Berkshire, MA Homes for Sale

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  /13

  $313,000

  • 2 Beds
  • 3 Baths
  • 1,770 Sq Ft

  2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240

  If you are looking for location, Rolling Hills is the place to be. Just minutes from Tanglewood, Shakespeare & Company, skiing, arts, and all of the Culture the Berkshires has to offer. This unit is right across from the Clubhouse/Pool/fitness room. This unit has 2 bedrooms, 3 baths, and additional family room on the lower level. Enjoy the Tennis/pickle ball courts or take swim in the pool or

  Toni Marie Gage SIGNATURE ASSOCIATES

  2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240
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  /58

  $4,995,000

  • 7 Beds
  • 8 Baths
  • 13,261 Sq Ft

  319 Under Mountain Rd, Lenox, MA 01240

  Pine Needles.Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest,

  Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  319 Under Mountain Rd, Lenox, MA 01240
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  /6

  $75,000

  • 12 Beds
  • 5 Baths
  • 4,032 Sq Ft

  48 Brown St, Pittsfield, MA 01201

  Opportunity knocks! This 4-family property has suffered significant fire damage and is being sold as-is for land value. Ideal tear down project with endless redevelopment potential. The lot includes a detached garage and offers ample space for new construction. Bring your vision and rebuild in a growing area with strong rental demand. Cash or construction financing only. All offers considered.

  Xavier Cruz Fathom Realty

  48 Brown St, Pittsfield, MA 01201
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  /30

  $299,900

  • 1 Bed
  • 1 Bath
  • 1,404 Sq Ft

  12 Jones Ave, Pittsfield, MA 01201

  Welcome to this modern and energy-efficient home built in 2020, offering just over 1400 sq ft of flexible living space on a spacious 0.28-acre lot. The open layout features a large living area, one generously sized bedroom, and a full bath; all on a slab foundation with gas heat. Perfect for a first-time buyer, downsizer, or anyone seeking single-level living with room to expand or customize.

  Christina Parkington Lamacchia Realty, Inc.

  12 Jones Ave, Pittsfield, MA 01201
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  /6

  $58,000

  • Land
  • 0.25 Acre
  • $232,000 per Acre

  16 Harold St, Pittsfield, MA 01201

  Southeast Pittsfield building lot, town sewer and water and utilities on street. 185 ft deep. Perfect for single- or two-family construction. Significant fencing, short driveway and landscaping in place. Perfectly level and cleared home site.

  Paula McLean PAULA MCLEAN REALTORS INC.

  16 Harold St, Pittsfield, MA 01201
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  /12

  $169,000

  • 3 Beds
  • 1.5 Baths
  • 1,614 Sq Ft

  70 S Onota St, Pittsfield, MA 01201

  Bring your vision and make this spacious home your own! This property needs some work and has smoke damage from a previous fire but offers great potential for the right buyer or investor. The first floor features a large living room, formal dining room, kitchen and half bath all featuring impressive high ceilings. Upstairs you'll find three bedrooms and a full bathroom, and a walk-up attic that

  Jessica Rizzo LAMACCHIA REALTY, INC

  70 S Onota St, Pittsfield, MA 01201
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  /70

  $1,290,000

  • 3 Beds
  • 2.5 Baths
  • 2,844 Sq Ft

  257 W Mountain Rd, Lenox, MA 01240

  Nestled in the heart of the Berkshires, 257 W Mountain Road offers a rare blend of luxury and tranquility. This exquisite property is set on a serene, tree-lined road just minutes from downtown Lenox and Tanglewood. With refined finishes, spacious living areas, and walls of windows framing the lush landscape, every detail reflects elegance and comfort. The landscaped grounds feature stone

  Nicole Moore KELLER WILLIAMS REALTY

  257 W Mountain Rd, Lenox, MA 01240
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  /33

  $266,500

  • 3 Beds
  • 1 Bath
  • 1,170 Sq Ft

  54 Dutchess Ave, Pittsfield, MA 01201

  Welcoming 54 Dutchess Ave in Pittsfield to the market! The home is ideal for anyone seeking single level living. Step inside to find a spacious living area filled with natural light that is ideal for entertaining or relaxing. The well appointed eat-in kitchen offers ample storage and plenty of space. Down the hall are three cozy bedrooms that provide for a peaceful retreat along with a full

  Doug Collins LAMACCHIA REALTY, INC

  54 Dutchess Ave, Pittsfield, MA 01201
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  /114

  $929,900

  • 4 Beds
  • 2.5 Baths
  • 3,608 Sq Ft

  67 Dunmore Ct, Lenox, MA 01240

  This gorgeous 4-bedroom, 3-bathroom home sits on a spacious corner lot surrounded by beautiful native landscaping, offering both privacy and curb appeal. Step inside to find a bright and inviting layout with ample space for entertaining and everyday living. The kitchen features newly redone floors (2025), and the large back deck provides the perfect space for outdoor gatherings or quiet

