Experience the rare opportunity to own your own island on beautiful Dudley Pond! This stunning post-and-beam bungalow offers 360 water views and an unmatched sense of privacy. Enter via a cobblestone driveway featuring an antique millstone centerpiece. Inside you'll discover wide-plank pine floors and yellow pine beams dating from the 1700s. The chef's kitchen boasts an oversized quartz island, abundant custom cabinetry, induction cooktop, and double wall ovens. At the heart of the home, a magnificent Russian Fireplace serves as a striking architectural centerpiece. Custom built-in bookcases, two bay windows and light-filled living spaces create warmth and character throughout. Upstairs, a cozy seating area with laundry hidden behind double doors. The primary suite offers a cathedral

Nestled in the lovely gated community of Woodmont Estates, this magnificent Georgian Schultz-designed home offers five bedrooms and five baths, with effortless access to all the Berkshires have to offer. Step through the elegant front entrance into a grand foyer featuring an open stairway, flanked by a formal dining room and spacious living room. Continue on to the expansive chef's kitchen, complete with a large center island and sun-filled breakfast area.Upstairs, the second floor showcases generously sized bedrooms, including a luxurious primary suite with its own private office area.Outdoors, enjoy a stunning wraparound deck overlooking the in-ground pool--perfect for entertainment and relaxation. The beautifully landscaped grounds feature an open outdoor fireplace surrounded by

Updated and spacious condo just a short distance from Main Street Stockbridge, downtown Lenox, and all the Berkshires has to offer! Premier Unit at Stockbridge Terrace: Enjoy peaceful living on a private cul-de-sac with a limited number of units. The main level living setup is perfect for the primary resident, featuring a large primary bedroom with an en-suite bath and walk-in closet, an open-concept kitchen that has been recently updated complete with top-of-the-line appliances and all new high end cabinetry. The Great Room boasts cathedral ceilings bringing an abundance of natural light and a soaring gas fireplace for added ambiance. Enjoy your private backyard views from the 4-season sun porch equipped with both heat and A/C for year-round comfort.

This fine, four-bedroom, two bath colonial saltbox home just south of the village of Stockbridge is a handmade work of art and an important slice of Stockbridge history. It was constructed on or about 1750. There are patinaed wide board floors throughout as well as five fireplaces (three wood and two gas) and much original hardware. The home is surrounded by perennial gardens and a formal, boxwood garden, all of which have been meticulously maintained. There are two stone patios which look out over four acres of pasture to the west. This home is fueled by gas heat and is serviced by town water and sewer. Perhaps the famous Reverend, Johnathan Edwards and Chief Kondapot of the Stockbridge-Munsee Indians met in the front parlor a time or two.

CLASSIC ARCHITECTURE WITH CONTEMPORARY ELEGANCE! A beautifully maintained home set back from the road. Exceptional landscaping embraces the property, offering a private sanctuary. A front porch welcomes you to the first floor. A light-filled,capacious living room, dining room with a fireplace opened to both main rooms, a primary suite with two walk-in closets, a 1/2 bath, and study open to a large kitchen and laundry room with access to the two-car garage. The second floor has a loft, three bedrooms, two full baths, generous closets, and storage spaces. A spacious deck with screened-in gazebo are at the rear of the house. Walk to Lake Mansfield, 5 minutes to vibrant downtown Great Barrington, Mahaiwe Theater, Triplex Cinema!

