Berkshire, MA Homes

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  /33

  $299,900 Under Contract

  • 4 Beds
  • 1 Bath
  • 1,170 Sq Ft

  1990 East St, Pittsfield, MA 01201

  Welcome home to this inviting 4-bedroom Cape at 1990 East in Pittsfield. This charming residence offers a warm, sun-filled layout with an updated kitchen and bath that combine comfort and modern style. A brand-new deck expands your living space outdoors, creating a perfect spot for morning coffee, casual dinners, or simply unwinding at the end of the day. Thoughtfully maintained and ready to

  

  John Ciepiela

  BISHOP WEST REAL ESTATE

  (413) 486-5886

  1990 East St, Pittsfield, MA 01201
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• 

  

  

  /32

  $2,000 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Condo for Rent

  70 Livingston Ave Unit 70 Livingston, Pittsfield, MA 01201

  Welcome to 70 Livingston Ave! A two-story, well-maintained apartment/townhome in a peaceful, desirable area in southeast Pittsfield. It features:Living area, common area, kitchen, and laundry (first floor)3 bedrooms (second floor)1 bathroom (second floor)In-unit washer and dryerDishwasherAll-new window blindsUpdated modern ceiling lightsFront porch equipped

  70 Livingston Ave Unit 70 Livingston, Pittsfield, MA 01201
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  /35

  $311,000 Sold Nov 07, 2025

  519 Kirchner Rd, Dalton, MA 01226

  • 3 Beds
  • 2 Baths
  • 2,595 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Below List Price
  • $120/SF
  • 24 Days On Market

  Current Estimated Value $455,142

  Last Listing Agent The Ponte Group Keller Williams South Watuppa

  519 Kirchner Rd, Dalton, MA 01226
• 

  

  

  /7

  Not Listed For Sale

  Unlisted Address

  Unlisted Address

  Last Sold Summary

  • 2 Days On Market

  Last Sold Price $96,000

  Last Listing Agent Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC
• 

  

  

  /40

  $325,000 Pending

  • 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) 884-5511

  292 West St, Pittsfield, MA 01201
• 

  

  /9

  $450 per month

  • 2 Baths
  • 450 Sq Ft
  • Property for Rent

  34 Depot (Ste 202a) St, Pittsfield, MA 01201

  Positioned in a convenient and accessible location, this second-floor office space offers a practical and professional setting for a variety of business uses. The space features a single, well-sized office with a waiting/reception area and all utilities are included.The building includes shared restroom facilities on the same floor, along with elevator access that provides easy entry to all

  Cory Evangelisto NOCHER REALTY

  34 Depot (Ste 202a) St, Pittsfield, MA 01201
• 

  

  /35

  $365,000 Sold Dec 15, 2025

  235 Dawes Ave, Pittsfield, MA 01201

  • 3 Beds
  • 1.5 Baths
  • 1,596 Sq Ft
  • Built 1925

  Last Sold Summary

  • 3% Below List Price
  • $229/SF
  • 37 Days On Market

  Current Estimated Value $366,032

  Last Listing Agent Nick Geranios WILLIAM PITT SOTHEBY'S - LENOX

  235 Dawes Ave, Pittsfield, MA 01201
• 

  

  /25

  Est $553,124 Not Listed For Sale

  50 Branch Farm Rd, Pittsfield, MA 01201

  • 4 Beds
  • 2 Baths
  • 2,072 Sq Ft
  • Built 2007

  50 Branch Farm Rd, Pittsfield, MA 01201

  Last Sold Summary

  • 18% Above List Price
  • $227/SF
  • 4 Days On Market

  Last Sold Price $470,000

  Last Listing Agent Victoria Standring LAMACCHIA REALTY, INC
• 

  

  /39

  $325,000 Pending

  • 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
• 

  

  /6

  $1,200 total monthly price

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  43 John St Unit 2, Pittsfield, MA 01201

  This is a 1-bedroom unit. It is a second-floor apartment located in quiet neighborhood and includes stove, refrigerator. Tenant pays own utilities and it heats by electric. No pets of any kind allowed. No smoking. Ten minutes to downtown, banking, groceries, pharmacy, shopping and entertainment. On bus line. Shown by appointment. Must complete online application.

