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.

A unique farming opportunity on a self-sufficient 51-acre parcel, highlighted by an 1802 antique Colonial exuding historical charm. A thoughtfully conserved agrarian sanctuary with organic soil, a fruit orchard, maple sugar house, trails, gated pastures, and a running brook. The large barn and mature gardens are framed by stone walls and outbuildings. Bright rooms with wood floors, antique beams, 4 fireplaces with generous common spaces ideal for family or community living. Sustainable energy solutions: grid-tie solar, photovoltaic hot water, a hydronic wood boiler and on-demand hot water, ensure economic fuel usage. A soulful property reflecting American heritage offering privacy & tranquility. A unique opportunity for farm-to-table living, historical immersion and rural sustainability.

Discover this enchanting 1900s Town Colonial, where historic charm meets modern sophistication. Nestled in a tranquil neighborhood, this home offers four spacious bedrooms, two updated full baths, and a stunning chef's kitchen, blending comfort with style. From the moment you enter through the newly renovated mudroom, you'll appreciate the original wood floors and built-in shelving that preserve the home's historic character. The first floor features a convenient en suite bedroom. The heart of the home, the chef's kitchen/dining room is a culinary delight equipped with top-of-the-line appliances and ample counter space. Partially renovated barn. Nice yard.

Your waterfront lifestyle begins at this Hayes Pond sanctuary. From sunrise paddles to sunsets savored from the deck, this home is your private four-season escape in the Berkshires. The modern, open interior is designed to celebrate the water, with soaring cathedral ceilings and a wall of windows that frames the stunning lake view. A cozy wood stove, bright sunroom, and a large deck provide perfect spaces for relaxing or entertaining. This 4-bedroom retreat includes a primary suite featuring a calming soaking tub. Your private, grassy shoreline is your personal gateway to the lake--perfect for launching kayaks, fishing, swimming, or the occasional bonfire. This is the ultimate waterfront escape, where every detail is focused on a life lived by the water.

Welcome to 221 Bailey Road in Lanesboro, MA., an exquisite ranch-style home offering approximately 4,200 sqft of luxurious living space. Nestled on 87 acres atop a mountain, this property provides unparalleled privacy and breathtaking views that enhance its serene atmosphere. The open-concept living area is perfect for entertaining, featuring abundant natural light and seamless flow between spaces. Energy efficiency is a hallmark of this home, ensuring comfort year-round while minimizing utility costs. Ample room for family and guests, this stunning residence combines modern amenities with the tranquility of nature. Some of the amenities this home offers a three car garage, heated in ground pool, owned solar and a cozy wood stove for those chilly Berkshire nights.

Discover a stunning oasis in this custom-built contemporary home, ideally situated in a picturesque and private setting. Enjoy tranquil views of a serene pond, beautiful gardens, and flourishing fruit trees, all while basking in an abundance of natural light. This home is a dream for those who love to entertain. The spacious dining room and inviting living room, complete with a cozy fireplace, provide the ideal backdrop for gatherings, complemented by three spacious decks that extend your living space outdoors. Culinary enthusiasts will delight in the oversized cook's kitchen, featuring charming terra cotta floors, premium appliances, a generous center island, and ample dining space. Retreat to the luxurious first-floor primary bedroom suite, which offers a large walk-in closet,

Cable Mills, industrial mill buildings restored into beautiful homes with 12ft to 16ft tall ceilings, massive windows, and exposed brick and beam, steel and timber throughout, stainless appliances, granite countertops, gas ranges, generous closets and in home laundry. Cable Mills offers stunning views of the 'Purple Mountains' and the Green River. Homes are one, two or three bedrooms in single level flats, lofts and townhome styles totaling 61 residences. Outdoor spaces including the Outdoor Living Room with a fire pit, grills and seating along the river walk. The main building offers a community lounge, fitness center, interior bike storage, package delivery room, dog wash and on-site professional management. #CableMills #WilliamstownMA #BerkshiresLiving #LoftStyleCondo

A Nature-Lover's Haven Awaits Set on an expansive 94-acre stretch bordering the tranquil Tolland State Forest, this distinctive property combines unmatched privacy with exceptional natural charm. Envision life along the serene Farmington River, with hundreds of feet of stunning river frontage and your very own storybook-style covered bridge--an extraordinary hallmark of this countryside escape.Highlights Include:Vast Acreage: 94 acres of secluded, wooded beautyRiverfront Magic: Extensive frontage on the Farmington RiverSignature Feature: Historic-style covered bridge adds character and charm

Beautifully renovated New England Farmhouse with thoughtful modern updates! The home retains original character with wood floors, some exposed timber framing, and a cozy fireplace. Chef's kitchen with high end appliances for serious cooking and easy entertaining. Three comfortable bedrooms, one a primary ensuite, with two additional flex spaces that work for offices, guests , den or creative studios. The screened porch is a three season favorite! EV charger and efficient systems. Set in a prime Berkshire location close to skiing, and minutes to Main Streets of Great Barrington & Stockbridge. Authentic, soulful and elevated, whether full-time or as a vacation home..

Prepare to be wowed when you visit this fully furnished luxury condo at Stockbridge Terrace! Move-in ready and lightly lived in, this one-owner home features many custom finishes. Seeking one-level living? This condo delivers. Entertain in style with open floor plan. The living/great room's centerpiece is the stone fireplace, oversized windows and cherry floors. Enjoy the formal dining room or savor summer dining on the spacious screened porch. Primary suite on the first floor includes a jetted tub, oversized shower. along with a custom outfitted walk-in closet. On the upper level you'll find two additional bedrooms each with ensuite baths, an office, and spacious family/gathering space. Bonus is a finished walk-out lower-level w bedroom/bath, game room with kitchenette. Don't wait!

