Homes for Sale near Hillcrest Educational Foundation

• 

  

  

  /41

  $360,000

  • 8 Beds
  • 4 Baths
  • 3,266 Sq Ft

  261 Pomeroy Ave, Pittsfield, MA 01201

  Spacious Fully -Rented Duplex Investment OpportunityDiscover an investment opportunity with strong income potential. This 3,266 sqft duplex, built in 1900, offers timeless character combined with functionally. Situated on .41 acres, with plenty of off-street parking, the property features 15 rooms, 8 bedrooms, and 4 full baths across both units, making it ideal for long-term rental stability.

  Marnie Garzone THE KINDERHOOK GROUP

  261 Pomeroy Ave, Pittsfield, MA 01201
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  /12

  $170,000

  • 6 Beds
  • 2 Baths
  • 2,128 Sq Ft

  242 Wahconah St, Pittsfield, MA 01201

  Investor Special! This gutted duplex offers a blank canvas with 6 bedrooms, 2 bathrooms, and 2,000 sqft of space, plus the possibility of additional living space in the attic. this property features a large backyard with a serene water stream, A standing garage remains on site for additional storage or future use. Situated on a 13,108 sqft lot, can also be bundled with 40 Pecks Rd & 48 Brown st

  Xavier Cruz Fathom Realty

  242 Wahconah St, Pittsfield, MA 01201
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  /27

  $364,900

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  100 Boylston Street Extension, Pittsfield, MA 01201

  Welcome to 100 Boyston Street Ext, an extensively updated Pittsfield home with every major element renewed for a warm, modern, turnkey feel. The first floor features a bright open layout, a brand new contemporary kitchen, and connected living and dining spaces. Two first floor bedrooms and a full bath add flexibility for single level living or guests.Upstairs primary suite with refinished

  Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

  100 Boylston Street Extension, Pittsfield, MA 01201
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  /27

  $249,900

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  50 Grand Ave, Pittsfield, MA 01201

  Amazing opportunity to own a home on 0.46 acres plus two additional lots with 0.46 and 0.17 acres each, totaling about 1.1 acres, in a private area, on a dead end street! The house is a fixer upper, the exterior is freshly painted, the interior needs renovation but all utilities and mechanicals are on. The first floor features a lovely enclosed front porch, dining room, living room and kitchen;

  Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.

  50 Grand Ave, Pittsfield, MA 01201
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  /22

  $249,000

  • 2 Beds
  • 1 Bath
  • 974 Sq Ft

  122 Allengate Ave, Pittsfield, MA 01201

  Enjoy easy, single-level living in this sunny and well-cared-for bungalow. Beautiful hardwood floors flow throughout the home, complemented by numerous recent updates, including a new electrical panel, replaced sewer line, new hot water heater, updated gutters, and a new slider.The welcoming entryway with hall closet leads to a spacious living room and an eat-in kitchen that opens to a generously

  Angel Black KRG - Key Realty Group

  122 Allengate Ave, Pittsfield, MA 01201
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  /14

  $124,900

  • 1 Bed
  • 1 Bath
  • 680 Sq Ft

  36 Beacon Ave, Pittsfield, MA 01201

  With a small floor plan this could be a great weekend getaway or easy every day living located on a .12 acre lot. this layout offers a one bedroom, office, kitchen, full bathroom and an enclosed entry way which would make an additional sitting area. The yard has ample space for gardening, outdoor gatherings or simply enjoying the peaceful surroundings. Just a short walk to Pontoosuc Lake where

  Michelle Picard NOCHER REALTY

  36 Beacon Ave, Pittsfield, MA 01201
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  /64

  $1,199,800

  • 9 Beds
  • 4.5 Baths
  • 5,319 Sq Ft

  5 Crofut St, Pittsfield, MA 01201

  Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, Upstreet Cultural District and is ideally just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  5 Crofut St, Pittsfield, MA 01201
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  /47

