Pittsfield, MA Homes for Sale under $500,000

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  /33

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,961 Sq Ft

  5 Putnam Ave, Pittsfield, MA 01201

  Southeast brick cape ready for summer fun! This 3 bed 2 bath cape is filled with warmth, character, and inviting spaces ready for memories all season long. Bright open kitchen, which flows to the dining area and family room with vaulted ceilings and doors to the deck. Around the corner a 2nd family room, game room or whatever you decide with wood burning fireplace. 1st floor also offers spacious

  

  Laura Arseneau

  PAULA MCLEAN REALTORS INC.

  5 Putnam Ave, Pittsfield, MA 01201
• Explore Pittsfield

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  /4

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft

  Lot 4 Tanner St, Pittsfield, MA 01201

  To Be Built, energy-efficient, low-maintenance 1,340 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home features an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. A split-entry design leads to a one-car garage underneath, offering convenience and additional storage. The primary suite includes a private full bath,

  

  Syrah Bradley

  BISHOP WEST REAL ESTATE

  Lot 4 Tanner St, Pittsfield, MA 01201
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  /4

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft

  Lot 5 Tanner St, Pittsfield, MA 01201

  To Be Built, energy-efficient, low-maintenance 1,340 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home features an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. A split-entry design leads to a one-car garage underneath, offering convenience and additional storage. The primary suite includes a private full bath,

  

  Syrah Bradley

  BISHOP WEST REAL ESTATE

  Lot 5 Tanner St, Pittsfield, MA 01201
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  /4

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft

  Lot 6 Tanner St, Pittsfield, MA 01201

  To Be Built, energy-efficient, low-maintenance 1,340 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home features an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. A split-entry design leads to a one-car garage underneath, offering convenience and additional storage. The primary suite includes a private full bath,

  

  Syrah Bradley

  BISHOP WEST REAL ESTATE

  Lot 6 Tanner St, Pittsfield, MA 01201
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  /3

  $389,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,375 Sq Ft

  0 Broadview Terrace, Pittsfield, MA 01201

  To Be Built, energy-efficient, low-maintenance 1,375 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home offers true single-level living with an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. The primary suite includes a private full bath, while two additional bedrooms offer flexibility for guests or a home office.

  

  Syrah Bradley

  BISHOP WEST REAL ESTATE

  0 Broadview Terrace, Pittsfield, MA 01201
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  /42

  $339,900

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,793 Sq Ft

  112 Plunkett St, Pittsfield, MA 01201

  Welcome to this impeccably maintained 4-BR, 2 bath residence offering comfort, style, & exceptional outdoor living. The updated kitchen features all new appliances, while the spacious layout provides plenty of room for family, guests, or a home office. Potential 1st floor BR! Step outside & discover your own private backyard retreat. Relax under the covered porch, entertain on the dining patio,

  Mary Jane Dunlop BISHOP WEST REAL ESTATE

  112 Plunkett St, Pittsfield, MA 01201
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  /25

  $255,000

  • 2 Beds
  • 1 Bath
  • 1,227 Sq Ft

  58 Churchill Crest, Pittsfield, MA 01201

  2 bedroom end unit condo offering the rare ease of true one level living, tucked in Churchill Crest's most private and peaceful building. This special home feels like a quiet Berkshire sanctuary, with a thoughtful layout that flows comfortably and welcomes you the moment you arrive. It's ready for your vision, character allows you to shape the space to your own style. Outside, enjoy a sparkling

  Keyla Girard Lamacchia Realty, Inc. - Dalton

  58 Churchill Crest, Pittsfield, MA 01201
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  /26

  $220,000

  • 7 Beds
  • 2.5 Baths
  • 3,216 Sq Ft

  27 Daniels Ave, Pittsfield, MA 01201

  Bring your vision and creativity to this spacious side-by-side duplex that's been stripped down and prepped for its next chapter. Much of the heavy lifting has already been completed, including extensive demolition work and rough electrical installation. The exterior has also received a fresh coat of paint, providing a head start on your renovation plans. Originally intended to be converted into

  Michele Purcell Lamacchia Realty, Inc. - Dalton

  27 Daniels Ave, Pittsfield, MA 01201
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  /42

  $269,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft

  3 Clarendon St, Pittsfield, MA 01201

  Set on an oversized corner lot at the end of a quiet dead-end street, this bright renovated 3-bedroom, 2-bath home offers an impressive amount of outdoor space in a neighborhood setting. The expansive yard is the standout feature, with established gardens, mature trees, a firepit area, open lawn space, & a fenced section for pets. Inside, the home has been thoughtfully updated throughout. The

