Pittsfield, MA Houses for Sale

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  /25

  $180,000

  • 2 Beds
  • 1.5 Baths
  • 1,184 Sq Ft

  94 John St, Pittsfield, MA 01201

  BRING ME AN OFFER. Turnkey Former Airbnb-Fully Updated & Move-in Ready! This beautifully renovated 2-bed, 1.5 bath home is perfect for personal residence or income-generating property. Previously a successful Airbnb. it's packed with charm, upgrades, & flexible living space. Enjoy a spacious eat-in kitchen with new cabinets, countertop, & flooring. Opens up to the family room for easy

  Barbara DeMers NOCHER REALTY

  94 John St, Pittsfield, MA 01201
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• 

  

  

  /35

  $725,000

  • 4 Beds
  • 3.5 Baths
  • 3,491 Sq Ft

  26 Filomena Dr, Pittsfield, MA 01201

  This lovely Colonial home is nestled at the end of the road adjoining Kirvin Park w/ great curb appeal. .The main floor has 2,488 sq.ft. w/ an attached double garage, a mudroom w/ laundry facilities, a large combined kitchen & family room leading to an outdoor deck. Also a spacious dining room & living room & a half bath off the front foyer.. Upstairs: 1,546 sq. ft, w/ a large en-suite primary

  Barbara K Greenfeld SIGNATURE ASSOCIATES

  26 Filomena Dr, Pittsfield, MA 01201
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  /12

  $189,900

  • 2 Beds
  • 1,002 Sq Ft

  105 Crane Ave, Pittsfield, MA 01201

  This Ranch is a fixer-upper sitting on almost a half acre! There is great parking space plus a detached garage and a fenced-in backyard. New roof done kn the last couple years.Desirable location, near Berkshire Hills Country club and walking distance to the golf course, and just a few minutes drive to BMC Hospital and to Pontoosuc lake. The home has vinyl siding and City water and sewer.Great

  Maria Liccardi LAMACCHIA REALTY, INC

  105 Crane Ave, Pittsfield, MA 01201
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  /66

  $2,250,000

  • 5 Beds
  • 6 Baths
  • 5,477 Sq Ft

  1030 West St, Pittsfield, MA 01201

  1030 West is a bespoke family compound on 6 acres between Onota Lake and Pittsfield State Forest, offering refined country living with city convenience. The historic main house, decorated by designer Heidi Caillier and featured in her book Memories of Home, has been thoughtfully renovated with timeless materials - custom cabinetry, marble, limestone, Waterworks fixtures, designer and vintage

  Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

  1030 West St, Pittsfield, MA 01201
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  /23

  $239,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  85 Wilson St, Pittsfield, MA 01201

  Single Level Living! This charming 3-bedroom, 1-bath ranch offers comfort, convenience, and recent upgrades throughout. Remodeled in 2017 enjoy central A/C, granite countertops, and a spacious walkout basement. Thoughtful improvements include new 200amp electrical, solar panels (2020) and a new sewer line (2021). Ideally located just minutes from Pontoosuc Lake, Onota Lake, Springside Park, and

  Molly Gillon COMPASS MASSACHUSETTS , LLC GB

  85 Wilson St, Pittsfield, MA 01201
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  /39

  $565,900

  • 8 Beds
  • 3 Baths
  • 4,034 Sq Ft

  144 Bromback St, Pittsfield, MA 01201

  Beautiful, spacious 8 bedroom, 3 updated bath, 4000 sq ft home, custom built and nestled between 2 lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota lake in approximately 10 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, swimming, picnicking and more. Enjoy the convenience of two laundry rooms and two updated

