A DRILLED WELL, A COMPLETE 6 BEDROOM SEPTIC SYSTEM, A HORSE BARN AND A SHED COMES WITH THIS FABULOUS 42 PLUS ACRE PARCEL. BEAUTIFUL STONE WALLS SURROUND THE BUILDING SITE AND ACROSS FROM PROTECTED LAND

Built in 2021, this contemporary home offers 5,670 sq ft of living space on 2+ acres, just 5 minutes from Great Barrington. Enjoy mountain views and stunning sunsets from the open-concept first floor featuring vaulted ceilings, a fireplace, chef's kitchen with large island, coffee bar, and ample storage, all flowing into spacious dining and living areas. A screened porch extends living space for three seasons. The main level includes a mudroom with laundry, oversized 3-car garage, two offices, and powder room. Upstairs: two guest suites and a primary suite with fireplace and large bath. The finished lower level adds 1,900 sq ft with game, gym, media rooms, guest bedroom and full bath. Central air and fiber internet available. Can be purchased fully furnished outside of list price.

Welcome to Merritt Farm - The original home built in 1780 oozes with charm. Front of the house faces south with a large heated sun porch flanking the west side overlooking the pool and tennis court. The main floor rambles with a front parlour, a keeping room off the kitchen with back stair, formal dining and office. In 2008 a large studio addition was added with a first floor primary, full basement and heating system supplying the kitchen and boot room with radiant heat as well as the studio. Second floor has two additional bedrooms, one with a large deck over the sunporch and a generous hall bath. Over 35 acres with mature landscaping, gunite pool and tennis court nicely tucked away this property is set up to be the modern homestead.

Blending historic craftsmanship with modern comfort and versatility, this exceptional Berkshire estate presents a truly unique opportunity. The stately home is in remarkable condition and beautifully maintained. Comfortable floor plan with a grand foyer with sweeping staircase, expansive kitchen with butler's pantry, formal living spaces, sun porch, and multiple covered porches. The luxurious primary suite offers a sitting room, balcony, sun porch, and spa-like bath. Three additional bedrooms, two baths and two offices complete the second floor. A finished third floor provides flexible additional space. Excellent mechanicals. Attached spacious garage that can park 4 cars in double tandem. Surrounded by mature grounds on 5.7 acres and within walking distance of village of Dalton . . . .

Magical Egremont setting. Step into timeless charm with the comfort and craftsmanship of a beautifully renovated 1860 home abutting Karner Brook. The brook flows just beyond the sitting room and deck overlooking the beautiful landscaping and bridge that leads to the garden and brand-new outbuilding. Offering three/four bedrooms, three bathrooms, and over 3,000 square feet, this distinctive property blends historic character with thoughtful modern upgrades, including cherry cabinetry, granite countertops, a Sub-Zero refrigerator, Viking six-burner range and hood, and two dishwashers. Wide-plank pine floors, beautiful woodworking, and a fireplace create inviting spaces throughout.

A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent century-old oak tree, and follow the gentle brook that borders the property. This remarkable landscape offers a rare combination of privacy, natural beauty, and accessibility. Create an incomparable estate overlooking the mountains, or take advantage of the property's three ready-to-build lots to establish a family compound nestled among meadows and woodland. Whether envisioned as a private retreat,

Your private Berkshire retreat! Sweeping views of Squaw Peak, surrounding mountains, 42 beautiful sub-dividable acres with trails, seasonal brook, room for pool, tennis court, family compound. Warm, welcoming 4BR, 4.5 bath, home with room for family, friends, gathering or quiet escapes. Sun-filled fireplaced LR with picture window, cozy window seat framing the view; elegant formal DR with window wall and fireplace. Spacious chef's kitchen with island, dining area, TV area, comfy wood stove, leading to the large screened porch and expansive deck--perfect for morning coffee, summer dinners or simply relaxing. 3 main-level BRs include ensuite primary. Above-grade LL offers office, 4th BR, bath, inviting fireplaced family room. 2-car garage. 1 mile to downtown Great Barrington.

