Lanesboro, MA Homes for Sale

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  /15

  $1,719,000

  • 37 Beds
  • 24 Baths
  • 21,162 Sq Ft

  306 South St, Pittsfield, MA 01201

  Offered as a 7-property portfolio, totaling 21 units, this package includes a mix of multifamily properties and a single-family home with value-add potential. Several units are tenant-occupied, providing immediate income with upside potential, while others units require renovation, allowing investors to implement a phased improvement strategy. The portfolio currently generates an in-place NOI of

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  306 South St, Pittsfield, MA 01201
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  /4

  $389,900

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

  0 Broadview Terrace, Pittsfield, MA 01201

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

  

  Syrah Bradley

  BISHOP WEST REAL ESTATE

  0 Broadview Terrace, Pittsfield, MA 01201
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  /4

  $399,900

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

  Lot 4 Tanner St, Pittsfield, MA 01201

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

  

  Syrah Bradley

  BISHOP WEST REAL ESTATE

  Lot 4 Tanner St, Pittsfield, MA 01201
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  /4

  $215,000

  • Land
  • 14.3 Acres
  • $15,035 per Acre

  L16 Reservoir Rd, Out-Of State, MA 99999

  Discover an unparalleled opportunity with this stunning 14.3-acre parcel, perfect for building your dream home or if needed, subdividing into its original three lots. Featuring a pre-installed driveway, electrical service with a transformer, and a large 36 x 50 foundation that was started for a garage/barn, this property is both convenient and versatile. Enjoy the natural beauty of streams,

  

  Gary Fuls Jr

  Gary L Fuls DBA Re/MAX Transit

  L16 Reservoir Rd, Out-Of State, MA 99999
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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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  /11

  $450,000

  $150K PRICE DROP

  • Land
  • 3.44 Acres
  • $130,814 per Acre

  117 Lime Kiln Rd, Lenox, MA 01240

  Ready to build! Build your own Berkshire Home on this beautiful 3.44 acre parcel in the heart of the Berkshires! The land is partially cleared and ready for construction, with septic design plans already with public water and power on the street. Set on a quiet road, this property offers privacy with a true Berkshire feel while being close to many cultural attractions including, Tanglewood, The

  

  Laura Arseneau

  PAULA MCLEAN REALTORS INC.

  117 Lime Kiln Rd, Lenox, MA 01240
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  /4

  $399,900

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

  Lot 5 Tanner St, Pittsfield, MA 01201

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

  

  Syrah Bradley

  BISHOP WEST REAL ESTATE

  Lot 5 Tanner St, Pittsfield, MA 01201
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  /4

  $399,900

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

  Lot 6 Tanner St, Pittsfield, MA 01201

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

  

  Syrah Bradley

  BISHOP WEST REAL ESTATE

  Lot 6 Tanner St, Pittsfield, MA 01201
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  /32

  $799,900

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  369 Housatonic St, Lenox, MA 01240

  A UNIQUE OPPORTUNITY TO OWN A SPACIOUS LENOX HOME IN A PRIVATE, COUNTRY SETTING AT A REASONABLE PRICE. 4BR, 2.5 BATHS, WITH HARDWOOD FLOORS, OPEN KITCHEN/DINING AREA, LARGE OPEN DECK, PELLET STOVE AND AN IN-GROUND POOL. LOVELY LANDSCAPING WITH STONE WALLS, GARDENS AND OPEN LAWN AREA FOR ATHLETICS OR JUST RELAXING. GREAT CENTRAL LOCATION, A SHORT DISTANCE TO TANGLEWOOD, TOWN AND YOUR FAVORITE

  Allen Bassen

  BERKSHIRE HOMES AND CONDOS

  369 Housatonic St, Lenox, MA 01240
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  /56

  $590,000

  • 3 Beds
  • 2 Baths
  • 1,858 Sq Ft

  178 New Lenox Rd, Lenox, MA 01240

  This property has an immaculate fenced in back yard for all your summer activities. Inside boasts beautiful hardwood floors, Full bath on the 1st and 2nd Level. Large mudroom from the main entrance for all you winter and mud season needs. A paved driveway with plenty of private parking. A walkout from the lower level to the parking area with a tuck under car port. Recently painted exterior and a

  

  Cristian Sanchez

  COHEN & WHITE ASSOCIATES

  178 New Lenox Rd, Lenox, MA 01240
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  /33

  $385,000

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

  5 Putnam Ave, Pittsfield, MA 01201

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

  

  Laura Arseneau

  PAULA MCLEAN REALTORS INC.

