Pittsfield, MA Homes for Sale under $500,000

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  $475,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,702 Sq Ft

  24 Rockland Dr, Pittsfield, MA 01201

  This 3-bedroom, 2-bath ranch sits on a quiet street in one of Pittsfield's most desirable areas. The home has been meticulously maintained with an efficient layout and no wasted space. The kitchen was fully updated with quartz countertops. The basement has also been updated, adding real living space, not just storage. Both bedrooms have California Closet built-ins. Outside, a 32x16 inground pool

  Seth Alden ALTON & WESTALL REAL ESTATE AGENCY, LLC

  24 Rockland Dr, Pittsfield, MA 01201
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  $299,000

  $10K 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 an

  Ahliya Phillips KELLER WILLIAMS REALTY

  34 Hungerford St, Pittsfield, MA 01201
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  $349,900

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

  100 Essex St, Pittsfield, MA 01201

  *Video tour and floor plans availableThis lovely colonial home features two separate units, as it has been designed to offer an in-law apartment. The property has been tastefully renovated with new kitchens with quartz countertops, gorgeous updated bathrooms, fresh interior and interior paint, refinished gleaming hardwood floors, and other improvements, that include new roof, updated electrical

  Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.

  100 Essex St, Pittsfield, MA 01201
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  /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
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  $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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  /30

  $435,000

  Open Fri 4:30PM - 6PM

  • 3 Beds
  • 2 Baths
  • 1,732 Sq Ft

  99 Whittier Ave, Pittsfield, MA 01201

  Located in Southeast Pittsfield, this well-maintained Colonial offers timeless charm, thoughtful updates, and a floor plan that feels just as functional today as it did when it was built. Hardwood floors run throughout the home, and the inviting living room is anchored by a wood-burning fireplace with a bright sunroom just beyond--perfect for a home office, reading nook, or additional living

  Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

  99 Whittier Ave, Pittsfield, MA 01201
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  /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
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  $345,000

  Open Fri 4:30PM - 6PM

  • 3 Beds
  • 2 Baths
  • 1,275 Sq Ft

  22 Wealthy Ave, Pittsfield, MA 01201

  Welcome to 22 Wealthy Ave., located in the desirable Yankee Orchards neighborhood. Fresh, bright, and move in ready, this thoughtfully renovated home features beautifully refinished hardwood floors, a main level bedroom and full bath, plus two additional bedrooms upstairs with cedar lined closets, built in dresser drawers, and a newly renovated full bath. The updated kitchen includes a farmhouse

  Bresdin Mihlek COLDWELL BANKER REALTY

  22 Wealthy Ave, Pittsfield, MA 01201
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  /16

  $272,500

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft

  55 Howe Rd, Pittsfield, MA 01201

  Welcome to this well maintained 3-bedroom, 1-bath home tucked away at the end of a quiet side street, offering privacy, convenience, and a beautiful connection to nature. Inside, hardwood floors run throughout most of the home, reflecting years of attentive care and pride of ownership. Step outside to a spacious, fully fenced backyard featuring a deck with a remote-controlled retractable awning,

  Cody Gavin WILLIAM PITT SOTHEBY'S - LENOX

  55 Howe Rd, Pittsfield, MA 01201
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  $234,900

  $35K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,360 Sq Ft

  85 Edward Ave, Pittsfield, MA 01201

  This cherished family home is ready for it's next chapter. A welcoming front foyer opens to a spacious living room filled with natural light and featuring a classic wood-burning fireplace, seamlessly connected to a formal dining room ideal for entertaining. Beautiful hardwood floors, along with original wood molding and trim throughout add timeless character and warmth. The second floor offers

  Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

  85 Edward Ave, Pittsfield, MA 01201
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  /12

  $379,900

  • 6 Beds
  • 4 Baths
  • 2,944 Sq Ft

  60 Division St, Pittsfield, MA 01201

  Fantastic opportunity for investors or owner occupants! The town-house style unit would be perfect for owner occupants, as it offers plenty of space on two floors and two full baths! These units are renovated, with new flooring, cabinets, countertops, lighting, doors, and more! Pittsfield is a great location with so much to do! Enjoy hiking, shopping, shows, festivals, and more. Don't miss this

  Danielle Therrien Cameron Real Estate Group

  60 Division St, Pittsfield, MA 01201
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  /39

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft

  40 Longfellow Ave, Pittsfield, MA 01201

  Welcome to this sweet Southeast charmer, set on a corner lot that offers all the comfort and personality you desire! Step onto the adorable front porch and instantly feel at home. Inside, you'll find a convenient first-floor bedroom & full bathroom perfect for flexible living. The new dining room slider opens to a spacious deck with a screened gazebo, ideal for morning coffee or evening

  Rena Rose KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  40 Longfellow Ave, Pittsfield, MA 01201
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  /35

  $349,000

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

  15 Lillian St, Pittsfield, MA 01201

  Welcome home to this sweet split-level in desirable Southeast Pittsfield neighborhood. Offering 3 bedrooms and 1.5 baths, this well-maintained home features a spacious, well-appointed kitchen with granite countertops, abundant cabinetry, and great functionality for everyday living. Cozy up by the wood-burning fireplace or unwind in the inviting four-season room overlooking the deck and backyard.

