Pittsfield, MA Homes for Sale under $500,000

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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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  /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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  /40

  $439,000

  • 3 Beds
  • 1.5 Baths
  • 1,816 Sq Ft

  96 E Housatonic St, Pittsfield, MA 01201

  Seller is motivated for a new owner to fall in love with this beautifully maintained two-story brick colonial home. Nestled in one of the area's most sought after neighborhoods, this well-loved residence is filled with charm and character.The classic red brick exterior is settled on its lot with timeless curb appeal providing an irresistible first impression. Built in 1920, this home is

  Michelle Picard NOCHER REALTY

  96 E Housatonic St, 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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  /48

  $449,000

  Open Sat 2PM - 4PM

  • 4 Beds
  • 4 Baths
  • 3,360 Sq Ft

  153 Pomeroy Ave, Pittsfield, MA 01201

  Welcome to this immaculately maintained two-family home --a turnkey property that meets today's timeless standards!This choice 2-family home beautifully balances sophisticated living with incredible versatility, making it an ideal match for owner-occupants, multigenerational families, or savvy investors alike.Including features you are sure to love:Modern Living: Bright,

  Stephanie Rapisarda WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  153 Pomeroy 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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  /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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  /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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  /39

  $490,000

  • 3 Beds
  • 1.5 Baths
  • 2,119 Sq Ft

  444 Pomeroy Ave, Pittsfield, MA 01201

  Introducing 444 Pomeroy Ave, a true neighborhood icon! This one ticks all the boxes: Curb appeal to the max with mature perennial plantings, gracious front yard, private side yard with hot tub, and the true star of the show--the screened porch, which you won't want to leave in the summer. The home is spacious with a cooks kitchen and dining room, ample fire placed living room w/ built-ins galore.

  John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  444 Pomeroy 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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  /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
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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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  /49

  $365,000

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft

  136 Cadwell Rd, Pittsfield, MA 01201

  Well-updated split-level ranch offering plenty of space inside and out! Updated kitchen features granite countertops, newer cabinetry, tile flooring and stainless appliances. Hardwood floors flow through much of the main level. The primary bedroom offers a slider to the elevated 10x42 wood deck overlooking the fenced backyard. Main-level full bath features a double vanity and tiled tub/shower.

  Aimee Kelly eXp REALTY

  136 Cadwell Rd, Pittsfield, MA 01201
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  /71

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,218 Sq Ft

  46 Pinehurst Ave, Pittsfield, MA 01201

  YOUR PRIVATE RETREAT JUST A SHORT WALK TO PONTOOSUC LAKE WITH ENDLESS POTENTIAL!!! Tucked away at the Very End of the Street this 3 Bedroom, 2 Full Bath Home offers a Peaceful, Secluded Setting & Ready for Your Personal Vision & Unique Style. Convenient 1st Floor Laundry, The Eat-In Kitchen features Aristo Kraft Cabinetry, While the Cozy Private Deck is the Perfect Place to Relax, Unwind & Enjoy

  Kim Gordnier RE/MAX COMPASS

  46 Pinehurst Ave, Pittsfield, MA 01201
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  /28

  $334,900

  $15K PRICE DROP

  • 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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  /21

  $229,000

  • 4 Beds
  • 1 Bath
  • 1,404 Sq Ft

  62 Watson St, Pittsfield, MA 01201

  A diamond in the rough.Step into this 1900's colonial with 1400' sq ft on a large level corner lot. The first floor offer inviting kitchen; formal dining room; spacious living room, and convenient 1st floor laundry, large enough to add 1/2 bath. 2nd floor offers four bedrooms with closets and full bath.The road frontage on 2 streets leads to endless possibilities for your outdoor

  Barbara DeMers NOCHER REALTY

  62 Watson St, Pittsfield, MA 01201
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  /29

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,240 Sq Ft

  20 Cromwell Ave, Pittsfield, MA 01201

  Charming Cape-style home offering comfort, character, and a convenient location! This tastefully decorated three-bedroom, one-bath home features inviting living spaces and a layout that is both functional and easy to enjoy. A one-car garage provides added convenience, while the private backyard creates a peaceful retreat for relaxing or entertaining. Step outside to the deck and patio area--an

  Tracy Munger KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  20 Cromwell Ave, Pittsfield, MA 01201
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  /32

  $219,900

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 909 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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  /32

  $359,900

  • 4 Beds
  • 4 Baths
  • 3,180 Sq Ft

  1093 Tyler St, Pittsfield, MA 01201

  Investment Opportunity in Pittsfield! Well-maintained four-family flat offering four spacious 1-bedroom, 1-bath apartments. Each unit features separate utilities, providing tenants with individual responsibility for their utility costs. Natural gas heat and hot water add to the property's efficiency and appeal. Centrally located with convenient access to shopping, dining, schools, public

  Doug Collins Lamacchia Realty, Inc. - Dalton

  1093 Tyler St, Pittsfield, MA 01201
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  /7

  $239,000

  • Land
  • 6.25 Acres
  • $38,240 per Acre

  549 Churchill St, Pittsfield, MA 01201

  Ready to Build! Over 6 Acres of prime land with Views! Improvements include: Driveway, Well, and Septic plan. Bring your dream home plans and get started on this beautiful land on coveted Churchill Street. The House site is situated back from the road and elevated, giving you privacy and optimal views to the North and East. Around the corner from hiking and biking trails in Pittsfield State

  Mark Rosengren WILLIAM RAVEIS - BERKSHIRE

  549 Churchill St, Pittsfield, MA 01201
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  /23

  $209,900

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 866 Sq Ft

  139 2nd St, Pittsfield, MA 01201

  The home just passed an FHA appraisal and appraised over the asking price! This renovated home offers two bedrooms and two bathrooms. The first floor features an enclosed front porch, living room, foyer, full bathroom, laundry room and updated kitchen with new quartz countertops and stainless appliances. Upstairs you will find two bedrooms and half bathroom. Both of the bathrooms have been

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  139 2nd 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

  $289,900

  $30K PRICE DROP Pre-Foreclosure

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

  73 Plymouth St, Pittsfield, MA 01201

  Recently off market for needed maintenance on the exterior siding and landscaping, this home is now a must-see! Colonial style home is bright and airy featuring windows that invite abundant natural sunlight into every room. The main level offers a easy flow between the inviting living spaces and a convenient half-bath, while the second floor hosts three generous bedrooms and a full bath.A walk-up

  Jason Nocher NOCHER REALTY

  73 Plymouth St, Pittsfield, MA 01201
• 

  

  /21

  $339,900

  Open Sat 10AM - 12PM

  • 4 Beds
  • 1.5 Baths
  • 1,488 Sq Ft

  1981 East St, Pittsfield, MA 01201

  MOVE IN READY! Charming 4-bedroom, 1½-bath Cape in Southeast Pittsfield, located in Williams Elementary School district! This well-maintained home features beautiful hardwood floors, natural gas heat, a first-floor bedroom and walk-in shower, abundant storage, and a partially finished basement ideal for a family room, home office, or home gym. Enjoy the rare bonus of an included rear lot,

  Anthony Riello Lamacchia Realty, Inc. - Dalton

  1981 East St, Pittsfield, MA 01201

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