Berkshire County MA Homes under $400,000

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  /6

  $395,000

  • Land
  • 3.3 Acres
  • $119,697 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
• 

  

  /2

  $300,000

  • 6 Beds
  • 4 Baths
  • 4,136 Sq Ft

  Unlisted Address

  THIS LISTING TO BE SOLD AS PART OF A 11 UNIT PACKAGE: Other properties included are located at 40-42 Henry Ave. Pittsfield, MA 01201 and 27-31 Pleasant St. Pittsfield, MA 01201. Acquire this three multifamily package offered at $920,000. Income & expense and rent roll document available in documents and or upon request.

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 779-3154

  Unlisted Address
• 

  

  

  /24

  $335,000

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  363 Henderson Rd, Williamstown, MA 01267

  Discover the perfect blend of timeless New England character and modern comfort in this beautifully maintained home. Offering three generous bedrooms plus a flexible office or walk-in closet, the residence also features 1.5 thoughtfully updated bathrooms and abundant natural light throughout.An open, flowing floor plan showcases warm wood flooring and creates an inviting space for

  

  Gary Fuls Jr

  RE/MAX Transitions

  (413) 779-8073

  363 Henderson Rd, Williamstown, MA 01267
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  /42

  $319,900

  • 3 Beds
  • 2 Baths
  • 1,646 Sq Ft

  1044 Beaver Pond Meadows, Hancock, MA 01237

  Discover this Berkshires getaway in the private Beaver Pond Meadows community, complete with clubhouse and pool access! Just minutes from Jiminy Peak, this location offers a quieter, more relaxed alternative to Country Village. This fully furnished townhouse boasts a strong rental history and plenty of space to spread out, featuring three bedrooms and a full bath on the first level, a spacious

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (855) 810-0060

  1044 Beaver Pond Meadows, Hancock, MA 01237
• 

  

  /2

  $320,000

  • 6 Beds
  • 4 Baths
  • 3,912 Sq Ft

  40 Henry Ave, Pittsfield, MA 01201

  THIS LISTING TO BE SOLD AS PART OF A 11 UNIT PACKAGE: Other properties included are located at 27-31 Pleasant St. Pittsfield, MA 01201 and 101-103 Lincoln St. Pittsfield, MA 01201. Acquire three multifamily package offered at $920,000. Income & expense and rent roll document available in documents and or upon request.

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 339-3453

  40 Henry Ave, Pittsfield, MA 01201
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  /39

  $325,000

  • 12 Beds
  • 3.5 Baths
  • 4,215 Sq Ft

  292 West St, Pittsfield, MA 01201

  This large residential property offers exceptional income potential in a strong Pittsfield rental market. With 12 bedrooms and 3.5 bathrooms, it supports high-capacity occupancy and steady cash flow. The full basement provides extensive storage and includes areas where two former bathrooms once existed, offering a foundation for future updates. A full standing attic adds valuable expansion

  

  Gary Fuls Jr

  RE/MAX Transitions

  (413) 613-4044

  292 West St, Pittsfield, MA 01201
• 

  

  /30

  $399,000

  • 3 Beds
  • 1.5 Baths
  • 1,753 Sq Ft

  6 Overlook Terrace, North Adams, MA 01247

  Experience the timeless allure of this beautifully updated 1920s Dutch Colonial, where classic architectural integrity meets contemporary luxury. Every detail of this residence has been polished to perfection--from the sleek granite chef's kitchen to the gleaming hardwood floors and the inviting warmth of the wood-burning fireplace. This 3 bedroom, 2 bath house offers a rare and sought-after

  

  Diane Thorson

  WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  (413) 848-7361

  6 Overlook Terrace, North Adams, MA 01247
• 

  /2

  $300,000

  • 6 Beds
  • 3 Baths
  • 2,118 Sq Ft

  27 Pleasant St, Pittsfield, MA 01201

  THIS LISTING TO BE SOLD AS PART OF A 11 UNIT PACKAGE: Other properties included are located at 40-42 Henry Ave. Pittsfield, MA 01201 and 101-103 Lincoln St. Pittsfield, MA 01201. Acquire three multifamily package offered at $920,000. Income & expense and rent roll available under documents or upon request.

