Berkshire, MA Homes

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  /33

  $299,900 Under Contract

  • 4 Beds
  • 1 Bath
  • 1,170 Sq Ft

  1990 East St, Pittsfield, MA 01201

  Welcome home to this inviting 4-bedroom Cape at 1990 East in Pittsfield. This charming residence offers a warm, sun-filled layout with an updated kitchen and bath that combine comfort and modern style. A brand-new deck expands your living space outdoors, creating a perfect spot for morning coffee, casual dinners, or simply unwinding at the end of the day. Thoughtfully maintained and ready to

  

  John Ciepiela

  BISHOP WEST REAL ESTATE

  (413) 486-5886

  1990 East St, Pittsfield, MA 01201
• 

  

  

  /6

  $950 per month

  • 0.5 Baths
  • 500 Sq Ft
  • Property for Rent

  644 North St, Pittsfield, MA 01201

  Welcome to your new business location at 644 North Street in the vibrant city of Pittsfield, Massachusetts! This prime first-floor retail/office space offers an exceptional opportunity to establish your presence in a bustling commercial district. This space is ideally suited for a boutique shop, professional office, or any other entrepreneurial venture you envision. Its location on a busy main

  

  Syrah Bradley

  BISHOP WEST REAL ESTATE

  (413) 553-1142

  644 North St, Pittsfield, MA 01201
• 

  

  

  /22

  $325,000 Sold May 16, 2025

  56 Kenwood St, Pittsfield, MA 01201

  • 3 Beds
  • 2 Baths
  • 1,587 Sq Ft
  • Built 1929

  Last Sold Summary

  • $205/SF
  • 4 Days On Market

  Current Estimated Value $328,114

  Last Listing Agent Henry Hagenah OCTOBER MOUNTAIN REAL ESTATE

  56 Kenwood St, Pittsfield, MA 01201
• 

  

  

  /53

  Est $342,078 Not Listed For Sale

  50 Hungerford St, Pittsfield, MA 01201

  • 5 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1915

  50 Hungerford St, Pittsfield, MA 01201

  Last Sold Summary

  • 8% Above List Price
  • $172/SF
  • 72 Days On Market

  Last Sold Price $317,000

  Last Listing Agent John Segalla HOUSATONIC REAL ESTATE
• 

  

  

  /40

  $325,000 Pending

  • 12 Beds
  • 3.5 Baths
  • 4,215 Sq Ft

  292 West St, Pittsfield, MA 01201

  This large residential property offers exceptional income potential in a strong Pittsfield rental market. With 12 bedrooms and 3.5 bathrooms, it supports high-capacity occupancy and steady cash flow. The full basement provides extensive storage and includes areas where two former bathrooms once existed, offering a foundation for future updates. A full standing attic adds valuable expansion

  

  Gary Fuls Jr

  RE/MAX TRANSITIONS

  (413) 884-5511

  292 West St, Pittsfield, MA 01201
• 

  

  /12

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 776 Sq Ft
  • Condo for Rent

  30 Danforth Ave Unit 2, Pittsfield, MA 01201

  Updated 2 Bedroom 1 Bathroom. All Rooms Freshly Painted. New Kitchen Appliances: Refrigerator, Range, Stove. Bathroom Updated with New Vanity and Toilet. Use of SeparateWasher and Dryer for each unit in Basement. Extra Space for Storage in Basement. Plenty of Parking. Large Yard. East to Show!

