Pittsfield, MA Homes for Sale under $300,000

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  /29

  $299,900

  • 4 Beds
  • 3 Baths
  • 3,152 Sq Ft

  81 Calumet St, Pittsfield, MA 01201

  Rare opportunity to own a converted raised ranch home with full upper unit and lower unit for rental income. spacious yard, deck and detached garage.

  John Ciepiela BISHOP WEST REAL ESTATE

  81 Calumet St, Pittsfield, MA 01201
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  /4

  $35,000

  $5K PRICE DROP

  • Land
  • 13,068 Sq Ft
  • $116,667 per Acre

  103 Stearns Ave, Pittsfield, MA 01201

  Looking for land in West Pittsfield for your new build? This vacant lot is one of three contiguous lots located on Jones and Stearns Ave. All have public water and sewer available. The lots are zoned residential. Listed below assessed value!

  Erin Vincent BISHOP WEST REAL ESTATE

  103 Stearns 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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  /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
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  /10

  $49,900

  $10K PRICE DROP

  • Land
  • 3.1 Acres
  • $16,097 per Acre

  0 Eastbrook Ln, Pittsfield, MA 01201

  **Build Your Dream Home in the Exclusive Woodmonte Community!**Welcome to this DOUBLE Lot # 148-9 Eastbrook Lane, located in the prestigious and private Woodmonte neighborhood in Pittsfield, MA. This secluded double lot, listed at $59,900, is a rare find--completely prepped, fully serviced, and ideal for building your dream home!Enjoy the convenience of immediate ''Plug & Play'' construction,

  Nathan Girard ROYAL PROPERTY GROUP

  0 Eastbrook Ln, Pittsfield, MA 01201
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  /6

  $65,000

  • 12 Beds
  • 5 Baths
  • 4,032 Sq Ft

  48 Brown St, Pittsfield, MA 01201

  Opportunity knocks! This 4-family property has suffered significant fire damage and is being sold as-is for land value. Ideal tear down project with endless redevelopment potential. The lot includes a detached garage and offers ample space for new construction. Bring your vision and rebuild in a growing area with strong rental demand. Cash or construction financing only. All offers considered.

  Xavier Cruz Fathom Realty

  48 Brown St, Pittsfield, MA 01201
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  /3

  $35,000

  $5K PRICE DROP

  • Land
  • 17,424 Sq Ft
  • $87,500 per Acre

  90 Jones Ave, Pittsfield, MA 01201

  Looking for land in West Pittsfield for your new build? This vacant lot is one of three contiguous lots located on Jones and Stearns Ave. All have public water and sewer available. The lots are zoned residential. Listed below assessed value!

  Erin Vincent BISHOP WEST REAL ESTATE

  90 Jones Ave, Pittsfield, MA 01201
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  /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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  /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
• 

  

  /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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  /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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  /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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  /6

  $40,000

  • Land
  • 1.06 Acres
  • $37,736 per Acre

  Lot 42 Old Farm Ln, Pittsfield, MA 01201

  This is the lot you've been looking for! Over one acre in the wonderful Woodmonte Estates community. Located in West Pittsfield, you'll have easy access to all of the natural and cultural activities that the Berkshires has to offer. Get started on your dream home today!

  Josh Conant COHEN & WHITE ASSOCIATES

  Lot 42 Old Farm Ln, Pittsfield, MA 01201
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  /2

  $29,900

  • Land
  • 2.14 Acres
  • $13,972 per Acre

  0 Old Orebed Rd, Pittsfield, MA 01201

  Situated in a highly sought-after area of the region, this 2.14-acre lot provides an idyllic backdrop for building your forever residence or a seasonal Berkshire retreat. The property seamlessly blends outdoor recreation with tranquil nature, thanks to its prime location, a short drive from Jiminy Peak Mountain Resort and Mount Greylock. Endless year-round entertainment is at your fingertips

  Roseanne Casale DePalma BHHS Realty Professionals NON-MEMBER / RECIPROCAL

  0 Old Orebed Rd, 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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  /9

  $99,900

  $10K PRICE DROP

  • Land
  • 2.34 Acres
  • $42,692 per Acre

  0 Pleasant St, Pittsfield, MA 01201

  Attention developers! This is a great opportunity to own two adjacent buildable lots totaling 2.34 acres near downtown In Pittsfield, zoned RM (High Density Multifamily Residential).The lot with Parcel ID:I100002301 has 1.32 acres.The lot with Parcel ID:I100002026 has 1.02 acres.

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  0 Pleasant St, Pittsfield, MA 01201
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  /6

  $95,000

  • Land
  • 1.61 Acres
  • $59,006 per Acre

  497 Gale Ave, Pittsfield, MA 01201

  Build Your Berkshire Dream Home: Views, Convenience, & Site Prep Complete! Immerse yourself in the tranquil beauty of the Berkshires. This exceptional property offers the perfect balance of a scenic country retreat and effortless proximity to urban convenience. Situated along a picturesque road, the gently graded, partially cleared acreage showcases sweeping mountain and pastoral views--the

  Tammy Christen KELLER WILLIAMS REALTY

  497 Gale Ave, 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
• 

  

  /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

  $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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  /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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  /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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  /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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  /3

  $35,000

  $5K PRICE DROP

  • Land
  • 12,502 Sq Ft
  • $121,948 per Acre

  0 Jones Ave, Pittsfield, MA 01201

  Looking for land in West Pittsfield for your new build? This vacant lot is one of three contiguous lots located on Jones and Stearns Ave. All have public water and sewer available. The lots are zoned residential. Listed below assessed value!

  Erin Vincent BISHOP WEST REAL ESTATE

  0 Jones Ave, Pittsfield, MA 01201
• 

  

  /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
• 

  

  /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

Showing Results 41 - 80, Page 2 of 3