Berkshire County MA Homes under $500,000

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  /40

  $499,000

  • 6 Beds
  • 2.5 Baths
  • 3,184 Sq Ft

  119 S Main St, Sheffield, MA 01257

  A unique opportunity to make this terrific property your own, with a separate bungalow apartment for income or other home business uses. Property features a 6 bedroom, 2 bath 1880's Victorian with a classic yet casual style. First floor features a sunny living room, large country kitchen, formal dining room w/ built-ins, and front parlor/bedroom. Second floor offers 5 bedrooms, 2 full baths, and

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 481-1637

  119 S Main St, Sheffield, MA 01257
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  /6

  $425,000

  • Land
  • 3.30 Acres
  • $128,788 per Acre

  9 Wheatleigh Dr, Stockbridge, MA 01262

  RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

  

  Selina Lamb

  Birch Properties

  (413) 343-5283

  9 Wheatleigh Dr, Stockbridge, MA 01262
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  /6

  $425,000

  • Land
  • 3.30 Acres
  • $128,788 per Acre

  9 Wheatleigh Dr, Stockbridge, MA 01262

  RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 722-5098

  9 Wheatleigh Dr, Stockbridge, MA 01262
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  /32

  $469,000

  • 3 Beds
  • 3 Baths
  • 1,849 Sq Ft

  11 Bangor St, Lanesborough, MA 01237

  Welcome to your dream home! This beautifully constructed 3-bedroom, 3-bathroom residence offers modern living with deeded right of way to serene Pontoosuc Lake. Built in 2023, the home blends style, comfort, and functionality across two spacious levels.The upper level boasts 1,344 sq. ft. of thoughtfully designed living space, featuring an open-concept kitchen with granite countertops, stainless

  

  Kellie Perrault

  NOCHER REALTY

  (877) 330-5991

  11 Bangor St, Lanesborough, MA 01237
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  /28

  $495,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  36 Castle Ln, Great Barrington, MA 01230

  Charming Renovated Cottage on The Hill - Great Barrington, MADiscover this beautifully renovated Four Square-style cottage in the heart of Great Barrington's coveted ''The Hill'' neighborhood--a rare pied-a-terre offering classic charm with modern upgrades. This delightful 2-bedroom home is nestled in the Southern Berkshires, just moments from downtown, Lake Mansfield, and preserved natural

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 414-5590

  36 Castle Ln, Great Barrington, MA 01230
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  /16

  $485,000

  • 8 Beds
  • 6 Baths
  • 8,543 Sq Ft

  153 First St, Pittsfield, MA 01201

  Looking to add a well-performing asset that provides you with income from day one? This six-family investment property offers investors immediate cash flow and upside potential... sitting at a 11 cap rate, this property offers a strong return on investment with room to grow based on some under market rents! This property offers a range of studio to 3-bedroom units and Off street parking.

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 728-1773

  153 First St, Pittsfield, MA 01201
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  /47

  $499,900

  • 4 Beds
  • 2 Baths
  • 2,414 Sq Ft

  236 Summer St, Lanesborough, MA 01237

  Welcome to 236 Summer Street, a charming Cape-style home nestled in the picturesque town of Lanesboro, MA. This delightful property features 4 spacious bedrooms and 2 full baths, perfect for family living, the possibility of single level living and an attached 2 car garage. Set on 2.2 park-like acres, you'll enjoy the tranquility of nature right at your doorstep. The expansive grounds offer

  Doug Collins LAMACCHIA REALTY, INC

  236 Summer St, Lanesborough, MA 01237
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  /57

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,360 Sq Ft

  1501 W Center Rd, Otis, MA 01253

  Nestled along a tranquil, private country road, this well-maintained home offers a perfect blend of rustic charm and modern comfort. The open and airy living spaces are bathed in natural light, with a vaulted ceiling in the living room that creates an expansive, welcoming feel. The cozy wood stove adds warmth and character, making it an ideal spot for chilly nights.This home features a main-floor

  Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

  1501 W Center Rd, Otis, MA 01253
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  /42

  $495,000

  • 3 Beds
  • 2 Baths
  • 1,376 Sq Ft

  46 Cobble View Rd, Williamstown, MA 01267

  Impeccably maintained 3-Bedroom, 2-Bathroom Ranch. This beautifully cared-for, one level home offers the perfect mix of comfort, convenience, and quality. Located close to downtown & Williams College, the property features a private backyard and an expansive deck with dual slider access--ideal for easy entertaining or relaxing outdoors. Inside, enjoy beautiful wood floors, efficient mini-split