  

  Dawn Bongiorno

  NON-MEMBER / RECIPROCAL

  (413) 366-3447

  30 Danforth Ave Unit 2, Pittsfield, MA 01201
• 

  

  /25

  $145,000 Sold May 01, 2025

  89 Orchard St, Pittsfield, MA 01201

  • 9 Beds
  • 4.5 Baths
  • 3,796 Sq Ft
  • Built 1900

  Last Sold Summary

  • 19% Below List Price
  • $38/SF
  • 81 Days On Market

  Current Estimated Value $154,326

  Last Listing Agent Christian Garner NOCHER REALTY

  89 Orchard St, Pittsfield, MA 01201
• 

  

  /49

  Est $677,845 Not Listed For Sale

  32 Brunswick St, Pittsfield, MA 01201

  • 4 Beds
  • 2.5 Baths
  • 2,386 Sq Ft
  • Built 1926

  32 Brunswick St, Pittsfield, MA 01201

  Last Sold Summary

  • 4% Above List Price
  • $274/SF
  • 4 Days On Market

  Last Sold Price $654,000

  Last Listing Agent Thom Garvey William Pitt
• 

  

  /39

  $325,000 Pending

  • 12 Beds
  • 3.5 Baths
  • 4,215 Sq Ft

  292 West St, Out-Of State, MA 99999

  This large residential property offers exceptional income potential in a strong Pittsfield rental market. With 12 bedrooms and 3.5 bathrooms, it supports high-capacity occupancy and steady cash flow. The full basement provides extensive storage and includes areas where two former bathrooms once existed, offering a foundation for future updates. A full standing attic adds valuable expansion

  

  Gary Fuls Jr

  Gary L Fuls DBA Re/MAX Transit

  (888) 256-3119

  292 West St, Out-Of State, MA 99999
• 

  

  /20

  $1,082 plus fees

  Lenox Schoolhouse Apartments

  Studio

  109 Housatonic St, Lenox, MA 01240

  Welcome to Lenox Schoolhouse Apartments — newly renovated apartment living in the heart of the Berkshires. Offering thoughtfully updated studio and one-bedroom apartment homes, this charming community combines historic character with modern comfort in a highly walkable Lenox location. Each apartment features spacious open layouts, brand-new interiors, plush carpeting, sun-filled windows, and

  109 Housatonic St, Lenox, MA 01240
• 

  

  /31

  $318,000 Sold Jul 30, 2025

  135 Imperial Ave, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 1,252 Sq Ft
  • Built 1959

  Last Sold Summary

  • 6% Above List Price
  • $254/SF
  • 16 Days On Market

  Current Estimated Value $323,153

  Last Listing Agent Doug Collins LAMACCHIA REALTY, INC

  135 Imperial Ave, Pittsfield, MA 01201
• 

  

  /26

  Est $264,816 Not Listed For Sale

  11 Adelaide Ave, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft
  • Built 1945

  11 Adelaide Ave, Pittsfield, MA 01201

  Last Sold Summary

  • 4% Above List Price
  • $217/SF
  • 107 Days On Market

  Last Sold Price $255,000

  Last Listing Agent Danielle Giulian William Pitt
• 

  

  /54

  $2,649,000 Under Contract

  • 6 Beds
  • 6.5 Baths
  • 4,289 Sq Ft

  250 West St, Lenox, MA 01240

  Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 423-1264

  250 West St, Lenox, MA 01240
• 

  

  /10

  $1,350 per month

  • 1 Bed
  • 1 Bath
  • Property for Rent

  235 East St Unit 210, Pittsfield, MA 01201

  Eastview Apartments. Featuring a one bedroom apartment on the second level with updated kitchen and bathroom. Fresh paint and move-in ready. Coin-op laundry, off street parking, and security on site. First months rent, last months rent, and half (1/2) security deposit due at lease signing. 2.6-3x Income required. Credit/Background checks (Minimum credit score of 660). Application fee of $45 is

  Cory Evangelisto NOCHER REALTY

  235 East St Unit 210, Pittsfield, MA 01201
• 

  

