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.

Just over the hill from Tanglewood, down a quiet country road, this year-round Richmond retreat blends privacy, rustic character, and expert craftsmanship. The heart of the home is the vaulted great room, where exposed beams, a loft balcony, and a wood stove create a warm gathering space that flows seamlessly into a beautifully crafted three-season porch with interchangeable glass and screen panels overlooking the woodland. Thoughtfully designed to preserve the home's original rustic charm, the spacious primary suite is a private retreat featuring vaulted ceilings, a sitting area with a gas stove, an ensuite bath with a soaking tub, and laundry. Wraparound decks further extend the living space outdoors, embracing the natural landscape. The walk-out lower level provides excellent storage

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

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

Perched high above a serene, bucolic country setting, this warm and inviting three-level home perfectly blends private seclusion with everyday convenience. Offering spacious open-plan living, the home features a dramatic, floor-to-ceiling stone fireplace in the great room that anchors the space with timeless rustic elegance.The seamless flow connects the living area, dining space, and kitchen--ideal for both quiet evenings and effortless entertaining. Just off the first-floor primary suite, a dedicated hot tub room offers a private year-round retreat. Upstairs, an open office loft looks down over the great room, accompanied by two guest bedrooms and a full bath. The walk-out lower level expands your living space with a large family room and laundry room,complemented by abundant storage

Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and serenity. Second level has ample space with three guest bedrooms, two full baths and loft/office space open to the great room. The lower level walkout family room is gracious in size and has direct access to your private stone patio. Additionally, you have the fifth bedroom, full bath, laundry room and bonus storage room. Enjoy the association pool, Bousquet Mountain next door and all of the

Light-filled contemporary cape built in 2020, this Stockbridge home features an open floor plan anchored by a great room with a gourmet kitchen, dining area & living room. Two spacious first-floor bedrooms share a full bath, while the expansive second-floor primary suite offers a luxurious spa bathroom & a balcony overlooking the living area. The four-season sunroom (heated & cooled for year-round use) opens to the level backyard. Lovely front entrance with Bluestone steps into an ample mudroom. Enjoy year-round comfort with zone-controlled mini-splits. Close to vibrant Great Barrington, Stockbridge & Lenox. A quick drive to Tanglewood, cultural venues, & abundant outdoor recreation including hiking & lakes, this modern retreat blends style, comfort, and an exceptional Berkshires location.

Tucked away on 3.24 private wooded acres, this one-of-a-kind Contemporary offers 3,744 sq. ft. of living space across three finished levels. Soaring ceilings, exposed timber beams, hardwood floors, and a dramatic center chimney create a warm yet impressive setting. The open floor plan is anchored by multiple wood-burning fireplaces, a pellet stove, and abundant natural light. Offering a total of five bedrooms and 3.5 baths, including a private in-law suite above the oversized attached two-car garage, this home provides exceptional flexibility for guests or extended living. Enjoy an owned 9.52 kW solar system, spacious decks, beautifully maintained grounds, and the privacy of a true Berkshire retreat just a short drive from everything the Berkshires and Northampton have to offer.

Beautiful end-unit property featuring soaring ceilings and serene wooded views. The home offers open common spaces with excellent natural light, a screened porch, and a first-floor primary en suite. The second level includes two guest bedrooms, a full bath, and a loft overlooking the great room. Additionally, the lower-level walkout provides significant potential to be finished for extra living space. Residents can also enjoy the association's pool. This property is perfectly situated near Bousquet Mountain to enjoy the many cultural attractions here in the Berkshires.

Loft 309 at Greylock WORKS is a distinctive north-facing 1BR | 1.5BA Berkshires residence with a generously scaled study, offering approximately 1,340 SF of thoughtfully designed living space. Set on the third floor of the region's most celebrated mill conversion, this home is defined by its warm wood ceilings, varied ceiling heights, and refined blend of historic character and modern finishes. The open living, dining, and kitchen area creates an inviting central gathering space, grounded by restored materials and an easy, functional flow for everyday living and entertaining. Energy Star appliances, Kohler and Grohe fixtures, energy-efficient windows, and an in-unit washer and dryer support both comfort and sustainability.

Welcome to this large expansive dwelling that features great privacy! Enjoy outdoor cooking and refreshments on the enlarged deck for these hot summer days. Also featuring a separate personal deck off the Primary bedroom. This great home boasts an oversized living room with a Grand fireplace place that will impress any viewer. An interior balcony from the sizable Primary Bedroom overlooks the oversized living room. A large kitchen leading to your dining room that opens up to the back deck. Updated bathrooms with amazing tilework will be found throughout the home. An oversized garage to store your personal vehicle or off-road vehicles of your choice. The lower level including a bonus room that is currently being used a game room completes the interior. It's a Perfect opportunity to finish

This unique and chic first floor Carriage Barn unit in the desirable White Pines Association is a must see if you are considering condominium life. Thoughtfully proportioned open common spaces including a gracious great room with fireplace overlooking the sun room, dining area open to the kitchen with bar, ample cabinets and half bath. The lower level offers a two story sunroom w/wall of glass & skylights that wash the unit with natural light and bring nature to the interior w/direct access to a private deck, primary bedroom w/en suite full bath, guest bedroom,en suite & laundry room. The Association boasts beautiful grounds, indoor pool, hot tub, exercise room, tennis courts, hjiking trails and private beach frontage on the Stockbridge Bowl for swimming, kayaking or anchor your

