Incredible Multi-Unit Investment Opportunity in Downtown Pittsfield! Located just steps from the Barrington Stage Company theater in the heart of the cultural district, this dynamic property includes 3 apartments, making it a true income-generating powerhouse. This is a rare opportunity for both the savvy investor and the live-in owner looking to offset housing expenses. The entire property has been newly renovated and is in excellent condition, offering peace of mind for years to come. Each unit has been thoughtfully updated with modern finishes, efficient systems, and attention to detail, making it a turn-key investment with minimal maintenance needs. There are 2 units on the 1st floor (front and back) that are 1 bed/1 bath each, plus the 2nd floor hosts a 2-bed/2 bath on the 2nd level.

Welcome to 41 Pearl Street- a 1900s two-family residence nestled on a quiet street just moments from downtown Great Barrington. This spacious 4-bedroom, 2-bathroom (both sides are 2 BR/1 BA) home offers 1,964 square feet of living space on a generous 0.25-acre lot, containing that classic period charm.Step inside to discover a welcoming floor plan with ample natural light, hardwood floors, and period details. The kitchen and living areas are perfect for entertaining or relaxing with family. Upstairs, the bedrooms offer privacy and comfort, with plenty of storage throughout. Warm and efficient forced hot water heating.

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include an oversized curb cut for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success, offering a generous footprint for a new building envelope, with an additional building site also available for an additional fee. The site is ideal for a high-volume business such as a drive-through (QSR, bank, coffee), retail store, or professional offices. Leverage the robust, year-round economy of the Berkshires, a premier destination for tourists and residents.

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include an oversized curb cut for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success, offering a generous footprint for a new building envelope, with an additional building site also available for an additional fee. The site is ideal for a high-volume business such as a drive-through (QSR, bank, coffee), retail store, or professional offices. Leverage the robust, year-round economy of the Berkshires, a premier destination for tourists and residents.

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include an oversized curb cut for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success, offering a generous footprint for a new building envelope, with an additional building site also available for an additional fee. The site is ideal for a high-volume business such as a drive-through (QSR, bank, coffee), retail store, or professional offices. Leverage the robust, year-round economy of the Berkshires, a premier destination for tourists and residents.

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include an oversized curb cut for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success, offering a generous footprint for a new building envelope, with an additional building site also available for an additional fee. The site is ideal for a high-volume business such as a drive-through (QSR, bank, coffee), retail store, or professional offices. Leverage the robust, year-round economy of the Berkshires, a premier destination for tourists and residents.

Settle into the quiet charm of the Windemere Lake community with this 7.166-acre building lot. Tucked away on a peaceful road and embraced by natural woodland, the property offers a sense of seclusion while remaining part of a thoughtfully maintained private enclave. Though it doesn't sit directly on the water, owners enjoy shared access to Windemere Lake—a pristine, non-motorized lake perfect for kayaking, swimming, and unwinding in nature. Build your dream home in a setting where sunsets glow through the trees and the pace of life slows to match the stillness of the lake.

OPEN HOUSE SATURDAY 7/18 11:00-1:00. PM. Beautiful Amish 2021 built log sided home for the ultimate weekend getaway set on a private 3/4 acre lot. Move in ready - all interior & exterior furniture to remain. Beautiful outdoor living space with a masonry fireplace under a timber framed pavilion. Very energy efficient cabin, cool in the summer, cozy in the winter. Energy features include solar panels on the roof, mini splits for heat & AC, charging station for EV, ceiling fans plus a wood stove in the living area. Also available to purchase separately: an undeveloped half acre lakefront lot with 170'' on the water - a short walk from the house. For feature list please refer to supplement or documents tab.

Settle into the quiet charm of the Windemere Lake community with this 8.592-acre building lot. Tucked away on a peaceful road and embraced by natural woodland, the property offers a sense of seclusion while remaining part of a thoughtfully maintained private enclave. Though it doesn't sit directly on the water, owners enjoy shared access to Windemere Lake—a pristine, non-motorized lake perfect for kayaking, swimming, and unwinding in nature. Build your dream home in a setting where sunsets glow through the trees and the pace of life slows to match the stillness of the lake.

Rustic Contemporary in Otis Wood Lands that abuts the State Forest! This cozy home has an open concept kitchen/living/dining area with vaulted ceilings. Access the screened-in porch and deck from the sunken living room. Primary bedroom with skylight and deck access. Detached two-car garage with space above for artist's studio. An easy-to-maintain property. Association amenities include tennis/pickleball courts, pool, fitness room, clubhouse, playground, lake and beach area. $4,000 reserve fund fee due from buyer at closing. Wood stove disconnected prior to closing.

Welcome home to this peaceful & serene 3 bed, 2.5 bath contemporary offering an open floor plan, main-level primary suite, & a private trail leading to the wild streambed of Glendale Brook! The main level features a spacious living rm & dining area w/ propane stove & sliders to a sunny deck, a kitchen w/ pantry closet, half bath w/ laundry, a first-floor office, & a primary bedroom w/ ensuite bath featuring a jetted tub & shower. The lower level provides flexible living w/ a 2nd office, bonus room, 2 beds w/ forest-facing windows, a shared recreation area, kitchenette, full bath & a built-in sauna! An exterior door opens to private trail along Glendale Brook, leading to a natural dipping pool. Additional features include 2 separate meditation rooms w/ own entrances, & a newly replaced furn

Contemporary two-bedroom home privately situated on just over two wooded acres with a spacious lawn. The main level features an open-concept kitchen and living area with cathedral ceilings, two bedrooms, a full bath, and an open loft ideal for a home office or additional living space. The finished lower level offers a flexible living area that could serve as a guest room or bedroom, a full bath, and a kitchenette with sink that also functions as a convenient mudroom. Electric heat, a wood stove for supplemental warmth, and a mini-split providing heat and A/C on the main level ensure year-round comfort. Additional features include new exterior decks, 200-amp electrical service, ample basement storage, and an automatic generator.

