Homes for Sale near Hillcrest Educational Foundation

• 

  

  

  /20

  $2,250

  • 3 Beds
  • 1 Bath

  144 Parkside Ave, Pittsfield, MA 01201

  Be the first to call this beautifully renovated, handicap-accessible first-floor apartment home! Designed for comfort and convenience, this spacious 3-bedroom unit features modern finishes throughout and easy, step-free living. Apartment Features: 3 spacious bedroomsHandicap-accessible first-floor layoutBrand-new luxury vinyl plank (LVP) flooring throughoutModern, updated

  Erin Vincent BISHOP WEST REAL ESTATE

  144 Parkside Ave, Pittsfield, MA 01201
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  /32

  $234,900

  $35K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,360 Sq Ft

  85 Edward Ave, Pittsfield, MA 01201

  This cherished family home is ready for it's next chapter. A welcoming front foyer opens to a spacious living room filled with natural light and featuring a classic wood-burning fireplace, seamlessly connected to a formal dining room ideal for entertaining. Beautiful hardwood floors, along with original wood molding and trim throughout add timeless character and warmth. The second floor offers

  Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

  85 Edward Ave, Pittsfield, MA 01201
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  /55

  $2,950,000

  • 7 Beds
  • 7 Baths
  • 6,232 Sq Ft

  802 State Rd, Richmond, MA 01254

  Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare colonial charm. The legendary c. 1776 estate boasts a well maintained main residence/Inn, three cottages and a great barn for entertaining. The residence/Inn features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. Its dignified presence is complemented by a dining room, entrance parlor,

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  802 State Rd, Richmond, MA 01254
• 

  

  

  /12

  $379,900

  • 6 Beds
  • 4 Baths
  • 2,944 Sq Ft

  60 Division St, Pittsfield, MA 01201

  Fantastic opportunity for investors or owner occupants! The town-house style unit would be perfect for owner occupants, as it offers plenty of space on two floors and two full baths! These units are renovated, with new flooring, cabinets, countertops, lighting, doors, and more! Pittsfield is a great location with so much to do! Enjoy hiking, shopping, shows, festivals, and more. Don't miss this

  Danielle Therrien Cameron Real Estate Group

  60 Division St, Pittsfield, MA 01201
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  /39

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft

  40 Longfellow Ave, Pittsfield, MA 01201

  Welcome to this sweet Southeast charmer, set on a corner lot that offers all the comfort and personality you desire! Step onto the adorable front porch and instantly feel at home. Inside, you'll find a convenient first-floor bedroom & full bathroom perfect for flexible living. The new dining room slider opens to a spacious deck with a screened gazebo, ideal for morning coffee or evening

  Rena Rose KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  40 Longfellow Ave, Pittsfield, MA 01201
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  /34

  $749,000

  • 2 Beds
  • 2 Baths
  • 1,044 Sq Ft

  595 Lakeway Dr, Pittsfield, MA 01201

  Discover the exceptional lakefront lifestyle in this beautifully renovated, move-in ready 2-bedroom, 2-bath residence on Onota Lake. Bathed in natural light, expansive walls of windows frame captivating water views from the living room, dining area, and kitchen, creating a seamless connection to the outdoors. A welcoming fireplace adds warmth and charm, while efficient mini-split systems provide

  Victoria Standring Lamacchia Realty, Inc. - Dalton

  595 Lakeway Dr, Pittsfield, MA 01201
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  /8

  $375,000

  • 6 Beds
  • 3 Baths
  • 3,672 Sq Ft

  98 Lincoln St, Pittsfield, MA 01201

  Turnkey 3-unit multifamily investment in Pittsfield, just minutes from downtown. Fully occupied, generating $4,173/month ($50,076/year) in gross rent from all-current tenants. Unit mix: 98A (1BR/1BA) at $1,199/mo, 98B (2BR/1BA) at $1,324/mo, and 100 (3BR/2BA) at $1,650/mo. All three units have gas heat and hot water; owner covers snow removal, landscaping, and water & sewer. 2025 operating

  Jason Saphire www.HomeZu.com

  98 Lincoln St, Pittsfield, MA 01201
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  /35

  $349,000

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  15 Lillian St, Pittsfield, MA 01201

  Welcome home to this sweet split-level in desirable Southeast Pittsfield neighborhood. Offering 3 bedrooms and 1.5 baths, this well-maintained home features a spacious, well-appointed kitchen with granite countertops, abundant cabinetry, and great functionality for everyday living. Cozy up by the wood-burning fireplace or unwind in the inviting four-season room overlooking the deck and backyard.

