Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26.

A DRILLED WELL, A COMPLETE 6 BEDROOM SEPTIC SYSTEM, A HORSE BARN AND A SHED COMES WITH THIS FABULOUS 42 PLUS ACRE PARCEL. BEAUTIFUL STONE WALLS SURROUND THE BUILDING SITE AND ACROSS FROM PROTECTED LAND

Discover this breathtaking timber-frame home sited on a peaceful and private 10-acre park-like setting central to the Berkshires. Redesigned by architect Pam Sandler, who added a vaulted great room ceiling, a welcoming front porch, a spacious screened porch, and a 3-car garage. Featuring a first-floor en-suite primary bedroom, a generous living & dining area anchored by a commanding fieldstone fireplace, and a well-planned kitchen with all stainless appliances. Three upstairs bedrooms have ample closet space, and the basement family room with a wood-burning stove offers a cozy winter retreat. This eco-friendly home features a newly built barn, solar panels, and heat-pump climate control. There is so much to experience in this beautifully updated home, just 10 minutes from Tanglewood.

Dreaming of your own private sanctuary? 30+ acres await exploration! Enter between two stone pillars and the long winding driveway will take you past woodland glades, open spaces, mature tree stands, manicured lawns and a magnificent spring-fed swimming quarry! Acres of open cleared land afford additional usage options. Cedar log home, one-owner custom built. Large wrap-around deck and long covered porch; great for summer entertaining! Inside you'll enjoy over 2000 sf of relaxed country living. Great room with vaulted ceiling, massive stone fireplace. Open kitchen w. granite counters and island w seating. Two first floor bedrooms and full bath. Upper level with spacious primary suite and an open loft with fireplace. Finished walk-out lower level w. 2 car garage. Truly one-of-a-kind!

Special Berkshire retreat on 25 private acres in Harrington Woods with beautiful views. Offering 5,400 sq ft, this 4-bedroom, 4-bath home features oversized rooms and high ceilings. The main level includes a recently renovated chef's kitchen, expansive primary suite with walk-in closets, guest room/office, library with built-ins, dramatic living room and a 400 sq ft screened porch. The walkout lower level offers two additional bedrooms, exercise room, family room, professional pool table, sauna and steam shower. Additional highlights include an oversized 2-car garage with Level 2 EV charger, 12x24 storage shed, and a 30-panel solar array with a transferable utility credit. HOA amenities include tennis, pickleball and a heated seasonal pool. Minutes to Otis Ridge and Great Barrington.

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

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 Rumsford 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.

Set on 22 private acres, this Monterey retreat offers a peaceful escape from city and suburban life. Freshly painted this spring, it's near Lake Garfield and Monterey Town Beach, and across from Beartown State Forest. The bright, expansive home features four ensuite bedrooms, including a spacious primary suite, large entertaining areas, and cathedral & vaulted ceilings. Outdoors, enjoy a 16' x 40' heated gunite pool, an outdoor enclosed shower, a large stone patio, and the year-round Loom Brook flowing through the woods. The lower level includes a sauna, exercise pool, and utilities. A two-car garage connects to a mudroom with laundry, half bath, and outdoor shower, plus a large bonus room above. A rare opportunity at this price in scenic, convenient Monterey, with fiber internet.

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.

Perfectly positioned on the border of Hancock and Williamstown, this striking Post & Beam contemporary estate offers a rare blend of architectural sophistication and rustic elegance. Spanning approximately 27 acres of meadows and woodlands, this property serves as a secluded sanctuary with views of countryside, mountains, and it is 3.5 miles to Jiminy Peak Ski Resort. The home's interior unfolds across three expansive levels defined by windows, views, soaring ceilings, and rich hardwood flooring. The main living areas include a cozy living room with a Mansfield model wood-burning stove, media/music areas, and a 3-season sunroom that flows seamlessly onto a spacious trex deck. The chef's kitchen is a masterpiece of function and style, complete with a walk-in pantry and dining area.

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.

Properties of this magnitude and character are becoming a true rarity in today's market. Brookmede Farm, isn't just a listing; it is a magnificent blank canvas of 22 beautiful scenic acres, defined by sweeping mountain views and a profound sense of quiet serenity. From the moment you arrive, the silence and the scale of the landscape invite you to imagine the unlimited possibilities. Whether you envision a world-class equestrian estate, a sustainable organic farm with cows and chickens, or a sophisticated multi-structure family compound, this land provides the space and the soul to make it a reality. Standing as a centerpiece to this vision is a towering, three-story Timber Frame barn. With its incredible volume and structural presence, it offers a

A once-in-a-lifetime opportunity to build your dream home on a large waterfront parcel in Lenox. This spectacular 14-acre property offers privacy, tranquility, and direct frontage on beautiful Laurel Lake while remaining just minutes from downtown Lenox, Tanglewood, shopping, dining, and all the Berkshires has to offer. Enter through the stone and metal electric gate, cross the stone bridge, and arrive at a cleared, manicured homesite ready for your custom estate or compound. A scenic boardwalk winds to your private dock and lakeside sitting area. Truly a rare Berkshire offering combining natural beauty, convenience, and waterfront living.

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!

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.

Custom contemporary home built in 1996 with thoughtful gathering spaces. Main floor has a vaulted ceiling living room with fireplace, open to dining and the eat-in-kitchen. Down a hall to the south end there is the primary suite, a powder room, laundry, the den with vaulted ceiling and a woodstove and access to the garage. On the north side of the main living room is a large entry foyer, a great room with woodstove and 3/4 bath. Upstairs there are two bedrooms, a hall bath and ample closet space. The lower level has a walkout section with a large bedroom, hall bath and a hall that takes you into the below grade finished area with office, play space and extra room. The screened porch off the entry foyer leads to a very large deck on the east side of the property angled southeast with views

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!

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.