Homes for Sale near Hillcrest Educational Foundation

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  /33

  $229,900

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft

  13 Oswald Ave, Pittsfield, MA 01201

  Delightful three-bedroom, one-bathroom bungalow located off West Housatonic Street in Pittsfield. This charming home features hardwood floors throughout. Enjoy the open concept layout with a dining room flowing into the livingroom. The main floor has two cozy bedrooms and a conveniently located bathroom. Ascend through one of the bedrooms to discover a unique third-floor open bedroom. Outside,

  Mariah Worth LAMACCHIA REALTY, INC

  13 Oswald Ave, Pittsfield, MA 01201
• 

  

  

  /5

  $79,900

  • Land
  • 1.08 Acres
  • $73,981 per Acre

  Lot 144 Eastbrook Ln, Pittsfield, MA 01201

  Nestled on a quiet street among upscale homes, this 1.08-acre lot offers a prime setting to build your custom residence. Underground utilities are available at the road for a seamless start. Enjoy the privacy and natural beauty of the Berkshires with easy access to downtown Pittsfield, Tanglewood, hiking trails, and more. Protective covenants preserve the integrity and lasting value of this

  Corey Bishop BISHOP WEST REAL ESTATE

  Lot 144 Eastbrook Ln, Pittsfield, MA 01201
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  /4

  $79,900

  • Land
  • 1.23 Acres
  • $64,959 per Acre

  Lot 140 Westbrook Terrace, Pittsfield, MA 01201

  Nestled on a quiet street among upscale homes, this 1.23-acre lot offers a prime setting to build your custom residence. Underground utilities are available at the road for a seamless start. Enjoy the privacy and natural beauty of the Berkshires with easy access to downtown Pittsfield, Tanglewood, hiking trails, and more. Protective covenants preserve the integrity and lasting value of this

  Corey Bishop BISHOP WEST REAL ESTATE

  Lot 140 Westbrook Terrace, Pittsfield, MA 01201
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  /57

  $245,000

  • 3 Beds
  • 1.5 Baths
  • 1,696 Sq Ft

  77 King St, Pittsfield, MA 01201

  Inviting 3-bedroom, 1.5-bath home on a generous lot with a spacious yard. Move-in ready with major upgrades completed in 2025, including a partial roof, water heater, mini-split systems for efficient heating/cooling, and updated electrical. The kitchen has been refreshed with refaced cabinets, updated fixtures, new flooring, brand new appliances and a laundry area for convenience. Full of

  Patricia Molina CENTURY 21 NORTHEAST

  77 King St, Pittsfield, MA 01201
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  /26

  $234,900

  • 3 Beds
  • 1 Bath
  • 1,366 Sq Ft

  26 Highlawn Dr, Pittsfield, MA 01201

  Needs Paint! This adorable and affordable ranch-style home features vinyl siding, replacement windows, NEW heating system, New hot water and SO MUCH POTENTIAL! Enjoy this lovely flat yard just in time for summer! This home had an operational second bath in the basement that offers the possibility of renovating it back to life! A rare find in a FANTASTIC area! Call your friends, order the

  Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  26 Highlawn Dr, 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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  /18

  $294,888

  • 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

  $2,200,000

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

  20 E Dugway Rd, Lenox, MA 01240

  Endless Potential centrally located in Lenox- 36 Acres with Dual Residences. A rare opportunity awaits in the beautiful Berkshires: 36 acres of prime Lenox land with development potential, just minutes from downtown, Tanglewood, and all the cultural and natural attractions the area has to offer. This unique property includes two existing homes, offering immediate income possibilities or a place

  Tanya Shepardson LAMACCHIA REALTY, INC

  20 E Dugway Rd, Lenox, MA 01240
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  /32

  $399,000

  • 4 Beds
  • 2 Baths
  • 1,704 Sq Ft

  207 S Mountain Rd, Pittsfield, MA 01201

  A picture-perfect 1880s farmhouse thoughtfully renovated for today's lifestyle. This charming 4-bedroom, 2-bathroom home is nestled on nearly 2 peaceful acres in Pittsfield, offering effortless access to all the cultural, natural, and recreational attractions of the Berkshires.The home has been fully updated in the past 3 years with new siding, windows, flooring, electrical and a newer roof.

