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$2,698,000
5 Beds 5 Baths 73551597 MLS
Some homes are purchased. Others become part of a family's legacy. Welcome to 109 Under Mountain Road. There is something unmistakably special about a Berkshire summer- evening stroll to Tanglewood, morning coffee overlooking protected meadows, or relaxing on the patio as the music of the Boston Symphony Orchestra drifts softly through the evening air. Bathed in extraordinary natural light, this architect-designed home embraces its breathtaking setting with soaring walls of glass, vaulted ceilings, exposed beams, skylights, and exquisite gardens. Thoughtfully designed for gracious entertaining and comfortable everyday living, the spacious first-floor primary suite allows you to enjoy the home with ease for years to come, while family and friends gather in beautifully appointed guest rooms.

109 Under Mountain Rd, Lenox

$660,000
5 Beds 3 Baths 73522628 MLS
Tucked away on a serene & private lot just minutes from the sparkling waters of Otis Reservoir, this stunningly renovated 5-bedroom, 3-bath Colonial offers the perfect blend of luxury, comfort, and natural beauty. Designed for both elegant entertaining and everyday living, the heart of the home is the spectacular chef’s kitchen featuring quartz countertops, abundant cabinetry, and refined finishes throughout. The thoughtfully designed 1st flr offers a formal living room, sophisticated dining area, two spacious bedrooms, and a beautifully updated full bath — ideal for guests or flexible living arrangements. Upstairs, retreat to the luxurious primary suite complete with a private ensuite bath, along with two additional generously sized bedrooms and a third full bath. Surrounded by peaceful nature views, trails and exceptional privacy, this remarkable property is a rare opportunity to enjoy upscale living in a tranquil setting to enjoy all the beauty the Berkshires have to offer.

23 Old Blandford Road, Otis

$275,000
5 Beds 2 Baths 73520450 MLS
Step into timeless elegance with this charming Victorian home, where classic character meets modern comfort. Rich in original detail, the home showcases arched doorways, gleaming hardwood floors, French doors, and beautifully crafted fireplace mantels that echo a bygone era. The updated kitchen and baths bring today's conveniences into the space, blending seamlessly with the home's historic appeal. Offering 4 bedrooms and 2 full baths, there's room for flexible living, while a cozy wood stove adds warmth and charm. Many replacement windows enhance efficiency, and outside, a small, manageable yard makes upkeep easy. The standout feature? A sprawling wraparound porch--perfect for relaxing, entertaining, and enjoying peaceful days and evenings. (additional photos coming soon)

17 Bobs Hl, Adams

$3,998,000
5 Beds 6 Baths 24142076 MLS
WHERE THE WORLD FALLS AWAY 227 acres. 227 years. At East Hill Road's summit, East Hill Farm is a fully realized estate where infrastructure, land, and possibility are complete and in place. The 1798 Thomas Shepard House-museum-quality restoration featuring 5 bedrooms, 5.5 baths, 5 fireplaces, original King's board floors, hand-blown glass windows-awaits your vision for kitchens and baths. Modern additions: radiant heat, elevator, sun-filled library, luminous sunroom overlooking formal gardens and 4-acre spring-fed pond. The 227 acres aren't just land-they're composition. Meadow unfolding to pond positioned where morning & evening light catch it. Mature forest giving way to unbroken views. Trails looping you gently home by blue hour. Stone walls, pool, tennis court, greenhouse. Magnificent 3,550sf hand-hewn barn moved here. Northern land borders State Forest; southern abuts conservation land-permanent privacy. Guest house (6,668sf): 4 residences replete with possibilities-multigenerational living, art studios, writing spaces, media rooms, yoga, creative sanctuary. Cathedral ceilings, fireplaces, soaring light. The quiet money cannot buy: depth of silence settling at dusk, Milky Way stretching clear across valley, no light pollution. Architecture, land, and sky speaking the same language. Where hosting feels like breathing, completely natural. 5 families in 227 years. You'll be 5th. 5 min to dining, 20 min to Great Barrington, 2.5 hrs to Boston/NYC. Complete and irrepla

764 E Hill Rd, New Marlborough

$3,998,000
5 Beds 6 Baths 73451336 MLS
East Hill Farm offers 227 acres of protected quiet, anchored by the elegant 1798 Thomas Shepard House. A private hilltop world.Main house: Georgian-Federal; 5 BR, 5.5 BA, ~5,000 SF; 5 fireplaces; unusually high ceilings, wide-board floors, antique glass, rooms that hold the light, views that connect. Graceful, welcoming.A complete estate that also can be a working-farm or equine property: barns + outbuildings, pastures, private trails + roads, 4+ acre pond, gardens + orchard, pool, pool house, greenhouse, tennis.A vast former Arabian horse barn, now guest compound, or for you to reimagine. Preserved with rigor, lived in with joy, and rooted in the land and history that defines the Berkshires. One of the most complete and intact agricultural landscapes remaining in Southern Berkshire County, has no true comparable. Read the history. Experience East Hill Farm. Reach out.

764 East Hill Road, New Marlboro

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