is a rare find. Cedar shingle roof, wide-pine floors and walls, natural stone finishes, and wood-burning and gas fireplaces speak to the craftsmanship throughout. The kitchen flows into an open living space with den and sitting room, creating cozy nooks perfect for gathering. A welcoming second-floor primary suite with en-suite bath wakes up to sweeping mountain views every morning. A fully appointed in-law suite with private entrance, kitchen, and bath offers exceptional accommodations for family or guests. Breathtaking views of the Berkshire Hills, with Jiminy Peak and Bousquet visible from the expansive deck. Close to Tanglewood, Jacob's Pillow, Lenox and Lee.

Welcome to Serenity Hill. This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road. Less than a mile from Wyantenuck Country Club and just five minutes from downtown Great Barrington. This home offers a peaceful sense of seclusion without ever feeling far from the heart of the Berkshires. Inside, you'll find an airy, open layout with natural flow from room to room, designed with both comfort and connection in mind.