Pittsfield, MA Homes

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  /20

  $235,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,377 Sq Ft

  53 Churchill Crest Unit 53, Pittsfield, MA 01201

  Coveted end unit with vaulted ceiling, deck and western views to private pool and hills beyond. Two full baths, garage, high quality window treatments, light fixtures and ceiling fan. Dramatic stone fireplace with Pellet stove. Flower garden. Very desirable unit in a safe, quiet, beautifully maintained association!

  Henry Hagenah OCTOBER MOUNTAIN REAL ESTATE

  53 Churchill Crest Unit 53, Pittsfield, MA 01201
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  /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 $238,382

  Last Listing Agent Laiken Rapisarda LAMACCHIA REALTY, INC

  186 Lenox Ave, Pittsfield, MA 01201
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  /30

  Est $318,103 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

  • 18% Above List Price
  • $268/SF
  • 9 Days On Market

  Last Sold Price $270,000

  Last Listing Agent Katie Soules WILLIAM RAVEIS REAL ESTATE
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  /51

  $369,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  195 Churchill St, Pittsfield, MA 01201

  Showings start on Friday Feb 27th. Don't overlook this updated move-in ready embankment ranch! Country setting yet minutes to downtown. The main level includes three bedrooms; living room with hardwood flooring and fireplace. The kitchen is updated with plenty of room for eat-in. Think spring! Kitchen sliders open to private rear deck with motorized awning. Off the kitchen a seasonal sunroom

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  195 Churchill St, Pittsfield, MA 01201
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  /50

  $660,000 Sold Jul 01, 2025

  22 Kathy Way, Pittsfield, MA 01201

  • 3 Beds
  • 2.5 Baths
  • 3,020 Sq Ft
  • Built 2018

  Last Sold Summary

  • $219/SF
  • 3 Days On Market

  Current Estimated Value $677,286

  Last Listing Agent Cindy Carrigan LAMACCHIA REALTY, INC

  22 Kathy Way, Pittsfield, MA 01201
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  /39

  Est $452,013 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

  • 5% Above List Price
  • $204/SF
  • 3 Days On Market

  Last Sold Price $430,000

  Last Listing Agent Doug Collins LAMACCHIA REALTY, INC
• 

  

  /31

  $159,900 Under Contract

  • 1 Bed
  • 1 Bath
  • 544 Sq Ft

  81 Dartmouth St Unit 108, Pittsfield, MA 01201

  Welcome to this beautifully maintained 1-bedroom, 1-bath condo located in the sought-after Crane Park Condos. This thoughtfully designed unit features an open-concept layout with granite countertops, stainless steel appliances, a gas range, travertine tile flooring, and charming shiplap ceilings. The spacious bedroom offers bamboo flooring, generous closet space, and overlooks the living area for

  Sai Kamasani LAMACCHIA REALTY, INC

  81 Dartmouth St Unit 108, Pittsfield, MA 01201
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  /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 $243,232

  Last Listing Agent Andreea Duta BISHOP WEST REAL ESTATE

  87 Maryland Ave, Pittsfield, MA 01201
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  /40

  Est $661,614 Not Listed For Sale

  51 Holmes Rd, Pittsfield, MA 01201

  • 4 Beds
  • 2.5 Baths
  • 3,145 Sq Ft
  • Built 1880

  51 Holmes Rd, Pittsfield, MA 01201

  Last Sold Summary

  • 15% Above List Price
  • $183/SF
  • 7 Days On Market

  Last Sold Price $575,000

  Last Listing Agent Danielle Giulian William Pitt
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  /39

  $285,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft

  16 Leona Dr, Pittsfield, MA 01201

  Located in the highly desirable Southeast Pittsfield neighborhood, this 3-bedroom, 2-bath home offers tremendous potential for buyers ready to add their personal touch. The main level features beautiful hardwood floors, a spacious living room filled with natural light, a formal dining room, three comfortable bedrooms, and a full bath. The lower level provides valuable additional space, a laundry

  Jose Larios LAMACCHIA REALTY, INC

  16 Leona Dr, Pittsfield, MA 01201
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  /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

