Great Barrington MA Real Estate & Homes for Sale

FARMHOUSE FRESH | EGREMONT Welcome home! Nestled in the picturesque low-tax town of Egremont, just minutes from the vibrant town center of Great Barrington experience contemporary living with a rustic charm in this light and bright haven that promises the best of country life with all modern conveniences at your fingertips. PROPERTY HIGHLIGHTS STYLISH COMFORT | Embrace the warmth of this inviting home featuring clean lines, open spaces, generous bedrooms and an abundance of natural light streaming through generous windows, illuminating each carefully considered space. GATHER AND UNWIND | Step outside into your own private sanctuary of lush gardens, thoughtfully landscaped to create intimate spaces for gathering, relaxation, and contemplation amidst nature's beauty. SWEEPING VIEWS | Be enchanted by the borrowed views of sprawling meadows and a delightful play field. The property is adjacent to conservation land complete with winding trails along the coveted Green River, allowing you and your guests to explore and enjoy scenic walks without venturing far. Seven minutes to Ski Catamount! Countryside Charm: Your idyllic retreat provides a seamless blend of country life and modern convenience. Benefit from the proximity to Great Barrington with its boutique shops, gourmet restaurants, and cultural events while retreating to the tranquility of your peaceful abode. NOTE: Taxes shown are inaccurate and for two properties which were formerly one property. 302 Egremont Plain Rd will be reassessed on sale. Roof nearing end of life, wood stove to be disconnected prior to closing. New 3BR septic system installed week of 5/13/24. FiberConnect internet available in road.

Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The Gunite pool is surrounded by an espaliered apple tree fence & generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette & massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard & patio, separate studio apartment and 4 garage bays, a barn, and cutting gardens. The custom home, built by one of the region's premiere builders, has been featured in design magazines, garden tours & has received a Garden Club of America award for its ethos & thoughtful use of building materials. The house was constructed using sustainable & recycled low maintenance building materials designed to last a lifetime. Hidden from the road, the main house is approached by a long drive lined with mature Scarlet Oaks & daffodils. A courtyard filled with specimen crabapple trees, stone walls & walkways creates the welcome entry to this 1 level home. The exterior walls are planted w/ climbing hydrangea that blur the lines between structure & nature-a common motif throughout the property. The setting is both well designed and peaceful. The grand entry foyer sets the tone for the house. It connects to an enfilade of rooms filled w/ southern sun that run the length of the house.Large windows and french doors that welcome both the light and warmth from the sun on a winter's day & open to exterior terraces in the fair months. All the rooms have extensive garden & pastoral views. The east side of the entry is the living room with high, coffered ceilings & a fireplace made with grand tour columns. Adjacent to the living room is the primary suite w/ doors to a private terrace, shower, & lawn. The velvet covered walls create perfect silence, a jewel box of a room. Dual bathrooms and closet areas w/ steam shower & large soaking tub with views complete the suite. West of the entry hall is the large eat-in kitchen w/ coveted AGA range. The doors open onto a patio with lily pond, field views, & cherry trees. The kitchen/service area includes a butler's pantry, & mudroom. The far west end of the house, with perfect evening light, has a cozy sitting room. Adjacent to this is an office/library spaces, another library is located between the guest room and the larger office/sitting room. Both library areas have custom floor to ceiling bookshelves. The larger office has french doors that open to a private and romantic courtyard garden w/ espaliered peach trees & blooms to attract pollinators. Western windows have views of a fenced field and plantings. Majestically on a small rise, is the Parthenon-like pool house, a focal point of the outdoor areas. The adjacent heated Gunite pool is a place of refuge and serenity. Step into a world of enchantment and be transported to a realm of natural beauty and tranquility. The intimate spaces and thoughtfully curated common areas throughout the property create an environment that is as classic and timeless as it is fun and whimsical. It is truly a home that seamlessly integrates its beautiful interior with the curated natural beauty and tranquility. The intimate spaces & thoughtfully curated common areas throughout the property create an that is as classic and timeless as it is fun and whimsical. It is truly a home that seamlessly integrates its beautiful interior with the curated natural beauty that surrounds it.