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  3 Clarendon St, Pittsfield, MA 01201
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  /14

  $259,900

  • 5 Beds
  • 2 Baths
  • 2,520 Sq Ft

  178 Appleton Ave, Pittsfield, MA 01201

  Move right into the vacant unit and start generating income from the other. The property includes a small, easy-to-maintain yard, perfect for enjoying outdoor space without extensive upkeep. While there is no off-street parking, the property's functional layout and income-producing potential make it an excellent value. Whether you're looking to owner-occupy or expand your investment portfolio,

  Robin Moore 413 REAL ESTATE

  178 Appleton Ave, Pittsfield, MA 01201
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  /30

  $269,900

  $30K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,362 Sq Ft

  1952 East St, Pittsfield, MA 01201

  Worth a second look! With a newly reduced price and some recent seller improvements, this 3-bedroom 1- bath brick Cape offers unmatched value in today's market. The sellers have listened to feedback, completed repairs, and beautifully optimized the space. Bring your buyers back through before it's gone!Perfect for first-time buyers or downsizers. Features functional layout, warm hardwood

  Melinda Boos KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  1952 East St, Pittsfield, MA 01201
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  /43

  $469,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft

  16 Trova Terrace, Pittsfield, MA 01201

  Immaculate, adorable, expansive, well maintained 2500 sq ft ranch. 4 bedrooms 3 bathrooms, open living room & dining area with fireplace. Bright eat in kitchen, a sunny 3 season porch with a newer deck. This home sits on a 1/2-acre lot in a quiet tucked away neighborhood. There's a full walkout lower level with family room, fireplace, bar, full bathroom & dining area which leads to a back patio

  Matt Jarck WILLIAM PITT SOTHEBY'S - LENOX

  16 Trova Terrace, Pittsfield, MA 01201
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  /43

  $414,900

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft

  19 Roselyn Dr, Pittsfield, MA 01201

  This charming 3-bedroom home is ready to move in! Great west Pittsfield neighborhood. Just 5 minutes from downtown, less than 20 to Tanglewood, a half hour drive to Williams College and the Clark Art Institute. Wood burning fireplace, lots of natural light, heated sun porch, and a beautiful backyard with a large deck, berry bushes, and fruit trees. The first floor features the kitchen with

  Allison Pacelli PACELLI ZEPKA

  19 Roselyn Dr, Pittsfield, MA 01201
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  /7

  $380,000

  $55K PRICE DROP

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

  0 Churchill St Unit 248259, Pittsfield, MA 01201

  Price reduction. Motivated seller.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

  Sally Carr KEY REALTY

  0 Churchill St Unit 248259, Pittsfield, MA 01201
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  /29

  $289,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,627 Sq Ft

  162 W Housatonic St, Pittsfield, MA 01201

  Enjoy this charming 4-bedroom, 2-bathroom home offering a spacious and functional layout, tasteful updates, and excellent convenience. The property features an updated heating system, efficient natural gas utilities, a large open kitchen with new appliances, and updated flooring. Both bathrooms have been recently renovated with stylish new finishes and tilework. Enjoy the flexibility of a

  Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

  162 W Housatonic St, Pittsfield, MA 01201
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  /24

  $345,000

  $40K PRICE DROP

  • 6 Beds
  • 6 Baths
  • 2,260 Sq Ft

  37 Melville St, Pittsfield, MA 01201

  Six unit multi-family investment property located in the heart of downtown Pittsfield. Located footsteps from shopping, restaurants, an more!. Includes six studio apartments, vinyl siding, and separate electricity for each unit.