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 3,196 Sq Ft

  5 Eastbrook Ln, Pittsfield, MA 01201

  Located in the desirable, gated community of Woodmont Estates, this thoughtfully updated home offers a timeless layout, flexible living spaces, and easy access to the best of the Berkshires. Inside, vaulted ceilings, expansive windows, and hardwood oak floors create a light-filled and inviting atmosphere, anchored by a gas fireplace and elegant details. The custom kitchen serves as the heart of

  THE KAHN TEAM BISHOP WEST REAL ESTATE

  5 Eastbrook Ln, Pittsfield, MA 01201
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  /36

  $229,900

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft

  156 Elizabeth St, Pittsfield, MA 01201

  Charming 2-Family Flat - Great Investment or Owner-Occupied Opportunity!Don't miss this 2-family flat offering classic charm and modern convenience. Each spacious unit features hardwood floors The second-floor unit boasts an enclosed porch--perfect for relaxing or additional living space. Separate utilities, off street parking and shed add to the property. This property has potential to be used

  Robin Moore 413 REAL ESTATE

  156 Elizabeth St, Pittsfield, MA 01201
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  /33

  $469,900

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  59 Joan Dr, Pittsfield, MA 01201

  Welcome to 59 Joan Drive, a well appointed 4-bedroom, 2.5-bath raised ranch located in one of Pittsfield's premier neighborhoods. The main level boasts a bright living room, a modern kitchen with ample storage, and a dining area that opens to a spacious wrap around deck, ideal for outdoor gatherings. The master suite offers a private full bath, while three additional bedrooms provide plenty of

  Doug Collins LAMACCHIA REALTY, INC

  59 Joan Dr, Pittsfield, MA 01201
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  /20

  $249,900

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  1 Colt Rd Unit 2, Pittsfield, MA 01201

  Enjoy easy, low-maintenance living in this charming 2-bedroom, 1-bathroom main-level condo that includes a freestanding garage. Perfectly located just moments from downtown Pittsfield, this home offers the ideal blend of comfort and convenience.Step inside to a bright, open living space with single-level access throughout. The kitchen and living areas flow seamlessly, making everyday living and

  Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

  1 Colt Rd Unit 2, Pittsfield, MA 01201
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  /44

  $445,900

  • 4 Beds
  • 2 Baths
  • 2,606 Sq Ft

  133 Pomeroy Ave, Pittsfield, MA 01201

  Motivated Seller.! A home that is in move in condition Prestigious grand colonial located in the lovely Southeast area. This home has been meticulously maintained. Four large bedrooms, formal living room with fireplace, Glass doors leading out to a pergola, A family room, dining room, renovated kitchen , den or office could be a fifth bedroom. One upstairs bathroom renovated and one on the first

  Cheryl Wendling BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  133 Pomeroy 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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  /58

  $329,900

  • 5 Beds
  • 5 Baths
  • 2,976 Sq Ft

  41 Reed St, Pittsfield, MA 01201

  Spacious two family flat with great parking area and fabulous location, in proximity to bank, stores, restaurants and more downtown attractions! This home was recently renovated with improvements that include brand new natural gas high efficiency heating systems, painting and more! There are vinyl replacement windows throughout the building, and city water and sewer. The large upstairs features 3

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  41 Reed St, Pittsfield, MA 01201
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  /2

  $269,900

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

  42 John St, Pittsfield, MA 01201

  Investment Property Priced to Sell! This 2 family flat offers 4 bedrooms in each unit, vinyl siding, replacement windows, in unit laundry and separate utilities paid by tenants. Plenty of parking, private yard and right next to the park make this a lucrative addition to any investment portfolio. Both units were completely updated in 2022. Unit #44 has a certificate of lead compliance.

  Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  42 John St, Pittsfield, MA 01201
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  /2

  $10,000

  • Land
  • 0.28 Acre
  • $36,232 per Acre

  0 Beacon Ave, Pittsfield, MA 01201

  Two Land parcels located in Pittsfield within the Pittsfield School District. Zoned R-12, wetlands. Situated in an established area of the municipality. land is offered as-is.