  5 Putnam Ave, Pittsfield, MA 01201
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  /84

  $1,650,000

  • 7 Beds
  • 6.5 Baths
  • 5,693 Sq Ft

  20 E Dugway Rd, Lenox, MA 01240

  Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to

  

  Nick Geranios

  WILLIAM PITT SOTHEBY'S - LENOX

  20 E Dugway Rd, Lenox, MA 01240
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  /24

  $389,900

  • 3 Beds
  • 1.5 Baths
  • 2,178 Sq Ft

  38 Hubbard St, Lenox, MA 01240

  Tucked into a peaceful wooded setting in Lenox, this architecturally distinctive contemporary home offers 2,189 square feet of living space on a private half acre lot. Designed with an asymmetrical exterior and a split level floor plan spanning three levels, this home offers unique character. Large windows fill the interior with natural light, while the open living areas create an inviting space.

  Mariah Worth Lamacchia Realty, Inc. - Dalton

  38 Hubbard St, Lenox, MA 01240
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  /29

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  18 Elaine Ave, Dalton, MA 01226

  Enjoy this beautifully maintained one-level living home in the heart of Dalton offering a spacious and convenient layout with thoughtful updates throughout. The open floor plan creates a seamless flow between the main living areas, featuring two spacious living rooms filled with natural light and excellent flexibility for everyday living, relaxing, entertaining, or working from home. The

  Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

  18 Elaine Ave, Dalton, MA 01226
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  /42

  $339,900

  $20K PRICE DROP

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

  112 Plunkett St, Pittsfield, MA 01201

  Welcome to this impeccably maintained 4-bedroom, 2-full-bath residence offering comfort, style, & exceptional outdoor living. Every room has been recently painted! The updated kitchen features all new appliances, while the spacious layout provides plenty of room for family, guests, or a home office. Step outside & discover your own private backyard retreat. Relax under the covered porch,

  Mary Jane Dunlop BISHOP WEST REAL ESTATE

  112 Plunkett St, Pittsfield, MA 01201
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  /62

  $799,900

  $90K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 3,370 Sq Ft

  5 Crofut St, Pittsfield, MA 01201

  Own Pittsfield History in this distinctive solidly built Georgian-style brick estate set proudly atop a hill in this coveted enclave of stately residences. Live on historic Crofut St. near the esteemed Pittsfield Country Club, Up Street Cultural Art District and ideally minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  5 Crofut St, Pittsfield, MA 01201
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  /37

  $229,999

  • 2 Beds
  • 1 Bath
  • 863 Sq Ft

  34 Cummings Ave, Pittsfield, MA 01201

  This cozy Cape home feels like country, yet you're just minutes from markets, restaurants, the music of Tanglewood, Herman Melville's Arrowhead, and other cultural delights of the Berkshires. The first floor features a bedroom and bathroom while upstairs what was once the attic now consists of an expansive second bedroom. There's a service porch with space for storage and appliances, if you want

  Carolyn Reuben Green KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  34 Cummings Ave, 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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  /16

  $149,000

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 617 Sq Ft

  108 E Housatonic St Unit 7, Pittsfield, MA 01201

  Great location in Southeast Pittsfield..Short walk to downtown Pittsfield.. Lovely unit with hardwood floors in the Living room and Bedroom......Nice sized balcony (facing the morning sun) to relax on..Coin operated laundry just a few steps down into the lower level.. Storage locker is available in an upstairs area through the door on the balcony. The unit sq footage is 617 and is recorded in

  Barbara K Greenfeld SIGNATURE ASSOCIATES

  108 E Housatonic St Unit 7, Pittsfield, MA 01201
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  /53

  $1,190,000

  $485K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,991 Sq Ft

  9 October Hill Dr, Lenox, MA 01240

  Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a

  Paula McLean PAULA MCLEAN REALTORS INC.

  9 October Hill Dr, Lenox, MA 01240
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  /32

  $629,000

  $46K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,562 Sq Ft

  18 Willow Ln, Lenox, MA 01240

  Nestled on a peaceful street, this inviting 3 bedroom, 1.5 bath home offers the perfect blend of comfort and convenience. Step inside to find a bright and welcoming living space filled with natural light, a cozy dining area, and a functional kitchen ready for your personal touch. The three bedrooms provide plenty of room for family, guests, or a home office, while the updated half bath adds extra

  Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  18 Willow Ln, Lenox, MA 01240
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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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  /30

  $269,900

  $30K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,362 Sq Ft

  1952 East St, Pittsfield, MA 01201

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

  Melinda Boos KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  1952 East St, Pittsfield, MA 01201
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  /43

