Experience the beauty of Berkshire lakefront living on beautiful Pontoosuc Lake, where breathtaking sunrise views, peaceful waters, and exceptional privacy create the perfect year-round retreat. Nestled in the heart of the Berkshires, this beautifully remodeled home blends luxury, comfort, and thoughtful design, ideal for both everyday living and entertaining by the lake.

Tucked away at the end of a private cul-de-sac 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

Well maintained and set in a prime Egremont location, this home is perched above the Egremont plain with open views. Quiet and private, yet just minutes to downtown Great Barrington, Egremont and everything the Berkshires has to offer. The main level is bright and welcoming, with an open living space centered around a wood-burning fireplace. A first-floor library adds a quiet, separate space; ideal for a home office while the kitchen connects directly to the deck, creating an easy flow for indoor/outdoor living and a perfect spot to take in the views. The upper level features three bedrooms, including a primary ensuite, along with a full bath and an additional den that can easily serve as a lounge or office. The lower level offers a full in-law apartment complete with it

LOCATION, LOCATION, LOCATION. This terrific home is in low-tax Egremont, setback from road, & is a short walk to French Park which sports new tennis/pickleball courts, a playground, hiking trails, a basketball court, and a dog park. The town also features two of the more popular restaurants in the Berkshires. But, what about the house? This well maintained 4 bedroom/3 bathroom home is wheelchair accessible, and meticulously maintained. There is an in-apartment that might be rented as an apartment or a professional office. Ever been inconvenienced by a power outage? Not at this house because it has a 10kW generator. Worried about roof conditions? Not a concern at this house. The steel roof should be good for another 40 to 50 years. Schedule a showing today! SEE MORE...

Exceptional Federal style reproduction farmhouse located in a peaceful setting on a scenic country road. Offering 3-4 bedrooms, 3.5 bathrooms, beautiful hardwood and marble floors. The kitchen with Viking range, custom cherry cabinets, granite countertops and walk-in pantry opens to a family room with a brick Rumford fireplace. The formal dining room opens into the living room. There are French doors to a heated sunroom that connects to a barn/garage with 2nd floor great room and full bathroom. The grounds include a bluestone patio and Goshen steps to the home. Property setting has mature landscaping and perennial gardens. Adjacent undeveloped 2.5 acre lot included.

Tucked away at the end of a long driveway and perched atop its own private hill, this stunning 3-bedroom, 2.5-bath post-and-beam home offers complete privacy and breathtaking mountain views. The open floor plan is centered around a dramatic floor-to-ceiling fieldstone wood-burning fireplace, with soaring ceilings, exposed beams, and beautiful pine floors throughout. The primary suite includes a private bath, while two additional vaulted-ceiling bedrooms share a full bath. Enjoy central AC, a metal roof, board-and-batten siding, portable generator hookup, and a large dry basement for storage. Outside, relax on the expansive rear deck, swim in your spring-fed pond, fish on a lazy Sunday afternoon, and enjoy spectacular sunsets and incredible stargazing from your own hilltop retreat.

One of the most exceptional homes to come to market, this remarkable property blends timeless elegance with resort-style living. Featuring 5 bedrooms, 3.5 baths, including private guest quarters with bath and secondary staircase, this home offers both sophistication and versatility. The luxurious primary bedroom suite is a true retreat, complete with a spacious en-suite bath designed for comfort and relaxation. A stunning new kitchen serves as the heart of the home, thoughtfully designed for both everyday living and refined entertaining. Impeccably curated interiors extend seamlessly to breathtaking outdoor spaces highlighted by a spectacular heated in-ground pool, extraordinary landscaping, and meticulously maintained grounds. A true masterpiece of design and luxury living.

Step into history at 1001 Canaan Southfield Rd, a rare 1797 Colonial estate set on over 23 breathtaking acres of mature, landscaped grounds. This extraordinary property features two serene ponds with fountains, over 300 feet of classic stone walls, and the scenic Umpachene River winding through the land. Extensive landscaping, stone patios, and picturesque outdoor spaces create a private retreat unlike any other. The home offers 4 bedrooms, including a spacious primary suite, blending timeless character with natural beauty. Included are three separate parcels, with an additional lot located across the street, offering endless possibilities for expansion, recreation, or investment. A truly one-of-a-kind Berkshire property rich in history, charm, and unmatched natural surroundings.

Set on a desirable tree-lined dead-end street in the heart of Lenox, this beautifully restored 1937 Cape blends timeless character with exceptional craftsmanship. Featured in Berkshire Magazine, the 3,740 sq. ft. home offers original heart pine floors, a wood-burning fireplace, and extensive updates including new plumbing, electrical, Pella windows, roof, and central AC. The three-level layout features 3 bedrooms, 4 full baths, two upper-level suites, and a finished lower level with a guest suite, office, and workshop. French doors open to a wraparound veranda overlooking Goshen stone terraces, fruit trees, and a fire pit. Enjoy sidewalk access to downtown, and Tanglewood is just minutes away.

