Berkshire, MA Homes for Sale

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  /38

  $879,000

  $120K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,262 Sq Ft

  22 Post Rd, Lenox, MA 01240

  Welcome home to an extraordinary blend of modern style, flexible living, and resort-quality outdoor amenities, perfectly located moments from the heart of downtown Lenox, top-notch dining, Tanglewood, & the local high school on a quiet cul-de-sac. Step inside to a bright, freshly painted open floor plan framed by updated windows that flood the space with natural light. The inviting living area

  India Ward NON-MEMBER / RECIPROCAL

  22 Post Rd, Lenox, MA 01240
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  /32

  $219,900

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 909 Sq Ft

  68 Orchard St, Pittsfield, MA 01201

  Recently renovated home with convenient first floor bedroom and full bathroom, and two additional bedrooms on the second floor. The front yard is fenced in. The backyard is a great space to gather.The basement has concrete floor and there is natural gas heat and hot water, and metered water. The home has a certificate of insulation and it shows how helpful it is as the utility bills are very

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  68 Orchard St, Pittsfield, MA 01201
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  /32

  $359,900

  • 4 Beds
  • 4 Baths
  • 3,180 Sq Ft

  1093 Tyler St, Pittsfield, MA 01201

  Investment Opportunity in Pittsfield! Well-maintained four-family flat offering four spacious 1-bedroom, 1-bath apartments. Each unit features separate utilities, providing tenants with individual responsibility for their utility costs. Natural gas heat and hot water add to the property's efficiency and appeal. Centrally located with convenient access to shopping, dining, schools, public

  Doug Collins Lamacchia Realty, Inc. - Dalton

  1093 Tyler St, Pittsfield, MA 01201
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  /23

  $209,900

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 866 Sq Ft

  139 2nd St, Pittsfield, MA 01201

  The home just passed an FHA appraisal and appraised over the asking price! This renovated home offers two bedrooms and two bathrooms. The first floor features an enclosed front porch, living room, foyer, full bathroom, laundry room and updated kitchen with new quartz countertops and stainless appliances. Upstairs you will find two bedrooms and half bathroom. Both of the bathrooms have been

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  139 2nd St, Pittsfield, MA 01201
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  /53

  $679,900

  • 4 Beds
  • 3.5 Baths
  • 2,682 Sq Ft

  16 Juliana Dr, Pittsfield, MA 01201

  Welcome to this spacious and beautifully renovated 4 bedroom home in desirable Southeast neighborhood. With 3 full bathrooms and 1 half bath, this home provides plenty of room for family and guests. The open floor plan creates an inviting flow between the generously sized living spaces, while the renovated interior offers a fresh, modern feel. The impressive primary suite features a walk-in

  Robin Moore 413 REAL ESTATE

  16 Juliana Dr, Pittsfield, MA 01201
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  /19

  $649,900

  • Land
  • 3.67 Acres
  • $177,084 per Acre

  37 Elm St, Pittsfield, MA 01201

  Prime downtown opportunity! Almost 4 acres ready for your development ideas. One of Pittsfield's last remaining sites large enough for drive thru permit.Ther front of the property is BG, the back is CWS. Very versatile site on one of Pittsfield's finest streets.

  Steve Ray 413 REAL ESTATE

  37 Elm St, Pittsfield, MA 01201
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  /5

  $235,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,947 Sq Ft

  15 Noble Ave, Pittsfield, MA 01201

  Two family duplex just outside of downtown. Featuring two bedrooms and one bathroom in each unit with hardwood floors. Off Street parking and separate utilities. Please reach out for interior photos.

  Cory Evangelisto NOCHER REALTY

  15 Noble Ave, Pittsfield, MA 01201
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  /44

  $595,000

  • 3 Beds
  • 2 Baths
  • 2,217 Sq Ft

  139 Mountain Dr, Pittsfield, MA 01201

  Situated on highly desirable Mountain Drive, this expanded 3-bedroom, 2-bath Cape delivers classic Berkshire charm, thoughtful updates, and flexible living spaces. Step inside from the welcoming front porch into an inviting layout featuring hardwood floors and abundant natural light. The spacious living room is anchored by a wood-burning fireplace flanked by custom built-ins, flowing into the

  Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  139 Mountain Dr, Pittsfield, MA 01201
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  /68

  $419,900

  • 3 Beds
  • 4 Baths
  • 2,269 Sq Ft

  1112 South St, Dalton, MA 01226

  If space, flexibility, & a great backyard are on your wish list, this home is one to see! Thoughtfully expanded over the years, the home offers a versatile layout with generously sized bedrooms on both the first and second floors, four bathrooms, and plenty of bonus space. The back addition is especially inviting, featuring a large living room and dining room with plenty of space to gather.