  Molly Gillon COMPASS MASSACHUSETTS , LLC GB

  207 S Mountain Rd, Pittsfield, MA 01201
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  /27

  $265,000

  • 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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  /43

  $215,000

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft

  42 Briggs Ave, Pittsfield, MA 01201

  This spacious colonial-style home offers classic charm. When you enter the home, you will be greeted by the inviting front porch which makes a great mudroom. The first floor features a living room, formal dining room, kitchen, and full bathroom for convenience and guests. Upstairs, you'll find three bedrooms and a second full bathroom The walk-up attic offers ample space for storage. Outside you

  Jessica Rizzo LAMACCHIA REALTY, INC

  42 Briggs Ave, Pittsfield, MA 01201
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  /37

  $364,900

  • 4 Beds
  • 2 Baths
  • 1,919 Sq Ft

  881 Holmes Rd, Pittsfield, MA 01201

  Enjoy beautiful mountain views from this spacious 4-bedroom, 2-bath Pittsfield split-level on Holmes Road. Featuring a bright open layout, large picture windows, and fresh interior updates, this home offers a flexible floor plan with generous living space. The lower level includes space ideal for a home office or family room. Enjoy outdoor living on the rear deck and a large private yard. With a

  Ed Rich BISHOP WEST REAL ESTATE

  881 Holmes Rd, 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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  /61

  $1,650,000

  • 4 Beds
  • 2.5 Baths
  • 4,049 Sq Ft

  38 Taconic Ave, Lenox, MA 01240

  Here is your VERY rare opportunity to own a truly gracious in-town Lenox Victorian. With every inch of this lovely residence meticulously updated, the attention to detail and quality craftsmanship evident throughout ensures the ideal blend of aesthetics and modern day convenience.From the stunning entry foyer, to two front parlors, to the grand dining room and expansive wet bar, you will find

  Anne Meczywor ROBERTS & ASSOC. REALTY, INC

  38 Taconic Ave, Lenox, MA 01240
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  /40

  $379,900

  • 3 Beds
  • 2.5 Baths
  • 1,623 Sq Ft

  11 Laflin Terrace, Pittsfield, MA 01201

  Tucked away on an oversized lot, on a dead-end street, this southeast colonial has so much to offer! The charm of yesteryear meets the conveniences of today. You'll be welcomed into the open foyer and see gleaming hardwood floors throughout. The living room features a fireplace and opens to an enchanting private screened porch surrounded by lush landscape for ultimate privacy! Formal

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  11 Laflin Terrace, Pittsfield, MA 01201
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  /38

  $609,900

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

  25 Alpine Trail, Pittsfield, MA 01201

  Nestled in the desirable Pines at Bousquet community, this stunning three-story condo offers 5 spacious bedrooms and 4.5 bathrooms. The inviting eat-in kitchen flows seamlessly into a generous living room, complete with a cozy gas fireplace--perfect for relaxing or entertaining.Take in breathtaking views from either the screened porch or the lower-level patio. Located close to year-round

  Jesse Dimitropolis BISHOP WEST REAL ESTATE

  25 Alpine Trail, Pittsfield, MA 01201
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  /30

  $295,000

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  26 Davis St, Pittsfield, MA 01201

  Be sure to check out this newly renovated cute house in 1/2 an acre in Pittsfield! Centered near everything - it's so private you'd think you lived out in the woods!New Roof, Windows, Kitchen, bathroom, new flooring, new decks front and back!This home also features a large detached garage. According to the building commissioner, as it's a pre-existing building, it can be easily converted to an

  Kolleen Schmitt BISHOP WEST REAL ESTATE

  26 Davis St, Pittsfield, MA 01201
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  /53

  $1,100,000

  • 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

  $299,000

  • 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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  /32

  $340,000

  • 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, new roof, 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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  /69

  $565,900

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

  144 Brombach St, Pittsfield, MA 01201

  Beautiful, spacious 8 bedroom, 3 updated bath, 4000+sf home, custom built and nestled between two lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota Lake in approximately 9 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, fishing, swimming, picnicking and more. Enjoy the convenience of 2 laundry rooms and two updated

  Darcy Reid MOCKINGBIRD REAL ESTATE

  144 Brombach St, Pittsfield, MA 01201
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  /20

  $239,900

  • 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
• 

  

