17,565

Pittsfield, MA Homes

Section Image
  • /46

    $630,000

    Sold May 14, 2026

    103 Gravesleigh Terrace, Pittsfield, MA 01201

    • 3 Beds
    • 3 Baths
    • 2,699 Sq Ft
    • Built 1982

    Last Sold Summary

    • 2% Below List Price
    • $233/SF
    • 7 Days On Market

    Current Estimated Value $649,434

    Last Listing Agent Claire Pollart WILLIAM RAVEIS - BERKSHIRE

    103 Gravesleigh Terrace, Pittsfield, MA 01201
    • /32

      Est $305,797

      Not Listed For Sale

      34 Sampson Pkwy, Pittsfield, MA 01201

      • 2 Beds
      • 1 Bath
      • 1,086 Sq Ft
      • Built 1948
      34 Sampson Pkwy, Pittsfield, MA 01201

      Last Sold Summary

      • 4 Days On Market

  • /58

    $549,900

    • 4 Beds
    • 3 Baths
    • 2,670 Sq Ft

    48 Brookside Dr, Pittsfield, MA 01201

    Meticulously maintained and lovingly cared for, this spacious four-bedroom, two-and-a-half-bath home offers the perfect combination of comfort, quality, and location. Featuring generously sized rooms throughout, this home provides ample space for both everyday living and entertaining. Pristine wood floors lie beneath the carpeting, offering the opportunity to uncover their timeless beauty. Recent

    Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    48 Brookside Dr, Pittsfield, MA 01201
  • /43

    $330,000

    Sold Feb 17, 2026

    612 E New Lenox Rd, Pittsfield, MA 01201

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1963

    Last Sold Summary

    • 8% Below List Price
    • $295/SF
    • 66 Days On Market

    Current Estimated Value $348,260

    Last Listing Agent Juli Kowach Lamacchia Realty, Inc. - Dalton

    612 E New Lenox Rd, Pittsfield, MA 01201
    • /33

      Est $348,548

      Not Listed For Sale

      83 W Union St, Pittsfield, MA 01201

      • 6 Beds
      • 3 Baths
      • 2,340 Sq Ft
      • Built 1900
      83 W Union St, Pittsfield, MA 01201

      Last Sold Summary

      • 19 Days On Market

  • /35

    $259,900

    Pending
    • 6 Beds
    • 3 Baths
    • 3,200 Sq Ft

    165 Appleton Ave, Pittsfield, MA 01201

    Classic two family brick colonial with many possibilities! Including a front/rear porch, two separate yards on each side, and off street parking. Enter each side into a wide, open hallway with the original hardwood floors throughout. The left side has four bedrooms and one bathroom with potential for a second bathroom off the kitchen. The right side has been split into two smaller units with

    Cory Evangelisto NOCHER REALTY

    165 Appleton Ave, Pittsfield, MA 01201
  • /27

    $250,000

    Sold Nov 05, 2025

    174 Cole Ave, Pittsfield, MA 01201

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1960

    Last Sold Summary

    • 5% Below List Price
    • $217/SF
    • 6 Days On Market

    Current Estimated Value $261,993

    Last Listing Agent Shannon Santelli KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    174 Cole Ave, Pittsfield, MA 01201
    • /13

      Est $216,954

      Not Listed For Sale

      217 Bradford St, Pittsfield, MA 01201

      • 5 Beds
      • 2 Baths
      • 2,160 Sq Ft
      • Built 1910
      217 Bradford St, Pittsfield, MA 01201

      Last Sold Summary

      • 18 Days On Market

  • /31

    $274,900

    $25K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,184 Sq Ft

    142 Benedict Rd, Pittsfield, MA 01201

    Well-maintained 1930 Colonial that has been cared for by its longtime owners for decades. This home features three spacious bedrooms, hardwood floors, abundant natural sunlight, and a functional layout with comfortable living spaces throughout, including a formal dining room. The front entrance offers a spacious enclosed porch, providing additional living or sitting space. The kitchen includes a

    Tracy Munger KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    142 Benedict Rd, Pittsfield, MA 01201
  • /85

    $296,500

    Sold Jun 25, 2026

    22 Broadway St, Pittsfield, MA 01201

    • 3 Beds
    • 1 Bath
    • 1,634 Sq Ft
    • Built 1920

    Last Sold Summary

    • 2% Above List Price
    • $181/SF
    • 5 Days On Market

    Current Estimated Value $286,375

    Last Listing Agent Chris LaPatin Lamacchia Realty, Inc. - Dalton

    22 Broadway St, Pittsfield, MA 01201
    • /47

      Est $311,788

      Not Listed For Sale

      81 Longview Terrace, Pittsfield, MA 01201

      • 3 Beds
      • 1 Bath
      • 1,250 Sq Ft
      • Built 1955
      81 Longview Terrace, Pittsfield, MA 01201