Immaculate and well-maintained contemporary home in an exceptionally convenient location set on 5+ wooded acres. Designed for easy living and low maintenance, this home offers an open floor plan with high ceilings, wood floors, and a beautiful fieldstone fireplace anchoring the main living space. The kitchen opens to another living area creating a comfortable flow for everyday living and entertaining. Enjoy the lovely screened porch and outdoor deck overlooking the natural setting. Three bedrooms and 3.5 baths, including guest quarters or apartment space for added flexibility. Large two-car garage. It is in a very private setting, but is also a short distance (walking distance) to the elementary and secondary schools. Easy transition for a first floor primary bedroom.

Own Pittsfield History in this distinctive solidly built Georgian-style brick estate set proudly atop a hill in this coveted enclave of stately residences. Live on historic Crofut St. near the esteemed Pittsfield Country Club, Up Street Cultural Art District and ideally minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved by this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring Little Red Guest House with 3 bedrooms, 2 bath, first floor in-law suite and 2 car garage to host family, friends. Enjoy carefree ownership central to all that is Berkshire!

New Construction!! Three bedroom contemporary chalet to be built on a 17 acre portion of the 1800's E.B. Palmer farm. Two owners in a construction company partnership bought the property 20 years ago with the idea that each would build a personal home on the acreage. Life changed. Now semi retired, they are contracting with a builder of quality manufactured homes to build modern, efficient homes on the property. Marcy Road is a lightly populated, town maintained road 1.5 miles from Route 8. Easily accessed from NY, CT & the Mass Pike and convenient to many Berkshire attractions. The massive 2.5 acre Otis Town Beach on 300+ acre Big Pond is less than 5 miles away. The lot is forested with frontage on both sides of Dimmock Brook. Perc tests are schedule for as soon as conditions permit. Th

One of the Southern Berkshires' best-kept secrets! This private, family-friendly, four-season community is located near the shores of pristine 175-acre Noyes Pond, a non-combustion-motor lake. This large log cabin sits on 2 wooded acres with no neighbors, offering exceptional privacy. Enjoy evenings on the outdoor patio around the fire pit, making s'mores and creating memories with family and friends. The cabin is being sold with the recently purchased furnishings--everything stays, making this a truly turnkey retreat. The home features 4 bedrooms, 3 full baths, a 4-car garage, and an inviting open floor plan with beautiful vaulted, beamed ceilings. The spacious primary suite includes a walk-in closet. A large recreation room with a convenient back staircase provides additional space for

Modern elegance meets turnkey peace of mind in this fully reimagined Sheffield retreat. Set on 2.3 level acres, this 3BR, 3.5BA sanctuary spans 2,748 square feet across three finished levels. The sun-drenched main floor features wide-plank white oak floors, a gas fireplace, a large half bath, a chef's kitchen with stainless appliances, white quartz counters, and seamless access to a wrap-around deck. Upstairs, a treehouse-like loft adds charm, while the primary suite delivers a spa-like experience. The three suites were designed for intimacy and privacy. The walk-out lower level houses a guest suite and fantastic game room. Renovated top-to-bottom with no expense spared, central A/C, and new mechanicals--just bring your suitcase. 15 mins to Guido's and 45 mins to the Wassaic NYC train.

The mid-century retreat you've been waiting for. This classic home sits on over 4 private acres, delivering the ultimate Berkshire lifestyle with a bright, open floor plan and two cozy fireplaces. With 4 bedrooms, 3 baths, a large office, and a sun room looking overlooking your oasis, the layout offers perfect flexibility for guests or remote work. Outside, your private resort features a heated swimming pool and a dedicated tennis or pickle ball court tucked at the end of a quiet road for unmatched seclusion. Modern upgrades including a large solar array and a new heating system drastically reduce utility costs. Experience total privacy while staying minutes from everything that makes Great Barrington a premier Berkshire destination.

Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming gazebo and a generous deck, perfect for hosting gatherings or relaxing in your own outdoor oasis.The oversized garage provides ample storage and includes a versatile space above, ready for your expansion ideas. With rough plumbing and electrical already in place, customizing this area is effortless. Located 2 min from Monument Mountain Reservation and 6 min to Main Street.

Perched on Mount Hunger is this lovely, private, contemporary four-bedroom, three-bath home located near Lake Garfield, of which there are winter views. The current owners added a huge, beautiful living/dining room with a fieldstone fireplace, cathedral ceiling and huge windows. The renovated kitchen has granite counters with a Viking cooktop and Bosch double wall ovens. A first floor primary suite is complimented by a den and a three-season porch. The second floor holds two guest bedrooms and a guest bath, while the lower walk-out level has a fourth bedroom, a family room, laundry and utility room and a storage room with built-in shelving. Located well off the road with air conditioning, an outdoor shower and fiber internet. A true Berkshire country home with the best town beach nearby.