Discover the charm of yesteryear with this enchanting 6-bedroom, 2-bathroom antique home nestled in the vibrant town of Lee. Accompanied by a large two-story stone barn, this residence offers a blend of historical elegance and modern potential. Original features such as wood floors, Dutch door, and classic stairway railing are complemented by a dining room with beamed ceilings, built-in china cabinets, and bay window with marble seat. Stained glass windows and pocket doors add to the home's unique character, while a marble fireplace graces the front parlor. The sizeable retro kitchen, complete with Geneva cabinets, awaits your personal touch. Set on a corner lot with mature plantings, the property boasts a beautiful backyard--

Settle into the quiet charm of the Windemere Lake community with this 8.592-acre building lot. Tucked away on a peaceful road and embraced by natural woodland, the property offers a sense of seclusion while remaining part of a thoughtfully maintained private enclave. Though it doesn't sit directly on the water, owners enjoy shared access to Windemere Lake--a pristine, non-motorized lake perfect for kayaking, swimming, and unwinding in nature. Build your dream home in a setting where sunsets glow through the trees and the pace of life slows to match the stillness of the lake.

Settle into the quiet charm of the Windemere Lake community with this 7.166-acre building lot. Tucked away on a peaceful road and embraced by natural woodland, the property offers a sense of seclusion while remaining part of a thoughtfully maintained private enclave. Though it doesn't sit directly on the water, owners enjoy shared access to Windemere Lake--a pristine, non-motorized lake perfect for kayaking, swimming, and unwinding in nature. Build your dream home in a setting where sunsets glow through the trees and the pace of life slows to match the stillness of the lake.

Multi-family in a convenient location, walking distance to town and shopping, bus line nearby.Well maintained. The perfect location, walking distance to restaurants and shopping, public transportation nearby.

OPEN HOUSE Sat 11/01/25 11am-12:30pm. This stunning 5-bedroom, 3-bath farmhouse was fully renovated from top to bottom in 2020, offering 2,800 SqFt of stylish, move-in-ready living space in one of Southeast Pittsfield's most desirable neighborhoods. Situated on a generous corner lot, the home makes a striking first impression with its inviting wraparound front porch. A circular driveway provides ample parking and is complimented by a detached one-car garage. Step through the front door into a spacious foyer with sleek hardwood floors throughout the open concept main level. The dining room has enough space for memorable meals and entertaining, while the chef's kitchen is outfitted with stainless steel appliances, a natural gas range, quartz & granite countertops, center island and French

Tucked away in the desirable, low-tax community of Richmond, Massachusetts, this 3-bedroom, 2-bathroom ranch, surrounded by higher-priced properties, offers comfortable single-floor living. The open-concept living area, filled with natural light, includes a recently updated kitchen and features quartz countertops, quality stainless appliances, and ample counter space. The master suite includes a newly updated bathroom. Two additional spacious bedrooms offer flexibility for guests or a home office. A privately owned solar array provides net-zero energy, combining eco-conscious living with cost savings. Located just 4 miles from Tanglewood, the Berkshires' premier cultural attraction, 5 miles from Lenox, the region's culinary hub, 4 miles from West Stockbridge, and 5 miles from Balderdash C

Step into a world where historic charm meets contemporary living in this unique 4-bedroom, 4-bath Arts & Crafts home located in the heart of Southeast Pittsfield. This one-of-a-kind residence is brimming with character and has been lovingly maintained to showcase its original features while providing all the comforts of Berkshire living. This majestic home has a fascinating origin story. Built in the late 1800s, it was once the east wing of the summer residence of the Pillsbury family. Originally adjoined with the house behind it on Wendell Avenue and situated a half block away, the sprawling grand estate was divided into two separate homes, and carefully moved by horse in the early 1900s, establishing the neighborhood that would grow around them.