  Jessie Downer Lamacchia Realty, Inc. - Dalton

  1112 South St, Dalton, MA 01226
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  /14

  $179,900

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  55 Pomeroy Ave Unit 3, Pittsfield, MA 01201

  Enjoy carefree condo living in this charming historic home, where timeless character meets modern convenience. Beautiful hardwood floors and thoughtful updates blend seamlessly with the home's original charm, creating a warm and inviting atmosphere. Nestled in a peaceful community, this unique property is just a short stroll from downtown dining, local shops, art galleries, and cultural

  Michele Purcell Lamacchia Realty, Inc. - Dalton

  55 Pomeroy Ave Unit 3, Pittsfield, MA 01201
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  /34

  $289,900

  $30K PRICE DROP Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,566 Sq Ft

  73 Plymouth St, Pittsfield, MA 01201

  Recently off market for needed maintenance on the exterior siding and landscaping, this home is now a must-see! Colonial style home is bright and airy featuring windows that invite abundant natural sunlight into every room. The main level offers a easy flow between the inviting living spaces and a convenient half-bath, while the second floor hosts three generous bedrooms and a full bath.A walk-up

  Jason Nocher NOCHER REALTY

  73 Plymouth St, Pittsfield, MA 01201
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  /20

  $185,000

  • 2 Beds
  • 1.5 Baths
  • 1,506 Sq Ft

  7 Lincoln St, Pittsfield, MA 01201

  ''The Castle'' on Lincoln! Distinctive architecture and generous living spaces give this home incredible potential. The striking stone exterior, curved bay windows, second-floor balcony, hardwood floors, and vintage details create character that's hard to find. The spacious interior offers a flexible layout with an open connection between the living, dining, and kitchen areas. The second bedroom

  Jonathan Vella Lamacchia Realty, Inc. - Dalton

  7 Lincoln St, Pittsfield, MA 01201
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  /59

  $3,925,000

  • 8 Beds
  • 8.5 Baths
  • 6,000 Sq Ft

  17 Main St, Lenox, MA 01240

  Extraordinary opportunity to own a showcase of New England history and hospitality--17 Main Street, a masterfully restored Berkshire cottage in the vibrant heart of downtown Lenox. Originally built in 1883 and once owned by Gilded Age shipping magnate John Schermerhorn, this landmark property blends historic grandeur with modern comfort. Between 2021 and 2025, the residence underwent a

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  17 Main St, Lenox, MA 01240
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  /21

  $339,900

  Open Sat 10AM - 12PM

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

  1981 East St, Pittsfield, MA 01201

  MOVE IN READY! Charming 4-bedroom, 1½-bath Cape in Southeast Pittsfield, located in Williams Elementary School district! This well-maintained home features beautiful hardwood floors, natural gas heat, a first-floor bedroom and walk-in shower, abundant storage, and a partially finished basement ideal for a family room, home office, or home gym. Enjoy the rare bonus of an included rear lot,

  Anthony Riello Lamacchia Realty, Inc. - Dalton

  1981 East St, Pittsfield, MA 01201
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  /28

  $207,000

  $22K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 902 Sq Ft

  1 Colt Rd Unit 1, Pittsfield, MA 01201

  Welcome to easy, in-town living at sought-after One Colt Road in a charming neighborhood. This first-floor condominium offers the perfect blend of convenience and comfort, just a short stroll to Berkshire Museum, Colonial Theatre, local restaurants, and boutique shops. Featuring 2 bedrooms and 1 bath, the layout is both functional and inviting. A rare screened porch extends your living space,

  Victoria Standring Lamacchia Realty, Inc. - Dalton

  1 Colt Rd Unit 1, Pittsfield, MA 01201
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  /45

  $575,000

  $25K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft

  24 Brunell Ave, Lenox, MA 01240

  Location, location, location! Ideally situated within easy walking distance of the village, elementary school, and Tanglewood, this charming ranch offers comfortable single-level living in a quiet, desirable neighborhood. The large, level and semi-private backyard provides plenty of room to relax, entertain, garden, or enjoy the above-ground pool. Inside, the home features a spacious open living

  Melissa Dimassimo STONE HOUSE PROPERTIES, LLC

  24 Brunell Ave, Lenox, MA 01240
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  /28

  $299,900

  • 3 Beds
  • 1 Bath
  • 942 Sq Ft

  21 Austin Ave, Pittsfield, MA 01201

  Welcome to this beautifully renovated 3-bedroom ranch, perfectly situated on a quiet dead-end street in Southeast. This move-in-ready home features a brand-new roof, new windows, new flooring throughout, and a completely updated kitchen and bathroom. The thoughtful renovations offer a fresh, modern feel while maintaining the comfortable layout and easy living of a classic ranch. Outside, enjoy a

  Robin Moore 413 REAL ESTATE

  21 Austin Ave, Pittsfield, MA 01201
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  /4

  $898,000

  • Land
  • 12.84 Acres
  • $69,938 per Acre

  21 Dan Fox Dr, Pittsfield, MA 01201

  12.84 Acres of Prime development Land. Ideal for possible Commercial and/or Residential projects. Close to Shopping and Transportation. Curb cut and some engineering done.

  Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  21 Dan Fox Dr, Pittsfield, MA 01201
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  /47

  $645,000

  $30K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 4,832 Sq Ft

  1 Eaton Ln, Pittsfield, MA 01201

  Elegance Meets History on 1 Eaton Lane!Tucked away on a quiet, sought-after street just minutes from the Country Club of Pittsfield & only 10 minutes to vibrant downtown Lenox, this remarkable Colonial seamlessly blends timeless character with extraordinary versatility. Offering just under 5,000 square feet of living space, this historic estate presents a rare opportunity for those seeking a

  Stacy Chojnowski WILLIAM PITT SOTHEBY'S - LENOX

  1 Eaton Ln, Pittsfield, MA 01201
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  /43

  $699,000

  $51K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,159 Sq Ft

  208 Karen Dr, Pittsfield, MA 01201

  Charming open-concept Ranch includes a separate abutting building lot in the heart of the Berkshires on a quiet non-through street! This beautiful, move-in ready Ranch offers 1,959 sq ft of bright, inviting living space on the main level. Finished 1159 sq ft basement with full bath adds extra space, perfect for a game room, holiday gatherings. The dining area connects to a large kitchen with

  Susan Calkins STONE HOUSE PROPERTIES, LLC

  208 Karen Dr, Pittsfield, MA 01201
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  /21

  $310,000

  • 6 Beds
  • 4 Baths
  • 2,946 Sq Ft

  25 Root Place Unit 25-27, Pittsfield, MA 01201

  This newly remodeled 2 family home boast 3+ bedrooms and 1.5 bathrooms on each side. The work has been completed and it's ready for either a rental property or an owner occupied home. The renovations include, new kitchens, bathrooms, floors and also a new boiler in 2026. The laundry rooms are conveniently located in units. There is off street parking, a large private back yard with a shed.

  Janet Benoit MOCKINGBIRD REAL ESTATE

  25 Root Place Unit 25-27, Pittsfield, MA 01201
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  /10

  $320,000

  $5K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,378 Sq Ft

  89 Robbins Ave, Pittsfield, MA 01201

  Great Two family with some updates. Hardwood floor in dining room and bedrooms. Kitchen and bathroom with Ceramic floor. Newer Roof. Parking off street for 4 cars

  Al DeSouza First Option Properties Inc.

  89 Robbins Ave, Pittsfield, MA 01201
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  /2

  $69,000

  • Land
  • 3.3 Acres
  • $20,909 per Acre

  75 Woodland Rd, Lee, MA 01238

  Over 3 acres of wooded land on Woodland Road in Lee near October Mountain State Forest. Previously used for logging, this parcel features a wooded, sloping landscape. Convenient to downtown Lee & Lenox and easy access to the Massachusetts Turnpike. Additional pastoral 1 acre parcel available at 60 Woodland Rd., may be purchased together or separately. Buyers and buyer's agents to perform their

  Lisa Kelley MACCARO REAL ESTATE

  75 Woodland Rd, Lee, MA 01238
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  /20

  $259,900

  $30K PRICE DROP

  • 8 Beds
  • 2 Baths
  • 2,016 Sq Ft

  42 John St, Pittsfield, MA 01201

  Investment Opportunity with Owner-Occupant Potential! This well-maintained two-family home offers spacious 3-4 bedroom apartments in each unit, making it an excellent opportunity for investors or buyers looking to offset their mortgage with rental income. One unit is currently vacant, allowing for immediate occupancy or the ability to secure a new tenant at current market rents. The occupied unit

  Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  42 John St, Pittsfield, MA 01201
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  /62

  $625,000

  $25K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 3,524 Sq Ft

  15 Kenilworth St, Pittsfield, MA 01201

  Beautifully tucked away in one of Pittsfield's most established neighborhoods, this stately 5-bedroom, 5-bath home is a rare offering filled with warmth, character, and endless potential. From its gracious proportions to its timeless architectural details, this is a home that makes a lasting impression.Sun-filled living spaces, generously sized rooms, and a thoughtful layout provide the