This lovely 1825 colonial has many of its original features in place - wide plank floors, beamed ceiling and original hardware. Combine this with newer windows, foam insulation in the basement and a well insulated attic and you have the best of both worlds. Also, the house is a legal two family offering a multitude of options - incorporate it into the main house to have a first floor bedroom suite, rent it year 'round or use it as an AirBnB (current owner did so quite successfully.) The adjacent barn/garage is currently being used as a woodworking studio but it can easily be converted to its original use. There is a carport, as well. The yard is partially fenced for dogs and the meadow view is beautiful. Tons of history here - in the late 1800's this was the post office for Housatonic

Spacious five-bedroom, move-in ready condo with high-quality finishes located in the Cottages at Barrington Brook. This warm and inviting end-unit enjoys a quiet, elevated corner of the community. Beautiful views from almost every room of the condo. Open living/dining/kitchen area with high ceilings, blush maple custom flooring, propane fireplace, and crown molding. Also enjoy the views and tranquil Berkshire days from the attached deck and screened-in porch. Thoughtfully designed kitchen with stainless appliances, honed granite countertops, and tumbled marble backsplash. The main level also includes the large primary bedroom with en-suite bathroom and gas fireplace, as well as two additional bedrooms with shared bathroom. Oversized, walk-out lower level with large living area, two bedrooms and full bathroom. Two-car garage, car charger, central A/C, solar panels, whole-house generator, and community pool. Only five minutes to Main Street.

Spacious five-bedroom, move-in ready condo with high-quality finishes located in the Cottages at Barrington Brook. This warm and inviting end-unit enjoys a quiet, elevated corner of the community. Beautiful views from almost every room of the condo. Open living/dining/kitchen area with high ceilings, blush maple custom flooring, propane fireplace, and crown molding. Also enjoy the views and tranquil Berkshire days from the attached deck and screened-in porch. Thoughtfully designed kitchen with stainless appliances, honed granite countertops, and tumbled marble backsplash. The main level also includes the large primary bedroom with en-suite bathroom and gas fireplace, as well as two additional bedrooms with shared bathroom. Oversized, walk-out lower level with large living area, two bedrooms and full bathroom. Two-car garage, car charger, central A/C, solar panels, whole-house generator, and community pool. Only five minutes to Main Street.

Discover the timeless allure of 'The Turning Point,' a quintessential Berkshire retreat nestled in the hills of Great Barrington. Originally a 1800's stagecoach stop, this enchanting 3600-square-foot property boasts a rich history as a thriving inn, short-term rental and home, offering 7 bedrooms and 6.5 bathrooms. Immerse yourself in its New England charm, complete with a wood stove, propane fireplace, wide plank floors, large kitchen, first floor bedroom, office and a welcoming floorplan emanating warmth and comfort. Perfectly situated mere moments from Butternut Basin (one of the Berkshires top ski destinations) and a short drive from vibrant downtown Great Barrington, this charming sanctuary invites you to experience the best of Berkshire living.

Pristine condition -move in ready. House sited in low tax Alford, with long winding driveway entrance in Great Barrington VIEWS from every room with floor to ceiling windows! Completely private, not another house in site and IMPECCABLE condition. Located on 17+ acres on desirable Seekonk Cross Rd in Alford sits this remarkable state of the art 7000' contemporary. Designed by famed Calvin Tsao and Zack McKown , the massive floor to ceilings windows capture the postcard panorama from every angle as the sun moves around the C shaped configuration. The winding half mile drive is lined with a long allee of trees and mature landscaping. The setting, views, privacy, landscaping, and architectural significance make 6 Seekonk Cross Road truly a rare Berkshire offering.

Pristine condition -move in ready. House sited in low tax Alford, with long winding driveway entrance in Great Barrington VIEWS from every room with floor to ceiling windows! Completely private, not another house in site and IMPECCABLE condition. Located on 17+ acres on desirable Seekonk Cross Rd in Alford sits this remarkable state of the art 7000' contemporary. Designed by famed Calvin Tsao and Zack McKown , the massive floor to ceilings windows capture the postcard panorama from every angle as the sun moves around the C shaped configuration. The winding half mile drive is lined with a long allee of trees and mature landscaping. The setting, views, privacy, landscaping, and architectural significance make 6 Seekonk Cross Road truly a rare Berkshire offering.

