Berkshire County MA Homes for Sale

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  /8

  $54,900

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

  1 Old Orebed Rd, New Ashford, MA 01237

  Price improvement, seller's are MOTIVATED!!!Stunning 2.42-Acre Lot with Breathtaking Mountain Views! Prime location just minutes from the popular Jiminy Peak Ski Resort, Mt. Greylock. The property provides an excellent opportunity to build your dream home or vacation retreat, surrounded by nature's beauty and outdoor adventure. Enjoy access to skiing, hiking, lakes and more, while being

  

  Keytoria Jenkins

  THE KINDERHOOK GROUP

  (866) 436-0912

  1 Old Orebed Rd, New Ashford, MA 01237
• 

  

  

  /15

  $110,000

  • Land
  • 4.62 Acres
  • $23,810 per Acre

  0 Dalton Division Rd, Pittsfield, MA 01201

  Well located parcels with 4.2 acres of development land zoned RG with an attached .4 acre lot zoned R12. Sale includes all engineering work to date, including wetlands delineation, site plans, etc... All utilities available including water, sewer & natural gas. Possibilities include 19-20 Garden Style Apartments, 5 or 7 lot subdivision or a 3 lot ANR subdivision. Property abuts large apartment

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 366-3881

  0 Dalton Division Rd, Pittsfield, MA 01201
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  /6

  $325,000

  • Land
  • 21.7 Acres
  • $14,977 per Acre

  0 Sisson Hill Rd Unit 248042, New Marlborough, MA 01230

  21.7 wooded acres on one of South County's ''best-kept-secret'' back country roads, yet just minutes away from Great Barrington, Sheffield and the bucolic villages of New Marlborough. Discover nature, privacy & a unique sense of peace on this rare piece of land. The land has been perc tested, seller will provide final survey prior to closing. Map in documents shows proposed new boundaries for

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 848-6618

  0 Sisson Hill Rd Unit 248042, New Marlborough, MA 01230
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  /29

  $469,000

  • 3 Beds
  • 3 Baths
  • 1,685 Sq Ft

  7 Silverbrook Rd, Sandisfield, MA 01255

  Riverfront on Silverbrook, Feels like new. Beautiful Setting. 3 bedrooms 3 baths. Sit on the back deck and watch the water flow. Inside you will find a huge kitchen with stained concrete counter tops and Stainless appliances. Primary with full bath is on the main floor along with laundry and a 1/2 guest bath. Upstairs 2 large bedrooms with a full bath. The lower-level family room is partially

  

  Ginger Conner

  RED HORSE REAL ESTATE, LLC

  (413) 728-1878

  7 Silverbrook Rd, Sandisfield, MA 01255
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  /11

  $1,176,800

  • 4 Beds
  • 3.5 Baths
  • 2,634 Sq Ft

  411 Churchill St, Pittsfield, MA 01201

  To Be Built Home - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 8.94-acre lot (MLS #248342), featuring a

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 343-4823

  411 Churchill St, Pittsfield, MA 01201
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  /6

  $395,000

  • Land
  • 3.3 Acres
  • $119,697 per Acre

  9 Wheatleigh Dr, Stockbridge, MA 01262

  RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 722-5098

  9 Wheatleigh Dr, Stockbridge, MA 01262
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  /50

  $845,000

  • 4 Beds
  • 3.5 Baths
  • 2,955 Sq Ft

  9 Castle Hill Rd, Stockbridge, MA 01262

  Tucked away on a quiet country road just minutes from the heart of historic Stockbridge, this 3.49-acre property pairs timeless New England charm with modern comforts. The star of the show is a beautifully updated red farmhouse with 3 bedrooms and 2.5 bathrooms, set on a sunny, bucolic lot that feels worlds away--yet is moments from downtown.The main house has been thoughtfully renovated,

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 269-8632

  9 Castle Hill Rd, Stockbridge, MA 01262
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  /16

  $125,000

  • 3 Beds
  • 2 Baths
  • 1,804 Sq Ft

  77 Front St, North Adams, MA 01247

  This is currently occupied as a single family. It is a Centrally located two family. Located a short distance from Downtown North Adams , Mass MoCA and Groundart Studios. The home is currently being used as single family. The second egress to unit 2 will to be restored. The property is a double lot. There is a building lot to the left of the existing home.

