Welcome to your ultimate country retreat, where the charm of history meets the ease of modern living. Here, timeless beauty and serenity reign—an escape where silence is broken only by the wind in the fields and the song of birds. The 1828 brick colonial, a masterpiece of its era, has been exquisitely restored to showcase spacious, light-filled rooms that draw the outdoors in, framing views of meadows, a sparkling pool, and the stately barn. The barn itself is a wonder, waiting to be reimagined—perhaps as a guest house, an artist's studio, or a setting for unforgettable gatherings. Surrounded by farms and opening to distant hills, the landscape feels both boundless and intimate. The pool, perfectly placed, invites leisurely afternoons and is graced with its own elegant pool house.

Move-in ready and beautifully upgraded, freestanding home offers the ease of one-level living paired with over 4,600 sf over three finished levels. Four br, 4.5 bat and a walkout lower level. Live at the desirable Miraval golf/resort campus. Hardwood floors flow throughout the main living area, anchored by a striking double-sided fireplace wi stone hearth connecting the living and family rooms. Custom shades throughout add a polished, designer touch. Rear deck offers magnificent views of October Mountain. Upper level includes open loft, private office, 2 br with en-suite baths. Lower level extends the living space significantly, ideal for guests with bedroom, bath, media/exercise room, glass sliders to the outside. Short level walk to pool, golf, fitness, restaurants. Luxury living!

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.

Multi generational Possibilities & Income potential! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Pickle Ball, Library, golf & restaurants. Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3 Bedrooms,, 3 Baths, has a lovely brookside courtyard w/Pergola, rustic charm maintained. Quiet your mind and embody perfect country living. Overlook the Kampoosa Brook, with private swimming area from your backyard! Cultural & recreational activities nearby. Great income potential. Solar powers Main house, car charger & Mill House. A MUST SEE!

Experience the best of Berkshire living in this stunning contemporary waterfront home on Stockbridge Bowl. Thoughtfully designed, this 4 BR, 3 full bath year 'round home offers a seamless blend of modern comfort and natural beauty! Sunlight pours through expansive windows, framing breathtaking water views from nearly every room. The open concept living space is anchored by a striking double sided fireplace, creating a warm and inviting atmosphere for both every day living and entertaining. The kitchen flows effortlessly into dining and living areas, all oriented to capture the lakefront setting. The deck is the perfect place for dining or simply soaking in your surroundings and a private dock provides direct access for boating or swimming. Your opportunity to own a turnkey retreat!

Some homes offer extraordinary settings. Others offer exceptional living. Rarely does one offer both. Embracing its extraordinary setting, this classic center hall Colonial is all about the way it lives. The heart of the home is an inviting open kitchen with a breakfast nook and a beautiful sitting area where walls of glass and French doors open to a stunning stone patio, tranquil waterfall, and exquisitely landscaped gardens. The adjoining dining room and front-to-back living room with a soaring cathedral ceiling and charming fireplace create warm, inviting spaces for family gatherings and entertaining. A magnificent 1800 sf post & beam barn with cathedral ceilings offers endless possibilities as an artist's studio, yoga retreat, office, media room, wellness space, guest house.

This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, updated plumbing and electrical, 5-zone heating, central air, and other modern systems. In 2022, a new well and a boiler for radiant heat were also added. Step inside to find timeless Colonial charm--exposed beams, three original fireplaces, and gorgeous antique floors--seamlessly paired with an expansion which added a large family room with a fourth fireplace, finished basement storage, mudroom, and partially screened wraparound porch.

Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. newly renovated clapboard and shingle house with covered porch. Meticulous renovation features chef's kitchen, four+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or professional office. High-end appliances, including 6-burner Wolf stove and Bosch French door refrigerator with two freezer drawers, Bosch dishwasher, wine cooler and microwave in the island. Full-size prep sink in the kitchen island, 36'' farmhouse sink in the main counter. Cabinets are all-wood with soft-close drawers and doors; vented whole-house A/C and heat pump with propane back-up; primary bath with heated floor

Welcome to Camp Mohawk, a pristine lakefront property in the heart of the Berkshires. Set on Cheshire Reservoir--a serene, largely uninhabited lake--the property offers both privacy and convenient access just off Berkshire County's main north-south route. Once a summer camp, the estate features an existing main house and barns listed on the National Register of Historic Places, dating back to the late 1700s. There are also numerous sleeping cabins that could be restored. Ideal as a private family compound or for development as a spa or resort, corporate or wellness retreat, or condominium, single-family, or retirement community--the possibilities are truly endless. Can be subdivided.

