Homes for Sale near Hillcrest Academy

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  /30

  $240,000

  • 3 Beds
  • 1 Bath
  • 822 Sq Ft

  63 Reuter Ave, Pittsfield, MA 01201

  Delightful Colonial nestled on a quiet street in Pittsfield's southeast neighborhood. This well-kept home blends classic charm with modern comforts, offering 3 bedrooms, 1 baths, and a spacious, functional layout. Step inside to find beautiful hardwood floors, generous natural light, and a cozy living room that opens to a formal dining space. Updated kitchen features ample cabinetry. Upstairs,

  Jeff Astore WILLIAM RAVEIS REAL ESTATE

  63 Reuter Ave, Pittsfield, MA 01201
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  /16

  $239,900

  • 5 Beds
  • 2 Baths
  • 1,768 Sq Ft

  24 Southern Ave, Pittsfield, MA 01201

  Excellent investment opportunity! This recently updated multi-family home features a 3-bedroom, 1 bathroom downstairs unit and a 2-bedroom, 1-bathroom upstairs unit. Updates include a new roof, gas furnace, radiators, drywall, electrical, and plumbing. Both kitchens and bathrooms have been fully renovated. The downstairs unit has vinyl flooring and a kitchen with granite countertops, while the

  Derek Greene The Greene Realty Group

  24 Southern Ave, Pittsfield, MA 01201
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  /25

  $619,900

  • 4 Beds
  • 2.5 Baths
  • 2,646 Sq Ft

  68 Brookside Dr, Pittsfield, MA 01201

  This terrific side hall Colonial offers a spacious, family-friendly layout with timeless appeal and effortless flow. The heart of the home is the large, updated kitchen featuring stone countertops and a sunny dining area, ideal for everyday living and entertaining.Gracious first-floor spaces include a step-down family room with a wood-burning fireplace, built-ins, and gleaming hardwood floors, as

  Kathleen Quinn WILLIAM PITT SOTHEBY'S - LENOX

  68 Brookside Dr, Pittsfield, MA 01201
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  /14

  $1,475,000

  • 16 Beds
  • 16 Baths
  • 8,608 Sq Ft

  14 Highland Ave, Pittsfield, MA 01201

  Excellent 8-Unit Investment Opportunity-5 minute walk to the Lake!Clean, well-maintained multifamily property featuring 8 total units with separate utilities. Each unit includes central A/C. Property offers private, dedicated parking for tenants. Prime location--just minutes from major hospitals, large employers, shopping, and public transit. High-demand rental area with strong occupancy history.

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  14 Highland Ave, Pittsfield, MA 01201
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  /16

  $185,000

  • 1 Bed
  • 1.5 Baths
  • 1,056 Sq Ft

  26 Churchill Crest, Pittsfield, MA 01201

  Welcome to this inviting one-bedroom condo nestled in the desirable Churchill Crest Condominium Association. Perfectly located just minutes from Pittsfield State Forest, downtown Pittsfield, and some of the area's top cultural attractions, including Tanglewood, The Colonial Theatre, and Barrington Stage Company.This thoughtfully designed home features a spacious living room with a wood-burning

  Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

  26 Churchill Crest, Pittsfield, MA 01201
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  /46

  $390,000

  • 6 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  36 Chickering St, Pittsfield, MA 01201

  Charming Duplex in Southeast Pittsfield - Great Investment Opportunity!Welcome to this well-maintained duplex nestled in a desirable Southeast Pittsfield neighborhood! The layout on both sides includes a living room, dining room, large kitchen, and three comfortably sized bedrooms. Unit #38 has one bath and laundry hook-ups in the basement, while Unit #36 has 1.5 baths and laundry hook-ups on the

  Chris LaPatin LAMACCHIA REALTY, INC

  36 Chickering St, Pittsfield, MA 01201
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  /49

  $369,900

  • 2 Beds
  • 2 Baths
  • 1,557 Sq Ft

  55 Revilla Terrace, Pittsfield, MA 01201

  Move-in ready New Construction in Southeast Pittsfield! This lovely home blends style, sophistication, function, efficiency & LOCATION! Enjoy an amazing kitchen, boasting an oversized quartz island, 2 stunning full bathrooms with high-end finishes, gleaming wood floors, large deck and FULLY Finished lower level with full walkout. This multi functional lower level space offers so many

  Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  55 Revilla Terrace, Pittsfield, MA 01201
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  /14

  $219,000

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  260 Pittsfield Rd Unit B-5, Lenox, MA 01240

  Freshly updated 1 BR/1 BA condo at Lenox Heights. This light‑filled, 800 sq ft condo boasts athoughtfully renovated kitchen with new cabinetry and stainless‑steel appliances, plus plushwall‑to‑wall carpeting for a fresh, clean aesthetic. Step outside onto your private balcony toenjoy your morning coffee. On‑site amenities include an outdoor pool, tennis courts, and

  Samantha Homeyer BIRCH PROPERTIES

  260 Pittsfield Rd Unit B-5, Lenox, MA 01240
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  /20

  $189,900

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  33 Maplewood Ave Unit 305, Pittsfield, MA 01201

  Welcome to historic Maplewood Condominiums--Owner is offering to pay full second year assessment and $10,000 towards final year assessment for anyone attending the open house on Sunday imeless architecture, modern comfort, and a prime location come together in one of Pittsfield's most desirable residential buildings.The top-floor, corner unit offers hard wood floors with natural light and a

  Cheryl Ryan BISHOP WEST REAL ESTATE

  33 Maplewood Ave Unit 305, Pittsfield, MA 01201
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  /13

  $257,000

  • 1 Bed
  • 1 Bath
  • 709 Sq Ft

  3 Morgan Manor Unit 3 - 8, Lenox, MA 01240

  Welcome to 3‑8 Morgan Manor, a charming one-bedroom condo nestled in the heart of Lenox Village. This move-in-ready unit offers a sunlit layout with cozy carpeting, and efficient space. The condo fee includes heat, hot water, gas, water, and sewer, making for truly hassle-free living. Located in a well-maintained building just steps from downtown Lenox, you'll enjoy easy access to

  Katie Soules WILLIAM RAVEIS REAL ESTATE

  3 Morgan Manor Unit 3 - 8, Lenox, MA 01240
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  /36

  $289,000

  • 3 Beds
  • 1 Bath
  • 1,449 Sq Ft

  24 Lebanon Ave, Pittsfield, MA 01201

  Welcome home to your contemporary abode perched atop a hill, offering a serene retreat with a modern twist. This 3-bedroom, 1-bath residence is a treasure trove of unique features, designed for those who appreciate style and functionality.Upon entering, the open living and dining area invites you to envision life here, where natural light and space create an inviting atmosphere. The sunken eat-in

  Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX

  24 Lebanon Ave, Pittsfield, MA 01201
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  /26

  $249,900

  • 2 Beds
  • 2 Baths
  • 1,227 Sq Ft

  44 Churchill Crest Unit 44, Pittsfield, MA 01201

  Exceptionally maintained two bedroom and two bathroom condo. An end unit located in Churchill Crest Condominium Association that offers exterior maintenance, cable/internet, and a heated pool with pavilion. Boasting a spacious living room with a wood burning fireplace, hardwood floors, and a private balcony. Leading into a formal dining room off the kitchen with a breakfast bar and ample cabinets

  Cory Evangelisto NOCHER REALTY

  44 Churchill Crest Unit 44, Pittsfield, MA 01201
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  /22

  $79,900

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  34 Lakewood Cir, Pittsfield, MA 01201

  Come see the possibilities!Opportunity awaits in this 980 sq. ft. mobile home, ready for your finishing touches! Featuring a newer roof and all new plumbing throughout, the major updates are already in place. A nice front deck welcomes you into the property, offering a great space to relax and enjoy the outdoors. With solid potential and a head start on improvements, this home is perfect for

  Sara Bresett NOCHER REALTY

  34 Lakewood Cir, Pittsfield, MA 01201
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  /38

  $404,900

  • 4 Beds
  • 2 Baths
  • 1,918 Sq Ft

  16 Revere Pkwy, Pittsfield, MA 01201

  The Parkway neighborhoods of southeast Pittsfield are among the city's most sought-after, prized for their tree-lined streets, classic architecture, and easy access to downtown, parks, and schools. Built in 1930, this well-maintained 4 bedroom, 2 bath home provides everything your family needs, with plenty of space for everyone. The first floor features a large living room, east-facing with