  

  Michael Hernandez

  360BERKSHIRE REALTY GROUP

  (413) 350-1352

  77 Front St, North Adams, MA 01247
• 

  /2

  $300,000

  • 6 Beds
  • 4 Baths
  • 4,136 Sq Ft

  Unlisted Address

  THIS LISTING TO BE SOLD AS PART OF A 11 UNIT PACKAGE: Other properties included are located at 40-42 Henry Ave. Pittsfield, MA 01201 and 27-31 Pleasant St. Pittsfield, MA 01201. Acquire this three multifamily package offered at $920,000. Income & expense and rent roll document available in documents and or upon request.

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 779-3154

  Unlisted Address
• 

  

  /7

  $809,900

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  403 Churchill St, Pittsfield, MA 01201

  To Be Built - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 2.14-acre lot (MLS # 248343), featuring a private

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 741-2226

  403 Churchill St, Pittsfield, MA 01201
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  /92

  $689,900

  • 4 Beds
  • 5 Baths
  • 2,748 Sq Ft

  10 Lillybrook Rd, Pittsfield, MA 01201

  Beautiful 4 bedroom contemporary on Lilybrook Road. Vaulted entry way leads to living (sitting) room flanked by formal dining room. Also on the first floor is oversized great (family) room with fireplace, large eat-in kitchen and private master (in-law) suite with full bath and jet tub. The second floor has another master suite with full private bath, two additional bedrooms, and a second full

  

  Paul Clark

  CLARK REALTY GROUP LLC

  (413) 327-7998

  10 Lillybrook Rd, Pittsfield, MA 01201
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  /24

  $335,000

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  363 Henderson Rd, Williamstown, MA 01267

  Discover the perfect blend of timeless New England character and modern comfort in this beautifully maintained home. Offering three generous bedrooms plus a flexible office or walk-in closet, the residence also features 1.5 thoughtfully updated bathrooms and abundant natural light throughout.An open, flowing floor plan showcases warm wood flooring and creates an inviting space for

  

  Gary Fuls Jr

  RE/MAX Transitions

  (413) 779-8073

  363 Henderson Rd, Williamstown, MA 01267
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  /10

  $155,000

  • Land
  • 5.24 Acres
  • $29,580 per Acre

  104 Hupi Rd, Monterey, MA 01245

  Ready to build a new custom home with all your personal touches! Views of Lake Garfield. Close to downtown Monterey. Fresh 5 acre parcel to construct a magnificent home in the Berkshires!

  

  Cristian Sanchez

  COHEN & WHITE ASSOCIATES

  (413) 771-4725

  104 Hupi Rd, Monterey, MA 01245
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  /8

  $45,000

  • Land
  • 1.08 Acres
  • $41,666 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 numerous

  

  Diane Thorson

  WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  (413) 343-7322

  Lot 24 Old Farm Ln, Pittsfield, MA 01201
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  /32

  $650,000

  • 5 Beds
  • 4 Baths
  • 2,499 Sq Ft

  73 Christian Hill Rd, Great Barrington, MA 01230

  Investors zoom in on this property, we have an income producing property. 3 of the 4 units are rented and all tenants are all current. The 4th unit is open for one more tenant. Property has been remodeled, we have a new roof with warranty, foundation work to reinforce this property, new floors in all the units, bathrooms are renovated, the entire interior has been repainted, Kitchen remodel, New

  

  Cristian Sanchez

  COHEN & WHITE ASSOCIATES

  (413) 779-9020

  73 Christian Hill Rd, Great Barrington, MA 01230
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  /8

  $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 numerous

  

  Diane Thorson

  WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  (413) 307-3151

  Lot 23 Old Farm Ln, Pittsfield, MA 01201
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  /17

