67,295

Berkshire County, MA Homes

Section Image
  • 78 Winship Ave, Pittsfield, MA 01201
    78 Winship Ave, Pittsfield, MA 01201
    78 Winship Ave, Pittsfield, MA 01201
    /33

    $291,000 Sold Apr 30, 2025

    78 Winship Ave, Pittsfield, MA 01201

    • 3 Beds
    • 1.5 Baths
    • 1,548 Sq Ft
    • Built 1927

    Last Sold Summary

    • 1% Below List Price
    • $188/SF
    • 20 Days On Market

    Current Estimated Value $303,600

    Last Listing Agent Samar Moushabeck WILLIAM RAVEIS REAL ESTATE

    78 Winship Ave, Pittsfield, MA 01201
    • 9 Oberlaken Dr, Otis, MA 01253
      9 Oberlaken Dr, Otis, MA 01253
      9 Oberlaken Dr, Otis, MA 01253
      /33

      Est $335,150 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,240 Sq Ft

      9 Oberlaken Dr, Otis, MA 01253

      9 Oberlaken Dr, Otis, MA 01253
  • 9 October Hill Dr, Lenox, MA 01240
    9 October Hill Dr, Lenox, MA 01240
    9 October Hill Dr, Lenox, MA 01240
    /60

    $1,585,000

    • 4 Beds
    • 4.5 Baths
    • 3,991 Sq Ft

    9 October Hill Dr, Lenox, MA 01240

    Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a

    Paula McLean PAULA MCLEAN REALTORS INC.

    9 October Hill Dr, Lenox, MA 01240
  • 40 Interlaken Rd, Stockbridge, MA 01262
    40 Interlaken Rd, Stockbridge, MA 01262
    40 Interlaken Rd, Stockbridge, MA 01262
    /23

    $175,000 Sold Feb 28, 2025

    40 Interlaken Rd, Stockbridge, MA 01262

    • 2 Beds
    • 1 Bath
    • 749 Sq Ft
    • Built 1800

    Last Sold Summary

    • 20% Below List Price
    • $234/SF
    • 79 Days On Market

    Current Estimated Value $218,402

    Last Listing Agent Shelley Cozzaglio LAMACCHIA REALTY, INC

    40 Interlaken Rd, Stockbridge, MA 01262
    • 135 Ed Jones Rd, Otis, MA 01253
      135 Ed Jones Rd, Otis, MA 01253
      135 Ed Jones Rd, Otis, MA 01253
      /45

      Est $583,342 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,316 Sq Ft

      135 Ed Jones Rd, Otis, MA 01253

      135 Ed Jones Rd, Otis, MA 01253
  • 205 High St, Lee, MA 01238
    205 High St, Lee, MA 01238
    205 High St, Lee, MA 01238
    /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
  • 209 Velma Ave, Pittsfield, MA 01201
    209 Velma Ave, Pittsfield, MA 01201
    209 Velma Ave, Pittsfield, MA 01201
    /36

    $364,400 Sold Oct 30, 2025

    209 Velma Ave, Pittsfield, MA 01201

    • 3 Beds
    • 2 Baths
    • 1,691 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Above List Price
    • $215/SF
    • 3 Days On Market

    Last Listing Agent Rena Rose MOCKINGBIRD REAL ESTATE

    209 Velma Ave, Pittsfield, MA 01201
    • 14 Highland Way, Otis, MA 01253
      14 Highland Way, Otis, MA 01253
      14 Highland Way, Otis, MA 01253
      /45

      Est $541,371 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,568 Sq Ft

      14 Highland Way, Otis, MA 01253

      14 Highland Way, Otis, MA 01253
  • 33 Alpine Trail, Pittsfield, MA 01201
    33 Alpine Trail, Pittsfield, MA 01201
    33 Alpine Trail, Pittsfield, MA 01201
    /69