  /60

  $310,000 Sold Sep 26, 2025

  47 Hawthorne Ave, Pittsfield, MA 01201

  • 6 Beds
  • 2 Baths
  • 2,592 Sq Ft
  • Built 1915

  Last Sold Summary

  • 24% Above List Price
  • $120/SF
  • 15 Days On Market

  Current Estimated Value $309,564

  Last Listing Agent Corey Bishop BISHOP WEST REAL ESTATE

  47 Hawthorne Ave, Pittsfield, MA 01201
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  /47

  Est $1,631,053 Not Listed For Sale

  37 Fairwynds Dr, Lenox, MA 01240

  • 3 Beds
  • 3.5 Baths
  • 3,044 Sq Ft
  • Built 2011

  37 Fairwynds Dr, Lenox, MA 01240

  Last Sold Summary

  • 2% Above List Price
  • $526/SF
  • 3 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent Carrie Wright William Pitt
• 

  /2

  $300,000 Pending

  • 6 Beds
  • 4 Baths
  • 4,136 Sq Ft

  Unlisted Address

  THIS LISTING TO BE SOLD AS PART OF A 11 UNIT PACKAGE: Other properties included are located at 40-42 Henry Ave. Pittsfield, MA 01201 and 27-31 Pleasant St. Pittsfield, MA 01201. Acquire this three multifamily package offered at $920,000. Income & expense and rent roll document available in documents and or upon request.

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 779-3154

  Unlisted Address
• 

  

  /17

  $1,305 - $3,447 plus fees

  Forge

  1 - 3 Beds

  66 Brushwood Way, Lenox, MA 01240

  Forge is a brand new mixed-income housing community in Lenox, MA. The development includes 65 apartments within 13 townhome-style buildings, and a community clubhouse. Each building at Forge contains 5-6 apartments, with a mix of one-, two-, and three-bedroom apartments available at various income tiers (30, 60, 120% AMI). Apartments have their own entrances at a new road loop, which is

  66 Brushwood Way, Lenox, MA 01240
• 

  

  /47

  $660,000 Sold Aug 22, 2025

  36 Tucker St, Lenox, MA 01240

  • 4 Beds
  • 2 Baths
  • 2,242 Sq Ft
  • Built 1890

  Last Sold Summary

  • 2% Above List Price
  • $294/SF
  • 2 Days On Market

  Current Estimated Value $690,050

  Last Listing Agent Katie Soules WILLIAM RAVEIS REAL ESTATE

  36 Tucker St, Lenox, MA 01240
• 

  

  /29

  Est $343,315 Not Listed For Sale

  40 Wealthy Ave, Pittsfield, MA 01201

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Built 1958

  40 Wealthy Ave, Pittsfield, MA 01201

  Last Sold Summary

  • 1% Above List Price
  • $324/SF
  • 4 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
• 

  

  /8

  $1,719,000

  • 37 Beds
  • 24 Baths
  • 21,162 Sq Ft

  306 South St, Pittsfield, MA 01201

  Offered as a 7-property portfolio, totaling 21 units, this package includes a mix of multifamily properties and a single-family home with value-add potential. Several units are tenant-occupied, providing immediate income with upside potential, while others units require renovation, allowing investors to implement a phased improvement strategy. The portfolio currently generates an in-place NOI of

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 798-8328

  306 South St, Pittsfield, MA 01201
• 

  

  /17

  $1,100 per month

  • 2 Baths
  • 1,250 Sq Ft
  • Property for Rent

  34 Depot (Ste L1) St, Pittsfield, MA 01201

  Positioned in a convenient and accessible location, this ground level office space offers a practical and professional setting for a variety of business uses. The space features a large entry room and depending on your use, could have 2/3 offices and a conference room. This unit includes interior and exterior access, two private half bathrooms, and off-street parking adds to the overall

  Cory Evangelisto NOCHER REALTY

  34 Depot (Ste L1) St, Pittsfield, MA 01201
• 

  

  /35

  $385,000 Sold Nov 03, 2025

  57 Joseph Dr, Pittsfield, MA 01201

  • 3 Beds
  • 1.5 Baths
  • 1,204 Sq Ft
  • Built 1965

  Last Sold Summary

  • $320/SF
  • 17 Days On Market

  Current Estimated Value $378,878

  Last Listing Agent Christian Garner NOCHER REALTY

  57 Joseph Dr, Pittsfield, MA 01201
• 

  