Located in a ''hidden'' neighborhood behind a stonewall entrance, this newly built home offers tranquil living just 5 minutes from the heart of Great Barrington. The spacious farmhouse front porch is the perfect spot to enjoy quiet mornings or gather in evenings with family and friends. Light-filled and open, the main level features an elegant living and dining area framed by French doors, a gas fireplace, and a chef's kitchen designed for effortless entertaining. Also on the 1st floor, a guest bedroom suite enjoys a private bath with shower and soaking tub. On the 2nd floor the generous primary suite offers dual walk-in closets as well as an luxuriously oversized shower and soaking tub.

Imagine slow mornings surrounded by nature, cozy evenings beside a dramatic stone fireplace, and 15+ acres of Berkshires countryside to call your own. This distinctive Sheffield post-and-beam home offers soaring timber beams, wood floors crafted from a tree harvested on the property, and a substantial 3 bay barn/workshop complete with two additional lean-tos perfect for ATVs, tractors, a prized vehicle collection , art studio, gym, the sky's the limit. The kitchen and baths invite your personal vision, offering over time, the opportunity to blend modern comforts with its inherent timeless character. Discover a private country retreat with room to dream, create, and make it yours at 525 Rote Hill.

The Simeon Sage House. A lovely, move-in-ready Historic Colonial on the Seekonk Brook with a separate guest cottage, set on 2+ beautifully maintained acres just minutes from downtown Great Barrington. Dating to 1773, the home was thoughtfully renovated and expanded in 2006, seamlessly blending its original character--wide-plank wood floors, original fireplace and exposed beams--with modern comforts and thoughtful finishes. The main level offers a spacious kitchen, open living room and dining area, inviting great room with fireplace and access to the deck, a laundry room, and full bath. A stunning primary suite addition overlooks the grounds and opens directly to the deck, creating a private retreat. Upstairs are two additional bedrooms with a shared bath, while a

Looking for a Berkshire getaway that can help pay for itself? This unique 6-unit property in Lee offers the rare opportunity to enjoy a spacious 4BR/2BA home of your own while generating income from 5 additional apartments. Full of character, the property retains many of its beautiful original features with significant updates, including renovations to 5 of the 6 units, a newer roof, updated electrical and newer heating systems. Set on a spacious property with ample parking, public water and sewer, and separate utilities, it offers tremendous flexibility for seasonal, short-term or year-round rentals. Centrally located near the Mass Pike, downtown Lee, Outlets, Tanglewood and all that the Berkshires have to offer. An ideal combination of Berkshire lifestyle, character and income potential!

A rare opportunity on Lake Garfield, this mid-century A-frame and two-story barn are being offered for the first time since the home was built in 1965. Renovated over the years, the home features a dramatic cathedral-ceilinged great room with a wood-burning fireplace, a wonderful kitchen with butcher-block countertops, three bedrooms, two full baths, and a comfortable TV room in the second-floor loft. The property comprises two separate parcels: one with the house and barn, and the other providing direct waterfront access. Long considered one of the Berkshires' most desirable lakes, Lake Garfield has been the setting for generations of cherished summer memories. Now, a new owner has the opportunity to create a distinctive lakeside compound and begin a tradition of their own.

Cross the charming historic-style covered bridge and enter a world of privacy, nature, and endless possibilities. This remarkable 94-acre sportsman's estate offers river frontage on the Farmington River, expansive woods, trails, and room to roam. At the heart of it all is a spacious split-level home with 3 bedrooms and 2.5 baths, featuring fresh paint, new flooring, and a new roof. A 5-bay barn/garage provides incredible space for vehicles, equipment, hobbies, and toys. A separate mobile home offers flexible additional space for a studio, guest quarters, office, or creative retreat. Whether you're seeking a private Berkshire escape, outdoor adventure, or simply a place where the woods are truly your own, 132 North Main Road is a rare opportunity to own your very own Hundred Acre Wood!

