A rare c.1780 estate poised for a spectacular second chapter. Perched above the village of Monterey, Ledgehurst offers a canvas for the ultimate Berkshires compound: a main house with room to create the private, en-suite retreat of your imagining, an indoor pool and sauna complex ready to be reborn as a true wellness escape, plus two barns that open the door to possibilities few properties can match. A guest house, a creative studio, a multi-generational haven; the vision is yours to shape. With over an acre of grounds, a short stroll to Lake Garfield's sandy beach, and downtown Great Barrington just 15 minutes away, this is a once-in-a-generation opportunity to bring true Berkshires living to life. Sold as-is; buyers encouraged to perform due diligence on scope and permitting.

Set on 21.5 acres at the end of a long, winding private drive, this extraordinary residence is a true architectural gem--where art, landscape, and modern living converge. Originally designed by Robert McMahon and built by Lou Boxer and later reimagined through a contemporary project by Deborah Reiser of the award-winning RUR Architecture with Hird Design and Construction as the builder, the home reflects a sophisticated, transitional approach to residential architecture and interior design. With five bedrooms and four baths, the home is defined by its dramatic walls of glass, seamlessly framing bucolic country views, a classic red barn, and thoughtfully designed gardens. Natural light pours into every space, creating an ever-changing connection to the surrounding landscape. The kitchen is

Beautiful property in a bucolic setting with sprawling front flower gardens! The main floor boasts a first floor primary with en suite bath, open kitchen with fireplace, dining room with built ins and access to the oversized deck, great room with beautiful wood floors and doors that lead to the serene screened porch, cozy den with fireplace, office/flex space and half bath. The second level includes two guest bedrooms and a full bath with washer and dryer. Truly a special offering.

Nestled among spectacular rhododendrons that burst into bloom each spring, this architect-designed contemporary home offers a seamless blend of natural beauty and timeless mid-century modern inspiration. Designed byarchitect Andrew Daland, the residence features expansive windows that frame peaceful pastoral views and fill the home with natural light. Designed for comfortable one-level living, the main floor includes the primary living spaces, while the lower level provides exceptional accommodations for family and guests with two bedrooms each with en suite full baths, and a spacious family room. The open-concept great room boasts a cathedral ceiling, a fireplace, built-in bookcases, and flows effortlessly into the kitchen. . . .

COMMANDING VIEWS OVER LAKE GARFIELD WITH A STUNNING MOUNTAIN BACKDROP, this beautifully updated home offers charm with modern refinement. Original architectural character has been thoughtfully preserved, while expansive windows fill the home with light and frame the breathtaking scenery. Recently renovated chef's kitchen, first floor primary bedroom, and loads of closet space address today's needs. And could there be any better spot to watch sunsets than the expansive front porch? What's more, a well-appointed suite in the separate carriage house offers flexible space for guests, a home office, or artist's studio. Features include eight private acres, high speed internet, low Monterey taxes, and proximity to the Monterey bathing beach and the incomparable tomatoes at Anna's farm stand.

Welcome to this charming 3-bedroom, 1.5-bath ranch home in Pittsfield's highly desirable Orchards neighborhood. Comfortable single-level living features warm wood floors through the main living areas and all bedrooms, a classic kitchen with vintage wood cabinets, and a bright sunroom with sliding doors from the kitchen. The primary bedroom includes a convenient private half bath. A practical laundry/mudroom connects the home directly to the attached one-car garage. Downstairs, a large dry family room complete with a pool table offers fantastic extra living and entertaining space. Major mechanical updates include a brand-new boiler, a roof that is approximately five years old, and easy-care vinyl siding.

VERMONT! Located close to 1,000's of acres of Green Mountain National Forest! A little piece of Vermont just waiting to be discovered! Tucked into nearly 13 surveyed acres of woods, this charming 1970s ranch offers the peace, privacy & simplicity so many look for. A stone wall outlines the parking area, with stone steps leading up & into the front screened in porch that overlooks the yard & meadows. Inside, you'll find 2 bedrooms, wood floors, built-in bookshelves, dining room that opens to kitchen & a large, bright living room featuring a stone fireplace with wood stove insert--perfect for cozy evenings after a day outdoors. The screened porch & back deck add wonderful spots to relax & enjoy the peaceful surroundings. The property is being sold as-is, with furnishings included (see more)

This property offers a great opportunity for someone ready to renovate and make some repairs while adding their own personal touches. The first floor features a living room, dining room, kitchen, and two additional spaces that could be used as bedrooms, offices, or whatever suits your needs. Upstairs, you'll find three bedrooms and a full bath, with a walk-up attic providing even more space and potential. The furnace and roof are both under 10 years old. Outside, enjoy a great yard and a garage that offers convenient storage. If you've been looking for a project with plenty of possibilities, come take a look! Property is being sold AS IS with all contents remaining.