  Victoria Standring Lamacchia Realty, Inc. - Dalton

  15 Lillian St, Pittsfield, MA 01201
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  /2

  $299,900

  • Land
  • 6 Acres
  • $49,983 per Acre

  0 West St, Pittsfield, MA 01201

  This land is ideally located near downtown. 6 acres in a R6 zone, this has been approved for subdivision in the past. Comes with complete engineering including maps, topo's, traffic study, and much more. Beautiful views of Bousquet, bus line, all public utilities available. A RARE development opportunity to change the housing market in Pittsfield.

  Steve Ray 413 REAL ESTATE

  0 West St, Pittsfield, MA 01201
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  /2

  $155,000

  • Land
  • 5 Acres
  • $31,000 per Acre

  365 Churchill St, Pittsfield, MA 01201

  Seller is offering a 5-acre lot for separate sale from the 15-acre property. The 5-acre parcel does not include the installed electricity, driveway, or building pad, which are located on the 10-acre parcel.Also available with 15 acres MLS#248259

  Sally Carr KEY REALTY

  365 Churchill St, Pittsfield, MA 01201
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  /28

  $299,000

  • 2 Beds
  • 1 Bath
  • 528 Sq Ft

  20 Pine Rd, Richmond, MA 01254

  Just steps from the sparkling shoreline of Richmond Pond, this year-round bungalow offers relaxed Berkshire living with a touch of charm. The inviting living area centers around a cozy propane fireplace, complemented by a bright vaulted ceiling great room that's perfect for morning coffee, reading, or seasonal entertaining. Set within the vibrant Richmond Shores community, enjoy easy access to a

  William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  20 Pine Rd, Richmond, MA 01254
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  /37

  $630,000

  $50K PRICE DROP

  • 8 Beds
  • 8 Baths
  • 6,120 Sq Ft

  301 Fenn St, Pittsfield, MA 01201

  8 Unit investment opportunity! Located just outside of downtown Pittsfield and within walking distance to shops, restaurants, schools, and parks. Low maintenance exterior with loads of off street parking. All units feature one bedroom/studio setups with separate heat and electricity. Coin-op laundry located on site for additional income.

  Cory Evangelisto NOCHER REALTY

  301 Fenn St, Pittsfield, MA 01201
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  /58

  $839,900

  • 4 Beds
  • 4.5 Baths
  • 4,194 Sq Ft

  35 Meadow Ridge Dr, Pittsfield, MA 01201

  Set in a peaceful West Pittsfield neighborhood, 35 Meadow Ridge is a sophisticated contemporary home with spacious thoughtfully designed living. Soaring 12 foot ceilings and cherry hardwood floors welcome you inside. The main level features a family room with built-ins, living room with gas fireplace, dining room, eat-in kitchen and access to the outdoor deck. The second floor offers an expansive

  Molly Gillon COMPASS MASSACHUSETTS , LLC GB

  35 Meadow Ridge Dr, Pittsfield, MA 01201
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  /7

  $219,900

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  233 Cadwell Rd, Pittsfield, MA 01201

  Two-family home set on just under 1.5 acres offering the perfect blend of country living and city convenience. Each unit features decks overlooking a spacious backyard, ideal for relaxing or entertaining. Enjoy the privacy and open space while still being just minutes from city amenities, shopping, and dining. A great opportunity for owner-occupants or investors--live in one unit and rent the

  Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals

  233 Cadwell Rd, Pittsfield, MA 01201
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  /42

  $1,750,000

  • 6 Beds
  • 4.5 Baths
  • 7,894 Sq Ft

  500 Williams St, Pittsfield, MA 01201

  Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal

  Mauren White-Kirkby Berkshire Hathaway Home Services Barnbrook Realty

  500 Williams St, Pittsfield, MA 01201
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  /56

  $1,149,000

  $130K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 2,691 Sq Ft

  18 Highcrest Rd, Lenox, MA 01240

  Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly

  Suzann Ward HOUSATONIC REAL ESTATE

  18 Highcrest Rd, Lenox, MA 01240
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  /36

  $469,900

  • 4 Beds
  • 1.5 Baths
  • 2,100 Sq Ft

  30 Lexington Pkwy, Pittsfield, MA 01201

  Welcome to 30 Lexington Parkway, an exceptionally cherished home in one of Southeast Pittsfield's most coveted neighborhoods. Brimming with timeless character, warmth, and pride of ownership, this impeccably maintained 4-bedroom home blends classic charm with everyday comfort. The inviting living spaces feature a stunning fireplace, hardwood floors, spacious eat-in kitchen, screened-in porch