  $495,000

  • 1 Bed
  • 1 Bath
  • 990 Sq Ft

  520 State Rd Unit 303, North Adams, MA 01247

  Loft 303 at Greylock WORKS is a beautifully scaled, south-facing 1BR | 1BA Berkshires residence offering 940SF of refined living, complemented by a rare 50 SF private loggia. Set within the region's most celebrated mill conversion, this luminous third-floor home blends the architectural integrity of the original mill with thoughtful, custom architectural finishes.With nearly 12-foot ceilings and

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 300-6283

  520 State Rd Unit 303, North Adams, MA 01247
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  /8

  $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

  (413) 798-8328

  306 South St, Pittsfield, MA 01201
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  /97

  $349,000

  • 4 Beds
  • 3.5 Baths
  • 4,009 Sq Ft

  514 South St, Pittsfield, MA 01201

  Set along one of Pittsfield's historic corridors, this circa 1815 Federal-style estate offers a compelling study in early American architecture, enduring design, and modern potential. Once a vibrant estate, the property still echoes its past, where landscaping and period lighting brought warmth and presence to the grounds. Inside, a quiet air of English refinement unfolds. Neoclassical detailing

  

  Syrah Bradley

  BISHOP WEST REAL ESTATE

  (413) 722-5807

  514 South St, Pittsfield, MA 01201
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  /46

  $699,900

  • 5 Beds
  • 3.5 Baths
  • 3,074 Sq Ft

  161 Leona Dr, Pittsfield, MA 01201

  Set in one of Southeast Pittsfield's most desirable neighborhoods, this very sunny and impeccably maintained home offers the perfect balance of gracious living, flexible space, and effortless entertaining. Lovingly cared for by its current owner, the home unfolds with elegant formal rooms, hardwood floors, and a warm wood burning fireplace anchoring the living room. The heart of the home is an

  

  Nick Geranios

  WILLIAM PITT SOTHEBY'S - LENOX

  (413) 570-8931

  161 Leona Dr, Pittsfield, MA 01201
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  /7

  $59,900

  • 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

  (413) 288-3713

  Lot 140 Westbrook Terrace, Pittsfield, MA 01201
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  /42

  $1,650,000

  • 4 Beds
  • 3 Baths
  • 7,027 Sq Ft

  17 East St, Stockbridge, MA 01262

  Architecturally iconic and rich with history, this brick Federal home and its gracefully conceived mid-1990s expansion offer a rare opportunity for a buyer with vision. The last major renovation paired the 1830s structure with an addition that respects the original proportions while opening new possibilities for contemporary living. Set along the Stockbridge–Lenox corridor on 13+/- acres (9

  

  Selina Lamb

  Birch Properties

  (413) 300-6860

  17 East St, Stockbridge, MA 01262
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  /16

  $125,000

  • 3 Beds
  • 2 Baths
  • 1,804 Sq Ft

  77 Front St, North Adams, MA 01247

  Centrally located two family. Located a short distance from Downtown North Adams , Mass MoCA and Groundart Studios. The home is currently being used as single family. The second egress to unit 2 will to be restored.The property is a double lot. There is a building lot to the left of the existing home.

  

  Michael Hernandez

  360BERKSHIRE REALTY GROUP

  (413) 296-2006

  77 Front St, North Adams, MA 01247
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  /42

  $1,280,000

  • 3 Beds
  • 4.5 Baths
  • 2,691 Sq Ft

  18 Highcrest Rd Unit 20, Lenox, MA 01240

  

  Selina Lamb

  Birch Properties

  (413) 591-5654

  18 Highcrest Rd Unit 20, Lenox, MA 01240
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  /2

  $150,000

  • Land
  • 0.45 Acre
  • $333,333 per Acre

  50 Commercial St, Adams, MA 01220

  Commercial Parcel located on route 8 in Adams MA. Strong commercial location.

