Step into history with this captivating 4-bedroom, 3-bathroom single-family home, offering 2,288 sq. ft. of living space. Built in the 1860s, this residence exudes charm while incorporating numerous modern updates for contemporary comfort. Nestled on a quarter-acre lot in a quiet town, this home boasts a lush yard and a fully screened-in porch, perfect for enjoying serene mornings and tranquil evenings. The spacious rooms provide versatility and ample living space, while abundant storage. A standout feature is the standalone two-car garage. Experience a unique blend of historic elegance and modern luxury in this remarkable property--an ideal sanctuary for those seeking a peaceful, yet connected lifestyle

An updated commercial condo in a prime location! This versatile space features flexible layout options, and abundant natural light--ideal for office, retail, or professional use. Situated in a high-traffic area with excellent visibility and easy access to major roads and public transit. Perfect for businesses seeking a polished, move-in-ready space in a thriving commercial hub.

Charming Renovated Cottage on The Hill - Great Barrington, MADiscover this beautifully renovated Four Square-style cottage in the heart of Great Barrington's coveted ''The Hill'' neighborhood--a rare pied-a-terre offering classic charm with modern upgrades. This delightful 2-bedroom home is nestled in the Southern Berkshires, just moments from downtown, Lake Mansfield, and preserved natural areas.Step inside to a brand-new kitchen, freshly painted interior, and hardwood floors throughout. All windows have been upgraded to energy-efficient Anderson, enhancing comfort and style. The exterior has been professionally repaired and painted. A newly fenced garden provides a private oasis, while dedicated off-street parking ensures convenience.

An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could be a private primary 1st floor suite. The current owner has solid Air BnB income from it as is, or it could be rented year-round. The fully insulated barn/garage has it's own 100-amp service and is currently being used as a woodworking shop. A wood stove and a large loft for storage adds to its utility.

Don't miss this charming 4-bed, 2-bath home with 2 first-floor bedrooms and a full bath! Offering nearly 2,100 sq. ft. of living space and almost 1 acre of flat, dry land, this home provides plenty of room to grow. The breezeway connects the 2-car garage with newer doors and electric openers. Outside, enjoy a private patio, stone wall, and a shed for extra storage. The home has also just had the exterior fully painted. Gorgeous flowering crabapple trees grace the front yard. This beautiful home blends comfort, convenience, and outdoor charm--schedule your visit today!

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.

Tucked away in a walkable east-side neighborhood of Great Barrington, this custom 3-bedroom bungalow is anything but ordinary. From the moment you step inside, the care and creativity in every corner are impossible to miss--handcrafted woodwork, thoughtful built-ins, and artful finishes infuse the home with a personality all of its own.The inviting and cozy open floor plan make everyday living feel effortless, while abundant natural light fills the spaces. At the heart of the home, the kitchen stands out with its custom copper countertops, reclaimed wood shelving, and clever storage solutions for functionality.Step outside to your own private oasis: a fully fenced yard with seven 20-foot no-till garden beds, ready for your homesteading dreams or a vibrant

This is a spacious house with generously sized rooms 5 minutes from town. 4 bedrooms with 1 full bath, 2 3/4 baths and one powder room. First floor has kitchen, living room, dining room, pantry, laundry and a generous master suite with sitting area, office space and full bath. Second floor has 3 bedrooms, one with ensuite 3/4 bath. Lots of closets and plenty of storage space with basement storage or workshop area. New 16k oil burning furnace in 2025. for hot water baseboard heat. New septic to be installed by seller this fall.Charmingly surrounded by neighbor's barns, with a nice .45 acre parcel with lawn or ready for your own garden. Screened in porch, patio and fire pit are perfect for summer in the Berkshires.

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, blending classic charm with modern comfort.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.

Welcome to a rare opportunity to own or rent a thriving commercial business that has been family owned and operated since 1966. This unique property offers a range of possibilities, including a full-service auto garage, an auto shop with a two-bay garage, and two separate apartments for rental opportunities. With ample storage for up to six cars and additional parking, this property is a dream come true for entrepreneurs and investors alike. As you step onto the premises, you are immediately greeted by a sense of history and longevity. For over half a century, this gas station and auto service center has been a trusted resource for the local community.

Set on a deep, level one-acre lot, this colonial offers a nice balance of space, privacy, and neighborhood convenience. The front entry opens to an inviting staircase that leads upstairs to three bedrooms and a shared full bath. The main level includes a comfortable living room with a fireplace and back door opening to a covered porch overlooking the fenced backyard and in-ground pool.A bright eat-in kitchen with a back entry sits at the heart of the home, with a nearby half bath and a separate dining room for more formal meals or gatherings.The full basement mirrors the home's footprint, offering laundry and plenty of storage. Additional features include: 1 car garage with covered entry to the house, multiple garden beds, and updated windows.

A rare opportunity to own a versatile 8+ acre parcel in a prime Great Barrington location. Accessed by an established roadway, this property presents a unique canvas for a private estate, a multi-home development, or a commercial enterprise. The property features a substantial 3,000 square foot building with radiant heat. With three large garage bays, an office, and a loft, it can serve as the ultimate workshop for a homeowner, a project headquarters for a developer, or a fully functional base of operations for a business. Whether you are seeking to build your private dream home with an incredible workshop, develop a new neighborhood in a high-demand market, or establish a commercial business, this property provides the space, infrastructure, and flexibility to achieve your vision.

A rare opportunity to own a versatile 8+ acre parcel in a prime Great Barrington location. Accessed by an established roadway, this property presents a unique canvas for a private estate, a multi-home development, or a commercial enterprise. The property features a substantial 3,000 square foot building with radiant heat. With three large garage bays, an office, and a loft, it can serve as the ultimate workshop for a homeowner, a project headquarters for a developer, or a fully functional base of operations for a business. Whether you are seeking to build your private dream home with an incredible workshop, develop a new neighborhood in a high-demand market, or establish a commercial business, this property provides the space, infrastructure, and flexibility to achieve your vision.

Location, location, location! Positioned in one of the highest traffic count areas in the County, this property is near a very vibrant shopping and restaurant area, AND very close to a significant number of hotel/motel rooms. If you are a retailer, this is where you want to be! The utility situation provides more good news; Town Water, Town Sewer, and Natural Gas. Seeing is believing. Call now for a showing.

A prime investment opportunity in the heart of downtown Great Barrington. This 5-unit residential property features a desirable mix of four one-bedroom apartments and one two-bedroom unit. A significant advantage for this building is that all units are serviced by their own separate heating and electrical systems. Its convenient downtown location ensures high demand due to walking proximity to grocery stores and the hospital, while ample on-site parking provides a crucial amenity for all residents. Adding to its value, a detached garage/workshop offers the flexibility to be rented separately for additional income or used as a storage amenity for tenants.

New England farmhouse with distant views. Large common rooms & kitchen great room are bathed in sunlight. Beautiful pine floors & exposed beams throughout the 1st floor. Extra room on the first floor can be used as a bedroom or an office (not pictured.) Many structural renovations in 2004, central air, in line generator, in ground pool, screened porch & so much charm. The flat 3.89 acres allows for accessory buildings, pickleball court, etc. Easy bike ride to town. This is the home you've been looking for.