Privately sited across 10.37 park-like acres, this fully updated residence stands as an elevated countryside sanctuary, positioned moments from historic Rhinebeck Village and ten minutes from the Taconic State Parkway. The interiors express a refined architectural warmth, anchored on the main level by a primary suite with full bath, a striking floor-to-ceiling stone fireplace with an integrated wood stove, and a thoughtfully updated chef's kitchen designed around a generous central island. The upper level offers private guest quarters featuring two spacious bedrooms, a full bath, and a dedicated laundry room, while an attached two-car garage affords subtle everyday convenience.

Properties of this magnitude and character are becoming a true rarity in today's market. Brookmede Farm, isn't just a listing; it is a magnificent blank canvas of 22 beautiful scenic acres, defined by sweeping mountain views and a profound sense of quiet serenity. From the moment you arrive, the silence and the scale of the landscape invite you to imagine the unlimited possibilities. Whether you envision a world-class equestrian estate, a sustainable organic farm with cows and chickens, or a sophisticated multi-structure family compound, this land provides the space and the soul to make it a reality. Standing as a centerpiece to this vision is a towering, three-story Timber Frame barn. With its incredible volume and structural presence, it offers a

Four-bedroom homes are a rarity at Coldbrooke, where most residences offer three. This one combines that hard-to-find layout and one of the community's more generous floor plans with a location beside the Miraval Berkshires resort and the historic Wyndhurst estate, putting world-class spa, dining, and golf just steps from the door. Inside, vaulted ceilings and an open layout fill the home with light. A thoughtfully updated kitchen anchors the main level, opening to a spacious great room with adjoining dining and living areas built for gathering. Out back, a screened porch and deck overlook the golf course, an easy setting for summer cookouts or a drink after a round.

A once-in-a-lifetime opportunity to build your dream home on a large waterfront parcel in Lenox. This spectacular 14-acre property offers privacy, tranquility, and direct frontage on beautiful Laurel Lake while remaining just minutes from downtown Lenox, Tanglewood, shopping, dining, and all the Berkshires has to offer. Enter through the stone and metal electric gate, cross the stone bridge, and arrive at a cleared, manicured homesite ready for your custom estate or compound. A scenic boardwalk winds to your private dock and lakeside sitting area. Truly a rare Berkshire offering combining natural beauty, convenience, and waterfront living.

Set on a desirable tree-lined dead-end street in the heart of Lenox, this beautifully restored 1937 Cape blends timeless character with exceptional craftsmanship. Featured in Berkshire Magazine, the 3,740 sq. ft. home offers original heart pine floors, a wood-burning fireplace, and extensive updates including new plumbing, electrical, Pella windows, roof, and central AC. The three-level layout features 3 bedrooms, 4 full baths, two upper-level suites, and a finished lower level with a guest suite, office, and workshop. French doors open to a wraparound veranda overlooking Goshen stone terraces, fruit trees, and a fire pit. Walk to downtown Lenox with convenient sidewalk access, while Tanglewood is just minutes away.

Entertainer's Delight! Tucked away in one of Sandisfield's most scenic settings, this quality-built log home offers over 4,600 sq.ft. of finished living space, plus an additional 2,000+ sq.ft. in the walkout basement ready for living, recreation, or storage. Crafted with exceptional materials, the home features soaring ceilings, expansive gathering spaces, and a warm, inviting atmosphere perfect for entertaining or everyday living. Multiple decks provide an ideal setting to dine, unwind, and enjoy the peaceful natural surroundings. Experience the perfect balance of privacy and convenience, just 20 minutes to Guido's and downtown Great Barrington, 30 minutes to Lenox and Tanglewood, and 15 minutes to Ski Butternut. A true Berkshire gem for year-round living, weekend retreat, or investment!

Experience upscale, maintenance-free living in desirable Devon Meadows, ideally located near Lenox and Stockbridge and just 5 minutes from Tanglewood and the many cultural and outdoor attractions of the Berkshires. This spacious luxury condominium features an open floor plan perfect for everyday living and entertaining. The first floor offers a primary bedroom suite, laundry, and a versatile fifth bedroom ideal for an office or den. Upstairs are three spacious bedrooms, two full baths, and a comfortable family room. Enjoy the privacy of a peaceful country setting with the convenience of being minutes from dining, recreation, shopping, and all that the Berkshires has to offer.