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24 Photos
DONOVAN REAL ESTATE
$495,000
3 BD | 2 BA
Residential - Single Family

Custom-built Contemporary is ready for its second owner! Perfect blend of comfort, privacy and natural beauty on 9.7 acres. Meander on the 9.7 acres with a babbling brook that is heard from the front porch. there are distant mountain views, not visible from the house. The main floor features a kitchen with cabinets galore and a wine refrig, cathedral ceiling in the dining room with a fireplace, generous size living room with views to the outside, two bedrooms and a bathroom. The second floor features a generous size bedroom with a private bathroom and an open sitting area that could function as a study. The kitchen and bathroom were updated 14 years ago, approximately. The seller is installing a new septic.


61 Photos
BISHOP WEST REAL ESTATE
$495,000
2 BD | 3 BA
Residential - Single Family

Welcome to this well-maintained home on the doorstep of Williams College and downtown Williamstown. This inviting 2-bedroom, 2.5-bath home offers 1,909 square feet of flexible living space where natural light, historic charm, and thoughtful updates create a cozy retreat with room to make it your own. The spacious kitchen offers stainless steel appliances and a convenient mudroom entry into the home from the recently installed driveway, which provides easy maintenance and improved drainage. Flexible spaces make it easy to adapt the home to your lifestyle. In addition to two bedrooms, a downstairs office, an upstairs bonus room, and the renovated third-floor provide options for working from home, a reading nook, creative pursuits, or guest accommodations.


22 Photos
STONE HOUSE PROPERTIES, LLC
$495,000
3 BD | 3 BA
Residential - Single Family

Restoration Ready! Set along a beautiful country road in Sheffield, this charming eyebrow Colonial offers three bedrooms, two and a half baths, and lovely views off the back. Original details throughout reflect the home's history and character, complemented by a welcoming front porch, distinctive bay window and classic New England lines. Conceptual renovation plans illustrate the potential for inviting living and dining spaces, a separate den and outdoor areas to enjoy the setting. A wonderful opportunity to bring your vision to a Berkshire home with enduring charm and so much possibility. Additional land available.


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ENGEL & VOLKERS WELLESLEY
$495,000
2 BD | 1 BA
Residential - Single Family

Near Lee and Lenox, this Berkshires waterfront cottage offers two bedrooms and a full bath on the main level, plus a bonus room in the lower-level walkout. An open floor plan--kitchen, dining, and living--opens to a screened-in porch with western views over Little Robin Lake. Enjoy the quiet of this no-motor lake: kayak, swim off your dock, or fish until sunset. Evening dinners or a glass of wine belong on the expansive lower stone patio. A gentle slope leads to lake access and an expansive shoreline--ideal for a fire pit and s'mores--plus an attached garage for winter storage of boats and water gear. Hike October Mountain State Forest and Becket Quarry, ski Otis Ridge or Canterbury Farm, and reach Lee and Lenox restaurants, Tanglewood, and Jacob's Pillow in minutes.


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WILLIAM RAVEIS - BERKSHIRE

This is the private, lush, estate property with 23 acres, and the opportunity for additional lots, that you have been waiting for! A gorgeous gentle sweep brings you to distant ridge views. The large open clearing is ready and (originally) perc-tested and passed. 7 acres of rich hardwood forest, and two established stone entrances open in from Cross Rd and the other on Leffingwell. Equestrian or hobby farm potential, perfect for a family compound, or just build your dream home and enjoy the space around you!


57 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$495,000
4 BD | 3 BA
Residential - Single Family

Step back in time at this remarkable 1768 antique Colonial set on approximately 7 acres in scenic Blandford. Formerly the Baird Tavern, was the home for the family for many years and more recently it was used as a bed and breakfast. Rich with character and historic charm, this 4-bedroom, 2.5-bath home offers approximately 2,920 square feet of living space, featuring original post-and-beam construction, wood and pine flooring, and three fireplaces. The property offers an exceptional opportunity for those seeking space, privacy, and the potential for a hobby farm or equestrian use, with a barn/stable, storage shed, and horses permitted. A new septic system with Certificate of Compliance to be installed prior to closing.


27 Photos
COMPASS MASSACHUSETTS , LLC GB
$495,000
3 BD | 2 BA
Residential - Single Family

Set on two-thirds of an acre in a residential area, walkable to all Great Barrington has to offer, this versatile home offers 4+ bedrooms and 3 bathrooms. The main floor boasts two bedrooms, a dedicated office or guest space, one and a half baths, laundry, as well as the main living, dining, and kitchen areas. Upstairs you will find 2 additional bedrooms and another half bath. Wood-burning fireplace, exposed beams, hardwood floors, and a spacious three-season porch overlooking the stone patio all make this property a must-see. The lot offers a large yard as well as the patio, a two car garage and an additional outbuilding.