  Anthony Riello Lamacchia Realty, Inc. - Dalton

  30 Lexington Pkwy, Pittsfield, MA 01201
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  /69

  $939,500

  $50K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 3,823 Sq Ft

  9 Eastbrook Ln, Pittsfield, MA 01201

  Set within one of the Berkshires most coveted communities, 9 Eastbrook Lane is a masterclass in refined living, where thoughtful design meets impeccable care. Beautifully and intentionally sited, this distinguished residence offers 5 bedrooms, 3 full and 2 half baths across a gracious, light-filled layout designed for both elegant entertaining and everyday comfort.The stunning kitchen

  Victoria Standring Lamacchia Realty, Inc. - Dalton

  9 Eastbrook Ln, Pittsfield, MA 01201
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  /60

  $2,698,000

  • 5 Beds
  • 5 Baths
  • 4,581 Sq Ft

  109 Under Mountain Rd, Lenox, MA 01240

  Some homes are purchased. Others become part of a family's legacy. Welcome to 109 Under Mountain Road. There is something unmistakably special about a Berkshire summer- evening stroll to Tanglewood, morning coffee overlooking protected meadows, or relaxing on the patio as the music of the Boston Symphony Orchestra drifts softly through the evening air. Bathed in extraordinary natural light, this

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  109 Under Mountain Rd, Lenox, MA 01240
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  /13

  $249,900

  $10K PRICE INCREASE

  • 6 Beds
  • 2 Baths
  • 1,928 Sq Ft

  17 Wallace Place, Pittsfield, MA 01201

  Recently renovated two-family home offering true turnkey convenience! Both units feature brand-new kitchens and bathrooms, updated heating systems, and stylish laminated flooring throughout. With all utilities fully separated, this low-maintenance property is ideal for investors seeking a hassle-free addition to their portfolio. Whether you're expanding your investments or starting fresh, this

  Michele Purcell Lamacchia Realty, Inc.

  17 Wallace Place, Pittsfield, MA 01201
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  /44

  $789,900

  $57K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,680 Sq Ft

  63 Sherwood Dr, Lenox, MA 01240

  Don't miss this Lenox beauty tucked away on a quiet side street. Main level w hardwood flooring, living room with crown molding, formal dining w. large bay window, updated kitchen w extensive cabinetry. Family room w gas fireplace opens to large screened porch / patio. First floor laundry and 1/2 bath. Three bedrooms on the upper level; primary suite w adjoining dressing room/ primary bath with

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  63 Sherwood Dr, Lenox, MA 01240
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  /39

  $459,900

  • 8 Beds
  • 4 Baths
  • 6,640 Sq Ft

  271 Tyler St, Pittsfield, MA 01201

  Renovated 4-family home, located on a corner lot in a great location in Pittsfield. There are two units on the first floor and two units on the second floor. The upstairs units also feature additional bonus space in the finished attics. Each unit rented at $1,500/month, with tenants paying for their own heat, hot water and electricity. major updates were done in 2023-2024. This is a solid

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  271 Tyler St, Pittsfield, MA 01201
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  /21

  $195,000

  $4K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,480 Sq Ft

  57 Adam St, Pittsfield, MA 01201

  Offering an affordable path to homeownership, this property is ideal for buyers ready to trade renting for a place of their own or investors looking to expand their rental portfolio. The first floor includes an eat-in kitchen, first-floor laundry, and a flexible room for additional living space. Bring your ideas and make it your own over time. A covered back patio extends your living space

  Leanne Sedlak REAL BROKER

  57 Adam St, Pittsfield, MA 01201
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  /42

  $349,900

  • 4 Beds
  • 1.5 Baths
  • 1,668 Sq Ft

  43 State St, Pittsfield, MA 01201

  Recently renovated brick cape with attached garage, on a beautiful corner lot! The first floor offers spacious living room open to the updated large eat-in kitchen, with quartz countertops and new stainless appliances. The home has a total of 4 bedrooms and 1.5 baths. The first floor also features a renovated full bathroom and 2 bedrooms. Upstairs you will find a hat bathroom and two additional

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  43 State St, Pittsfield, MA 01201
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  /26

