Once the cherished country residence of acclaimed wildlife artist & tableware designer Lynn Chase, this gracious 4-bedroom manor dates back to 1850, and had a major update in 1998. Set on 5.96 acres of rolling pasture framed by stone walls, this charming estate is spacious but manageable, complete with a garage/horse barn, larger barn, fenced paddocks, and a small pond. Rich in character and period detail, this Greek Revival home boasts wood paneling, exposed beams, built-in cabinetry, and antique flooring. The 1st floor offers plenty of space for entertaining, with a formal entry, spacious receiving room, library, and parlor - each with working fireplaces. A 1998 addition introduced a bright open kitchen/dining area with French doors opening onto an elegant south-facing bluestone patio.

Just a half mile beyond New Marlborough village, this architectural gem offers 5,653 square feet of superior craftsmanship in an enchanting private setting along the Umpachene River. Distinctive circular towers, flowing curved walls, and graceful arched windows are in perfect harmony with the surrounding natural landscape. Custom millwork and premium natural finishes offer a balance of warmth and luxury in this elegant but comfortable 5-bedroom 4.5 bath home. Enter through the grand foyer into the expansive kitchen, living & dining areas, anchored by a striking Scandinavian Soapstone wood stove and a marble wood burning fireplace. A sunny breakfast room off the kitchen leads to a greenhouse atrium and an impressive indoor pool pavilion, fully heated for year-round enjoyment.

A striking modern retreat where architecture and landscape exist in complete harmony. Designed by internationally noted architect Alfredo Brillembourg, the home blends clean contemporary lines with warm natural materials and dramatic connections to the outdoors. Expansive walls of glass frame seasonal Berkshire views while filling the interior with changing light throughout the day. The living spaces feel both refined and deeply livable -- soaring ceilings, open gathering areas, and thoughtfully composed volumes create an atmosphere that is at once sophisticated and relaxed. A sleek modern kitchen flows effortlessly into the main entertaining spaces, while private 1st & 2nd floor bedroom suites offer quiet separation and a sense of retreat.

HISTORIC BERKSHIRE FARM Best bargain in the Berkshires! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 acres with stunning views, mountain paths, and Jim Kelly's stunning giant stonewalls throughout. Gorgeous New England marble stone farmhouse built in 1780, with modern addition featuring vaulted ceiling and massive windows which flood the dining and kitchen area with light. Enormous custom built hearth and fireplace, mahogany full bar, artisan-made bookcases, wrap-around deck. Close to Williams College and Jiminy Peak. The property offers swimming in two private ponds, 6 bay carriage barn with second floor for offices, studios., or storage.

Surrounded on three sides by Nature Conservancy-protected land, 173 Hillsdale Road is one of the most private and extraordinary estates in the Berkshires -- a handcrafted sanctuary where the wilderness is literally your backyard. Moose, deer, bear, fox, and turtles roam master-gardened grounds tended with rare care; fruit trees, a garden pond, mature perennial beds, and lush native plantings make every season a revelation. Custom-built in 2000 from timber milled directly on the property, this 4,842 sq ft home carries an irreplaceable provenance that announces itself at every turn. A native stone fireplace anchors the soaring vaulted great room. An ash sapling banister curves to the interior balcony above. Antique leaded glass casts dappled light across wide-plank floors.

Iconic Lenox home: very rarely does a home with this historic integrity come on the market...now is your time to continue its legacy . Built in 1915 as one of the focal points of Cliffwood Street, this charming home has been updated for today's life style without sacrificing its significant architectural details. Beautiful common rooms including a dream kitchen with marble counters, formal Dining Room with French doors to the enclosed porch and onto the new deck and acre of land; formal Living Room with fireplace, family room and welcoming foyer off the front porch. The 2nd floor is home to all 5 bedrooms plus an inviting ''summer porch'' off one! Updated baths, kitchen, roof, utilities...and add to that: crown moldings, pocket doors...this home is truly a rare find in today's market

COMMANDING VIEWS OVER LAKE GARFIELD WITH A STUNNING MOUNTAIN BACKDROP, this beautifully updated home offers charm with modern refinement. Original architectural character has been thoughtfully preserved, while expansive windows fill the home with light and frame the breathtaking scenery. Recently renovated chef's kitchen, first floor primary bedroom, and loads of closet space address today's needs. And could there be any better spot to watch sunsets than the expansive front porch? What's more, a well-appointed suite in the separate carriage house offers flexible space for guests, a home office, or artist's studio. Features include eight private acres, high speed internet, low Monterey taxes, and proximity to the Monterey bathing beach and the incomparable tomatoes at Anna's farm stand.