13 Photos
ALTON & WESTALL REAL ESTATE AGENCY, LLC
$495,000
5 BD | 4 BA
Multi-Family

Don't miss out on this unique investment opportunity in south Williamstown. Two 2-family properties being sold together at less than assessed value. #25 New Ashford consists of 1,820 sq.ft. with 2 one-bedroom, one-bath units, a porch and a full basement. #29 New Ashford consists of 2,016 sq.ft. with a two-bedroom, one bath unit, a one-bedroom, one bath unit and shared laundry in the common area.


36 Photos
COMPASS MASSACHUSETTS , LLC GB
$499,000
6 BD | 2 BA
Multi-Family

Duplex in the hills of Housatonic. Three bedroom, one bathroom on each side. Enclosed front porches and open back porches, large garage, all on a corner lot. Located on the Grove St turn overlooking the village of Housatonic and only a few short steps from the Flag Rock conservation area, this is both in town and in a lovely mountain setting. Both units have large walk-up attic and basement spaces. On-site laundry, updated heating system and electrical, newer roof, and solar. This home is an excellent owner-occupied or investment opportunity. One side currently vacant.


36 Photos
COMPASS MASSACHUSETTS , LLC GB
$499,000
6 BD | 2 BA
Residential - Single Family

Duplex in the hills of Housatonic. Three bedroom, one bathroom on each side. Enclosed front porches and open back porches, large garage, all on a corner lot. Located on the Grove St turn overlooking the village of Housatonic and only a few short steps from the Flag Rock conservation area, this is both in town and in a lovely mountain setting. Both units have large walk-up attic and basement spaces. On-site laundry, updated heating system and electrical, newer roof, and solar. This home is an excellent owner-occupied or investment opportunity. One side currently vacant.


5 Photos
BERKSHIRE HOMES AND CONDOS

Opportunity to complete this renovation.Extensive site work has already been completed. $25,000 of Tree removal in 2022, kerosene tank removal in 2022, New Septic system designed and installed in 2023, Asbestos Remediation in 2025, New roof with new 3/4 plywood board in 2025, Installed 3 new remote controlled skylights in 2025, 3 more trees removed in 2025, U-driveway installed in 2025. Deeded Lake Rights and private beach for Owners Only. House is directly across from the path to the beach. Goose Pond is noted to be one of the cleanest lakes in Massachusetts. Finish this renovation or add a foundation of build year dram home in this highly sought after Lake Community.


45 Photos
MACCARO REAL ESTATE
$499,000
2 BD | 3 BA
Residential - Single Family

Turn-key Berkshire retreat! Beautifully renovated throughout, this contemporary chalet feels like a brand-new home. Cathedral ceiling, abundant windows, and an open concept living, dining and kitchen area create a bright, inviting atmosphere. The main level features a primary bedroom with an en-suite bathroom, plus a convenient half bath with laundry hook-ups. The second level offers an open loft, overlooking the main living area, complemented by an additional bedroom and full bathroom. A finished walk-out lower level provides wonderful space for recreation, family room or guests. Enjoy the spacious deck in this natural setting with intermittent stream and no HOA! Convenient to Jacobs's Pillow, Tanglewood and the Berkshires cultural and recreational venues, with easy access to I-90.


42 Photos
SKYTOP ASSET MANAGEMENT

Turnkey office and flex building with detached four-bay garage available for sale or lease at 326 Springside Avenue in Pittsfield. 2,367 SF of finished first-floor office space plus a full lower level, located on a corner parcel with 10 parking spaces. Includes a ±960 SF four-bay garage, new roof, and standby generator. Flexible B-G zoning. Rare combination of professional office, on-site storage, and drive-in garage on a single site. Ideal for owner-users, professional firms, contractors, or light flex users. Available immediately. Full details, floor plans, photos, and Matterport 3D tours: https://326springsideavenue.com


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PREFERRED COUNTRY PROPERTIES
$499,000
3 BD | 2 BA
Residential - Single Family

