Pittsfield, MA Homes for Sale under $300,000

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  $25,000

  • Land
  • 1.51 Acres
  • $16,556 per Acre

  Lot #26 Old Farm Ln, Pittsfield, MA 01201

  Old Farm Lane, Lot #26 offers the perfect blend of wooded privacy and neighborhood community, while being tucked away on a quiet cul-de-sac. Utilities are in place with public sewer, private well, underground electric + gas.This lot borders the Pittsfield State Forest and offers close proximity to other year-round activities. It is also a short drive to the cultural hubs of Lenox,

  

  Diane Thorson

  WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  Lot #26 Old Farm Ln, Pittsfield, MA 01201
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  /9

  $45,000

  • Land
  • 1.08 Acres
  • $41,667 per Acre

  Lot 24 Old Farm Ln, Pittsfield, MA 01201

  This Woodmonte Estates lot offers a builder-ready parcel equipped with on-site utilities, including public sewer, a private well, and underground electric and gas.Tucked away in a premier luxury community, this location provides a serene, private setting while maintaining close proximity to year-round recreation. It is just a short drive to the renowned cultural hubs, skiing, lakes, and

  

  Diane Thorson

  WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  Lot 24 Old Farm Ln, Pittsfield, MA 01201
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  /4

  $54,900

  • Land
  • 2.42 Acres
  • $22,686 per Acre

  0 Old Orebed Rd, Pittsfield, MA 01201

  Discover the perfect setting for your dream home or Berkshire getaway on this breathtaking 2.42-acre parcel nestled in one of the region's most desirable locations. Ideally situated just minutes from Jiminy Peak Mountain Resort and near Mount Greylock, this property offers the ideal balance of peaceful natural surroundings and year-round adventure.Enjoy nearby access to skiing, hiking, lakes,

  

  Keytoria Jenkins

  BISHOP WEST REAL ESTATE

  0 Old Orebed Rd, Pittsfield, MA 01201
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  /6

  $55,000

  • Land
  • 1 Acre
  • $55,000 per Acre

  Lot 23 Old Farm Ln, Pittsfield, MA 01201

  This Woodmonte Estates lot offers a builder-ready parcel equipped with on-site utilities, including public sewer, a private well, and underground electric and gas.Tucked away in a premier luxury community, this location provides a serene, private setting while maintaining close proximity to year-round recreation. It is just a short drive to the renowned cultural hubs, skiing, lakes, and

  

  Diane Thorson

  WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  Lot 23 Old Farm Ln, Pittsfield, MA 01201
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  /7

  $59,900

  $20K PRICE DROP

  • Land
  • 1.23 Acres
  • $48,699 per Acre

  Lot 140 Westbrook Terrace, Pittsfield, MA 01201

  Nestled on a quiet street among upscale homes, this 1.23-acre lot offers a prime setting to build your custom residence. Underground utilities are available at the road for a seamless start. Enjoy the privacy and natural beauty of the Berkshires with easy access to downtown Pittsfield, Tanglewood, hiking trails, and more. Protective covenants preserve the integrity and lasting value of this

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  Lot 140 Westbrook Terrace, Pittsfield, MA 01201
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  /7

  $59,900

  $20K PRICE DROP

  • Land
  • 1.08 Acres
  • $55,463 per Acre

  Lot 144 Eastbrook Ln, Pittsfield, MA 01201

  Nestled on a quiet street among upscale homes, this 1.08-acre lot offers a prime setting to build your custom residence. Underground utilities are available at the road for a seamless start. Enjoy the privacy and natural beauty of the Berkshires with easy access to downtown Pittsfield, Tanglewood, hiking trails, and more. Protective covenants preserve the integrity and lasting value of this

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  Lot 144 Eastbrook Ln, Pittsfield, MA 01201
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  /21

  $224,500

  • 1 Bed
  • 1 Bath
  • 1,056 Sq Ft

  42 Churchill Crest Unit 42, Pittsfield, MA 01201

  Welcome to Churchill Crest, where timeless elegance, comfort and the beauty of the Berkshires comes together. Inside you'll find 1 bedroom 1 bathroom with spacious living room with wood burning fireplace, dining and kitchen. From the living room is a private deck. Under the main level is a private garage and lower level offers laundry. Community offers a heated inground pool with pavilion space

  

  Laura Arseneau

  PAULA MCLEAN REALTORS INC.

