Below you will find currently listed luxury homes in the Berkshires. If you have a question about a property, contact us. You can also sign up for an account with our site to start saving your favorite listings and receive email notifications as new properties match your search criteria.
SOUTHMAYD FARM Gilded Age at its finest in Stockbridge. This 1870 Berkshire estate has been fully restored & is privately sited on 33+ acres within walking distance of town. Adjacent to the Stockbridge Golf Club & the Norman Rockwell Museum, the view includes a mile of Housatonic River frontage. The 8500' main house w/ 8 bedrooms is complemented by a carriage house, greenhouse/studio, pool, , 3 bedroom guest house, barn complex and paddocks, a magnificent maze, and additional formal gardens. See documents file for detail of each building, room and floor plan.
Listed by Cindy Welch and Keith Ross of LANDVEST, INC.
Unsurpassed 19th Century Queen Anne Style Berkshire Lenox ''Cottage'' restored and reinvented for today's most discriminating family wishing for an understatedly elegant, 'cool' and comfortable Twenty-First Century lifestyle. See attached document for all details. Shown by advance appointment only.
Listed by Mary Jane White and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES
Casually elegant and beautiful shingled eco-luxury mountaintop home with rare and extraordinary protected southerly long-range views, abutting 12000 acre Beartown State Forest. Carefully and exquisitely crafted, the gracious rooms feature four fireplaces with a hefty stone central core, mahogany windows and doors, and radiant heated wood floors. The horse barn has three generous stalls, a tack room, and caretaker's quarters. Horses enjoy organic pastures and an outdoor arena that could easily be a tennis court. The private setting and views are unmatched in the southern Berkshires, and the quality of construction speaks for itself.
Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS
This exquisite home is in the Canyon Ranch subdivision of Pinecroft, walking distance to the wonderful village of Lenox. Ownership offers the option of membership to the world class health and wellness resort. The home is being offered furnished. Features include a gated and heated driveway and courtyard, heated in ground pool and fabulous fully equipped pool house with outdoor kitchen. The home boasts custom interior design, steam shower, gourmet kitchen and a wet bar in the living room. The lower level offers a sauna, climate controlled wine cellar, hi-def movie theatre and a magically nostalgic soda fountain!
SUPREMELY WELCOMING...One of Lenox's19th century Berkshire''cottages'' that has been meticulously restored and updated. Located on prestigious Cliffwood Street within walking distance of downtown Lenox, this exceptionally welcoming Berkshire "cottage" on 3.17 acres epitomizes gracious living with a porte cochere and sixteen fireplaces . Meticulously restored and updated, the six-bedroom house has many original architectural details such as paneled walls, carved mantelpieces and a two-tier staircase with an oculus on the second floor that overlooks the generous foyer (large enough for a baby grand piano.) The main floor has exceptional flow for a 19th century house: The library and living room with adjoining den (separated by pocket doors) have massive French doors that open onto a large screened porch; the dining room, with built-in corner cabinets, and billiards room are ideal for entertaining; the cook's kitchen with capacious dining and lounge areas opens onto a large deck. The adjacent mudroom, with a contoured entry doors, still has the original "call board" for the servants. In the basement, there's the original ice room and a dumb waiter for transporting firewood to the upper floors. This property has a gracious driveway, mature gardens, a privately situated swimming pavilion and a barn-like garage that can accommodate five cars. One of the few 19th century cottages that has been maintained as a private residence, this is a rare opportunity to live in a park-like setting so close to town.
Listed by Deborah Levinson of BERKSHIRE PROPERTY AGENTS
GREAT BARRINGTON MASTERPIECE. Designed by the world renowned and award winning architect, Kenneth Nadler. Reminiscent of an Arts and Crafts mansion. This superb stone and cedar Contemporary home sits majestically on 10 acres of privacy within walking distance to downtown. The features are a mixture of old world with every modern day convenience including soaring ceilings, intricate moldings, a kitchen that will satisfy the most discerning of chefs, a sumptuous master suite that is serene and beautiful and an elevator just to name of few. Delightful from beginning to end this home offers quality, charm, and grandeur. Nothing was spared in this unique and truly special home. Nadler designed a home for Beyonce and Jay Z.