  Sara Bresett NOCHER REALTY

  67 Dunmore Ct, Lenox, MA 01240
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  /25

  $259,900

  • 2 Beds
  • 1.5 Baths
  • 750 Sq Ft

  75 Maryland Ave, Pittsfield, MA 01201

  Pleasant ranch-style home with attached garage, in a sought after neighborhood. This home boasts a spacious, private, enclosed screened porch overlooking a fully fenced-in, large back yard with storage shed. First floor offers a cozy charm, with natural wood flooring, spacious two bedrooms and a full bath. Basement has a partially finished family room, half-bath, laundry room and storage/pantry

  Susan Calkins STONE HOUSE PROPERTIES, LLC

  75 Maryland Ave, Pittsfield, MA 01201
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  /69

  $950,000

  • 4 Beds
  • 4 Baths
  • 3,876 Sq Ft

  189 Red Barn Rd, Dalton, MA 01226

  189 Red Barn Road is 3876 square feet of easy living. Solid oak floors, gas range, granite counter tops, custom cherry kitchen cabinets, surround sound, primary suite is located on the first level. The garden level, features two en-suite bedrooms and a wet bar. The home has private panoramic views and is a short walk to the sports complex.Silver Maple Farm is arguably the best and most desirable

  Buddy Lewis BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  189 Red Barn Rd, Dalton, MA 01226
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  /42

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,760 Sq Ft

  72 Cleveland St, Pittsfield, MA 01201

  Stylish Southeast contemporary on a quiet dead-end street near Brattle Brook Park! This versatile 3-bed, 2.5-bath home features a bright open floor plan with vaulted ceilings, a sunken living room with wood-burning fireplace, and an eat-in kitchen. The formal dining room can also serve as a home office or flex space.Two bedrooms and a 1.5 baths are located on the main level with a spacious

  Heather Gallagher JAN PERRY REALTY & ASSOCIATES, LLC

  72 Cleveland St, Pittsfield, MA 01201
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  /22

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,160 Sq Ft

  33 Quirico Dr, Pittsfield, MA 01201

  Welcome to this charming 3 bedroom ranch located in one of Pittsfield's most desirable neighborhoods. Warm and inviting, this home features beautiful hardwood floors, a cozy wood-burning fireplace, and cedar-lined closets in each bedroom. The kitchen and dining area open to a deck through sliding glass doors, offering the perfect setup for summer BBQs and indoor-outdoor living.Downstairs, a

  Danielle Giulian WILLIAM PITT SOTHEBY'S - LENOX

  33 Quirico Dr, Pittsfield, MA 01201
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  /5

  $39,000

  • Land
  • 0.41 Acre
  • $95,120 per Acre

  33 Circular Ave, Pittsfield, MA 01201

  Building lot that is well located and cleared in downtown Pittsfield. City lot is 0.41 acres, approved for building Single Family or Multi-Family up to 4 units and fits within the Multi-Family Residential zone (R-M). Walk-able and close to all amenities including restaurants, grocery stores, shops and public transportation. Water, sewer and gas available on the street. Proximity to the region's

  Cory Evangelisto NOCHER REALTY

  33 Circular Ave, Pittsfield, MA 01201
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  /57

  $635,000

  • 3 Beds
  • 2.5 Baths
  • 1,720 Sq Ft

  4 Evergreen Trail, Lenox, MA 01240

  Heirloom peonies and fragrant David Austin rose varieties adorn the walkway of this Berkshire hidden gem inviting you into tranquillity, peace and calm. Once indoors, you'll find easy living. The first level has an open kitchen and living area with a gas fireplace, large primary bedroom with a full bath and walk-in closet along with a screened in patio which overlooks a well established low

  Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  4 Evergreen Trail, Lenox, MA 01240
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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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  /3

  $268,500

  • 3 Beds
  • 3 Baths
  • 1,603 Sq Ft

  79 Center St, Pittsfield, MA 01201

  Spacious three-family home in the heart of Pittsfield's vibrant Downtown Cultural District! This property features a total of 3 bedrooms, offering strong rental potential and versatility. Recent capital improvements include newer roof and siding, reducing immediate maintenance costs and boosting curb appeal. Situated in a highly desirable, walkable location near restaurants, the Berkshire

