Berkshire County MA Homes for Sale

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  $3,000

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  14 Richardson St Unit 14, Cheshire, MA 01225

  Welcome to 14 Richardson Street, Cheshire, MA, a beautifully maintained fully furnished long-term rental offering approximately 1,800 square feet of thoughtfully designed living space. Built in 2006, this spacious 3-bedroom, 2.5-bath home comes fully furnished, including furniture, cookware, dishes, silverware, towels, linens, and other household essentials.Designed with ADA accessibility in

  Christian Garner NOCHER REALTY

  14 Richardson St Unit 14, Cheshire, MA 01225
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  $3,495,000

  • 5 Beds
  • 4.5 Baths
  • 3,862 Sq Ft

  16 Old Tree Farm Rd, Stockbridge, MA 01262

  Set on six picturesque acres in Stockbridge, this beautiful contemporary home offers privacy, comfort and stunning views. The thoughtfully designed layout features five bedrooms and 4.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The chef's kitchen is equipped with premium Wolf and Sub-Zero appliances, perfect for entertaining or everyday living. An

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  16 Old Tree Farm Rd, Stockbridge, MA 01262
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  $395,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,584 Sq Ft

  335 North St, Cheshire, MA 01225

  Modern ranch home perched high above North Street offering views to the east and bordering the approximate 370,000 acre Appalachian trail on two sides! Enjoy direct access for hiking right off your property! Offering 3 bedrooms, 3 full baths and extremely nice mechanicals updated in recent years. The lower level consists of a one bay garage/storage area and a beautiful in-law accommodations. The

  Jeffrey Loholdt ENGEL & VOLKERS WELLESLEY

  335 North St, Cheshire, MA 01225
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  $529,900

  • 3 Beds
  • 2 Baths
  • 3,542 Sq Ft

  191 Fox Rd, Dalton, MA 01226

  Escape to your own Berkshire retreat at 191 Fox Rd, where 7.5 private acres create the perfect blend of peaceful country living and everyday convenience. Surrounded by nature yet only minutes from shopping, dining, schools, and recreation, this property offers the best of both worlds. Thoughtful upgrades include owned solar, upgraded electrical, efficient heating and air conditioning, a backup

  Anthony Riello Lamacchia Realty, Inc. - Dalton

  191 Fox Rd, Dalton, MA 01226
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  $525,000

  $14K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,497 Sq Ft

  32 Summer St, Adams, MA 01220

  Timeless elegance meets modern luxury in this beautifully maintained Victorian home, where historic charm and exceptional craftsmanship shine throughout. Lovingly cared for and thoughtfully updated, this stunning residence showcases exquisite architectural details, original character, and an abundance of natural light. High-end finishes are found at every turn, including a beautifully appointed

  Sean Taylor MORESI REAL ESTATE PARTNERS

  32 Summer St, Adams, MA 01220
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  /8

  $1,850,000

  • 15 Beds
  • 15 Baths
  • 18,329 Sq Ft

  68 Union St, Pittsfield, MA 01201

  68-80 Union Street presents a rare opportunity to acquire a stabilized, fully renovated 15-unit multifamily property in the heart of Pittsfield, Massachusetts. The property delivers strong in-place cash flow at a 7.52 cap rate with meaningful embedded upside through below-market rents and two ready-to-lease vacant units. Every unit has been comprehensively renovated: kitchens include new

  Cole Ungar SKYTOP ASSET MANAGEMENT

  68 Union St, Pittsfield, MA 01201
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  $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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  $998,700

  $251K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,072 Sq Ft

  87 Old Orebed Rd, Lanesborough, MA 01237

  Dreaming of your own private sanctuary? 30+ acres await exploration! Enter between two stone pillars and the long winding driveway will take you past woodland glades, open spaces, mature tree stands, manicured lawns and a magnificent spring-fed swimming quarry! Acres of open cleared land afford additional usage options. Cedar log home, one-owner custom built. Large wrap-around deck and long

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  87 Old Orebed Rd, Lanesborough, MA 01237
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  $995,000

  $205K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,328 Sq Ft

  3 Pleasant View Dr, Great Barrington, MA 01230

  Rare offering of over six acres ''On the Hill'', sprawling residence with first floor primary, large eat-in kitchen with cozy fireplace.. porch-privacy-garage..open acreage bordered by woods.. walking distance to Main Street, Skiing and Lake Mansfield nearby...Five bedrooms, three baths. Formal living room.Plenty of room for expansion.