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 722-5941

  27 Pleasant St, Pittsfield, MA 01201
• 

  

  /6

  $395,000

  • Land
  • 3.3 Acres
  • $119,697 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
• 

  

  /6

  $325,000

  • Land
  • 21.7 Acres
  • $14,977 per Acre

  0 Sisson Hill Rd Unit 248042, New Marlborough, MA 01230

  21.7 wooded acres on one of South County's ''best-kept-secret'' back country roads, yet just minutes away from Great Barrington, Sheffield and the bucolic villages of New Marlborough. Discover nature, privacy & a unique sense of peace on this rare piece of land. The land has been perc tested, seller will provide final survey prior to closing. Map in documents shows proposed new boundaries for

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 848-6618

  0 Sisson Hill Rd Unit 248042, New Marlborough, MA 01230
• 

  

  /38

  $312,000

  • 3 Beds
  • 1 Bath
  • 1,394 Sq Ft

  36 Pittsfield Ave, Pittsfield, MA 01201

  Step into this charming 3-bedroom, 1-bath home tucked away in the comfortable Allendale Parkway neighborhood. With nearly a half acre of land, it could be your perfect blend of comfort and outdoor beauty.Inside, you'll find 1,394 sq. ft. of freshly painted living space with easy-care laminate floors. The first floor offers kitchen, dining room, and a spacious living room where a large bow window

  

  Mary Smith

  WILLIAM PITT SOTHEBY'S - LENOX

  (413) 628-2060

  36 Pittsfield Ave, Pittsfield, MA 01201
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  /39

  $325,000

  • 12 Beds
  • 3.5 Baths
  • 4,215 Sq Ft

  292 West St, Out-Of State, MA 99999

  This large residential property offers exceptional income potential in a strong Pittsfield rental market. With 12 bedrooms and 3.5 bathrooms, it supports high-capacity occupancy and steady cash flow. The full basement provides extensive storage and includes areas where two former bathrooms once existed, offering a foundation for future updates. A full standing attic adds valuable expansion

  

  Gary Fuls Jr

  Gary L Fuls DBA Re/MAX Transit

  (888) 256-3119

  292 West St, Out-Of State, MA 99999
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  /29

  $365,000

  • 3 Beds
  • 1.5 Baths
  • 1,482 Sq Ft

  153 E Main St, Ashley Falls, MA 01222

  Mid-1960s ranch on a quiet street with nearly 1/2 acre! A perfect family home to settle down in Southern Berkshire County. Semi-finished basement is a huge bonus, plus garage and additional detached barn/workshop. Sunny, spacious and ripe with potential. Some thoughtful updates will be needed -- or move in today and make it yours!

  John Segalla HOUSATONIC REAL ESTATE

  153 E Main St, Ashley Falls, MA 01222
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  /31

  $379,000

  • 4 Beds
  • 3 Baths
  • 2,320 Sq Ft

  74 Washington Ave, North Adams, MA 01247

  Completely renovated 4-bedroom home in North Adams, near MCLA. Newly renovated kitchen and bathrooms with new cabinets, quartz countertops, and all new appliances. New flooring throughout. The first floor offers the kitchen, a full bathroom, an office, a large open living room/dining area, and an entry with beautiful staircase to second floor. The second floor features three bedrooms, a second

  Allison Pacelli PACELLI ZEPKA

  74 Washington Ave, North Adams, MA 01247
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  /46

  $389,000

  • 3 Beds
  • 1 Bath
  • 1,413 Sq Ft

  2801 State Rd, Richmond, MA 01254

  You'll feel right at home in this charming Richmond farmhouse, just minutes from West Stockbridge center and close to everything the Berkshires has to offer. Set on two beautiful, private acres in the historic Richmond Furnace district, this three-bedroom house blends New England charm with modern amenities, including energy-efficient solar panels, newer appliances, and Buderus boiler. The main

  Stephen Daoust STONE HOUSE PROPERTIES, LLC

  2801 State Rd, Richmond, MA 01254
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  /39

  $319,900

  • 4 Beds
  • 2.5 Baths
  • 1,540 Sq Ft

  19 Fairgrounds Ave, North Adams, MA 01247

  Tastefully remodeled home situated on a corner lot with many extras. Located at the end of the street, the property offers privacy, a fenced yard, multiple storage sheds/garages, and a deck off the primary bedroom overlooking the backyard. The lower level includes a bright and open living/dining room with hardwood floors leading into a completely remodeled kitchen featuring all new appliances,

  Cory Evangelisto NOCHER REALTY

  19 Fairgrounds Ave, North Adams, MA 01247
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  /45

  $369,000

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft

  205 High St, Lee, MA 01238

  Enjoy downtown living in this 4 Bedroom 2 Bath New England farmhouse. Built in the early20th century, this home has a diverse use of residential, commercial or mixed use on a residential street. The kitchen has been updated with plenty of cabinet space. A cozy living room fireplace and a enclosed porch with numerous windows that welcome fresh summertime breezes and a patio for summer leisure