  Janet Benoit Janet L. Benoit

  144 Bromback St, Pittsfield, MA 01201
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  /47

  $449,900

  • 4 Beds
  • 1.5 Baths
  • 2,126 Sq Ft

  31 Lexington Pkwy, Pittsfield, MA 01201

  Welcome to this Southeast Sweetheart -- a charming Dutch Colonial with a full-length front porch perfect for relaxing or socializing. Inside, a gracious entry leads to a classic living room with built-in bookcases, window seats, and a bow window. Recent updates include a new roof, freshly painted exterior, and energy-efficient mini-splits for comfortable cooling and heating, new electrical and

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  31 Lexington Pkwy, Pittsfield, MA 01201
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  /27

  $255,000

  • 3 Beds
  • 1 Bath
  • 888 Sq Ft

  157 Maple Grove Dr, Pittsfield, MA 01201

  Welcome to easy, one-level living in this 3-bedroom ranch, nestled in the sought-after southeast section of Pittsfield. The property features vinyl siding, modern appliances, and on-demand hot water. Outside you will find a fully fenced-in yard ideal for relaxing or entertaining. Enjoy summer days on the expansive deck or take a dip in the above-ground pool. Two storage sheds provide space for

  Jessica Rizzo LAMACCHIA REALTY, INC

  157 Maple Grove Dr, Pittsfield, MA 01201
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  /39

  $269,900

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  11 Oriole St, Pittsfield, MA 01201

  This bright and inviting 1,300 sq ft home offers comfortable living with thoughtful features throughout. Situated on a spacious corner lot, the property boasts two full bathrooms, a partially finished lower level perfect for office, or guest space, and an attached garage for added convenience. Upstairs, bonus finished attic area provides additional storage. The large yard offers room to relax,

  Robin Moore 413 REAL ESTATE

  11 Oriole St, Pittsfield, MA 01201
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  /33

  $525,000 Open Sun 12PM - 3PM

  • 3 Beds
  • 3 Baths
  • 2,351 Sq Ft

  499 Tamarack Rd, Pittsfield, MA 01201

  CHECK OUT THE NEW PHOTOS!!!! Located next to Bousquet, just up the road from the Pittsfield airport, minutes from Lenox and Tanglewood and easy access to all the Berkshires have to offer! Lot's of love and care has gone into this home and property. Beautifully maintained and manicured lawn, private backyard, renovated deck with hot tub and a recently paved driveway are just a few of the outdoor

  Allen Halstead Berkshire Hathaway Home Services Blake

  499 Tamarack Rd, Pittsfield, MA 01201
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  /53

  $995,000

  • 6 Beds
  • 6 Baths
  • 5,198 Sq Ft

  68 Colt Rd, Pittsfield, MA 01201

  Nestled in a charming historic southeast Pittsfield neighborhood, this 4+ bedroom, 5+ bath gem was brought to life in 1914 by the talented architects Harding and Seaver. Their impressive portfolio features notable landmarks like the Berkshire Museum and Lenox Town Hall, showcasing their remarkable contribution to the area's rich history.This grand, yet comfortable home spans four inviting levels!

  Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX

  68 Colt Rd, Pittsfield, MA 01201
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  /45

  $289,900

  • 3 Beds
  • 1 Bath
  • 1,158 Sq Ft

  44 Jason St, Pittsfield, MA 01201

  This delightful 3-bedroom Cape-style home offers serene and comfortable living. Situated on a large lot this home boasts southwesterly mountain views. Designed for convenience, this home features all essential living spaces on a single level. Wood burning fireplace in the living room. A large attic space presents an opportunity for future expansion, whether as a home office, studio, or

  Derek Strzepa NOCHER REALTY

  44 Jason St, Pittsfield, MA 01201
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  /24

  $329,900

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  171 Harryel St, Pittsfield, MA 01201

  Welcome to 171 Harryel St in Pittsfield, MA! This well-maintained 3-bedroom, 1-bath home offers a spacious living area, hardwood floors, and a bright eat-in kitchen. Basement boasts a finished room perfect for entertainingly. Enjoy the private backyard--great for outdoor activities or relaxing. Located on a quiet street with convenient access to parks, shops, and downtown amenities. A great