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 to 1761, reported to be the 2nd oldest house in Egremont. Retaining much of its original charm and detail, this historic jewel boasts ample-sized rooms for gatherings and entertaining, a renovated chef's kitchen, a formal dining room, 3 grand fireplaces, 2 primary suites, and plenty of room for guests. Enjoy sweeping views of the grounds from the porch laid with locally sourced marble or relish in the shade of 'The Champion', a 250+ year-old Black Walnut Tree standing as the oldest in the state and serving as a living testament to Tullar Farms' rich past. The exterior is a sight to behold with ornate and symbolic details that capture the attention of all who pass by. Carriage lanterns, shutters adorned with intricate heart motifs, stately marble walkways, and stone walls all add to the sense of romantic history. Complementing this historic dwelling is a striking Timber Frame barn conversion crafted by a renowned local builder specializing in restoration. This 3,000+ sq ft 3-bedroom residence features a magnificent 2.5-story Great Room with hand-hewn beams, plastered walls, and natural light cascading in creating a warm and inviting atmosphere. Two walnut staircases flanking the walls add drama to the room leading to separate bedroom wings. The Primary is private and comfortable with sitting area, fireplace, and ensuite bathroom. The open-concept kitchen, dining, and living room layout complete with radiant heat flooring and a soaring fireplace seamlessly blends modern comfort with rustic charm. Breathtaking views of the pond are enjoyed from the common areas leading to a stunning stone patio. The generously sized first-floor Den/Office with a half bath and additional fireplace provides room for seclusion. A silo made into a rock-climbing gym adds a little whimsy to this impressive residence. Further enhancing the estate is a lovely carriage house with 1,000+ sq ft of living space with 2 bedrooms, a full kitchen with an open living and dining area, and 1 full bath; 3 garage stalls and a sweet potting shed. An impressive original working barn completes the property leaving room for the imagination. Tullar Farms' blend of meticulously kept grounds and accommodations creates a welcoming canvas for residents to express their own creativity and ideas. Situated on the border of New York and Connecticut and just a short drive from downtown Great Barrington, Berkshire School, Catamount Mountain Resort, and other Berkshire attractions, its prime location offers the best of both worlds - peaceful seclusion and easy access to amenities and activities. A perfect place for individuals looking to cultivate a unique living space while still being close to the vibrant offerings of the surrounding areas.

A beautiful home that holds the integrity of an 1810 era with comfort and efficiency of todays modern living. Completely renovated in 2007 with a new foundation, all new mechanicals, foam insulation, siding, windows, roof, every stone was turned and polished to bring this house forward. Main floor living area is open to the kitchen and dining. There are french doors to the back trellised deck toward the Williams River, which acts as the southern boundary of the property. The den, laundry room, powder room and entry boot/coat area complete the first floor. Upstairs there are two nice sized guest rooms filled with natural light, a hall bath and a generous primary suite with walk-in closet. Sited on just under an acre with a tucked in patio adjacent to the well stocked and swimmable river.

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 40 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.

Nestled on a tidy 1.3-acre parcel, surrounded by trees and mature landscaping, this delightful 3-bedroom/2.5-bath home is beautifully maintained and move-in ready. With a well-designed layout that can easily accommodate single-floor living, the main level features a Primary Bedroom with its own heated sunroom and en suite bath. Also on the 1st floor is a 2nd bedroom, a convenient bath, a cozy living room with a wood-burning fireplace, and a sunlit kitchen/dining area which opens onto a splendid south-facing deck. On the 2nd floor is a 3rd bedroom, a large bonus room, a shared full bath, and a practical laundry room. Recent improvements include mini split system, a brand-new roof completed in April 2024, and many updates throughout. The well-groomed back yard features an enclosed stone patio tucked on the western side of the house, and a heated barn with a concrete floor stands ready to serve as a garage, workshop, or studio. Square footage includes heated sunroom. Septic system is designed for 3-bedrooms. This property is serviced by Housatonic Water Company. Owners have not had any problems with the water.

Delightful single-family home, beautifully maintained and updated, on 2 acres of land. Featuring four spacious bedrooms, two full bathrooms, and a newly updated (2017) eat-in kitchen and dining room. The first floor features two bedrooms, including a handicap-accessible bathroom and laundry area.The second floor offers two large bedrooms with a full bathroom and a large walk-in closet. Nice living room with sliding doors leading you to the backyard oasis with magnificent views to relax and enjoy. Beautiful hardwood floors throughout. Energy efficient natural gas heating system and hot water. Two car detached garage with ample off-street parking. Roof was replaced in 2015. This is a terrific opportunity to work remotely. Live and work in this convenient location within minutes to town center, restaurants, bus line, skiing, hiking and all the wonderful attractions the Berkshires have to offer.

