This striking modern retreat was designed by internationally recognized architect Alfredo Brillembourg to feel completely at home in its Berkshire setting. Clean contemporary lines, warm natural materials, and expansive walls of glass create a seamless connection between the house and the surrounding landscape. Seasonal views and changing natural light bring a different feel to the home throughout the day. Inside, soaring ceilings and open gathering spaces make the home feel impressive without being formal. The sleek modern kitchen flows easily into the main living and entertaining areas, while private bedroom suites on both the first and second floors offer comfortable places to get away.

Just beyond New Marlborough Village this architectural gem showcases 5,653 square feet of superior craftsmanship along the Umpachene River. Built in 1989, this 5-bedroom home was designed by internationally renowned architect Paul Bierman-Lytle, a pioneer in sustainable development and healthy home design known for championing non-toxic climate adaptive building materials. Distinctive circular towers, curved walls, arched windows and premium natural finishes harmonize with the surrounding natural landscape. The grand foyer opens to an expansive kitchen, living, & dining space anchored by a striking Finnish soapstone wood stove and marble fireplace. A sun-filled breakfast room leads to a greenhouse atrium and an impressive indoor pool pavilion, fully heated for year-round enjoyment.

Spectacular Homestead! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 pristine acres with stunning views, mountain paths, and 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.

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 very lightly traveled, town-maintained road with stone walls, fruit trees, open meadow, wooded acreage, a barn and garage. Three quarters of a mile of its own road frontage, bordering protected land. Home to author Simon Winchester for twenty-five years. .. 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. .. Orchard, meadow, vernal stream, quiet forest. 60 acres. A genuine Berkshire country place with a sky that still delivers. Located in Sandisfield, in the Southern Berkshires. Two and a half hours to the city. Two centuries of history on 60 acres. Read the whole story. '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.

Extraordinary and expansive estate property near the top of the hill on prestigious and desirable Bulkley Street. Consisting of three separate parcels over 11+ acres, this offering provides a rare opportunity to acquire an expanse of gorgeous acreage within minutes of Williamstown center, Williams College, the Clark Art Institute, the new Williams College Museum of Art, and close by the 2600 acres ecological reserve, Hopkins Memorial Forest. The four bedroom, three and one half bath main house, sitting atop the hill, has been beautifully updated while maintaining its gracious character and features an array of public spaces both intimate and open, with an especially appealing four season sunporch overlooking the lovely gardens, graceful and sweeping grounds, and the distant ridgeline.

A Landmark Berkshire Estate of Extraordinary Provenance. Set on 15 private acres in the heart of the Berkshires, a rare American legacy estate commissioned in 1847 as the summer residence of renowned physician, poet, & author Oliver Wendell Holmes Sr. Two centuries later, this extraordinary property remains a testament to architectural elegance, literary heritage, & timeless craftsmanship. The offering preserves original hardwood floors, intricate millwork, & the grandeur of a distinguished era. Its storied halls welcomed literary icons including Longfellow, Melville, & Hawthorne. Surrounded by exceptional privacy, Holmesdale is more than a residence, it is an irreplaceable American landmark and a rare opportunity to become the next steward of Berkshire history.

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.

Set on 30 private acres bordering Beartown State Forest, this exceptional Berkshire estate offers a rare combination of timeless farmhouse architecture, refined craftsmanship, and complete privacy. Built in 2018, the 4,700-square-foot residence is thoughtfully designed to blend seamlessly into its surroundings, creating a home that feels both elegant and deeply connected to the landscape. Filled with natural light and beautifully proportioned throughout, the home offers four bedrooms, five bathrooms, and inviting spaces designed for both everyday living and effortless entertaining. At the heart of the home, the chef's kitchen features Vermont Danby marble countertops, a spacious pantry, and an inviting breakfast nook that opens to the surrounding gathering spaces.

Welcome to NEWGRANGE, a grand 1920s Manor House capturing the golden age of lakeside country living. This historic estate echoes the effortless elegance of an early 20th-century summer retreat. Imagine hosting lavish gatherings in the formal dining room, or retiring by original, roaring stone fireplaces after a leisurely day on the water or the slopes. Encompassing over 10,000 sqft, the sprawling residence boasts ten spacious bedrooms, a classic country kitchen, and sweeping living areas. Stroll the 7.7-acre grounds--past the guest house, pond, and gardens originally designed by Frederick Law Olmsted--down to your private dock on Lake Garfield. Ideally located near Tanglewood and premier skiing, and low Monterey taxes, this Berkshire gem is a rare invitation to reclaim a masterpiece.

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 ....

As seen in Architectural Digest, this meticulously reimagined 1875 farmhouse compound unfolds across 11.5 lush acres on a quiet, bucolic dead-end country road, with protected views. Brought to life in collaboration with AD100 design firm Sachs Lindores and landscape design by Judy Murphy, the property is full of historic character with refined modern comfort. The compound includes a four-bedroom, four-bath main house, a one-bedroom, one-bath guest house and a large barn relocated from New York State. Outdoors, a private heated in-ground pool, gas-fired pizza oven and fire pit, orchard, fenced vegetable garden, and poolside outdoor shower create an idyllic country retreat. All systems were replaced in 2019, with high-speed internet and central A/C, just minutes from Great Barrington.

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!

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.