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$264,900
4 Beds 2 Baths 73575640 MLS
Attention Investors & Portfolio Builders! Exceptional turn-key opportunity to acquire a high-yield, fully leased 2-family home in Pittsfield. Built in 1880, this solid Colonial-style income-producer delivers an ideal layout optimized for low landlord overhead and immediate, stable cash flow from day one. A standout feature of this asset is the entirely separate utility infrastructure, substantially lowering your operational expenses. The downstairs unit (Unit 1) features a comfortable 5-room, 2-bedroom, 1-bathroom unit. The sprawling upstairs unit (Unit 2) offers a spacious 6-room configuration, including 2 traditional bedrooms plus a flexible bonus room—perfect as a 3rd bedroom or home office—complete with its own dedicated in-unit laundry room. With separate meters in place, the tenants handle their own primary utility bills, keeping your net operating income predictable and protected. Both units are used as 3 Bedroom units. The property sits on a low-maintenance 2,613 sq. ft. lot requiring minimal seasonal landscaping or upkeep, and includes essential off-street parking. Structurally sound with an interior-access fieldstone foundation and durable asphalt shingle roofing, this building has been well-maintained. Positioned just moments from downtown Pittsfield, tenants enjoy unparalleled convenience with immediate proximity to local employment hubs, public transit lines, commuter routes, public parks, dining, and retail centers. If you are looking to execute a stable buy-and-hold strategy and clear a strong capitalization rate with active tenant leases already in place, 48 Fourth Street represents an incredibly strategic addition to your real estate portfolio. The low FY2026 residential tax rate further bolsters your bottom line. Do not miss this low-overhead, high-demand multi-family asset. Schedule your walkthrough today!

48 Fourth, Pittsfield

$229,900
2 Beds 2 Baths 73573584 MLS
Escape the hustle and bustle and enjoy the beauty of the Berkshires! Located in the peaceful town of Savoy, this charming ranch offers 2 bedrooms, 1 full bath, and approximately 3 acres of land to enjoy. Features include hardwood floors, a cozy wood stove, full basement with walkout access, and a convenient one-car attached garage. A new septic system is currently being installed, providing added peace of mind for the next owner. Surrounded by nature yet just a short drive to the Berkshires' many attractions, dining, hiking, recreation, and cultural destinations. Whether you're looking for a year-round home, weekend getaway, or peaceful retreat, this property offers a wonderful opportunity to enjoy country living while still being close to all the area has to offer.

304 Chapel Rd, Savoy

$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

$3,695,000
4 Beds 6 Baths 73568631 MLS
STILL HOUSE brings a new level of contemporary design to the Berkshires—quietly luxurious, exquisitely detailed, and made to be lived in. Minutes from the center of Great Barrington, this newly completed 5,148-square-foot home pairs the distinctive vision of acclaimed Brooklyn studio Me & General Design with exceptional craftsmanship and materials throughout. Four bedrooms, five-and-a-half baths, a heated saltwater pool, bespoke spa and fitness spaces, solar energy and exceptional privacy make this as much a retreat as a home.Preserved stone walls from the original structure bring history, texture and a distinctly Berkshire character to the new architecture. The main living level opens into a dramatic kitchen, dining and living space with cathedral ceilings, two stories of glass and views into the surrounding landscape. The custom Porcelanosa kitchen features richly veined stone, a substantial island, induction cooking, double ovens, integrated refrigeration, microwave drawer, dedicated coffee station and breakfast nook. A separate stone-walled sitting room offers a restored wood-burning fireplace and a more intimate place to gather.The main-level primary suite makes true one-floor living possible, with direct deck access, a walk-in closet and private bath. Upstairs are two additional bedrooms and two full baths, plus a library/sitting area overlooking the great room. The light-filled lower level includes a private fourth bedroom suite, home cinema, office, yoga/Pilates studio, traditional Canadian red cedar sauna, full bath and laundry.High-efficiency multi-zone heat pumps, radiant lower-level heat and solar energy support year-round comfort. Outside, the heated saltwater pool is set against mature trees, with decks, paths, stonework and an outdoor fireplace creating places to gather throughout the seasons. Landscape design by Windy Hill Farm complements the natural setting.Lake Mansfield, Monument Mountain, Ski Butternut, Tanglewood, Jacob's Pillow and the restaurants, shops and cultural life of Great Barrington are all within easy reach.STILL HOUSE is the inaugural residence of NUESTRA Collection, a series of design-led Berkshire homes created around a simple idea: exceptional contemporary design should feel as good to live in as it is to look at.