  Erin Scott BURNHAM GOLD REAL ESTATE, LLC

  46 Cobble View Rd, Williamstown, MA 01267
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  /41

  $479,900

  • 4 Beds
  • 2 Baths
  • 2,197 Sq Ft

  33 Eleanor Rd, Pittsfield, MA 01201

  Updated Colonial in desirable West Pittsfield w/ deeded lake rights & private Onota Lake access. Featured in The Boston Globe's ''8 Berkshire Homes near Ski Resorts,'' it is just 4.6 miles from Bousquet Mountain. This spacious home offers 4 bedrooms, 2 baths, & a refreshed kitchen w/ new flooring, backsplash, lighting, & soft-close cabinets. The 1st floor bath was renovated w/ a new vanity,

  THE KAHN TEAM BISHOP WEST REAL ESTATE

  33 Eleanor Rd, Pittsfield, MA 01201
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  /56

  $499,900

  • 3 Beds
  • 2 Baths
  • 1,218 Sq Ft

  100 Church St, Lee, MA 01238

  Welcome to this warm and inviting ranch-style home nestled in the heart of the Berkshires! This inviting property features 3 bedrooms, 2 full bathrooms and a comfortable layout ideal for everyday living and entertaining. This unique property includes a separately deeded lot presenting endless possibilities that sets this property apart. Whether you value privacy and space or want room to grow and

  Lisa Kelley MACCARO REAL ESTATE

  100 Church St, Lee, MA 01238
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  /33

  $489,900

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft

  193 Cold Spring Rd, Williamstown, MA 01267

  Welcome to this beautifully maintained 4-bedroom, 2-bath home that is truly move-in ready! With its charming vinyl siding, spacious 3.5-car garages, and inviting large porch, this property offers curb appeal and practicality in equal measure. You'll also find a bright and airy sun room, ideal for relaxing, entertaining, or enjoying your morning coffee in any weather. Step inside to find freshly

  Suzette Lyons BURNHAM GOLD REAL ESTATE, LLC

  193 Cold Spring Rd, Williamstown, MA 01267
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  /33

  $489,900

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  59 Joan Dr, Pittsfield, MA 01201

  Welcome to 59 Joan Drive, a stunning 4-bedroom, 2.5-bath raised ranch located in one of Pittsfield's premier neighborhoods. This inviting home features a spacious open floor plan, perfect for both relaxation and entertainment. The main level boasts a bright living room, a modern kitchen with ample storage, and a dining area that opens to a spacious wrap around deck, ideal for outdoor gatherings.

  Doug Collins LAMACCHIA REALTY, INC

  59 Joan Dr, Pittsfield, MA 01201
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  /44

  $484,900

  • 4 Beds
  • 2 Baths
  • 2,606 Sq Ft

  133 Pomeroy Ave, Pittsfield, MA 01201

  Prestigious grand colonial located in the lovely Southeast area. This home has been meticulously maintained. Four large bedrooms, formal living room with fireplace, Glass doors leading out to a pergola, A family room, dining room, renovated kitchen , den or office could be a fifth bedroom. One upstairs bathroom renovated and one on the first level,The landscaping is a gardener's dream come

  Cheryl Wendling BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  133 Pomeroy Ave, Pittsfield, MA 01201
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  /55

  $469,900

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  94 Gale Ave, Pittsfield, MA 01201

  This 3 bedroom 2 1/2 bath split level ranch is looking for its second owner! Enter the first floor and walk into big living room, that flows into gorgeous custom kitchen with big island, granite counters, natural gas cooking, 2 sinks, and then continues into Dining room! 1st Floor has Primary Bdrm, with bath, with walk in shower, big tub, and custom vanity w/built in upper cabinetry, 2 more

  Susan Colvin MONARCH REALTY, INC.

  94 Gale Ave, Pittsfield, MA 01201
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  /35

  $468,000

  • 2 Beds
  • 1 Bath
  • 660 Sq Ft

  25 Pine St, New Marlborough, MA 01230

  LAKE LIVING DONE RIGHT! Year round retreat in the Lake Buel Community. Thoughtfully designed spaces, cozy & unpretentious. The living area, comfortable for family & guests, has vaulted ceiling and Gas Fireplace, making this home just as inviting in the cooler months. Kitchen is functional, attractive and updated. Simple lines, wainscoting, wood floors, ductless A/C units. The Sunroom is perfect

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  25 Pine St, New Marlborough, MA 01230
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  /67

  $474,900

  • 3 Beds
  • 1.5 Baths
  • 1,456 Sq Ft

  47 Gale Ave, Pittsfield, MA 01201

  Exceptional opportunity: Fully renovated three-bedroom main residence with guest cottage...FULL DELEADING COMPLIANCE!!! This special property offers owner-occupied living and additional income. The fully renovated main residence with the separate guest cottage provides ample space for various living arrangements. Both homes are move-in ready!