  Martha Piper THE KINDERHOOK GROUP

  3 Pleasant View Dr, Great Barrington, MA 01230
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  $3,850,000

  • 4 Beds
  • 3.5 Baths
  • 4,292 Sq Ft

  74 Seekonk Cross Rd, Great Barrington, MA 01230

  SUN DRENCHED MODERN HOME WITH POOL AND PRIVACY, A SHORT WALK TO THE WALDORF SCHOOL AND THE GREEN RIVER. This gorgeous property consists of 2 separate building lots and is on a lovely, quiet road ideal for walking and biking, and only 7 minutes drive to Guido's. The house, which has been recently completely reimagined and added onto, is an ode to sophistication, beauty, and practicality.4+

  Robin Ban COMPASS MASSACHUSETTS , LLC GB

  74 Seekonk Cross Rd, Great Barrington, MA 01230
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  $210,000

  $15K PRICE DROP

  • Land
  • 9.7 Acres
  • $21,649 per Acre

  487 Jenks Rd, Cheshire, MA 01225

  Build your dream home on this exceptional 9.7 acre parcel, already prepared for your vision! This beautiful property features a completed septic system, drilled well, 100-amp electrical service, and a 10' x 20' storage shed-saving you time and expense. With much of the groundwork already completed, this lot is ready for construction. Enjoy the privacy and space of nearly 10 acres while still

  Darcy Reid MOCKINGBIRD REAL ESTATE

  487 Jenks Rd, Cheshire, MA 01225
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  $499,900

  $30K PRICE DROP

  • 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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  $395,000

  • 3 Beds
  • 2 Baths
  • 1,081 Sq Ft

  472 & 0 Upper E Hoosac St, Adams, MA 01220

  Impeccably kept Ranch home including additional wooded lot on a quiet paved road less traveled bordering state lands. Nicely finished, open and light filled kitchen, dining and living room boasting long range views of our states highest peak, Mount Greylock. No better way to watch the color pallets of the Berkshires than from the expansive deck overlooking the sprawling yard and distant views.

  Jeffrey Loholdt ENGEL & VOLKERS WELLESLEY

  472 & 0 Upper E Hoosac St, Adams, MA 01220
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  $70,014

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  14 Alice Dr, Hinsdale, MA 01235

  Discover peaceful living in this 2 bed, 2 bath mobile home, tucked away as the last unit at the end of the street. Enjoy the privacy and quiet that comes with having no through traffic and a serene setting.This owner-occupied home has a lot rent of $430./month. Pets are welcome with a license, making it the perfect spot. Affordable, private, comfortable, a wonderful place to call home. Needs

  Barbara Osborne ASHMERE REALTY, INC.

  14 Alice Dr, Hinsdale, MA 01235
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  $249,900

  $40K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 875 Sq Ft

  832 East St, Lee, MA 01238

  Welcome home to this sweet and petite one level easy living ranch style home. Sun filled bright spaces invite you to relax and enjoy the end of each day in this thoughtfully planned layout. Boasting a king size bedroom, two other bedrooms, and an updated full bath. The galley style kitchen is comfortable for baking and creating all the dinner gatherings you wish. Comfortable everyday dining is

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  832 East St, Lee, MA 01238
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  $350,000

  $13K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,624 Sq Ft

  75 Housatonic St, Lee, MA 01238

  Charming and full of character, this in town Lee home blends timeless original details with thoughtful modern updates. Beautiful hardwood floors, original woodwork, and classic architectural features create warmth throughout. The spacious layout offers comfortable living with abundant natural light and inviting spaces for everyday life or entertaining. A Tesla charger adds modern convenience,

  Katie Soules WILLIAM RAVEIS - BERKSHIRE

  75 Housatonic St, Lee, MA 01238
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  $334,900

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,088 Sq Ft

  112 Gamwell Ave, Pittsfield, MA 01201

  First time ever offered! Single Level Living Surrounded by Gardens You'll Fall in Love With Lovingly maintained by the original builder's family, this cherished ranch is ready for it's next chapter. Recently refinished hardwood floors, a fireplace, and a sun filled four season room with French doors overlooking established perennial gardens create a warm and inviting atmosphere. Years of