  288 Bradford St, Pittsfield, MA 01201
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  /39

  Est $291,820 Not Listed For Sale

  433 Lebanon Ave, Pittsfield, MA 01201

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft
  • Built 1950

  433 Lebanon Ave, Pittsfield, MA 01201

  Last Sold Summary

  • 10% Above List Price
  • $287/SF
  • 6 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Shannon Regan KEY REALTY
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  /2

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  233 Cadwell Rd, Pittsfield, MA 01201

  Two-family home set on just under 1.5 acres offering the perfect blend of country living and city convenience. Each unit features decks overlooking a spacious backyard, ideal for relaxing or entertaining. Enjoy the privacy and open space while still being just minutes from city amenities, shopping, and dining. A great opportunity for owner-occupants or investors--live in one unit and rent the

  Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals

  233 Cadwell Rd, Pittsfield, MA 01201
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  /35

  $378,000 Sold May 30, 2025

  3 Caroline St, Pittsfield, MA 01201

  • 3 Beds
  • 2.5 Baths
  • 1,300 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Above List Price
  • $291/SF
  • 18 Days On Market

  Current Estimated Value $370,959

  Last Listing Agent Laura Arseneau PAULA MCLEAN REALTORS INC.

  3 Caroline St, Pittsfield, MA 01201
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  /35

  Est $269,878 Not Listed For Sale

  171 Connecticut Ave, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1950

  171 Connecticut Ave, Pittsfield, MA 01201

  Last Sold Summary

  • 12% Above List Price
  • $240/SF
  • 41 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Mark Harris SIGNATURE ASSOCIATES
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  /38

  $179,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 890 Sq Ft

  22 S Atlantic Ave, Pittsfield, MA 01201

  Welcome to this updated & affordable home in the heart of Pittsfield. Offering 3 bedrooms, including a convenient first-floor bedroom; a renovated bathroom, & an updated eat-in kitchen, this home blends comfort, flexibility, and everyday functionality. First-floor laundry adds to the ease of living, & with the updates already completed, you can move right in with confidence.Outside, you'll

  Jessie Downer LAMACCHIA REALTY, INC

  22 S Atlantic Ave, Pittsfield, MA 01201
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  /3

  $70,000 Sold Mar 31, 2025

  245 Cheshire Rd Unit 14, Pittsfield, MA 01201

  • 2 Beds
  • 1 Bath
  • 1,416 Sq Ft
  • Built 1980

  Last Sold Summary

  • 8% Above List Price
  • $49/SF
  • 13 Days On Market

  Last Listing Agent Comparable Listing COMPARABLE LISTING ONLY

  245 Cheshire Rd Unit 14, Pittsfield, MA 01201
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  /23

  Est $316,584 Not Listed For Sale

  5 Ring St, Pittsfield, MA 01201

  • 4 Beds
  • 2 Baths
  • 1,911 Sq Ft
  • Built 1949

  5 Ring St, Pittsfield, MA 01201

  Last Sold Summary

  • 26% Above List Price
  • $131/SF
  • 1 Day On Market

  Last Sold Price $251,000

  Last Listing Agent Robin Moore 413 REAL ESTATE
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  /27

  $265,000

  • 4 Beds
  • 2 Baths
  • 1,408 Sq Ft

  17 S Church St, Pittsfield, MA 01201

  Spacious and freshly updated West Side single-family offering 4 bedrooms and 2 full baths across 1,408 sq ft. Bright, functional layout with generous room sizes, fresh interior paint, and new laminate flooring throughout. Modern kitchen features brand-new appliances and clean, updated finishes. Enjoy a charming wraparound porch with dual entry, ideal for relaxing or entertaining, plus a level

  Samantha Homeyer BIRCH PROPERTIES

  17 S Church St, Pittsfield, MA 01201
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  /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 $270,563

  Last Listing Agent Chris Lipa BERKSHIRE PROPERTY MANAGERS,INC

  64 Brooks Ave, Pittsfield, MA 01201
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  /2

  Est $290,033 Not Listed For Sale

  88 Taylor St, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 1,638 Sq Ft
  • Built 1951

  88 Taylor St, Pittsfield, MA 01201

  Last Sold Summary

  • 17% Above List Price
  • $151/SF
  • 108 Days On Market

  Last Sold Price $248,000

  Last Listing Agent Nick Geranios William Pitt
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  /36