  43 John St Unit 2, Pittsfield, MA 01201
• 

  

  /55

  $267,000 Sold Nov 20, 2025

  25 Kensington Ave, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 1,426 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $187/SF
  • 49 Days On Market

  Current Estimated Value $269,670

  Last Listing Agent Chris Lipa BERKSHIRE PROPERTY MANAGERS,INC

  25 Kensington Ave, Pittsfield, MA 01201
• 

  

  /26

  Est $407,480 Not Listed For Sale

  26 Old Stockbridge Rd Unit 4, Lenox, MA 01240

  • 3 Beds
  • 2.5 Baths
  • 1,538 Sq Ft
  • Built 1870

  26 Old Stockbridge Rd Unit 4, Lenox, MA 01240

  Last Sold Summary

  • 13% Above List Price
  • $234/SF
  • 141 Days On Market

  Last Sold Price $360,000

  Last Listing Agent Susan Calkins STONE HOUSE PROPERTIES, LLC
• 

  

  /54

  $2,649,000 Under Contract

  • 6 Beds
  • 6.5 Baths
  • 4,289 Sq Ft

  250 West St, Lenox, MA 01240

  Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 423-1264

  250 West St, Lenox, MA 01240
• 

  

  /8

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 4,706 Sq Ft
  • Property for Rent

  126 Appleton Ave Unit 1, Pittsfield, MA 01201

  Recently remodeled two bedroom unit on the first floor. Refinished hardwood floors throughout along with fresh paint, new appliances, and many more updates. Heat included in rent, tenant to pay for electricity which also covers the hot water.

  Cory Evangelisto NOCHER REALTY

  126 Appleton Ave Unit 1, Pittsfield, MA 01201
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  /38

  $436,500 Sold Jun 30, 2025

  75 Alfred Dr, Pittsfield, MA 01201

  • 3 Beds
  • 2 Baths
  • 1,682 Sq Ft
  • Built 1962

  Last Sold Summary

  • 1% Below List Price
  • $260/SF
  • 14 Days On Market

  Current Estimated Value $420,131

  Last Listing Agent Robin Moore 413 REAL ESTATE

  75 Alfred Dr, Pittsfield, MA 01201
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  /79

  Est $582,465 Not Listed For Sale

  245 Francis Ave, Pittsfield, MA 01201

  • 11 Beds
  • 5 Baths
  • 5,106 Sq Ft
  • Built 1903

  245 Francis Ave, Pittsfield, MA 01201

  Last Sold Summary

  • 5% Above List Price
  • $109/SF
  • 42 Days On Market

  Last Sold Price $555,000

  Last Listing Agent Jose Goncalves 413 REAL ESTATE
• 

  /2

  $300,000 Pending

  • 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
• 

  

  /10

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 4,706 Sq Ft
  • Property for Rent

  124 Appleton Ave Unit 1, Pittsfield, MA 01201

  Recently remodeled two bedroom unit on the first floor. Refinished hardwood floors throughout along with fresh paint, new appliances, and many more updates. Heat included in rent, tenant to pay for electricity which also covers the hot water.

  Cory Evangelisto NOCHER REALTY

  124 Appleton Ave Unit 1, Pittsfield, MA 01201
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  /33

  $227,000 Sold Jul 16, 2025

  13 Oswald Ave, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft
  • Built 1933

  Last Sold Summary

  • 9% Below List Price
  • $185/SF
  • 9 Days On Market

  Current Estimated Value $230,874

  Last Listing Agent Mariah Worth LAMACCHIA REALTY, INC

  13 Oswald Ave, Pittsfield, MA 01201
• 

  

  /34

  Est $692,477 Not Listed For Sale

  79 View Dr, Pittsfield, MA 01201

  • 3 Beds
  • 2.5 Baths
  • 1,947 Sq Ft
  • Built 1960

  79 View Dr, Pittsfield, MA 01201

  Last Sold Summary

  • 7% Above List Price
  • $331/SF
  • 7 Days On Market

  Last Sold Price $645,000

  Last Listing Agent Jared Kelly William Pitt
• 

  

  /8

  $1,719,000

  • 37 Beds
  • 24 Baths
  • 21,162 Sq Ft

  306 South St, Pittsfield, MA 01201

  Offered as a 7-property portfolio, totaling 21 units, this package includes a mix of multifamily properties and a single-family home with value-add potential. Several units are tenant-occupied, providing immediate income with upside potential, while others units require renovation, allowing investors to implement a phased improvement strategy. The portfolio currently generates an in-place NOI of