  Brandon White COHEN & WHITE ASSOCIATES

  47 Gale Ave, Pittsfield, MA 01201
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  /38

  $475,000

  • 3 Beds
  • 4 Baths
  • 3,298 Sq Ft

  1271 Main Rd, Savoy, MA 01256

  Impeccably kept 3 bedroom home originally built in the early 1900's with updates including a new addition in 1989. Enjoy the convenience of being on Main Rd yet relax with an expansive 5.8 acre backdrop for your privacy. Plenty of space for entertaining with a massive living room with adjoining deck overlooking the grounds. Primary bedroom wing above and second ensuite compliment the newer

  Shawn Flaherty WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  1271 Main Rd, Savoy, MA 01256
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  /35

  $475,500

  • 4 Beds
  • 2.5 Baths
  • 2,140 Sq Ft

  149 Kittredge Rd, Pittsfield, MA 01201

  Beautifully renovated home with plenty of space for everyone. This home offers 4 bedrooms, 2.5 baths, and a huge yard. Fully finished walkout basement adds another living room, 1⁄2 bath, and 4th bedroom.

  Tanya Shepardson Lamacchia Realty, Inc.

  149 Kittredge Rd, Pittsfield, MA 01201
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  /31

  $475,000

  • 3 Beds
  • 1 Bath
  • 1,114 Sq Ft

  309 Tamarack Trail, Sandisfield, MA 01255

  Rustic Contemporary in Otis Wood Lands that abuts the State Forest! This cozy home has an open concept kitchen/living/dining area with vaulted ceilings. Access the screened-in porch and deck from the sunken living room. Primary bedroom with skylight and deck access. Detached two-car garage with storage above. An easy-to-maintain property. Association amenities include tennis/pickleball

  Emily Piacquadio LANCE VERMEULEN RE, INC

  309 Tamarack Trail, Sandisfield, MA 01255
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  /10

  $485,000

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft

  26 Manville St, Great Barrington, MA 01230

  Modernized 3-bedroom 2-bathroom Cape home on quiet dead-end street located in a fantastic in town neighborhood. Recently renovated, the kitchen features granite countertops, subway tiles, modern fixtures, and wood floors. Downstairs offers a dining room with wood floors, large living room with wood burning fireplace, two bedrooms, and a full bathroom that boasts more of that classic black and

  David Carlson FAIRGROUND REAL ESTATE, INC

  26 Manville St, Great Barrington, MA 01230
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  /9

  $425,000

  • Land
  • 2.00 Acres
  • $212,500 per Acre

  11 Rowe Rd, Great Barrington, MA 01230

  Privacy and big potential! Build your Berkshire dream home in the quiet Alford hills on this 2 acre parcel surrounded by trees. Foundation for a new home is already built with architectural plans included as an added bonus. The property includes a new septic system and well, plus 1 outbuilding and additional barn at the back of the property.

  John Segalla HOUSATONIC REAL ESTATE

  11 Rowe Rd, Great Barrington, MA 01230
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  /43

  $450,000

  • 1 Bed
  • 1.5 Baths
  • 1,287 Sq Ft

  160 Water St Unit 114, Williamstown, MA 01267

  Cable Mills consists of three former industrial mill buildings restored into beautiful homes featuring 12ft to 16ft tall ceilings, massive windows, and exposed brick and beam, steel and timber throughout, stainless steel appliances, granite countertops, gas-fired ranges, generous closets and in home laundry. Cable Mills offers stunning views of the famed 'Purple Mountains' and the rolling Green

  StreamLine Communities STREAMLINE COMMUNITIES

  160 Water St Unit 114, Williamstown, MA 01267
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  /28

  $485,000 Open Sat 12PM - 1:30PM

  • 3 Beds
  • 2.5 Baths
  • 1,444 Sq Ft

  1 Stanley Dr, Great Barrington, MA 01230

  Unique Town House that stands alone! Nicely maintained unit with first floor Bedroom & updated Bath. Upstairs two Bedrooms share a full bath. Spacious deck overlooks a private yard bordered by woods for total privacy. The attached garage affords plenty of extra storage. Nicely landscaped and conveniently located. Minutes to skiing and Shops. Perfect for full time living or as a vacation home.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  1 Stanley Dr, Great Barrington, MA 01230
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  /14

  $435,000

  • 6 Beds
  • 3 Baths
  • 3,016 Sq Ft

  672 N Hoosac Rd Unit 676, Williamstown, MA 01267

  Fantastic opportunity in desirable Williamstown! This charming three-unit multi-family sits on a spacious lot. Each unit offers comfortable living space with solid rental history. The large lot provides off-street parking, green space, or potential for future expansion (buyer to verify). Enjoy beautiful mountain views that add to the property's charm. A rare find--don't miss out!

