67,791

Berkshire County, MA Homes

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  • /42

    $3,750,000

    Pending
    • 34 Beds
    • 31 Baths
    • 40,241 Sq Ft

    349 Old Stockbridge Rd, Lenox, MA 01240

    Rare 16.76± acre contiguous institutional campus and redevelopment opportunity in Lenox, MA, in the heart of the Berkshires. Anchored by Overlee, a historic 1903 estate, the property includes multiple buildings with 32 dormitory-style bedrooms, classroom and administrative space, dining facilities, shared common areas, and a large gymnasium. Existing infrastructure includes internal roadways,

    Agent Photo

    Selina Lamb

    Birch Properties

    349 Old Stockbridge Rd, Lenox, MA 01240
  • /17

    $2,300 Per Month

    • 4 Beds
    • 1.5 Baths
    • 1,292 Sq Ft
    • House for Rent

    88 Wahconah St, Pittsfield, MA 01201

    Fully furnished 3-bedroom home with an additional room set up as a dedicated office—perfect for remote work or extended stays. This property includes all utilities, cable, and high-speed internet for a seamless, move-in-ready experience. Two off-street parking spaces are available. Conveniently located just minutes from Berkshire Medical Center and close to downtown Pittsfield, with easy access

    Patricia Molina Century 21 North East

    88 Wahconah St, Pittsfield, MA 01201
  • /27

    $299,600

    Sold Jun 30, 2025

    106 Crane Ave, Pittsfield, MA 01201

    • 3 Beds
    • 1 Bath
    • 1,265 Sq Ft
    • Built 1950

    Last Sold Summary

    • $237/SF
    • 8 Days On Market

    Current Estimated Value $298,247

    Last Listing Agent Kellie Perrault KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    106 Crane Ave, Pittsfield, MA 01201
    • /27

      Not Listed For Sale

      37 Corey Rd Unit 52, Hancock, MA 01237

      • 2 Beds
      • 1.5 Baths
      • 896 Sq Ft
      • Built 1985
      37 Corey Rd Unit 52, Hancock, MA 01237

      Last Sold Summary

      • 13 Days On Market

  • /36

    $895,000

    Pending
    • 4 Beds
    • 2 Baths
    • 2,515 Sq Ft

    10 Prospect Hill, Stockbridge, MA 01263

    Rare opportunity on coveted Prospect Hill Road in Stockbridge. Offered for the first time in more than 40 years, this c.1880 residence is privately set on 3.5 acres just moments from downtown Stockbridge, the Red Lion Inn, Tanglewood, Lenox, and the Berkshires' renowned cultural attractions. The home offers approximately 2,515 square feet with wide-plank floors, exposed brick, wood beams,

    Agent Photo

    Selina Lamb

    Birch Properties

    10 Prospect Hill, Stockbridge, MA 01263
  • /11

    $1,650

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • 124-126 Appleton

    124-126 Appleton Ave Unit 126 Second Floor, Pittsfield, MA 01201

    124-126 Appleton Ave Unit 126 Second Floor, Pittsfield, MA 01201
  • /4

    $65,000

    Sold May 21, 2026

    lot 8 Captain Whitney Rd, Becket, MA 01223

    • Land
    • 15.2 Acres
    • $4,276 per Acre

    Last Sold Summary

    • 8 Days On Market

    Last Listing Agent Jeff Wilkinson STONE HOUSE PROPERTIES, LLC

    lot 8 Captain Whitney Rd, Becket, MA 01223
    • /9

      Not Listed For Sale

      336 Sweet Farm Rd, Williamstown, MA 01267

      336 Sweet Farm Rd, Williamstown, MA 01267

      Last Sold Summary

      • 40 Days On Market

  • /14

    $179,000

    • Land
    • 2.5 Acres
    • $71,600 per Acre

    0 River Rd, Monterey, MA 01245

    Some land just feels right the moment you step onto it. This 2.5-acre parcel on River Road in prime Monterey has that quality, a generous level clearing that invites something to be built and loved here. With 550 feet of road frontage, the practical bones are exceptional.To the east and north, the property borders the Berkshire National Fish Hatchery, a working conservation landscape where

    Agent Photo

    Chapin Fish

    WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    0 River Rd, Monterey, MA 01245
  • /10

    $1,900 Per Month

    • 0.5 Baths
    • 1,200 Sq Ft
    • Property for Rent

    402 Park St, Great Barrington, MA 01230

    Looking for the perfect space to grow your business? This exceptional first-floor commercial property in the charming village of Housatonic checks all the boxes. Step into a spacious, open-concept layout, ideal for retail, office, or creative ventures. With both heating and air conditioning, you'll have year-round comfort to keep your team and customers happy. Need a little extra privacy? The

