RARE OFFERING! This well maintained, charming 3BR home features an expansive 5-car garage/workshop setup, offering endless possibilities for automotive, electrical, woodworking, crafting projects; equipment storage, or home-based hobbies. Boasting approx. 1,094sf of 1-level living space living space with its original character intact, it offers an excellent opportunity for updates and personalization. The full, dry basement adds valuable flexible space for recreation, a home gym, workshop, family room, or additional storage. This property features prime amenities, including a huge, private backyard; a large, enclosed patio; and accessible ramp transitions. Don't be deceived by the drive by, you must come inside to appreciate this remarkable home! Call today for your private showing.

Set on more than 15 beautiful acres, this exceptionally well-maintained three-bedroom, two-full-bath home offers comfort, privacy, and abundant outdoor space. Highlights include a new metal roof installed in 2025, an outdoor shower, and an enormous new deck ideal for relaxing and entertaining. The home also features a full basement that is exceptionally neat and dry, providing excellent storage and additional possibilities. Enjoy a peaceful country setting just 20 minutes from the Massachusetts Turnpike entrance in Lee, as well as the town's many restaurants, shops, and everyday conveniences.

UNIQUE OPPORTUNITY TO HAVE A SPACIOUS FAMILY HOME WITH HIGH VISIBILITY FOR A HOME OFFICE OR BUSINESS. THOUSANDS OF VEHICLES WILL SEE YOUR BUSINESS SIGN AND YOUR OFFICE WILL HAVE A PRIVATE ENTRANCE. PERFECT FOR SOMEONE IN THE TRADES, IE; CONTRACTOR, PLUMBER, ELECTRICIAN AND ALSO PROVIDING A LARGE FAMILY LIVING SPACE WITH A PRIVATE BACK YARD. COME SEE FOR YOURSELF.

Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully reimagined library/office, dining, living media/den and kitchen. First-floor primary suite serves as a private retreat, while additional en-suite bedrooms provide comfort and discretion for guests. An upper-level loft (w/ elevator)offers space for gym, studio, or media. A rare offering of privacy, design, and distinction in the Berkshires.

This recently renovated cottage, set on 4 woodland acres in beautiful Monterey enjoys close proximity to Lake Garfield, for boating and swimming, and plentiful hiking trails throughout the town. With 750 square feet of bright, clean, efficient living space, and a large detached garage, the cottage is the perfect Berkshires getaway. Recent upgrades include a spacious deck, interior painting, a refurbished bath and partially fenced back yard. Truly a little gem in the woods! Offered fully furnished. Move in for the Summer!

Ideally located in desirable street in Lee, this well-maintained Cape blends classic charm with thoughtful modern updates. Surrounded by beautiful landscaping, the home features 4 bedrooms and 2 full baths, including 2 bedrooms and a full bath on the first floor for convenient one-level living. The updated 2022 kitchen offers granite countertops, modern appliances, and stylish finishes. Recent improvements include new windows, doors, and boiler. Enjoy warm wood floors throughout, a gorgeous wood-burning fireplace, and a generously sized partially finished basement for added living or recreational space. Relax on the spacious backyard deck overlooking the landscaped yard. An oversized 2-car garage provides ample storage and workspace.

Charming cottage-style home that offers far more space than meets the eye! The first floor features a spacious kitchen with abundant cabinet storage, pantry space, and a newer gas range, along with a cozy office nook, dining room, living room, full bath, two bedrooms, laundry room, and an inviting den. Upstairs offers three additional rooms, including two bedrooms, providing flexible space for guests, hobbies, or a home office. This home has seen many updates since 2019, including a new furnace, oil tank, front siding, and all new windows on the front of the house. Beautiful hardwood floors were added in the living room, dining room, and first-floor bedrooms, while the kitchen, laundry room, and den feature durable new laminate flooring. Additional highlights include a walk-out basement

Perched high above a serene, bucolic country setting, this warm and inviting three-level home perfectly blends private seclusion with everyday convenience. Offering spacious open-plan living, the home features a dramatic, floor-to-ceiling stone fireplace in the great room that anchors the space with timeless rustic elegance.The seamless flow connects the living area, dining space, and kitchen--ideal for both quiet evenings and effortless entertaining. Just off the first-floor primary suite, a dedicated hot tub room offers a private year-round retreat. Upstairs, an open office loft looks down over the great room, accompanied by two guest bedrooms and a full bath. The walk-out lower level expands your living space with a large family room and laundry room,complemented by abundant storage