  John Ciepiela BISHOP WEST REAL ESTATE

  171 Harryel St, Pittsfield, MA 01201
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  /30

  $334,500

  • 3 Beds
  • 2 Baths
  • 1,462 Sq Ft

  48 Preston Ave, Pittsfield, MA 01201

  Adorable cape style home on a quiet street. Gorgeous new kitchen and first floor bath. Wood floors throughout the first floor. The second floor offers more space to include a third bedroom and another full bathroom. Solar panels offer substantial reductions in your electric bill. Please note there are Ring cameras both outside and inside the home.

  Tanya Shepardson Lamacchia Realty, Inc.

  48 Preston Ave, Pittsfield, MA 01201
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  /30

  $339,900

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  185 Lenox Ave, Pittsfield, MA 01201

  OPEN HOUSE Sat 05/31/25 10:00am - 11:30am. Welcome home to this immaculate and beautifully maintained 3-bedroom, 1.5-bath Colonial, located less than one mile from Berkshire Medical Center. This move-in ready gem offers a perfect blend of classic charm and modern updates throughout. Step inside through the inviting tiled foyer and discover a spacious layout featuring hardwood floors and a large

  Cindy Carrigan LAMACCHIA REALTY, INC

  185 Lenox Ave, Pittsfield, MA 01201
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  /55

  $5,499,500

  • 8 Beds
  • 6.5 Baths
  • 6,986 Sq Ft

  140 Hancock Rd, Pittsfield, MA 01201

  Welcome to an extraordinary opportunity on the shores of Pontoosuc Lake. This remarkable estate sets a new standard for lakefront living in Pittsfield and beyond, offering a rare combination of luxury, scale, and setting.With over 18,700 square feet of total space, including an impressive amount of garage space suitable for car collectors or hobbyists, this home provides room to live, relax, and

  Cameron Volastro STONE HOUSE PROPERTIES, LLC

  140 Hancock Rd, Pittsfield, MA 01201
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  /20

  $214,900

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

  232 First St, Pittsfield, MA 01201

  Welcome to a unique property on the edge of Pittsfield's Downtown Creative District. This old-world colonial has been used as office space for the last 20+ years. 6 office spaces with a waiting area, a first floor 1/2 bath and a bonus room that could be converted to a break room or another office space. A nice L shaped wood porch with a handicap ramp. Detached 4 bay garage. The property has

  Anthony Riello LAMACCHIA REALTY, INC

  232 First St, Pittsfield, MA 01201
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  /41

  $965,000

  • 3 Beds
  • 3 Baths
  • 4,024 Sq Ft

  19 Aspen Way, Pittsfield, MA 01201

  Live the lifestyle you deserve in this stunning 4-year-young detached single family condominium offering over 4,000 square feet of luxury! This 3-bed, 3-bath home features a gourmet kitchen with quartz counters, custom cooktop and hood and double ovens. Perfect for the Chef of the family. The home gym with sauna, and a spacious walkout lower level with game room and bar is the perfect space for

  Victoria Standring LAMACCHIA REALTY, INC

  19 Aspen Way, Pittsfield, MA 01201
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  /53

  $289,000

  • 4 Beds
  • 2 Baths
  • 1,886 Sq Ft

  95 Oak Hill Rd, Pittsfield, MA 01201

  VERY MOTIVATED SELLER! Peace and quiet of country living and being just minutes from everything you need! This lovely home is in a desirable neighborhood, convenient to shopping, yummy restaurants, and local businesses. Plus, getting around is a breeze with easy access to routes 7, 9, and 8. Step inside and you'll find a cozy and inviting space with beautiful hardwood floors throughout. With 8

  Mark Harris SIGNATURE ASSOCIATES

  95 Oak Hill Rd, Pittsfield, MA 01201
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  /37

  $689,000

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  29 Chestnut Rd, Pittsfield, MA 01201