    Suzann Ward HOUSATONIC REAL ESTATE

    402 Park St, Great Barrington, MA 01230
  • /74

    $650,000

    Sold Aug 29, 2025

    56 Grist Mill Rd, Richmond, MA 01254

    • 4 Beds
    • 2.5 Baths
    • 5,223 Sq Ft
    • Built 1970

    Last Sold Summary

    • 7% Below List Price
    • $124/SF
    • 97 Days On Market

    Last Listing Agent Jason Nocher NOCHER REALTY

    56 Grist Mill Rd, Richmond, MA 01254
    • /9

      Not Listed For Sale

      68 Lyman St, Pittsfield, MA 01201

      • 12 Beds
      • 4 Baths
      • 4,284 Sq Ft
      • Built 1920
      68 Lyman St, Pittsfield, MA 01201

      Last Sold Summary

      • 2 Days On Market

  • /59

    $1,375,000

    $120K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 5,363 Sq Ft

    400 Rathbun Rd, Lanesborough, MA 01237

    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

    Agent Photo

    Diane Thorson

    WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    400 Rathbun Rd, Lanesborough, MA 01237
  • /23

    $2,975

    Total Monthly Price

    • 3 Beds
    • 3 Baths
    • 1,952 Sq Ft
    • Beautiful 3bd/3ba Condo For Rent

    8 Applewood Ln, Pittsfield, MA 01201

    Charming 3-bedroom, 3-bath condominium in Pittsfield, MA, offering an attached garage and a welcoming front porch. Inside, hardwood floors flow through bright living areas while cozy carpeting covers the upstairs bedroom areas. A first floor office provides a dedicated workspace close to the entry. The kitchen features stainless steel appliances, and an entertainment deck extends living outdoors.

    8 Applewood Ln, Pittsfield, MA 01201
  • /31

    $212,000

    Sold Jun 26, 2026

    62 Walker St, North Adams, MA 01247

    • 2 Beds
    • 2 Baths
    • 1,276 Sq Ft
    • Built 1900

    Last Sold Summary

    • 6% Above List Price
    • $166/SF
    • 3 Days On Market

    Current Estimated Value $200,640

    Last Listing Agent Alyssa Sherman MORESI REAL ESTATE PARTNERS

    62 Walker St, North Adams, MA 01247
    • /29

      Est $374,932

      Not Listed For Sale

      201 N Main St, Sandisfield, MA 01255

      • 4 Beds
      • 2 Baths
      • 2,095 Sq Ft
      • Built 1977
      201 N Main St, Sandisfield, MA 01255

      Last Sold Summary

      • 248 Days On Market

  • /7

    $789,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    403 Churchill St, Pittsfield, MA 01201

    To Be Built - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 2.14-acre lot (MLS # 248343), featuring a private

    Agent Photo

    Corey Bishop

    BISHOP WEST REAL ESTATE

    403 Churchill St, Pittsfield, MA 01201
  • /15

    $2,000 Per Month

    • 0.5 Baths
    • 2,000 Sq Ft
    • Property for Rent

    490 Main St, Great Barrington, MA 01230

    Second floor office space in a high-traffic location. Currently configured with four offices, reception area and half bath. This space has air conditioning, forced air heat, and its own electric meter. Ample off-street parking available. The space comes furnished. Utilities not included.

    Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

    490 Main St, Great Barrington, MA 01230
  • /27

    $15,000

    Sold Sep 03, 2025

    0 Highland Way, Otis, MA 01253

    • Land
    • 1.06 Acres
    • $14,151 per Acre

    Last Sold Summary

    • 69% Below List Price
    • 665 Days On Market

    Last Listing Agent Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

    0 Highland Way, Otis, MA 01253
    • /35

      Not Listed For Sale

      4 Rolling Hills Unit 4-9, Lenox, MA 01240

      • 2 Beds
      • 3 Baths
      • 1,552 Sq Ft
      • Built 1976
      4 Rolling Hills Unit 4-9, Lenox, MA 01240

      Last Sold Summary

      • 1 Day On Market

  • /35

    $365,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,804 Sq Ft

    161 Fort Hill Ave, Pittsfield, MA 01201

    This inviting Cape Cod-style home offers the ideal blend of classic Berkshire charm and thoughtful modern updates. Set back privately from the road, it provides a peaceful, wooded retreat while keeping you just minutes from Berkshire Community College, the New York border, and downtown Pittsfield.With 3 bedrooms plus a flexible 4th, this layout adapts effortlessly to your family's needs--whether