  Anthony Caropreso MACCARO REAL ESTATE

  205 High St, Lee, MA 01238
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  /37

  $329,900

  • 3 Beds
  • 1.5 Baths
  • 1,563 Sq Ft

  1070 Holmes Rd, Pittsfield, MA 01201

  Wonderful home located at the southern end of Holmes Rd. Moments away from Tanglewood and other cultural attractions of the Berkshires. Close to skiing at Bousquet, shopping and restaurants. This ranch style home features a large living room with a fireplace. Formal dining room leads into the kitchen. Three good sized bedrooms, a full bath and half bath all on one level. The kitchen opens out to

  Derek Strzepa NOCHER REALTY

  1070 Holmes Rd, Pittsfield, MA 01201
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  /28

  $347,700

  • 2 Beds
  • 2 Baths
  • 1,314 Sq Ft

  14 Blotz Rd, Washington, MA 01223

  Set along a quiet country road in Washington, this lovingly preserved 1845 Cape exudes charm and timeless character. From the moment you step inside, wide-plank floors, hand-hewn beams, and the cozy glow of a wood stove make you feel instantly at home.Winter evenings here are magical--imagine snow falling outside while you curl up with a book, listen to the fire crackle, and let the world slow

  Amy Shufelt BERKSHIRE LISTINGS

  14 Blotz Rd, Washington, MA 01223
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  /22

  $349,900

  • 3 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  127 Oak Hill Rd, Pittsfield, MA 01201

  Welcome Home! This inviting 3BR, 2.5BA raised ranch in Pittsfield offers an open, sun filled layout perfect for both everyday living and entertaining. The finished walk-out basement offers additional living space,ideal for a family room, home office and guest area. Outside, you will enjoy a automatic awning covered deck, a large yard with fire pit, perfect for gardening or hosting summer

  Stacy Hebb NOCHER REALTY

  127 Oak Hill Rd, Pittsfield, MA 01201
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  /7

  $380,000

  • Land
  • 15 Acres
  • $25,333 per Acre

  0 Churchill St Unit 248259, Pittsfield, MA 01201

  Price reduction. Motivated seller.Discover the ideal setting for your next home or retreat on this 15-acre parcel in West Pittsfield. Thoughtfully prepared, the property already features installed electricity, along with a newly constructed driveway and building pad. Enjoy a perfect blend of open and wooded land, including 5+ acres of fields, 10 acres of forest, and approximately 700 feet of road

  Sally Carr KEY REALTY

  0 Churchill St Unit 248259, Pittsfield, MA 01201
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  /15

  $368,000

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft

  4 Morgan Manor Unit 4, Lenox, MA 01240

  Lenox in-town condo.....ready for a new owner, need a close location to Tanglewood, Shakespeare and Company, The Mount, Venfort Hall, Kennedy Park, Pleasant Valley Wildlife Sanctuary? Well this is the perfect location!2 bedrooms, 1 full bath, wood floors and carpeted bedrooms, great light ....fully applianced kitchen....Easy to show!

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  4 Morgan Manor Unit 4, Lenox, MA 01240
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  /42

  $349,000

  • 4 Beds
  • 2 Baths
  • 1,741 Sq Ft

  5 Marco Dr, Pittsfield, MA 01201

  Move-in ready and freshly reimagined, this spacious home offers 4 bedrooms and 2 full baths, including a fully finished, heated lower level that expands the living space. The upper level features bright living and dining areas, a functional kitchen with direct access to a two-tier deck for outdoor living, and two comfortable bedrooms with ample closet space. The finished lower level, filled with

  Team ROVI Real Broker MA, LLC

  5 Marco Dr, Pittsfield, MA 01201
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  /56

  $349,000

  • 4 Beds
  • 2 Baths
  • 2,148 Sq Ft

  47 Onota St, Pittsfield, MA 01201

  Step onto the spacious covered porch then enter into the grand foyer while you are there take notice of the beautiful hardwood details throughout the home. First floor offers a large living room, dining room, bathroom and a remodeled kitchen. Second floor you have three-bedrooms, full bathroom and a conveniently located laundry room. The third floor is where the fourth bedroom is located with

  Michelle Picard NOCHER REALTY

  47 Onota St, Pittsfield, MA 01201
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  /13

  $390,000

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  112 Sampson Pkwy, Pittsfield, MA 01201

  Beautifully maintained 2 bedroom brick ranch featuring gorgeous wood floors throughout. The inviting living room showcases a cozy fireplace & flows seamlessly into the formal dining room. The remodeled kitchen offers many cabinets & counter space.A bright & sunny room overlooks the fully fenced rear yard & provides direct access to the deck - ideal for relaxing or outdoor gatherings.The finished

