Pittsfield, MA Homes for Sale under $400,000

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  /38

  $389,500

  $40K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,998 Sq Ft

  191 Fort Hill Ave, Pittsfield, MA 01201

  A rare opportunity to own 5.2 acres in Pittsfield for under $400,000! Set in the scenic countryside of West Pittsfield, this spacious 1820s farmhouse offers nearly 2,000 sq. ft. of living space, historic character, and room to make it your own. Inside, you'll find hardwood floors, a fireplace, beautiful central staircase, oversized bedrooms, enclosed porch, and walk-up attic. Updates include a

  THE KAHN TEAM BISHOP WEST REAL ESTATE

  191 Fort Hill Ave, Pittsfield, MA 01201
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  /32

  $295,000

  • 3 Beds
  • 1 Bath
  • 1,342 Sq Ft

  17 Howe Rd, Pittsfield, MA 01201

  Welcome to this charming, updated ranch tucked into a quiet neighborhood and conveniently located near shopping and restaurants. Enjoy the ease of single-level living with thoughtful updates throughout. Recent improvements include an updated bathroom, new driveway (2026), siding and Trex deck (2025), and furnace (2018), with the roof replaced in 2011. Move right in and enjoy a comfortable home

  Amanda Kmetz ROBERTS & ASSOC. REALTY, INC

  17 Howe Rd, Pittsfield, MA 01201
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  /8

  $380,000

  • Land
  • 15 Acres
  • $25,333 per Acre

  365 Churchill St, Pittsfield, MA 01201

  Discover the ideal setting for your next home or retreat on this 15-acre parcel in West Pittsfield. Thoughtfully prepared, the property already features installed electricity, along with a newly constructed driveway and building pad. Enjoy a perfect blend of open and wooded land, including 5+ acres of fields, 10 acres of forest, and approximately 700 feet of road frontage. With city water,

  Sarah Carr Key Realty

  365 Churchill St, Pittsfield, MA 01201
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  /12

  $159,000

  • Land
  • 1.3 Acres
  • $122,308 per Acre

  636 Hancock Rd, Pittsfield, MA 01201

  An excellent opportunity to build your dream home on over an acre of land with many of the major improvements already in place. This developed parcel is ready for its next owner, featuring power with meter and panel, city water connected with an on-site shutoff, and operable internet service. A milled blacktop driveway provides convenient access, and city-approved septic designs have already been

  Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

  636 Hancock Rd, Pittsfield, MA 01201
• 

  

  

  /22

  $199,900

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

  395 Cheshire Rd Unit 104, 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. This home is set to drop end of August 2026.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

  Jason Nocher NOCHER REALTY

  395 Cheshire Rd Unit 104, Pittsfield, MA 01201
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  /26

  $189,000

  $40K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 2,234 Sq Ft

  969 Dalton Ave, Pittsfield, MA 01201

  Exceptional Investment Opportunity: Versatility & Prime LocationDiscover a property that offers unparalleled flexibility in one of Pittsfield's most active commercial corridors. Situated on a sprawling 0.92-acre lot directly across from Berkshire Crossing, this unique property presents a rare ''blank canvas'' for homeowners and investors alike. Currently configured for mixed-use with a

  Timothy Johnson NOCHER REALTY

  969 Dalton Ave, Pittsfield, MA 01201
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  /27

  $289,000

  $20K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,032 Sq Ft

  34 Hungerford St, Pittsfield, MA 01201

  Welcome to this beautifully built new construction home offering the perfect blend of style, efficiency, and comfort. Featuring 2 spacious bedrooms and 1.5 bathrooms, this thoughtfully designed home boasts an open-concept layout with bright natural light, modern finishes, and quality craftsmanship throughout.The main living area flows seamlessly into the kitchen and dining space, creating

  Ahliya Phillips KELLER WILLIAMS REALTY

  34 Hungerford St, Pittsfield, MA 01201
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  /29

  $109,900

  • 3 Beds
  • 2 Baths
  • 1,168 Sq Ft

  167 Daniels Ave, Pittsfield, MA 01201

  Maureen DeRito Landmark REO Inc.