Space, convenience, and an expansive backyard and deck with an above-ground pool come together at 26 Harvard Street! This inviting three-bedroom, one-bath home offers an open floor plan with the living room, dining room, and kitchen flowing seamlessly together. The updated bathroom features an oversized walk-in shower. Vinyl siding and a generously sized, FULLY FENCED backyard provide plenty of space to enjoy the outdoors, garden, play, or entertain. Conveniently located close to Pittsfield's shopping, dining, parks, schools, and other amenities. If you're looking for a home with room to spread out, a private fenced yard, and the opportunity to make it your own, come see the possibilities at 26 Harvard Street!

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26.

SPACIOUS, SINGLE-LEVEL CONTEMPORARY WITH PRIVACY AND HEATED IN-GROUND POOL in the coveted community of Harrington Woods. 6 bedrooms. 3.5 baths. Bright, open floor plan with a spacious kitchen open to the dining area. The Great room has a cathedral ceiling, a wood-burning fireplace, and glass doors leading to a large screened porch and deck. Primary bedroom suite with full bath has cathedral ceiling and glass doors leading to the deck. Finished walkout lower level is perfect for a gym, playroom, game room. In-ground heated pool surrounded by perennial gardens. Access to a community pool, and a tennis/pickleball court. Miles of hiking trails in the area and 15 minutes to swimming at Lake Garfield or kayaking at Lake Buel. 20 minutes to Ski Butternut. 10 minutes to Jacob's Pillow.

Build your dream home in the heart of the Berkshires! Builder's flat lot located in a PRIVATE country community. Yearly fee @ See document tab-@$575 yearly is for road & snow maintenance, insurance & reserves. Great location for full time or vacation residence. Owner is a licensed contractor who can build custom build exactly what your looking for!This property offers the connivence of an APPROVED septic design with designated well and septic locations, helping to save time and expense during the building process. Surrounded by nature,the lot provides a peaceful setting while remaining close to hiking, lakes, sking,and all the cutural attractions the Berkshires is know for. Whether you are planning a year-round residence or a weekend getaway, this property is ready for your vision!

Charming In-Town Cape on a Spacious Lot with Inground Pool. Located in a delightful neighborhood close to town. This inviting home built in 1951 offers 5 bedrooms & 2 full baths. Inside, the residence seamlessly balances ample room to spread out with warm, light-filled spaces tailored for everyday living & entertaining. Timeless architectural details throughout bring character & charm, including a wood-burning fireplace, graceful arched doorways & custom built-in cabinetry. Outdoors, a private in-ground pool is set within a large, sunny yard, creating a wonderful oasis. Turn-key peace of mind is provided by recent upgrades, including a newer including a newer furnace, water heater & pool filter. Town water, town sewer & natural gas from the street. Close to everything - A must see!

Stunning architect designed space with soaring ceilings, floating staircases and numerous high-end features. Ideally situated on nearly ¾ acre abutting an 18-acre nature reserve. Just a short walk to downtown Lee shops and restaurants. Lots of room for a pool, tennis court, and/or pickleball court. Minutes from the best places in the Berkshires. Great investment opportunity with the nearby $100 million Eagle Mill development. Lots of room with 4,000 square feet of living space plus a separate 2,500 square foot area with large stained glass windows to create a second dwelling unit, studio, chapel, gym, office, or entertainment extravaganza. Combining the best of new construction with old charm, you need to view this amazing space to experience its magnificence!

Stunning architect designed space with soaring ceilings, floating staircases and numerous high-end features. Ideally situated on nearly ¾ acre abutting an 18-acre nature reserve. Just a short walk to downtown Lee shops and restaurants. Lots of room for a pool, tennis court, and/or pickleball court. Minutes from the best places in the Berkshires. Great investment opportunity with the nearby $100 million Eagle Mill development. Lots of room with 4,000 square feet of living space plus a separate 2,500 square foot area with large stained glass windows to create a second dwelling unit, studio, chapel, gym, office, or entertainment extravaganza. Combining the best of new construction with old charm, you need to view this amazing space to experience its magnificence!