Designed in 1929 by noted architect Henry Seaver (Berkshire Museum, Lenox Town Hall), this distinguished Georgian Colonial was once the centerpiece of Pittsfield's social scene. The home preserves exquisite 18th-century details - mantels, wainscoting, and finely crafted woodwork salvaged from two of the city's earliest residences, making it a living piece of Berkshire history. Set back on 2.5 private acres along prestigious Crofut Street, the estate offers 5 bedrooms and 5 baths, including twin primary suites ideal for hosting friends and family year-round. Gracious living and dining rooms, a peaceful sunroom, a cozy study, and a large eat-in kitchen with Viking range and butler's pantry combine period elegance with modern comfort. This turn-key estate is offered fully furnished and

THEY DON'T BUILD HOUSES LIKE THIS ANYMORE.They don't build love at first sight anymore, either. But Sky Hill Farm - a genuine 1798 Federal colonial in Tyringham Valley - has been creating that exact feeling for over two centuries.In 1912, Adele LeBourgeois Chapin wrote about first arriving here at dusk, walking through high grass to the old front door with its worn stone steps and feeling the homely welcome as she went in. ''This old house was beautiful,'' she wrote, ''the rooms perfectly proportioned, the mantlepieces charming old Colonial ones... I felt as if I was at home at last.''That feeling hasn't changed. Views of Tyringham's Shaker Fields65+ acres3,443 sq ft3 bedrooms2 1/2 baths2 barnsPasture & Hay fieldsFor the whole story click MORE -or reach out

Escape the city and embrace the tranquil rhythm of lakeside living in this stunning 3-bedroom, 2.5-bath waterfront home. Located on the desirable northeastern shore of Lake Buel, this property is your turn-key ticket to summer on the water. The open-concept living space is flooded with natural light from a wall of windows offering panoramic views of the serene lake. Enjoy your morning coffee or evening cocktails from the three-season room, feeling the gentle lake breeze. Your private dock awaits, offering effortless access for boating, swimming, and kayaking. Imagine spending your weekends exploring the pristine waters, followed by a quiet evening watching the sunset paint the sky. This isn't just a second home; it's a legacy of memories waiting to be made. Your Berkshire escape is here.

This beautiful home was built in 2006, and updated in 2022. The house is situated on just shy of 5 Acres in the town of Egremont. The home is flooded with sun all day, rarely needing a light on in the house. Direct access to the Green River at the edge of property to cool off on those hot summer days. A new central AC system was installed throughout home and apt A New backup generator, rain gutters, new lighting inside and out, full painting inside and out in 2025. First floor primary suite with jet tub and separate shower. The oversized rear screened in porch is divine, you will never want to leave. A Giant lawn for entertaining and a separate in law apartment for your guests. The garage with radiant heat is perfect for your classic cars or boat. Low Taxes and 5 minutes to GB town.

This stunning 6-family home sits on 1.5 acres, a large lot that goes from Forest St to Silver St, a convenient location with easy access to the Mass Pike and just a couple minutes away from the Lee Outlets. This multi-family consists of 3 two-bedroom units, 2 one-bedroom units, and a 4 bedroom 2 bath unit. The large unit offers a welcoming front porch, living room, eat-in kitchen, full bath and primary bedroom on the 1st floor, and 3 bedrooms and full bath upstairs. This expansive apartment would make a great owner's unit, or rent it out for additional income! Some of the improvements done in the last few years include new kitchens and bathrooms in 5 apartments, new roof, 2 new high efficiency heat/hot water systems and mini-splits. All units have separate heat, hot water & electricity.

The Woodlands -- A Private 74-Acre Retreat in Great Barrington!A rare opportunity to own a private and picturesque Berkshire retreat in the heart of Great Barrington. Set on seventy-four acres of meadow, orchard, and forest, The Woodlands offers a refuge of uncommon scale and serenity--just two minutes from Ski Butternut and five minutes to downtown Great Barrington's restaurants, shops, and cultural life. The property abuts the Thomas & Palmer Brook Reserve, a Berkshire Natural Resources Council preserve spanning more than 300 acres of protected woodland and scenic trails, extending your own land into a vast network of wild beauty.

A total 41 acres includes a 2nd building lot of 26 acres allowing one to build ones own home with mountain views. A 36x52 work shop. One full time residence and a separate summer studio. Some land does go into New Marlborough. Surrounded by conservation land. Passive solar views facing South and West. Property has been a sculpture park for many years. Trails throughout. Views to Connecticut.

