Four-family investment opportunity that checks all the boxes! Great location. Fully rented. Turnkey. Robust net operating income. This well-maintained home, comprising three 2-bedroom units and one 1-bedroom unit all with separate utilities, is an instant profit generator and offers real value in today's market.

Nestled in the sought-after Orchards neighborhood, this beautifully upgraded 3-bedroom, 3-bath raised ranch offers refined living with a bright, open layout and timeless Craftsman details throughout. The fireplaced living room showcases hardwood floors and custom built-ins, seamlessly connecting to the dining area, ideal for both everyday living and entertaining. The refreshed kitchen features quality finishes, generous cabinetry, and thoughtful design. The primary suite is a true retreat, complete with a private bath and an expansive walk-in closet. Two additional bedrooms and a well-appointed laundry room are located on the lower level. Step outside to a new deck overlooking a spacious, flat, fully fenced yard that backs to tranquil woods, providing exceptional privacy.

Proudly offered for the first time, this well-cared-for one-owner Colonial is set in a highly desirable neighborhood on corner lot. Offering 4 spacious bedrooms and 2.5 baths, the home features gleaming hardwood floors and a classic, timeless layout ideal for both everyday living and entertaining. Step outside to a large, lush backyard perfect for relaxing, play, or gatherings. Thoughtfully maintained over the years, this home combines warmth, space, and location, presenting a wonderful opportunity to enjoy a true neighborhood setting in a home that has been genuinely loved. Natural gas, multi zoned heating, and underground utilities.

Discover the ideal setting for your next home or retreat on this 15-acre parcel in West Pittsfield. Thoughtfully prepared, the property already features installed electricity, along with a newly constructed driveway and building pad. Enjoy a perfect blend of open and wooded land, including 5+ acres of fields, 10 acres of forest, and approximately 700 feet of road frontage.With city water, multiple perc-tested building sites, and beautiful mountain views, this property offers exceptional flexibility for development. Perfectly situated between Pittsfield State Forest, Onota Lake, and Pontoosuc Lake, and only five minutes to downtown Pittsfield, this is a rare opportunity to own a substantial piece of land in one of Pittsfield's most scenic areas.

*Brand new roof January 2026* Beautifully renovated multi-use building has multiple possibilities. From office space, Dental or Medical offices to Residential. Centrally located and just minutes to downtown Pittsfield and all Berkshire cultural venues. This fabulous building has been updated with modern amenities and chic decor! This property offers an enormous kitchen area with washer & dryer, 6 bedrooms, 3 full baths, 4 fireplaces and oversized spaces that flow from one room to the next. Superb for entertaining large groups! Flooded with natural light. Original hardwood flooring and quality craftsmanship throughout. New mechanicals & electric.Nothing to do but move in! Has outstanding Rental history as well! Ample private parking in rear of building.Being sold completely turnkey.

Beautifully Renovated Prime Investment Property, centrally located and just minutes to all Berkshire cultural venues. With the most updated chic decor, this downtown multi-use property has rental success with local corporations. This stately victorian has been tastefully updated with modern amenities. Offering 6 bedrooms, 3 Full baths, 4 fireplaces, expansive common areas, oversized renovated kitchen with 2 refrigerators. Rooms are complete with high end furnishings and appointments. Lovely huge spaces flow from one room to the next, with plenty of natural light. Original hardwood flooring and quality craftsmanship throughout. Ample private parking in the rear of the property. New mechanicals and electric. Investors can hit the ground running in this '''Turn Key'' Investment property

Turnkey 166.7 kWAC solar field on 1.25 surveyed acres in Pittsfield, MA. Ground-mounted, fully owned system with 784 panels, 5 SolarEdge inverters, and direct grid tie-in via oversized 400A service. Averaging $141K/year in gross income from energy sales and SREC credits. Minimal operating costs, transferable SREC II program (through 2027), and included spare components. Ideal for investors seeking reliable clean energy cash flow with future potential for residential development. No leases--fully owned land with easements in place. Once in a lifetime fully operating solar purchase. Would be an excellent investment. With right terms seller is also willing to hold paper.

From the moment you turn the corner into this highly sought-after neighborhood, you'll feel a sense of belonging. The quiet streets lead you to a home that stands with a classic split-level silhouette--a design built for both privacy and togetherness. A bright welcome as you step through the front door, the first thing you'll notice is the radiance. The generous living room lives up to its name, acting as a sun-trap where massive windows invite the outdoors in. The freshly painted walls catch the morning light, creating a crisp, airy canvas that makes the entire home.... want more of the story ? Schedule a showing today!

This well-cared-for colonial home has been cherished by the same owners for over seven decades and is ready to welcome its next chapter. The first floor offers a spacious layout with a large kitchen, dining room with access to a seasonal porch, a living room featuring a wood-burning fireplace, a family room with half bath, and a four-season sunroom surrounded by windows overlooking the backyard. Upstairs, the primary bedroom impresses with double closets and a vaulted ceiling, complemented by three additional bedrooms and a full bathroom. The fully finished basement provides valuable extra living space with a laundry room, 3/4 bath, and game room. Recent updates include a new roof (2021), heating system (2023), and refinished floors with fresh paint (2025).