Don't miss this move-in ready cabin on 1 acre, just a short walk to downtown Great Barrington and Lake Mansfield's lovely beach. Gaze at breathtaking city and distant mountain views from your spacious living room with vaulted ceilings and a stunning free-standing stone gas fireplace. The open kitchen features an eat-in area and deck access for grilling. Enjoy one level living w/ a primary suite on the first floor. A half bath w/laundry complete the main level. Upstairs, two bedrooms boast tall ceilings and windows looking out onto trees & letting in natural light. The bonus loft area has the best view in the house! Ample storage in the partially finished basement and heated two-car garage. Impressive short term rental history. Enjoy quick access to ALL Berkshire attractions! A must see!

EXCEPTIONAL LIVE/WORK OPPORTUNITY. This mixed-use building perched above the Housatonic River offers the opportunity to be part of the growing Bridge Street commercial corridor. Just up the street from the Berkshire Co-op, and steps from the future site of an 88 room boutique hotel, this property is an investment in the ''boom town'' of the Berkshires. The first floor has office space currently rented by an architectural firm. There is a full bath for office use. Upstairs, there is more office space used by the architectural firm, as well as a 700+ square foot one bedroom, one bath apartment. The apartment is accessed by a staircase at the rear of the building. The tenants enjoy a deck with views of the Housatonic River. Walking distance to Main Street. Parking for 8+ cars.

Escape to the serene countryside, where this stunning New England farmhouse beckons with its picturesque setting on 10 acres. This property boasts a pool, pool house, garage and barn, offering endless possibilities for enjoyment and relaxation. Step inside this beautifully renovated home, where modern amenities blend seamlessly with classic charm. The 4 bedrooms and 3.5 baths provide ample space for comfortable living. This home is sure to impress with its impeccable design and attention to detail. Outdoor living is a true delight at this property, with plenty of space to roam and explore. The in-ground pool is a refreshing spot to cool off, while the pool house provides a convenient place to relax and unwind. The garage and barn offer storage space for all of your outdoor essentials.

EIGHT BUILDING ESTATE COMPOUND for discriminating buyers on quiet country road. THREE PARCELS COMBINED. created exclusively with custom, high-end designer elements & imported materials in 2021-22. #71: MAIN HOUSE features 3 BRs, 2 1/2 baths, tiled fireplace, first floor primary BR, Club House/Guest House w/kitchen (no stove), living room, loft office or BR, extensive landscaping, heated gunite pool, pickleball court. Pink House: office/playhouse. #67: UNDER CONSTRUCTION: 6,000+/- POST & BEAM luxury 3-level, 3-BR home with inground pool & 2-BR Guest House. UNIQUE SANCTUARY w/Indonesian tub, fountain, antique fireplace, jeweled floor, koi pond.#73 GUEST HOUSE: Custom 3-BR 1 bath retreat over 3 bay garage. CLOSING PREFERRED IN OCTOBER. SEPTEMBER 27 WEDDING CONFIRMED.

INCREDIBLE OPPORTUNITY TO FINISH A 3-LEVEL, 6,000 SQUARE FOOT BERKSHIRE DREAM HOME ON 16 PRIVATE ACRES WITH TWO-BEDROOM GUEST HOUSE. ***FIRST PHOTOS SHOWN ARE AN EXAMPLE OF A FINISHED HOME OF SAME DESIGN BY Woodhouse Timber Frame Company. ***CONSTRUCTION IN PROGRESS*** Completed: Surveys, land clearing, driveway installed, underground utilities, well, septic, house plans, building permits, privacy berm, foundation, framing, roughed-in plumbing, electric and propane heat, inground pool foundation, floor plans for 3 bedrooms, 4 baths, 2 kitchens, 2 family rooms, attached 2-car garage. GUEST HOUSE: With interior plans for 2 bedrooms, LR, kitchen, and bath over 2-bay garage.