  Victoria Standring Lamacchia Realty, Inc. - Dalton

  15 Lillian St, Pittsfield, MA 01201
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  /42

  $349,000

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

  62 Pomeroy Ave, Pittsfield, MA 01201

  Full of timeless charm and character, this spacious Colonial offers room for everyone! Featuring 4 bedrooms, 2 full bathrooms, a bright and inviting sunroom, and a convenient laundry room just off the kitchen, this home is designed for comfortable living. The large pantry provides excellent storage, while the flexible floor plan offers options for a dining room, family room, and living room to

  Andreea Duta BISHOP WEST REAL ESTATE

  62 Pomeroy Ave, Pittsfield, MA 01201
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  $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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  /34

  $469,900

  Open Sat 10:30AM - 12:30PM

  • 4 Beds
  • 1.5 Baths
  • 2,100 Sq Ft

  30 Lexington Pkwy, Pittsfield, MA 01201

  Welcome to 30 Lexington Parkway, an exceptionally cherished home in one of Southeast Pittsfield's most coveted neighborhoods. Brimming with timeless character, warmth, and pride of ownership, this impeccably maintained 4-bedroom home blends classic charm with everyday comfort. The inviting living spaces feature a stunning fireplace, hardwood floors, spacious eat-in kitchen, screened-in porch

  Anthony Riello Lamacchia Realty, Inc. - Dalton

  30 Lexington Pkwy, Pittsfield, MA 01201
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  /13

  $249,900

  $10K PRICE INCREASE

  • 6 Beds
  • 2 Baths
  • 1,928 Sq Ft

  17 Wallace Place, Pittsfield, MA 01201

  Recently renovated two-family home offering true turnkey convenience! Both units feature brand-new kitchens and bathrooms, updated heating systems, and stylish laminated flooring throughout. With all utilities fully separated, this low-maintenance property is ideal for investors seeking a hassle-free addition to their portfolio. Whether you're expanding your investments or starting fresh, this

  Michele Purcell Lamacchia Realty, Inc.

  17 Wallace Place, Pittsfield, MA 01201
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  /42

  $349,900

  Open Sat 4PM - 5:30PM

  • 4 Beds
  • 1.5 Baths
  • 1,668 Sq Ft

  43 State St, Pittsfield, MA 01201

  Recently renovated brick cape with attached garage, on a beautiful corner lot! The first floor offers spacious living room open to the updated large eat-in kitchen, with quartz countertops and new stainless appliances. The home has a total of 4 bedrooms and 1.5 baths. The first floor also features a renovated full bathroom and 2 bedrooms. Upstairs you will find a hat bathroom and two additional

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  43 State St, Pittsfield, MA 01201
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  /18

  $285,000

  $14K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,462 Sq Ft

  39 Meleca Ave, Pittsfield, MA 01201

  Spacious Southeast Pittsfield Ranch with great bones and endless potential! Generous room sizes and a thoughtful layout provide a wonderful foundation for additional updates that will make this home your own. A brand-new furnace offers added peace of mind, while the unfinished basement is ready for your vision, whether additional living space, a workshop, or recreation area. Outside, you'll find

  Victoria Standring Lamacchia Realty, Inc. - Dalton

  39 Meleca Ave, Pittsfield, MA 01201
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  /15

  $334,500

  • 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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  $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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  /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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  /20

  $289,000

  $21K PRICE DROP Pre-Foreclosure

  • 3 Beds
  • 1 Bath
  • 1,326 Sq Ft

  77 Imperial Ave, Pittsfield, MA 01201

  Well maintained cape on a perfect corner lot in The Orchards! The home features two bedrooms, full bath, kitchen and living room all on the main level. The second floor has an additional bedroom and storage. Wood burning fireplace and mountain views from the back yard. Efficient natural gas heating and solar panels from SunRun. Basement was at one time finished and certainly could be in the