    $730,000

    • 5 Beds
    • 4.5 Baths
    • 3,381 Sq Ft

    33 Alpine Trail, Pittsfield, MA 01201

    Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and

    Cortney Dupont COHEN & WHITE ASSOCIATES

    33 Alpine Trail, Pittsfield, MA 01201
  • 118 Beartown Mountain Rd, Monterey, MA 01245
    118 Beartown Mountain Rd, Monterey, MA 01245
    118 Beartown Mountain Rd, Monterey, MA 01245
    /29

    $820,000 Sold Nov 05, 2025

    118 Beartown Mountain Rd, Monterey, MA 01245

    • 4 Beds
    • 2.5 Baths
    • 2,480 Sq Ft
    • Built 1980

    Last Sold Summary

    • 1% Below List Price
    • $331/SF
    • 42 Days On Market

    Last Listing Agent Kate Lascar COMPASS MASSACHUSETTS , LLC GB

    118 Beartown Mountain Rd, Monterey, MA 01245
    • 499 Norton Rd, Otis, MA 01253
      499 Norton Rd, Otis, MA 01253
      499 Norton Rd, Otis, MA 01253
      /31

      Est $899,363 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,017 Sq Ft

      499 Norton Rd, Otis, MA 01253

      499 Norton Rd, Otis, MA 01253
  • 16 2nd Ave, Cheshire, MA 01225
    16 2nd Ave, Cheshire, MA 01225
    16 2nd Ave, Cheshire, MA 01225
    /20

    $69,900 Pending

    • 2 Beds
    • 1 Bath
    • 780 Sq Ft

    16 2nd Ave, Cheshire, MA 01225

    Clean, bright, & move-in ready. This remodeled 2-bedroom, 1-bath mobile home offers simple Berkshire living with a comfortable layout & plenty of updates. The kitchen shines with stainless steel appliances & fresh paint. The bathroom was fully renovated with subway tile, built-in shower seat, & modern finishes. There's a 3-season room that could easily be extra living space or a 3rd bedroom with

    THE KAHN TEAM BISHOP WEST REAL ESTATE

    16 2nd Ave, Cheshire, MA 01225
  • 198 Allengate Ave, Pittsfield, MA 01201
    198 Allengate Ave, Pittsfield, MA 01201
    198 Allengate Ave, Pittsfield, MA 01201
    /40

    $330,000 Sold Sep 12, 2025

    198 Allengate Ave, Pittsfield, MA 01201

    • 4 Beds
    • 1 Bath
    • 1,267 Sq Ft
    • Built 1947

    Last Sold Summary

    • $260/SF
    • 8 Days On Market

    Current Estimated Value $326,367

    Last Listing Agent Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    198 Allengate Ave, Pittsfield, MA 01201
    • 45 Art School Rd, Monterey, MA 01245
      45 Art School Rd, Monterey, MA 01245
      45 Art School Rd, Monterey, MA 01245
      /77

      Est $2,433,014 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 6,096 Sq Ft

      45 Art School Rd, Monterey, MA 01245

      45 Art School Rd, Monterey, MA 01245
  • 10 Thrushwood Ln, Great Barrington, MA 01230
    10 Thrushwood Ln, Great Barrington, MA 01230
    10 Thrushwood Ln, Great Barrington, MA 01230
    /11

    $829,000 Pending

    • 5 Beds
    • 4.5 Baths
    • 3,808 Sq Ft

    10 Thrushwood Ln, Great Barrington, MA 01230

    POOL COMMUNITY: BUILD YOUR DREAM HOME: Open plan living with, first floor master, fireplace, screened porch, high ceilings, two car garage, community pool. HOA covers all lawn maintenance, plowing, shoveling up to the front door. Quality New Construction. This price cannot be matched. 10 months to move into your beautiful new home. Photos are from a similar home with the same floor plan in the

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    10 Thrushwood Ln, Great Barrington, MA 01230
  • 83 Walker St, North Adams, MA 01247
    83 Walker St, North Adams, MA 01247
    83 Walker St, North Adams, MA 01247
    /28