  Deborah Dwyer DWYER AGENCY

  112 Sampson Pkwy, Pittsfield, MA 01201
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  /29

  $389,900

  • 3 Beds
  • 2 Baths
  • 2,747 Sq Ft

  18 W Mountain Rd, Cheshire, MA 01225

  Discover the warmth and character of this inviting post and beam home, showcasing wood floors and cozy fireplaces that create the perfect setting for comfortable living. A walk-up attic offers exciting potential for additional space, while the oversized garage provides ample storage for vehicles, hobbies, and equipment. Set on just over an acre, the property also features a seasonal cabin with

  Robin Moore 413 REAL ESTATE

  18 W Mountain Rd, Cheshire, MA 01225
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  /37

  $344,900

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

  74 Norman Ave, Pittsfield, MA 01201

  *Virtual tour with floor plans availableThis unique home sits on a large lot with a fabulous yard. There is a driveway with carport and shed included. Upon entering the home you will find a convenient porch leading to the living room with wood-burning fireplace. The first floor also features a bedroom with a loft, as well as full bathroom with laundry, dining room and kitchen. There is a large

  Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.

  74 Norman Ave, Pittsfield, MA 01201
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  /25

  $375,000

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft

  42 Bryant St, Pittsfield, MA 01201

  Spacious and adaptable, this Pittsfield home offers exceptional flexibility for today's lifestyle. The first floor features a sun-filled living room with hardwood floors and a bay window, a generous kitchen with an island and large dining area, and a mudroom with convenient first-floor laundry. A full bath and two bonus rooms on the main level provide versatile options for home offices, guest

  Danielle Giulian WILLIAM PITT SOTHEBY'S - LENOX

  42 Bryant St, Pittsfield, MA 01201
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  /47

  $337,500

  • 2 Beds
  • 3 Baths
  • 1,552 Sq Ft

  7 Rolling Hills Unit 7-1, Lenox, MA 01240

  Think spring in the Berkshires and enjoy condo living in Lenox at Rolling Hills. Spacious end unit brings in natural light and offers two bedrooms/two baths on upper level with an additional full bath and family room/office on the finished lower level. In this unit owners have replaced the custom-sized slider and the windows adding to energy efficiency. Central a/c, natural gas. The former golf

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  7 Rolling Hills Unit 7-1, Lenox, MA 01240
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  /12

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  32 Jason St, Pittsfield, MA 01201

  Location is a must!Many improvements by current owners. Roof replaced in past 10 years. Orangeburg pipe replaced from house to street. Furnace replaced. Kitchen redone. Chimney pipe replaced.Just a few updates.

  Deborah Dwyer DWYER AGENCY

  32 Jason St, Pittsfield, MA 01201
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  /5

  $385,900

  • Land
  • 15.91 Acres
  • $24,255 per Acre

  2 New Lenox Rd, Lenox, MA 01240

  Opportunity Knocks! Expansive Lenox parcel - currently 2 approved building lots (1.0 acre and 14.91 acres) w/ frontage on East Street and New Lenox Road. Seller has a proposed subdivision that would make it 4 lots (1.0 acre, 3.5 acres, 7.59 acres & 2.98 acres). Build your dream home or take advantage of this unbeatable development opportunity in highly sought after location! Water, sewer & gas on

  Sean Taylor MORESI REAL ESTATE PARTNERS

  2 New Lenox Rd, Lenox, MA 01240
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  /18

  $395,900

  • 4 Beds
  • 1.5 Baths
  • 1,726 Sq Ft

  15 Ballou St, North Adams, MA 01247

  Location! Location! Location! Walk to downstreet or Mass MoCA. and shopping.Lovingly cared for 4 bedroom home. Upgrades throughout including New roof, owned solar, USB ports in each room, New heating system with Mini splits, Oil tanks removed (but pipes remain should the buyer want to convert back to oil). Smart house with smart switches throughout. New HW heater and dehumidifier. One & Done

  Sandra Sorel COLDWELL BANKER REALTY

  15 Ballou St, North Adams, MA 01247
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  /40

  $384,000

  • 3 Beds
  • 1.5 Baths
  • 1,677 Sq Ft

  20 Moscow Rd, West Stockbridge, MA 01266

  Short walk to quaint downtown West Stockbridge featuring local coffee shop, variety store, restaurants and shops. Just a few minutes to local theatres, music venues, Tanglewood, historic Stockbridge, and the Mass Pike. Beautiful open yard great for summer entertaining including cookouts, yard games or just relaxing and reading a book! Cozy fireplace for those beautiful snowy New England nights.

