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51 Photos
LANCE VERMEULEN RE, INC
$1,195,000
3 BD | 2 BA
Residential - Single Family

Welcome to a place to gather, unwind and recharge. Just 5 minutes from the heart of Monterey, this serene property spans over 13 acres of peaceful woodlands at the end of a quiet country road, providing a true haven for family and friends. Surrounded by perennial gardens, a natural pond, and an expansive forest, this home embraces both indoor and outdoor living. The Great Room is perfect for gatherings and features a grand stone fireplace, a cozy sleeping loft and a wall of windows and doors that lead to a stone patio. A second, more intimate living area with its own fireplace and exposed beams is situated just off the kitchen and dining room, opening onto a deck and a screened porch. The entire length of the house enjoys westerly views of a lush pond fed by the Buck River.


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Compass Massachusetts, LLC
$1,200,000
2 BD | 2 BA
Residential - Single Family

This classic eyebrow colonial, set on 18 acres, has been transformed into an efficient modern two bedroom home. The interior lines are elegant and clean, the transitions to the outdoors simple and harmonious. A well-balanced landscape features marble stone work, fruit trees, blueberry bushes, a seasonal stream and a fenced garden ready for the next season.Climb the moderate west facing slope to the tree line and experience one of the most gentle and beautiful land parcels in South County. This land has been partially cleared, offers lovely late afternoon light and gracious western views.The location is perfect, the taxes are low - bring your imagination.


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WILLIAM PITT SOTHEBY'S - LENOX
$1,250,000
4 BD | 4 BA
Residential - Single Family

Discover your dream home in the desirable Becket Woods community! This stunning, recently renovated property offers three spacious levels of living, featuring abundant natural light from skylights and impressive vaulted ceilings. Enjoy cozy evenings by the fireplace in the living room or unwind in the generous first-floor primary suite with ensuite bathroom and soaking tub. With over 3,700 square feet of stylish contemporary design, the open layout seamlessly connects the living, kitchen, & dining areas. Lots of sleeping spaces with 4 bedrooms plus bonus rooms that include a loft and 3.5 bathrooms, enough space for everyone. The finished lower level adds an extra 821 square feet perfect for family fun and currently furnished with a cozy sectional, television and ping pong table.


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$1,395,000
5 BD | 4 BA
Residential - Single Family

Executive colonial sited on over 1.3 acres bordering 17 acres of conservation lands. Hike off your property on Parsons Brook Conservation area or relax in your professionally landscaped backyard with fire pit, waterfalls, 35/70 yd tee boxes w/ synthetic putting greens and 18x36 inground saltwater pool and pool house w/ kitchen. The expansive main residence offers a balance between open concept entertaining, yet offering quiet, cozy areas when needed. Bonus spaces include a 4-season sunroom, home gym, media room and for the ultimate in game day gatherings, the third floor has an expansive entertainment room with custom 8-person wet bar, three tv's, and pool table. High level technology with Solar, 17kw backup generator, 52 speakers in/out Sonos system and whole property security system


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HOUSATONIC REAL ESTATE
$1,475,000
1 BD | 2 BA
Residential - Single Family

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.


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BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$1,550,000
4 BD | 5 BA
Residential - Single Family

This home has just about everything you're looking for and more!A 4.62 acre private setting, just 5 minutes into Great Barrington and low Egremont taxes! 4 Beds & 4.5 baths with an in law loft apartment. Wide open back yard with plenty of room for a pool if you dont feel like cooling off in the crisp & refreshing Green River at the rear end of the property. First level of home has a primary suite with large jet tub and separate shower. Open the slider and slip onto your screened in porch. Washer dryer on first level as well as den/0ffice. Seperate dining room with open concept living room /kitchen that leads out to the rear deck or screened in porch. Attached over size 3 car garage. Enormous basement. additional barn and plenty of storage wherever you look! Freshly painted and updated!