  $489,000

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

  16 Trova Terrace, Pittsfield, MA 01201

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

  Matt Jarck WILLIAM PITT SOTHEBY'S - LENOX

  16 Trova Terrace, Pittsfield, MA 01201
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  /43

  $414,900

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

  19 Roselyn Dr, Pittsfield, MA 01201

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

  Allison Pacelli PACELLI ZEPKA

  19 Roselyn Dr, Pittsfield, MA 01201
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  /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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  /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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  /17

  $335,000

  $33K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft

  4 Morgan Manor Unit 4, Lenox, MA 01240

  Lenox in-town condo.....ready for a new owner, need a close location to Tanglewood, Shakespeare and Company, The Mount, Venfort Hall, Kennedy Park, Pleasant Valley Wildlife Sanctuary? Well this is the perfect location!2 bedrooms, 1 full bath, wood floors and carpeted bedrooms, great light ....fully applianced kitchen....Easy to show!

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  4 Morgan Manor Unit 4, Lenox, MA 01240
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  /50

  $7,975,000

  • 8 Beds
  • 6.5 Baths
  • 9,364 Sq Ft

  399 Under Mountain Rd, Lenox, MA 01240

  Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  399 Under Mountain Rd, Lenox, MA 01240
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  /29

  $289,000

  $10K PRICE DROP

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

  162 W Housatonic St, Pittsfield, MA 01201

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

  Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

  162 W Housatonic St, Pittsfield, MA 01201
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  /50

  $519,000

  • 3 Beds
  • 2.5 Baths
  • 2,136 Sq Ft

  133 Holmes Rd, Pittsfield, MA 01201

  Beautiful combination of modern renovations with historic character! The first floor boasts an easy living circular flow with kitchen, dining and living room with stunning floors and washed with fabulous natural light. Family room tucked away for a more intimate space, large laundry room, mudroom and half bath. The second level includes a primary bedroom with an updated en suite full bath and

  Cortney Dupont COHEN & WHITE ASSOCIATES

  133 Holmes Rd, Pittsfield, MA 01201
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  /37

  $529,900

  • 6 Beds
  • 3 Baths
  • 3,320 Sq Ft

  136 Pomeroy Ave, Pittsfield, MA 01201

  Step into timeless elegance in this exceptional 6-bedroom, 3-bath historic residence, where classic architectural details blend seamlessly with thoughtful modern updates. Meticulously maintained and enhanced over the years, this one-of-a-kind home showcases the craftsmanship and character rarely found today. From the moment you enter, you'll be captivated by the grand, sun-filled rooms, gleaming

  Robin Moore 413 REAL ESTATE

  136 Pomeroy Ave, Pittsfield, MA 01201
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  /24

  $345,000

  $40K PRICE DROP

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

  37 Melville St, Pittsfield, MA 01201

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

  Cory Evangelisto NOCHER REALTY

  37 Melville St, Pittsfield, MA 01201
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  /34

  $560,000

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft

  290 Barker Rd, Pittsfield, MA 01201

  Welcome to this stately raised ranch nestled in one of Pittsfield's most sought-after neighborhoods--Barkerville. Offering 1,896 square feet of thoughtfully designed living space, this home blends comfort, efficiency, and natural beauty in a truly special setting.Set on a cozy, private lot, the property is framed by mature evergreen trees, classic stone walls, and a peaceful brook flowing through

  Melinda Boos KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  290 Barker Rd, Pittsfield, MA 01201
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  /20

  $209,000

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

  232 First St, Pittsfield, MA 01201

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

  Anthony Riello Lamacchia Realty, Inc. - Dalton

  232 First St, Pittsfield, MA 01201
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  /28

  $298,000

  $14K PRICE DROP

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

  50 W Housatonic St, Pittsfield, MA 01201

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

  Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

  50 W Housatonic St, Pittsfield, MA 01201
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  /41

  $289,900

  Pre-Foreclosure

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

  246 Dalton Ave, Pittsfield, MA 01201

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

  Doug Collins Lamacchia Realty, Inc. - Dalton

  246 Dalton Ave, Pittsfield, MA 01201
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  /3

  $349,900

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

  75 3rd St, Pittsfield, MA 01201

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

  Janet Benoit MOCKINGBIRD REAL ESTATE

  75 3rd St, Pittsfield, MA 01201
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  /11

  $235,000

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

  20 Curtis Terrace, Pittsfield, MA 01201

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

  ShaDina Johnson Berkshire Hathaway HomeServices Realty Professionals

  20 Curtis Terrace, Pittsfield, MA 01201

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