  $835,000

  $40K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,791 Sq Ft

  90 Hawthorne St, Lenox, MA 01240

  Beautiful historic farm house available in Lenox Massachusetts. A charming 1840s clapboard house located on the estate of ''Brookhurst'', one of the famed Berkshire ''cottages'', this formerguest house has 3 or 4 bedrooms and 2 full baths spread over three floors (primary bedroom and bath on main floor). It has a private gated driveway and an attached 2 car garage.. Luxurious traditional

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  90 Hawthorne St, Lenox, MA 01240
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  /6

  $95,000

  • Land
  • 1.61 Acres
  • $59,006 per Acre

  497 Gale Ave, Pittsfield, MA 01201

  Build Your Berkshire Dream Home: Views, Convenience, & Site Prep Complete! Immerse yourself in the tranquil beauty of the Berkshires. This exceptional property offers the perfect balance of a scenic country retreat and effortless proximity to urban convenience. Situated along a picturesque road, the gently graded, partially cleared acreage showcases sweeping mountain and pastoral views--the

  Tammy Christen KELLER WILLIAMS REALTY

  497 Gale Ave, Pittsfield, MA 01201
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  /15

  $334,500

  • 3 Beds
  • 1 Bath
  • 1,452 Sq Ft

  144 Elberon Ave, Pittsfield, MA 01201

  Welcome to 144 Elberon Ave. This home is close to Golf, Shopping, Dining, Parks, Down town and so much more yet its on a lovely side street. Three bedroom Garrison Colonial offers formal dining room, formal living room with fire place and nice den. Under the carpet you will find blond oak floors. The back yard offers nice views, a patio and hot tub. The home was converted to gas approximately 5

  Sherry Street REALTY STREET, LLC

  144 Elberon Ave, Pittsfield, MA 01201
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  /3

  $419,000

  • 7 Beds
  • 4.5 Baths
  • 4,682 Sq Ft

  312 South St, Pittsfield, MA 01201

  Four-family investment opportunity that checks all the boxes! Great location. Fully rented. Turnkey. Robust net operating income. This well-maintained home, comprising three 2-bedroom units and one 1-bedroom unit all with separate utilities, is an instant profit generator and offers real value in today's market.

  Derek Greene The Greene Realty Group

  312 South St, Pittsfield, MA 01201
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  /27

  $195,000

  • 2 Beds
  • 1 Bath
  • 540 Sq Ft

  21 Woodleigh Rd, Pittsfield, MA 01201

  Robin Moore 413 REAL ESTATE

  21 Woodleigh Rd, Pittsfield, MA 01201
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  /42

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,399 Sq Ft

  130 Oliver Ave, Pittsfield, MA 01201

  Welcome to this beautifully maintained Cape Cod-style home, built in 2001 and set on 1.13 acres. Offering 3 bedrooms and 2.5 baths, this inviting home combines charm with a thoughtfully designed floor plan that's perfect for everyday living and entertaining. The main level features a private office with elegant French doors, ideal for working from home or creating a quiet retreat. The spacious

  Lori Mickle Lamacchia Realty, Inc. - Dalton

  130 Oliver Ave, Pittsfield, MA 01201
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  /38

  $299,900

  • 5 Beds
  • 2 Baths
  • 2,690 Sq Ft

  63 Glenwood Ave, Pittsfield, MA 01201

  Charming 2-family flat offering a great opportunity for owner-occupants or investors alike! This well-maintained property features beautiful wood floors, inviting front porches, and private back decks perfect for relaxing or entertaining. Both units have separate utilities for added convenience and efficiency. The second-floor apartment includes a finished attic area providing extra living space.

  Robin Moore 413 REAL ESTATE

  63 Glenwood Ave, Pittsfield, MA 01201
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  /34

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  1228 East St, Pittsfield, MA 01201

  Welcome to 1228 East St. A longtime family home filled with warmth, character and opportunity. Beautiful hardwood floors throughout much of the home. Updates include electric panel, blown in insulation, a new oil tank 2018 and new oil burner 2022. The spacious second floor kitchen area offers potential to create a two-family flat subject to city approval. A three-car garage offers extra space for

  Anthony Riello Lamacchia Realty, Inc. - Dalton

  1228 East St, Pittsfield, MA 01201
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  /56

  $3,800,000

  $1M PRICE DROP

  • 8 Beds
  • 6.5 Baths
  • 7,494 Sq Ft

  140 Hancock Rd, Pittsfield, MA 01201

  Welcome to an extraordinary lakefront estate on the shores of Pontoosuc Lake, an offering that sets a new benchmark for luxury living in the Berkshires. With over 7,494 square feet of total space, including exceptional garage capacity ideal for car collectors or hobbyists, this remarkable property offers unparalleled scale, versatility, and setting.The main living area showcases a

