THE ULTIMATE FOUR SEASON BERKSHIRE RETREAT- Tucked away on 3.6 serene acres, this bright & airy single-level home is the perfect year-round escape. This completely renovated home offers an open concept main living area including the dining room, efficient eat-in kitchen with stainless steel appliances & family room with wood stove, perfect for relaxation & entertaining. Two additional guest rooms & a den. The newly completed primary suite boasts a beautiful bathroom & an oversized walk-in closet versatile enough for a home office. Outside, the private grounds feature a dining patio, fire pit, gazebo & shed. Located just minutes from the slopes of Ski Butternut & downtown Great Barrington, this turnkey property also features a proven track record as a short & long term rental MORE

Prime investment opportunity! This five-unit property features a desirable mix of four, one-bedroom apartments & one, two-bedroom. All units have their own separate heating & electrical systems! Convenient location ensures high demand due to proximity to stores and the hospital. On-site parking. Detached garage/workshop could be rented separately for additional income or used as storage for tenants.

Step into this beautifully updated 3-bedroom, 3-bathroom with a lretreat nestled in one of Jiminy's most family-friendly neighborhoods. 2 bedrooms and 2 Full baths on the 1st floor. The open-concept living area features floor-to-ceiling windows that flood the space with natural light, highlighting the elegant hardwood flooring and cozy fireplace. The gourmet kitchen boasts quartz countertops and top-of-the-line stainless steel appliances, perfect for entertaining. The primary suite offers a spa-inspired bathroom with a walk-in shower. Outside, the meticulously landscaped, fenced-in patio provides a private sanctuary, complete with plenty of room for al fresco dining. Enjoy the convenience of being just a short walk from the slopes and local shops. Upstairs boosts a spacious loft.

This beautifully positioned Berkshire retreat offers the perfect blend of privacy, comfort and natural beauty. Nestled on a peaceful country road, this inviting home is surrounded by scenic woodlands and mountain views while remaining conveniently close to the cultural attractions, outdoor recreation, and vibrant communities that make Berkshire County so desirable. Inside, you'll find warm and welcoming living spaces, ideal for both everyday living and entertaining. Enjoy a quiet morning coffee overlooking the views or simply unwinding after a day of hiking, skiing, or exploring the Berkshires, this property delivers the lifestyle buyers search for. An oversized heated workshop/garage with artist loft & half bath is simply magnificent for a multitude of occupations or hobbies. Incredible

Just up the hill from downtown Lee, enjoy this well kept 3 bedroom home on almost a half acre. The fenced in backyard includes a new inground pool with retractable cover, hot tub, studio/pool house, and garden shed. The first floor bathroom has been recently remodeled.

Bordering protected land and moments from the Appalachian Trail, this light-filled contemporary offers privacy, comfort, and an easy connection to the natural beauty of the Berkshires. Set on one acre in a peaceful Sheffield location, the home features vaulted ceilings, open gathering spaces, and a flexible layout designed for both everyday living and entertaining. The spacious kitchen flows into the dining and sitting area with direct access to the deck, creating an inviting indoor-outdoor feel. The living room is anchored by a beautiful gas fireplace and oversized windows that bring in natural light throughout the day. Three well-proportioned bedrooms include a primary suite with spa bath.

Welcome home to this spacious raised ranch located in a highly desirable neighborhood! This well-maintained property offers five bedrooms and two full baths, providing plenty of room for family, guests, or a home office. The inviting family room is perfect for gathering and entertaining, while the two-car garage adds convenience and storage. Step outside and enjoy the oversized deck overlooking the beautiful built-in pool an ideal setting for summer fun, outdoor dining, and relaxing with friends and family. With generous living space, great amenities, and a sought-after location close to schools, shopping, and local attractions, this home is a wonderful opportunity you wont want to miss.

