The Definition of Ultimate Privacy! A masterpiece of a home invites the most fastidious prospect. Built with the utmost dedication to detail that no item too small was overlooked. The ability to expand and build to your heart's desire is here. Perhaps a pool, tennis court, even a football field is within your reach. This property consists of 200+ acres, a 6,700 sq. ft home, Primary En-Suite on the first level, 2 bay garage, Extra Large Enclosed Barn capable of sheltering a bulldozer with a private space up above. Nestled in the foothills of the Berkshires on beautiful winding country roads. A lovely vineyard just around the corner, a short 25 minute drive to BDL International airport and just under 3 hours to NYC and 2 to hours to Boston. Come make this your dream get-away!

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.

Enjoy the relaxing Berkshire lifestyle on a friendly cul-de-sac within walking distance of town and Lake Mansfield. As the first house built on the street, the property has matured beautifully -- seasonal flowering trees and pollinator-friendly gardens bring color and life to the yard from spring through fall. Cedar columns frame a distinctive front door that opens into 4,200 square feet of tastefully designed living space, where soaring ceilings, a linear gas fireplace, and built-in bookcases set the tone. The living room flows out to a screened-in porch with a treehouse-like view of the wooded backyard -- the perfect spot for morning coffee or summer evenings.The chef's kitchen is beautifully appointed with Wolf and Sub-Zero appliances and granite countertops, and opens to the dining

This inviting Ranch in highly desirable Southeast Pittsfield location, offers comfort, privacy, and breathtaking natural beauty. Abutting the serene trails and protected lands of the Mass Audubon Society at Canoe Meadows Wildlife Sanctuary, the property captures sweeping views for miles.Inside, hardwood floors and expansive windows fill the home with natural light, while the spacious living room with a wood-burning fireplace creates a warm, welcoming centerpiece. Enjoy year-round comfort with central A/C, and take full advantage of the home's outdoor spaces including a large welcoming front porch, a rear sun porch, patio and fire pit, perfect for relaxing or entertaining under the stars. 3 bedrooms, 1.5 baths, first floor laundry, and natural gas heat.

Experience idyllic country life and the best this area has to offer in this charming wood shingled house. Situated on two acres, this three-bedroom cape has an updated kitchen with stone counters which opens into the dining room. The spacious living room has a brick fireplace, built-in shelves and lovely French doors that open into a four-season heated sunroom with a vaulted ceiling and large windows that look out onto the property. Glass doors open onto a small porch that leads to the backyard. Enjoy days and evenings relaxing or entertaining outdoors with the fire pit, stone patio and the clawfoot tub converted into an outdoor shower. Upstairs are three bedrooms and a full bath. The large primary bedroom has double closets. Additional finished space adjacent to one bedroom could be

Open house is cancelled.Welcome to this well-cared-for three-bedroom, two-bath ranch in Adams. This home offers a bright, comfortable layout with hardwood floors, a spacious living room and an inviting eat-in kitchen with ample cabinet storage and updated appliances. The main level also includes nicely sized bedrooms and a full bath.The lower level adds valuable finished space with a family room, bar area, and an additional full bath, creating flexibility for hobbies, entertainment, or guests. Interior access leads to the attached one-car garage.Outside, enjoy a generous backyard with a deck, fire pit area, an underground sprinkler system, and room for outdoor activities. The home also features central air and is near the Ashuwillticook Rail Trail.

Welcome to this beautifully situated 3-bedroom, 1-bath home offering comfort, convenience, and breathtaking views of Mount Greylock.Nestled on a spacious corner lot, this property provides added privacy, extra yard space, and great curb appeal. The fully fenced-in yard is perfect for pets, play, gardening, or outdoor entertaining. Whether you're hosting a summer barbecue or enjoying a quiet evening under the stars, this outdoor space offers endless possibilities.Inside, you'll find three bedrooms filled with natural light and a full bathroom. The home's layout creates a warm and inviting atmosphere, ideal for both everyday living and gathering with family and friends.A detached two-car garage offers ample room for vehicles, storage, or even a workshop

Welcome to elegant single-level living in one of Lenox's most coveted locations. Ideally positioned on prestigious Saint Andrews Drive, this exceptional home offers privacy, comfort, and stunning views--just minutes from the heart of the Berkshires.This expansive 3,379-square-foot residence features four bedrooms and four full baths, thoughtfully designed for both everyday living and entertaining. Each bedroom includes its own private bath, ensuring comfort and privacy for family and guests alike.A grand living room with soaring ceilings and a double wood-burning fireplace flows seamlessly into a cozy den, separate office, and formal dining room. The gourmet eat-in kitchen is beautifully appointed and enhanced by custom woodwork and artistic tile details throughout.