  42 Churchill Crest Unit 42, Pittsfield, MA 01201
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  /7

  $35,000

  • Land
  • 1.08 Acres
  • $32,407 per Acre

  Lot 25 Old Farm Ln, Pittsfield, MA 01201

  This Woodmonte Estates lot offers a builder-ready parcel equipped with on-site utilities, including public sewer, a private well, and underground electric and gas.Tucked away in a premier luxury community, this location provides a serene, private setting while maintaining close proximity to year-round recreation. It is just a short drive to the renowned cultural hubs, skiing, lakes, and

  

  Diane Thorson

  WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  Lot 25 Old Farm Ln, Pittsfield, MA 01201
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  /57

  $249,900

  • 6 Beds
  • 2 Baths
  • 2,600 Sq Ft

  158 Linden St, Pittsfield, MA 01201

  Welcome to 158-160 Linden Street in Pittsfield. This centrally located 2 family boast 3 bedrooms, 1 bath and laundry in each unit. The entire home was renovated approximately 25 years ago and has been well maintained since. Separate electric meters for each unit and they both offer electric baseboard heat that is not included in the rent. On the exterior you will find a large fenced in side yard,

  Doug Collins Lamacchia Realty, Inc. - Dalton

  158 Linden St, Pittsfield, MA 01201
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  /2

  $39,900

  • Land
  • 6,438 Sq Ft
  • $269,966 per Acre

  0 Courtland Place, Pittsfield, MA 01201

  Cleared City lot with public water and sewer

  John Ciepiela BISHOP WEST REAL ESTATE

  0 Courtland Place, 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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  $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.

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  3 Clarendon St, Pittsfield, MA 01201
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  /8

  $29,900

  • Land
  • 14,810 Sq Ft
  • $87,941 per Acre

  I110019004 Brown St, Pittsfield, MA 01201

  Priced well below assessed value. Zoning verification states: The property is a .344-acre lot having 100 feet of frontage on Brown Street and 50 feet of frontage on Scammell Ave. There are no structures on the property. The lot meets the minimum dimensional requirements for development.

  Laurie Atkinson KELLER WILLIAMS REALTY

  I110019004 Brown 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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  /5

  $35,000

  $4K PRICE DROP

  • Land
  • 17,859 Sq Ft
  • $85,366 per Acre

  33 Circular Ave, Pittsfield, MA 01201

  Building lot that is well located and cleared in downtown Pittsfield. City lot is 0.41 acres, approved for building Single Family or Multi-Family up to 4 units and fits within the Multi-Family Residential zone (R-M). Walk-able and close to all amenities including restaurants, grocery stores, shops and public transportation. Water, sewer and gas available on the street. Proximity to the region's

  Cory Evangelisto NOCHER REALTY

  33 Circular Ave, Pittsfield, MA 01201
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  /15

  $189,000

  $6K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  81 Dartmouth St Unit 208, Pittsfield, MA 01201

  Move right into this beautifully updated condo featuring an open floor plan, soaring ceilings and oversized windows that fill the space with natural light. The modern kitchen boasts quartz countertops, stainless steel appliances and flows seamlessly into the living and dining areas - perfect for everyday living and entertaining. Bamboo flooring adds warmth throughout, while the updated bath

  Darcy Reid MOCKINGBIRD REAL ESTATE

  81 Dartmouth St Unit 208, Pittsfield, MA 01201
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  /2

  $60,000

  • Land
  • 7,840 Sq Ft
  • $333,333 per Acre

  95 Union St, Pittsfield, MA 01201

  95 Union Street offers a rare downtown Pittsfield infill land opportunity within the Downtown Creative District. The parcel is approximately 0.18 acres / 7,661 SF and is currently land only, with frontage on Union Street near the Center Street extension. Flexible DCD zoning supports a vibrant mix of potential uses, including arts and creative uses, retail, restaurant/food and beverage concepts,

  Cole Ungar SKYTOP ASSET MANAGEMENT

  95 Union St, Pittsfield, MA 01201
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  /29

  $269,000

  $30K 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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  /40