  Stephen Daoust STONE HOUSE PROPERTIES, LLC

  16 Revere Pkwy, Pittsfield, MA 01201
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  /25

  $579,900

  • 3 Beds
  • 4.5 Baths
  • 5,640 Sq Ft

  168 Elm St, Pittsfield, MA 01201

  Welcome to this exceptional mixed-use building that combines residential and commercial opportunities in one of the most sought after areas in Pittsfield .This property features 3 great apartments and two storefronts, making it ideal for investors or entrepreneurs looking to capitalize on a vibrant local community. The building offers 3 one bedroom apartments, 2 units will be delivered empty for

  Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  168 Elm St, Pittsfield, MA 01201
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  /18

  $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, additional family room on the lower level and newer appliances. Enjoy the Tennis/pickle ball courts or take swim

  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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  /38

  $875,000

  • 18,000 Sq Ft

  40 Pecks Rd, Pittsfield, MA 01201

  Don’t be late for this redevelopment opportunity! 18,000 Sqft on 1.1 Acres. Structurally sound property offers a rare opportunity to transform a historic space into a vibrant new community. Preliminary estimates suggest the potential for 12 residential units, with ample room for parking and green space. Featuring solid brick construction. Expansive windows, high ceilings, and open floor plans,

  Xavier Cruz Fathom Realty

  40 Pecks Rd, Pittsfield, MA 01201
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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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  /12

  $175,000

  • 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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  /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

  $49,500

  • Land
  • 0.25 Acre
  • $198,000 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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  /70

  $1,100,000

  • 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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  /46

  $399,000

  • 4 Beds
  • 2 Baths
  • 2,015 Sq Ft

  149 Fort Hill Ave, Pittsfield, MA 01201

  Embrace countryside tranquility in this 4-bedroom, 2-bath home that blends rustic charm with modern amenities. Nestled in serenity, this property is the perfect retreat for those seeking peace without sacrificing convenience.As you step through the front door, the welcoming atmosphere of this country home envelops you. The living spaces are bathed in natural light, highlighting the comfortable

  Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX

  149 Fort Hill Ave, Pittsfield, MA 01201
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  /38

  $710,000

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

  51 New Lenox Rd, Lenox, MA 01240

  Meticulous craftsmanship and timber frame construction define this charming Colonial Dutch gambrel residence, combining comfort and practicality for everyday living. High-grade timber framing and solid construction give this home character and a warm, inviting atmosphere with its wood accents.Gather around the stone fireplace in the inviting living room, or whip up meals in the kitchen equipped

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  51 New Lenox Rd, Lenox, MA 01240
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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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  /48

  $989,000

  • 4 Beds
  • 2.5 Baths
  • 2,576 Sq Ft

  144 Shore Rd, Richmond, MA 01254

  WATERFRONT home on Richmond Pond. With 65' of frontage and over half an acre, this charming four season home has 4 bedrooms, 2 1/2 bathrooms and wonderful outdoor living areas. Gorgeous perennial gardens, a spacious patio off the kitchen/great room, fire pit, dock,and a rear garage door (perfect for boat access and storage) all while enjoying the beautiful lake views.. Once inside is a

  Lori Rose STONE HOUSE PROPERTIES, LLC

  144 Shore Rd, Richmond, MA 01254
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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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  /25

  $160,000

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

  94 John St, Pittsfield, MA 01201

  $20K PRICE REDUCTION. 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

  $310,000

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

  50 W Housatonic St, Pittsfield, MA 01201

  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

  50 W Housatonic 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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  /12

  $189,900

  • 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 in 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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  /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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  /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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  /39

  $565,900

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

  144 Bromback St, Pittsfield, MA 01201

  Beautiful, spacious 8 bedroom, 3 updated bath, 4000 sq ft home, custom built and nestled between 2 lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota lake in approximately 10 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, swimming, picnicking and more. Enjoy the convenience of two laundry rooms and two updated

  Janet Benoit Janet L. Benoit

  144 Bromback St, 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

  $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
• 

  

  /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

Showing Results 81 - 120, Page 3 of 5