Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra storage. Inside, enjoy abundant natural light in the glassed-in sunroom or relax on the multiple porches and decks. A key feature is the large, private in-law apartment, perfect for multi-generational living or rental income. Ideally located in the heart of Sheffield village, you'll enjoy the comforts of downtown just steps from your doorstep.

Experience the best of log home living on this picturesque 112-acre countryside getaway, ideal for outdoor enthusiasts and nature lovers alike. Surrounded by stunning mountain views, the property features a network of wood roads, seasonal streams, and abundant wildlife creating a peaceful haven. Located just minutes from Berkshire East Resort, offering downhill skiing & mountain biking, or enjoy the scenic Deerfield River, known for excellent fishing and whitewater rafting. With endless opportunities for year-round recreation, this property is a true four-season retreat. Inside, the spacious great room welcomes you with a cathedral ceiling & sliding glass doors that frame breathtaking views. The open kitchen and dining area seamlessly connect to the living space and a generous deck,

Exceptional Multi-Use Property. Spacious commercial space complemented by a fully renovated two-bedroom apt. Strategically positioned in a high-traffic location - minutes to bustling Great Barrington - this 4,892 SF property has outstanding potential. Versatile main floor ideal for various commercial ventures, while the residential units provide excellent live/work opportunities. In addition, the property features a separate 1 BR apt. & 2 oversized detached garages, all of which have generated steady rental income. Recent upgrades (electrical, plumbing, HVAC, septic system, and most windows) ensuring modern efficiency. With a proven history of strong income across all units this property presents a great opportunity to run a business while leveraging rental revenue to support your vision.

Exceptional Multi-Use Property. Spacious commercial space complemented by a fully renovated two-bedroom apt. Strategically positioned in a high-traffic location - minutes to bustling Great Barrington - this 4,892 SF property has outstanding potential. Versatile main floor ideal for various commercial ventures, while the residential units provide excellent live/work opportunities. In addition, the property features a separate 1 BR apt. & 2 oversized detached garages, all of which have generated steady rental income. Recent upgrades (electrical, plumbing, HVAC, septic system, and most windows) ensuring modern efficiency. With a proven history of strong income across all units this property presents a great opportunity to run a business while leveraging rental revenue to support your vision.

Discover a truly exceptional opportunity to own a spacious 3-bedroom seasonal cottage on 1.3 acres of uniquely private land in one of the Berkshires' most desirable lakeside enclaves.Nestled in the serene and exclusive Beachwood community on Stockbridge Bowl, this property offers the perfect balance of natural beauty, privacy, and cultural access. Residents enjoy steps to a private beach, tranquil surroundings, and proximity to the region's finest cultural destinations.The home's inviting open-concept layout features a bright kitchen, dining, and living area centered around a cozy fireplace. Cathedral ceilings, updated appliances, and thoughtful upgrades throughout add modern comfort to this classic retreat

Check out this unique opportunity to own a historical gem in the heart of Colebrook. This beautiful antique Colonial sits on five fairly level acres which encompasses a pond, many fruit trees and berry bushes. Perfect for a growing family or someone looking for a country retreat with Norman Rockwell views. The ''Cooper House'' is a historical icon in this town; a perfectly located corner lot that is equal distance to Great Barrington, MA and Torrington, CT, and only minutes to Winsted and Norfolk, CT. Close to skiing, shopping, restaurants, town Community center, post office, town pond and newly renovated Colebrook Store. This charming town has a close community feel. Don't miss your chance to own a piece of history. Make sure to set up your showing today!

This one owner home has been a family treasure since 1981 and now it can be yours. Sited on nearly one level acre and abutting farmland the location is ideal. An inviting sunroom addition beckons you to relax. A family room with gas fireplace is open to the oak cabinet kitchen. Hardwood floors, 2 car attached garage, four bedrooms and 2.5 baths within. Brand new heating/cooling systems in 2025, central vac too! Plan a private viewing now.