  Heather Gallagher STONE HOUSE PROPERTIES, LLC

  15 Kenilworth St, Pittsfield, MA 01201
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  /34

  $269,900

  • 5 Beds
  • 2 Baths
  • 2,100 Sq Ft

  12 Lincoln St, Pittsfield, MA 01201

  Lovely five bedroom two bath Colonial on 5500+ sq.ft. of land.Lots of space, front porch for relaxing on beautiful summer evenings. Two bedrooms on the first floor and three bedrooms on the second floor with a deck off the bedroom and off the kitchen on the first floor. Two driveways for plenty of parking!!!Three sheds on property for storage will stay. Or not.

  Theresa Adams Dacey Realty, LLC

  12 Lincoln St, Pittsfield, MA 01201
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  /25

  $279,900

  Open Sat 11AM - 1PM $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,327 Sq Ft

  48 Plastics Ave, Pittsfield, MA 01201

  Renovated 3-Bedroom Cape in a Central Location. Welcome home to this newly renovated 3-bedroom Cape-style house, ideally situated in a convenient central location close to everyday amenities, local services, shopping, dining, and commuter routes. Combining classic Cape charm with fresh modern updates, this inviting home offers comfort, functionality, and move-in-ready appeal. Property highlights

  Dawn Vadnais MORESI REAL ESTATE PARTNERS

  48 Plastics Ave, Pittsfield, MA 01201
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  /21

  $249,000

  Open Sat 10AM - 11:30PM

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft

  21 Terrace Ave, Pittsfield, MA 01201

  Welcome to this cozy and well-maintained 2-bedroom, 1-bath Colonial, offering classic charm and a warm, inviting feel. A welcoming front porch, cute backyard, and meticulously landscaped grounds add to the home's wonderful curb appeal.Inside, the home has been lovingly cared for and is in very good condition, with a few cosmetic updates offering an opportunity to bring it into your preferred

  Tracy Munger KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  21 Terrace Ave, Pittsfield, MA 01201
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  /30

  $279,900

  • 5 Beds
  • 2 Baths
  • 1,933 Sq Ft

  77 Onota St, Pittsfield, MA 01201

  Step into the timeless elegance of this turn-of-the-century Victorian, where historic charm and modern comfort come together beautifully. Original architectural details create a warm and inviting atmosphere throughout, including soaring 9-foot ceilings, intricate crown molding, gleaming hardwood floors, and beautifully crafted built-ins. Spacious, light-filled rooms offer plenty of room to

  Audrey Matys BERKSHIRE LISTINGS

  77 Onota St, Pittsfield, MA 01201
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  /17

  $249,900

  $15K PRICE DROP

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

  32 Westminister St, Pittsfield, MA 01201

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

  The Ponte Group Keller Williams South Watuppa

  32 Westminister St, Pittsfield, MA 01201
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  /46

  $485,000

  • 4 Beds
  • 2 Baths
  • 1,720 Sq Ft

  500 Walker St, Lenox, MA 01242

  Envision waking up in this beautifully renovated New England farmhouse in quaint Lenoxdale Village. Enjoy morning sunrises on the front patio and quiet evening dinners on the terrace, all just minutes from the world-class culture of Tanglewood and the iconic downtowns of Lenox and Stockbridge. Inside, original hardwood floors flow throughout a versatile layout featuring 3-4 bedrooms, a cozy

  Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  500 Walker St, Lenox, MA 01242
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  /32

  $369,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  880 East St Unit 10C, Lee, MA 01238

  Immaculate unit in move-in condition. 1st floor bedroom and a 1st floor stall shower with glass door. Hugh 3 season room with glass and screens to enjoy the Berkshire air. Hardwood floors in living and dining area. Upscale stainless steel refrigerator and Bosch Dishwasher. Two bedrooms and full bath with tub/shower upstairs. Unfinished lower level with work bench, brand new washer and (older)

  Susan Baum BERKSHIRE HOMES AND CONDOS

  880 East St Unit 10C, Lee, MA 01238
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  /27

  $269,900

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,386 Sq Ft

  141 Dewey Ave, Pittsfield, MA 01201

  This 2 family flat is ready for it's new owner or someone looking for rental income. Both units have been remodeled with new kitchens, baths, flooring and fresh paint. Both units have enclosed porches. There is a large oversized commercial garage in the back that's perfect for storage, additional rental income. Easy walk up to the downtown area.

  Janet Benoit MOCKINGBIRD REAL ESTATE

  141 Dewey Ave, Pittsfield, MA 01201

Showing Results 121 - 153, Page 4 of 4