  Alex King Lock and Key Realty, Inc

  0 Beacon Ave, Pittsfield, MA 01201
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  /29

  $279,900

  • 2 Beds
  • 1 Bath
  • 1,060 Sq Ft

  60 Churchill Crest, Pittsfield, MA 01201

  Welcome to Modern One Level Easy Living at Churchill Crest Condominiums. This unique offering has been meticulously updated and finished with new and improved features in each room. Enter spacious living room with expansive newer slider framing front to back views. Bousquet mountain out front and to rear see the rear patio, privacy, woods and beautiful custom landscape that has evolved from over

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  60 Churchill Crest, Pittsfield, MA 01201
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  /34

  $374,900

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft

  46 Lucille St, Pittsfield, MA 01201

  Inviting cape style home nestled between two of the Berkshires' most beautiful lakes- Pontoosuc and Onota set for outdoor water adventures and be surprised at home with an abundance of family spaces. Don't miss the oversized side yard a possible extra building lot (verification by buyer) for the accessory building, garage or second home. This home has three full levels of living offers

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  46 Lucille St, Pittsfield, MA 01201
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  /41

  $314,900

  • 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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  /2

  $20,000

  • Land
  • 0.25 Acre
  • $80,000 per Acre

  LOT 20 Plunkett St, Pittsfield, MA 01201

  This Residential Building lot is conveniently located within walking distance to stores, restaraunts, banks, parks, and public transportation. Lot Dimensions: 65.88' x 165'. Priced below current assessed value! Bring your vision to life in this centrally located lot!

  Mary Jane Dunlop BISHOP WEST REAL ESTATE

  LOT 20 Plunkett St, Pittsfield, MA 01201
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  /33

  $1,500,000

  • 7 Beds
  • 7.5 Baths
  • 4,000 Sq Ft

  802 State Rd, Richmond, MA 01254

  Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 11+ bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the potential to include the region's premier full-service equestrian facility (see

  Diana Bisselle William Pitt Sotheby's Int'l

  802 State Rd, Richmond, MA 01254
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  /47

  $549,000

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

  31 Saint Ann's Ave, Lenox, MA 01240

  Don't miss this unique historic property -- truly a GEM! Ready for quick rental income and perfect to enjoy as spring arrives. A wonderful second home to share with family! Imagine a short stroll to downtown Lenox for coffee, a quiet dinner, and a beautiful night at Tanglewood under the stars. Just one street from downtown and steps from St. Ann's Church, this 1,700 sq. ft. bungalow blends charm

  Audrey Matys BERKSHIRE LISTINGS

  31 Saint Ann's Ave, Lenox, MA 01240
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  /17

  $204,900

  • 4 Beds
  • 2 Baths
  • 1,496 Sq Ft

  25 Ashley St, Pittsfield, MA 01201

  Nestled in a quiet, well-established neighborhood, this dated yet full of character property offers the perfect canvas for those with vision and creativity. While the home has maintained its original charm, it presents an exciting opportunity to modernize and make it your own.The floor plan features architectural details that can be restored or updated to suit your personal style. With some TLC

  Timothy Disilva SUMMIT REALTY

  25 Ashley St, 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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  /42

  $289,900

  • 3 Beds
  • 2 Baths
  • 1,026 Sq Ft

  11 Mcallister St, Pittsfield, MA 01201

  Welcome to this super cute and spacious 3-bed, 2-bath home nestled in desirable neighborhood. Inviting layout and thoughtful updates throughout. This home perfectly balances modern comfort and classic charm. Remodeled kitchen features stylish cabinetry, stainless steel appliances, a sleek tile backsplash, and marble-look countertops. Open dining area with built-ins connects seamlessly to the

  Marc Bellora LAMACCHIA REALTY, INC

  11 Mcallister St, Pittsfield, MA 01201
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  /26

  $145,000

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  64 King St, Pittsfield, MA 01201

  This 3-bedroom, 1-bath home with a detached garage offers great potential and a convenient in-town location. Featuring a solid layout and classic floor plan, it's an excellent opportunity for buyers looking to update, customize, or invest for instant equity. The home needs cosmetic improvements, and the garage, basement, and parts of the interior contain personal property that will remain.

