Sited down a long shared drive this lovely contemporary colonial style home is incredibly private. Circular drive brings you around the front entry, the current owner extended the house to give it a proper entry and created a lovely front porch. The living space is flanked with windows to the private backyard and open to the kitchen and dining area. A large great room sits on the south side of the home and the soaring ceilings and multiple skylights give it a solarium feel flooding it with light. Kitchen is large with good working space, a pantry closet, counter seating and french doors to the screened porch and patio. The side entry brings you from the 3 car detached garage through the coveted boot room into the kitchen with laundry tucked away. Upstairs there are 3 guest rooms, a hall

Jaw-dropping water and sunset views from every room define this beautiful contemporary overlooking Lake Garfield. Offered fully furnished, this Berkshire retreat features a chef's kitchen flowing into a light-filled great room and screened porch. Four bedrooms -- including an ensuite primary -- plus a spacious family room offers plenty of room to gather. Linger on the screened porch, entertain on 2 decks, or unwind in the hot tub as the sun sets over the water. Privately sited on 2.5 acres, this is refined Berkshire living -- a truly magical place to escape, gather and enjoy.

Built in 2021, this contemporary home offers 5,670 sq ft of living space on 2+ acres, just 5 minutes from Great Barrington. Enjoy mountain views and stunning sunsets from the open-concept first floor featuring vaulted ceilings, a fireplace, chef's kitchen with large island, coffee bar, and ample storage, all flowing into spacious dining and living areas. A screened porch extends living space for three seasons. The main level includes a mudroom with laundry, oversized 3-car garage, two offices, and powder room. Upstairs: two guest suites and a primary suite with fireplace and large bath. The finished lower level adds 1,900 sq ft with game, gym, media rooms, guest bedroom and full bath. Central air and fiber internet available. Can be purchased fully furnished outside of list price.

Your private Berkshire retreat! Sweeping views of Squaw Peak, surrounding mountains, 42 beautiful sub-dividable acres with trails, seasonal brook, room for pool, tennis court, family compound. Warm, welcoming 4BR, 4.5 bath, home with room for family, friends, gathering or quiet escapes. Sun-filled fireplaced LR with picture window, cozy window seat framing the view; elegant formal DR with window wall and fireplace. Spacious chef's kitchen with island, dining area, TV area, comfy wood stove, leading to the large screened porch and expansive deck--perfect for morning coffee, summer dinners or simply relaxing. 3 main-level BRs include ensuite primary. Above-grade LL offers office, 4th BR, bath, inviting fireplaced family room. 2-car garage. 1 mile to downtown Great Barrington.

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.

A remarkable turn-of-the-century Colonial where timeless architecture, meticulous care, and gracious proportions come together beautifully. Set against a backdrop of sweeping Berkshire views, the home captures a sense of elegance and permanence rarely found today. Rich in character yet beautifully suited to modern living, this is a home that feels as extraordinary as its setting. and cutting-edge modern comfort. Designed for both entertaining and intimate family life, this c1930, 6800 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately

Set on approximately 62 acres spanning both sides of Cone Road, Middle Branch Overlook Estate offers sweeping southeast views across the Middle Branch of the Westfield River valley. The 3-bedroom timber-frame home features warm pine interiors, open living spaces, a first-floor primary suite, lower-level recreation room, and two additional flex rooms, plus another room above the garage for office, studio, or expansion potential. Amenities include a heated pool, gazebo, gas fire pit, 3 garages, workshop, generator, and 56 solar panels on the house and garage. Open fields, woodland, brook, ponds, trails, and substantial road frontage may offer potential for additional lots, subject to approvals and buyer due diligence. Majority in Chapter 61B.

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.

Located on one of Columbia County's finest roads in the town of Spencertown, this impeccably-maintained private 2922 sq ft. colonial home on 7.4 acres has all of the modern amenities! A fabulous setting with stunning distant views, the home features an open chef's kitchen and great room plan, which was expanded and redesigned in 2021, with Sub Zero refrigerator, Wolf gas oven and Miele dishwasher stainless steel appliances, subway tile backsplash and separate island. The home features a central hallway with an elegant living room and working fireplace, dining room, home office/den, washer/dryer units on both the first floor and basement, central AC and full-house generator. In addition, there is a second driveway entrance with RV/EV electric, which leads to a park-like meadow with walking

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.

Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side captures the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere you look you stop to take in the view, large bath with walk-in closet and laundry. The inner courtyard has a heated pool, sunken jacuzzi, outdoor shower, screen porch with fireplace and beautiful perennial gardens. Hidden off the drive is a guest cottage with open living area, bedroom and full bath.

The subject property is a single story office use building that contains 14,440 square feet. Built in 1998, the property is on a slab on grade founda-tion with a decorative block and metal sided exte-rior; there are fixed framed windows and a pitched metal roof. The building has three 10 foot by 10 foot overhead doors and one, 14 foot by 10 foot overhead doors at ground level. The over-head doors are located at the rear of the building; this area is accessible through a fenced in portion of the site that is utilized by the anchor tenant for vehicle and equipment storage ,Spectrum. The interior is divided into two tenant occupied units. Pittsfield Community Television occupies 4,608 square feet of updated office type space and utilizes it as a television studio and office space. This unit

Set in one of Egremont's most coveted locations, this remarkable contemporary residence commands sweeping views across the surrounding landscape, with beautifully curated gardens that create a setting of exceptional beauty and privacy. Thoughtfully conceived and meticulously crafted, the home seamlessly integrates sophisticated contemporary architecture with carefully preserved elements of the original 1940s cottage, resulting in a residence of warmth, character, and enduring style. Light-filled interiors flow effortlessly to expansive decks and a welcoming front porch, inviting year-round enjoyment of the breathtaking setting. A striking stone fireplace anchors the main living space, while rich natural materials and finely executed details reflect the home's exceptional craftsmanship . .

A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90± acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style. The original mansion remains at the heart of the property, surrounded by broad lawns and a collection of buildings added during its later evolution into an educational campus.

Originally built in the 1700s, this historic post-and-beam barn has been thoughtfully renovated over time while maintaining its unique character and charm. A recently installed solar energy system allows for highly efficient living with the potential for an off-grid lifestyle. The home features an open floor plan filled with natural light from numerous oversized windows. A chef's kitchen adjoins the dining area, creating an ideal space for entertaining. With three full floors of living space, the home offers four ensuite bedrooms plus an additional bedroom, providing comfort and privacy for family and guests. Enjoy seamless indoor-outdoor living with a screened porch off the main level leading to spacious decks and a hot tub. The lower level includes a media room and sauna for relaxation

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.

Nestled in the picturesque Berkshires, this historic circa-1776 Richmond estate seamlessly blends Colonial charm, timeless elegance, and premier equestrian amenities. The expansive compound features a beautifully maintained seven-bedroom, 7.5-bath main residence/Inn, three guest cottages, multiple barns, and a spacious entertaining barn. The distinguished main home offers a gracious dining room, entrance parlor, stately library, cozy den, period greenhouse, and well-appointed kitchen. An equestrian enthusiast's dream, the property boasts lush paddocks, multiple barns, a 6,000-square-foot heated indoor riding arena with viewing area and owner's apartment, and a professional outdoor riding ring, providing exceptional facilities for year-round training and entertaining.

Welcome to 19 Buckingham Lane, a completely turnkey, beautifully curated waterfront retreat designed by internationally acclaimed interior designer Jess Cooney of Jess Cooney Interiors. Offered fully furnished, this newly renovated home sits directly on the shores of Lake Garfield and features four bedrooms and three baths across three levels. Soft earth tones, richly textured wood finishes on floors, walls and ceilings, and elegant stone surfaces create a relaxed yet sophisticated atmosphere for lakefront living. Tucked into a private cove, it offers exceptional peace and seclusion while the expansive deck provides the perfect setting for entertaining with sweeping water views. And if you don't own a boat, you're in luck--one is included with the sale.

349 Old Stockbridge Road and 40 Frothingham Crossing together represent a rare 16.76± acre contiguous institutional campus and redevelopment opportunity in the heart of Lenox--one of the Berkshires' most established and sought-after destination markets. At the center of the offering is Overlee, a distinguished Berkshire estate built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan / Jacobean Revival style. Over time, the estate evolved into a fully integrated campus, thoughtfully organized around the original mansion and supported by a collection of dormitory residences, academic and administrative buildings, dining infrastructure, and recreational facilities.

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