    Agent Photo

    Mary Smith

    BISHOP WEST REAL ESTATE

    161 Fort Hill Ave, Pittsfield, MA 01201
  • /13

    $1,650

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,035 Sq Ft
    • Church Street

    520 Church St Unit 1, North Adams, MA 01247

    Renovated 2BR Apartment Near MCLA, MASS MoCA & Hospital | Pet Friendly | Private Yard$1,650/monthBeautifully renovated 2-bedroom, 1-bath apartment in a prime North Adams location, offering the perfect blend of character, privacy, and modern updates. Ideal for professionals, MCLA faculty/staff, educators, healthcare workers, or anyone looking for a comfortable home close to everything North Adams

    520 Church St Unit 1, North Adams, MA 01247
  • /43

    $342,000

    Sold May 20, 2026

    12 Sherrill Ave, Pittsfield, MA 01201

    • 3 Beds
    • 1.5 Baths
    • 1,188 Sq Ft
    • Built 1950

    Last Sold Summary

    • 20% Above List Price
    • $288/SF
    • 5 Days On Market

    Current Estimated Value $279,011

    Last Listing Agent Maureen Kirby NOCHER REALTY

    12 Sherrill Ave, Pittsfield, MA 01201
    • /48

      Est $726,251

      Not Listed For Sale

      78 Bull Hill Rd, Lanesborough, MA 01237

      • 4 Beds
      • 2.5 Baths
      • 3,416 Sq Ft
      • Built 1900
      78 Bull Hill Rd, Lanesborough, MA 01237

      Last Sold Summary

      • 25 Days On Market

  • /28

    $299,900

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    15 Haskell Rd, Hinsdale, MA 01235

    Bring your vision to life! Situated on over 5 acres, this ranch-style home with a full walkout basement is ready for the next owner to bring it to completion. Offering 3 bedrooms and 2 bathrooms. Finish the living space in the lower level walkout area to create more useable square footage. The home is currently in the sheetrock stage with electrical and rough plumbing already completed. Sold

    Agent Photo

    Corey Bishop

    BISHOP WEST REAL ESTATE

    15 Haskell Rd, Hinsdale, MA 01235
  • /13

    $2,250 Per Month

    • 1 Bath
    • 750 Sq Ft
    • Property for Rent

    27 Housatonic St, Lenox, MA 01240

    Make your dreams come true! Perhaps one of the best retail locations in Historic downtown Lenox. This highly sought after space is centrally located with high foot traffic count and is located on the corner of Church St. and Housatonic. The 750 sq.ft. has two great large window wells along the sidewalk entrance and includes your own bathroom and kitchenette. Nestled amongst dozens of small shops,

    Tim Gallagher STONE HOUSE PROPERTIES, LLC

    27 Housatonic St, Lenox, MA 01240
  • /30

    $685,000

    Sold Oct 30, 2025

    155 High St Hill Rd, Windsor, MA 01270

    • 3 Beds
    • 2.5 Baths
    • 2,572 Sq Ft
    • Built 2003

    Last Sold Summary

    • 1% Above List Price
    • $266/SF
    • 4 Days On Market

    Current Estimated Value $711,603

    Last Listing Agent Jesse Dimitropolis RE/MAX COMPASS

    155 High St Hill Rd, Windsor, MA 01270
    • /8

      Not Listed For Sale

      Unlisted Address

      Unlisted Address

      Last Sold Summary

      • 697 Days On Market

  • /92

    $665,000

    $35K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 2,748 Sq Ft

    10 Lillybrook Rd, Pittsfield, MA 01201

    Beautiful 4 bedroom contemporary on Lilybrook Road. Vaulted entry way leads to living (sitting) room flanked by formal dining room. Also on the first floor is oversized great (family) room with fireplace, large eat-in kitchen and private master (in-law) suite with full bath and jet tub. The second floor has another master suite with full private bath, two additional bedrooms, and a second full

    Agent Photo

    Paul Clark

    CLARK REALTY GROUP LLC

    10 Lillybrook Rd, Pittsfield, MA 01201
  • /7

    $2,800

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • Elegant Single-Family Home with Chef’s Kitchen (Newly Reduced Price)

    398 Elm St, Pittsfield, MA 01201

    This fully furnished beautifully maintained single-family home is located in a highly sought after neighborhood in the Berkshires. Thoughtfully updated with high-end finishes and modern conveniences, this home offers a perfect combination of elegance, comfort, and functionality. Step into a bright and spacious open-concept layout featuring rich flooring, oversized windows, and an abundance of