  Cory Evangelisto NOCHER REALTY

  37 Melville St, Pittsfield, MA 01201
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  /20

  $209,000

  • 4 Beds
  • 1.5 Baths
  • 2,059 Sq Ft

  232 First St, Pittsfield, MA 01201

  Located on the edge of Pittsfield's Downtown Creative District, this versatile colonial has served as professional office space for 20+ years and offers endless possibilities. Features include 6 private offices, a reception/waiting area, half bath, bonus room, handicap-accessible ramp, off-street parking, and a detached 4-bay garage with income potential. Ideal for medical, professional,

  Anthony Riello Lamacchia Realty, Inc. - Dalton

  232 First St, Pittsfield, MA 01201
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  /28

  $298,000

  $14K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 5,392 Sq Ft

  50 W Housatonic St, Pittsfield, MA 01201

  This well-maintained multi-unit property presents an exceptional opportunity in the heart of Pittsfield's thriving Downtown Cultural District. Offering spacious units with strong rental appeal, the property combines classic character with important updates including newer siding, a high-efficiency natural gas heating system and a new roof in 2021. A unique feature of the property is the versatile

  Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

  50 W Housatonic St, Pittsfield, MA 01201
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  /41

  $289,900

  Pre-Foreclosure

  • 4 Beds
  • 1.5 Baths
  • 1,572 Sq Ft

  246 Dalton Ave, Pittsfield, MA 01201

  Welcome to 246 Dalton Ave, a charming colonial-style home nestled in the heart of Pittsfield, MA. This delightful residence features four spacious bedrooms and one and a half baths, perfect for families or those seeking extra space. The home does offer potential for a 1st floor bedroom as well. The classic architecture is complemented by modern updates, providing a cozy yet stylish living

  Doug Collins Lamacchia Realty, Inc. - Dalton

  246 Dalton Ave, Pittsfield, MA 01201
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  /3

  $349,900

  • 3 Beds
  • 1.5 Baths
  • 1,246 Sq Ft

  75 3rd St, Pittsfield, MA 01201

  Contemporary home boasting with charm and character. 3 bedrooms, and 1 1/2 baths Located close to the downtown area.

  Janet Benoit MOCKINGBIRD REAL ESTATE

  75 3rd St, Pittsfield, MA 01201
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  /11

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  20 Curtis Terrace, Pittsfield, MA 01201

  Welcome to this spacious 3-bedroom, 2-bath home offering 1,920 square feet of living space in Pittsfield's desirable Morningside neighborhood. This home blends classic character with several major updates already completed, including a newer roof (2025), replacement windows, oil tank (2024), boiler (2019), and sewer line (2019). The flexible floor plan provides plenty of room for everyday living,

  ShaDina Johnson Berkshire Hathaway HomeServices Realty Professionals

  20 Curtis Terrace, Pittsfield, MA 01201
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  /35

  $249,900

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 1,060 Sq Ft

  64 Churchill Crest, Pittsfield, MA 01201

  Uniquely and tastefully renovated one-bedroom end unit condo with open living concept, and fully furnished! (some artwork excluded) Great room with fireplace, recessed lighting, ceiling fans, stainless appliances, microwave with expandable exhaust vent, modern bathroom with double shower, swanstone vanity sink, built in cabinet.... Simply move in and live! New central air conditioner in 2012 and

  Susan Calkins STONE HOUSE PROPERTIES, LLC

  64 Churchill Crest, Pittsfield, MA 01201
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  /43

  $295,000

  Open Sat 12PM - 1:30PM

  • 2 Beds
  • 1 Bath
  • 1,032 Sq Ft

  67 Partridge Rd, Pittsfield, MA 01201

  Meticulously maintained and move in ready, this charming 2/3 bedroom, 1 bath ranch offers comfortable living with thoughtful updates throughout. The bright main level is complemented by finished lower level space featuring a versatile office or potential guest bedroom and living room, providing extra flexibility. Major updates include a roof and windows less than five years old. Step outside to a

  Katie Soules WILLIAM RAVEIS - BERKSHIRE

  67 Partridge Rd, Pittsfield, MA 01201
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  /40

  $284,900

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,501 Sq Ft

  96 Boylston St, Pittsfield, MA 01201

  Back on the market, and someone else's loss is about to be your gain. Some homes just feel right the moment you arrive. Sitting at the end of a dead-end street, 96 Boylston offers the kind of quiet and privacy that's hard to find this close to downtown Pittsfield. No through traffic, no neighbors driving past, just a peaceful street that's yours to enjoy. Step inside and you'll find a clean,

  Kyle Crocker eXp REALTY

  96 Boylston St, Pittsfield, MA 01201
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  /46

  $379,900

  • 4 Beds
  • 1.5 Baths
  • 1,657 Sq Ft

  24 Marlboro Dr, Pittsfield, MA 01201

  Move right into this beautifully updated Colonial on a quiet, tree-lined street! Thoughtfully renovated and lovingly maintained, this charming home is truly turnkey. Enjoy peace of mind with a new roof and new sewer line, along with a stunning new kitchen featuring stone countertops, upgraded stainless steel appliances, soft-close cabinets and drawers, and abundant workspace. The inviting floor

  Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  24 Marlboro Dr, Pittsfield, MA 01201
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  /2

  $211,000

  • 3 Beds
  • 2 Baths
  • 1,923 Sq Ft

  47 Lake St, Pittsfield, MA 01201

  Duplex Investment Property!