    $373,000 Sold Dec 09, 2025

    83 Walker St, North Adams, MA 01247

    • 3 Beds
    • 2.5 Baths
    • 1,264 Sq Ft
    • Built 1940

    Last Sold Summary

    • 6% Below List Price
    • $295/SF
    • 50 Days On Market

    Last Listing Agent Ashlee Colon BISHOP WEST REAL ESTATE

    83 Walker St, North Adams, MA 01247
    • 29 S Bay Rd, East Otis, MA 01029
      29 S Bay Rd, East Otis, MA 01029
      29 S Bay Rd, East Otis, MA 01029
      /27

      Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,662 Sq Ft

      29 S Bay Rd, East Otis, MA 01029

      29 S Bay Rd, East Otis, MA 01029
  • 6 Muddy Brook Cir, Great Barrington, MA 01230
    6 Muddy Brook Cir, Great Barrington, MA 01230
    6 Muddy Brook Cir, Great Barrington, MA 01230
    /56

    $1,200,000

    • 3 Beds
    • 3.5 Baths
    • 2,447 Sq Ft

    6 Muddy Brook Cir, Great Barrington, MA 01230

    Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming

    Eric Steuernagle FAIRGROUND REAL ESTATE, INC

    6 Muddy Brook Cir, Great Barrington, MA 01230
  • 41 Putnam Ave, Pittsfield, MA 01201
    41 Putnam Ave, Pittsfield, MA 01201
    41 Putnam Ave, Pittsfield, MA 01201
    /33

    $297,000 Sold Jul 08, 2025

    41 Putnam Ave, Pittsfield, MA 01201

    • 3 Beds
    • 1.5 Baths
    • 2,212 Sq Ft
    • Built 1939

    Last Sold Summary

    • 18% Below List Price
    • $134/SF
    • 109 Days On Market

    Current Estimated Value $309,609

    Last Listing Agent Ruth Goyette STEEPLEVIEW REALTY - ADAMS BRANCH

    41 Putnam Ave, Pittsfield, MA 01201
    • 40 Sylvan Rd, Monterey, MA 01245
      40 Sylvan Rd, Monterey, MA 01245
      40 Sylvan Rd, Monterey, MA 01245
      /46

      Est $2,205,600 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,600 Sq Ft

      40 Sylvan Rd, Monterey, MA 01245

      40 Sylvan Rd, Monterey, MA 01245
  • 13 Water St, Adams, MA 01220
    13 Water St, Adams, MA 01220
    13 Water St, Adams, MA 01220
    /15

    $229,000

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    13 Water St, Adams, MA 01220

    Priced below assessed value! Experience the perfect blend of comfort and outdoor charm in this beautifully updated 2-bedroom ranch home! Nestled on a double corner lot with road frontage on two streets, this property offers both privacy and accessibility. Modern and stylish flooring complements the fresh paint, making it move-in ready. 1 car garage plus 2 driveways for ample parking for you and

    Barbara DeMers NOCHER REALTY

    13 Water St, Adams, MA 01220
  • 64 Blotz Rd, Washington, MA 01223
    64 Blotz Rd, Washington, MA 01223
    64 Blotz Rd, Washington, MA 01223
    /53

    $473,000 Sold Aug 01, 2025

    64 Blotz Rd, Washington, MA 01223

    • 4 Beds
    • 2 Baths
    • 1,766 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Below List Price
    • $268/SF
    • 49 Days On Market

    Current Estimated Value $472,952

    Last Listing Agent Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

    64 Blotz Rd, Washington, MA 01223
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /36

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
  • 17 Sunnyside Dr, Dalton, MA 01226
    17 Sunnyside Dr, Dalton, MA 01226
    17 Sunnyside Dr, Dalton, MA 01226
    /44