  Gabriela Dearstyne BISHOP WEST REAL ESTATE

  64 King St, Pittsfield, MA 01201
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  /57

  $699,900

  • 4 Beds
  • 2 Baths
  • 2,662 Sq Ft

  551 Tamarack Rd, Pittsfield, MA 01201

  Welcome to 551 Tamarack Road! A beautifully updated and maintained Cape-style home, nestled on 1.28 acres in picturesque Pittsfield, MA!This charming 4-bedroom,2-bath residence boasts a perfect blend of modern amenities and classic charm. Step inside to discover a spacious, light-filled living area, ideal for gatherings and relaxation.The eat in kitchen features contemporary finishes and ample

  Doug Collins LAMACCHIA REALTY, INC

  551 Tamarack Rd, Pittsfield, MA 01201
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  /51

  $389,900

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft

  171 Pine Grove Dr, Pittsfield, MA 01201

  Charming 3-bedroom, 2-full-bath Cape nestled in a premier location! This well-maintained home offers a full dormer, a spacious sun-filled kitchen with generous cabinet and counter space, and gleaming hardwood floors throughout. The large primary bedroom provides plenty of comfort and versatility. Enjoy added living space in the semi-finished basement--perfect for a playroom, home office, or gym.

  Michele Purcell LAMACCHIA REALTY, INC

  171 Pine Grove Dr, Pittsfield, MA 01201
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  /31

  $599,000

  • 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
• 

  

  /19

  $389,900 Open Sat 12PM - 1:30PM

  • 2 Beds
  • 2 Baths
  • 1,576 Sq Ft

  1 Rolling Hills Unit 10, Lenox, MA 01240

  Unique opportunity to own a beautifully updated condo. This inviting home offers 2 bedrooms and 2 full bathrooms, a gorgeous updated kitchen, and a finished room in the basement perfect for a home office, gym, or additional living space. Enjoy outdoor living with two porches, and note that the unit may be offered furnished for added convenience. All this nestled in the heart of the picturesque

  Michele Purcell LAMACCHIA REALTY, INC

  1 Rolling Hills Unit 10, Lenox, MA 01240
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  /34

  $849,900

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

  1335 Swamp Rd, Richmond, MA 01254

  A stunning and modern contemporary home that is MOVE IN READY. It is situated privately on 4 acres, in a wooded, tranquil setting. The home, with 3 bedrooms and 3 bathrooms, has been fully and tastefully renovated in the past 12 years. The main floor features high ceilings, abundant windows, open kitchen with soapstone counters, dining area, and living room, all with scenic wooded views; perfect

  Susan Calkins STONE HOUSE PROPERTIES, LLC

  1335 Swamp Rd, Richmond, MA 01254
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  /9

  $250,800

  • 1 Bed
  • 1 Bath
  • 1,200 Sq Ft

  71 S Church St Unit S102, Pittsfield, MA 01201

  Live in a stylish renovation of an important historical building. Spacious rooms with high ceilings, exposed beams but up to date amenities. High quality fixtures and fittings. Walk in closet. In unit washer, dryer and storage. Sunny southern exposure. Building has natural gas heating, high tech a/c. Roof deck with great views of Pittsfield and a well appointed gym. Must be seen.

  Martha Piper THE KINDERHOOK GROUP

  71 S Church St Unit S102, Pittsfield, MA 01201
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  /37

  $284,900

  • 3 Beds
  • 1.5 Baths
  • 1,320 Sq Ft

  20 Greenway St, Pittsfield, MA 01201

  Recently Renovated West End Home! Tucked away on a quiet dead-end street in Pittsfield's desirable West End, this charming 3-bedroom, 1.5-bath home has been beautifully updated and is ready to move right in. Updates include refinished hardwood floors, fresh interior paint, a fully updated kitchen and baths, and all new appliances. The home has been completely rewired, features a newer boiler, and

  Michele Purcell Lamacchia Realty, Inc.