114 Christian Hill Rd, Great Barrington

$2,295,000
31 Baths 73567766 MLS
A rare opportunity to acquire an established 11.90± acre campus in Lenox, Massachusetts, with substantial institutional infrastructure and educational use permitted by right within the property's R1A residential zoning district.At its center is Overlee, a distinguished Berkshire estate built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style. The historic mansion has served as the academic and administrative center of Hillcrest Educational Center, with classrooms, offices, and gathering spaces throughout. Original details remain, including handsome woodwork, fireplaces, and a striking ballroom; the house also historically included bedrooms on its upper floors.The campus includes two dormitory buildings with approximately 24 bedrooms and shared common spaces, plus a separate multi-level academic/support building with commercial kitchen and dining facilities, classrooms, offices, library, conference, and medical/infirmary spaces. A substantial gymnasium offers potential for athletics, fitness, indoor tennis, pickleball, squash, wellness programming, or other recreational uses. Additional support buildings, parking, internal circulation, public water, multiple electrical services, mixed heating systems, central air in the dormitories and gymnasium, and commercial sprinklering in select buildings support continued campus operation.The property is zoned R1A residential, with educational use permitted by right. Any alternative use, subdivision, or redevelopment is subject to Town of Lenox zoning and applicable approvals.Hillcrest currently operates on the property 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 #73518283.Offered at $2,295,000.

349 Old Stockbridge Rd, Lenox

$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

$180,000
4 Beds 2 Baths 73567609 MLS
Conveniently located near downtown Pittsfield, this home sits on .14 acres with a backyard for entertaining and garage for storage. The first floor offers a living room, dining room, kitchen, bathroom, and a flexible space with many possibilities. Upstairs are 3 bedrooms, a full bathroom, and a walk-up attic. The walk-out basement provides additional potential. Major updates include cellulose insulation and basement air sealing/weatherstripping (2017), new roof (2019), new furnace (2021), furnace cleaning (2025), and chimney reconstruction with stainless-steel liner (2025). Ideal for those looking to bring their own renovations and bring out this home's great potential. Property is being sold AS IS with all contents remaining.

39 Hull Ave, Pittsfield

$349,900
3 Beds 2 Baths 73566643 MLS
Raised ranch with two-car garage, located on a double lot with almost half an acre of land. The main level features 3 bedrooms, full bathroom, living room and kitchen with dining area, with slider opening to deck which was recently painted. The finished lower level offers family room with sliders to the backyard. In addition to the hot water baseboard, this family room also features a pellet stove. In the ground level you will also find an additional bathroom with stand-up shower and washer/dryer. The bathroom has brand new flooring and sink! The lower lever also offers garage access plus an unheated bonus room last used as an office. The backyard is private and there is also a large shed! The home was built in 1995, it has natural gas heat and hot water, city water/sewer and a shed is included. There are two extra parking spaces a little up the street on the adjacent lot that is already being included with the house. *Floor plans available

225 Brown St, Pittsfield

$724,900
5 Beds 4 Baths 73564933 MLS
Tucked away on 3.24 private wooded acres, this one-of-a-kind Contemporary offers 3,744 sq. ft. of living space across three finished levels. Soaring ceilings, exposed timber beams, hardwood floors, and dramatic center chimney create a warm yet impressive setting. The open floor plan is anchored by multiple wood-burning fireplaces, a pellet stove, and abundant natural light. Offering a total of five bedrooms and 3.5 baths, including a private in-law suite above the oversized attached two-car garage, this home provides exceptional flexibility for guests or extended living. Enjoy an owned 9.52 kW solar system, spacious decks, beautifully maintained grounds, and the privacy of a true Berkshire retreat just a short drive from everything the Berkshires and Northampton have to offer.