A Landmark Berkshire Estate of Extraordinary Provenance. Set on 15 private acres in the heart of the Berkshires, a rare American legacy estate commissioned in 1847 as the summer residence of renowned physician, poet, & author Oliver Wendell Holmes Sr. Two centuries later, this extraordinary property remains a testament to architectural elegance, literary heritage, & timeless craftsmanship. The offering preserves original hardwood floors, intricate millwork, & the grandeur of a distinguished era. Its storied halls welcomed literary icons including Longfellow, Melville, & Hawthorne. Surrounded by exceptional privacy, Holmesdale is more than a residence, it is an irreplaceable American landmark and a rare opportunity to become the next steward of Berkshire history.

This log home in Leisure Lee offers two bedrooms and one bathroom in a woodland setting with authentic character. Built with natural woodwork throughout, the property provides a retreat for those seeking genuine timber construction with established community appeal. Inside, the kitchen anchors the dining room, with a rear addition for a family room. While a loft adds functional sleeping or storage area above. Wood finishes carry through the interior, reinforcing the home's authentic aesthetic. A private deck extends the living area outdoors, ideal for morning coffee or evening relaxation overlooking the property. The setting includes access to Goose Pond and tennis courts within the community, offering recreational opportunities for residents.

Rare opportunity to acquire a updated two-family property in Stockbridge with nearly 1.9 acres across two included lots. Come take a look to add your finishing touches to this project. Situated on a dead-end street on a spacious and clear lot. Each unit features three bedrooms and one-and-a-half baths, across approximately 2,700 square feet. Separate utilities for each unit, off street parking, and two new heating systems are ready for installation. Extensive recent updates include a new roof, renovated kitchens, updated flooring, and fresh interior/exterior paint. Conveniently located near downtown Stockbridge, the property offers easy access to some of the Berkshires' most recognized cultural destinations, including Tanglewood, the Norman Rockwell Museum

Discover the timeless appeal of this beautifully renovated mid-century modern split-level home, thoughtfully designed across four spacious levels. Offering two bedrooms and two full bathrooms, this unique property features flexible living space with the potential for a third bedroom, home office, family room or hobby space to suit your needs. The stunning living room showcases soaring vaulted ceilings, hardwood floors, expansive windows and a french door leading to the deck, creating an open and inviting atmosphere. Situated on two scenic acres with breathtaking mountain views, this property offers the perfect blend of privacy and tranquility. Recent and extensive renovations provide a stylish move-in ready

Immaculate 3-bedroom ranch with additional 750 square feet of finished living space in lower level. Move in condition, cathedral ceiling in living room and 2 full baths, Master with ensuite. Set way back off Park Street North on 0.62 level acres. 8+ acres owned by Land Conservation in your back yard adds peace and privacy.

This immaculate Lion's Head condominium is a perfect pied a terre or weekend residence. The inviting living room features custom shelving, a propane fireplace, and sliders to a private deck overlooking a wooded setting. The updated kitchen is equipped with stone countertops, and high-end Bosch appliances, including a range and microwave/convection oven. A dining area with vaulted ceiling and skylight adds to the bright, airy feel. Upstairs, both bedrooms feature vaulted ceilings and new windows. Additional highlights include central air, engineered wood flooring, and attached one-car garage. Lion's Head amenities include a Gunite pool and tennis court and its central location allows for easy access to town. Near private schools, restaurants, and Metro-North at Wassaic. A true gem!

Over 30,000 square feet of Commercial Property in the heart of Great Barrington. Ideal Route 23 location, adjacent to the retail-commercial district and CSX Freight Rail Line. Currently consisting of 5 Structures (13,233 sq.ft, 6,600 sq.ft,, 4,000 sq.ft., 5,000 sq.ft. & 1,554 sq.ft.) with ample on-site parking. Previously used by a major Plumbing Distribution and Warehouse Company. Use 'as is' or create new structures on this 1.63 Acre Parcel. Mixed Zoning. Public Water & Sewer.