  Brand-New Contemporary Cape Near Richmond Pond - Move-In Ready!Be the first to live in this stunning new construction Cape, just completed & ready for immediate occupancy with a Certificate of Occupancy in hand. Designed with modern living in mind, the main level features insulated tile floors & a stylish open-concept kitchen, dining, & living area that opens to a private patio with a built-in

  Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  29 Chestnut Rd, Pittsfield, MA 01201
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  /46

  $539,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 2,145 Sq Ft

  121 Wendell Ave, Pittsfield, MA 01201

  Architecturally significant and beautifully renovated, this stunning 3 bed, 2.5 bath brick home sits on a prominent corner lot in a coveted residential enclave of stately homes--just a short stroll to downtown. Thoughtful updates blend seamlessly with original character, offering timeless elegance, modern comfort, and exceptional natural light throughout. Featuring a dramatic staircase, hardwood

  Victoria Standring LAMACCHIA REALTY, INC

  121 Wendell Ave, Pittsfield, MA 01201
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  /44

  $539,000

  • 5 Beds
  • 2.5 Baths
  • 2,994 Sq Ft

  100 Holmes Rd, Pittsfield, MA 01201

  Classic elegance meets modern living in this stately Colonial set on a large corner lot in a highly desired neighborhood, with circular driveway for easy in and out access. Gracious entry, hardwood floors, an updated eat in kitchen plus a formal dining room with original leaded glass hutch and a formal living room. The stunning great room addition, with separate entrance and access to deck and

  Victoria Standring LAMACCHIA REALTY, INC

  100 Holmes Rd, Pittsfield, MA 01201
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  /35

  $475,500

  • 4 Beds
  • 2.5 Baths
  • 2,140 Sq Ft

  149 Kittredge Rd, Pittsfield, MA 01201

  Beautifully renovated home with plenty of space for everyone. This home offers 4 bedrooms, 2.5 baths, and a huge yard. Fully finished walkout basement adds another living room, 1⁄2 bath, and 4th bedroom.

  Tanya Shepardson Lamacchia Realty, Inc.

  149 Kittredge Rd, Pittsfield, MA 01201
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  /49

  $795,000

  • 5 Beds
  • 2.5 Baths
  • 4,078 Sq Ft

  40 Commonwealth Ave, Pittsfield, MA 01201

  Immaculately restored antique Colonial dripping with charm offering modern conveniences. Chef's kitchen with Quartz counters, glass back splash, beautiful cabinets, and double sized Wolf Range. Entertaining is made easy with a large dining area, grand fire-placed living room with floor to ceiling windows overlooking the private and lush green lawn. Glorious master suite with new spa like bath.

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  40 Commonwealth Ave, Pittsfield, MA 01201
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  /5

  $179,900

  • 6 Beds
  • 2 Baths
  • 2,376 Sq Ft

  24 Glenwood Ave, Pittsfield, MA 01201

  For sale an approximately 2,376 SF two-family home with a 2-car garage on approximately 0.227 acres of land. The Property is located in close proximity to the center of Pittsfield with easy access to Rts. 7, 8, 8A, 9 & 20.

  John Dill Colebrook Realty Services, Inc.

  24 Glenwood Ave, Pittsfield, MA 01201
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  /82

  $595,000

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

  35 Chapman Rd, Pittsfield, MA 01201

  9+ ACRES of ''country living'' at its best, with beautiful mountain views! This property features a renovated farmhouse, 2 car garage, 1 outbuilding and Barn. It's only a few hundred feet from the Lenox town line, where Chapman Rd turns into East St. Pittsfield-Lenox Rd (Rt 20) is just around the corner. To be honest, I'm not going to overwhelm you with a lot of descriptions of what the

  Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  35 Chapman Rd, Pittsfield, MA 01201
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  /47