  Lisa Kelley MACCARO REAL ESTATE

  47 Lake St, Pittsfield, MA 01201
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  /18

  $449,900

  • 4 Beds
  • 4 Baths
  • 2,790 Sq Ft

  21 Linden St, Pittsfield, MA 01201

  Incredible Multi-Unit Investment Opportunity in Downtown Pittsfield! Located just steps from the Barrington Stage Company theater in the heart of the cultural district, this dynamic property includes 3 apartments, making it a true income-generating powerhouse. This is a rare opportunity for both the savvy investor and the live-in owner looking to offset housing expenses. The entire property has

  Michael Castellano GILCREST PROPERTIES

  21 Linden St, Pittsfield, MA 01201
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  /13

  $259,900

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,672 Sq Ft

  29 Westminster St, Pittsfield, MA 01201

  Income-producing two-family ranch with one vacant unit and one occupied unit, offering an excellent opportunity for both owner-occupants and investors looking to expand their portfolio. The occupied unit is supported by Section 8 assistance, providing reliable rental income. Each mirrored unit features 2 bedrooms and 1 full bathroom with functional, well-designed layouts. The vacant unit has been

  Matthew Keller KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  29 Westminster St, Pittsfield, MA 01201
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  /31

  $329,000

  • 4 Beds
  • 3 Baths
  • 1,575 Sq Ft

  28 Adelaide Ave, Pittsfield, MA 01201

  Welcome to this charming four-bedroom, three-bath home nestled in a desirable Southeast Pittsfield neighborhood. Lovingly maintained and well insulated through the years, this home offers a warm and inviting atmosphere with a wonderful blend of original character and everyday comfort.Inside, you'll find hardwood flooring, spacious bedrooms, two first-floor bedrooms and 2 full bathroom, and an

  Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

  28 Adelaide Ave, Pittsfield, MA 01201
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  /48

  $294,900

  • 3 Beds
  • 1 Bath
  • 1,282 Sq Ft

  61 Harding St, Pittsfield, MA 01201

  Charming, Move-In Ready Side Hall Colonial - A True ''Dollhouse!''Welcome home to this absolutely stunning, meticulously maintained side hall colonial nestled in a super quiet, peaceful neighborhood. Combining classic charm with a long list of modern, high-ticket upgrades, this home is the definition of a turnkey property and is ready for its next chapter. Step inside to find a warm and

  Stacy Chojnowski WILLIAM PITT SOTHEBY'S - LENOX

  61 Harding St, Pittsfield, MA 01201
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  /40

  $399,900

  • 4 Beds
  • 3 Baths
  • 2,170 Sq Ft

  118 Winesap Rd, Pittsfield, MA 01201

  Opportunity awaits in this spacious 4-bedroom, 3-bath Colonial located in the highly sought-after Orchard neighborhood. Offering generous room sizes throughout, this home features a welcoming family room with a fireplace and skylights that fill the space with natural light. The convenient first-floor laundry enhances everyday living. The partially finished basement provides additional flexible

  Robin Moore 413 REAL ESTATE

  118 Winesap Rd, Pittsfield, MA 01201
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  /38

  $290,000

  • 3 Beds
  • 1 Bath
  • 1,180 Sq Ft

  28 Hopewell Dr, Pittsfield, MA 01201

  Welcome home to this charming three-bedroom, one-bath ranch conveniently located in Pittsfield, just minutes from shopping, dining, and everyday amenities. This well-maintained home offers comfortable one-level living and features a bright sunroom that provides the perfect space to relax while overlooking the backyard. With efficiency in mind, the property includes solar panels and a pellet stove

