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.

This meticulously maintained 1900 farmhouse seamlessly blends timeless historic character with refined modern updates, creating a move-in ready retreat just minutes from the vibrant energy of downtown Great Barrington. Every corner of this classic three-bedroom, two-bathroom home reflects thoughtful care and craftsmanship, offering an ideal balance of warmth, functionality, and quintessential Berkshire charm. At the heart of the residence is a stunning cook's kitchen, thoughtfully renovated and fully outfitted with updated appliances, expansive counter space, and storage. Sunlit living spaces flow naturally throughout the main floor, showcased by rich, beautifully preserved wood floors that anchor the

Set in a peaceful West Pittsfield neighborhood, 35 Meadow Ridge is a sophisticated contemporary home with spacious thoughtfully designed living. Soaring 12 foot ceilings and cherry hardwood floors welcome you inside. The main level features a family room with built-ins, living room with gas fireplace, dining room, eat-in kitchen and access to the outdoor deck. The second floor offers an expansive primary suite, 2 additional bedrooms, 2 full baths, and flexible fourth room for use as bedroom, den or gym.A finished walk-out basement includes a family room and ensuite bedroom adding valuable space. This versatile home offers exceptional comfort and flexibility.Moments from Pittsfield State Forest, Onota Lake, downtown dining and short drive to Tanglewood. This is Berkshire living at its best!

Tucked away in a peaceful, private setting, this charming mid-century ranch offers easy one -level living , warm and inviting. Featuring 3 bedrooms and 2 full baths, the home combines classic character with fresh updates. New oak floors throughout, fresh interior and exterior paint create a clean, move-in ready feel. Relax by the fire or enjoy time on the screened porch or deck. Minutes to town, Taft Farm, Guido's, Skiing and other notable Berkshire attractions.

Thoughtfully crafted custom home offering timeless New England character, quality craftmanship, and beautiful eastern mountain views. Rich natural woodwork and exposed beams create a warm, inviting atmosphere throughout. The custom kitchen with granite, marble and butcher block countertops opens to the dining area with French doors leading to a screened in sunroom. Enjoy the expansive deck, stone patio with firepit, and beautifully landscaped grounds. Spacious living and family rooms with woodburning fireplace and generous mudroom/office. Offering three bedrooms, three baths, plus a versatile creative space, studio/sitting room, endless possibilities. Minutes to downtown Lee, Stockbridge, Lenox, Tanglewood, shopping, dining and all that the Berkshires has to offer for year-round living.

To Be Built Home - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 3.59-acre lot (MLS # 248344), installed private well, perc test/soil evaluation complete, and underground electric in place. Lots may be purchased separately. HOA maintains driveway and common land. Covenants require a minimum 2,000 sq. ft. home with two-car garage. Taxes shown are for land only.

Wake up to breathtaking panoramic waterfront views & end every day with spectacular sunsets from this exceptional ranch offering approx. 170' of waterfront frontage.This well-maintained home features 3 bedrooms, 2 full baths & an inviting open layout designed to showcase the stunning scenery.The sunroom, with walls of glass sliders, opens to an expansive deck-perfect for entertaining, relaxing or simply enjoying the peaceful waterfront setting.Inside, a beautiful stone gas fireplace creates a warm focal point, while radiant heat in the upper level & basement floors provides year-round comfort.Additional features include central a/c, new windows throughout & a walkout basement offering easy access to the outdoors & possibility of an ADU. The business zoning provides added flexibility for

Barns, Brook & Beautiful Living Uniquely spanning the Williamstown, MA and Pownal, VT state line, this inviting property combines New England charm with exceptional flexibility. The expanded 3,500 sq ft home offers 4 bedrooms and 2 full baths, including an option for a first-floor bedroom. Warm, connected living spaces include a stone-fireplaced family room, open kitchen and dining area, a cozy tavern room with wet bar, and a shaded patio for summer enjoyment. The 3.4-acre Vermont parcel features Broad Brook along its boundary plus two outstanding outbuildings: a 30'×40' insulated and finished barn with office and 12' ceilings, and a 30'×50' three-bay garage with 12' rafter clearance--ideal for vehicles, equipment, hobbies, or future conversion. With the house on 0.6 acres in MA and the

Stockbridge Investment Opportunity Fully Rented In Town 5-Family Home office available with a bathroom. Short walk to Post Office, Restaurants, Library and the Red Lion Inn. Stockbridge Town Park located across the street and hiking trails at the end of the street. See pictures. Can also be purchased as part of a investment portfolio 35 Main Street West Stockbridge ,Ma MLS# 249539

Well-maintained seven-unit investment property in a convenient Southeast Pittsfield location. This handsome brick building features spacious apartments, classic architectural character and practical layouts. Six units offer two bedrooms and one bathroom, while the additional basement-level apartment includes one bedroom and one bathroom that needs remodeling. Each unit features a fireplace mantel, rear porch with both interior and exterior access, along with a flexible front room that can be opened to the dining room. Additional improvements and amenities include replacement windows, on-site laundry, private off-street parking, individual basement storage areas for each apartment and a rear interior egress staircase serving all units. Heat and hot water are included in the rents.