Listed by Maureen White Kirkby of BARNBROOK REALTY, INC.
Many dream of converting a historic barn into a country house. A barn tells a story, has a past, and the old beams, posts and boards have a patina and a magic which new construction can never recreate. This 26 acre estate is masterfully designed and crafted from two 18th & 19th century barns on one of the Berkshire's finest country lanes in North Egremont. 65 Shun Toll Road embodies a rustic elegance that will simply captivate you as you gaze across the soaring, yet brilliantly intimate spaces and through the expanses of glass to the inspiring and extraordinary distant views of farmland below and mountains beyond. Offering nearly every luxury imaginable in its 6, 600 square feet, yet in an ultimately comfortable and authentic manner - the perfect Berkshire country home.
Listed by L. Chapin Fish of BROCKMAN REAL ESTATE, LLC
A meandering drive through a hardwood forest leads to this 11, 800 sq ft family retreat in the Berkshires. The wood shingled home was built in 2003 on a ridge near the center of the quaint village of Alford. The home offers great privacy with sunset views, yet is only a 20 minute drive to Tanglewood and other cultural amenities offered in the area. A 2,400 sq ft studio and 800 sq ft pool cabana are next to the house. Beautiful gardens are woven through dramatic rock features and flagstone paths. The four-bedroom home offers large rooms for entertaining as well as more intimate spaces. Custom stained glass windows frame the forests and views from the breakfast room adjacent to the gourmet kitchen, and from the expansive living room with fieldstone fireplace and bar. A mural featuring local historic places showcases the grand staircase. The master bedroom features his and hers bathrooms and dressing rooms, as well as a kitchenette. A home theater, game room, bedroom/workout room, and wine cellar are located on the basement floor. The home is handicap accessible, with an elevator, wide doors throughout, and a ramped entry. This offering includes 26.9Â± acres and improvements at 50 East Road as well as an additional 8.7Â± acre lot.
A RARE OPPORTUNITY TO OWN A PRIVATE 9.6 ACRE ESTATE ON OTIS RESERVOIR, the largest recreational lake in Massachusetts. Enjoy the breathtaking, westerly views over the water to Tolland State Forest. Like an exclusive resort, the compound has its own secluded beach (286.66 ' of water frontage), a floating raft, a new dock for mooring your boat and jet skis, as well as a waterfront gazebo, tennis/basketball court and an old softball diamond. Built in 2003, the contemporary timber-frame house with traditional details has seven bedrooms and eight-and-a-half bathrooms. The open-flowing 3,800 square-foot first floor has exquisitely crafted cherry floors, vaulted wood and cathedral ceilings, handsome beams and water views from nearly every room. The public spaces include a cook's kitchen, formal dining room and library with built-in bookcases plus a great room and den both with massive stone fireplaces Two first-floor masters plus an en suite guest room open onto a waterside deck that runs the length of the house. Designed for large-scale entertaining, the 3,480 square foot lower level features a media room/movie theater, sauna, weight room and game room with a fireplace and wet bar. Four additional en suite bedrooms have walk-out access to a hot tub and lawn that slopes down to the lake. Built on the highest point of the Land's End peninsula that was formerly the Simchak Blueberry Farm, the property still has hundreds of blueberry bushes along with apple trees, stone walls, mature gardens and several tree houses. Five outbuildings include an oversized two car-garage next to the house, a four- car pole barn with an unfinished second level, an antique barn and two small equipment sheds. One of the largest properties on Otis Reservoir, this compound is both an arcadian summer camp and luxurious year-round retreat. Offered at $3,125,000 On the adjacent .29 acre waterfront property, there's a 2006 three-bedroom, two-and-a-half bath Cape that can be purchased for $995,000.
Listed by Barbara Schulman and Jen Harvey of BERKSHIRE PROPERTY AGENTS