      Last Sold Summary

      • 117 Days On Market

  • /24

    $399,500

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,640 Sq Ft

    38 Revere Pkwy, Pittsfield, MA 01201

    Pristine Colonial located in desirable Southeast Pittsfield, featuring a newly renovated kitchen and updated half bath. This well-maintained home offers a wonderful, easy flow with three generously sized bedrooms. Enjoy the comfort of a cozy office just off the living room, along with a beautiful wood-burning fireplace. Truly move-in ready--just unpack and enjoy!

    Tanya Shepardson Lamacchia Realty, Inc. - Dalton

    38 Revere Pkwy, Pittsfield, MA 01201
  • /17

    $415,000

    Sold Mar 10, 2026

    86 Winesap Rd, Pittsfield, MA 01201

    • 3 Beds
    • 3 Baths
    • 2,299 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Below List Price
    • $181/SF
    • 26 Days On Market

    Current Estimated Value $413,653

    Last Listing Agent Elisha Poirier STONE HOUSE PROPERTIES, LLC

    86 Winesap Rd, Pittsfield, MA 01201
    • /16

      Est $244,388

      Not Listed For Sale

      226 Lenox Ave, Pittsfield, MA 01201

      • 2 Beds
      • 1 Bath
      • 879 Sq Ft
      • Built 1926
      226 Lenox Ave, Pittsfield, MA 01201

      Last Sold Summary

      • 47 Days On Market

  • /12

    $160,000

    • 6 Beds
    • 2 Baths
    • 2,128 Sq Ft

    242 Wahconah St, Pittsfield, MA 01201

    Investor Special! This gutted duplex offers a blank canvas with 6 bedrooms, 2 bathrooms, and 2,000 sqft of space, plus the possibility of additional living space in the attic. this property features a large backyard with a serene water stream, A standing garage remains on site for additional storage or future use. Situated on a 13,108 sqft lot, can also be bundled with 40 Pecks Rd & 48 Brown st

    Xavier Cruz Fathom Realty

    242 Wahconah St, Pittsfield, MA 01201
  • /35

    $230,000

    Sold Aug 06, 2025

    186 Lenox Ave, Pittsfield, MA 01201

    • 3 Beds
    • 1.5 Baths
    • 1,608 Sq Ft
    • Built 1950

    Last Sold Summary

    • 16% Above List Price
    • $143/SF
    • 5 Days On Market

    Current Estimated Value $243,680

    Last Listing Agent Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

    186 Lenox Ave, Pittsfield, MA 01201
    • /52

      Est $752,807

      Not Listed For Sale

      29 Aspen Way, Pittsfield, MA 01201

      • 5 Beds
      • 3 Baths
      • 3,030 Sq Ft
      • Built 2005
      29 Aspen Way, Pittsfield, MA 01201

      Last Sold Summary

      • 2 Days On Market

  • /28

    $189,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft

    395 Cheshire Rd Unit 102, Pittsfield, MA 01201

    You can truly relax and enjoy life here, as this brand-new, thoughtfully crafted home in Pittsfield's premier community lets you skip the maintenance worries of an older house.The open-concept layout is bright and inviting, perfectly connecting your spacious living area to a lovely, modern kitchen. With three bedrooms and two full baths, there is plenty of room. You'll also love the

    Jason Nocher NOCHER REALTY

    395 Cheshire Rd Unit 102, Pittsfield, MA 01201
  • /51

    $545,000

    Sold Feb 06, 2026

    39 Lexington Pkwy, Pittsfield, MA 01201

    • 4 Beds
    • 2 Baths
    • 2,574 Sq Ft
    • Built 1932

    Last Sold Summary

    • 6% Below List Price
    • $212/SF
    • 116 Days On Market

    Current Estimated Value $557,695

    Last Listing Agent Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

    39 Lexington Pkwy, Pittsfield, MA 01201
    • /39

      Est $718,757

      Not Listed For Sale

      67 Flintstone Dr, Pittsfield, MA 01201

      • 3 Beds
      • 3.5 Baths
      • 2,900 Sq Ft
      • Built 1988
      67 Flintstone Dr, Pittsfield, MA 01201

      Last Sold Summary

      • 3 Days On Market

  • /47

    $398,500

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft

    97 Morningview Dr, Pittsfield, MA 01201

    Pride of ownership shines throughout this beautifully updated ranch situated on a corner lot in a walkable, sought-after neighborhood, close to bike trails, hiking and shopping. This well maintained 3-bedroom, 2 full bath home features central air, a bright modern kitchen with Instaview refrigerator, double oven, 2 filtered water sites and a spacious dining area with cathedral ceiling. The