  167 Daniels Ave, Pittsfield, MA 01201
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  /30

  $359,900

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  180 Doreen St, Pittsfield, MA 01201

  Well maintained 4 bedroom, 2 full bath cape set on a level quarter acre with mature landscaping! The first floor offers comfortable living space along with a full bathroom. Upstairs you will find additional bedrooms and a second full bath, so there is a full bathroom on each level. The home's electrical was upgraded in 2025. Other major updates include a brand new garage built in 2025 and a roof

  Kyle Crocker eXp REALTY

  180 Doreen St, Pittsfield, MA 01201
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  /32

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  296 Hancock Rd, Pittsfield, MA 01201

  Welcome to this bright and inviting 3-bedroom, 1-bath ranch, ideally located just moments from beautiful Pontoosuc Lake on a spacious double lot. This home features a generous living room with oak hardwood floors, a formal dining room, and an updated kitchen with newer countertops. Additional highlights include a spacious basement with abundant storage, an oversized one-car garage, and an

  Jose Larios Lamacchia Realty, Inc.

  296 Hancock Rd, Pittsfield, MA 01201
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  /37

  $349,900

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  30 Joan Dr, Pittsfield, MA 01201

  Well-located home nestled in a desirable neighborhood with convenient access to local amenities, schools, and outdoor recreation. This inviting property offers a comfortable layout designed for everyday living and entertaining, featuring bright, sun-filled spaces and a warm, welcoming atmosphere throughout.The home provides a functional flow with generously sized living areas, a thoughtfully

  John Ciepiela BISHOP WEST REAL ESTATE

  30 Joan Dr, Pittsfield, MA 01201
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  /31

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft

  225 Brown St, Pittsfield, MA 01201

  Raised ranch with two-car garage, located on a double lot with almost half an acre of land. The main level features 3 bedrooms, full bathroom, living room and kitchen with dining area, with slider opening to deck which was recently painted. The finished lower level offers family room with sliders to the backyard. In addition to the hot water baseboard, this family room also features a pellet

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  225 Brown St, Pittsfield, MA 01201
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  /38

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft

  100 Essex St, Pittsfield, MA 01201

  Recently renovated colonial home with detached garage, located on a corner lot in a desirable Pittsfield location! This property features a lovely front porch as well as a side porch and great yard! There are 3 bedrooms, however, the home could be used as a 4-bedroom. You will love the two updated full bathrooms, one on each floor! Other improvements include a new roof, newer vinyl replacement

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  100 Essex St, Pittsfield, MA 01201
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  /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
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  /22

  $239,000

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  14 Clifford St Unit A5, Pittsfield, MA 01201

  Affordable living awaits in this freshly painted, charming condo in a small eight-unit association. The $200 monthly HOA fee includes road maintenance, snow removal, master insurance, and trash. Two parking spaces are located in front. The first floor features a spacious living room, generously sized kitchen with a dining area, convenient half bath, and direct access to a private rear deck.

  Andreea Duta BISHOP WEST REAL ESTATE

  14 Clifford St Unit A5, Pittsfield, MA 01201
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  /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
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  /40

  $209,900

  $5K PRICE DROP

  • 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
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  /11

  $264,900

  • 4 Beds
  • 2.5 Baths
  • 2,132 Sq Ft

  50 John St, Pittsfield, MA 01201

  Side-by-side two-family home renovated in the last few years! Improvements include roof, windows, flooring, painting, and more! The home offers an enclosed front porch to access both units, and a side porch for each apartment independently. Each unit features living room, dining room, kitchen, 2 bedrooms and 1 bath. The apartments have large enclosed back porches upstairs overlooking the yard.

