Some Berkshire homes are simply places to live. Others become part of the way you want to live. The Oronoque Villas are among those rare places. Built in the mid-1990s on the historic grounds of Oronoque--one of Stockbridge's great Berkshire cottages--just eight freestanding villas were thoughtfully sited within the estate landscape, complementing the original mansion, now home to distinctive condominium residences. Surrounded by mature trees, sweeping lawns, and established gardens, this villa offers the warmth and privacy of a house, the simplicity of one-level living, and the freedom to lock the door and leave whenever adventure calls. Whether as a year-round home or a favorite Berkshire retreat, life here has a wonderful way of slowing you down.

Welcome to life on beautiful Pontoosuc Lake, where breathtaking sunrise views and year-round waterfront living await. This charming, move-in-ready home offers the perfect combination of comfort, thoughtful updates, and low-maintenance living in a truly special lakefront setting. The open and airy living room features soaring vaulted ceilings, expansive windows that capture stunning lake views, abundant natural light, and a cozy gas fireplace, creating a warm and inviting space to relax or entertain. The well-designed floor plan includes spacious first-floor bedrooms with generous walk-in closets, updated bathrooms, newer flooring, Anderson windows, skylights, and multiple heating zones for added comfort.

Modern elegance meets turnkey peace of mind in this fully reimagined Sheffield retreat. Set on 2.3 level acres, this 3BR, 3.5BA sanctuary spans 2,748 square feet across three finished levels. The sun-drenched main floor features wide-plank white oak floors, a gas fireplace, a large half bath, a chef's kitchen with stainless appliances, white quartz counters, and seamless access to a wrap-around deck. Upstairs, a treehouse-like loft adds charm, while the primary suite delivers a spa-like experience. The three suites were designed for intimacy and privacy. The walk-out lower level houses a guest suite and fantastic game room. Renovated top-to-bottom with no expense spared, central A/C, and new mechanicals--just bring your suitcase. 15 mins to Guido's and 45 mins to the Wassaic NYC train.

First-time for this treasured dwelling to be available for purchase. This magical setting surrounded by lush gardens and plantings is just the beginning of the enchantment. Distant mountain views to the east brings your viewscape to Butternut Ski & beyond. Inside the dwelling is a large open living space & kitchen on the first floor. Separately, there is a first-floor Ensuite. Abutting the first level, is a charming screened porch for dining or just taking in the sounds of nature. An open deck on the backside of the main level awaits your enjoyment. The 2nd level contains two VERY large bedrooms Ensuite; both with walk-in closets along with more locations for maximizing the distant views. The finished lower/walkout level has a full bath for a possible 4th Ensuite and living space

Welcome home to an extraordinary blend of modern style, flexible living, and resort-quality outdoor amenities, perfectly located moments from the heart of downtown Lenox, top-notch dining, Tanglewood, & the local high school on a quiet cul-de-sac. Step inside to a bright, freshly painted open floor plan framed by updated windows that flood the space with natural light. The inviting living area features a cozy gas fireplace, creating a warm focal point for chilly evenings, while the kitchen comes equipped with sleek, modern appliances. This turnkey residence offers 3 spacious bedrooms plus a versatile 4th full-size room that's ideal for a fourth bedroom, dedicated home office, or quiet retreat along with 2.5 updated bathrooms.

Originally built in the 19th century, this Egremont schoolhouse has undergone a radical,''down-to-the-studs'' transformation, and has been thoughtfully designed to create a high-performance home for modern living, while honoring its historic character. Sound structural integrity, with state of the art insulation, custom engineered windows, a new HVAC system, and a solar array for near zero energy overhead make this home immensely comfortable and sustainable for decades to come. The Great Room features dramatic vaulted ceilings anchored by original exposed beams and a new, high-efficiency propane free standing stove. The chef's kitchen has custom cabinetry topped with honed marble counters. The bath features custom tile work and radiant heated floors.