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!

Discover a rare lakefront opportunity on Otis Reservoir with amenities seldom found in one property. Combined with the lower lot, enjoy 62 feet of direct waterfront, a grandfathered boathouse with electricity and electric lift, waterfront bathhouse with living room, heated garage, dedicated hot tub room with fireplace, and lake views from nearly every room. Perfect for entertaining with an updated kitchen, multiple living areas, separate driveways, ample parking, and two storage sheds. Remodeled in 2021 with new heating and cooling, on-demand hot water, quartz island, stacked cabinetry, stainless appliances, and gas range. Walk-out basement. Sold fully furnished and ready to enjoy.

In the Berkshires, the rarest luxury isn't simply a beautiful home--it's finding a place that makes you want to stay a little longer. Welcome to 130 East Dugway Road. As you arrive, the pace of life begins to slow. Morning coffee lasts a little longer, evenings linger beneath Berkshire skies, and weekends become treasured family traditions. Thoughtfully designed for both elegant entertaining and quiet retreat, this exceptional home blends timeless architecture, refined craftsmanship, and inviting living spaces that feel as welcoming as they are beautiful. Just minutes from Lenox, Tanglewood, and the region's finest cultural attractions, this is more than a remarkable residence--it is the place where generations gather, memories are made, and the Berkshires truly feel like home.

CONTEMPORARY FARMHOUSE! Sited on a knoll dotted with old apples trees overlooking scenic views all framed by a meandering fence. All you could ask for is in this well-built home, offering a first floor primary ensuite, library with fieldstone fireplace, A well appointed kitchen opens to both the dining and a living room with fireplace. A screen porch, 1/2 bath, laundry room/mudroom leading to a 2 car garage completes the first floor. The second floor offers 3 addition bedrooms, full bath, built-in bookcase with window seat. Kick back and relax on the front porch! A fabulous Berkshire house close to all Berkshire cultural venues, skiing, shopping, restaurants and, just plain fun!

Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes -one a four bedroom home and a 1000 sq ft guest house-both 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. Spacious garage allows room for cars, hobbies and workshop, perfect pool site, and privacy ensured by abutting protected land. Generator for both houses.Access to town beach.

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.

An incredible opportunity to surround yourself with privacy and exceptional views of Mt. Greylock. This amazing contemporary with detached guest house is sited on 4.5 acres. The main house offers 4 bedrooms, 2.5 bathrooms, kitchen with butler's pantry, granite countertops and modern appliances. The kitchen flows into the formal dining room w/wood burning fireplace and access to a covered deck. The living room with vaulted ceilings is enhanced by a floor to ceiling fieldstone propane fired fireplace and access to a large inviting deck. A hexagon barn was completely renovated into a delighful guest house with private deck, kitchen, bathroom, 1st floor bedroom and additional sleeping area on the 2nd floor. The property is enhanced by beautiful professional landscaping. Many Upgrades.

Experience refined Berkshire living at Devon Meadows, one of the area's most desirable luxury condominium communities. This beautifully appointed residence offers the ease of a first-floor primary suite combined with sophisticated design and exceptional comfort throughout. The open-concept floor plan features soaring ceilings, abundant natural light, and elegant modern finishes. The chef's kitchen is thoughtfully designed with quartz countertops, custom cabinetry, and seamless flow into the dining and living spaces--perfect for both everyday living and entertaining. Custom built-ins add character and functionality, while an inviting den or home office on the main level provides flexible space for work or relaxation. Guests will appreciate the privacy of well-appointed en-suite bedrooms.

This Stockbridge home has it all...privacy, protected view, river frontage, plenty of room for all washed with natural light and location, location, location!! Down a town maintained country lane, this special property welcomes you to this spacious home with living rm, great room w/fp, den/office, open kitchen/dining w/wall of glass leading to the wonderful screened porch & spacious decking, mud room off 2 car garage, laundry & half bath complete the main level. Upper level has generous primary en suite with balcony overlooking the serene yard and two guest bedrooms and bath. Centrally located for easy access to restaurants, theater, shopping, museums, skiing, cultural venues and only ,minutes to the Village of Stockbridge!

Just minutes from Tanglewood on the sunny side of Lenox Mountain, this lovely five-bedroom, five-bath home is privately set on almost eleven acres of rolling lawn and woodland. A welcoming foyer opens to a light-filled great room where a striking two-sided stone fireplace creates distinct living and dining spaces, all flowing to decks, a terrace and a screened porch. The main level also features a library/den, a primary suite, laundry room, powder room, and an attached two-car garage. Upstairs are three guest bedrooms and two full baths, one being en suite. The walk-out lower level offers a fully self-contained one-bedroom apartment along with extensive storage. Outside, the expansive pastoral grounds provide ample space for a pool, while Lenox Mountain Brook meanders through the propert

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.