This approximately 155-acre Berkshire nature preserve has enough frontage on Johnnycake Hill Road to accommodate four building lots. Nestled in the beautiful corner of the world where the Pioneer Valley meets the Berkshire Hills, the property is ideal for a myriad of outdoor uses including horseback riding and cross-country skiing. The land contains well over a mile of logging trails and old roads, past old house and school foundations, wells, and stone walls enclosing abandoned sheep pastures. The property is up the hill from the Chester Theatre, and within easy reach of many cultural venues including Jacob's Pillow, the Mahaiwe, Tanglewood, Mass MoCA, and the vibrant four college community. This peaceful hardwood forest offers a natural wildlife habitat,and significant timber value

WONDERFUL CONTEMPORARY HOME '' ON THE HILL'' IN GB. CONSIDERED ONE OF GB'S MOST DESIRED AREAS. ENJOY THE CONVENIENCE OF BEING CENTRALLY LOCATED TO SHOPPING, RESTAURANTS, AND ENTERTAINMENT ARE JUST WALKING DISTANCE TO ONE OF NEW ENGLAND'S BEST DOWNTOWN AREAS.THIS OPEN CONCEPTED HOME OFFERS GREAT NATURAL LIGHT AND THE ABILITY AND OPPORTUNITY TO COMMUNE AND ENTERTAIN.THREE BEDROOMS- MAIN BEDROOM OFFERS EN SUITE FULL BATHROOM. ADJACENT IS A GOOD-SIZED BEDROOM WITH CLOSET AND SKYLIGHT. ACROSS THE HALL IS A FULL BATHROOM WITH LAUNDRY FACILITIES. THE THIRD BEDROOM IS HUGE WITH LOFT AREA WHICH COULD EASILY DOUBLE AS A DEN, STUDY, TV ROOM OR MEDITATION AREA.

In the heart of the Berkshires, this exceptional 50+ acre parcel presents a rare opportunity steeped in natural beauty and historical significance. With three approved building lots already in place, the property offers incredible potential--for development, investment, or the creation of a private multi-residence retreat. Bordering the picturesque Stevens Glen and abutting conserved lands, the site provides unmatched serenity and long-term preservation of its surroundings. Several elevated locations offer ideal opportunities with sweeping views across the valley.Perfectly situated for both privacy and convenience, this remarkable lot is just minutes to Tanglewood, downtown Lenox, Stockbridge, and the region's world-renowned cultural and recreational attractions. A legacy property!

Beautiful two bedroom, two bath condo perfectly situated in the center of Lenox, Massachusetts-the cultural heart of the Berkshires. Enjoy high Ceilings, beautiful wood floors, large windows, and abundant natural light throughout. The spacious layout features a gas fireplace, granite countertops, and a gas stove in the modern kitchen. The inviting living room opens to a private balcony, perfect for relaxing outdoors. the primary suite includes an ensuite bath. Additional highlights include in unit washer and dryer, on-demand hot water, natural gas heat, and a large storage unit, your own parking space behind the building and access to a beautiful Exercise room for all condo owners. A rare combination of comfort, style, and convenience in one of the Berkshires most desirable towns.

Significant Price Adjustment: Rare opportunity to locate your business in a prime downtown location close to North St., banking, grocery store, pharmacy and residential neighborhoods. At 5,496 sq.ft. this property offers a combination retail and warehouse with high ceilings and lots of natural light from the large windows located on the front of the building. Prominent signage options with high volume traffic counts. Off street parking lot provides plenty of options for customers and employees. Rear industrial door provides access with an interior caged pen for security. Owner financing can be considered. Zoned within the Downtown Creative District-see documents for more detail.

Nestled on a peaceful street, this inviting 3 bedroom, 1.5 bath home offers the perfect blend of comfort and convenience. Step inside to find a bright and welcoming living space filled with natural light, a cozy dining area, and a functional kitchen ready for your personal touch. The three bedrooms provide plenty of room for family, guests, or a home office, while the updated half bath adds extra convenience.Enjoy morning coffee on the front porch or unwind in the private backyard--ideal for relaxing or entertaining. With sidewalks leading straight to town, you'll love being just a short stroll from shops and restaurants, all while enjoying the tranquility of a quiet neighborhood setting.Move-in ready and full of charm, this home offers small-town living at its best.