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 2,104 Sq Ft

  18 Lacona St, Pittsfield, MA 01201

  Step in to the inviting foyer in this brand new colonial featuring beautiful kitchen dining open floor plan, first floor laundry, 3 spacious bedrooms and two full baths on second floor, sliders from dining room out to deck, 2 car garage EV car ready, large basement plumbed for 4th bath and sliders to nice yard all located walking distance to Pontoosuc lake and park. Come make this your new

  Robin Moore 413 REAL ESTATE

  18 Lacona St, Pittsfield, MA 01201
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  /81

  $1,195,000

  • 5 Beds
  • 2.5 Baths
  • 3,087 Sq Ft

  18 Old Farm Ln, Pittsfield, MA 01201

  Newly Constructed Farmhouse Style Home in coveted Woodmonte Estates central to all Berkshire attractions. Over the bridge into the woods escape to a magical setting amidst a woodland preserve of 2+ acres. Build a family compound of your own with 1 extra homesites to create your dreams with incredible peace and privacy yet all city conveniences. Unique living to mingle in a community with

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  18 Old Farm Ln, Pittsfield, MA 01201
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  /12

  $225,000

  • 4 Beds
  • 2 Baths
  • 1,734 Sq Ft

  21 Pleasant St, Pittsfield, MA 01201

  Two-family flat with each unit featuring 2 bedrooms/ 1 bath and separate natural gas heat, hot water & electric. There is a nice fenced in yard divided for each apartment, plus good off street parking! This home is close to downtown Pittsfield and would make a great home or addition to your portfolio!*Can be sold as a package with the two-family at 36 Division St in Pittsfield.

  Maria Liccardi Lamacchia Realty, Inc.

  21 Pleasant St, Pittsfield, MA 01201
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  /36

  $354,000

  • 4 Beds
  • 2 Baths
  • 1,610 Sq Ft

  111 Oak Hill Rd, Pittsfield, MA 01201

  This may be the convenient location you are looking for....... a quiet neighborhood lane surrounded by a lovely yard just minutes from shopping, markets, restaurants and a golfcourse. This charming four bedroom, 2 bath Cape has a most desirable layout for bothgathering and privacy. Two main level bedrooms or an office and full bath with a livingroom open to dining/kitchen and direct access to

  Mary Jane White COHEN & WHITE ASSOCIATES

  111 Oak Hill Rd, Pittsfield, MA 01201
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  /31

  $634,900

  • 4 Beds
  • 2.5 Baths
  • 2,464 Sq Ft

  4 Filomena Dr, Pittsfield, MA 01201

  Beautifully updated 4 bed, 3 bath Colonial in southeast Pittsfield. Inside boasts a bright, open floor plan with new stainless steel appliances and a fully finished basement offering additional square footage.Outside offers a serene wooded vista, with a year round brook, enjoyed from the updated composite deck and stone patio. Abutted by an expansive network of walking/biking trails, the natural

  Joseph Jennings SIGNATURE ASSOCIATES

  4 Filomena Dr, Pittsfield, MA 01201
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  /28

  $525,000

  • 4 Beds
  • 2.5 Baths
  • 2,477 Sq Ft

  50 Bellmore Dr, Pittsfield, MA 01201

  Immaculate, sparkling, light and bright 2500 square foot contemporary home in one of south east Pittsfield's finest neighborhoods with a level, sunny fenced yard, updated kitchen with granite counters, gleaming wood floors, fireplace, updated baths, newer systems. 4 bedrooms, 2.5 baths. There is even a two car garage. You will not be disappointed. This is a beautiful home in a wonderful

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  50 Bellmore Dr, Pittsfield, MA 01201
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  /38

  $220,000

  • 2 Beds
  • 1 Bath
  • 883 Sq Ft

  66 Orlando Ave, Pittsfield, MA 01201

  Small house with a lot to offer! This cozy single level ranch home has undergone many recent updates, including new roof, new siding, new sewer line, new HVAC mini split systems, and new hot water heater and exterior doors Kitchen features stainless steel appliances and laundry area with stacked washer dryer. Two bedrooms w/ good size closets. Outside is a powered shed in the partially fenced