  Stacy Hebb NOCHER REALTY

  112 Gamwell Ave, Pittsfield, MA 01201
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  $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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  /20

  $195,000

  $16K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,236 Sq Ft

  8 Fuller St, North Adams, MA 01247

  Welcome home to this inviting 3-bedroom, 1.5-bath property offering a blend of character and convenience. Tall ceilings and an open living and dining room create a bright, welcoming space that's perfect for everyday living and entertaining. First-floor laundry adds convenience, while the rare off-street parking is a valuable bonus. Relax on the front or back porch and enjoy the charming

  Amanda Kmetz ROBERTS & ASSOC. REALTY, INC

  8 Fuller St, North Adams, MA 01247
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  /8

  $1,250

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft

  33 N Main Rd Unit STUDIO APT, Otis, MA 01253

  Quaint Studio Barn Apartment located in the center of Otis. Nicely furnished and move-in ready. LONG-TERM LEASE PREFERRED.

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  33 N Main Rd Unit STUDIO APT, Otis, MA 01253
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  $724,900

  $25K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,744 Sq Ft

  255 High St Hill Rd, Windsor, MA 01270

  Tucked away on 3.24 private wooded acres, this one-of-a-kind Contemporary offers 3,744 sq. ft. of living space across three finished levels. Soaring ceilings, exposed timber beams, hardwood floors, and a dramatic center chimney create a warm yet impressive setting. The open floor plan is anchored by multiple wood-burning fireplaces, a pellet stove, and abundant natural light. Offering a total of

  Jesse Dimitropolis RE/MAX COMPASS

  255 High St Hill Rd, Windsor, MA 01270
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  /15

  $39,500

  • Land
  • 2.12 Acres
  • $18,632 per Acre

  21 Stoney Brook, Becket, MA 01223

  Discover the perfect setting for your future home on this beautiful, level building lot located on Stoney Brook Road. Nestled among attractive, established homes, this property offers a peaceful and private setting while still providing convenient access to all that the Berkshires have to offer. Reasonable HOA covenants help protect the character and value of the neighborhood. Located just

  Tanya Shepardson Lamacchia Realty, Inc. - Dalton

  21 Stoney Brook, Becket, MA 01223
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  /31

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,081 Sq Ft

  472 & 0 E Hoosac St, Adams, MA 01220

  Modern Ranch Home with additional wooded lot and breathtaking views bordering vast State Lands!Impeccably kept Ranch home including additional wooded lot on a quiet paved road less traveled bordering state lands. Nicely finished, open and light filled kitchen, dining and living room boasting long range views of our states highest peak, Mount Greylock. No better way to watch the color pallets of

  Jeffrey Loholdt Engel & Völkers Wellesley

  472 & 0 E Hoosac St, Adams, MA 01220
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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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  /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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  $329,000

  • 4 Beds
  • 3 Baths
  • 1,575 Sq Ft

  28 Adelaide Ave, Pittsfield, MA 01201

  Welcome to this charming four-bedroom, three-bath home nestled in a desirable Southeast Pittsfield neighborhood. Lovingly maintained and well insulated through the years, this home offers a warm and inviting atmosphere with a wonderful blend of original character and everyday comfort.Inside, you'll find hardwood flooring, spacious bedrooms, two first-floor bedrooms and 2 full bathroom, and an

  Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

  28 Adelaide Ave, Pittsfield, MA 01201
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  $649,900

  • 2 Beds
  • 3 Baths
  • 2,481 Sq Ft

  40 Willow Cove Rd, Cheshire, MA 01225

  Nestled on a picturesque 2 acre lot and set well back from the road for added privacy, this beautiful 2 bedroom, 2 bath home offers both comfort, character and outdoor living. Step inside to a sunken livingroom centered around a stunning fieldstone fireplace. A large den offers flexible living space, and the finished lower level features a bedroom and full bath. French doors lead to an

  Robin Moore 413 REAL ESTATE

  40 Willow Cove Rd, Cheshire, MA 01225
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  $570,000

  $20K PRICE DROP

  • 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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  $540,000

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,406 Sq Ft

  2 Melrose St, Adams, MA 01220

  Welcome to the historic Simmons Cottage located at 2 Melrose Street in Adams, MA. This Victorian gem, completed in 1901, perfectly blends its 19th-century character with modern convenience. Situated on a .24-acre lot in the heart of Adams, the 2,406-square-foot residence features 4 bedrooms, three bathrooms, office, and full attic.The home's historic elegance shines through its preserved