Step into effortless Berkshire living in this design-forward mid-century ranch. Perfectly positioned on a quiet downtown dead-end road, this 3-bedroom, 1-bathroom home seamlessly blends crisp, modern style with classic architectural character. Inside, original hardwood floors guide you through a bright, fluid one-level layout. The living room serves as a comfortable anchor for cozy mountain evenings, featuring a striking wood stove that pairs perfectly with the home's fresh, stylish aesthetic. Outside, the generous 0.41-acre level lot offers a private, shaded yard surrounded by mature trees-a fantastic feature for a property this close to the action. Beyond its residential charm, this property boasts coveted Business zoning, making it perfect for an ideal live-work lifestyle.

Home on over 7 secluded acres framed by mountains and backing to the Chalet Wildlife Management Area (7,000+ acres of protected state land). Enjoy total privacy, wide-open views, and dark-night skies away from city lights. Step inside to a grand entrance with a glistening chandelier. The main level features a flowing layout: a spacious kitchen with sufficient storage and generous counter space leading to the bright living room. Another feature on the first floor is that there is an option for private living quarters/in-law suite with its own entrance. The large primary suite offers a cozy fireplace, two walk-in closets, and an en suite bath with shower and jetted tub. Additionally, there is a first-floor laundry off the two-car garage, and an extra room great for an office. Needs TLC.

Set on 16 private acres, this four-bedroom, one-and-a-half-bath home has been lovingly updated while preserving its rustic warmth and character. Soulful wood floors, cozy living spaces, and a versatile attic retreat give this home an authenticity you simply cannot manufacture. A two-story wood stove heated barn bursting with natural light makes for an ideal studio or creative workspace. Step outside to a spring-fed pond reaching ten feet at its deepest and perfect for a summer float, a morning swim, or simply watching the light dance across the water. A gazebo offers a quiet perch to read, sketch, or simply breathe it all in. And when the day calls for deeper restoration, a private sauna awaits. Close to Jacob's Pillow, Becket Arts Center, Lee, and Tanglewood. A true sanctuary.

Discover the perfect mountain retreat in this beautifully maintained 2-bedroom, 2 full bath condo offering 1,030 square feet of comfortable living space. Ideally located just moments from the ski slopes, this home is a dream for outdoor enthusiasts and year-round adventurers.Enjoy easy access to a wide range of community amenities, including a heated pool, tennis courts, and beautifully maintained grounds. Whether you're hitting the slopes in winter, enjoying summer recreation, or simply unwinding in a peaceful setting, this condo offers the ideal blend of convenience and lifestyle.Perfect as a primary residence, vacation getaway, or investment property, this is your opportunity to own a slice of mountain living at its best.

Ready to build! Build your own Berkshire Home on this beautiful 3.44 acre parcel in the heart of the Berkshires! The land is partially cleared and ready for construction, with septic design plans already with public water and power on the street. Set on a quiet road, this property offers privacy with a true Berkshire feel while being close to many cultural attractions including, Tanglewood, The Mount, Ventfort Hall, great restaurants & shopping with seasonal fun such as Bousquet, summer concerts and more!

This is a ''niche home'' in a ''niche location'' so the seller's have lowered their price to bring in more buyers! Come check out this spacious home on 1 acre in Windsor MA! A welcoming formal living room and separate formal dining room set the tone for refined entertaining, while a huge party room featuring a full bar and cozy fireplace is perfect for gatherings, game nights, or hosting large events. Bright, open kitchen has pasture views, a gas stove and white cabinets! Heated enclosed front porch is perfect for the entry catch all space! The house is set nicely back from the road with a 3 car detached garage and a circular driveway. Central Berkshire Schools. Windsor residents receive Notchview passes for cross country skiing - and it's right out your back door!

Move-in ready 3 bed/3 bath spacious Dalton Ranch offering room to spread out both inside and out. The renovated kitchen and dining area feature granite countertops, peninsula seating, SS appliances, and opens nicely to the main living spaces. Hardwood floors run throughout the home, with generously sized bedrooms and a large living room with bay window and fireplace. The finished lower level adds significant bonus space with a built-in bar, fireplace with pellet stove insert, half bath, and additional flexible areas. Outside, enjoy a covered deck and above-ground pool in a private backyard setting. Additional features include solar panels for energy efficiency, generator hookup capability, 2-car attached garage, circular driveway, French drain system, & new furnace and hot water heater.

Yes, the Jim's House of Shoes building is for sale! Great location in the heart of North St, downtown Pittsfield. 4 large front display windows, 3 entrances and exits, full, usable 5,500 sq. ft. basement with inside access. Start a business here; move a business here; be part of Pittsfield's rejuvenation!