Nestled in the heart of West Stockbridge, this stunning 5-bedroom, 5.5-bath Federal/Greek Revival style home at 4 Stockbridge Road combines historic charm with modern luxury. Built in 1825, the residence has been beautifully renovated, maintaining its classic character while offering contemporary amenities. The spacious interior features generous living areas, perfect for family gatherings and entertaining. Outside, you'll find a large barn, a greenhouse and impeccable gardens ideal for gardening enthusiasts or creative projects. This property is not just a home; it's an opportunity to enjoy the tranquil beauty of West Stockbridge, with its vibrant community and picturesque surroundings. Located minutes from many local attractions including Tanglewood and minutes from the highway.

Welcome to a custom-designed architectural haven where clean, modern design meets inviting warmth. Meticulously maintained and lightly lived-in, this spotless, move-in ready retreat offers the ultimate in effortless, single-floor living set against a backdrop of mature perennial gardens, custom walking paths, and complete privacy.Step through the inviting front porch into a bright, open-airy floor plan anchored by soaring ceilings, oversized windows, and rich bamboo floors that seamlessly bring the outdoors in. The heart of the home features a cozy gas fireplace and radiant-heated floors for year-round comfort. The chef's kitchen and main living spaces flow effortlessly onto an expansive wrap-around deck-perfect for alfresco dining while taking in views of the private grounds.

Drive in beneath the trees and the house appears in a pool of sunlight, set well back from a quiet road with gardens, lawn and woods gathered around it. There is an immediate sense of having arrived somewhere apart. Private and peaceful, yet not isolated, this one-owner West Stockbridge home has the easy spirit of a modern farmhouse and a distinctly relaxed way of living--a place to slow down and settle in. An inviting front porch, screened by the surrounding landscape, is private enough to become a place of its own--for morning coffee, reading or the pleasure of doing very little.

Beautifully updated and lovingly maintained Colonial in the heart of Great Barrington. Bright, sunny, and truly move-in ready, this inviting home offers a combination of classic charm and comfortable modern living. The first floor features a welcoming mudroom, updated kitchen, heated sunroom, dining room, living room, family room, laundry, and full bath, providing plenty of space for both everyday living and entertaining. Upstairs are three comfortable bedrooms and a second full bath. Outside, enjoy a lovely yard and charming covered porch--perfect for relaxing and enjoying the neighborhood. Ideally located with easy access to Great Barrington's vibrant town center, library, restaurants, shops, and churches. A warm and beautifully cared-for home in a wonderful convenient location.

Upper Rhoda Pond waterfront in Copake, New York (southern Columbia County) is a very special place. About 2 hours from NYC, it is a private 78 acre body of water with no public access and no gasoline engines. The waterfront includes new docks and kayak to row out to your exclusive floating raft. This 3 BR + office has 3 BA and is approximately 1944 sf with a full basement. The open floorplan lends itself to family, friends and entertaining. Wood burning fireplace to warm up on those chilly summer nights. Fiber optic is on the premises. The screened porch has panels, so that you can take in the country location and water views all year round. There is even a heater out there. The lower level works as a family room. The sale includes a pool table and ping pong table. Storage galore.

Otis Wood Lands lakefront Contemporary with four bedrooms and three full bathrooms. Open kitchen/dining/living area with views of the lake. Spacious, two-level screened-in porch with deck access. First-floor primary suite with private deck access, and two additional bedrooms and full bathroom on the main level. Large lower level with walk-out access and fourth bedroom. Community amenities include pool, tennis/pickleball courts, lodge, playground, beach and community lake for non-motorized boats. Reserve fund fee of $4,000 due from buyer at closing. Woodstove disconnected prior to closing.

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.

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

The original farmhouse at the bend in the road: a center chimney colonial of 1782, dearly loved and held in wonderful condition. The grounds are a work of art cultivated over many years, a garden you want to immerse yourself in. Seasonal eastern sunrise views, and protected land along the border. Inside, an addition framed around the home's own eighteenth century posts and beams opens the kitchen through to a sunroom. Two fireplaces and two wood stoves, one a wood cook stove in the mud room. Wide boards, quartz counters, nothing waiting to be done. 500 feet of road frontage, and then the road ends. One neighbor, out of sight. The quiet is complete and the night sky extraordinary. 20 minutes to Lee, 30 to Great Barrington. What we call Heaven. An add'l 45 acres is available

October Mountain views and cows grazing across the road set the bucolic scene for this 2022 Cape Cod style home nestled on 3.10 acres on a private cul de-sac near Laurel Lake, Lenox, Stockbridge and many cultural and seasonal attractions of the Berkshires. A long-paved driveway, front porch, rear deck overlooking private backyard with western cedar post and rail fencing.,10 x14 shed, owned 9.6kW Tesla solar with two Powerwalls (seller reports no electric bill), central air, high efficiency natural gas heating system, Rinnai on demand hot water. Oversized attached two car garage leads to enclosed mudroom, beautiful eat-in kitchen, front living room w/gas fireplace, lst floor primary suite, second bdm., laundry/ half bath. Second floor offers two generous bdms., open landing and a full bath.

