Tucked into the rolling hills of Great Barrington just minutes from downtown and the slopes of Ski Butternut, The Turning Point is a storied 3,600-square-foot Berkshire landmark operating as an active short-term rental. Steeped in history dating back to its 1800s stagecoach tavern roots, the property showcases an enduring dual-facade of classic New England brick and weathered clapboard. Inside, original period charm takes center stage with wide-plank wood floors and glowing fireplaces, perfectly paired with a rare, substantial footprint featuring 7 generous bedrooms and 6.5 bathrooms. Designed for effortless hosting, this expansive retreat offers an incredible canvas for a lucrative rental investment, a boutique bed-and-breakfast, or a magnificent private country compound.

Tucked away on a private cul-de-sac, this stunning 4-bedroom, 2.5-bath residence combines elegant upgrades with an effortlessly open and sun-drenched floor plan.The main-level primary suite is a true retreat, offering a walk-in closet and a beautifully appointed en suite with radiant heat tile, a soaking tub, and marble finishes. A convenient first-floor laundry room and a mudroom directly off the garage add everyday practicality without sacrificing style.Three additional bedrooms and a full bath complete the upper level. The walkout basement, already plumbed for a bath, presents exceptional finishing potential.Outside, an expansive deck with a pergola, an above ground saltwater pool, storage shed, and two-car garage round out this exceptional offering.

Set on 5.8 acres high on the east face of Mt. Fray (Catamount), ''The Pod'' is a mid-century timber and glass octagon. Surrounded by thousands of acres of protected land with expansive views; trails on the property connect to Catamount, Bash Bish Falls and beyond via the South Taconic Trail. Two streams -- one just behind the house -- run through the property. Upon entry from the wrap around front deck, you are in the open plan living/dining/kitchen space -- outside is inside through floor to ceiling glass. Moving through you'll find the original ''one piece'' modular bathroom in excellent condition, the primary bedroom, and a den/guest room with sliders opening onto a large stone patio cut into the slope. Secluded yet convenient: Great Barrington 12m, Hudson 30m, Hillsdale 10m

Build to suit. This new ranch construction modular home offers an open concept on a double lot. The home features sun-filled spaces with an open floor plan that is designed to capture Pontoosuc lake and mountain views from the dinning, living & primary bedroom. 4 bedrooms 2.5 baths. Lower level ready for additional finished space. Purchase as specked or chose upgrades to finish home to your desires. Lake access available within walking distance. Building plans available at request.

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.

Beautifully renovated one-level ranch offers the perfect blend of modern convenience and cozy charm. With 3 spacious bedrooms and a well-appointed bathroom, this home is designed for comfort and easy living. Step inside to discover a sunlit living space showcasing modern upgrades throughout, including energy-efficient fixtures and a sleek, new kitchen equipped with top-of-the-line appliances. The open floor plan is perfect for entertaining, seamlessly connecting the living, dining, and kitchen areas.One of the highlights of this home is its commitment to sustainability, featuring solar panels that significantly reduce energy costs. Lots of outdoor space and 2 separate outbuildings with car port. Additional plans available. Separate Screened in porch

Tucked at the end of a peaceful cul-de-sac, this 3,300+sqft Cape is a rarity in today's market - a sprawling main home with the addition of a separate in-law/guest apartment. The main wing shines with refinished wide-plank wood floors, gas fireplace, and premium renovations, including a new chef's kitchen and bathrooms. Upstairs features three gracious bedrooms, including a primary suite with massive walk-in closets, en-suite full bath, and secret spaces awaiting your imagination. The private apartment--with its own entrance, full kitchen, den, and 2 bedrooms, is ideal for guests, income, or multi-generational living. Enjoy proximity to downtown Lee's dining and golf, all while being under 10 minutes to downtown Lenox and Stockbridge. A multi-generational gem in a prime locale!

Fall in love with this renovated 3BED 2BATH house located just a stone's throw from downtown Stockbridge on nearly half an acre. Inside, the open layout features a cozy living room anchored by a classic fireplace. The kitchen has granite countertops and an expanded pantry with new custom shelving. The primary suite boasts a custom walk-in closet, an updated bathroom and direct access to the backyard. Two additional bedrooms share a 2nd full bathroom. Excellent functionality extends to the basement, which has new custom storage closets. Enjoy your morning coffee from the screened-in porch or step out onto the newly refinished back deck. Entertain in the the partially fenced yard with a new paver patio and built-in fire pit. Move-in-ready at its finest. Furnishings available to purchase

Set high up on a knoll, this home boasts good, solid construction, wood floors throughout and an easy, manageable floor plan. Within walking distance to Main Street, this adorable home has been lovingly cared for. Immaculate condition, a cozy fireplace and a detached garage. A sweet place to call home in a convenient location. So much potential but move-in ready. The yard has perennials & mature trees and privacy. One block from NYC bus stop, restaurants, shops and markets.

Be wowed by this southeast sleeper that appears to be a traditional-style Colonial instead it's updated with custom luxury features, stylish finishes, and offers exceptional indoor-outdoor living. Modernized inside and out, a unique homesite, a welcoming front porch, a flat side yard ideal for play and swings, a spacious deck, a Goshen stone patio, and a hilltop wooded retreat. Begin your tour inside with in the awe-inspiring heart of the home beautifully designed kitchen with quality cabinetry, top-of-the-line Bosch appliances, quartz counters, and a sleek tile backsplash that blends artistic symetry with everyday function. The centrally placed coffee-bar buffet is perfect for morning coffee, casual entertaining, or signature summer cocktails with friends and neighbors.