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 798-8328

  306 South St, Pittsfield, MA 01201
• 

  

  /26

  $12,000 per month

  • 2 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • House for Rent

  45 Taconic Ave, Lenox, MA 01240

  Experience the ultimate Summer in Lenox! This fully restored carriage house is available from June 28 - July 30, offering a prime walk-to-town location just minutes from Tanglewood. Inside, enjoy a light-filled great room with cathedral ceilings, a gas fireplace, and a chef's kitchen. This 2-bed, 2-bath retreat features a first-floor primary suite, hardwood floors, and a brand-new second-floor

  John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  45 Taconic Ave, Lenox, MA 01240
• 

  

  /23

  $355,000 Sold Jul 15, 2025

  9 Rolling Hills Unit 5, Lenox, MA 01240

  • 2 Beds
  • 3 Baths
  • 1,552 Sq Ft
  • Built 1976

  Last Sold Summary

  • $229/SF
  • 3 Days On Market

  Last Listing Agent Susan Baum BERKSHIRE HOMES AND CONDOS

  9 Rolling Hills Unit 5, Lenox, MA 01240
• 

  

  /20

  Est $263,619 Not Listed For Sale

  23 Day St, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 988 Sq Ft
  • Built 1955

  23 Day St, Pittsfield, MA 01201

  Last Sold Summary

  • 9% Above List Price
  • $244/SF
  • 5 Days On Market

  Last Sold Price $241,000

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

  

  /97

  $349,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 4,009 Sq Ft

  514 South St, Pittsfield, MA 01201

  Set along one of Pittsfield's historic corridors, this circa 1815 Federal-style estate offers a compelling study in early American architecture, enduring design, and modern potential. Once a vibrant estate, the property still echoes its past, where landscaping and period lighting brought warmth and presence to the grounds. Inside, a quiet air of English refinement unfolds. Neoclassical detailing

  

  Syrah Bradley

  BISHOP WEST REAL ESTATE

  (413) 722-5807

  514 South St, Pittsfield, MA 01201
• 

  

  /23

  $2,300 per month

  • Condo for Rent

  18 Morgan St Unit 1, Lenox, MA 01240

  Fully renovated, fully furnished, like new Studio Apartment with 1 full bath. Must be seen to be appreciated. Location, location, location. It does not get any better than this. Just minutes from the heart of downtown Lenox and the world class music at Tanglewood. Features include modern finishes and a rare private garage stall.

  Jim Moir WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  18 Morgan St Unit 1, Lenox, MA 01240
• 

  

  /27

  $430,000 Sold Aug 22, 2025

  377 Pomeroy Ave, Pittsfield, MA 01201

  • 3 Beds
  • 2.5 Baths
  • 2,125 Sq Ft
  • Built 1950

  Last Sold Summary

  • 4% Below List Price
  • $202/SF
  • 20 Days On Market

  Current Estimated Value $437,305

  Last Listing Agent Franz Forster FRANZ J. FORSTER R. E.

  377 Pomeroy Ave, Pittsfield, MA 01201
• 

  

  /34

  Est $265,737 Not Listed For Sale

  97 Bay State Rd, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 1,428 Sq Ft
  • Built 1930

  97 Bay State Rd, Pittsfield, MA 01201

  Last Sold Summary

  • 9% Above List Price
  • $171/SF
  • 12 Days On Market

  Last Sold Price $244,500

  Last Listing Agent Doug Collins Lamacchia Realty, Inc.
• 

  

  /47

  $650,000

  • 5 Beds
  • 3.5 Baths
  • 3,074 Sq Ft

  161 Leona Dr, Pittsfield, MA 01201

  Set in one of Southeast Pittsfield's most desirable neighborhoods, this very sunny and impeccably maintained home offers the perfect balance of gracious living, flexible space, and effortless entertaining. Lovingly cared for by its current owner, the home unfolds with elegant formal rooms, hardwood floors, and a warm wood burning fireplace anchoring the living room. The heart of the home is an

  

  Nick Geranios

  WILLIAM PITT SOTHEBY'S - LENOX

  (413) 570-8931

  161 Leona Dr, Pittsfield, MA 01201
• 

  

  /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
• 

  

  /22

  $268,000 Sold Jun 17, 2025

  56 Velma Ave, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft
  • Built 1955

  Last Sold Summary

  • $282/SF
  • 11 Days On Market

  Current Estimated Value $268,519

  Last Listing Agent Angel Black KRG - Key Realty Group

  56 Velma Ave, Pittsfield, MA 01201
• 

  