    $374,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,196 Sq Ft

    17 Sunnyside Dr, Dalton, MA 01226

    Tucked away on a peaceful dead-end street, this spacious ranch offers comfort, style, and easy one-level living. The open living spaces feature hardwood floors, a cozy fireplace, and views to the backyard. A bonus sun-filled family room has sliders leading to the backyard, where a generous lawn and an in-ground pool provide an ideal setting for summer relaxation and entertaining.The home offers

    Molly Gillon COMPASS MASSACHUSETTS , LLC GB

    17 Sunnyside Dr, Dalton, MA 01226
  • 243 Union St Unit 301, North Adams, MA 01247
    243 Union St Unit 301, North Adams, MA 01247
    243 Union St Unit 301, North Adams, MA 01247
    /34

    $428,000 Sold Mar 07, 2025

    243 Union St Unit 301, North Adams, MA 01247

    • 2 Beds
    • 1.5 Baths
    • 2,328 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Below List Price
    • $184/SF
    • 90 Days On Market

    Current Estimated Value $448,197

    Last Listing Agent Gintare Everett ALTON & WESTALL REAL ESTATE AGENCY, LLC

    243 Union St Unit 301, North Adams, MA 01247
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /7

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
  • 10 Eastbrook Ln, Pittsfield, MA 01201
    10 Eastbrook Ln, Pittsfield, MA 01201
    10 Eastbrook Ln, Pittsfield, MA 01201
    /52

    $1,290,000

    • 5 Beds
    • 4.5 Baths
    • 3,979 Sq Ft

    10 Eastbrook Ln, Pittsfield, MA 01201

    Nestled in the lovely gated community of Woodmont Estates, this magnificent Georgian Schultz-designed home offers five bedrooms and five baths, with effortless access to all the Berkshires have to offer. Step through the elegant front entrance into a grand foyer featuring an open stairway, flanked by a formal dining room and spacious living room. Continue on to the expansive chef's kitchen,

    Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    10 Eastbrook Ln, Pittsfield, MA 01201
  • 1553 N Main Rd, Otis, MA 01253
    1553 N Main Rd, Otis, MA 01253
    1553 N Main Rd, Otis, MA 01253
    /40

    $450,000 Sold Apr 01, 2025

    1553 N Main Rd, Otis, MA 01253

    • 3 Beds
    • 2 Baths
    • 2,372 Sq Ft
    • Built 1900

    Last Sold Summary

    • 22% Below List Price
    • $190/SF
    • 147 Days On Market

    Current Estimated Value $481,798

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

    1553 N Main Rd, Otis, MA 01253
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /4

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
  • 1070 Holmes Rd, Pittsfield, MA 01201
    1070 Holmes Rd, Pittsfield, MA 01201
    1070 Holmes Rd, Pittsfield, MA 01201
    /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
  • 340 Becket Rd, Otis, MA 01253
    340 Becket Rd, Otis, MA 01253
    340 Becket Rd, Otis, MA 01253
    /20

    $508,000 Sold Nov 14, 2025

    340 Becket Rd, Otis, MA 01253

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft
    • Built 2020

    Last Sold Summary

    • 19% Below List Price
    • $313/SF
    • 121 Days On Market

    Last Listing Agent Patricia Molina Century 21 North East

    340 Becket Rd, Otis, MA 01253
    • 52 Greylock Estates Rd, Lanesborough, MA 01237
      52 Greylock Estates Rd, Lanesborough, MA 01237
      52 Greylock Estates Rd, Lanesborough, MA 01237
      /28

      Est $561,716 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,160 Sq Ft

      52 Greylock Estates Rd, Lanesborough, MA 01237

      52 Greylock Estates Rd, Lanesborough, MA 01237
  • 264 Main St Unit B, Great Barrington, MA 01230
    264 Main St Unit B, Great Barrington, MA 01230
    264 Main St Unit B, Great Barrington, MA 01230
    /26