OPEN HOUSE - Saturday, July 11, 11-1. Discover a truly exceptional opportunity to own a spacious 3-bedroom seasonal cottage on 1.3 acres of uniquely private land in one of the Berkshires' most desirable lakeside enclaves. Nestled in the serene and exclusive Beachwood community on Stockbridge Bowl, this property offers the perfect balance of natural beauty, privacy, and cultural access. Residents enjoy steps to a private beach, tranquil surroundings, and proximity to the region's finest cultural destinations. The home's inviting open-concept layout features a bright kitchen, dining, and living area centered around a cozy fireplace. Cathedral ceilings, updated appliances, and thoughtful upgrades throughout add modern comfort to this classic retreat

Welcome to 28 Mountain Pond Lane, a stunning raised ranch nestled on a private 3.29-acre parcel in New Ashford, MA. This charming home features 3 bedrooms and 2.5 baths, eat in kitchen & great room currently used as a studio offering ample space for comfortable and flexible living. The oversized 3-car garage provides plenty of storage, while the large multi-tiered deck and beautiful concrete patio in the rear create the perfect outdoor oasis for entertaining or relaxing. Surrounded by mature gardens, this property exudes tranquility. Additional highlights include a backup generator and various other features that enhance the home's appeal. Experience serene living in this picturesque setting--your dream home awaits!

Beautiful 4 bedroom contemporary on Lilybrook Road. Vaulted entry way leads to living (sitting) room flanked by formal dining room. Also on the first floor is oversized great (family) room with fireplace, large eat-in kitchen and private master (in-law) suite with full bath and jet tub. The second floor has another master suite with full private bath, two additional bedrooms, and a second full bath. This is perfect for a multi generational family. The basement has plenty of storage and a dry, carpeted rec room with a wet bar and a half bath. The grounds feature mature landscaping and privacy. The roof, skylights, and gas fireplace are newer (installed in 2016). Home is on a private street with a cul-de-sac and is within walking distance to BCC and the state forest. Bosquet and Jiminy Pe

Welcome to your private retreat in the Crystal Pond community, set on just over 2 acres of beautifully wooded privacy. This 4-bedroom, 3.5-bath residence blends refined comfort with natural serenity, offering a true Berkshire escape. Soaring cathedral ceilings, skylights, and expansive windows fill the home with natural light, highlighting rich wood plank flooring and a warm, elevated design throughout. The main living area features a fireplace, while a separate den is enhanced by a wood stove insert that provides efficient, comfortable heat and a cozy atmosphere. The thoughtfully designed layout includes generously sized bedrooms, including a second-floor bedroom with a private loft space, ideal for a reading nook, office, or creative retreat. Two upstairs bedrooms each enjoy access to

Welcome to 4 Birch Hill Rd. By appointment only. This private retreat set on over 44 acres is the perfect fit for the Auto enthusiast, woodcraft, cabinet making, Hobby farm, the options are endless! Live off the grid with solar power. The owner has not had an electric bill in over 10 years. There is an Eversource credit as well as quarterly renewable energy credits that transfer with the property. The wood furnace will heat the house and Steel garage. There is also oil and propane. Live the easy life in the 3/4 bedroom home with a beautiful three season room to enjoy your morning coffee, a maintenance free Trex deck to savor the beautiful starry sky and peaceful nights. The owner of this home is the original builder. Pride in homeownership is evident throughout.

Elegance Meets History on 1 Eaton Lane! Tucked away on a quiet, sought-after street just minutes from the Country Club of Pittsfield & only 10 minutes to vibrant downtown Lenox, this remarkable Colonial seamlessly blends timeless character with extraordinary versatility. Offering just under 5,000 square feet of living space, this historic estate presents a rare opportunity for those seeking a home with a story. The main house is a masterclass in classic architecture, featuring period details enhanced by thoughtful modern updates. High ceilings, gleaming hardwood floors, & charming front & back staircases ground the home in history, while the spacious layout provides endless room to breathe. The heart of the home is a sophisticated kitchen, featuring rich cherry cabinetry, new SS appliance

