Refine Search
Map
Sort by
$419,000
8 Beds ⋅ 4 Baths ⋅ 73554619 MLS
Presenting a distinguished multi-family property located at 53 Orchard St, Pittsfield, MA.. This expansive 4 unit spans 2688 square feet of living area, offering a rare opportunity for sophisticated urban living or a strategic investment. This property includes six generously proportioned bedrooms, providing ample private accommodations across its two stories. The property's substantial lot size of 4160 square feet provides a significant footprint within the urban landscape. We invite you to discover the potential and unique character of this Pittsfield address. Three Units are vacant and recently remodeled with market rents averaging about 1395.00 in the area. One Unit is rented month to month at 950.00. All units are lead certified.

53.5 Orchard St, Pittsfield
$375,000
6 Beds ⋅ 3 Baths ⋅ 73554585 MLS
Turnkey 3-unit multifamily investment in Pittsfield, just minutes from downtown. 100% 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 expenses: taxes $3,102.87, insurance $3,168, electric $365.34, water & sewer $2,265.48. Priced at just $102/SF — well below nearby comparable sales at 91 Dalton Ave ($114.50/SF) and 1 Rostone Pl ($119.50/SF). A stable, cash-flowing asset with strong relative value in a growing rental market. Buyer to do Due Diligence.

98 Lincoln St, Pittsfield
$379,900
6 Beds ⋅ 4 Baths ⋅ 73541907 MLS
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 great opportunity.

60 Division St, Pittsfield
$1,750,000
6 Beds ⋅ 5 Baths ⋅ 73550137 MLS
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 dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately fireplaces anchor the formal living spaces. Enjoy panoramic views and privacy from the grand porch overlooking 4 pristine acres. a state-of-the-art kitchen featuring Wolf and Sub-Zero, and no expense spared Geo-Thermal heating/cooling.

500 Williams, Pittsfield
$14,500,000
19 Beds ⋅ 25 Baths ⋅ 73544510 MLS
The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

11 Hawthorne, Stockbridge
$180,000
6 Beds ⋅ 2 Baths ⋅ 73538907 MLS
Bring your ideas and finishes and make this two family home a beautiful property! The interior is gutted, but a lot of the work is done, including new metal roof, high efficiency heating system siding, windows and a lovely front porch already done, as well as new heating system. There is town water & sewer, and parking spaces on the back of the home. Great, convenient location, walking distance to many downtown attractions, just minutes from MCLA, MassMoca, restaurants and more.

69-71 Hall St, North Adams
$220,000
7 Beds ⋅ 3 Baths ⋅ 73538546 MLS
Bring your vision and creativity to this spacious side-by-side duplex that's been stripped down and prepped for its next chapter. Much of the heavy lifting has already been completed, including extensive demolition work and rough electrical installation. The exterior has also received a 1st of coat of paint. Originally intended to be converted into townhouses and sold separately, the owner's plans have changed, creating an exciting opportunity to customize a property to their needs. One unit offers 4 bedrooms and 1.5 baths, while the second features 3 bedrooms and 1.5 baths. Both units include private enclosed front porches, open rear porches, and spacious layouts ready to be transformed. The walkout basement opens to the backyard and offers additional possibilities. Whether you're looking to create income-producing rentals, pursue a townhouse conversion, or design your dream multi-generational property, this diamond in the rough is packed with potential.

27 Daniels Ave, Pittsfield
$1,450,000
20 Beds ⋅ 18 Baths ⋅ 73536485 MLS
162 Woodlawn Ave is comprised of two (2) 2-Bedroom/1-Bathroom units, eleven (11) 1-Bedroom/1-Bathroom units, and five (5) Studio units with 8,653 square feet of gross living area in 11,653 square feet of gross area. The Property is situated upon a 0.47-acre parcel and offers twenty (20) off-street parking spaces. The Property is well-positioned within Pittsfield’s established Morningside neighborhood, offering convenient access to downtown amenities while maintaining a residential setting. The Property is separately metered for electricity, while the Landlord is responsible for gas powered heat & hot water, as well as domestic water & sewer. The Property benefits from quick access to U.S. Routes 7 and 20, which link the city to the Massachusetts Turnpike (I90) at Exit 10 in Lee, creating efficient regional highway connectivity toward Springfield, Worcester, Boston, Albany, and New York State. The opportunity exists to acquire a well maintained asset in the beautiful Berkshires area.

162 Woodlawn Ave, Pittsfield
$65,000
12 Beds ⋅ 5 Baths ⋅ 73531701 MLS
Opportunity knocks! This 4-family property has suffered significant fire damage and is being sold as-is for land value. Ideal tear down project with endless redevelopment potential. The lot includes a detached garage and offers ample space for new construction. Bring your vision and rebuild in a growing area with strong rental demand. Cash or construction financing only. All offers considered. Can Bundled with 242 Wahconah st & 40 Pecks rd.