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THE KINDERHOOK GROUP - PITTSFIELD
$1,590,000
11 BD | 13 BA
Residential - Single Family

The iconic Wainwright Inn, built in 1766, is ideally located on Main Street in Great Barrington, the largest town & hub of the famous Berkshires vacation destination in Western Massachusetts. The Inn consists of a main house with 9 guest suites & a spacious owner's suite, & a carriage house with an apartment & two additional guest suites. In pristine condition, the current owners have improved the property significantly to include: AC system, new kitchen, structural upgrades, new parking lot and landscaping. Solid income and occupancy history. Known for its beauty, the Inn features spacious public rooms with high ceilings, fireplaces and historical details intact, and large suites, each with a bathroom. A short walk to the many restaurants & shops of the town & minutes to Tanglewood.


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HOUSATONIC REAL ESTATE
$1,675,000
12 BD | 7 BA
Multi-Family

Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully designed to meet the needs of modern living. These units feature elegant wood floors and come equipped with all necessary appliances, including dishwashers and in-unit laundry facilities. Central air conditioning ensures comfort year-round, while tiled double-sink bathrooms add a touch of luxury. Ample storage space is available in each unit, allowing residents to keep their living areas tidy.


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BERKSHIRE BUSINESS PROPERTIES
$1,980,000
11 BD | 5 BA
Residential - Single Family

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.


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LANCE VERMEULEN RE, INC
$2,299,999
4 BD | 5 BA
Residential - Single Family

The Ephraim Chapin House, a.k.a the ''Landlord Abel House'' was built in Chicopee c. 1725. In 1979 this handsome home & tavern was dismantled and relocated to Southfield. There it was re-erected upon a new foundation atop a hill, where it now resides on a 51-acre estate straddling the banks of Konkapot River. Once the beloved retreat of an artist and a serious collector of early American art and antiques this 3-story 4-bedroom home has been painstakingly rebuilt and restored.Original wainscoting in the ''keeping room'' is a rare example of interior decorative painting by the Scroll Painter, a documented but unnamed American decorative artist active the 1790's. Other details include original floorboards & exposed chestnut beams, center chimney with 6 brick fireplaces... (See ''More''.)


61 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$2,500,000
4 BD | 5 BA
Residential - Single Family

The ULTIMATE LIVE-WORK-PLAY RETREATStep onto a property as striking as the Berkshires themselves--where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The 13,738 sq ft retreat fondly known as ''The Factory'' spans 5+ acres with views of rolling hills & protected fields. 10,000 sq ft of versatile commercial and creative space below and flanked by 3,000-sq ft of stunning living spaces that seamlessly blend design, sophistication, comfort. From the glass walls that open to sweeping views, to its bespoke kitchen or design forward guest suite, every inch has been crafted to inspire. Host gatherings on the spacious screened deck, unwind by the 360 glass fireplace, find solitude in the ''Tower'' - and redefine living, creating, & thriving.


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LANCE VERMEULEN RE, INC
$2,975,000
5 BD | 4 BA
Residential - Single Family

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.


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PIRETTI REAL ESTATE
$2,995,000
7 BD | 9 BA
Residential - Single Family


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WILLIAM PITT SOTHEBY'S - LENOX
$3,295,000
5 BD | 5 BA
Residential - Single Family

Alford Stunner! Exceptionally Designed Turnkey Home with Mountain Views!Completed in 2006, this 5200+ sq ft architect-designed home comes to the market for the first time. Meticulously curated materials, interior designer finishes, and a high-end build culminate in this showpiece home on 19.3 acres, with gunite pool and pool house.Upon entry, this home exudes warmth, style, and comfort - the perfect assemblage of textures and materials.Antique Douglas Fir floors and mushroom wood ceilings frame the living room's locally quarried stone fireplace and large southwest-facing windows with mountain views. The living room opens to a light-filled, elegant dining room, which then connects to a marvelous chef's kitchen.