  Elisha Poirier STONE HOUSE PROPERTIES, LLC

  140 Hancock Rd, Pittsfield, MA 01201
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  /56

  $899,000

  $80K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,520 Sq Ft

  4 Fawn Ln, Pittsfield, MA 01201

  Move right into this stunning single-family home at highly desirable Berkshire Country Meadows. Nearly new and impeccably maintained, this spacious home offers the ease of condominium living with the feel of a private residence. The open-concept design features a beautiful kitchen, dining area, and living room with a cozy gas fireplace, perfect for entertaining or everyday living, and a separate

  Victoria Standring Lamacchia Realty, Inc. - Dalton

  4 Fawn Ln, Pittsfield, MA 01201
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  /42

  $1,200,000

  • 4 Beds
  • 5.5 Baths
  • 3,738 Sq Ft

  8 Stoneledge Rd, Lenox, MA 01240

  Beautifully maintained home set on a private one-acre lot on a quiet cul-de-sac in one of Lenox's most desirable neighborhoods. This thoughtfully designed residence offers four bedrooms and 5.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The inviting floor plan is ideal for both everyday living and entertaining. Step outside to a beautifully landscaped

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  8 Stoneledge Rd, Lenox, MA 01240
• 

  

  /20

  $289,000

  $21K PRICE DROP Pre-Foreclosure

  • 3 Beds
  • 1 Bath
  • 1,326 Sq Ft

  77 Imperial Ave, Pittsfield, MA 01201

  Well maintained cape on a perfect corner lot in The Orchards! The home features two bedrooms, full bath, kitchen and living room all on the main level. The second floor has an additional bedroom and storage. Wood burning fireplace and mountain views from the back yard. Efficient natural gas heating and solar panels from SunRun. Basement was at one time finished and certainly could be in the

  Derek Strzepa NOCHER REALTY

  77 Imperial Ave, Pittsfield, MA 01201
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  /36

  $449,900

  Open Sat 10AM - 12PM $19K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft

  81 Northumberland Rd, Pittsfield, MA 01201

  Move in ready! New roof and gutters in 2026, maintains original details but has been thoroughly updated. Located on a quiet, tree lined street, 81 Northumberland offers the kind of lifestyle one dreams about. Imagine walking your children to the nearby elementary school, stopping in for fresh pastries at the local bakery, grabbing a coffee on the way home, or enjoying an evening stroll through

  Tanya LeRose THE KINDERHOOK GROUP

  81 Northumberland Rd, Pittsfield, MA 01201
• 

  

  /34

  $275,000

  • 5 Beds
  • 2 Baths
  • 2,158 Sq Ft

  34 Daniels Ave, Pittsfield, MA 01201

  Welcome to 34 Daniels Avenue, part of the Westside Legends Attainable Housing Program. This updated Pittsfield home offers a comfortable layout with recent improvements throughout, including new flooring, new appliances, and refreshed bathrooms. The interior feels clean, bright, and move-in ready, while still offering a practical and manageable footprint for everyday living. Conveniently located

  Samantha Homeyer BIRCH PROPERTIES

  34 Daniels Ave, Pittsfield, MA 01201
• 

  

  /39

  $389,900

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

  55 Revilla Terrace, Pittsfield, MA 01201

  Easy living in this move-in ready contemporary in southeast Pittsfield! Stylishly designed with a flexible floor plan. Enter into a light-filled living space with built-in cabinetry in the entry, spacious oversized eat-in kitchen that that opens to a large rear deck. Kitchen with quartz island/ stainless appliances. Oversized first floor bath with laundry. Additionally find a den/sleeping space

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  55 Revilla Terrace, Pittsfield, MA 01201
• 

  

  /41

  $313,900

  • 2 Beds
  • 2 Baths
  • 1,210 Sq Ft

  560 Crane Ave, Pittsfield, MA 01201

  More than meets the eye from the street view! Spacious embankment ranch welcomes you with gleaming hardwood flooring. Enter into the living room w cedar entry closet. What are YOU looking for? Here, you'll find a flexible floor plan featuring two or three bedrooms on the main floor (third bedroom off kitchen makes great formal dining option. Eat-in galley kitchen. Bonus space is the year-round

  Amanda Kmetz ROBERTS & ASSOC. REALTY, INC

  560 Crane Ave, Pittsfield, MA 01201

Showing Results 121 - 160, Page 4 of 5