Enchanting Egremont! Set atop a private drive on 5.3 acres in Egremont, this thoughtfully designed residence offers a rare balance of seclusion and accessibility. Surrounded by nature and positioned for easy access to the Taconic State Parkway, the property captures the essence of Berkshire living. At the heart of the home is a dramatic living and dining room defined by a soaring two story ceiling, skylights, an interior balcony, and a wood-burning fireplace. Filled with natural light, the space creates a striking setting for both everyday living and entertaining.

This beautifully positioned Berkshire retreat offers the perfect blend of privacy, comfort and natural beauty. Nestled on a peaceful country road, this inviting home is surrounded by scenic woodlands and mountain views while remaining conveniently close to the cultural attractions, outdoor recreation, and vibrant communities that make Berkshire County so desirable. Inside, you'll find warm and welcoming living spaces, ideal for both everyday living and entertaining. Enjoy a quiet morning coffee overlooking the views or simply unwinding after a day of hiking, skiing, or exploring the Berkshires, this property delivers the lifestyle buyers search for. An oversized heated workshop/garage with artist loft & half bath is simply magnificent for a multitude of occupations or hobbies. Incredible

ANTIQUE CENTER HALL COLONIAL ON NEARLY AN ACRE in the charming village of Southfield. Built in 1799, this spacious historic home has high ceilings, wideboard floors, and many original details. The first floor has a living room with a wood-stove, bedroom with adjacent full bath, den/office with a wood-stove, and a large, open kitchen/dining area. Glass doors lead to a porch overlooking nearly an acre of gorgeous land and gardens. A pantry area leads to an attached studio perfect for an artist/workshop. Upstairs, are two bedrooms which share a full bath, and unfinished attic space with tremendous potential. A stone's throw from The Southfield Store, a cafe serving breakfast, lunch, and sometimes dinner. 8 minutes to York Lake for swimming and hiking. 20 minutes to Great Barrington.

Bordering protected land and moments from the Appalachian Trail, this light-filled contemporary offers privacy, comfort, and an easy connection to the natural beauty of the Berkshires. Set on one acre in a peaceful Sheffield location, the home features vaulted ceilings, open gathering spaces, and a flexible layout designed for both everyday living and entertaining.The spacious kitchen flows into the dining and sitting area with direct access to the deck, creating an inviting indoor-outdoor feel. The living room is anchored by a beautiful gas fireplace and oversized windows that bring in natural light throughout the day. Three well-proportioned bedrooms include a primary suite with spa bath.

IMMACULATE 3 BEDROOM COLONIAL with IN LAW APARTMENT in SOUTH LEE on a quiet cul de sac. Zoned 2 family, Partially fenced back yard, attached garage and central air conditioning. Great investment or family home.

Renovated Gothic Barn in an Unbeatable Berkshire Location. Location, Location, Location! This beautifully renovated Gothic Barn offers timeless architectural character paired with modern comfort and convenience. Move-in ready, this exceptional property features 3 bedrooms, 3 full bathrooms, and an impressive list of high-end upgrades throughout. Enjoy peaceful mornings and scenic sunsets from two brand-new decks overlooking picturesque views. Inside, the home has been thoughtfully updated with Andersen windows, doors, and sliding glass doors, durable Hardie Board siding, fresh interior and exterior paint, refinished hardwood floors, and central air conditioning. The stunning chef's kitchen is equipped with Café appliances, granite countertops, and premium finishes, while all three

The keyword for this spacious Richmond Shores 2 bedroom with extra loft sleeping space/2 bath lake property is ''new''! New roof, new hot water heater, new refrigerator, new wiring, new thermostats, new well pump, AND new sewer pump! This turnkey house is perfect as a getaway, downsize or investment property. Enjoy the spacious backyard with canal access to Richmond Pond, with a community beach and public boat ramp close by. Spend the colder months toasty warm by the stone fireplace with new fireplace insert and you're only 5 miles from Bousquet!

Welcome to 28 Mountain Pond Lane, a stunning raised ranch nestled on a private 3.29-acre parcel in New Ashford, MA. This charming home features 3 bedrooms and 2.5 baths, eat in kitchen & great room currently used as a studio offering ample space for comfortable and flexible living. The oversized 3-car garage provides plenty of storage, while the large multi-tiered deck and beautiful concrete patio in the rear create the perfect outdoor oasis for entertaining or relaxing. Surrounded by mature gardens, this property exudes tranquility. Additional highlights include a backup generator and various other features that enhance the home's appeal. Experience serene living in this picturesque setting--your dream home awaits!

Completely renovated New England farmhouse offering the perfect blend of historic charm and modern convenience. Thoughtfully remodeled throughout with updated kitchen, baths, systems, and finishes while preserving the character and warmth of a classic Berkshire home. Bright, inviting living spaces, abundant natural light, and quality craftsmanship create a move-in-ready residence with potentially two primary suites, one up and one down.. Conveniently located near Gt Barrington's shops, restaurants, Berkshire County cultural attractions and ski/outdoor recreation. A rare opportunity to enjoy modern living in a beautifully restored farmhouse with lush private setting and fenced yard. A garden level pergola with seating area invites conversation with family and friends in complete privacy.

Set in one of Southeast Pittsfield's most desirable neighborhoods, this very sunny and impeccably maintained home offers the perfect balance of gracious living, flexible space, and effortless entertaining. Lovingly cared for by its current owner, the home unfolds with elegant formal rooms, hardwood floors, and a warm wood burning fireplace anchoring the living room. The heart of the home is an open concept kitchen and family room with cathedral ceilings, where sliders lead seamlessly to a large rear deck overlooking a spacious, flat, and fenced backyard; ideal for gatherings, play, or quiet relaxation amid mature landscaping and beautiful gardens.