  $279,900

  Open Sat 11AM - 12:30PM

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  80 Calumet St, Pittsfield, MA 01201

  This colonial home has been recently renovated, with improvements that include but are not limited to new roof, updated kitchen and bathroom, new flooring and freshly painted interior! Upon entering the home you will be welcomed by an adorable enclosed porch. The first floor offers a lovely living room, open to the dining area. The kitchen is simply beautiful, featuring quartz countertops and new

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  80 Calumet St, Pittsfield, MA 01201
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  /27

  $274,000

  $11K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,388 Sq Ft

  16 S Atlantic Ave, Pittsfield, MA 01201

  Step inside this turnkey 4-bedroom, 1.5-bath New England farmhouse and immediately feel at home. Additional room/office space on the first floor. Fully renovated in 2022 and freshly painted from top to bottom (2026), this vacant beauty is completely ready for its next chapter.The traditional farmhouse aesthetic offers timeless appeal, while the 2022 updated bring modern comfort and style.

  Maria Cano NOCHER REALTY

  16 S Atlantic Ave, 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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  /27

  $95,500

  $24K PRICE DROP

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

  1 Lakewood Cir, Pittsfield, MA 01201

  Bring your clothes and move into this immaculate well maintained two bedroom/two bathroom mobilehome is located on a wonderful corner lot.Very comfortable living space and all furniture will convey with the sale.The spacious deck is great for entertaining or just relaxing on- also included is a shed/workshop that has electricity.

  Michelle Picard NOCHER REALTY

  1 Lakewood Cir, Pittsfield, MA 01201
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  /11

  $42,000

  • Land
  • 1.31 Acres
  • $32,061 per Acre

  39 Old Farm Ln, Pittsfield, MA 01201

  This Ready to Build exceptional 1.31-acre cul-de-sac homesite in Woodmonte Estates is ready for your custom dream home, with town sewer, private well, underground electric & gas, cable availability, and paved roads already in place. Assessed at $74,000 and selling it for $42,000.Located in one of Pittsfield's premier luxury communities, the property offers a peaceful, private setting while

  Judi Panzano HOUSATONIC REAL ESTATE

  39 Old Farm Ln, 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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  /21

  $275,000

  • 12 Beds
  • 4 Baths
  • 4,200 Sq Ft

  112 Union St, Pittsfield, MA 01201

  The building has the potential to be a great income producing property. There are 4 units with plenty of off street parking. It has vinyl siding, replacement windows and is close to the downtown area. 3 Units are lead safe. Check the documents section referencing a letter from the City Commissioner. The owner is in the process of having plans drawn by a local architect firm to address the scope

  Janet Benoit MOCKINGBIRD REAL ESTATE

  112 Union St, Pittsfield, MA 01201
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  /20

  $199,000

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

  39 Hull Ave, Pittsfield, MA 01201

  Conveniently located near downtown Pittsfield, this home sits on .14 acres with a backyard for entertaining and garage for storage. The first floor offers a living room, dining room, kitchen, bathroom, and a flexible space with many possibilities. Upstairs are 3 bedrooms, a full bathroom, and a walk-up attic. The walk-out basement provides additional potential. Major updates include cellulose

  Patricia Molina CENTURY 21 NORTHEAST

  39 Hull Ave, Pittsfield, MA 01201
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  /23

  $209,900

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 866 Sq Ft

  139 Second St, Pittsfield, MA 01201

  The home just passed an FHA appraisal at over the listing 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 renovated! Other

  Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.

  139 Second St, Pittsfield, MA 01201
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  /26

  $299,000

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,533 Sq Ft

  38 Connecticut Ave, Pittsfield, MA 01201

  Welcome home to this charming and well-maintained three-bedroom, two-bath property located in a desirable neighborhood just moments from Allendale School, downtown Pittsfield, shopping, dining, and everyday conveniences. This inviting home offers a wonderful blend of character and comfort, featuring beautiful hardwood floors in excellent condition, vinyl replacement windows, and a cozy

  Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

  38 Connecticut Ave, Pittsfield, MA 01201
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  /16

  $249,900

  $15K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 3,510 Sq Ft

  32 Westminster St, Pittsfield, MA 01201

  Calling all investors and hands-on owner-occupants! This 3-unit multi-family offers 15 rooms, 6 bedrooms, and 3 full baths across 3,510 sq ft on a 0.17-acre lot. The owner has already made key updates, including some new flooring, fresh paint, updated electric, and a new bulkhead, giving you a head start on renovations. Still needed: updated heating systems, roof work, wall patching, and final

  Clifford Ponte KELLER WILIAMS SOUTH WATTUPA

  32 Westminster St, Pittsfield, MA 01201
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  /10

  $59,900

  • Land
  • 5,662 Sq Ft
  • $460,769 per Acre

  69 Tyler St, Pittsfield, MA 01201

  Commercial Lot located in a prime business district. Just steps away from one of Pittsfield's busiest intersections Tyler St and Rt 7 North and next to the Berkshire Medical Center Campus, the possibilities are endless. A note, the underlying zoning for the parcel is B-G, which has no setback requirements and no lot minimum size. This means that there are many options you could choose from if you

  Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  69 Tyler St, Pittsfield, MA 01201
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  /15

  $195,000

  $16K PRICE DROP

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

  47 Lake St, Pittsfield, MA 01201

  Whether you are looking to add to your investment portfolio or purchase a property with the potential to offset your mortgage with rental income, this two-family offers plenty of possibilities. Featuring two separate units with a total of 3 bedrooms and 2 full baths, the property provides approximately 1,923 square feet of living space. Separate electric meters add convenience for an investor,

  Lisa Kelley MACCARO REAL ESTATE

  47 Lake St, Pittsfield, MA 01201
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  /8

  $95,000

  • Land
  • 0 Sq Ft

  499 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

  499 Gale Ave, Pittsfield, MA 01201
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  /29

  $289,900

  • 6 Beds
  • 2 Baths
  • 2,060 Sq Ft

  38 Grove St, Pittsfield, MA 01201

  Two-family flat ideally located and offering an excellent opportunity for investors. Each apartment features 3 bedrooms and separate utilities. The property is serviced by public water and sewer and includes two electric meters, two boilers, and two hot water heaters, with natural gas heating and hot water.The first-floor unit features a newer kitchen.The second-floor unit offers an

  Jose Larios Lamacchia Realty, Inc. - Dalton

  38 Grove 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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  /10

  $189,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,493 Sq Ft

  23 Walnut St, Pittsfield, MA 01201

  Opportunity awaits with this home offering approximately 1,493 square feet of living space on a generous 12,807 sq. ft. lot. This property presents a great starter-home opportunity with solid bones and plenty of potential for updates and personalization. The spacious lot provides ample room for outdoor enjoyment and future improvements. With some TLC, this home offers an excellent opportunity to

  Derek Greene The Greene Realty Group

  23 Walnut St, Pittsfield, MA 01201
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  /20

  $199,900

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

  395 Cheshire Rd Unit 106, 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 106, Pittsfield, MA 01201
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  /8

  $129,900

  $9K PRICE DROP

  • Land
  • 5.68 Acres
  • $22,870 per Acre

  132 Cascade St, Pittsfield, MA 01201

  Build your Berkshire dream on this 5.68-acre parcel ideally located on a paved road just moments from Pittsfield State Forest. Offering a beautiful blend of privacy and accessibility, this property provides the perfect setting for a year-round home or weekend retreat. Enjoy easy access to miles of trails, hiking, biking, and outdoor recreation, all while being just a short drive to downtown

  Elisha Poirier STONE HOUSE PROPERTIES, LLC

  132 Cascade St, Pittsfield, MA 01201
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  /14

  $104,990

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,120 Sq Ft

  7 Ash Ln, Pittsfield, MA 01201

  Move-in ready and tastefully updated! Welcome to this charming 2-bedroom, 1-bath manufactured home in the desirable Lake Onota Village community. The bright, inviting interior features an open-concept living area, an updated kitchen with modern finishes and appliances, an updated bathroom, new flooring, and fresh paint throughout. Relax on the front porch and enjoy the convenience of a storage

  Sai Kamasani Lamacchia Realty, Inc. - Dalton

  7 Ash Ln, Pittsfield, MA 01201
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  /21

  $229,900

  $6K PRICE DROP

  • 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

  $280,000

  $30K PRICE DROP

  • 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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