    $425,000

    • 2 Beds
    • 1.5 Baths
    • 1,860 Sq Ft

    264 Main St Unit B, Great Barrington, MA 01230

    Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street--where every cafe, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life.Over 1,800 sq. ft. of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that

    Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    264 Main St Unit B, Great Barrington, MA 01230
  • 80 Plunkett St, Lenox, MA 01240
    80 Plunkett St, Lenox, MA 01240
    80 Plunkett St, Lenox, MA 01240
    /39

    $502,500 Sold Aug 08, 2025

    80 Plunkett St, Lenox, MA 01240

    • 3 Beds
    • 1.5 Baths
    • 1,798 Sq Ft
    • Built 1953

    Last Sold Summary

    • 1% Above List Price
    • $279/SF
    • 19 Days On Market

    Current Estimated Value $514,401

    Last Listing Agent Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    80 Plunkett St, Lenox, MA 01240
    • 57 Telephone Rd, East Otis, MA 01029
      57 Telephone Rd, East Otis, MA 01029
      57 Telephone Rd, East Otis, MA 01029
      /20

      Est $514,001 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,498 Sq Ft

      57 Telephone Rd, East Otis, MA 01029

      57 Telephone Rd, East Otis, MA 01029
  • 0 Holly Ln, Williamstown, MA 01267
    0 Holly Ln, Williamstown, MA 01267
    0 Holly Ln, Williamstown, MA 01267
    /7

    $129,900

    • Land
    • 0.51 Acre
    • $254,701 per Acre

    0 Holly Ln, Williamstown, MA 01267

    Build your dream home on the last building lot on a cul-de-sac in a highly desirable neighborhood in Williamstown. Mountain views, privacy, recently surveyed, and ready to build. Call now to schedule your appointment!

    Seth Alden ALTON & WESTALL REAL ESTATE AGENCY, LLC

    0 Holly Ln, Williamstown, MA 01267
  • 19 Summit Ave, Pittsfield, MA 01201
    19 Summit Ave, Pittsfield, MA 01201
    19 Summit Ave, Pittsfield, MA 01201
    /32

    $255,000 Sold May 01, 2025

    19 Summit Ave, Pittsfield, MA 01201

    • 3 Beds
    • 1 Bath
    • 1,160 Sq Ft
    • Built 1900

    Last Sold Summary

    • 6% Below List Price
    • $220/SF
    • 71 Days On Market

    Current Estimated Value $243,870

    Last Listing Agent Janet Benoit MOCKINGBIRD REAL ESTATE

    19 Summit Ave, Pittsfield, MA 01201
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /7

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
  • 132 Outlook Ave, Cheshire, MA 01225
    132 Outlook Ave, Cheshire, MA 01225
    132 Outlook Ave, Cheshire, MA 01225
    /50

    $549,900

    • 3 Beds
    • 2.5 Baths
    • 2,134 Sq Ft

    132 Outlook Ave, Cheshire, MA 01225

    Classic country charm awaits you in the foothills of Cheshire Massachusetts and escape home to privacy and serenity in Central Berkshire to live and play in the great outdoors. Enjoy hiking out your door and follow the Appalachian Trail even reach Mount Greylock, bike ride north and south on the Ashuwillticook Trail exercising and exploring the beautiful farmlands and countryside as you immerse

    Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

    132 Outlook Ave, Cheshire, MA 01225
  • 10 Pinto Dr, Pittsfield, MA 01201
    10 Pinto Dr, Pittsfield, MA 01201
    10 Pinto Dr, Pittsfield, MA 01201
    /49

    $624,900 Sold May 16, 2025

    10 Pinto Dr, Pittsfield, MA 01201

    • 4 Beds
    • 2.5 Baths
    • 3,198 Sq Ft
    • Built 1966

    Last Sold Summary

    • 2% Below List Price
    • $195/SF
    • 22 Days On Market

    Current Estimated Value $618,138

    Last Listing Agent Tracy Munger KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    10 Pinto Dr, Pittsfield, MA 01201

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