  /39

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,747 Sq Ft

  70 Saratoga Dr, Pittsfield, MA 01201

  Perfectly positioned at the head of a quiet cul-de-sac in southeast Pittsfield, 70 Saratoga Drive is a 3+ bedroom, 2.5-bath ranch brimming with potential and showcasing the kind of long view that rarely comes available, and whose value can't be overstated.This home exudes mid-century character throughout, from its natural woodwork and hardwood floors to the very spacious fireplaced living room

  Nick Geranios WILLIAM PITT SOTHEBY'S - LENOX

  70 Saratoga Dr, Pittsfield, MA 01201
• 

  

  /54

  $585,000

  • 5 Beds
  • 6 Baths
  • 8,360 Sq Ft

  36 & 40 Maplewood Ave, Pittsfield, MA 01201

  Prime Downtown Creative District Opportunity: Iconic Commercial Property + Updated Two-Family!An exceptional offering in the heart of Pittsfield's vibrant Downtown Creative District, this property, sold as a package, pairs an iconic commercial building with a spacious two-family residence. The commercial property is a landmark with natural gas heating, central air conditioning, and a walk-up

  Nick Geranios WILLIAM PITT SOTHEBY'S - LENOX

  36 & 40 Maplewood Ave, Pittsfield, MA 01201
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  /41

  $989,000

  • 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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  /7

  $179,900

  • 4 Beds
  • 2 Baths
  • 1,664 Sq Ft

  39 Hull Ave, Pittsfield, MA 01201

  Welcome to 39 Hull Ave in Pittsfield, MA! This spacious 4-bedroom, 2-bath home offers 1,664 sq ft of living space on a 0.14-acre lot, excellent for families or anyone looking for extra room. Recent updates include new windows, a roof that's only 5 years old, and a heating system installed just 3 years ago—giving you peace of mind and added value. Inside, you’ll find a comfortable layout with

  Derek Greene The Greene Realty Group

  39 Hull Ave, Pittsfield, MA 01201
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  /6

  $290,000

  • 4 Beds
  • 2 Baths
  • 1,986 Sq Ft

  249 Pittsfield Rd, Lenox, MA 01240

  Opportunity knocks in the Berkshires! This 3-acre gem on scenic Route 7 in Lenox offers a rare blend of space, potential, and prime location. Nestled among mature trees and open land, the property features a 1,986 sq ft farmhouse-style home waiting to be restored to its former glory.With residential and commercial zoning, two curb cuts, and access to natural gas, public water, and public sewer,

  Jessie Downer LAMACCHIA REALTY, INC

  249 Pittsfield Rd, Lenox, MA 01240
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  /52

  $289,000

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

  95 Oak Hill Rd, Pittsfield, MA 01201

  Imagine yourself enjoying the best of both worlds - the 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

  Mark Harris SIGNATURE ASSOCIATES

  95 Oak Hill Rd, 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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  /37

  $729,000

  • 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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  /32

  $326,000

  • 3 Beds
  • 2 Baths
  • 1,771 Sq Ft

  10 Cardinal St, Pittsfield, MA 01201

  This spacious home features 3 bedrooms and 2 full bathrooms and boasts an enclosed front porch, a den, an office, and abundant closet space. The kitchen is generously sized, and the separate dining room seamlessly connects to a side deck. You'll love the extra-large living room that provides plenty of space for relaxation and entertainment.The property is partially fenced and includes a 2-car

  Susan Deacon RE/MAX COMPASS

  10 Cardinal St, Pittsfield, MA 01201
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  /7

  $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. Can

  Xavier Cruz Fathom Realty

  48 Brown St, 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
• 

  

  /19

  $295,000

  • 2 Beds
  • 1.5 Baths
  • 1,444 Sq Ft

  33 Churchill Crest Unit 33, Pittsfield, MA 01201

  This charming condo is a must-see! Not only for its charm but also its efficiency - all new windows and mini splits have been added to off-set the heat and add A/C. These improvements set this condo apart from all others. Featuring two spacious bedrooms, one full bathroom, an additional half bathroom and laundry closet. The great room boasts of a vaulted ceiling, cozy wood-burning fireplace and a

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  33 Churchill Crest Unit 33, Pittsfield, MA 01201
• 

  

  /44

  $579,000

  • 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
• 

  

  /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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