  

  Michael Hernandez

  360BERKSHIRE REALTY GROUP

  (413) 402-6094

  50 Commercial St, Adams, MA 01220
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  /27

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,096 Sq Ft

  33 Gattuso Dr, North Adams, MA 01247

  Nestled in a quiet North Adams neighborhood, this well-maintained single-family ranch offers comfort, convenience, and beautiful mountain views. Built in 1972, the home features 3 bedrooms, 1 full bath, and 1,096 sq. ft. of living space on a spacious 1-acre lot.Enjoy the cozy sunroom with a wood stove, perfect for relaxing year-round, along with the front deck ideal for taking in the peaceful

  

  Michael Hernandez

  360BERKSHIRE REALTY GROUP

  (413) 287-1251

  33 Gattuso Dr, North Adams, MA 01247
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  /23

  $1,340,000

  • 2 Beds
  • 2 Baths
  • 2,110 Sq Ft

  520 State Rd Unit 402, North Adams, MA 01247

  Loft 402 is one of Greylock WORKS' most sought-after residences: a large, south-facing 2BR | 2BA + Study Berkshires loft with soaring 16-foot ceilings, luminous all-day light, and sweeping views of the hills. Set within the region's most celebrated mill conversion, this exceptional home blends architectural authenticity with contemporary design in a way that defines modern Berkshire living.The

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 725-4556

  520 State Rd Unit 402, North Adams, MA 01247
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  /36

  $297,000

  • 4 Beds
  • 2.5 Baths
  • 2,458 Sq Ft

  83 Williams St, North Adams, MA 01247

  Experience the perfect blend of historic charm and contemporary comfort with this beautifully renovated home, ideally situated near Mass MOCA and the vibrant downtown area. Featuring four spacious bedrooms and a versatile first-floor flex room, along with two and a half baths, this residence is designed for modern living. Enjoy peace of mind with numerous updates that include a new roof, upgraded

  

  Gary Fuls Jr

  RE/MAX Transitions

  (413) 884-5511

  83 Williams St, North Adams, MA 01247
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  /53

  $465,000

  • 4 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  165 Sandisfield Rd, Sandisfield, MA 01255

  This home is ready for its new owner. A complete professionally remodeled interior. New Septic System, New insulation, New Windows, New Kitchen and Appliances, Freshly Painted, Fiber Optic Internet available, New gravel Driveway, New Boiler, New hot water heater, Brand new LED lighting within the entire home. New tile work in the the 2 full baths. Laundry conveniently located on the same level as

  

  Cristian Sanchez

  COHEN & WHITE ASSOCIATES

  (413) 392-4615

  165 Sandisfield Rd, Sandisfield, MA 01255
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  /7

  $79,900

  • 2 Beds
  • 1 Bath
  • 550 Sq Ft

  3 Jennifer Ln, West Stockbridge, MA 01266

  Nicely remodeled 2 bedroom trailer with fireplace and 2 baths. Park rent is $399.56 per month.

  

  John Ciepiela

  BISHOP WEST REAL ESTATE

  (413) 741-1606

  3 Jennifer Ln, West Stockbridge, MA 01266
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  /39

  $325,000

  • 12 Beds
  • 1 Bath
  • 4,215 Sq Ft

  292 West St, Pittsfield, MA 01201

  This large residential property offers exceptional income potential in a strong Pittsfield rental market. With 12 bedrooms and 3.5 bathrooms, it supports high-capacity occupancy and steady cash flow. The full basement provides extensive storage and includes areas where two former bathrooms once existed, offering a foundation for future updates. A full standing attic adds valuable expansion

  

  Gary Fuls Jr

  RE/MAX Transitions

  (413) 884-5511

  292 West St, Pittsfield, MA 01201
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  /32

  $200,000

  • 8 Beds
  • 4 Baths
  • 5,142 Sq Ft

  32-38 Spring St, North Adams, MA 01247

  This is a four-family property. Property is VACANT. Seller is conveying lot 56-A & Lot 56-B Updated mechanicals ready for the next owner to complete. Each unit has 2 bedrooms, 1 bathroom, and a bigger living room space with windows that allow lots of natural light to shine through. The kitchen is a moderate size giving enough area for people to maneuver. The property is located close to schools,