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.

Updated and spacious condo just a short distance from Main Street Stockbridge, downtown Lenox, and all the Berkshires has to offer! Premier Unit at Stockbridge Terrace: Enjoy peaceful living on a private cul-de-sac with a limited number of units. The main level living setup is perfect for the primary resident, featuring a large primary bedroom with an en-suite bath and walk-in closet, an open-concept kitchen that has been recently updated complete with top-of-the-line appliances and all new high end cabinetry. The Great Room boasts cathedral ceilings bringing an abundance of natural light and a soaring gas fireplace for added ambiance. Enjoy your private backyard views from the 4-season sun porch equipped with both heat and A/C for year-round comfort.

Discover comfortable & gracious living in this impeccably renovated home in Lenox. 4 BRs & 4 BAs approx. 4,000 sq ft of open, modern design. The entire home is filled w/sunlight & gleaming new red oak flooring & a sleek chef's kitchen outfitted with new Bosch appliances, quartz countertops & significant storage. Functional yet luxurious details throughout- from laundry on 2nd level to mini-split systems, fireplace & a sunroom that promises cozy comfort in all season. Step outside into your private natural oasis: enjoy gatherings w/ woodland views around the fire pit, on deck or patio. Newly finished lower level includes a living, dining & media room equipped with kitchenette & full bthrm. Set in one of Lenox's most desirable neighborhoods, this home provides privacy and convenience.

This fine, four-bedroom, two bath colonial saltbox home just south of the village of Stockbridge is a handmade work of art and an important slice of Stockbridge history. It was constructed on or about 1750. There are patinaed wide board floors throughout as well as five fireplaces (three wood and two gas) and much original hardware. The home is surrounded by perennial gardens and a formal, boxwood garden, all of which have been meticulously maintained. There are two stone patios which look out over four acres of pasture to the west. This home is fueled by gas heat and is serviced by town water and sewer. Perhaps the famous Reverend, Johnathan Edwards and Chief Kondapot of the Stockbridge-Munsee Indians met in the front parlor a time or two.

Designed in 1929 by noted architect Henry Seaver (Berkshire Museum, Lenox Town Hall), this distinguished Georgian Colonial was once the centerpiece of Pittsfield's social scene. The home preserves exquisite 18th-century details - mantels, wainscoting, and finely crafted woodwork salvaged from two of the city's earliest residences, making it a living piece of Berkshire history. Set back on 2.5 private acres along prestigious Crofut Street, the estate offers 5 bedrooms and 5 baths, including twin primary suites ideal for hosting friends and family year-round. Gracious living and dining rooms, a peaceful sunroom, a cozy study, and a large eat-in kitchen with Viking range and butler's pantry combine period elegance with modern comfort. This turn-key estate is offered fully furnished and

THEY DON'T BUILD HOUSES LIKE THIS ANYMORE.They don't build love at first sight anymore, either. But Sky Hill Farm - a genuine 1798 Federal colonial in Tyringham Valley - has been creating that exact feeling for over two centuries.In 1912, Adele LeBourgeois Chapin wrote about first arriving here at dusk, walking through high grass to the old front door with its worn stone steps and feeling the homely welcome as she went in. ''This old house was beautiful,'' she wrote, ''the rooms perfectly proportioned, the mantlepieces charming old Colonial ones...I felt as if I was at home at last.''Views of Tyringham's Shaker Fields65+ acres3,443 sq ft4 bedrooms2 1/2 baths2 barnsPasture & Hay fieldsNew Roof on Main HouseNew SepticUpgrades & Repairsclick MORE -or reach out

This quintessential turn of the century antique home, built in 1909, is in immaculate condition. Set just outside the charming village abutting desirable Pine Crest Hill Rd, the property provides privacy with beautiful gardens and landscaping and stunning views of pasture and mountains, 3 miles to downtown Great Barrington, in low-tax Egremont. The main residence features 4 spacious bedrooms, 3.5 baths, two cozy fireplaces, tall ceilings, and light, bright, airy spaces that create a welcoming atmosphere. A separate guest house with two bedrooms, currently in need of some TLC, adds to the versatility of the estate. The grounds span 11 gorgeous, sub-dividable acres, presenting future possibilities for a family compound. Conveniently located near Berkshires attractions.

This stunning 6-family home sits on 1.5 acres, a large lot that goes from Forest St to Silver St, a convenient location with easy access to the Mass Pike and just a couple minutes away from the Lee Outlets. This multi-family consists of 3 two-bedroom units, 2 one-bedroom units, and a 4 bedroom 2 bath unit. The large unit offers a welcoming front porch, living room, eat-in kitchen, full bath and primary bedroom on the 1st floor, and 3 bedrooms and full bath upstairs. This expansive apartment would make a great owner's unit, or rent it out for additional income! Some of the improvements done in the last few years include new kitchens and bathrooms in 5 apartments, new roof, 2 new high efficiency heat/hot water systems and mini-splits. All units have separate heat, hot water & electricity.

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.

Welcome to Cannondale Compound. Set on 20 private acres with far-reaching mountain views, this 7,300-square-foot architectural retreat is ideally suited for large gatherings. Designed with soaring modernist lines and exceptional craftsmanship, the home offers multiple living and dining areas, seven bedrooms across two connected wings, expansive porches and balconies, and both indoor and outdoor pools. Outdoor highlights include a hot tub, pool house with bathroom, pavilion, garden, and a fully enclosed treehouse for summer overnights, along with deeded Queechy Lake rights for swimming and kayaking.The main wing of the home features a dramatic triple-height great room with a fieldstone fireplace, flanked by a wraparound deck.