Investment opportunity near downtown Pittsfield. This renovated 7,904-square-foot commercial building is situated on approximately 0.72 acres in the Downtown Creative District and is currently leased to an established daycare/school operator through August 2031. The property generates an annual base rent, plus documented reimbursements for real estate taxes, insurance, and water/sewer expenses. The building offers approximately 3,952 square feet on each of two levels, with an open, adaptable layout suitable for educational, nonprofit, institutional, professional, or community-oriented uses. Improvements include central HVAC, replacement windows, sprinkler and fire-alarm upgrades, and extensive interior renovations. An elevator provides convenient access between floors.

Discover a rare opportunity to own 181 extraordinary acres in the picturesque town of Adams. Available for the first time, this expansive property features an ideal blend of open meadows, rolling hills, mature woodlands and stunning views - perfect for nature lovers, outdoor enthusiasts, or visionary developers. The land boasts gently sloping topography from east to west, creating a dynamic landscape rich in wildlife and diverse ecosystems. Property borders Savoy Mountain State Forest to the east, providing direct access to hundreds of acres of protected land. Extensive frontage on East Hoosac Street and additional right-of-way access from East Road opens the door to potential development. Priced at just under $5,000 per acre, this is a unique opportunity in the heart of the Berkshires.

On 5 park-like acres this well maintained and thoughtfully designed home overlooks a tranquil pond and offers a serene getaway. Designed by architect Dennis Wedlick to maximize space and ease of living the home features 3-4 bedrooms and 3 full baths of which one is a separate guest suite. A renovated kitchen and updated bathrooms blend seamlessly with gleaming wood floors. A striking double sided fireplace connects the living room and den. Custom designed windows bring in sunlight while framing picturesque views. An exceptional property, ideal as a full time residence or a country retreat for those looking for both design and a quiet setting. Solar panels have been aesthetically placed to reduce energy bills, EV charger in garage. Full house generator too.

Striking and sophisticated riverfront condominium in superb location, with close proximity to restaurants, shops and theater on Spring and Water Streets, the Taconic Golf Club, Williams College, and the Clark Art Institute. One of only 6 recently built town house units on the river in the handsome Cable Mills complex, number 8 has benefitted beautifully from the discerning taste and style of its owner, with elegant yet understated lighting fixtures, and enchanting touches of color and texture throughout. Light-filled with an abundance of large windows, it offers as well two terraces and two upper decks providing opportunities for al fresco dining and fresh air relaxation. A sleek suite of Thermador appliances graces the kitchen/dining area which includes both a breakfast nook with

Welcome to 3 Cone Hill in the heart of the Berkshires. This rustic retreat is the epitome of a classic country compound that's been lovingly cared for and enjoyed by the same family for many years. Minutes to Tanglewood, this 2+ acre lot hold more fun and relaxation than most large estates. Sitting over Cone Brook, you'll enjoy listening to the babbling water from your screened-in gazebo. After playing a game of tennis or pickle ball, take a soak in the hot tub before guests come, which will be plenty as you can easily sleep 14 people. The house has 5 BR/3BA with an open concept on the main level. The detached garage has 1 BR/1 BA guests quarters where they can come and go as they please. Let the lasting memories begin today!

Steeped in history and rich with character, this remarkable 1767 residence is the oldest home still standing on its original site in Williamstown.Thoughtfully expanded over time, it preserves its historic integrity while offering comfort for modern living.Set on nearly five meticulously maintained acres in one of the town's most desirable neighborhoods, the property feels both private and timeless, with mature plantings, perennial gardens, and sweeping lawns.The classic Cape Cod-style architecture features a wood shake roof, enhancing its New England charm. Inside are 5 bedrooms and 3.5 baths, blending intimate period rooms with light-filled living spaces. A dramatic living room with cathedral ceilings and French doors opens to beautiful Goshen stone patios, ideal for outdoor entertaining.