Enjoy this charming three-bedroom Cape-style home located in desirable Southeast Pittsfield. Gleaming hardwood floors run throughout most of the home. The first floor features a comfortable living room filled with natural light and a fireplace, a dining room, and a kitchen, along with a first-floor bedroom and full bathroom. Upstairs, you'll find two additional bedrooms, along with extra space for storage.Additional highlights include a spacious basement offering ample storage, a workshop area, and a laundry room with an additional sink. The home also features a one-car attached garage, public water and sewer, and low-maintenance brick siding. The kitchen includes a newer refrigerator, stove, and dishwasher.

Slope-side living at Jiminy Peak with proven income potential! Located just steps from the ski slopes and very close to the year-round heated pool, this beautifully positioned one-bedroom suite offers the perfect Berkshire getaway and an exceptional short-term rental opportunity.Currently operated as a successful Airbnb/short-term rental, the unit generated approximately $17,162 in net income after expenses in 2025 and over $20,000 in 2024, making this an attractive option for both lifestyle buyers and investors seeking a turnkey four-season property.Unit 521 combines the charm of a cozy mountain retreat with the convenience of full resort amenities, including an outdoor heated pool, fitness center, sauna/steam room, on-site dining, front desk services, and tennis courts

Located along the Dalton Ave corridor in Pittsfield, this home offers a 4-bedroom layout with recent updates and a partially-finished basement. Situated on a corner lot, the home offers extra yard space and a new deck for seasonal use. Interior improvements include refinished hardwood floors, fresh paint throughout, and an updated bathroom, creating a move-in ready feel.A traditional ranch style home, the main level features the majority of the living space. It includes a formal dining room attached to the kitchen and a spacious living room in the front. It also includes one full bathroom and three bedrooms with hardwood floors and generous closet space. The finished basement adds valuable bonus space with a bedroom, laundry room, and entertaining area suitable for a variety of uses.

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

Sleek and sophisticated, this stunning downtown condominium in the hip arts community of North Adams is but a stone's throw from the incomparable Massachusetts Museum of Contemporary Art as well as a host of other galleries,eateries and shops. Recently thoroughly renovated with a refined richness of detail and careful preservation of some original features of the 1873 landmark building, it is distinguished by high ceilings,spacious rooms,and grand windows with sweeping mountain and cityscape views.Discerning attention has been bestowed upon all aspects of design,and especially lighting,from the elegant lines and shapes of the fixtures to the complete adjustability of all recessed lamps in color,direction and intensity.The result ia a splendid oasis of calm and comfort, a feast for the eyes

Beautifully maintained 2 bedroom, 2 bath condo, both bedrooms/ baths on main level with covered deck & beautiful views, finished lower level w/ laundry offers whole other level of space for office, hobbies, etc. Enjoy the clubhouse (gym, pool table, hot tub, sauna, kitchen/entertainment rm, local art hangings) out door POOL, TENNIS COURTS, walking TRAILS, community GARDENS, kayak storage, fenced dog PARK, EV charging stations. Perfect Berkshire location, CLOSE to all cultural destinations, Tanglewood, restaurants, shops, outdoor recreation! FIRST FLOOR condos like this are hard to find. RH is undergoing attractive and energy upgrades on the siding. This unit is priced to reflect the current siding assessment of @ $141.04/month for 5 years. Monthly condo fee is $703. Buyer to verify

Recently renovated embankment ranch-style home tucked into a cul-de-sac neighborhood in Great Barrington and bordering Monument Mountain Reservation. Interior updates include new hardwood flooring, ceramic tile, fresh interior paint, new kitchen cabinetry, granite countertops, stainless steel appliances, and added insulation through the Mass Save program for improved energy efficiency. The one-level layout offers 3 bedrooms, 2 full bathrooms, an open kitchen/dining area, and natural light throughout the main living spaces. A primary bedroom includes an en-suite and generous closet space, while additional bedrooms also feature large closets. A rear deck overlooks the wooded setting and provides direct access to the surrounding outdoor landscape and hiking.