''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage''Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming 1BR guest cottage, with large living room and mini-splits, is ideal for rental income or private guests. Garages for 5+ cars, perfect pool site, and privacy ensured by abutting protected land.

A master stoneworker and his family spent a year walking 11 acres to find the one perfect spot. Then they built their dream around it - every fieldstone placed by hand from rocks cleared by 150 years of farming, hand-hewn cherry beams harvested from the land soaring above the stone-clad Great room. This rustic modern farmhouse embodies the truth that in simplicity lives beauty. The timber-framed screened porch catches every breeze, while the spa-like steam shower opens directly to an outdoor shower enclosed by artful ''lace walls.'' Closed-cell insulation, owned solar array, and rich oak floors throughout create effortless comfort. Now, as the ocean calls them back, this net-zero sanctuary awaits those who will write its next chapter. Read the full journey of this modern farmhouse!

An equestrian dream property offering country living among the scenic hills of Western Massachusetts. Set on 15 acres with over 1,300+/- feet of frontage on the North Branch of the Manhan River and 900+/- feet of road frontage, this exceptional estate provides tranquility, function, and world-class facilities. Perfect for the boutique horse enthusiast, boarding operation, or hosting equestrian events.The property features nine paddocks and a hunt field with multi-species hemlock fencing, top-board electric hot wire, Jug waterers, and ample space for vehicle and trailer parking. The showcase three-stall barn with attached 80' x 180' indoor arena was built in 2019 using SIPS construction for superior energy efficiency.

Set on 4.7 beautifully landscaped acres with distant views, this impeccably maintained home offers generous space, thoughtful craftsmanship, and remarkable indoor-outdoor living.Located just minutes from so many of the Berkshires' most beloved attractions, including only 15 minutes from the main gate at Tanglewood, this Richmond property also boasts easy access to major traffic routes connecting you conveniently to both New York and Boston. Your ability to enjoy the region's culture, adventure, and cuisine starts right here.

Welcome to Cannondale Compound. Set on 20 private acres with far-reaching mountain views, this 7,300-square-foot architectural retreat is ideally suited for large gatherings. Designed with soaring modernist lines and exceptional craftsmanship, the home offers multiple living and dining areas, seven bedrooms across two connected wings, expansive porches and balconies, and both indoor and outdoor pools. Outdoor highlights include a hot tub, pool house with bathroom, pavilion, garden, and a fully enclosed treehouse for summer overnights, along with deeded Queechy Lake rights for swimming and kayaking.The main wing of the home features a dramatic triple-height great room with a fieldstone fireplace, flanked by a wraparound deck.

A beautiful Contemporary on 11 private acres, 6 miles to downtown Great Barrington. Soaring ceiling great room. The open-plan, gourmet kitchen feature's a Viking range, stone countertops, and a large pantry leading to a delightful four-season porch, perfect for enjoying the western views. The large living room in centered by a striking floor-to-ceiling chiseled stone fireplace, cathedral ceilings, and glass doors leading to the rear deck, lovely first floor en-suite primary with a new beautiful bath. Flexibility and comfort, the home includes two additional ensuite bedrooms and a nursery room on the second floor, plus a third floor dorm room ensuite. A beautiful front porch an attached two-car garage and a classic barn complete this special property. Minutes to downtown Great Barrington.

Stunning Post and Beam Home with Log Facade. Nestled in a park-like setting with views of Mount Washington. Outdoor Amenities Galore. Extensive patios and wraparound decks provide the perfect venues for outdoor gatherings including a private bocce ball court, outdoor hot tub, and private dog park. The first floor offers generous entertaining spaces, including two to three bedrooms that provide flexibility for guests or additional family members. The open kitchen/dining area is perfectly positioned to capture southeast-facing views. The primary suite includes a luxurious bath and expansive walk-in closets. On the lower level there is a private walkout suite, full bath, gym, and kitchenette. 3 car oversized garage/shop and generator.

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite--pool, fitness center, clubhouse, and tennis--all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.