Tucked at the end of a long, winding drive, where nearly twenty acres of woodland create an exceptional sense of privacy, this expansive contemporary residence feels quietly removed from everything--yet remains just minutes from the cultural and recreational treasures that define the Berkshires. The house reveals itself gradually. Cathedral ceilings lend a grand sense of arrival to the entry and living room, where expansive windows fill the home with natural light and frame changing views of the surrounding landscape. From there, the home's scale shifts naturally to spaces that feel warm, comfortable, and inviting.

Perfetto. A pebbled, willow-shaded drive welcomes you to a classical villa elegantly and privately set in a coveted location minutes from Great Barrington. Taking design cues from ancient Rome and built to exacting standards, its light filled interiors yield fully protected views of fields, meadows and mountains. Sophisticated details and quality craftsmanship are everywhere evident--19 sets of French doors for ideal indoor-outdoor flow, varied ceiling heights, living room with custom mantel, serene primary suite, guest wing, central courtyard with formal gardens and reflecting pool, pergola and lap pool, and chef-ready kitchen, central AC, and generator. Privacy, ease, and expansive views, all in a 2,716-square-foot sanctuary on Baldwin Hill.

This exquisite single-family home spans an impressive 4,300 square feet, offering an unmatched blend of elegance and modern comfort. With 5 spacious bedrooms and 4.5 beautifully renovated bathrooms, every detail has been meticulously crafted to perfection. Walking distance to downtown Great Barrington's shops and restaurants, the house is in one of the quietest areas of ''The Hill''. 12 rooms including a formal dining room, a sophisticated library/den, and a versatile media/recreation room. The chef's kitchen, featuring premium counters, a WOLF range, a Sub Zero refrigerator, a wine cooler, and a butler's pantry for seamless entertaining. The home is filled with natural light. Comfort is ensured year-round with air conditioning and central heating on every floor.

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.

Truly, a one of a kind, stunning property both inside and out with scenic views of the sprawling land down to Long Pond. This thoughtfully crafted and designed home was curated to incorporate the natural serene outdoors into gracious open common spaces allowing warm natural light and comfortable flow. The first floor boasts the great room with wood burning fireplace open to the chefs kitchen with a large pantry and dining with built ins, unique sunroom with walls of glass and screened porch that extends the indoor outdoor living space while overlooking the pergola, play house and down to the water. The first floor primary en suite and office/den sitting area offer privacy in its own separate wing. The second level has ample guest space with three bedrooms, two en suite full baths and

A Landmark Berkshire Estate of Extraordinary Provenance, the Oliver Wendell Holmes summer cottage. 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

EXPANDED CONTEMPORARY CAPE Appointed with elegant detail, masterfully crafted, this stunning home is nestled on over 9 private acres offering 9 rooms, 4 bedrooms, 3 full and 2 half baths. An open floor plan flows seamlessly from the generous living room, featuring a striking coffered ceiling and a fireplace surrounded by natural raw granite, into a large kitchen and dining area perfect for entertaining. A stunning wrought iron detail by Ivan Bailey enhances the staircase.. A media room with glass-paned sliders and built-in bookcases completes the exceptional living space. The first floor primary ensuite is a true retreat, boasting a soaring vaulted ceiling and two large walk-in closets. The second floor offers three additional bed rooms, and two full baths.

At the Lenox/Stockbridge town line on the shore of Lily Pond, sits this architectural gem! Offering a rare combination of privacy artfully aligned with nature and a premier location. Set on six acres within the grounds of the original historic Wheatleigh estate, the property is within walking distance of Tanglewood, the Linde Center, Kripalu and Lenox village. Designed by Berkshire architect David Rothstein, the house is ideally positioned to engage its landscape. Large bay windows invite natural light and frame views of water, trees, and gardens. Custom cherry woodwork adds warmth and craftsmanship. The layout is both flexible and refined. First floor primary suite supports single level living, while 3 additional bedrooms and a library occupy the upper level. Lofts, towers and

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 over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure. Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury. MORE

April Hill, an exquisite 1850 Greek Revival masterpiece. This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate showcases classic stone walls, a serene spring-fed pond and a heated saltwater pool. The impeccably maintained lawns and expertly designed grounds establish a pristine country retreat. Premium upgrades include superior rock wool insulation throughout. Perfectly positioned just minutes from Tanglewood's celebrated performances, fine dining and thriving cultural attractions in the Berkshires.