    Matt Jarck WILLIAM PITT SOTHEBY'S - LENOX

    97 Morningview Dr, Pittsfield, MA 01201
  • /25

    $242,500

    Sold Jan 16, 2026

    87 Maryland Ave, Pittsfield, MA 01201

    • 2 Beds
    • 1 Bath
    • 1,014 Sq Ft
    • Built 1942

    Last Sold Summary

    • 3% Below List Price
    • $239/SF
    • 12 Days On Market

    Current Estimated Value $253,335

    Last Listing Agent Andreea Duta BISHOP WEST REAL ESTATE

    87 Maryland Ave, Pittsfield, MA 01201
    • /37

      Est $226,038

      Not Listed For Sale

      81 Dartmouth St Unit 302, Pittsfield, MA 01201

      • 2 Beds
      • 1 Bath
      • 961 Sq Ft
      • Built 1927
      81 Dartmouth St Unit 302, Pittsfield, MA 01201

      Last Sold Summary

      • 8 Days On Market

  • /27

    $355,000

    • 5 Beds
    • 4 Baths
    • 5,070 Sq Ft

    29 Linden St, Pittsfield, MA 01201

    Downtown Creative District Investment Opportunity Positioned in the heart of Pittsfield's vibrant Downtown Creative District, this fully occupied and professionally managed four-family property offers investors a rare blend of stable income and exceptional location. Just steps from the renowned Barrington Stage Company, residents enjoy easy access to some of the city's best entertainment, dining,

    Tim Gallagher STONE HOUSE PROPERTIES, LLC

    29 Linden St, Pittsfield, MA 01201
  • /26

    $319,000

    Sold Nov 21, 2025

    288 Bradford St, Pittsfield, MA 01201

    • 7 Beds
    • 4 Baths
    • 2,848 Sq Ft
    • Built 1880

    Last Sold Summary

    • 5% Below List Price
    • $112/SF
    • 7 Days On Market

    Last Listing Agent Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

    288 Bradford St, Pittsfield, MA 01201
    • /46

      Est $702,386

      Not Listed For Sale

      39 Tamie Way, Pittsfield, MA 01201

      • 4 Beds
      • 4 Baths
      • 3,790 Sq Ft
      • Built 1996
      39 Tamie Way, Pittsfield, MA 01201

      Last Sold Summary

      • 35 Days On Market

  • /57

    $349,900

    Pending
    • 7 Beds
    • 2.5 Baths
    • 2,870 Sq Ft

    5 Monteleone Place, Pittsfield, MA 01201

    Large side-by-side two family brick home with a total of 6 garage bays. The home comes with an attached 2-car garage plus a detached 4-bay garage. Unit 6 is vacant and has been renovated. The first floor offers an enclosed porch, new beautiful kitchen with quartz countertops and stainless appliances, dining room, living room and full bathroom. The layout offers a possibility to turn one of the

    Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    5 Monteleone Place, Pittsfield, MA 01201
  • /25

    $95,000

    Sold Jun 26, 2026

    3 Lakewood Cir, Pittsfield, MA 01201

    • 3 Beds
    • 2 Baths
    • 970 Sq Ft
    • Built 2006

    Last Sold Summary

    • 4% Below List Price
    • $98/SF
    • 16 Days On Market

    Last Listing Agent Janet Benoit MOCKINGBIRD REAL ESTATE

    3 Lakewood Cir, Pittsfield, MA 01201
    • /45

      Est $315,933

      Not Listed For Sale

      38 Birch Grove Dr, Pittsfield, MA 01201

      • 3 Beds
      • 1.5 Baths
      • 1,260 Sq Ft
      • Built 1951
      38 Birch Grove Dr, Pittsfield, MA 01201

      Last Sold Summary

      • 5 Days On Market

  • /40

    $214,900

    • 2 Beds
    • 1 Bath
    • 1,028 Sq Ft

    33 Maplewood Ave Unit 103, Pittsfield, MA 01201

    If you are looking for easy one-level living - don't miss this opportunity! The Maplewood is an elegant condo conversion consisting of eighteen units centrally located in downtown Pittsfield. You'll enjoy this light-filled corner/end unit on the first floor. High ceilings and an open-living plan give a very spacious feel to this two-bedroom unit. Kitchen with granite and stainless, hardwood

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    33 Maplewood Ave Unit 103, Pittsfield, MA 01201
  • /49