    398 Elm St, Pittsfield, MA 01201
  • /13

    $295,500

    Sold Oct 06, 2025

    61 Pomeroy Ave, Pittsfield, MA 01201

    • 6 Beds
    • 2 Baths
    • 3,081 Sq Ft
    • Built 1880

    Last Sold Summary

    • 6% Above List Price
    • $96/SF
    • 86 Days On Market

    Current Estimated Value $312,946

    Last Listing Agent Jessie Carlino MACCARO REAL ESTATE

    61 Pomeroy Ave, Pittsfield, MA 01201
    • /31

      Not Listed For Sale

      206 E Main St, Ashley Falls, MA 01222

      • 3 Beds
      • 2 Baths
      • 2,160 Sq Ft
      • Built 1850
      206 E Main St, Ashley Falls, MA 01222

      Last Sold Summary

      • 167 Days On Market

  • /10

    $149,000

    $6K PRICE DROP
    • Land
    • 5.24 Acres
    • $28,435 per Acre

    104 Hupi Rd, Monterey, MA 01245

    Ready to build a new custom home with all your personal touches! Views of Lake Garfield. Close to downtown Monterey. Fresh 5 acre parcel to construct a magnificent home in the Berkshires!

    Agent Photo

    Cristian Sanchez

    COHEN & WHITE ASSOCIATES

    104 Hupi Rd, Monterey, MA 01245
  • /15

    $3,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,557 Sq Ft
    • House for Rent

    33 S Main Rd, Otis, MA 01253

    AVAILABLE SEPTEMBER 1, 2026 T0 6/30/2027. Nicely renovated and beautifully furnished Colonial rental located in the heart of Otis. The updated eat-in kitchen is enhanced by attractive wood floors that exist throughout the home. The bathrooms, the propane furnace, and the windows have also been updated. The town has provided high speed broadband service throughout the community so if you need to

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    33 S Main Rd, Otis, MA 01253
  • /54

    $275,000

    Sold Jul 03, 2025

    7 Bieniek Ave, Adams, MA 01220

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1956

    Last Sold Summary

    • 8% Below List Price
    • $275/SF
    • 10 Days On Market

    Current Estimated Value $277,813

    Last Listing Agent Aimee Annichiarico BISHOP WEST REAL ESTATE

    7 Bieniek Ave, Adams, MA 01220
    • /42

      Est $515,728

      Not Listed For Sale

      162 Bailey Rd, Hancock, MA 01237

      • 3 Beds
      • 2.5 Baths
      • 3,730 Sq Ft
      • Built 2005
      162 Bailey Rd, Hancock, MA 01237

      Last Sold Summary

      • 46 Days On Market

  • /17

    $119,900

    • 2 Beds
    • 2 Baths
    • 773 Sq Ft

    31 2nd Ave, Cheshire, MA 01225

    Built in 2023 and impeccably maintained, this move-in ready home offers modern comfort with an open, bright layout designed for easy living. The spacious kitchen flows seamlessly into the living area, creating the perfect space for entertaining or relaxing. A practical mudroom adds everyday convenience, while two full bathrooms and comfortable bedrooms provide flexibility for family or guests.

    Agent Photo

    Corey Bishop

    BISHOP WEST REAL ESTATE

    31 2nd Ave, Cheshire, MA 01225
  • /24

    $2,750

    Total Monthly Price

    • 4 Beds
    • 1.5 Baths
    • 1,535 Sq Ft
    • 4 Bedroom Colonial Home in Williamstown

    800 Simonds Rd, Williamstown, MA 01267

    Newly updated 4-bedroom, 1.5-bath colonial is located in beautiful Williamstown, near Williams College., a short drive to Bennington, VT This home has been well cared for and is ready for you to move in. Enjoy the fully screened porch or relax in the spacious, fenced-in backyard. The house features four bedrooms, with a full bathroom on the second floor and a half bath on the first floor. The

    800 Simonds Rd, Williamstown, MA 01267
  • /42

    $435,000

    Sold May 26, 2026

    184 Washington Mountain Rd, Lee, MA 01238

    • 3 Beds
    • 1.5 Baths
    • 1,293 Sq Ft
    • Built 1966

    Last Sold Summary

    • $336/SF
    • 53 Days On Market

    Current Estimated Value $431,462

    Last Listing Agent The Mazzeo Duo BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    184 Washington Mountain Rd, Lee, MA 01238
    • /38

      Est $788,810

      Not Listed For Sale

      305 Sequena Dr, Sandisfield, MA 01255

      • 4 Beds
      • 3.5 Baths
      • 2,878 Sq Ft
      • Built 1988
      305 Sequena Dr, Sandisfield, MA 01255

      Last Sold Summary

      • 15 Days On Market

Showing Results 121 - 160, Page 4 of 18

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