  /37

  Est $386,352 Not Listed For Sale

  58 Valentine Rd, Pittsfield, MA 01201

  • 3 Beds
  • 2 Baths
  • 1,787 Sq Ft
  • Built 1955

  58 Valentine Rd, Pittsfield, MA 01201

  Last Sold Summary

  • 5% Above List Price
  • $206/SF
  • 8 Days On Market

  Last Sold Price $369,000

  Last Listing Agent THE KAHN TEAM BISHOP WEST REAL ESTATE
• 

  

  /97

  $349,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 4,009 Sq Ft

  514 South St, Pittsfield, MA 01201

  Set along one of Pittsfield's historic corridors, this circa 1815 Federal-style estate offers a compelling study in early American architecture, enduring design, and modern potential. Once a vibrant estate, the property still echoes its past, where landscaping and period lighting brought warmth and presence to the grounds. Inside, a quiet air of English refinement unfolds. Neoclassical detailing

  

  Syrah Bradley

  BISHOP WEST REAL ESTATE

  (413) 722-5807

  514 South St, Pittsfield, MA 01201
• 

  /2

  $1,400 total monthly price

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  3 Robbins Ave Unit 2ndFloor, Pittsfield, MA 01201

  No Smoking and No Pets preferred. Satisfactory Background Screening is Required. Move-in ready by April 1st First, last RequiredShowing Apartment by Appointment only.

  3 Robbins Ave Unit 2ndFloor, Pittsfield, MA 01201
• 

  

  /5

  $25,000 Sold Oct 01, 2025

  Lot #50 Barker Rd, Pittsfield, MA 01201

  • Land
  • 0.81 Acre
  • $30,864 per Acre

  Last Sold Summary

  • 42% Below List Price
  • 521 Days On Market

  Last Listing Agent Corey Bishop BISHOP WEST REAL ESTATE

  Lot #50 Barker Rd, Pittsfield, MA 01201
• 

  

  /32

  Est $183,667 Not Listed For Sale

  33 Craigie Ave, Pittsfield, MA 01201

  • 2 Beds
  • 1 Bath
  • 966 Sq Ft
  • Built 1890

  33 Craigie Ave, Pittsfield, MA 01201

  Last Sold Summary

  • 15% Above List Price
  • $166/SF
  • 6 Days On Market

  Last Sold Price $160,000

  Last Listing Agent Mark Harris SIGNATURE ASSOCIATES
• 

  

  /47

  $650,000

  • 5 Beds
  • 3.5 Baths
  • 3,074 Sq Ft

  161 Leona Dr, Pittsfield, MA 01201

  Set in one of Southeast Pittsfield's most desirable neighborhoods, this very sunny and impeccably maintained home offers the perfect balance of gracious living, flexible space, and effortless entertaining. Lovingly cared for by its current owner, the home unfolds with elegant formal rooms, hardwood floors, and a warm wood burning fireplace anchoring the living room. The heart of the home is an

  

  Nick Geranios

  WILLIAM PITT SOTHEBY'S - LENOX

  (413) 570-8931

  161 Leona Dr, Pittsfield, MA 01201
• 

  

  /26

  $2,500 per month

  • 2 Baths
  • 2,500 Sq Ft
  • Property for Rent

  34 Depot (Ste 301) St, Pittsfield, MA 01201

  Positioned in a convenient and accessible location, this third-floor office space offers a practical and professional setting for a variety of business uses. The space features three private offices, a large common area with a multitude of uses, a kitchen, and a reception area with built-in desk. The building includes shared restroom facilities on the same floor, along with elevator access that

  Cory Evangelisto NOCHER REALTY

  34 Depot (Ste 301) St, Pittsfield, MA 01201
• 

  