AMAZING 3 Bedroom, 2.5 Bath Contemporary in a Wonderful South Pittsfield Neighborhood! Immaculate inside and out, this home offers an open, bright floor plan perfect for everyday living or a second home retreat. Enjoy beautiful wooded views from the rear Trex deck, fireplaced family room, and kitchen. The new granite kitchen features wood floors and flows seamlessly into the main living spaces.The spacious primary suite includes a beautifully updated bath with a large walk-in shower. Additional highlights include a gas fireplace, oversized 2-car garage, fenced yard with wooded land abutting the property for added privacy, and a quiet dead-end street location. A truly move-in ready home in a desirable setting!

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!

Beautifully renovated home with plenty of space for everyone. This home offers 4 bedrooms, 2.5 baths, and a huge yard. Fully finished walkout basement adds another living room, 1/2 bath, and 4th bedroom. There is no sign yet on the property. The sale of this property is contingent upon the seller closing on their next home which is already under contract and scheduled to close on or before April 16th, 2026. Ring camera on the property.

Welcome to 40 Baldwin Avenue with over 2800 square feet of living space. The formal living room flooded with natural light features a pass through, wood burning fireplace. A versatile dining room, presently configured as a den, easily adapts to your needs. An expansive kitchen features ample storage, a desk area and a dining space. Additional first floor living spaces include a family room with fireplace and a mudroom/office area that leads to the newer, trex deck. There is also a full bathroom on the first floor. Located on the second floor are the primary ensuite with a recently renovated bathroom, a third full bathroom and three additional bedrooms, all with double closets. The home also features an aluminum lock shingle roof that is approximately 6 years

Mid-Century Classic with Timeless Appeal: Split-Level RanchStep back in time to the golden era of design with this beautifully preserved 1963 Split-Level Ranch. A true mid-century classic with a lot of character. It's ready for modern-day love and personal touches. This home perfectly blends the clean lines of the Ranch style with the functional, multi-level living of a split-level, offering distinct spaces for every activity. This 4-bedroom home has had multiple updates in the last 4-7years. Windows, roof, driveway & the kitchen with beautiful cabinets, counter tops & stainless appliances. Situated in a great, secluded neighborhood while remaining incredibly convenient--you're just minutes from town centers and all necessary shopping.

Welcome to 582 E New Lenox Rd in Pittsfield. This spacious home offers 5 bedrooms, 2.5 bathrooms, just over 2,000 square feet on the main levels, plus approximately 750 additional finished square feet in the lower level, with bedrooms and baths thoughtfully spread across the home for flexibility and convenience.The bright living room with hardwood floors and a fireplace flows into the dining area and updated kitchen featuring quality cabinetry, stone counters, stainless appliances, and an island with seating. The finished lower level provides great bonus space for a family room, office, gym, or play area.Enjoy beautiful views of Bousquet and a location just a stone's throw to Lenox while still being close to everything Pittsfield and the Berkshires have to offer.

Dottie's Coffee Lounge & Dorothy's Estaminet, a beloved staple in the heart of Berkshire County, is now presenting a rare opportunity for new ownership. Renowned for its commitment to sustainability and locally sourced offerings, this legendary establishment has served as a community hub for food enthusiasts, coffee connoisseurs, and art and music lovers alike. This ethos has cultivated a loyal customer base and contributed to a sustainable community that values the connection between local produce, culinary excellence, and culture. This is more than a business transaction; it's a chance to carry on a legacy that has been an integral part of Berkshire County's fabric. *Sale is for the business & fixtures only-does not include real estate.

Dottie's Coffee Lounge & Dorothy's Estaminet, a beloved staple in the heart of Berkshire County, is now presenting a rare opportunity for new ownership. Renowned for its commitment to sustainability and locally sourced offerings, this legendary establishment has served as a community hub for food enthusiasts, coffee connoisseurs, and art and music lovers alike. This ethos has cultivated a loyal customer base and contributed to a sustainable community that values the connection between local produce, culinary excellence, and culture. This is more than a business transaction; it's a chance to carry on a legacy that has been an integral part of Berkshire County's fabric. *Sale is for the business & fixtures only-does not include real estate.

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

Beautiful, spacious 6 bedroom, 3 updated bath, 4000+sf home, custom built and nestled between two lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota Lake in approximately 9 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, fishing, swimming, picnicking and more. Enjoy the convenience of 2 laundry rooms and two updated kitchens with granite counters and stainless steel appliances. Ample room for the kids and pets to play in the fully fenced in backyard with playset. Enjoy relaxing in the hot tub on the lower level while have shelter from the upper deck! This gorgeous home has all you could need! Surveillance cameras are active outside in the front & back of home.

Two multi-family homes on one lot, a two family and a four family. An apartment in each in needs updating. A short distance to downtown. All separate utilities