48 Brown St, Pittsfield
$160,000
6 Beds ⋅ 2 Baths ⋅ 73531686 MLS
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 (Pittsfield) for even greater investment potential. Endless possibilities await, renovate, rebuild, or reimagine this space to maximize returns! Schedule a showing today!

242 Wahconah St, Pittsfield
$830,000
12 Beds ⋅ 1 Baths ⋅ 73531673 MLS
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, this property is ideal for adaptive reuse into loft-style apartments, townhomes, or mixed-use development. Conveniently located in a growing area with access to local amenities, schools, and transportation. this site is primed for investors and developers seeking their next project. Don’t miss this A+ Investment. schedule your private tour today! This Property can be bundled with 48 Brown & 242 Wahconah st.

40 Pecks Rd, Pittsfield
$375,000
6 Beds ⋅ 2 Baths ⋅ 73531392 MLS
Escape to the Berkshires in this stunning Victorian gem — designed for those who appreciate space, style, and character. Whether you're planting roots in North Adams or seeking a weekend retreat. Fully renovated 5-bed, 2-bath home with 2,551 sq ft in the heart of North Adams. Slate roof, repainted front porch, chimney repairs, and updated plumbing and electrical throughout. Inside features refinished black India ink hardwood floors, new lighting fixtures, popcorn ceiling removal, washer/dryer hookups, and designer finishes including Revere Pewter and Gentlemen's Grey. Both bathrooms fully refreshed with new tile, fixtures, and flooring. Furniture included.Minutes from Mass MoCA and the Mohawk Trail. Proven short-term rental with 4 years of documented Airbnb performance, consistent 5-star guest reviews. Professional management on 24/7 - completely turnkey. Active Airbnb listing available upon request to verify income history. Showings available between guest stays.

71 North Holden St, North Adams
$3,750,000
34 Beds ⋅ 31 Baths ⋅ 73518284 MLS
Rare 16.76± acre contiguous institutional campus and redevelopment opportunity in Lenox, MA, in the heart of the Berkshires. Anchored by Overlee, a historic 1903 estate, the property includes multiple buildings with 32 dormitory-style bedrooms, classroom and administrative space, dining facilities, shared common areas, and a large gymnasium. Existing infrastructure includes internal roadways, parking, public water, sprinkler systems, mixed heating, and up to 600 amp electrical service. Also included is a 1,826 SF residence on 4.74± acres across three contiguous parcels offering additional flexibility. Currently operated as an educational campus, the property offers compelling long-term potential for institutional, residential, wellness, medical, hospitality, or mixed-use concepts. Buyers to conduct due diligence.

349 Old Stockbridge Rd, Lenox
$2,950,000
7 Beds ⋅ 8 Baths ⋅ 24171893 MLS
Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and equestrian excellence. Spanning 27.3+ bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence/Inn, three enchanting cottages, and the potential to include the region's premier full-service equestrian facility. The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The main house/inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations. For the serious equestrian, the estate offers multiple barns and paddocks. Training is a year-round luxury thanks to the 6,000 sqft heated indoor arena, which includes an owner's apartment and viewing area - and a professional grade outdoor ring. Enjoy all the area attractions including Tanglewood, the Mount, MASS MoCa and breathtaking hiking trails.

802 State Rd, Richmond
$4,850,000
13 Beds ⋅ 14 Baths ⋅ 73496031 MLS
The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.

2 Kemble, Lenox
$129,900
7 Beds ⋅ 5 Baths ⋅ 73478110 MLS
Come finish the renovation of this expansive 7 bedroom home! This project is ready for your vision and creativity to bring it to fruition! Don't miss this opportunity!

15 Buel St, Pittsfield
$49,900
6 Beds ⋅ 2 Baths ⋅ 73475425 MLS
Come see this 2-unit today! Both units feature 3 bedrooms and a full bathroom. Property is mostly gutted and ready to be renovated. Some newer framing and wiring has already been started. Finish this project and make it shine again!