  Mark Harris SIGNATURE ASSOCIATES

  20 Moscow Rd, West Stockbridge, MA 01266
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  /7

  $349,000

  • Land
  • 19.73 Acres
  • $17,689 per Acre

  0 Hayes Hill Rd Unit 247870, New Marlborough, MA 01244

  Just shy of 20 acres. Make your way to the top for views, you won't be disappointed. An abundance of wildlife, and not a building in sight. Come take a look and make this your Berkshire retreat!

  Lawrence Reilly THE KINDERHOOK GROUP

  0 Hayes Hill Rd Unit 247870, New Marlborough, MA 01244
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  /36

  $388,000

  • 3 Beds
  • 1.5 Baths
  • 1,386 Sq Ft

  2010-2012 Clayton Mill River Rd, New Marlborough, MA 01259

  Nestled in the foothills of beautiful Southern Berkshires this turn key 3 bed 1.5 ba home is flanked by protected farmland & mountain views from nearly every room. Historic Southfield Village & nearby surrounds offer a variety of venues for dining on farm to table fare, a myriad of cultural events, nearby shopping, public & private schools. Kayak, fish & play in our many lakes, rivers & streams.

  Brenda McLean WILLIAM PITT SOTHEBY'S - SALISBURY

  2010-2012 Clayton Mill River Rd, New Marlborough, MA 01259
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  /37

  $384,900

  • 3 Beds
  • 1.5 Baths
  • 2,061 Sq Ft

  240 Kirchner Rd, Dalton, MA 01226

  Step inside and you'll be welcomed by a warm, cabin-like feel featuring wood-beamed ceilings and walls, gleaming hardwood floors, and a cozy wood stove in the open-concept living and dining area. The kitchen is complete with maple cabinetry and plenty of storage, making it as functional as it is inviting. With 2-3 bedrooms and 1.5 baths, this single-level home is designed for easy living. An

  Nancy Bush Brooks SIGNATURE ASSOCIATES

  240 Kirchner Rd, Dalton, MA 01226
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  /27

  $395,000

  • 3 Beds
  • 1 Bath
  • 1,052 Sq Ft

  910 N Hoosac Rd, Williamstown, MA 01267

  The Charm and Style of an 1850's post and beam colonial masterfully blended with the updated comfort and appeal of a tasteful 1990's complete renovation. Quaint, charming, cozy, comfortable, efficient, inviting...we could easily add another ten or twenty complimentary descriptive words to paint the attractive qualities of this historic house. Just over 1,000 square feet total, this charmer has it

  Carolyn Umlauf HARSCH ASSOCIATES

  910 N Hoosac Rd, Williamstown, MA 01267
• 

  

  /43

  $335,900

  • 3 Beds
  • 2 Baths
  • 1,567 Sq Ft

  1020 Sandmill Rd, Adams, MA 01220

  Welcome to this expansive ranch style home set on a peaceful acre with scenic views of a babbling brook and beautiful woodlands. Designed for easy one-level living, this home features two bedrooms and full bath in addition to a spacious primary en-suite with sliders that open to the outdoors-perfect for enjoying morning coffee or wine under the stars. The living and dinning room combination

  Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  1020 Sandmill Rd, Adams, MA 01220
• 

  

  /32

  $369,900

  • 3 Beds
  • 4 Baths
  • 8,544 Sq Ft

  50-52 N Summer St, Adams, MA 01220

  This is a rare opportunity to acquire a robust, four-unit, mixed-use commercial and residential building strategically located near downtown attractions. The classic brick construction provides enduring appeal, while recent capital improvements significantly enhance the property's longevity and reduce immediate maintenance concerns. New roof in 2025, heating systems less than 6 years old, most

  Jason Nocher NOCHER REALTY

  50-52 N Summer St, Adams, MA 01220
• 

  

  /10

  $329,000

  • Land
  • 8.69 Acres
  • $37,860 per Acre

  10 Mountain Rd, Mount Washington, MA 01258

  RARE OPPORTUNITY. Private parcel with open views potential, atarting from the idyllic cul-de-sac, on Mountain Rd. in Mt. Washington, MA. This exclusive, private land parcel has 8.69 level and gently rolling acres.: Septic Field has been partially installed, Well has been drilled , and rough driveway installed. Fiber Optic is available. The plans for 4BR+4BA house with an in-law suite have been

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  10 Mountain Rd, Mount Washington, MA 01258

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