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$285,000
6 Beds ⋅ 2 Baths ⋅ 73572896 MLS
Each unit offers 3 bedrooms and 1 full bathroom, for a total of 6 bedrooms and 2 bathrooms. Both apartments feature natural gas heat and hot water, public water and sewer, and basement washer/dryer hookups for each unit. Enjoy a private, fully fenced backyard. Conveniently located near Berkshire Medical Center, downtown, and local restaurants. A great investment opportunity for those seeking a fully rented, income-producing property in a convenient location!

3-5 Pleasant St, Pittsfield
$269,900
6 Beds ⋅ 3 Baths ⋅ 73572779 MLS
Ideally located in the Downtown Arts District just off South Street, this two-family property offers an excellent investment opportunity. Fully renovated in 2007, the property features a total of 6 bedrooms and 2½ bathrooms, with separate utilities for each apartment, paid by the respective tenants.The first-floor apartment offers 3 bedrooms, 1½ bathrooms, and numerous updates throughout. The second-floor apartment features 3 bedrooms and 1 full bathroom, providing comfortable and functional living space.The property is serviced by public water and sewer and is equipped with two electric meters, two boilers, and two hot water heaters. Both apartments are heated with natural gas, with natural gas hot water as well. Conveniently located near Berkshire Medical Center, Berkshire Museum, The Colonial Theatre, Barrington Stage, schools, restaurants, shopping, and downtown attractions. Zoned business and residential, this property offers excellent investment potential in a convenient downtown location. Don't miss this opportunity!

7-9 Goodrich St, Pittsfield
$179,900
6 Beds ⋅ 2 Baths ⋅ 73572558 MLS
Side by side two-family home with attached workshop with loft above, and detached two-car garage on a corner lot! This is a fixer-upper. Unit 342 is currently rented. The apartment consists of a living room with hardwood floors and large eat-in kitchen in the 1st floor, and 2 bedrooms and full bathroom on the 2nd floor. Unit 340 is in need of major rehab. The 1st floor consists of a very spacious kitchen, living room, dining room and huge full bathroom. Since the kitchen has plenty of space for dining area, there is great potential for a large first-floor primary bedroom, come envision it! Upstairs you will find 4 bedrooms and access to the walk-up attic which has rooms that were finished as bonus space at some pointThe property is served by city water & sewer, and each apartment has separate natural gas heat/hot water & electricity, with 100 amp electrical panel for each unit. Both of the heating systems are older. The roof was already replaced in 2022. The garage, workshop and the vacant unit need extensive work. The home is ready for your vision! This is an excellent opportunity just minutes from downtown, within walking distance to restaurants, about two-minute drive to Berkshire Medical Center, and just a few minutes from Pontoosuc lake, among other nearby attractions!

340-342 Wahconah St, Pittsfield
$149,900
6 Beds ⋅ 2 Baths ⋅ 73571485 MLS
Come put your finishing touches on this large 6 bed, 2 bath multifamily! Significant work has already been completed. This is your chance to bring a great project over the finish line!

516-518 Union St, North Adams
$2,295,000
31 Beds ⋅ 29 Baths ⋅ 73567764 MLS
A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90± acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style.The original mansion remains at the heart of the property, surrounded by broad lawns and buildings added during its later evolution into an educational campus. Much of the character of the original country house remains, including handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors.Beyond the main house are two dormitory residences with approximately 24 bedrooms and shared common spaces, a separate multi-level building with commercial kitchen and dining facilities, classrooms, offices, library, conference and infirmary spaces, a substantial gymnasium, and additional support buildings. For a residential buyer, this unusual collection offers possibilities for guest and staff accommodations, studios, offices, recreation, wellness, or a multi-generational Berkshire estate, subject to applicable approvals.The gymnasium could accommodate fitness, indoor tennis, pickleball, squash, or other private amenities. Existing infrastructure includes public water, multiple electrical services, mixed heating systems, central air in the dormitories and gymnasium, commercial sprinklering in select buildings, extensive parking, and established internal circulation.Hillcrest currently operates on the campus under a lease through June 2027 and presently anticipates vacating in February/March 2027.This offering is for 349 Old Stockbridge Road only. The property is also marketed as part of a combined offering with 40 Frothingham Crossing; see MLS #73518284.For its next steward, Overlee offers the rare chance to inherit not simply a house, but an entire Berkshire estate—historic architecture, expansive grounds, and a collection of buildings ready to support a new vision.Offered at $2,295,000.

349 Old Stockbridge Rd, Lenox
$249,900
6 Beds ⋅ 3 Baths ⋅ 73558223 MLS
Calling all investors and hands-on owner-occupants! This 3-unit multi-family offers 15 rooms, 6 bedrooms, and 3 full baths across 3,510 sq ft on a 0.17-acre lot. The owner has already made key updates, including some new flooring, fresh paint, updated electric, and a new bulkhead, giving you a head start on renovations. Still needed: updated heating systems, roof work, wall patching, and final cosmetic finishes; a great candidate for a renovation loan (203k/HomeStyle) if you're looking to live in one unit while building equity. Investors can pick their own tenants and set market rents once complete. Public water/sewer and a full basement round out this diamond-in-the-rough opportunity to add to a portfolio or start one.

32 Westminister St, Pittsfield
$325,000
6 Beds ⋅ 4 Baths ⋅ 73557707 MLS
Don't miss this recently renovated two-family property in a desirable location close to downtown! Each spacious unit offers 3 bedrooms and 1.5 bathrooms, featuring updated kitchens and baths, beautifully refinished hardwood floors, and functional layouts. Whether you're looking to expand your investment portfolio or owner-occupy while generating rental income, this property checks all the boxes. Conveniently located near shopping, dining, schools, and local amenities, this is an excellent opportunity in a sought-after neighborhood.

34-36 Crandall St, Adams
$399,000
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
7 Beds ⋅ 4 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
$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
$160,000
6 Beds ⋅ 2 Baths ⋅ 73538907 MLS
This property shares a driveway with the two-family next door at 73-75 Hall St, which is also available for sale! 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
$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
$3,195,000
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
$230,000
6 Beds ⋅ 2 Baths ⋅ 73486317 MLS
Two-family flat with one unit renovated and the other unit ready to be completed. Each apartment consists of living room, dining room, kitchen 3 bedrooms and 1 bathroom. There is a lovely front porch offering gorgeous mountain views! The third floor is the attic, separate from the apartments, offering ample storage space. This is where the furnace for 2nd floor unit is located. The home has city water and sewer and there is a good parking area on the back of the building. Great, convenient location, walking distance to many downtown attractions, just minutes from MCLA, MassMoca, restaurants and more.This property shares a driveway with the two-family next door at 69-71 Hall St, which is also available for sale!

73-75 Hall St, North Adams
$34,900
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
$9,500,000
7 Beds ⋅ 9 Baths ⋅ 73445189 MLS
Offered fully furnished and ready to enjoy, 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.

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

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