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  50 John St, Pittsfield, MA 01201
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  /24

  $319,900

  • 3 Beds
  • 2 Baths
  • 1,259 Sq Ft

  79 Clark Rd, Pittsfield, MA 01201

  Welcome home to this charming ranch offering effortless single-level living in a quiet, private, yet convenient neighborhood! Lovingly built, maintained, and cherished by the same family for decades, this home offers the perfect blend of comfort, flexibility, and functionality. The living room has a beautiful bay window, 3 bedrooms with abundant closet space and a full bath. The kitchen opens to

  Nancy Bush Brooks SIGNATURE ASSOCIATES

  79 Clark Rd, Pittsfield, MA 01201
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  /14

  $285,000

  • 5 Beds
  • 3 Baths
  • 2,638 Sq Ft

  61 Calumet St, Pittsfield, MA 01201

  Opportunity awaits! This three-unit property is situated on a large lot and offers excellent potential for an owner-occupant or investor. Two of the three units are currently rented, providing immediate rental income, while the additional unit offers flexibility for occupancy or future rental. A detached two-car garage provides valuable parking and storage space, and the generous yard adds to the

  Katie Soules WILLIAM RAVEIS - BERKSHIRE

  61 Calumet St, Pittsfield, MA 01201
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  /33

  $379,900

  $342K PRICE INCREASE

  • 3 Beds
  • 1.5 Baths
  • 1,782 Sq Ft

  84 Windsor Ave, Pittsfield, MA 01201

  Welcome home to this inviting 3-bedroom, 1.5-bath home offering comfortable living spaces and plenty of charm. Wood floors flow throughout the main living areas, while the open dining and kitchen layout creates a warm, functional space for everyday living. A convenient first-floor half bath adds to the home's practicality. The living room features a cozy fireplace and opens to a delightful

  Robin Moore 413 REAL ESTATE

  84 Windsor Ave, Pittsfield, MA 01201
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  /20

  $375,000

  • 7 Beds
  • 3.5 Baths
  • 3,672 Sq Ft

  98 Lincoln St, Pittsfield, MA 01201

  Turnkey 3-unit multifamily investment in Pittsfield, just minutes from downtown. Fully occupied, generating $4,173/month ($50,076/year) in gross rent from all-current tenants. Unit mix: 98A (1BR/1BA) at $1,199/mo, 98B (2BR/1BA) at $1,324/mo, and 100 (3BR/2BA) at $1,650/mo. All three units have gas heat and hot water; owner covers snow removal, landscaping, and water & sewer. 2025 operating

  Jason Saphire www.HomeZu.com

  98 Lincoln St, Pittsfield, MA 01201
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  /40

  $314,900

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  84 Williams St, Pittsfield, MA 01201

  Nestled in Pittsfield's desirable Southeast neighborhood, this charming Colonial offers the perfect blend of character, comfort, and modern updates. Featuring 3 bedrooms and 1.5 bathrooms, the home boasts a modern kitchen complete with a pantry. Hardwood floors flow throughout much of the home, and a cozy wood-burning fireplace. The bright four-season sun porch provides the perfect spot to relax

  Jessica Rizzo Lamacchia Realty, Inc. - Dalton

  84 Williams St, Pittsfield, MA 01201
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  /2

  $299,900

  • Land
  • 6 Acres
  • $49,983 per Acre

  0 West St, Pittsfield, MA 01201

  This land is ideally located near downtown. 6 acres in a R6 zone, this has been approved for subdivision in the past. Comes with complete engineering including maps, topo's, traffic study, and much more. Beautiful views of Bousquet, bus line, all public utilities available. A RARE development opportunity to change the housing market in Pittsfield.