NEW TO MARKET. Immaculate mid-century home on coveted Payn Avenue in Chatham Village NY. Rarely do homes in this neighborhood come available. Established, quiet, and family-friendly. Memorial Fields recreational area, shopping, schools within a half-mile. Central A/C and hardwood floors throughout incl parquet kitchen. 3BR/2BA (3rd BR currently laundry rm), LR w/FIREPLACE, large dining area off user-friendly modern kitchen. Primary BR w/primary bath. Glass sunroom overlooks the fully fenced, large backyard ideal for large gatherings. Solid covered canopy great for BBQing or reading in the warm breeze. Add'l lot included for a total .67 acre. Attached 2-car garage, full basement and paved driveway among amenities. 1 mile to Taconic Parkway. Owners relocating; home I


10 Photos
360BERKSHIRE REALTY GROUP

Commercial property located at 4 way lighted intersection. Directly across the street from MASS MoCA. Close proximity to downtown North Adams and the Porches Inn. Marshall Street Traffic Count: 6904


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BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD
$499,900
3 BD | 4 BA
Residential - Single Family

Sitting atop of scenic Florida Mountain, this custom built Cape with elegant charm features 3 Bedrooms, 3 Full and 2 half Baths and central A/C.The Primary suite is located on the first with a fireplace, large walk-in closet and a private sitting room to relax in. The Primary Bath features a 3 head walk-in shower, Jet tub, water closet and radiant heat tile floors. The Bedrooms on the second floor each have their own Full Bath separated by a long walkway with a balcony overlooking the living room. A floor plan that flows from room to room with ease. The living room has a cathedral ceiling, custom fireplace and wood elevator. The Kitchen features a commercial stove, built-in oven and granite counters. A Bonus Room with half Bath over the heated 2 car garage. Walk-out basement.


50 Photos
LAMACCHIA REALTY, INC
$499,900
4 BD | 3 BA
Residential - Single Family

Discover refined Berkshire living in this exceptional 4 bedroom, 3 bathroom end unit townhouse with Mount Greylock views. Meticulously renovated from top to bottom, this turnkey residence offers an effortless flow, spacious rooms, and high end finishes throughout. The elegant interior features beautiful cabinetry, quartz countertops, marble clad bathrooms, and energy efficient features. Spacious bedroom suites offer luxurious suite bathrooms and abundant closet space, complemented by a dedicated office. Set between Williamstown and Lenox, enjoy easy access to MASS MoCA, the Clark Art Institute, lakes, rivers, hiking, waterfalls, and the best of Berkshire living, with convenient travel to Boston and New York City.


37 Photos
BERKSHIRE LISTINGS
$499,900
3 BD | 2 BA
Residential - Single Family

3.21 Acres - Two Garages plus a Full Walkout Basement! This beautifully maintained 1,900 sq. ft. ranch offers comfortable single-level living with a bright, open floor plan and plenty of natural light. An inviting kitchen features marble countertops, while beautiful hardwood floors and a custom fireplace add warmth and character throughout. The spacious walkout basement includes a Smith furnace and Fire Chief wood stove, providing flexible heating options. Set back from the road and abutting Crystal Pond, this peaceful private setting is the perfect place to enjoy the beautiful fall season. Property features two garages, two driveways, a barn, ample parking, and hookups for a future hot tub. Conveniently located just 34 minutes to Westfield, 19 minutes to Lee, and 26 minutes to Pittsfield.


39 Photos
PAULA MCLEAN REALTORS INC.
$499,900
3 BD | 3 BA
Residential - Single Family

Fall in Love with Berkshire Living! Welcome home to this charming 3-bed, 2.5 bath Colonial, perfectly situated on just under ½ acre and surrounded by the beauty of the Berkshires. With 2,138 square feet of living space, this home is ready to welcome you for crisp autumn mornings, cozy evenings. The Kitchen is light, bright, and welcoming, featuring stainless steel appliances, granite countertops, and a beautiful eat-in area that is just right for morning coffee, weekend brunch, or an afternoon cocktail while enjoying the changing seasons. Gather everyone around the table in the formal dining room, where holidays, family dinners, laughter, and new memories are waiting to happen. The living room ...


40 Photos
NON-MEMBER / RECIPROCAL
$499,900
3 BD | 2 BA
Residential - Single Family

Discover this spacious, updated home offering year-round recreation just around the corner from Otis Reservoir, Massachusetts' largest recreational lake. Enjoy an open floor plan, a modern kitchen and a quiet yard for outdoor fun just minutes from your association dock and storage locker. Features include a main floor primary bedroom with a full bath, plus two large upstairs bedrooms with a second full bath. The property's location offers easy access to swimming, boating, skiing, snowmobiling, and hiking. This turn-key retreat is ready for you to start making memories as you relish the ultimate blend of modern comfort and natural beauty!

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