INCREDIBLE OPPORTUNITY TO FINISH A LUXURY BERKSHIRE HOME & GUEST HOUSE ON 16 PRIVATE ACRES. ***PICTURES SHOWN ARE AN EXAMPLE OF A FINISHED HOUSE. ***CURRENT HOUSES UNDER CONSTRUCTION*** Designed by Woodhouse Timber Frame Company. 3-LEVEL 6,000+/- sq. ft. POST & BEAM house, 2-bay attached garage, elevator, cupola, VIEWS, inground pool. Lower level SECOND KITCHEN, family rm, fireplace. COMPLETED SITE WORK: Land clearing, underground electric, new well, septic, building permits, driveway, foundation, timber package, pool, foundation, surveys, electric, roughed-in plumbing, PLUS FRAMED 2-BR GUEST HOUSE OVER 2-CAR GARAGE. UNIQUE OCTAGONAL TIMBER FRAME SANCTUARY: Copper roof, Indonesian tub/fountain, jeweled flooring, custom tile, antique fireplace, nickel soaking tub, black iron fencing.

NEWLY RENOVATED ESTATE COMPOUND for discriminating buyers on a quiet country road. TWO PARCELS COMBINED. This must-see, 7-building property was created exclusively with custom, high-end designer elements and imported materials in 2021-22. #71: MAIN HOUSE features 3 bedrooms, 2 1/2 baths, tiled fireplace, first floor primary BR, Club House/Guest House w/ kitchen (no stove), living room, loft office or BR, Pink House: office, doll house, extensive landscaping, heated gunite pool, pickleball court. #67: UNDER CONSTRUCTION: 6,000+/- POST & BEAM luxury 3-level, 3-BR home with inground pool and 2-BR Guest House privately set in the woods, UNIQUE TIMBER FRAME SANCTUARY w/Indonesian tub/fountain, antique fireplace, jeweled floor, koi pond.

Walk to water roughly 500' to private Lake access. Leave your kayaks and canoes for season. Swim and relax at Lake's edge. One street back from Lakefront. Come preview this warm cozy cottage that's move in ready also to include most furnishings. Includes Laundry room. Some views of lake. Separate 1 car garage. Deck to enjoy summer barbecuing. Easy maintenance. Title 5 is passing. Year round living.

Enjoy the charm of this cozy country home, ready for you to move in. The rooms have been freshly painted and the carpets are new. The knotty pine walls create a warm and inviting atmosphere. The basement is heated and can be used as extra living space. You can also access the beautiful backyard from the lower level, where you can admire the stunning sunsets and mountain views and sip wine next to the babbling brook. The property is surrounded on 3 sides by the Goodnow Preserve - protected land.

Recently renovated 2-3 bedroom, 1 new full bath and one half bath in move- in condition! Outside newly painted! Two car garage! Lovely yard with mature gardens! Living room with wood burning fireplace and vaulted ceiling! 1st. floor office or bedroom! 2nd. floor has 2 bedrooms and a new full bath with shower and soaking tub! Great enclosed front porch to enjoy the sun filled days!

A stylish and bright 4 bedroom, 3 bath private yet convenient home, located at the top of a sweeping drive. The traditional exterior belies a fresh, contemporary, open first floor while retaining a dedicated dining room that would also make a terrific den or office. A very large screened porch and a sunny deck reached from the great room expands the summer footprint to allow for large gatherings and appreciation of the landscaped property of over five acres. All bedrooms are located on the second floor - an en-suite primary, three guest bedrooms and a renovated bath. An attached two-car garage is nearby a powder room. There's loads of closet space and dry storage in the clean, full basement. Just a five minute drive into the center of town. Furnishings are available outside of escrow.

Nestled amidst the picturesque embrace of Great Barrington, where the harmonious blend of nature and small-town charm unfolds, The Laurel beckons you into a realm of opulence and refinement. As you step inside, a grand two-story glass atrium lobby welcomes you with a breathtaking display of contemporary design and lavish furnishings. Lush plants and waterfalls adorn the walls, seamlessly integrating the surroundings of the natural world. This luxurious three-story residential enclave comprises 30 condominium units, including 13 one-bedroom and 17 two-bedroom residences. The units offer breathtaking mountain-views with private balconies or secluded terraces, providing optimal space for both entertainment and tranquil relaxation.