  Heather Gallagher JAN PERRY REALTY & ASSOCIATES, LLC

  79 Center St, Pittsfield, MA 01201
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  /50

  $175,500

  • 6 Beds
  • 2.5 Baths
  • 3,216 Sq Ft

  27 Daniels Ave, Pittsfield, MA 01201

  Spacious side-by-side duplex offering three bedrooms in each unit. Hardwood floors throughout each unit along with a front/rear porch, first floor laundry, and separate utilities. Loads of additional space in attic and basement for storage or potential future expansion of living space. HUD Home. LBP. Sold ''AS IS'' by elec. bid only. Prop avail 06-12-25. Bids due by 06-22-25 by 11:59 PM Central

  Cory Evangelisto NOCHER REALTY

  27 Daniels Ave, Pittsfield, MA 01201
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  /12

  $184,900

  • 3 Beds
  • 2 Baths
  • 1,217 Sq Ft

  158 Second St, Pittsfield, MA 01201

  Two-family flat located in a corner lot, centrally located within walking distance to downtown! The first floor unit features 2 bedrooms/1 bath, and has electric heat. The second floor unit is a 1 bedroom/1 bath, with natural gas heat. Both units are currently rented, with tenants pay for their own heat/hot water/electricity separately. There is a paved parking area on the back of the home. One

  Maria Liccardi Lamacchia Realty, Inc.

  158 Second St, Pittsfield, MA 01201
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  /41

  $350,000

  • 6 Beds
  • 3 Baths
  • 3,366 Sq Ft

  151 Onota St, Pittsfield, MA 01201

  First Bulk showings/open house 6/13/25 11-12:30! Welcome to this fully rented professionally managed 3-family investment opportunity at 151 Onota St in Pittsfield! Each spacious unit features 2 bedrooms and 1 bathroom, offering excellent rental income potential. The second and third floors are occupied by long-term tenants, while the first floor welcomed new tenants as of June 1st. Don’t miss

  Michael Johnson Lock and Key Realty Inc.

  151 Onota St, Pittsfield, MA 01201
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  /12

  $184,900

  • 3 Beds
  • 2 Baths
  • 1,217 Sq Ft

  160 Second St, Pittsfield, MA 01201

  Two-family flat located in a corner lot, centrally located within walking distance to downtown!The first floor unit features 2 bedrooms/1 bath, and has electric heat. The second floor unit is a 1 bedroom/1 bath, with natural gas heat. Both units are currently rented, with tenants pay for their own heat/hot water/electricity separately. There is a paved parking area on the back of the home. One

  Maria Liccardi LAMACCHIA REALTY, INC

  160 Second St, Pittsfield, MA 01201
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  /43

  $799,000

  • 7 Beds
  • 7 Baths
  • 4,290 Sq Ft

  17 - 23 Linden St, Pittsfield, MA

  Incredible Multi-Unit Investment Opportunity in Downtown Pittsfield!Located just steps from the Barrington Stage Company theater in the heart of the cultural district, this dynamic property includes two fully occupied buildings plus a 4-bay garage, making it a true income-generating powerhouse. With a solid 11.2 cap rate, this is a rare opportunity for both the savvy investor and the live-in

  Michael Castellano Gilcrest Properties

  17 - 23 Linden St, Pittsfield, MA
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  /44

  $629,500

  • 4 Beds
  • 4.5 Baths
  • 3,081 Sq Ft

  24 Alpine Trail, Pittsfield, MA 01201

  Welcome to your Berkshire retreat! This spacious 4-bedroom, 5-bath condo at The Pines of Bousquet is a rare corner unit filled with natural light and sweeping views of the bunny ski slope--right in your backyard. Whether you're watching skiers in the winter from your office nook on the second floor, or enjoying peaceful greenery in warmer months from your screened porch, this home offers

  Tanya Shepardson LAMACCHIA REALTY, INC

  24 Alpine Trail, Pittsfield, MA 01201
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  /4

  $50,000

  • Land
  • 1.10 Acres
  • $45,455 per Acre

  0 Hungerford St, Pittsfield, MA 01201

  Build Your Dream Home on 1.1 Acres. Don’t miss this rare opportunity to own a spacious 1.1-acre buildable lot, perfect for your custom single-family home. Located in a peaceful setting and convenience, this lot offers level terrain and is ready for development with utilities water, sewer, electric available at the street. Whether you’re looking to build now or invest for the future, this property

  Xavier Cruz Fathom Realty

  0 Hungerford St, Pittsfield, MA 01201
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  /22

  $284,888

  • 4 Beds
  • 2 Baths
  • 2,132 Sq Ft

  50 John St, Pittsfield, MA 01201

  This two-family home was renovated in the last two years! Improvements include roof, windows, flooring, painting, and more! The home offers an enclosed front porch to access both units, and a side porch for each apartment independently. Each unit features living room, dining room, kitchen, 2 bedrooms and 1 bath. There is separate heat, hot water and electric: Unit 52 has natural gas heat while

  Maria Liccardi Lamacchia Realty, Inc.