  Steve Ray 413 REAL ESTATE

  0 West St, Pittsfield, MA 01201
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  /2

  $155,000

  • Land
  • 5 Acres
  • $31,000 per Acre

  365 Churchill St, Pittsfield, MA 01201

  Seller is offering a 5-acre lot for separate sale from the 15-acre property. The 5-acre parcel does not include the installed electricity, driveway, or building pad, which are located on the 10-acre parcel.Also available with 15 acres MLS#248259

  Sally Carr KEY REALTY

  365 Churchill St, Pittsfield, MA 01201
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  /17

  $158,900

  • 2 Beds
  • 1 Bath
  • 1,158 Sq Ft

  186 Burbank St, Pittsfield, MA 01201

  Welcome to 186 Burbank Street! This charming colonial-style home offers two bedrooms, one full bathroom, and 1,158 square feet of living space. Situated on a level corner lot in an established residential neighborhood, the home features a functional layout with plenty of potential. The main level includes a spacious kitchen with ample cabinet and counter space, a formal dining room, comfortable

  Zachary DeCaro Property Works New England

  186 Burbank St, Pittsfield, MA 01201
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  /25

  $159,900

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  120 Danforth Ave, Pittsfield, MA 01201

  Looking for an affordable home? This 2 bedroom home is move in ready. Freshly painted, new flooring, in the kitchen and bath. It has an eat in kitchen with laundry off the kitchen. Dining room and livingroom complete the first floor. 2 bedrooms with newly installed carpet on the 2cnd floor. There is an extra room upstairs that can be used as a play room, office or extra storage.

  Janet Benoit MOCKINGBIRD REAL ESTATE

  120 Danforth Ave, Pittsfield, MA 01201
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  /7

  $219,900

  $30K PRICE DROP

  • 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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  /20

  $189,900

  New Construction

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

  395 Cheshire Rd Unit 113, 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 convenience

  Jason Nocher NOCHER REALTY

  395 Cheshire Rd Unit 113, Pittsfield, MA 01201
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  /21

  $189,000

  $10K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,480 Sq Ft

  57 Adam St, Pittsfield, MA 01201

  Offering an affordable path to homeownership, this property is ideal for buyers ready to trade renting for a place of their own or investors looking to expand their rental portfolio. The first floor includes an eat-in kitchen, first-floor laundry, and a flexible room for additional living space. Bring your ideas and make it your own over time. A covered back patio extends your living space

  Leanne Sedlak REAL BROKER

  57 Adam St, Pittsfield, MA 01201
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  /15

  $295,000

  $40K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,452 Sq Ft

  144 Elberon Ave, Pittsfield, MA 01201

  Welcome to 144 Elberon Ave. This home is close to Golf, Shopping, Dining, Parks, Down town and so much more yet its on a lovely side street. Three bedroom Garrison Colonial offers formal dining room, formal living room with fire place and nice den. Under the carpet you will find blond oak floors. The back yard offers nice views, a patio and hot tub. The home was converted to gas approximately 5

  Sherry Street REALTY STREET, LLC

  144 Elberon Ave, Pittsfield, MA 01201
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  /28

  $234,999

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  98 Bryan St, Pittsfield, MA 01201

  Welcome to this move-in ready Colonial that blends timeless charm with the beauty of Berkshire living. Enjoy seasonal mountain views and convenient access to nearby hiking trails right from the street, with golf courses, lakes, parks, and outdoor recreation just minutes away. Ideally located near downtown Pittsfield, you'll have easy access to restaurants, shopping, entertainment, and cultural

  Harmony Edwards KELLER WILLIAMS REALTY

  98 Bryan St, Pittsfield, MA 01201
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  /27

  $179,900

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 540 Sq Ft

  21 Woodleigh Rd, Pittsfield, MA 01201

  Robin Moore 413 REAL ESTATE

  21 Woodleigh Rd, Pittsfield, MA 01201
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  /50

  $224,900

  • 6 Beds
  • 4 Baths
  • 3,530 Sq Ft

  310 Wahconah St, Pittsfield, MA 01201

  Fantastic investment opportunity on Wahconah St! This four-family property offers immediate income potential with two front, two bedroom units ready to rent while you complete the two rear, one bedroom units and build additional value. The front units feature attractive hardwood floors, tile in the kitchens and bathrooms, and a distinctive interior layout that adds charm and character. Outside,

