Large scale 4 Unit commercial property offers four excellent rental opportunities in the heart of downtown's Park Street. The building features two gleaming residential apartments that capture the vibrant city lifestyle, perfect for residents seeking urban convenience. The retail space is expansive and currently vacant on the right side, providing a blank slate for your business or investment plans, while the left side is already leased, generating immediate income. Ideal for investors or entrepreneurs looking to capitalize on prime downtown location and diverse income streams. Current monthly income $4.450.

Welcome home to this peaceful & serene 3 bed, 2.5 bath contemporary offering an open floor plan, main-level primary suite, & a private trail leading to the wild streambed of Glendale Brook! The main level features a spacious living rm & dining area w/ propane stove & sliders to a sunny deck, a kitchen w/ pantry closet, half bath w/ laundry, a first-floor office, & a primary bedroom w/ ensuite bath featuring a jetted tub & shower. The lower level provides flexible living w/ a 2nd office, bonus room, 2 beds w/ forest-facing windows, a shared recreation area, kitchenette, full bath & a built-in sauna! An exterior door opens to private trail along Glendale Brook, leading to a natural dipping pool. Additional features include 2 separate meditation rooms w/ own entrances, & a newly replaced furn

Set on 16 private acres, this four-bedroom, one-and-a-half-bath home has been lovingly updated while preserving its rustic warmth and character. Soulful wood floors, cozy living spaces, and a versatile attic retreat give this home an authenticity you simply cannot manufacture. A two-story wood stove heated barn bursting with natural light makes for an ideal studio or creative workspace. Step outside to a spring-fed pond reaching ten feet at its deepest and perfect for a summer float, a morning swim, or simply watching the light dance across the water. A gazebo offers a quiet perch to read, sketch, or simply breathe it all in. And when the day calls for deeper restoration, a private sauna awaits. Close to Jacob's Pillow, Becket Arts Center, Lee, and Tanglewood. A true sanctuary.

A peaceful, private retreat bordering protected land with no homes in sight. Enjoy a sparkling swimming pool, a dramatic 20' cathedral-ceiling great room, and seamless access to a deck overlooking the grounds and pool. Total quiet, total privacy, and minutes to the Berkshires for culture, dining, and farm-to-table markets. Includes coveted Queechy Lake rights. Principal en-suite and 3 other generously sized bedrooms - 3 baths - 8 person SAUNA -- must see Owner-occupied. Please allow 24-48 hours' notice.

Big, 2800 square foot log home privately set on a seven plus acres. The great room, framed with massive log timbers, opens onto the large deck leading to the hot tub and fire pit. Kitchen features include granite & butcher block counters and an eat in island. Two bedrooms - each with private half baths - plus a full bath in the hallway complete the main level. The upper level loft is used as an office and extra sleeping area. The primary bedroom, cathedral ceiling, walk in closet, has an ensuite bath with soaking tub and separate shower. The game room on the lower level can also be used as an overflow sleeping area with the full bath including a jet tub and sauna. Laundry area, mud room, garage access & utility room Are located n this level. The 7+ acre lot includes a surveyed 2nd lot.

Welcome to 365 Deer Run, a beautifully refreshed four bedroom, 3.5-bathroom home tucked into the sought-after Otis Woodlands community. Inside, 2,297 square feet of cedar-wrapped warmth unfolds beneath cathedral ceilings and skylights, with east-facing windows that bring beautiful morning light into the home throughout the year. A window-lined three-season porch extends the living space and offers an inviting place to linger through spring, summer, and fall. The home is designed for both comfort and ease, with features including soapstone countertops, gas heat with Nest controls, a private sauna, and a brand-new roof. Thoughtfully updated and move-in ready, it offers the rare combination of character, modern comfort, and minimal fuss.

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.

Escape to your own private retreat in Williamstown, 'The Village Beautiful.' This spacious 5-bedroom, 4.5-bath home sits on 7.5 private acres and offers over 4,000 sq. ft. of living space throughout three levels, plus a finished basement with full bath and sauna. This home blends classic and modern features: exposed wood beam ceilings and a new, private primary suite with soaking tub. The home features a second primary suite, a third floor bedroom or loft space, and an abundance of natural light throughout. There are two woodstoves and a wood-burning fireplace for staying warm, and mini-splits for cooling in the summer. The expansive property boasts a designated garden area, a large garage with loft space above, and two large decks for entertaining and enjoying the surrounding nature.

Special Berkshire retreat on 25 private acres in Harrington Woods with beautiful views. Offering 5,400 sq ft, this 4-bedroom, 4-bath home features oversized rooms and high ceilings. The main level includes a recently renovated chef's kitchen, expansive primary suite with walk-in closets, guest room/office, library with built-ins, dramatic living room and a 400 sq ft screened porch. The walkout lower level offers two additional bedrooms, exercise room, family room, professional pool table, sauna and steam shower. Additional highlights include an oversized 2-car garage with Level 2 EV charger, 12x24 storage shed, and a 30-panel solar array with a transferable utility credit. HOA amenities include tennis, pickleball and a heated seasonal pool. Minutes to Otis Ridge and Great Barrington.