  Alyssa Sherman MORESI REAL ESTATE PARTNERS

  672 N Hoosac Rd Unit 676, Williamstown, MA 01267
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  /29

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 1,538 Sq Ft

  208 Main St, Lee, MA 01238

  Prime Downtown Lee Investment Opportunity Located on a highly visible corner lot in the heart of downtown Lee, this versatile three-unit building offers a blend of residential and commercial income potential. The property includes two residential units--currently operated as successful short-term rentals--and one commercial space currently leased to a massage therapist. The first-floor efficiency

  Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  208 Main St, Lee, MA 01238
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  /34

  $419,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  220 Theresa Terrace, Lee, MA 01238

  Welcome to this charming raised ranch in the heart of Lee, Massachusetts! This home features beautiful hardwood floors, central AC and spacious bedrooms, providing a cozy Berkshires living experience. Enjoy a great backyard, perfect for relaxation and entertaining. Ideally located near cultural attractions like Jacob's Pillow and Tanglewood, as well as downtown and fantastic restaurants, this

  Andreea Duta BISHOP WEST REAL ESTATE

  220 Theresa Terrace, Lee, MA 01238
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  /32

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,931 Sq Ft

  16 Windflower Way, Williamstown, MA 01267

  Welcome to this charming, freshly painted throughout and carpeted, 3-bedroom, 2 -bathroom condominium located in the desirable Greylock Village. This end unit offers comfort, convenience, and access to a peaceful and picturesque setting in the heart of the Berkshires. Whether you're looking for a full-time residence or a vacation getaway, this property is perfect for all lifestyles. The large

  Kim Burnham BURNHAM GOLD REAL ESTATE, LLC

  16 Windflower Way, Williamstown, MA 01267
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  /37

  $449,000

  • 4 Beds
  • 2.5 Baths
  • 2,015 Sq Ft

  111 North St, Williamstown, MA 01267

  Great Opportunity for Investment Property or residence. Close to Williams College and the center of Williamstown. Has a strong rental record as an active Air BnB or College student rental. Offered completely furnished. Offering four bedrooms, two bathrooms and fully appointed kitchen. Lower level is used as a separated office with private office, storage space, sitting area and half bath.

  Terry Harron-Lamb DOUBLE P GENERAL CONTRACTING AND REAL ESTATE ,LLC

  111 North St, Williamstown, MA 01267
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  /5

  $500,000

  • Land
  • 8 Acres
  • $66,667 per Acre

  71 Miner Lots 2 and 3 Rd, Lanesborough, MA 01237

  An extraordinary opportunity awaits in the heart of the Berkshires. This is not just a parcel of land; it's a launchpad for your dreams. Offering a rare combination of privacy, turn-key potential, and lifestyle flexibility, this 7.5-acre property in Lanesborough is ready for you to create your own private compound or mini-farm.Nestled on a newly paved road just off Route 7, the property features

  Keyla Girard LAMACCHIA REALTY, INC

  71 Miner Lots 2 and 3 Rd, Lanesborough, MA 01237
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  /24

  $495,000

  • 3 Beds
  • 2 Baths
  • 1,375 Sq Ft

  130 West St, Lenox, MA 01240

  LOCATION, LOCATION, LOCATION....Steps to Morris School....minutes to Tanglewood or Main Street for shopping, the library, groceries or dinner! This 3 bedroom 2 bath 1890's home sits on a half acre lot with large fenced area for pets....this home is waiting for your decorating and updating ideas. First floor bedroom, full bath, living room, dining, kitchen and great enclosed rear porch....steps

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  130 West St, Lenox, MA 01240
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  /66

  $449,900

  • 4 Beds
  • 3 Baths
  • 14,371 Sq Ft

  71 Park St Unit 75, Adams, MA 01220

  Large scale 4 Unit commercial property offers four excellent rental opportunities in the heart of downtown's Park Street. The building features two gleaming residential apartments that capture the vibrant city lifestyle, perfect for residents seeking urban convenience. The retail space is expansive and currently vacant on the right side, providing a blank slate for your business or investment

  Jason Nocher NOCHER REALTY

  71 Park St Unit 75, Adams, MA 01220
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  /29

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  308 Lenox Rd, Richmond, MA 01254