Beautifully restored historic Colonial on a lightly traveled, town maintained road with stone walls, fruit trees, open meadow, wooded acreage, and a barn or garage. Bordering protected land and offering about a mile of road frontage, the setting feels private, quiet, and deeply rooted. Long associated with author Simon Winchester, this is a rare Berkshire antique with depth, authenticity, and lasting appeal. c.1760 and 1840. 4 bedrooms, 3 baths. Library, keeping room with original crane fireplace, Aga kitchen, vaulted living room, screened-in porch. A c.1812 granary rebuilt as a writing studio with loft and full bath. Stone walls, orchard, meadow, vernal stream. 50 acres. 3/4 mile road frontage. Borders protected land. A setting that feels sheltered, rooted, and quietly beautiful. CLICK

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare colonial charm. The legendary c. 1776 estate boasts a well maintained main residence/Inn, three cottages and a great barn for entertaining. The residence/Inn features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. Its dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that caters to both intimate family gatherings and grand celebrations. For the serious equestrian, the estate offers multiple barns and paddocks. Training is a year-round luxury thanks to the 6,000 square foot heated indoor arena, which includes an owner's apartment and viewing area--and a professional-grade outdoor ring.

Welcome home to NEWGRANGE. 1920's era Manor House with lake frontage on Lake Garfield. Over 10,000 square feet of living on 7.7 Acres. Complete the restoration and enjoy original Stone Fireplaces, comfortable Living spaces, formal Dining and 10 Bedrooms. Write that novel in the paneled Office, Library or Sunroom, create delicacies in the Country Kitchen, or shoot a round of pool in the Billiard Room. When you are done, meander to your private Dock on 165 feet of glorious private lakefront. Guest House, Pond, and Gardens originally designed by Frederick Law Olmstead. Close to town, Skiing, Shopping, Dining and Tanglewood. Low, low Monterey taxes. This one-of-a-kind property is meant for enjoying all that the Berkshires has to offer.

The thoughtfully renovated and expanded 1940s Main House is full of exceptional spaces--elegant formal dining and living rooms in front, informal sitting area and spacious eat-in kitchen at the back, stunning central stairwell, cozy den/bar, and media room. Five comfortable bedrooms, including two luxurious primary suites. Every material, sightline, and design element has been curated with care and sensitivity. Delightful outdoor spaces abound--front and rear goshen stone patios, rolling lawns, balconies and roof spaces. Cozy historic sunroom off the living room. Above the oversized two-car garage, is a stunning light-filled studio with intricate ceiling details, exterior balcony and bathroom. The in-ground pool is surrounded by a huge patio area, gardens and pastoral views.

Stunning Views! Exquisite Tudor-style stucco estate set on more than 18 breathtaking acres with panoramic views and a winding approach that creates an extraordinary sense of arrival. Bright, airy, and thoughtfully designed, this 5-bedroom, 5-bath residence blends timeless architecture with modern comfort and exceptional indoor-outdoor living. The heart of the home is a stunning great room featuring soaring ceilings, abundant natural light, and hardwood floors throughout. An open-concept layout flows seamlessly into the generous chef's kitchen, complete with a professional-grade gas range, spacious dining area, and direct access to the expansive deck overlooking the rolling landscape. The main-level primary suite offers privacy and convenience with a spacious bath and ....

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket doors that provide charm and flexibility. Every detail has been curated to embody warmth and sophistication, creating an inviting ambiance that is both refined and welcoming. Ideally located just moments from downtown Lenox, Tanglewood, a local municipal airport and a charming farm, HomeFarm, directly across the street. Highwick offers an unparalleled sanctuary in the heart of the Berkshires!