27 Hall St, North Adams
$7,250,000
6 Beds ⋅ 7 Baths ⋅ 24151033 MLS
A rare French Manor estate on one of the most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook-creating a secluded retreat that feels worlds away, yet remains moments from the cultural heart of the Berkshires. It is awaiting buyers final finishes. At the center of the estate stands a newly built main residence inspired by the grand proportions of the Gilded Age, featuring soaring 19-foot ceilings and impeccable architectural presence. Thoughtfully constructed by a highly regarded local craftsman, the home showcases state-of-the-art mechanical systems, including geothermal heating and cooling, blending classic elegance with modern efficiency. Approaching completion, the residence presents a rare opportunity for the next owner to personalize select finishes and make this remarkable home truly their own. A short stroll west leads to a beautifully converted barn guest house, carefully relocated to the property and transformed into a dramatic open-concept retreat. Soaring ceilings, antique beams, and expansive windows frame the estate's sweeping mountain and pond views, creating an inviting space for guests, artists, or quiet reflection.

209 Blue Hill Rd, Great Barrington
$249,900
6 Beds ⋅ 2 Baths ⋅ 73460510 MLS
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 well-updated, income-ready property is the perfect fit.

17 Wallace Pl, Pittsfield
$9,500,000
7 Beds ⋅ 9 Baths ⋅ 73445189 MLS
Offered with Seller Financing, this Majestic Tudor Berkshire Estate sits on 71 Acres atop Tom Ball Mountain in quaint Alford, MA. Privacy and Breathtaking views. Formal Entry and Foyer. Stately Living Room and Dining Room. Great Room with Gourmet Kitchen. Den, Family Room, Gym and Massage Room. 5 en-suite Bedrooms in the Main House. 2 Bedroom Tudor Guest House w beamed ceilings and full amenities. Manicured grounds, infinity Pool and Hot Tub, Pool House with full Bath, Tennis Court and Pickleball Court. 7 Garages and additional Barn. Exquisite architectural touches, state-of-the-art home technology and security, in the most peaceful of surroundings. Easy access by road, rail and private Airport. Close to Tanglewood and Berkshire attractions. *Fully Furnished and ready to enjoy.

30 East Rd, Alford
$5,650,000
11 Beds ⋅ 10 Baths ⋅ 24013888 MLS
Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of the future for generations to come. Set on 67 +/- park-like acres this property offers 3 unique residences, a mature specimen tree farm, a spring-fed pond, wooded walking trails, and captivating views of the distant mountains all just a stone's throw away to restaurants and shops. At the heart of the estate stands The Tullar House; a well-preserved and substantial 6-bedroom 5,000+ sq ft antique Dutch Gambrel dating back to 1761, reported to be the 2nd oldest house in Egremont. Retaining much of its original charm and detail, this historic jewel boasts ample-sized rooms for gatherings and entertaining, a renovated chef's kitchen, a formal dining room, 3 grand fireplaces, 2 primary suites, and plenty of room for guests. Enjoy sweeping views of the grounds from the porch laid with locally sourced marble or relish in the shade of 'The Champion', a 250+-year-old Black Walnut Tree standing as the oldest in the state and serving as a living testament to Tullar Farms' rich past. The exterior is a sight to behold with ornate and symbolic details that capture the attention of all who pass by.

25 Sheffield Rd, Egremont
$3,490,000
10 Beds ⋅ 6 Baths ⋅ 73431481 MLS
Welcome home to NEWGRANGE. 1920's era Manor House with lake frontage on Lake Garfield. Over 10,000 square feet of living on 7.7 Acres. Complete the restoration and enjoy original Stone Fireplaces, comfortable Living spaces, formal Dining and 10 Bedrooms. Write that novel in the paneled Office, Library or Sunroom, create delicacies in the Country Kitchen, or shoot a round of pool in the Billiard Room. When you are done, meander to your private Dock on 165 feet of glorious private lakefront. Guest House, Pond, and Gardens originally designed by Frederick Law Olmstead. Close to town, Skiing, Shopping, Dining and Tanglewood. Low, low Monterey taxes. This one-of-a-kind property is meant for enjoying all that the Berkshires has to offer.

535 Main Rd, Monterey
$1,750,000
22 Beds ⋅ 21 Baths ⋅ 73245373 MLS
The Possibilities are endless! Family Compound & Retreat ! Hotel, Wedding Venue, Campgrounds, Cross Country Skiing Trails or Family Compound, bring your imagination and bring Buck Steep Manor back to Life! Five Buildings and many Cabins amid this 350-acre Estate. The Manor House 25 rooms the Lodge 19 rooms the Dutch Colonial Barn 5 rooms the Cottage 10 rooms The Antique Carriage Barn Hall 99pl capacity, and the Post and Beam Utility Barn two levels. Photos are from the past when it was running as a venue. It has frontage on Washington Mt Rd, Frost Rd and Lovers Lane Rd. Come view this unique property you won't be disappointed. All Information to be confirmed by Buyer. See Also MLS Listing 73240084 in Commercial.

885 Washington Mt. Rd., Washington

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.