    $274,900

    Sold Jan 02, 2026

    64 Brooks Ave, Pittsfield, MA 01201

    • 3 Beds
    • 1 Bath
    • 1,240 Sq Ft
    • Built 1920

    Last Sold Summary

    • $222/SF
    • 26 Days On Market

    Current Estimated Value $279,112

    Last Listing Agent Chris Lipa BERKSHIRE PROPERTY MANAGERS,INC

    64 Brooks Ave, Pittsfield, MA 01201
    • /17

      Est $223,401

      Not Listed For Sale

      12 Pond St, Pittsfield, MA 01201

      • 4 Beds
      • 2 Baths
      • 1,831 Sq Ft
      • Built 1890
      12 Pond St, Pittsfield, MA 01201

      Last Sold Summary

      • 6 Days On Market

  • /50

    $569,900

    $30K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,561 Sq Ft

    2 Amy Ct Unit 2, Pittsfield, MA 01201

    Stunning and beautifully designed three-level end unit condominium with luxury finishes throughout. Enter into an open-concept main level, highlighted by gleaming hardwood floors, recessed lighting, and expansive windows that flood the space with natural light. The kitchen offers stainless steel appliances, granite countertops, and custom cabinetry. The spacious living and dining areas are

    Cory Evangelisto NOCHER REALTY

    2 Amy Ct Unit 2, Pittsfield, MA 01201
  • /30

    $265,000

    Sold Aug 05, 2025

    12 Boison St, Pittsfield, MA 01201

    • 3 Beds
    • 1.5 Baths
    • 1,498 Sq Ft
    • Built 1930

    Last Sold Summary

    • 2% Above List Price
    • $177/SF
    • 18 Days On Market

    Current Estimated Value $293,769

    Last Listing Agent Doug Collins Lamacchia Realty, Inc. - Dalton

    12 Boison St, Pittsfield, MA 01201
    • /30

      Est $306,709

      Not Listed For Sale

      37 Elaine Dr, Pittsfield, MA 01201

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1962
      37 Elaine Dr, Pittsfield, MA 01201

      Last Sold Summary

      • 9 Days On Market

  • /29

    $1,900,000

    Pending
    • 28 Beds
    • 14 Baths
    • 14,280 Sq Ft

    401 Wahconah St, Pittsfield, MA 01201

    Rare Investment Opportunity: 14-Unit Residential PortfolioWhy buy just one multi-family investment property when you can own the whole neighborhood?Presenting a truly unique real estate package: seven contiguous duplexes situated on their own private street in Pittsfield. This portfolio offers a total of 14 high-demand apartments, providing immediate scale and streamlined management for the savvy

    Timothy Johnson NOCHER REALTY

    401 Wahconah St, Pittsfield, MA 01201
  • /45

    $430,500

    Sold Mar 03, 2026

    17 Kittredge Rd, Pittsfield, MA 01201

    • 4 Beds
    • 2.5 Baths
    • 2,430 Sq Ft
    • Built 1949

    Last Sold Summary

    • 4% Below List Price
    • $177/SF
    • 102 Days On Market

    Current Estimated Value $455,688

    Last Listing Agent Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

    17 Kittredge Rd, Pittsfield, MA 01201
    • /39

      Est $417,687

      Not Listed For Sale

      50 Longview Terrace, Pittsfield, MA 01201

      • 3 Beds
      • 2.5 Baths
      • 2,107 Sq Ft
      • Built 1955
      50 Longview Terrace, Pittsfield, MA 01201

      Last Sold Summary

      • 3 Days On Market

  • /52

    $799,000

    $26K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,400 Sq Ft

    26 Westbrook Terrace, Pittsfield, MA 01201

    Set on 3.04 acres across two lots abutting protected land, this Executive Ranch is the only single-level home in the gated community of Woodmont Estates. 3,400 sq ft of expansive, easy living, featuring 4bd/2.5ba, a renovated primary bath, updated kitchen, and light-filled four-season sunroom w/ new Andersen windows. Designed for comfort & flexibility, the layout includes a private office, as

    THE KAHN TEAM BISHOP WEST REAL ESTATE

    26 Westbrook Terrace, Pittsfield, MA 01201
  • /46

    $365,000

    Sold Dec 09, 2025

    36 Chickering St, Pittsfield, MA 01201

    • 6 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • Built 1900

    Last Sold Summary

    • 6% Below List Price
    • $114/SF
    • 78 Days On Market

    Current Estimated Value $373,457

    Last Listing Agent Chris LaPatin Lamacchia Realty, Inc. - Dalton

    36 Chickering St, Pittsfield, MA 01201

Showing Results 441 - 480, Page 12 of 18

How to Buy a Home How to Finance a Home How to Sell a Home