255 High St Hill Rd, Windsor

$879,000
3 Beds 3 Baths 73563529 MLS
Welcome home to an extraordinary blend of modern style, flexible living, and resort-quality outdoor amenities, perfectly located moments from the heart of downtown Lenox, top-notch dining, Tanglewood, & the local high school on a quiet cul-de-sac. Step inside to a bright, freshly painted open floor plan framed by updated windows that flood the space with natural light. The inviting living area features a cozy gas fireplace, creating a warm focal point for chilly evenings, while the kitchen comes equipped with sleek, modern appliances. This turnkey residence offers 3 spacious bedrooms plus a versatile 4th full-size room that's ideal for a fourth bedroom, dedicated home office, or quiet retreat—along with 2.5 updated bathrooms. Downstairs, a vast, full open basement provides endless possibilities for exceptional storage, a home gym, or a recreation room. Beyond the interior, your ultimate outdoor sanctuary awaits in a professionally landscaped, fully fenced-in yard lined with a lush hemlock hedge for total privacy. Spend sunny summer days lounging by the sparkling in-ground saltwater pool, while the built-in swing set adds ready-to-use fun for family and guests. Complete with major exterior upgrades including an updated roof, newer siding, a spacious 2-car garage, and a shed, this exceptional property delivers total peace of mind and the best of Berkshire living right at your doorstep.

22 Post Rd, Lenox

$1,260,000
5 Beds 4 Baths 73563141 MLS
Historic 1815 compound — 3 independent income-producing units — $154K gross revenue in 2025. 1815 Greek Revival farmhouse duplex + converted barn — an investment rental property or family compound minutes from Main Street Stockbridge. Turnkey 5-star Airbnb, 6 years running, $154K/year. On historic registry as birthplace of a U.S. Supreme Court Justice. Compact, low-maintenance parcel — all the Berkshires, none of the yard work. Original wide-beam floors, log rafters, double-sided fireplace with brick vaulted bread oven, mature gardens with bistro tables. Three addresses — 1574, 1577 & 1579 Pleasant St. Each unit fully self-contained with own entrance, kitchen, W/D, electricity meter, and heat source. 1574: 2BR/1BA downstairs.1579: 2+BR/2BA upstairs 1577: converted barn with king bed, queen futon loft, and full bath. The hard work is done; you simply take over a fully operational hospitality business. THE NUMBERS 2025 Gross Revenue: $153,702 | NOI: $136,526 | Cap Rate: 10.84% | Gross Yield: 12.20%5-yr avg NOI: $122,423. No pro forma. No projections. All actual. Revenue documented across all seasons— summer STR, fall/winter: remote professionals, insurance relocation, medical professionals. No stabilization period needed. THE LOCATION Minutes to Tanglewood, Kripalu, Stockbridge Bowl. 2.5 hrs NYC · 2 hrs Boston. Peak STR demand June–Aug; remote professionals and corporate tenants fill all three units Sept–May. Twelve months of documented revenue, no seasonal gap over 6 years. THE OPPORTUNITY Historic designation as birthplace of U.S. Supreme Court Justice Henry Billings Brown — a permanent differentiator no new build can replicate. Active STR/MTR listings, 4.88-star brand, 180+ reviews, active forward bookings, guest handbook, host handbook, and operating playbook all convey. Municipal sewer (no Title 5) · public water · FEMA Zone X · dual residential + commercial zoning · electrical updated · 4th unit potential in unfinished barn garage. Furniture, kitchenware, linens + digital marketing assets excluded; available by separate agreement. Active STR — all units occupied.