  Cory Evangelisto NOCHER REALTY

  310 Wahconah St, Pittsfield, MA 01201
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  /38

  $399,000

  $20K PRICE DROP

  • 8 Beds
  • 4 Baths
  • 2,688 Sq Ft

  53 Orchard St, Pittsfield, MA 01201

  Presenting a distinguished multi-family property located at 53 Orchard St, Pittsfield, MA.. This expansive 4 unit spans 2688 square feet of living area, offering a rare opportunity for sophisticated urban living or a strategic investment. This property includes six generously proportioned bedrooms, providing ample private accommodations across its two stories. The property's substantial lot size

  David Houser Houser Metro Realty

  53 Orchard St, Pittsfield, MA 01201
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  /38

  $299,900

  • 5 Beds
  • 2 Baths
  • 2,690 Sq Ft

  63 Glenwood Ave, Pittsfield, MA 01201

  Charming 2-family flat offering a great opportunity for owner-occupants or investors alike! This well-maintained property features beautiful wood floors, inviting front porches, and private back decks perfect for relaxing or entertaining. Both units have separate utilities for added convenience and efficiency. The second-floor apartment includes a finished attic area providing extra living space.

  Robin Moore 413 REAL ESTATE

  63 Glenwood Ave, Pittsfield, MA 01201
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  /34

  $265,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  1228 East St, Pittsfield, MA 01201

  Welcome to 1228 East St. A longtime family home filled with warmth, character and opportunity. Beautiful hardwood floors throughout much of the home. Updates include electric panel, blown in insulation, a new oil tank 2018 and new oil burner 2022. The spacious second floor kitchen area offers potential to create a two-family flat subject to city approval. Close to shopping, parks, recreation and

  Anthony Riello Lamacchia Realty, Inc. - Dalton

  1228 East St, Pittsfield, MA 01201
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  /25

  $354,900

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft

  62 Easton Ave, Pittsfield, MA 01201

  Welcome home to this beautifully updated 3-bedroom, 1-bath home in a great neighborhood close to the local school! The first-floor bedroom and bathroom offer convenient one-level living, while the recently renovated kitchen with marble backsplash, quartz counter tops and shaker cabinets provide a fresh, modern feel. Numerous updates throughout make this home move-in ready. Enjoy the spacious

  Andrew Manns Lamacchia Realty, Inc. - Dalton

  62 Easton Ave, Pittsfield, MA 01201
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  /34

  $249,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft

  34 Baldwin Ave, Pittsfield, MA 01201

  Welcome to The Orchards, one of Southeast Pittsfield's most desirable neighborhoods. Sited on a beautiful lot, this 3 bedroom, 1 bath ranch offers comfortable one-level living at an outstanding price, allowing you to make updates and transform this home to suit your needs. Large eat in kitchen and spacious family room make it easy to host family and friends. Whether you're starting your next

  Victoria Standring Lamacchia Realty, Inc. - Dalton

  34 Baldwin Ave, Pittsfield, MA 01201
• 

  

  /34

  $275,000

  • 5 Beds
  • 2 Baths
  • 2,158 Sq Ft

  34 Daniels Ave, Pittsfield, MA 01201

  Welcome to 34 Daniels Avenue, part of the Westside Legends Attainable Housing Program. This updated Pittsfield home offers a comfortable layout with recent improvements throughout, including new flooring, new appliances, and refreshed bathrooms. The interior feels clean, bright, and move-in ready, while still offering a practical and manageable footprint for everyday living. Conveniently located

  Samantha Homeyer BIRCH PROPERTIES

  34 Daniels Ave, Pittsfield, MA 01201

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