A rare opportunity to become the next steward of a remarkable piece of Sheffield history. Dating to 1819 and prominently located on South Main Street in Sheffield's Historic District, this extraordinary antique is filled with the character, warmth and craftsmanship of another era. 16 rooms, 5 bedrooms, multiple baths and 4 fireplaces, the home features beautiful wide-board floors, period details, sun-filled rooms and gracious proportions. A large three-season porch and welcoming front deck extend the living spaces and add to the home's timeless village appeal. With its rich history, wonderful scale and multipurpose zoning offering intriguing possibilities, this is a property ready for its next chapter--an opportunity to preserve its past while creating a home for generations to come.

Completely reimagined from top to bottom, 1790's Colonial blends historic New England character with modern luxury in a truly one-of-a-kind Berkshire setting. Located directly across from Pontoosuc Lake, the property offers stunning lake views, exceptional craftmanship and endless possibilities for live/work, business venture or investment in business/residential zone. Stunning kitchen featuring radiant heat, quartz countertops, high end appliances, oversized center island with dramatic full waterfall quartz sides flowing on every exposed edge. First-floor bath/laundry w/radiant heat. All three bathrooms have been fully renovated with spa like appeal and upscale design. Large living room/dining room, 1st floor bedroom with lake views, 2 sunporches all on main leve

Exceptional investment opportunity in the heart of the Berkshires! Mixed use building featuring six residential apartments and one street level commercial storefront in a high visibility Main Street location. Minutes from the Massachusetts Turnpike, this property offers easy access as a gateway to the Berkshires. Diversified income potential from residential and commercial tenants. This property is in a highly desirable location.

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!

Great Barrington A masterful rebuild with reverence for Great Barrington's past and a bold reimagining for modern living. This 5-bedroom, 4-1/2 bath colonial sits in-town and blends historic charm with contemporary luxury for effortless, years-long comfort. Property Highlights 5 Bedrooms | 4 Full Baths + 1 Half Bath** Complex rebuild from the ground up** - preserved nod to the town's heritage with a fresh, modern interior Chef's Kitchen** - high-end appliances, ample prep space, and thoughtful layout for entertaining Radiant Floor Heating** - in entry Dual Fuel Heat throughout High Velocity Central Air Conditioning** - efficient, quiet climate control Solid Heavy Doors with Emtek Hardware** - substantial, timeless feel with premium finishes 4-Season Porch**

Sun Filled Historic Reproduction Home Built in 2004 seamlessly blends old-world charm with contemporary comfort. Set on 1.82 acres with sweeping mountain views, this 3-bedroom, 2.5-bathroom home features meticulous hand-crafted details throughout-honoring traditional design while offering the conveniences of modern construction. The welcoming gourmet eat-in kitchen is perfect for everyday living & entertaining. Step out to the inviting covered porch-an ideal spot to savor morning coffee & evening sunsets with mountain vistas. The primary suite captures stunning views, while the expansive yard provides additional room to roam. 2-car oversized garage. Secluded setting just minutes to downtown Gt Barrington & Berkshire attractions.

A DRILLED WELL, A COMPLETE 6 BEDROOM SEPTIC SYSTEM, A HORSE BARN AND A SHED COMES WITH THIS FABULOUS 42 PLUS ACRE PARCEL. BEAUTIFUL STONE WALLS SURROUND THE BUILDING SITE AND ACROSS FROM PROTECTED LAND

Easy living Ranch home on beautiful Onota Lake. Fantastic views of the Lake and Distant Berkshire Hills. Enjoy westerly sunset views from your expansive, manicured lawn and almost every room in the house. A quiet setting with comparable homes and easy access to all the Berkshires has to offer. Needs a little TLC, but well worth it for this sought after location and lifestyle. Hardwood floors refinished and interior recently painted.

Set on a desirable tree-lined dead-end street in the heart of Lenox, this beautifully restored 1937 Cape blends timeless character with exceptional craftsmanship. Featured in Berkshire Magazine, the 3,740 sq. ft. home offers original heart pine floors, a wood-burning fireplace, and extensive updates including new plumbing, electrical, Pella windows, roof, and central AC. The three-level layout features 3 bedrooms, 4 full baths, two upper-level suites, and a finished lower level with a guest suite, office, and workshop. French doors open to a wraparound veranda overlooking Goshen stone terraces, fruit trees, and a fire pit. Walk to downtown Lenox with convenient sidewalk access, while Tanglewood is just minutes away.