  Tucked away in the desirable, low-tax community of Richmond, Massachusetts, this 3-bedroom, 2-bathroom ranch, surrounded by higher-priced properties, offers comfortable single-floor living. The open-concept living area, filled with natural light, includes a recently updated kitchen and features quartz countertops, quality stainless appliances, and ample counter space. The master suite includes a

  William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  308 Lenox Rd, Richmond, MA 01254
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  /43

  $475,000

  • 4 Beds
  • 2 Baths
  • 1,560 Sq Ft

  127 Old Joe Rd, Great Barrington, MA 01230

  Nestled on a quiet country road, this well-kept ranch offers the ease of single-level living with ample space to relax, entertain, and make your own. The home features an inviting floor plan with plenty of natural light and room for upgrades, allowing you to personalize each space to your taste.Enjoy seamless indoor-outdoor living with a large back deck--perfect for gatherings or quiet mornings

  Tony Segalla LANCE VERMEULEN RE, INC

  127 Old Joe Rd, Great Barrington, MA 01230
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  /42

  $465,000

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft

  42 East St, Stockbridge, MA 01262

  Set on 6.4 scenic acres, this classic New England farmhouse captures the timeless spirit of Stockbridge, a town beloved for its rich history and cultural legacy. This 2-bed 2-bath home offers authentic charm, featuring beautiful hardwood floors, a spacious kitchen, family room + 1st floor full bath, and a welcoming front porch that evokes a slower, simpler time. Thoughtful updates include a newer

  Conor Meehan STONE HOUSE PROPERTIES, LLC

  42 East St, Stockbridge, MA 01262
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  /36

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 4,401 Sq Ft

  350 Washington Mountain Rd, Dalton, MA 01226

  Spacious 4 bed, 3 bath ranch, located on Washington Mountain Rd. in Dalton. This beautiful, brightly lit home, with steel I-Beam construction contains: hardwood floors throughout, a fireplace on each level, replacement windows, primary bedroom with bath and double closets and a heated lower level with walkout, ready to be finished. Outdoor amenities include: an additional 24x40 two bay

  Timothy Johnson NOCHER REALTY

  350 Washington Mountain Rd, Dalton, MA 01226
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  /28

  $495,000

  • 4 Beds
  • 4 Baths
  • 3,000 Sq Ft

  16 Forrest St, North Adams, MA 01247

  Turn key Airbnb business or beautiful private home in serene setting above the beaten path. No a thru road to property, so more like a gated community.All furnishings are available, to move right in.

  David White OwnerEntry.com

  16 Forrest St, North Adams, MA 01247
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  /38

  $404,900

  • 4 Beds
  • 2 Baths
  • 1,918 Sq Ft

  16 Revere Pkwy, Pittsfield, MA 01201

  The Parkway neighborhoods of southeast Pittsfield are among the city's most sought-after, prized for their tree-lined streets, classic architecture, and easy access to downtown, parks, and schools. Built in 1930, this well-maintained 4 bedroom, 2 bath home provides everything your family needs, with plenty of space for everyone. The first floor features a large living room, east-facing with

  Stephen Daoust STONE HOUSE PROPERTIES, LLC

  16 Revere Pkwy, Pittsfield, MA 01201
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  /44

  $499,900 Open Sat 11AM - 12:30PM

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  345 Big Bass Ln, Becket, MA 01223

  Nestled between forest and garden in the serene, secluded Crystal Pond neighborhood, this bright and breezy home offers rustic charm, serenity and convenience, & central A/C.The open concept floorplan seamlessly merges the dining, kitchen areas into a vaulted great room that boasts threewalls of windows, and skylights. Two bedrooms, new bath and laundry on the first floor, with a beautiful summer

  Ginger Conner RED HORSE REAL ESTATE, LLC

  345 Big Bass Ln, Becket, MA 01223
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  /41

  $405,000 Open House 8/23

  • 3 Beds
  • 1.5 Baths
  • 1,684 Sq Ft

  18 Andes Rd, Hinsdale, MA 01235

  EXPERIENCE LIFE w/ EXCEPTIONAL OPPORTUNITY to OWN 18 Andes Road, Peru, MA — This RARE Find Charming Lindal Colonial-style Cedar Log Home offering the perfect balance of Rustic Character & Modern Comfort. Nestled on 4.34 private acres with 1,684 square feet, this home includes: 2 cozy BR's & 3rd Master w/ Balcony 1 Full BA w/ tile floors & heat lamps, Convenient 1/2 Bath & Closets throughout.

  Kim Dodge Kim Grant-Dodge

  18 Andes Rd, Hinsdale, MA 01235

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