  $399,000

  • 3 Beds
  • 1 Bath
  • 1,284 Sq Ft

  162 Bull Hill Rd, Pittsfield, MA 01201

  Pride of ownership shines throughout this well-cared-for property offering lake rights and a long list of meaningful improvements spanning nearly two decades. Inside, you'll find a home that's been continuously upgraded with a remodeled kitchen and bathroom, updated windows, including a bright bay window in the living room. Both the boiler and roof have been replaced. The three-season room adds

  Christopher Moon LAMACCHIA REALTY, INC

  162 Bull Hill Rd, Pittsfield, MA 01201
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  /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 $271,536

  Last Listing Agent Doug Collins LAMACCHIA REALTY, INC

  12 Boison St, Pittsfield, MA 01201
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  /68

  Est $613,979 Not Listed For Sale

  38 Shetland Dr, Pittsfield, MA 01201

  • 4 Beds
  • 2.5 Baths
  • 2,624 Sq Ft
  • Built 1973

  38 Shetland Dr, Pittsfield, MA 01201

  Last Sold Summary

  • 15% Above List Price
  • $204/SF
  • 21 Days On Market

  Last Sold Price $535,000

  Last Listing Agent Tracy Munger KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
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  /17

  $204,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,496 Sq Ft

  25 Ashley St, Pittsfield, MA 01201

  Nestled in a quiet, well-established neighborhood, this dated yet full of character property offers the perfect canvas for those with vision and creativity. While the home has maintained its original charm, it presents an exciting opportunity to modernize and make it your own.The floor plan features architectural details that can be restored or updated to suit your personal style. With some TLC

  Timothy Disilva SUMMIT REALTY

  25 Ashley St, Pittsfield, MA 01201
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  /10

  $92,000 Sold May 28, 2025

  41 Shaker Ln, Pittsfield, MA 01201

  • Land
  • 3.9 Acres
  • $23,590 per Acre

  Last Sold Summary

  • 31% Below List Price
  • 144 Days On Market

  Current Estimated Value $94,728

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

  41 Shaker Ln, Pittsfield, MA 01201
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  /35

  Est $1,417,764 Not Listed For Sale

  210 E Slope Rd, Pittsfield, MA 01201

  • 4 Beds
  • 3.5 Baths
  • 3,006 Sq Ft
  • Built 1975

  210 E Slope Rd, Pittsfield, MA 01201

  Last Sold Summary

  • 25% Below List Price
  • $632/SF
  • 25 Days On Market

  Last Sold Price $1,900,000

  Last Listing Agent Leslie Chesloff William Pitt
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  /2

  $189,900

  • 3 Beds
  • 2 Baths

  395 Cheshire Rd Unit 102, Pittsfield, MA 01201

  Check out this adorable 3 bed/2 bath double wide manufactured home with a welcoming front porch situated on the Ashuwillticook Rail Trail. Allendale Pines North is a brand new development with 22 homes slated for completion by the end of 2026. Be one of the first owners in this gorgeous new community.

  Val Whaling

  395 Cheshire Rd Unit 102, Pittsfield, MA 01201
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  /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 $448,082

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

  17 Kittredge Rd, Pittsfield, MA 01201
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  /45

  Est $285,980 Not Listed For Sale

  27 Westover St, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 1,273 Sq Ft
  • Built 1925

  27 Westover St, Pittsfield, MA 01201

  Last Sold Summary

  • 22% Above List Price
  • $185/SF
  • 3 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Jessica Rizzo LAMACCHIA REALTY, INC
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  /32

  $289,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,084 Sq Ft

  11 Crane Ave, Pittsfield, MA 01201

  Berkshire beauty near lakes. Live, Love, Play in this 2013 renovated ranch with many improvements making it a modern pleasure to enjoy. Roof, updated kitchen with granite countertops, stainless appliances, breakfast bar seating to converse with the cook. Shaker style cherry cabinets gleem while accomodating an abundance of neat and tidy storage. Back door leads to the rear deck and oversized back