Set within the region's most celebrated mill conversion, Loft 207 at Greylock WORKS is a beautifully scaled 1BR | 1.5BA + Study Berkshires residence offering 1,250 SF of luminous, corner-exposure living. With 12.5-foot ceilings, expansive proportions, and oversized windows drawing natural light from two sides, this refined home blends industrial authenticity with contemporary design, creating a generous and distinctly modern loft environment.The open kitchen and the generous living and dining area showcase the architectural character of the original mill: gorgeously restored hardwood floors, hand-burnished structural elements, and regionally sourced schist countertops selected by the project's architects to elevate the building's historic textures.

Discover the timeless allure of 'The Turning Point,' a quintessential Berkshire retreat nestled in the hills of Great Barrington. Originally a 1800's stagecoach stop, this enchanting 3600-square-foot property boasts a rich history as a thriving inn, short-term rental and home, offering 7 bedrooms and 6.5 bathrooms. Immerse yourself in its New England charm, complete with a wood stove, propane fireplace, wide plank floors, large kitchen, first floor bedroom, office and a welcoming floorplan emanating warmth and comfort. Perfectly situated mere moments from Butternut Basin (one of the Berkshires top ski destinations) and a short drive from vibrant downtown Great Barrington, this charming sanctuary invites you to experience the best of Berkshire living.

Discover the timeless allure of 'The Turning Point,' a quintessential Berkshire retreat nestled in the hills of Great Barrington. Originally a 1800's stagecoach stop, this enchanting 3600-square-foot property boasts a rich history as a thriving inn, short-term rental and home, offering 7 bedrooms and 6.5 bathrooms. Immerse yourself in its New England charm, complete with a wood stove, propane fireplace, wide plank floors, large kitchen, first floor bedroom, office and a welcoming floorplan emanating warmth and comfort. Perfectly situated mere moments from Butternut Basin (one of the Berkshires top ski destinations) and a short drive from vibrant downtown Great Barrington, this charming sanctuary invites you to experience the best of Berkshire living.

The Amasa Spencer House, circa 1791, is a beautifully preserved gem for antique-home lovers. Tucked into a bucolic yet convenient setting in West Stockbridge, it offers the rare ability to stroll to shops, restaurants, hardware store, market, arts and entertainment, coffee shop and a bookstore in the charming village center. Thoughtfully detailed from top to bottom in vibrant Farrow & Ball colors, the home features newly updated kitchen appliances including an induction stove, paired with custom cabinetry all while retaining much of its original charm. A first-floor bedroom and full bath with laundry provide effortless one-level living. Original flooring, three fireplaces, and a screened porch with mountain view add warmth and character.

Step into this beautifully updated 3-bedroom, 3-bathroom retreat nestled in one of Jiminy's most family-friendly neighborhoods. 2 bedrooms and 2 Full baths on the 1st floor. The open-concept living area features floor-to-ceiling windows that flood the space with natural light, highlighting the elegant hardwood flooring and cozy fireplace. The gourmet kitchen boasts quartz countertops and top-of-the-line stainless steel appliances, perfect for entertaining. The primary suite offers a spa-inspired bathroom with a walk-in shower. Outside, the meticulously landscaped, fenced-in patio provides a private sanctuary, complete with plenty of room for al fresco dining. Enjoy the convenience of being just a short walk from the slopes and local shops. This captivating property won't last long.

Great Opportunity for business/building ownership. Turnkey Bar, Restaurant, & Venue in the Heart of Adams, MA in the Beautiful Berkshires. Iconic Adams Ale House- Massive Bar and Event Space for Sale. Adams Landmark Ale House- a Favorite for Locals and Tourists. Rare mixed use commercial gem-Bar, Kitchen, Auditorium/ballroom. Ready to Reopen.Near MassMoca, Mass College of Liberal Arts, Williams College, Clark Art Museum, Jiminy Peak Ski Area, Historic Mt. Greylock Site. Professional Theaters in Adams, Williamstown and Pittsfield.

Contemporary home nestled on over 7 acres minutes to Great Barrington center. The entry level of this home has a large boot room with a nice size laundry room off of it. The stairs lead you up into the main living space with an open plan kitchen, dining and living. The outside very much becomes part of the living space during the warmer months with doors to a front porch and a side open deck. Down the hall there are two guest rooms and a hall bath. Upstairs off a small landing there are two generous guest rooms with vaulted ceilings and a hall full bath. New heating system, new windows in most of the house,