1574-1579 Pleasant St, Lee

$399,000
2 Beds 2 Baths 73562899 MLS
Close to Garnet Lake!!! Discover this Gorgeous home, constructed in 2007, presenting modern interior details and a Beautiful log exterior. This attractive property offers a unique opportunity for a primary residence or a getaway retreat.. The kitchen is thoughtfully designed with an abundance of fine cabinetry providing both functionality and a central gathering space for culinary endeavors. Open to the kitchen you will find an inviting Dining area and Family Room with impressive high wood ceilings. A first floor bedroom, full bath and a possible additional bedroom or den complete the first level. As you make your way to the second level you will find a comfortable loft area, an additional bedroom and a full bath. The property's exterior showcases a log architectural style, harmonizing with its natural surroundings. A built-in garage provides convenience and secure parking. For outdoor enjoyment. Rear deck extend the living space, offering venues for relaxation and entertaining. Enjoy rights to Garnet Lake a short stroll down the way!! To truly appreciate the distinctive character and lifestyle offered by this property, a personal viewing is highly recommended.

35 South Rd Ext, Peru

$550,000
73562359 MLS
The offered property comprises 52.35± acres in Richmond, Massachusetts, featuring a varied landscape of wooded acreage and a small open field near the northern portion of the property that provides scenic views to the south and west. The surrounding woodland creates a private setting adjoining the Berkshire Natural Resources Council's Stevens Glen Reserve, known for its maintained trail system and waterfall. Considerable planning and preliminary development work has already been completed, including six percolation tests, survey and land-planning documents, and a town-approved shared driveway permit. Existing plans identify potential locations for at least two building lots, with the possibility of a third, providing a future owner with a valuable framework for evaluating building sites and access while retaining flexibility in the property's ultimate design. Property is subject to Ch 61 Forest lien.

206 Stevens Glen Rd, Richmond

$325,000
3 Beds 1 Baths 73561617 MLS
Welcome to this bright and inviting 3-bedroom, 1-bath ranch, ideally located just moments from beautiful Pontoosuc Lake on a spacious double lot. This home features a generous living room with oak hardwood floors, a formal dining room, and an updated kitchen with newer countertops. Additional highlights include a spacious basement with abundant storage, an oversized one-car garage, and an enclosed seasonal porch-the perfect place to relax. The fully fenced backyard offers plenty of space for gardening, entertaining, pets, or simply unwinding. Conveniently located near the lake, shopping, dining, and local amenities, this home offers the perfect blend of comfort, convenience, and outdoor living.Enjoy the convenience of living just moments from Pontoosuc Lake Park, where boating, swimming, kayaking, canoeing, picnicking, and breathtaking sunsets can become part of your everyday lifestyle. One of Pittsfield's most popular recreational destinations, the park also features a public boat ramp and picnic areas.Ideally situated in the heart of the Berkshires, this home is just minutes from downtown Pittsfield, Onota Lake, Jiminy Peak Mountain Resort, scenic hiking trails, museums, acclaimed theaters, restaurants, shopping, and the region's year-round cultural and outdoor attractions.Whether you're looking for a year-round residence or a relaxing Berkshire retreat, this light-filled home offers the perfect blend of comfort, convenience, and outdoor recreation in one of Pittsfield's most desirable lake-area neighborhoods. Don't miss this wonderful opportunity to enjoy the best of Berkshire living.

296 Hancock Rd, Pittsfield

$158,900
2 Beds 1 Baths 73560750 MLS
Welcome to 186 Burbank Street! This charming colonial-style home offers two bedrooms, one full bathroom, and 1,158 square feet of living space. Situated on a level corner lot in an established residential neighborhood, the home features a functional layout with plenty of potential. The main level includes a spacious kitchen with ample cabinet and counter space, a formal dining room, comfortable living room, and full bathroom. Upstairs, you’ll find both bedrooms. A full basement provides plenty of additional storage, while the attached garage and private driveway offer convenient off-street parking. Conveniently located near Silver Lake, Lakewood Park, shopping, dining, and other local amenities. Bring your ideas and make this Pittsfield home your own! This property is eligible under Freddie Mac First Look Initiative through 09/06/2026. Only owner occupant, non-profit and Neighborhood Stabilization Program (NSP) offers will be reviewed and considered.

186 Burbank St, Pittsfield

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