Homes for Sale near Hillcrest Academy

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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
• 

  

  

  /25

  $195,000

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

  94 John St, Pittsfield, MA 01201

  This home is move in condition with many upgrades and improvements. Including a large eat in kitchen with new cabinets counters and flooring. Updates 1st floor 1/2 bath includes washer and dryer. Large open living room, newer carpet. Quaint den/office off living room. 2nd floor offering updated full bath with tub/shower surround. 2 generous sized bedrooms with walk in closet in each room. Need

  Barbara DeMers NOCHER REALTY

  94 John St, Pittsfield, MA 01201
• 

  

  

  /3

  $325,000

  • 5 Beds
  • 3 Baths
  • 5,392 Sq Ft

  Unlisted Address

  An outstanding opportunity to acquire a well-maintained multi-unit property in the heart of Pittsfield's vibrant Downtown Cultural District. This property features spacious residential units, ideal for attracting & retaining long-term tenants.Recent upgrades include newer siding and high-efficiency natural gas system. The third unit, formerly a commercial storefront, offers excellent potential to

  Heather Gallagher JAN PERRY REALTY & ASSOCIATES, LLC

  Unlisted Address
• 

  

  

  /50

  $364,000

  • 3 Beds
  • 2 Baths
  • 1,457 Sq Ft

  184 Mcintosh Dr, Pittsfield, MA 01201

  New listing in The Orchards, southeast Pittsfield offers 6 rooms, 3 bedrooms, 2 full baths, hardwood floors, gas fireplace with remote, and more. Family room in lower level and full bath with heated floor. Large, lovely kitchen with large dining area. Lighting and USB ports under kitchen cabinets. All appliances remain for the buyer's enjoyment. Central air conditioning in part of the house in

  Mark Harris SIGNATURE ASSOCIATES

  184 Mcintosh Dr, Pittsfield, MA 01201
• 

  

  

  /30

  $349,000

  • 3 Beds
  • 1 Bath
  • 1,272 Sq Ft

  11 Leslie Dr, Pittsfield, MA 01201

  Enjoy this charming & move in ready cape home, with stylish finishes, & private backyard, abutting 130 acres of conservation land, nestled on almost one acre! This home features beautiful flooring & trim work throughout. The kitchen is open to a bright, yet cozy sunroom with vaulted ceilings, with access to the screened in porch overlooking the patio & gardens. The kitchen features room for a

  Laiken Rapisarda Lamacchia Realty, Inc.

  11 Leslie Dr, 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

  $195,000

  • 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

  $199,000

  • 2 Beds
  • 1,002 Sq Ft

  105 Crane Ave, Pittsfield, MA 01201

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

  Maria Liccardi LAMACCHIA REALTY, INC

  105 Crane Ave, Pittsfield, MA 01201
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  /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
• 

  

  /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
• 

  

  /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
• 

  

  /20

  $269,000

  • 4 Beds
  • 3 Baths
  • 2,460 Sq Ft

  39 Pomeroy Ave, Pittsfield, MA 01201

  Great opportunity to own a fully rented 3-family property in a central Pittsfield location, close to downtown, schools, restaurants, and local attractions. This property features two 2-bedroom units and one 1-bedroom unit, each with natural gas heat, separate electric meters, laundry hookups, and off-street parking.One unit has been fully renovated and is currently used as a successful short-term

  THE KAHN TEAM BISHOP WEST REAL ESTATE

  39 Pomeroy Ave, Pittsfield, MA 01201
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  /66

  $2,250,000

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

  1030 West St, Pittsfield, MA 01201

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

  Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

  1030 West St, Pittsfield, MA 01201
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  /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

  $675,000

  • 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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  /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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  /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
• 

  

  /22

  $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 farmhouse thoughtfully renovated for today's lifestyle. This charming 4-bedroom, 2-bathroom home is nestled on nearly 2 acres in Pittsfield, offering easy 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. Enjoy modern

  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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  /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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  /43

  $400,000

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  20 Marshall Ave, Pittsfield, MA 01201

  Welcome to this spacious and inviting 2,800 sq ft Colonial, nestled in the heart of southeast Pittsfield. This beautiful home blends classic charm with modern convenience, offering generous living spaces and a thoughtful layout, perfect for today's lifestyle. The first floor features a welcoming living room with fireplace, a formal dining room ideal for entertaining, and a conveniently located

  Chris LaPatin LAMACCHIA REALTY, INC

  20 Marshall Ave, Pittsfield, MA 01201
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  /45

  $1,245,000

  • 4 Beds
  • 4.5 Baths
  • 2,995 Sq Ft

  4 Stoneledge Rd, Lenox, MA 01240

  Charming Lenox contemporary cape on 1 acre. Located in an area of fine homes, this 4 bedroom 4.5 bath home has the following amenities: Screen porch, eat in kitchen with island, family room with fireplace, primary bedroom suite on the main floor, dining room, den, attached two car garage, finished lower level ...great space office or exercise area... natural gas heat, central air, town water

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  4 Stoneledge Rd, Lenox, MA 01240
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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
• 

  

  /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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  /14

  $399,900

  • 2 Beds
  • 1 Bath
  • 1,036 Sq Ft

  129 Shore Rd, Richmond, MA 01254

  Welcome to this cozy cottage with peek-a-view of Richmond Pond--an ideal retreat for comfort and nature lovers. Just across from the pond, enjoy a peaceful setting and water views. The bright, open living area is perfect for relaxing. The updated kitchen makes meal prep easy and includes quartz countertops. Two bedrooms offer restful retreats. Situated on one of the more spacious lots on the pond

  Kathleen Quinn WILLIAM PITT SOTHEBY'S - LENOX

  129 Shore Rd, Richmond, MA 01254
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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
• 

  

  /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
• 

  

  /20

  $224,900

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /37

  $525,000

  • 4 Beds
  • 2.5 Baths
  • 2,102 Sq Ft

  92 Leroi Dr, Pittsfield, MA 01201

  This meticulously maintained Colonial sits on a generous half-acre lot in one of Pittsfield's most sought-after neighborhoods. You're going to love hosting family and friends in the custom kitchen, complete with an island and breakfast bar that opens seamlessly into the dining room. The spacious living room is ideal for entertaining, while the bonus room and sun porch offer cozy spots for

  Andrew Manns LAMACCHIA REALTY, INC

  92 Leroi Dr, Pittsfield, MA 01201

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