Set on nearly 3 private acres in sought-after ALFORD, this 4-bedroom home offers privacy, comfort, and Berkshire charm. Built by Howard Chezar, the home was thoughtfully designed with passive-solar principles, allowing the winter sun to naturally warm the interior while minimizing summer sun to help keep the home cool. The open-concept living area showcases beautiful wood details and a warm, welcoming atmosphere. A finished third-floor bonus space offers flexibility for a home office, studio, guest area, or playroom. Relax or entertain on the spacious deck overlooking the in-ground pool and peaceful surroundings. Add'l highlights include an 8-year-young roof, low Alford taxes, and exceptional location minutes from Great Barrington, hiking, skiing, dining, and the Berkshire attractions!

Offered for the first time in more than forty years, this c.1880 residence presents a rare opportunity to own a substantial property on coveted Prospect Hill Road, one of Stockbridge's most desirable addresses. Set privately on 3.5 acres just moments from the center of Stockbridge, the property offers the increasingly rare combination of privacy, acreage, and location that defines some of the most sought-after luxury real estate in the Berkshires and Berkshire County.

Striking and sophisticated riverfront condominium in superb location, with close proximity to restaurants, shops and theater on Spring and Water Streets, the Taconic Golf Club, Williams College, and the Clark Art Institute. One of only 6 recently built town house units on the river in the handsome Cable Mills complex, number 8 has benefitted beautifully from the discerning taste and style of its owner, with elegant yet understated lighting fixtures, and enchanting touches of color and texture throughout. Light-filled with an abundance of large windows, it offers as well two terraces and two upper decks providing opportunities for al fresco dining and fresh air relaxation. A sleek suite of Thermador appliances graces the kitchen/dining area which includes both a breakfast nook with

Discover a rare Berkshire property offering endless possibilities in one of New England's most sought-after destinations. Whether you're seeking a luxurious year-round residence, a four-season getaway, or a property designed for multigenerational living, this exceptional offering delivers the perfect blend of privacy, flexibility, and convenience. Ideally located in the heart of everything the Berkshires has to offer, you'll be just minutes from world-renowned attractions, including MASS MoCA, The Clark Art Museum, and the Williamstown Theatre Festival. Head south to enjoy concerts at Tanglewood, the renowned summer home of the Boston Symphony Orchestra, or take advantage of the area's abundant hiking, biking, and scenic trails. Autumn brings spectacular fall foliage and

12.84 Acres of Prime development Land. Ideal for possible Commercial and/or Residential projects. Close to Shopping and Transportation. Curb cut and some engineering done.

LAND. 12.84 Acres of Prime Development Land. Abuts several Commercial Properties. High Traffic. Centrally located. Lot not cleared. Some engineering done.

Set within one of the Berkshires most coveted communities, 9 Eastbrook Lane is a masterclass in refined living, where thoughtful design meets impeccable care. Beautifully and intentionally sited, this distinguished residence offers 5 bedrooms, 3 full and 2 half baths across a gracious, light-filled layout designed for both elegant entertaining and everyday comfort. The stunning kitchen showcases rich maple cabinetry, a premium Viking range, dual refrigerators and exceptional workspace, perfectly suited for the discerning cook. The renovated primary bathroom evokes a true spa experience, blending luxury and serenity with timeless finishes. Every detail has been meticulously maintained, from the seamless indoor-outdoor flow to the expansive Trex decking ideal for al fresco gatherings.

Beautifully designed for one level living and both pristine and charming...open floor plan with a cathedral ceiling in the great room (which is complete with gas fireplace, built ins and access to the patio); gorgeous kitchen with quartz counters and eating bar, formal dining room, hardwood floors in main living spaces, Primary Suite plus 2 additional bedrooms (one currently used as a solarium with access to the south facing deck) and an additional full bath. Powder room, mudroom and hook ups for laundry. The basement level is fully usable for a game room and other creative uses (wait til you see it!). Gorgeous gardens surround this property and the stone sitting porch and patio are highlighted by gardens and a privacy fence...absolutely charming! For ease of 1 level...this is it!