  /13

  $295,500 Sold Oct 06, 2025

  61 Pomeroy Ave, Pittsfield, MA 01201

  • 6 Beds
  • 2 Baths
  • 3,081 Sq Ft
  • Built 1880

  Last Sold Summary

  • 6% Above List Price
  • $96/SF
  • 86 Days On Market

  Current Estimated Value $308,593

  Last Listing Agent Jessie Carlino MACCARO REAL ESTATE

  61 Pomeroy Ave, Pittsfield, MA 01201
• 

  

  /40

  Est $529,612 Not Listed For Sale

  29 Yvonne Dr, Dalton, MA 01226

  • 4 Beds
  • 3.5 Baths
  • 3,296 Sq Ft
  • Built 1975

  29 Yvonne Dr, Dalton, MA 01226

  Last Sold Summary

  • 9% Above List Price
  • $148/SF
  • 104 Days On Market

  Last Sold Price $487,500

  Last Listing Agent Maggie Gavin William Pitt
• 

  

  /42

  $1,280,000 Open Sat 11AM - 2PM

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

  18 Highcrest Rd Unit 20, Lenox, MA 01240

  

  Selina Lamb

  Birch Properties

  (413) 591-5654

  18 Highcrest Rd Unit 20, Lenox, MA 01240
• 

  

  /26

  $1,300 total monthly price

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  51 Orchard St Unit 1, Pittsfield, MA 01201

  51 Orchard St Unit 1, Pittsfield, MA 01201
• 

  

  /40

  $660,000 Sold Jul 10, 2025

  176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262

  • 2 Beds
  • 2.5 Baths
  • 1,853 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $356/SF
  • 133 Days On Market

  Last Listing Agent Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262
• 

  

  /28

  Not Listed For Sale

  82 Lyman St, Pittsfield, MA 01201

  • 5 Beds
  • 4 Baths
  • 2,488 Sq Ft
  • Built 1905

  82 Lyman St, Pittsfield, MA 01201

  Last Sold Summary

  • $143/SF
  • 50 Days On Market

  Last Sold Price $355,000

  Last Listing Agent Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
• 

  

  /43

  $445,000

  • 2 Beds
  • 3 Baths
  • 1,814 Sq Ft

  35 Chapman Rd, Pittsfield, MA 01201

  Classic New England farmhouse featuring a charming kitchen with beautiful Berkshire views and an open, inviting layout perfect for entertaining. The 1st floor offers, full bath and convenient laundry hookups, along with 2 living rooms. One ideal for relaxation and the other a perfect home office, playroom, game room. Upstairs, you'll find 2 good sized bedrooms each with their own full bathroom

  

  Laura Arseneau

  PAULA MCLEAN REALTORS INC.

  (413) 323-3512

  35 Chapman Rd, Pittsfield, MA 01201
• 

  

  /9

  $395 per month

  • 2 Baths
  • 280 Sq Ft
  • Property for Rent

  34 Depot (Ste 204) St, Pittsfield, MA 01201

  Positioned in a convenient and accessible location, this second-floor office space offers a practical and professional setting for a variety of business uses. The space features a single, well-sized office with all utilities included. The building includes shared restroom facilities on the same floor, along with elevator access that provides easy entry to all levels. Off-street parking adds to

  Cory Evangelisto NOCHER REALTY

  34 Depot (Ste 204) St, Pittsfield, MA 01201
• 

  

  /17

  $268,000 Sold May 01, 2025

  10 Hillside St, Pittsfield, MA 01201

  • 6 Beds
  • 3.5 Baths
  • 2,584 Sq Ft
  • Built 1910

  Last Sold Summary

  • 6% Below List Price
  • $104/SF
  • 11 Days On Market

  Current Estimated Value $285,528

  Last Listing Agent Marnie Garzone BISHOP WEST REAL ESTATE

  10 Hillside St, Pittsfield, MA 01201
• 

  

  /36

  Not Listed For Sale

  Unlisted Address

  • Built 1969

  Unlisted Address

  Last Sold Summary

  • $67/SF
  • 0 Days On Market

  Last Sold Price $1,875,000

  Last Listing Agent Elisha Poirier STONE HOUSE PROPERTIES, LLC

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