Located in the Historic District of the picturesque town of Heath, this former Artist loft has been thoughtfully maintained and expanded over the years. Large, expansive spaces greet you as you walk into the 3304 sqft. home with three bedrooms and three bathrooms. There is a separate sizeable bright kitchen wing with a great view of the large private yard, or you can enjoy the yard on the 2nd-floor deck. The home also has a 2-plus acre meadow with a small barn perfect for a hobby farmer or a horse enthusiast. This unique, comfortable house is set in a very private, peaceful setting, offering a tranquil escape from the hustle and bustle of everyday life.

Welcome to 93 Roselyn Drive, a beautifully maintained, move-in-ready, light-filled mid-century gem with style, function, and effortless upkeep, ideally situated in Pittsfield's desirable west-side neighborhood.This home offers big-sky views and a private 0.75-acre yard - perfect for morning coffee, stargazing, or weekend gatherings on the expansive two-level deck overlooking mature, easy-to-care-for gardens.Inside are sun-filled rooms, a classic stone gas fireplace with remote control, a fabulous bonus room with large windows facing the backyard - ideal for a home office, family room, or yoga studio - plus a newly finished lower level adding more versatility with a full bath, cedar closet, laundry area, and plenty of room for a guest suite, media room, or private gym.

ADAMS! Dynamite Berkshire Land. Bordering Greylock Glen Land into Greylock Mountain State Reservation. 1,000's & 1,000's acres of direct access to preserved forestlands & fresh water brooks, waterfalls & ponds. A nature enthusiast dream getaway. Enjoy it all right from your own 83 acres - hike, bike, hunt & snowmobile directly from your own property. Direct access to a vast network of protected trails including the Appalachian Trail. Simply enjoy the wilderness & use for basic camping or build your own mountain paradise. Enjoy Mt. Greylock Views. Located close to town for all the in-town amenities. Easy access North into North Adams, Williamstown & Southern Vermont and South to Cheshire, Lanesboro, Pittsfield, Lenox & Stockbridge. Only about 40 minutes to I-90 connection.

Welcome to your dream getaway in Otis Woodlands, one of the Berkshires' premiere private communities. This beautiful home offers the perfect blend of rustic elegance and modern comfort, ideal for year-round living or a serene weekend escape.Nestled among the trees, this spacious 4-bedroom, 3-bathroom home features a dramatic great room with vaulted ceilings and exposed beams, complemented by a 2020 custom kitchen with quartz countertops--perfect for entertaining. Enjoy the outdoors from the expansive wraparound screened porch, ideal for relaxing or dining al fresco.The upper level boasts a private primary suite with skylights, a full bath, and an open loft area. The main floor includes a bedroom with an en suite bath, while the lower level offers two additional bedrooms

Experience the charm of country living in this comfortable home, situated in the peaceful town of Charlemont, on Wilder Brook. The property includes a spacious barn, formerly a cabinet workshop, and an additional outbuilding for gardening tools or chickens. Enjoy hosting gatherings in the large kitchen and dining room, or relax in the expansive open living area. Upstairs, you'll find three roomy bedrooms and two bathrooms, providing plenty of space for everyone. Perfect for outdoor enthusiasts, this home is just minutes from mountain biking, ziplining, the mountain coaster, and downhill skiing at Berkshire East, as well as world-class fishing and tubing on the beautiful Deerfield River. Seize this opportunity to make this remarkable property yours!

This updated ranch offers single-level living on a spacious, level yard framed by mature deciduous trees, providing natural privacy in one of Williamstown's most peaceful and desirable neighborhoods. Oak hardwood floors lead you into an inviting open living/dining area, complete with a bay window that frames serene views of the backyard. The renovated cherry kitchen boasts quartz countertops, stainless appliances, and a tile backsplash. The spacious primary suite includes a fireplace and renovated en suite bath, with flexibility for a third bedroom or office. Efficient comfort comes courtesy of leased solar panels, four Daikin mini-splits, and two fireplaces. A sunny deck and patio extend your living outdoors. Just minutes to Williams College...

Settle into the quiet charm of the Windemere Lake community with this 6.607-acre building lot. Tucked away on a peaceful road and embraced by natural woodland, the property offers a sense of seclusion while remaining part of a thoughtfully maintained private enclave. Though it doesn't sit directly on the water, owners enjoy shared access to Windemere Lake--a pristine, non-motorized lake perfect for kayaking, swimming, and unwinding in nature. Build your dream home in a setting where sunsets glow through the trees and the pace of life slows to match the stillness of the lake.