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  11 Crane Ave, Pittsfield, MA 01201
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  /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 $378,419

  Last Listing Agent Chris LaPatin LAMACCHIA REALTY, INC

  36 Chickering St, Pittsfield, MA 01201
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  /16

  Est $230,543 Not Listed For Sale

  15 Francis Ave, Pittsfield, MA 01201

  • 5 Beds
  • 2 Baths
  • 2,320 Sq Ft
  • Built 1880

  15 Francis Ave, Pittsfield, MA 01201

  Last Sold Summary

  • 11% Above List Price
  • $89/SF
  • 324 Days On Market

  Last Sold Price $207,000

  Last Listing Agent Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
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  /14

  $1,399,000

  • 16 Beds
  • 16 Baths
  • 8,608 Sq Ft

  14 Highland Ave, Pittsfield, MA 01201

  Excellent 8-Unit Investment Opportunity-5 minute walk to the Lake!Clean, well-maintained multifamily property featuring 8 total units with separate utilities. Each unit includes central A/C. Property offers private, dedicated parking for tenants. Prime location--just minutes from major hospitals, large employers, shopping, and public transit. High-demand rental area with strong occupancy history.

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  14 Highland Ave, Pittsfield, MA 01201
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  /37

  $500,000 Sold Aug 06, 2025

  92 Leroi Dr, Pittsfield, MA 01201

  • 4 Beds
  • 2.5 Baths
  • 2,102 Sq Ft
  • Built 1967

  Last Sold Summary

  • 5% Below List Price
  • $238/SF
  • 34 Days On Market

  Current Estimated Value $503,715

  Last Listing Agent Andrew Manns LAMACCHIA REALTY, INC

  92 Leroi Dr, Pittsfield, MA 01201
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  /31

  Est $260,099 Not Listed For Sale

  716 Dalton Division Rd, Pittsfield, MA 01201

  • 2 Beds
  • 1 Bath
  • 1,049 Sq Ft
  • Built 1940

  716 Dalton Division Rd, Pittsfield, MA 01201

  Last Sold Summary

  • 15% Above List Price
  • $215/SF
  • 5 Days On Market

  Last Sold Price $226,000

  Last Listing Agent Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD
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  /42

  $299,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,024 Sq Ft

  71 Weller Ave, Pittsfield, MA 01201

  This spacious 3-4 bedroom, 3 bath home sits on a rare double lot and offers space, comfort and views. The big kitchen features an eye-catching island and granite countertops, perfect for everyday living and entertaining. A huge dining room with lots of natural light provides an ideal setting for hosting. Hardwood floors run throughout the entire home and a powder room is ideally located on the

  Andreea Duta BISHOP WEST REAL ESTATE

  71 Weller Ave, Pittsfield, MA 01201
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  /22

  $329,850 Sold Oct 01, 2025

  104 Quirico Dr, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 1,274 Sq Ft
  • Built 1963

  Last Sold Summary

  • $259/SF
  • 8 Days On Market

  Current Estimated Value $331,448

  Last Listing Agent Mark Harris SIGNATURE ASSOCIATES

  104 Quirico Dr, Pittsfield, MA 01201
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  /6

  Est $290,519 Not Listed For Sale

  31 Bossidy Dr, Pittsfield, MA 01201

  • 4 Beds
  • 2 Baths
  • 1,410 Sq Ft
  • Built 1972

  31 Bossidy Dr, Pittsfield, MA 01201

  Last Sold Summary

  • 8% Above List Price
  • $191/SF
  • 21 Days On Market

  Last Sold Price $269,900

  Last Listing Agent Jason Saphire www.HomeZu.com
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  /3

  $419,000

  • 7 Beds
  • 4.5 Baths
  • 4,682 Sq Ft

  312 South St, Pittsfield, MA 01201

  Four-family investment opportunity that checks all the boxes! Great location. Fully rented. Turnkey. Robust net operating income. This well-maintained home, comprising three 2-bedroom units and one 1-bedroom unit all with separate utilities, is an instant profit generator and offers real value in today's market.

  Derek Greene The Greene Realty Group

  312 South St, Pittsfield, MA 01201

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