  Derek Strzepa NOCHER REALTY

  77 Imperial Ave, Pittsfield, MA 01201
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  /38

  $449,900

  Open House 7/25 $19K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft

  81 Northumberland Rd, Pittsfield, MA 01201

  Move in ready! New roof and gutters in 2026, maintains original details but has been thoroughly updated. Located on a quiet, tree lined street, 81 Northumberland offers the kind of lifestyle one dreams about. Imagine walking your children to the nearby elementary school, stopping in for fresh pastries at the local bakery, grabbing a coffee on the way home, or enjoying an evening stroll through

  Tanya LeRose THE KINDERHOOK GROUP

  81 Northumberland Rd, Pittsfield, MA 01201
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  /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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  /41

  $313,900

  • 2 Beds
  • 2 Baths
  • 1,210 Sq Ft

  560 Crane Ave, Pittsfield, MA 01201

  More than meets the eye from the street view! Spacious embankment ranch welcomes you with gleaming hardwood flooring. Enter into the living room w cedar entry closet. What are YOU looking for? Here, you'll find a flexible floor plan featuring two or three bedrooms on the main floor (third bedroom off kitchen makes great formal dining option. Eat-in galley kitchen. Bonus space is the year-round

  Amanda Kmetz ROBERTS & ASSOC. REALTY, INC

  560 Crane Ave, Pittsfield, MA 01201
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  /14

  $445,000

  $50K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,998 Sq Ft

  191 Fort Hill Ave, Pittsfield, MA 01201

  Historic farmhouse property located on 5.2 acres +/- in rural setting in west Pittsfield farm country. Abuts undeveloped, wooded landscape to the east. Walk to Fort Hill Farm. Close to Pittsfield State Forest and downtown. First floor bathroom, second floor bedrooms. Newer replacement windows. Beautiful, centrally-located fireplace. Screened-in three season porch. Fresh paint and carpet

  Andrew Hillman Hillman Real Estate

  191 Fort Hill Ave, Pittsfield, MA 01201
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  /28

  $349,900

  • 2 Beds
  • 1 Bath
  • 1,088 Sq Ft

  112 Gamwell Ave, Pittsfield, MA 01201

  First time ever offered! Single Level Living Surrounded by Gardens You'll Fall in Love With Lovingly maintained by the original builder's family, this cherished ranch is ready for it's next chapter. Recently refinished hardwood floors, a fireplace, and a sun filled four season room with French doors overlooking established perennial gardens create a warm and inviting atmosphere. Years of

  Stacy Hebb NOCHER REALTY

  112 Gamwell Ave, Pittsfield, MA 01201
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  /51

  $445,000

  • 6 Beds
  • 4 Baths
  • 3,087 Sq Ft

  319 Fenn St, Pittsfield, MA 01201

  Prime investment opportunity in a highly desirable location just steps from the post office and within walking distance to downtown amenities, shopping, dining, and services. This well-maintained four-family property offers strong income potential with all separate utilities, allowing tenants to pay their own expenses and helping to maximize owner returns. Recent capital improvements include a

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  319 Fenn St, Pittsfield, MA 01201
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  /49

  $495,000

  • 4 Beds
  • 2.5 Baths
  • 1,855 Sq Ft

  70 Rockland Dr, Pittsfield, MA 01201

  Beautifully maintained 4-bedroom, 2.5-bath Colonial set on a quarter acre lot with privacy and curb appeal. Enjoy a spacious floor plan featurning a wood-burning fireplace, natural gas heat & hot water and newer replacement windows throughout, including new living room windows in 6/2026. The primary suite offers his-and-hers closets and a private bath. The finished lower level adds valuable

  Darcy Reid MOCKINGBIRD REAL ESTATE

  70 Rockland Dr, Pittsfield, MA 01201
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  /32

  $224,900

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 718 Sq Ft

  68 Orchard St, Pittsfield, MA 01201

  Recently renovated home with convenient first floor bedroom and full bathroom, and two additional bedrooms on the second floor. The front yard is fenced in. The backyard is a great space to gather. The basement has concrete floor and there is natural gas heat and hot water, and metered water. The home has a certificate of insulation and it shows how helpful it is as the utility bills are very

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  68 Orchard St, Pittsfield, MA 01201
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  /45

  $464,900

  $35K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,197 Sq Ft

  33 Eleanor Rd, Pittsfield, MA 01201

  Welcome to this charming 4-bedroom, 2-bath home offering the perfect blend of comfort, updates, and extra living space. The updated kitchen and renovated first-floor bath provide modern style and convenience, while the finished lower level adds versatile space for a family room, home office, gym, or guest area. A bright and inviting sunroom fills the home with natural light and offers the perfect

  Robin Moore 413 REAL ESTATE

  33 Eleanor Rd, Pittsfield, MA 01201
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  /5

  $235,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,947 Sq Ft

  15 Noble Ave, Pittsfield, MA 01201

  Two family duplex just outside of downtown. Featuring two bedrooms and one bathroom in each unit with hardwood floors. Off Street parking and separate utilities. Please reach out for interior photos.