Some homes feel as though they belong in the pages of a novel. Here, life unfolds at a gentler pace, with mornings spent listening to Tophet Brook, afternoons beneath the trees, and evenings gathered around the warmth of a brick fireplace. This inviting countryside home offers room to welcome family and friends, whether baking together in the kitchen during the holidays or lingering over conversations long after dinner. A private first-floor primary suite and thoughtfully arranged guest quarters provide a balance of togetherness and personal retreat, while the deck and fenced backyard invite you to enjoy the changing Berkshire seasons. More than a house, this is a place to leave the rush behind, find joy in the everyday, and make room for what matters most.

ARRIVE FRIDAY NIGHT, UNLOCK THE DOOR & ENJOY THE WEEKEND! Turnkey Berkshire get-away in an exceptional location. Beautifully maintained and ready for immediate enjoyment, this inviting Egremont home requires no updates and offers comfort, privacy, and convenience. Features include a two-car attached garage and generator for effortless year-round living. Ideally positioned near skiing, scenic hiking, exceptional dining, and the vibrant villages of Great Barrington & Egremont, with easy access to New York and Connecticut. Egremont's attractive property taxes add to the appeal. A rare opportunity to simply arrive, settle in, and enjoy all that the Berkshires have to offer

Your own sports compound and sanctuary tucked away on a quiet Great Barrington road: this private four-acre retreat centers around an in-ground heated swimming pool and a dedicated tennis/pickleball court framed by natural landscape. Inside, clean mid-century architectural lines deliver remarkable flow, highlighted by two fireplaces, four bedrooms, three baths, space to work from home, and a sunroom overlooking the grounds. Substantial energy upgrades include a high-output ground-mount solar array and an updated heating system that keep operational costs remarkably low, offering a turnkey private playground just minutes from downtown dining, skiing, and cultural landmarks.

A rare opportunity to become the next steward of a remarkable piece of Sheffield history. Dating to 1819 and prominently situated on South Main Street in Sheffield's Historic District, this extraordinary antique is filled with the character, warmth, and craftsmanship of another era. Currently configured as a four-family residence, the property includes three beautiful apartments in addition to the spacious main portion of the home, allowing an owner to enjoy gracious historic living while rental income helps offset expenses. Alternatively, rent all four residences and take advantage of a distinctive investment opportunity. Gorgeous grounds and an exceptional historic setting make this a truly special Sheffield property.

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.

From the welcoming front porch to the warmth of its pine-ceilinged family room, this 4-bedroom, 3.5-bath Colonial feels like a place to settle in and stay awhile. Set well back from the road, it offers nearly 4,000 sq ft with room to gather and space to yourself. The stone fireplace & skylights make the vaulted family room a natural gathering place, open to the kitchen featuring quartz countertops with a waterfall edge, a built-in desk and a breakfast nook. Separate formal living and dining rooms offer space for celebrations, conversation or a quiet evening. The first-floor primary suite offers a retreat of its own, with an office, two walk-in closets, a double vanity, jetted tub and direct access to the deck and backyard. Laundry and a half bath complete the main floor. Upstairs, three

Gracious, elegant, and designed for living well, this exceptional center hall Colonial offers timeless character, beautiful mountain views, and an abundance of space. The welcoming entrance is accented by exquisite English stained glass, with wood floors flowing throughout the home. Five bedrooms and 3.5 baths provide room for family and guests, while grand living and dining rooms are perfect for entertaining. A spacious family room offers a more relaxed gathering space. The primary suite features cathedral ceilings and beautiful mountain views. Outside, covered patios and decks overlook a spectacular in-ground pool, gazebo, and bathhouse--creating a private setting for summer entertaining and relaxation. Thoughtful updates include a 2016 roof, 2023 driveway, and appliances updated 2023-26

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.

Stunning light filled Twelve Oaks unit. The main floor offers easy one level living with open common spaces. Great room with vaulted ceilings, wall of windows and gas fireplace, dining area with private screened porch and deck access, kitchen with large island and ample storage. Primary with en-suite bathroom, new cork flooring and walk in closet. Half bath, laundry and den complete the first floor. Second level boasts two oversized guest bedrooms, both with en-suite full baths. The loft overlooking the great room makes for useful flex space. The lower level walkout includes a large family/game room, fourth bedroom, full bath and storage room. Enjoy the association clubhouse, exercise room, pool and tennis court. Located in a most convenient location!

Dreaming of your own private sanctuary? 30+ acres await exploration! Enter between two stone pillars and the long winding driveway will take you past woodland glades, open spaces, mature tree stands, manicured lawns and a magnificent spring-fed swimming quarry! Acres of open cleared land afford additional usage options. Cedar log home, one-owner custom built. Large wrap-around deck and long covered porch; great for summer entertaining! Inside you'll enjoy over 2000 sf of relaxed country living. Great room with vaulted ceiling, massive stone fireplace. Open kitchen w. granite counters and island w seating. Two first floor bedrooms and full bath. Upper level with spacious primary suite and an open loft with fireplace. Finished walk-out lower level w. 2 car garage. Truly one-of-a-kind!