  

  Diane Thorson

  WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  2 Melrose St, Adams, MA 01220
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  $535,000

  $60K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,043 Sq Ft

  500 Creamery Rd, Hinsdale, MA 01235

  This impeccably maintained contemporary home is sited on four acres of manicured grounds, bordered by Massachusetts Fish and Game conservation lands. Nestled within a portion of the 4,500 +/- protected acres in Hinsdale, the setting provides a private and serene natural backdrop with easy access to recreation at the nearby 287-acre Ashmere Lake, located just 1.6 miles away. Inside, the home we

  Jeffrey Loholdt ENGEL & VOLKERS WELLESLEY

  500 Creamery Rd, Hinsdale, MA 01235
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  $799,000

  $126K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,155 Sq Ft

  19 Sackman Way, Monterey, MA 01245

  Private Lake Buel access is just steps from this exceptional one-level, 4-bedroom, 3-bath ranch--your perfect year-round getaway or full-time retreat. Inside, you'll find a striking two-sided fieldstone fireplace anchoring the living and dining areas, complemented by warm wood floors that add timeless charm. Step outside to a spacious back deck overlooking your own private bird sanctuary--an

  Rosemary Baumann HOUSATONIC REAL ESTATE

  19 Sackman Way, Monterey, MA 01245
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  $160,000

  $5K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,961 Sq Ft

  842 Church St, North Adams, MA 01247

  Bring this charming 1800s farmhouse back to life! Offering nearly 3,000 square feet of living space, this property is packed with potential for investors, contractors, or buyers looking for their next renovation project. Previously configured with an in-law apartment, it may offer the opportunity to convert to a two-family home with the proper permits and approvals. With its generous footprint

  Michele Purcell Lamacchia Realty, Inc.

  842 Church St, North Adams, MA 01247
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  $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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  $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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  $380,000

  • Land
  • 15 Acres
  • $25,333 per Acre

  365 Churchill St, Pittsfield, MA 01201

  Discover the ideal setting for your next home or retreat on this 15-acre parcel in West Pittsfield. Thoughtfully prepared, the property already features installed electricity, along with a newly constructed driveway and building pad. Enjoy a perfect blend of open and wooded land, including 5+ acres of fields, 10 acres of forest, and approximately 700 feet of road frontage. With city water,

  Sarah Carr Key Realty

  365 Churchill St, Pittsfield, MA 01201
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  $575,000

  $150K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,809 Sq Ft

  29 Grove Ave, Lanesborough, MA 01237

  Enjoy lakefront living in this charming 3-bedroom, 1-bath home offering beautiful water views and comfortable indoor-outdoor living. The inviting living room features a cozy fireplace and sliding glass doors that open to a spacious deck, complete with a 3 season sunroom--perfect for enjoying peaceful mornings overlooking the lake.The updated kitchen with new appliances provide modern convenience.

  Robin Moore 413 REAL ESTATE

  29 Grove Ave, Lanesborough, MA 01237
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  $850,000

  $49K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  1641 North St, Pittsfield, MA 01201

  Wake up to breathtaking panoramic waterfront views & end every day with spectacular sunsets from this exceptional ranch offering approx. 170' of waterfront frontage.This well-maintained home features 3 bedrooms, 2 full baths & an inviting open layout designed to showcase the stunning scenery.The sunroom, with walls of glass sliders, opens to an expansive deck-perfect for entertaining, relaxing or

  Darcy Reid MOCKINGBIRD REAL ESTATE

  1641 North 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
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  $370,000

  $15K PRICE DROP

  • 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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  /34

  $558,000

  $21K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,953 Sq Ft

  50 Mountain View Terrace, Lee, MA 01238

  OPEN HOUSE: SAT, AUG 22ND 11AM-12:30PMIdeally located in desirable street in Lee, this well-maintained Cape blends classic charm with thoughtful modern updates. Surrounded by beautiful landscaping, the home features 4 bedrooms and 2 full baths, including 2 bedrooms and a full bath on the first floor for convenient one-level living. The updated 2022 kitchen offers granite countertops, modern

  Judi Panzano HOUSATONIC REAL ESTATE

  50 Mountain View Terrace, Lee, MA 01238

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