  Cory Evangelisto NOCHER REALTY

  15 Noble Ave, Pittsfield, MA 01201
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  /34

  $299,900

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,566 Sq Ft

  73 Plymouth St, Pittsfield, MA 01201

  Perfectly situated on a spacious corner lot in a highly desirable neighborhood. This colonial style home is defined by its bright, airy atmosphere, featuring expansive windows that invite abundant natural sunlight into every room.The main level offers a seamless flow between the inviting living spaces and a convenient half-bath, while the second floor hosts three generous bedrooms and a full

  Jason Nocher NOCHER REALTY

  73 Plymouth St, Pittsfield, MA 01201
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  /28

  $207,000

  $22K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 902 Sq Ft

  1 Colt Rd Unit 1, Pittsfield, MA 01201

  Welcome to easy, in-town living at sought-after One Colt Road in a charming neighborhood. This first-floor condominium offers the perfect blend of convenience and comfort, just a short stroll to Berkshire Museum, Colonial Theatre, local restaurants, and boutique shops. Featuring 2 bedrooms and 1 bath, the layout is both functional and inviting. A rare screened porch extends your living space,

  Victoria Standring Lamacchia Realty, Inc. - Dalton

  1 Colt Rd Unit 1, Pittsfield, MA 01201
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  /20

  $289,000

  • 3 Beds
  • 1.5 Baths
  • 1,267 Sq Ft

  4 Garden St, Pittsfield, MA 01201

  Charming and well-maintained Cape offering 3 bedrooms and 1.5 baths in a desirable location just moments from Onota Lake. This inviting home features an open kitchen and dining area, creating a welcoming space for everyday living and entertaining. Full of character and warmth, the home also boasts a newly finished basement that provides additional living space perfect for a family room, home

  Elisha Poirier STONE HOUSE PROPERTIES, LLC

  4 Garden St, Pittsfield, MA 01201
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  /10

  $325,000

  • 4 Beds
  • 2 Baths
  • 2,378 Sq Ft

  89 Robbins Ave, Pittsfield, MA 01201

  Great Two family with some updates. Hardwood floor in dining room and bedrooms. Kitchen and bathroom with Ceramic floor. Newer Roof. Parking off street for 4 cars

  Al DeSouza First Option Properties Inc.

  89 Robbins Ave, Pittsfield, MA 01201
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  /31

  $349,000

  • 6 Beds
  • 2 Baths
  • 2,432 Sq Ft

  82 Parkside Ave, Pittsfield, MA 01201

  Enjoy this two-family flat home in the heart of Pittsfield. Featuring two spacious units, this property offers an excellent opportunity for both owner-occupants and investors alike. Enjoy efficient natural gas heating systems, updated gas hot water heaters and an enclosed front porch. Inside, you'll find functional floor plans filled with natural light. Step outside to enjoy a flat backyard

  Darcy Reid MOCKINGBIRD REAL ESTATE

  82 Parkside Ave, Pittsfield, MA 01201
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  /22

  $375,000

  • 4 Beds
  • 2.5 Baths
  • 1,985 Sq Ft

  40 Edward Ave, Pittsfield, MA 01201

  Located in a desirable neighborhood in Southeast Pittsfield, this three-bedroom, 1.5-bath home offers comfort, versatility, and exceptional value. The main residence features spacious living areas, large primary bedroom with walk in closet and laundry room, and a functional layout designed for everyday living. A standout feature of the property is the attached first floor apartment with an

  Molly DiGiovanni HOUSATONIC REAL ESTATE

  40 Edward Ave, Pittsfield, MA 01201
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  /25

  $295,000

  • 3 Beds
  • 1 Bath
  • 1,327 Sq Ft

  48 Plastics Ave, Pittsfield, MA 01201

  Renovated 3-Bedroom Cape in a Central Location. Welcome home to this newly renovated 3-bedroom Cape-style house, ideally situated in a convenient central location close to everyday amenities, local services, shopping, dining, and commuter routes. Combining classic Cape charm with fresh modern updates, this inviting home offers comfort, functionality, and move-in-ready appeal. Property highlights

  Dawn Vadnais MORESI REAL ESTATE PARTNERS

  48 Plastics Ave, Pittsfield, MA 01201

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