Set on 22 private acres, this Monterey retreat offers a peaceful escape from city and suburban life. Freshly painted this spring, it's near Lake Garfield and Monterey Town Beach, and across from Beartown State Forest. The bright, expansive home features four ensuite bedrooms, including a spacious primary suite, large entertaining areas, and cathedral & vaulted ceilings. Outdoors, enjoy a 16' x 40' heated gunite pool, an outdoor enclosed shower, a large stone patio, and the year-round Loom Brook flowing through the woods. The lower level includes a sauna, exercise pool, and utilities. A two-car garage connects to a mudroom with laundry, half bath, and outdoor shower, plus a large bonus room above. A rare opportunity at this price in scenic, convenient Monterey, with fiber internet.

Set on approximately 62 acres spanning both sides of Cone Road, Middle Branch Overlook Estate offers sweeping southeast views across the Middle Branch of the Westfield River valley. The 3-bedroom timber-frame home features warm pine interiors, open living spaces, a first-floor primary suite, lower-level recreation room, and two additional flex rooms, plus another room above the garage for office, studio, or expansion potential. Amenities include a heated pool, gazebo, gas fire pit, 3 garages, workshop, generator, and 56 solar panels on the house and garage. Open fields, woodland, brook, ponds, trails, and substantial road frontage may offer potential for additional lots, subject to approvals and buyer due diligence. Majority in Chapter 61B.

Enjoy the relaxing Berkshire lifestyle on a friendly cul-de-sac within walking distance of town and Lake Mansfield. As the first house built on the street, the property has matured beautifully -- seasonal flowering trees and pollinator-friendly gardens bring color and life to the yard from spring through fall. Cedar columns frame a distinctive front door that opens into 3,800 square feet of tastefully designed living space, where soaring ceilings, a linear gas fireplace, and built-in bookcases set the tone. The living room flows out to a screened-in porch with a treehouse-like view of the wooded backyard -- the perfect spot for morning coffee or summer evenings. The chef's kitchen is beautifully appointed with Wolf and Sub-Zero appliances and granite countertops, and opens to the dining

Just beyond New Marlborough Village this architectural gem showcases 5,653 square feet of superior craftsmanship along the Umpachene River. Built in 1989, this 5-bedroom home was designed by internationally renowned architect Paul Bierman-Lytle, a pioneer in sustainable development and healthy home design known for championing non-toxic climate adaptive building materials. Distinctive circular towers, curved walls, arched windows and premium natural finishes harmonize with the surrounding natural landscape. The grand foyer opens to an expansive kitchen, living, & dining space anchored by a striking Finnish soapstone wood stove and marble fireplace. A sun-filled breakfast room leads to a greenhouse atrium and an impressive indoor pool pavilion, fully heated for year-round enjoyment.

Originally built in the 1700s, this historic post-and-beam barn has been thoughtfully renovated over time while maintaining its unique character and charm. A recently installed solar energy system allows for highly efficient living with the potential for an off-grid lifestyle. The home features an open floor plan filled with natural light from numerous oversized windows. A chef's kitchen adjoins the dining area, creating an ideal space for entertaining. With three full floors of living space, the home offers four ensuite bedrooms plus an additional bedroom, providing comfort and privacy for family and guests. Enjoy seamless indoor-outdoor living with a screened porch off the main level leading to spacious decks and a hot tub. The lower level includes a media room and sauna for relaxation

Welcome to Treetops. A long private driveway passing a large pond sets the scene for this impressive hilltop retreat with 6,000 square feet across three levels and seasonal views of the Taconic Hills. Built with wood hewn from trees on the property, including the distinctive stairway, the home offers a huge open-plan main level ideal for gatherings, along with an indoor pool, hot tub, sauna and a dramatic two-story primary suite. Five bedrooms and five baths provide ample space for guests, with additional bedrooms on the upper and lower levels plus a family room downstairs. A second home may be built on a conserved, included, second parcel. Expansive decks, a three-car garage, sold fully furnished, and abutting the Appalachian Trail conservation lands complete the offering.

OFFERED FULLY FURNISHED AND TURNKEY. Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape architect. For guests, they can choose between the three-bedroom, two-bath Cottage or the one-bedroom Cabin, both of which are intimate and offer plenty of privacy for family and friends. Whether it's poolside by day, trails in the afternoon, or hanging by the fire pit at night, there is something for everyone at this mid-century getaway set in the Berkshire hills and only minutes to Litchfield County

April Hill, an exquisite 1850 Greek Revival masterpiece. This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate showcases classic stone walls, a serene spring-fed pond and a heated saltwater pool. The impeccably maintained lawns and expertly designed grounds establish a pristine country retreat. Premium upgrades include superior rock wool insulation throughout. Perfectly positioned just minutes from Tanglewood's celebrated performances, fine dining and thriving cultural attractions in the Berkshires.

STILL HOUSE brings next-level contemporary design and a new kind of elegance to the Berkshires--quietly luxurious, exquisitely detailed, and made to be lived in. Minutes from the center of Great Barrington, this newly completed home of more than 5,000 square feet pairs the distinctive vision of acclaimed Brooklyn studio Me & General Design with superb craftsmanship and exceptional materials throughout. Four bedrooms, five-and-a-half baths, a heated saltwater pool, bespoke spa and fitness spaces, solar energy and exceptional privacy make this as much a retreat as a home. Preserved stone walls from the original structure bring history, texture and character to the new architecture--and keep something distinctly Berkshire at its heart.