  

  Michael Hernandez

  360BERKSHIRE REALTY GROUP

  (413) 966-0983

  32-38 Spring St, North Adams, MA 01247
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  /4

  $215,000

  • Land
  • 14.37 Acres
  • $14,962 per Acre

  0 Reservoir Rd Unit 16, North Adams, MA 01247

  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

  RE/MAX Transitions

  (413) 779-8432

  0 Reservoir Rd Unit 16, North Adams, MA 01247
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  /19

  $610,000

  • 1 Bed
  • 1.5 Baths
  • 1,150 Sq Ft

  520 State Rd Unit 208, North Adams, MA 01247

  Loft 208 at Greylock WORKS is a beautifully proportioned 1BR | 1.5BA + Study Berkshires residence set within the region's most celebrated mill conversion, offering 1,150 SF of refined, light-filled living. With 12.5-foot ceilings, expansive volume, and an elegant L-shaped living and dining area, the home blends the character of the original mill with elevated contemporary detailing to create a

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 798-5680

  520 State Rd Unit 208, North Adams, MA 01247
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  /42

  $319,900

  • 3 Beds
  • 2 Baths
  • 1,646 Sq Ft

  1044 Beaver Pond Meadows, Hancock, MA 01237

  Discover this Berkshires getaway in the private Beaver Pond Meadows community, complete with clubhouse and pool access! Just minutes from Jiminy Peak, this location offers a quieter, more relaxed alternative to Country Village. This fully furnished townhouse boasts a strong rental history and plenty of space to spread out, featuring three bedrooms and a full bath on the first level, a spacious

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (855) 810-0060

  1044 Beaver Pond Meadows, Hancock, MA 01237
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  /43

  $445,000

  • 2 Beds
  • 3 Baths
  • 1,814 Sq Ft

  35 Chapman Rd, Pittsfield, MA 01201

  Classic New England farmhouse featuring a charming kitchen with beautiful Berkshire views and an open, inviting layout perfect for entertaining. The 1st floor offers, full bath and convenient laundry hookups, along with 2 living rooms. One ideal for relaxation and the other a perfect home office, playroom, game room. Upstairs, you'll find 2 good sized bedrooms each with their own full bathroom

  

  Laura Arseneau

  PAULA MCLEAN REALTORS INC.

  (413) 323-3512

  35 Chapman Rd, Pittsfield, MA 01201
• 

  /2

  $320,000

  • 6 Beds
  • 4 Baths
  • 3,912 Sq Ft

  40 Henry Ave, Pittsfield, MA 01201

  THIS LISTING TO BE SOLD AS PART OF A 11 UNIT PACKAGE: Other properties included are located at 27-31 Pleasant St. Pittsfield, MA 01201 and 101-103 Lincoln St. Pittsfield, MA 01201. Acquire three multifamily package offered at $920,000. Income & expense and rent roll document available in documents and or upon request.

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 339-3453

  40 Henry Ave, Pittsfield, MA 01201
• 

  

  /7

  $59,900

  • 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

  (413) 414-5864

  Lot 144 Eastbrook Ln, Pittsfield, MA 01201
• 

  

  /42

  $2,649,000

  • 6 Beds
  • 6.5 Baths
  • 6,225 Sq Ft

  250 West St, Lenox, MA 01240

  Seconds—not minutes—from Tanglewood’s main gate, this reimagined contemporary estate in Lenox is tucked into a sunlit woodland setting offering rare privacy and unrivaled proximity. Originally built in 2017 and completely updated in 2020, the home features soaring ceilings, rich mahogany and cherry finishes, a chef’s kitchen, and multiple entertaining spaces. The ground-floor primary suite is

  

  Selina Lamb

  Birch Properties

  (413) 423-1264

  250 West St, Lenox, MA 01240
• 

  

  /11

  $839,900

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  407 Churchill St, Pittsfield, MA 01201

  To Be Built Home - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 3.59-acre lot (MLS # 248344), installed

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 475-9767

  407 Churchill St, Pittsfield, MA 01201

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