Set on over 2 acres in beautiful Egremont, this lovingly maintained four-bedroom, 2½-bath home blends classic character with thoughtful updates and additions made over the years. Built in 1920's, the house retains the warmth and craftsmanship of its era, including charming built-ins and inviting spaces that make it feel truly like home. A large deck provides the perfect setting for morning coffee, summer gatherings, or simply taking in the peaceful surroundings and lovely seasonal views. The property offers plenty of room to garden, explore, and enjoy the outdoors. A barn and chicken coop add to its country appeal. A detached garage with a large workshop provides excellent space for vehicles, tools, hobbies, or projects. The acreage offers privacy and a wonderful sense of space while

At the end of a quiet dead-end road in Sandisfield, this c.1892 four-bedroom farmhouse sits less than twenty feet from the Wild and Scenic West Branch of the Farmington River, a federally protected, free-flowing trout river. Four bedrooms. Two full baths plus a half. 2,516 sq ft. 4.61 acres. Beautifully transformed interior: a granite-island kitchen rebuilt from the ground up, wide softwood floors, working brick fireplace, cast-iron clawfoot tub, first-floor primary opening through French doors to a stone patio, stairs to lawn and river. Kitchen and dining open to a deck over the water. Quarry-granite three-car garage, studio cottage with grandfathered footprint, and a second river parcel with 19th-century mill history included. Flood Zone A12; elevation certificate available. READ MORE

Rare opportunity to own a substantial two-family home in one of the most desirable locations in the Berkshires. Overlooking meadows, sheep pastures, mountains, and Naumkeag, this special property is also just a short walk to Stockbridge Main Street. Each spacious unit offers 3 bedrooms, 1.5 baths, and hardwood floors throughout. The grounds are truly magical, with mature trees and a peaceful setting that feels tucked away while remaining close to everything. Currently fully tenant occupied, one unit will become vacant in September, creating the perfect opportunity for owner occupancy while generating rental income from the second side. Multi-family properties in this area are exceptionally rare. See Supplement

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.

Discover the exceptional lakefront lifestyle in this beautifully renovated, move-in ready 2-bedroom, 2-bath residence on Onota Lake. Bathed in natural light, expansive walls of windows frame captivating water views from the living room, dining area, and kitchen, creating a seamless connection to the outdoors. A welcoming fireplace adds warmth and charm, while efficient mini-split systems provide year-round comfort. The spacious primary suite offers a private bath and a serene retreat. Outdoors, a lakeside deck, fire pit and private dock create an inviting setting for entertaining, boating, and relaxed Berkshire living. A truly special waterfront offering.

Fantastic opportunity to own a home in a peaceful cul-de-sac within the desirable Cornwall Estates. This lovely home sits on a level lot w/ almost 2.5 bucolic acres. Spanning just over 2,000 square feet, the home features a convenient first-floor primary bedroom and bathroom, vaulted ceiling in the living room and a screened in porch that leads to a large, partially fenced in backyard. Many recent updates and upgrades including kitchen,bathrooms as well as furnace and central AC system replacement. All of this and a heated community pool nearby and Great Barrington just minutes away, make this home ready for the next owners to create their own Berkshire journey and memories.

SOUTH BERKSHIRE COUNTY, UPDATED VILLAGE CENTER HOME & OFFICE This graciously restored vintage house has all the benefits of an ideal Sheffield setting with walkability to restaurants, Bushnell-Sage Library, Dewey Hall, post office, bank, and churches. With residential/commercial zoning, the house features an above-garage private large office/studio, a 1,000 sq. ft. outbuilding with plumbing and electric service, 4 auto car-bay doors, and a separate parking area. There are several possible uses for the property, including a business and/or accessory dwelling unit for possible rental income. The home itself is spacious and bright, combining period detail with updates. High ceilings, wonderful light, crown molding, soapstone counters, farmer's sink, cherry cabinets, & built in hutch.