  50 John St, Pittsfield, MA 01201
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  /50

  $1,950,000

  • 5 Beds
  • 4.5 Baths
  • 4,301 Sq Ft

  20 E Dugway Rd, Lenox, MA 01240

  Lenox Estate on 36 Acres - Two HomesJust one mile from the center of Lenox, this unique estate offers exceptional space and versatility with two separate residences. The main home boasts 4,100 square feet with five bedrooms and three and a half bathrooms--perfect for spacious living or entertaining. The second home is a charming 1,200-square-foot residence with two bedrooms and two full baths,

  Tanya Shepardson LAMACCHIA REALTY, INC

  20 E Dugway Rd, Lenox, MA 01240
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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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  /38

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,405 Sq Ft

  880 East St Unit 1A, Lee, MA 01238

  Desirable end unit at October Mountain Village in Lee, MA, offering a serene and picturesque setting. This unit is a short stroll to the tennis courts and community pool. The open-concept living and dining areas feature laminate flooring and a charming two-sided wood-burning fireplace, shared with the vaulted family room. Two skylights and a ceiling fan bring abundant natural light and airflow.

  Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  880 East St Unit 1A, Lee, MA 01238
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  /33

  $525,000

  • 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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  /45

  $289,900 Open Wed 5:30AM - 7PM

  • 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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  /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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  /45

  $569,777

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft

  31 Saint Ann's Ave, Lenox, MA 01240

  OWN - Instead of Renting - this Tanglewood Season! A unique opportunity with past rental income up to $16,000 for the summer months--ideal for music lovers and art-minded Berkshires visitors. This 1915 gem--the Claude and Louise Delahaye House--is tucked away on peaceful St. Ann's Ave, just steps from the iconic St. Ann's Church. Enjoy an easy stroll to downtown Lenox's shops, dining, and

  Audrey Matys BERKSHIRE LISTINGS

  31 Saint Ann's Ave, Lenox, MA 01240
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  /25

  $374,900

  • 3 Beds
  • 1 Bath
  • 1,986 Sq Ft

  349 New Lenox Rd, Lenox, MA 01240

  Spacious 3 Bed/1 Bath Colonial located in a quiet Lenox neighborhood. This charming home offers: gleaming hardwood floors, an oversized family room which could be used as a 1st floor primary, a new Refrigerator & Stove, Washer & Dryer hook ups on the 1st floor, attached garage, steam heat and plenty of light throughout! Savor the beautiful Berkshires, while you lounge in your expansive flat

  Timothy Johnson NOCHER REALTY

  349 New Lenox Rd, Lenox, MA 01240
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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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  /52

  $765,000

  • 5 Beds
  • 4.5 Baths
  • 3,381 Sq Ft

  33 Alpine Trail, Pittsfield, MA 01201

  Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and

  Cortney Dupont COHEN & WHITE ASSOCIATES

  33 Alpine Trail, Pittsfield, MA 01201
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  /12

  $12,900

  • Land
  • 0.46 Acre
  • $28,096 per Acre

  0 Longview Terrace, Pittsfield, MA 01201

  Waterfront Lot! This lightly wooded untouched lot in a quiet well established neighborhood has frontage on Goodrich Pond. Electric, water, sewer and cable are all availible at road.

  Timothy Johnson NOCHER REALTY

  0 Longview Terrace, Pittsfield, MA 01201
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  /46

  $539,000

  • 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

  $519,000

  • 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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  /29

  $692,000

  • 4 Beds
  • 3.5 Baths
  • 3,296 Sq Ft

  14 Alpine Trail Unit 14, Pittsfield, MA 01201

  Welcome to your dream mountain retreat! This stunning end unit in a community of 96 units offers an unparalleled lifestyle for outdoor enthusiasts. With effortless access to ski trails right from your back screened-in porch, you can hit the slopes at Bousquet Mountain anytime you desire.Spanning over 3,200 square feet, this 4-bedroom, 3.5-bath condo has a spacious three-level layout. Step inside

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  14 Alpine Trail Unit 14, Pittsfield, MA 01201
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  /13

  $269,000

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

  61 Pomeroy Ave, Pittsfield, MA 01201

  Investment Opportunity on Pomeroy Ave! 2 Family flat with each unit boasting a spacious layout with 3 bedrooms and 1 full bath. Both units are currently rented, offering immediate income. Convenient location close to the heart of downtown and the cultural district of Pittsfield.

  Jessie Carlino MACCARO REAL ESTATE

  61 Pomeroy Ave, Pittsfield, MA 01201

Showing Results 41 - 80, Page 2 of 3