Tucked away at the end of a private road on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio

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.

Looking for a Berkshire getaway that can help pay for itself? This unique 6-unit property in Lee offers the rare opportunity to enjoy a spacious 4BR/2BA home of your own while generating income from 5 additional apartments. Full of character, the property retains many of its beautiful original features with significant updates, including renovations to 5 of the 6 units, a newer roof, updated electrical and newer heating systems. Set on a spacious property with ample parking, public water and sewer, and separate utilities, it offers tremendous flexibility for seasonal, short-term or year-round rentals. Centrally located near the Mass Pike, downtown Lee, Outlets, Tanglewood and all that the Berkshires have to offer. An ideal combination of Berkshire lifestyle, character and income potential!

Entertainer's Delight! Tucked away in one of Sandisfield's most scenic settings, this quality-built log home offers over 4,600 sq.ft. of finished living space, plus an additional 2,000+ sq.ft. in the walkout basement ready for living, recreation, or storage. Crafted with exceptional materials, the home features soaring ceilings, expansive gathering spaces, and a warm, inviting atmosphere perfect for entertaining or everyday living. Multiple decks provide an ideal setting to dine, unwind, and enjoy the peaceful natural surroundings. Experience the perfect balance of privacy and convenience, just 20 minutes to Guido's and downtown Great Barrington, 30 minutes to Lenox and Tanglewood, and 15 minutes to Ski Butternut. A true Berkshire gem for year-round living, weekend retreat, or investment!

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.

Tucked away on a peaceful private drive, this custom Craftsman home (built 2022) combines timeless architectural character with effortless modern living. Designed with accessibility and everyday ease in mind, the main level features zero-step entry and true single-level functionality. At the heart of the home is a bright, spacious cook's kitchen that flows seamlessly into welcoming living spaces. Outdoor living shines with both a classic front porch to take in quiet sunsets and a stunning screened porch designed for bug-free Berkshire evenings. The versatile 4-bedroom layout features a private primary suite alongside an attached in-law apartment-ideal for multigenerational living, long-term guests, or rental potential. A dedicated home office makes remote work a breeze,

Experience refined Berkshire living at Coldbrooke East, where timeless elegance meets exceptional privacy. Perfectly sited at the end of a quiet cul-de-sac and abutting the golf course, this extraordinary six-bedroom, 5.5-bath residence offers luxurious single-level living with a thoughtfully designed 1,000-square-foot addition. Custom designer finishes, exceptional craftsmanship, and substantial built-ins create a sophisticated yet comfortable totally renovated interior. Outside, magnificent perennial gardens, privacy, outdoor showers, and courtyard provides a serene retreat. Enjoy access to the nearby Wyndhurst Club and Manor pool, tennis courts, reduced-rate fitness membership, and more. A rare offering combining luxury, lifestyle, and one of Lenox's most coveted settings.

A significant price reduction has just been made on this terrific revenue opportunity property in Stockbridge. The historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. THIS PROPERTY HAS AN EXCELLENT HISTORY OF RENTAL INCOME. The ''Ice House'' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more exists close to Main Street Stockbridge, Norman Rockwell Museum, Tanglewood, and all the most important cultural amenities. Rental income? This property has a very nice history of rental income! Who could ask for anything more? Call for a showing today

The Ultimate Vermont Mountain Sanctuary: Discover total serenity at the end of a winding gravel road. Encircled by 37 acres of pristine woods, a natural pond, and sprawling lawns, this impeccably maintained contemporary estate offers complete isolation from the outside world. Located in peaceful Stamford, you are just minutes from Premier Vermont skiing boating, and hiking, as well as the world-class dining, theater, and art of the Massachusetts Berkshires. The Great Room Experience: Ascent to the 2nd level and prepare to be breath-taken. The spectacular great room features soaring 18-ft cathedral ceilings, rich all-wood finishes, and a magnificent stone fireplace. A towering wall of glass frames panoramic views of the tree-covered mountains. Step onto the massive 20x29 deck to experi

Extraordinary, Inside and Out. This stylish log home on 3+ acres is the complete Berkshire retreat. Recently updated and improved, the home pairs modern lodge character with resort-like amenities. A heated saltwater gunite pool and integrated hot tub anchor the beautifully landscaped grounds. A locust fence encloses the pool area, with bluestone patio, lush lawn, and a stunning renovated pool house designed for entertaining, dining, or remote work. Inside, the home is warm, open, and full of character, with the added benefit of true one-level living. The great room is the centerpiece, with soaring ceilings, exposed log beams, and a substantial stone fireplace.

Nestled in the center of Williamstown, just steps from Williams College, this stunning two-story Colonial stucco home offers timeless charm and modern comfort. Built in 1907, this 4,100 sq. ft. residence features five spacious bedrooms, three full baths, and one half bath. Set on 1.35 picturesque acres, the property boasts a large post-and-beam barn, a beautifully covered stone patio, and breathtaking western views of the Taconic Mountains. The expansive, level backyard is adorned with mature gardens and majestic old-growth trees, creating a serene and private retreat. Don't miss this rare opportunity--call today for your private showing!

Beautifully designed and thought out, this spectacular home offers both a first and second floor Primary Suite (or guest suite) plus 2 additional bedrooms on the 2nd floor. In addition you have formal living & dining rooms, a huge eat in kitchen with sliders to patio and 2nd staircases both up and down; 2nd floor has an additional FR/bar/deck. And to complete this grand home, the lower level is finished into a flex space with 4 additional rooms plus a bar area. Heating is geo thermal, natural gas with central A/C. Beautiful architectural features with high coffered ceilings, beautiful moldings, columns, hardwood floors, marble, granite & ceramic finishes, 3 FPs plus two patios and a beautiful back yard to enjoy the Berkshires. This is truly a special home!

LUXURY PROPERTY AUCTION: 29 OCTOBER - 1 DECEMBER. Current list price reflects the current high bid. Estimated sale price: $2M-$2.5M. Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market. The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety f

Steeped in the timeless elegance of historic Stockbridge, this exceptional Colonial captures the enduring charm of a bygone era, evoking the quintessential New England scenes made famous by Norman Rockwell. Beautifully sited just moments from the heart of town, this distinguished four-bedroom residence blends classic architectural details with gracious, comfortable living. Inside, three fireplaces anchor inviting gathering spaces filled with warmth and character, while three spacious ensuite bedrooms offer exceptional comfort and privacy. Rich period details, handsome proportions, and abundant natural light create a home that is both sophisticated and welcoming. Beyond the main residence, a separate guest cottage provides the perfect retreat for visitors, extended family, a home office,

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.

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

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.

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.

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!

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.