This 10-acre parcel in scenic Richmond, available for the first time in generations, offers a rare chance to build your dream home in the heart of the Berkshires. Surrounded by open farmland and natural beauty, this property provides a peaceful and inspiring setting for a country retreat or a year-round residence. The land features gently rolling meadows filled with wildflowers and native ferns, a private pond, and groves of mature trees. Ideally located minutes from Tanglewood, Lenox, plus cultural & recreational amenities that define the Berkshires--including hiking, biking, skiing, and nearby Richmond Pond. An exceptional canvas for a legacy home in one of the Berkshires' most coveted locations.

Set at the end of a private road, this light-filled 2-bedroom Cape exudes classic New England charm. With its hilltop setting and potential for beautiful views, the home features a sense of peace and seclusion. Stone walls and mature trees frame the property, which directly abuts Questing Reservation, a 438-acre conservation area with a 2.3-mile trail of wooded paths and open meadows. Enjoy hiking and snowshoeing, just around the corner.Inside, the kitchen, dining, and living areas flow together, creating an inviting layout. A fieldstone fireplace anchors the expansive living room, where vaulted ceilings clad in natural pine wood add warmth and character to the space. The first floor also includes a generous bedroom, full bath, and laundry room for convenient one-level living.

Welcome to this spacious 4-bedroom, 2-bathroom home offering 1,865 sq ft. of comfortable living space on a generous 1.42 acre lot in the beautiful town of Cheshire. This property features a bright and inviting layout, well-sized bedrooms, and ample room for everyday living or entertaining. New vinyl siding, gutters & awnings added in the most recent years. Enjoy the privacy and outdoor possibilities that come with an expansive lot & beautiful Trex deck leading to the above ground pool. Perfect for gardening, recreation or simply taking in the peaceful surroundings. A wonderful opportunity to own a versatile home in a serene Berkshire County location. Schedule your showing today!

Experience a peaceful Berkshire fall from this inviting ranch-style home in the quiet hills of Becket. Surrounded by vibrant foliage and towering pines, this single-level retreat offers warmth, comfort, and nature at your doorstep. Enjoy scenic hikes and crisp fall days now, then gear up for winter fun with Otis Ridge, Bousquet Mountain, and Jiminy Peak just a short drive away. With a fully equipped kitchen, open living space, and year-round outdoor adventure nearby, this cozy home is the perfect Berkshires getaway.

Spacious split foyer with addition of a year-round heated Florida room featuring inground, heated, fiberglass pool, hot tub, its own granite kitchen, full bath, & Tiki bar, making it ideal for hosting gatherings; or cover the pool and the entire floor with an already existing truss floor system when not using the pool..has 2 egresses, for a great guest/in-law space that can be closed off to the main home. Enlarged, Primary bedroom includes a full bath, walk-in closet and sliders to sneak out to the pool area. Glass room has gas, ceramic tiled fireplace and the main dining room has a field stone fireplace (for cozy New England days). All 3 bedrooms are very large with closet space. There are many extra storage closets throughout the home, as well as an oversized 2 car garage.

Charm. You'll find it in this 3BR, 2.5BA West Stockbridge home. The charm of a farmhouse fence, lush with white hydrangeas, roses, and day lilies, set along a peaceful street where neighbors jog, push strollers, or walk their dogs. The charm of luminous freshly painted interiors and windows framing views of greenery on all sides--mists atop Lenox Mountain, vivid sunsets, and star-spangled night skies. The charm of a spacious enclosed porch for relaxing and entertaining, a 400sf insulated, 'do-with-it-what-you-will' barn with French doors and patio, perennial gardens, overarching maples. Practical charms, too: new roof, new primary bath, updated systems, 2-car garage, 2 minutes to Six Depot, 10 to Tanglewood, 16 to Guidos. Charm and privacy, with room to dream, create. Make it your own.