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STONE HOUSE PROPERTIES, LLC
$3,485,000
5 BD | 6 BA
Residential - Single Family

In 2021, The Freeman was transformed utilizing high-quality materials from an aging nineteenth-century estate to a clean and modern getaway and top-performing rental property. The main house, renovated to be 100% carbon-neutral, features six fireplaces, two dining rooms, a library, 1500sqft bluestone deck and more. The Freeman sits atop 57 acres of greenery to explore, containing a tennis court, four-acre vineyard, mountain views and a dock to access Harman Marsh Pond. Individuals, wedding parties, and corporate retreats alike have come to The Freeman to enjoy its secluded feel while being close to key Berkshire attractions like Catamount Ski Area, Bash Bish Falls, and downtown Great Barrington. This property is just over 100 miles from both Boston and New York City.


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$3,495,000
2 BD | 2 BA
Residential - Single Family

225 Acre 18 hole Golf Course / Horse Ranch in the heart of the Berkshires. Former Egremont Country Club. Build your dream home with seclusion and privacy assured. Enjoy mountain views, spring fed ponds, endless pastures, and serene forested trails. An escape from the world and yet only minutes to town and a little over 2 hours to NY City & Boston. (* Additional Acreage may be available.)


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COHEN & WHITE ASSOCIATES
$3,495,000
5 BD | 8 BA
Residential - Single Family

The Birches....welcome to your new oasis in the Berkshires where every season is memorable. This magical compound has been architecturally redesigned & renovated using the finest materials offering all the modern amenities a buyer wants to live, play, relax and work from, surrounded by 20+ acres of privacy & far reaching protected views in all directions. This stunning contemporary has big open common areas for gathering, first floor primary en suite, guest bedrooms en suite and a private two bedroom guest quarters w/kitchenette, custom crafted wine room, and an exercise room all offering plenty of space for a large crowd or intimacy for a few. Just arrive with your suitcase and enjoy all this impeccably maintained estate has to offer; a beautiful gunite heated pool w/waterfall &


91 Photos
LANCE VERMEULEN RE, INC
$4,200,000
5 BD | 7 BA
Residential - Single Family

Discover unparalleled luxury and serenity in this extraordinary 5-BR, 7-BA estate nestled in the heart of New Marlborough. Spanning over 6,000 square feet, this stunning residence is set on expansive grounds, 70+ acres, featuring a harmonious blend of wooded areas, open fields & distant mountain views. Designed by renowned architect Allan Shope, this architectural masterpiece is an uplifting retreat, seamlessly integrating modern design with nature's beauty. The home's thoughtful design takes full advantage of the sloping hillside, offering dramatic views from every angle. Inside, you'll find meticulous attention to detail, from the finest materials to timeless craftsmanship. The modern open floor plan flows effortlessly, with an indoor lap pool for year-round enjoyment.


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ELYSE HARNEY REAL ESTATE
$5,900,000
11 BD | 10 BA
Residential - Single Family

Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations to come. Set on 67 +/- park-like acres this property offers 3 unique residences, a mature specimen tree farm, a spring-fed pond, wooded walking trails, and captivating views of the distant mountains all just a stone's throw away to restaurants and shops. At the heart of the estate stands The Tullar House; a well-preserved and substantial 6-bedroom 5,000+ sq ft antique Dutch Gambrel dating back t


69 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$9,995,000
6 BD | 7 BA
Residential - Single Family

LUXURY PROPERTY AUCTION: BID 21 FEBRUARY-1 MARCH. Listed For $9.995M. Starting Bids Expected At $4M-$6M.In the heart of the Hudson Valley, this expansive 133-acre estate in Copake, New York, epitomizes luxury and refinement. The property boasts serene water frontage on the 46-acre Chrysler Pond, lush woodlands, and farm facilities, all offering breathtaking mountain vistas. The handcrafted six-bedroom lodge, constructed with timber from British Columbia, spans over 8,000 square feet, featuring a chef's kitchen, an elegant dining room, and a grand living area with a commanding fireplace of local stone and vaulted beamed ceilings. Additional amenities include a breakfast nook, sunroom, outdoor kitchen, and a spa jacuzzi overlooking the Berkshire Hills.

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