  Jessica Rizzo Lamacchia Realty, Inc. - Dalton

  28 Hopewell Dr, Pittsfield, MA 01201
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  /52

  $349,900

  $30K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,661 Sq Ft

  249 Hancock Rd, Pittsfield, MA 01201

  Spacious and inviting 4-bedroom, 3-bath home offering comfort, efficiency, and great indoor-outdoor living. Beautiful wood floors run throughout the main living areas, adding warmth and character. The private primary suite features its own bath and sliding doors leading to a deck that overlooks a fully fenced backyard--perfect for relaxing or entertaining. Enjoy the added bonus of a covered patio

  Robin Moore 413 REAL ESTATE

  249 Hancock Rd, Pittsfield, MA 01201
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  /21

  $235,900

  • 2 Beds
  • 1.5 Baths
  • 1,008 Sq Ft

  48 Crystal St, Pittsfield, MA 01201

  Charming and full of potential, this inviting two-bedroom Cape is tucked away on a quiet dead-end street and ready for its next owner! A fieldstone walkway welcomes you and adds timeless curb appeal from the moment you arrive. Inside, you’ll find an enclosed front porch perfect for enjoying your morning coffee, an updated kitchen including refrigerator and stove, a convenient first-floor bedroom,

  Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals

  48 Crystal St, Pittsfield, MA 01201
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  /32

  $310,000

  Open Sat 10AM - 11:30AM

  • 3 Beds
  • 1 Bath
  • 1,275 Sq Ft

  16 Wealthy Ave, Pittsfield, MA 01201

  3 bedroom, 1 bath ranch in Pittsfield's desirable Orchards neighborhood! Featuring beautifully refinished hardwood floors, this home offers comfortable one level living with plenty of potential to make it your own. Enjoy morning coffee or unwind in the screened porch overlooking the backyard. Additional features include a one car garage, full basement offering ample storage or workshop space, and

  Katie Soules WILLIAM RAVEIS - BERKSHIRE

  16 Wealthy Ave, Pittsfield, MA 01201
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  /40

  $379,900

  $9K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft

  1121 North St, Pittsfield, MA 01201

  Motivated Seller! 1121 North St is a well-cared for home offering comfort, convenience with classic style and some modern updates. Fully fenced backyard. Perfect for pets, gardening, entertaining or relaxing in your own private retreat. Unwind in the bright sunroom with its own gas fireplace for chilly evenings and winter days. The oversized garage opens to a mudroom. Updated kitchen and a half

  Anthony Riello Lamacchia Realty, Inc. - Dalton

  1121 North St, 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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  /45

  $329,000

  • 6 Beds
  • 2 Baths
  • 2,592 Sq Ft

  78 Harvard St, Pittsfield, MA 01201

  Enjoy this move-in ready and meticulously maintained two-family home in the heart of Pittsfield. Featuring two spacious side-by-side units, this property offers an excellent opportunity for both owner-occupants and investors alike. Enjoy efficient natural gas heating systems, updated hot water heaters, and a beautifully rebuilt front porch that adds timeless curb appeal.Inside, you'll find

  Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

  78 Harvard St, Pittsfield, MA 01201
• 

  

  /31

  $275,000

  Open Sat 10:30AM - 12PM

  • 2 Beds
  • 1 Bath
  • 1,240 Sq Ft

  0 Pondview Dr Unit H2, Pittsfield, MA 01201

  OPEN HOUSE SAT 10:30-NOONWelcome to James Meadow! Tucked away in a peaceful, park-like setting, this beautifully refreshed end-unit offers the perfect blend of comfort and convenience.The bright main level features an open living and dining area with gleaming hardwood floors, fresh paint, and a cozy gas fireplace. The well appointed galley kitchen comes equipped with solid oak cabinetry

  Maureen Kirby NOCHER REALTY

  0 Pondview Dr Unit H2, Pittsfield, MA 01201
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  /27

  $319,000

  $20K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  33 Reuter Ave, Pittsfield, MA 01201

  Lovely southeast Colonial on a dead-end street. This spacious home has a beautiful new kitchen, living room, sunroom/office, hardwood floors throughout and plenty of living space. The 1st floor bedroom could be used as a in-law or primary suite, featuring family room, fireplace with wood stove insert, half bath and sliding doors for privacy from the rest of the house. This home also has Upstairs

  Toni Marie Gage SIGNATURE ASSOCIATES

  33 Reuter Ave, Pittsfield, MA 01201

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