  /16

  Est $220,275 Not Listed For Sale

  88 Daniels Ave, Pittsfield, MA 01201

  • 3 Beds
  • 1.5 Baths
  • 1,580 Sq Ft
  • Built 1900

  88 Daniels Ave, Pittsfield, MA 01201

  Last Sold Summary

  • 16% Above List Price
  • $120/SF
  • 5 Days On Market

  Last Sold Price $189,900

  Last Listing Agent Oana Boucher ALL SEASONS REALTY GROUP
• 

  

  /42

  $1,280,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 4.5 Baths
  • 2,691 Sq Ft

  18 Highcrest Rd Unit 20, Lenox, MA 01240

  

  Selina Lamb

  Birch Properties

  (413) 591-5654

  18 Highcrest Rd Unit 20, Lenox, MA 01240
• 

  

  /18

  $500 per month

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

  212 South St, Pittsfield, MA 01201

  Incredible location for your business. Corner of South and Henry ave. just a short walk south of the busy North Street corridor. Four office spaces for lease. Rates are as follows: (Suite 1: 170 sq.ft./$700 mo., Suite 2: 100 sq.ft./$600 mo., Suite 3: 90 sq.ft./$500 mo., Suite 4: 250 sq.ft./$800/mo.) All utilities, including internet, is included. Private, off-street parking.

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  212 South St, Pittsfield, MA 01201
• 

  

  /36

  $237,000 Sold Nov 18, 2025

  24 Lebanon Ave, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 1,449 Sq Ft
  • Built 1925

  Last Sold Summary

  • 18% Below List Price
  • $164/SF
  • 56 Days On Market

  Current Estimated Value $246,967

  Last Listing Agent Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX

  24 Lebanon Ave, Pittsfield, MA 01201
• 

  

  /26

  Est $352,118 Not Listed For Sale

  71 S Church St Unit S301, Pittsfield, MA 01201

  • 2 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • Built 2008

  71 S Church St Unit S301, Pittsfield, MA 01201

  Last Sold Summary

  • 15% Above List Price
  • $223/SF
  • 56 Days On Market

  Last Sold Price $305,000

  Last Listing Agent Elle Villetto William Pitt
• 

  

  /43

  $350,000 Pending

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

  612 E New Lenox Rd, Pittsfield, MA 01201

  Welcome to this move in ready embankment ranch in a desirable southeast neighborhood! This home has been loved by one family for the last 50 years, and is now ready to host a new family! Come see the beautiful hardwood floors in the large living room and all 3 bedrooms. Two of the bedrooms have large cedar-lined closets. The eat-in kitchen has ample cabinet space with easy access to the attached

  Juli Kowach LAMACCHIA REALTY, INC

  612 E New Lenox Rd, Pittsfield, MA 01201
• 

  

  /23

  $3,500 per month

  • 2 Beds
  • 2.5 Baths
  • 1,867 Sq Ft
  • House for Rent

  34 Galway Ct, Lenox, MA 01240

  Perfectly located within 10 minutes to Tanglewood, this all one floor Ranch home is fully furnished and nicely appointed. The Galway Court neighborhood experiences limited traffic situations while making the trip to the center of Lenox and its shops and restaurants an easy bike ride for anyone so inclined. Like to golf? The Miraval Country Club is just five minutes away. The house features a very

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  34 Galway Ct, Lenox, MA 01240
• 

  

  /28

  $225,000 Sold Mar 05, 2026

  326 Dalton Ave, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft
  • Built 1940

  Last Sold Summary

  • 22% Below List Price
  • $184/SF
  • 357 Days On Market

  Current Estimated Value $259,673

  Last Listing Agent Jessie Downer LAMACCHIA REALTY, INC

  326 Dalton Ave, Pittsfield, MA 01201
• 

  

  /56

  Est $622,831 Not Listed For Sale

  20 Warwick St, Pittsfield, MA 01201

  • 3 Beds
  • 3.5 Baths
  • 1,845 Sq Ft
  • Built 1957

  20 Warwick St, Pittsfield, MA 01201

  Last Sold Summary

  • 12% Above List Price
  • $301/SF
  • 3 Days On Market

  Last Sold Price $555,000

  Last Listing Agent Jessica Rizzo LAMACCHIA REALTY, INC

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