  20 Greenway St, Pittsfield, MA 01201
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  /42

  $349,900

  • 5 Beds
  • 2.5 Baths
  • 3,030 Sq Ft

  145 Bartlett Ave, Pittsfield, MA 01201

  This beautiful home offers over 3000 feet of living space. Built in 1907 it's a perfect blend of traditional character and modern comfort. Beautiful hardwood floors and elegant crown molding Inside, you'll find five spacious bedrooms and two and a half baths. Two bedrooms on the first floor and three on the second. The large kitchen features an oversized refrigerator, gas stove, and ample space

  Lori Mickle LAMACCHIA REALTY, INC

  145 Bartlett Ave, Pittsfield, MA 01201
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  /35

  $345,000

  • 6 Beds
  • 3 Baths
  • 2,892 Sq Ft

  22 Copley Terrace, Pittsfield, MA 01201

  This inviting Colonial offers six bedrooms and three full bathrooms in a prime location near downtown Pittsfield, schools, restaurants, and all the cultural and recreational attractions the Berkshires have to offer.The first floor features a spacious kitchen, formal dining room, comfortable living room, laundry area, bonus room, and a full bath. The second floor includes four bedrooms and another

  Jose Larios LAMACCHIA REALTY, INC

  22 Copley Terrace, Pittsfield, MA 01201
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  /8

  $249,900

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft

  13 Goodrich St, Pittsfield, MA 01201

  2 family with brand new gas on demand heat baseboard on first floor

  Scott Higuera 413 REAL ESTATE

  13 Goodrich St, Pittsfield, MA 01201
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  /31

  $379,000

  • 3 Beds
  • 2 Baths
  • 1,826 Sq Ft

  82 Quirico Dr, Pittsfield, MA 01201

  Home for the holidays. Well maintained, move in ready 3-bedroom, 2 bath cape home in a desirable southeast section of Pittsfield. Close to the Lenox border, Tanglewood, shopping centers, Bousquet Ski Area and Bousquet Sport. Gas heating system, living room fireplace, first floor bedroom and oversized garage. Wood floors throughout, finished basement room with room for a workshop. Well-kept yard

  Anthony Riello LAMACCHIA REALTY, INC

  82 Quirico Dr, Pittsfield, MA 01201
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  /13

  $50,000

  • Land
  • 1 Acre
  • $50,000 per Acre

  Lot 43 Westbrook Terrace, Pittsfield, MA 01201

  Welcome to Lot 43 at the corner of Westbrook Terrace and Old Farm Lane, a prime ready-to-build homesite in one of Pittsfield's most desirable neighborhoods. This one acre lot offers the perfect blend of nature, community, and convenience. With infrastructure already in place--including sidewalks, sewer, water, natural gas, and underground electric--your vision can take shape with ease.A

  Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

  Lot 43 Westbrook Terrace, Pittsfield, MA 01201
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  /17

  $129,000

  • 3 Beds
  • 2 Baths
  • 720 Sq Ft

  1 Lakewood Dr, Pittsfield, MA 01201

  Start the new year off right with this newly remodeled 3 bedroom 1 and 3/4 bath home. Large living room with vaulted ceilings, large open eat in kitchen, with laundry conveniently located off the kitchen. Primary bedroom has a newly remodeled 3/4 bath. There is an added utility room with closets and built ins for added storage. Shed on property.

  Janet Benoit MOCKINGBIRD REAL ESTATE

  1 Lakewood Dr, Pittsfield, MA 01201
• 

  

  /23

  $215,000 New Construction

  • 3 Beds
  • 1 Bath
  • 2,552 Sq Ft

  1 Pittsfield Rd, Lenox, MA 01240

  Don't miss this rare chance to acquire and revitalize a property brimming with original character. Located on a well-traveled road with excellent visibility, this 1.25-acre lot offers endless possibilities for commercial use.Featuring a brand new roof, the property is ideal for a variety of purposes, including retail, restaurant, professional offices, etc. Inside, you'll find an abundance of

  Laiken Rapisarda LAMACCHIA REALTY, INC

  1 Pittsfield Rd, Lenox, MA 01240

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