  Conor Meehan STONE HOUSE PROPERTIES, LLC

  66 Orlando Ave, Pittsfield, MA 01201
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  /41

  $295,000

  • 3 Beds
  • 3 Baths
  • 3,250 Sq Ft

  1219 North St, Pittsfield, MA 01201

  Lots of space to spread out. Come check out this centrally located Enormous 3 bedroom 3 bath home in Pittsfield. Tons of potential to convert it into a two family home and/or use it for your business. The first foor has an open space concept with large kitchen / Dining Room and grand living room area. the second floor has a primary suite, 2 large bedrooms and a full bathroom. The third floor

  Jim Thurston LAMACCHIA REALTY, INC

  1219 North St, Pittsfield, MA 01201
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  /28

  $274,900

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft

  326 Dalton Ave, Pittsfield, MA 01201

  Adorable 3-bedroom, 1-bathroom Cape-style home with a detached one-car garage, perfectly situated on Dalton Ave. This charming property features a convenient first-floor bedroom, full bathroom, and laundry. Enjoy spacious bedrooms, a formal dining room, a cozy fireplace, and a mudroom with pantry and laundry. Beautiful hardwood floors throughout most of the home, with updated vinyl flooring in

  Jessie Downer LAMACCHIA REALTY, INC

  326 Dalton Ave, Pittsfield, MA 01201
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  /26

  $449,000

  • 4 Beds
  • 1.5 Baths
  • 1,610 Sq Ft

  469 Pecks Rd, Pittsfield, MA 01201

  Nestled on half an acre of prime Lake Onota waterfront, this 4-bedroom, 2-bathroom lake house is a fantastic opportunity for someone to make it their own. With all new windows and doors, and a newly installed heating system, the home is ready for you to add your personal touch and transform it into a stunning lakeside retreat. The spacious layout provides plenty of room for family and friends,

  Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  469 Pecks Rd, Pittsfield, MA 01201
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  /27

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  26 Crosier Ave, Pittsfield, MA 01201

  Motivated Seller!!! Come see this Charming, well-maintained home located in the heart of Pittsfield, MA. This inviting property offers a comfortable living space with plenty of potential. This home features 3 bedrooms, 2 baths, with a bright and spacious layout that maximizes natural light throughout.Enjoy the convenience of a functional kitchen, a cozy living room, and generously sized bedrooms.

  Marci Levesque BISHOP WEST REAL ESTATE

  26 Crosier Ave, Pittsfield, MA 01201
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  /20

  $799,000

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

  5 Aspen Way, Pittsfield, MA 01201

  Great opportunity to custom design your 2000 square foot free-standing condo home at Berkshire Country Meadows! This is one of only a few remaining sites in this established community. Close to Pontoosuc Lake and centrally located for all Berkshire attractions. Association has a club house with fitness equipment, pool and tennis. Select from several floor plans which feature a contemporary

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  5 Aspen Way, Pittsfield, MA 01201
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  /92

  $744,000

  • 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

  10 Lillybrook Rd, Pittsfield, MA 01201
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  /12

  $1,200,000

  • 4 Beds
  • 3.5 Baths
  • 3,409 Sq Ft

  140 Westbrook Terrace, Pittsfield, MA 01201

  Introducing a stunning and spacious ''to be built'' single-story home designed with expandable second floor for comfortable and upscale living. Boasting over 3,400 square feet of well-appointed living space, which includes the finished lower level, this residence offers four bedrooms, three and a half bathrooms, and an array of quality finishes that elevate the living experience. As you enter

  Corey Bishop BISHOP WEST REAL ESTATE

  140 Westbrook Terrace, Pittsfield, MA 01201

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