Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26.

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite—pool, fitness center, clubhouse, and tennis—all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite—pool, fitness center, clubhouse, and tennis—all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.

This iconic building has been home to one of the Berkshires most beloved businesses for over 50 years. Built in 1731 as the Egremont Tavern stage coach stop, it was expanded in the 1960s. The 2.2 acre lot provides substantial parking. The historic front section offers unique features like stone floors and exposed beams and fireplaces. The rest of the building consists of a series of lovely rambling spaces with rustic elements on the main and lower levels, and two rental apartments upstairs (one 3/1, one 1/1). This property offers a buyer an extraordinary opportunity: own an incredible income producing property in the bustling town of South Egremont.

A rare opportunity to experience a lakefront living on beautiful Lake Buel. This distinctive log cabin captures breathtaking water views from nearly every room and is filled with natural light. The dramatic great room features a soaring cathedral ceiling with exposed beams, rich wood floors, and a handsome fireplace, creating an inviting setting for both intimate gatherings and grand entertaining. Designed for effortless one-level living, the home offers four bedrooms and three full baths, including a private primary suite with en-suite bath, plus a dedicated office. A generous deck overlooks mature landscaping, the lake and private waterfront with dock which is an idyllic setting for morning coffee, and summer gatherings. A truly exceptional Berkshire lake retreat. A must see!

Imagine never tiring of your own backyard. Nestled on one of the prettiest roads in Hillsdale, this beautiful single-level home is a front-row seat to rolling meadows, distant hills, and the quiet magic of the changing seasons. This sun-drenched, single-level home offers an effortless lifestyle framed by stunning, panoramic views. Inside, an expansive open floor plan invites the outside in. The thoughtfully appointed, updated kitchen flows seamlessly into a generous living area anchored by custom built-ins and a cozy wood-burning fireplace. Wall-to-wall windows grace the formal dining room, ensuring every meal is accompanied by breathtaking scenery. Both the living and dining rooms offer direct access to a sprawling rear deck, perfect for entertaining.

Rare opportunity to own a commercial store front on the iconic Railroad Street in downtown Great Barrington. Great investment property with two filled store fronts. Options available to increase a larger footprint.

Sun Filled Historic Reproduction Home Built in 2004 seamlessly blends old-world charm with contemporary comfort. Set on 1.82 acres with sweeping mountain views, this 3-bedroom, 2.5-bathroom home features meticulous hand-crafted details throughout-honoring traditional design while offering the conveniences of modern construction. The welcoming gourmet eat-in kitchen is perfect for everyday living & entertaining. Step out to the inviting covered porch-an ideal spot to savor morning coffee & evening sunsets with mountain vistas. The primary suite captures stunning views, while the expansive yard provides additional room to roam. 2-car oversized garage. Secluded setting just minutes to downtown Gt Barrington & Berkshire attractions.

Jaw-dropping water and sunset views from every room define this beautiful contemporary overlooking Lake Garfield. Offered fully furnished, this Berkshire retreat features a chef's kitchen flowing into a light-filled great room and screened porch. Four bedrooms -- including an ensuite primary -- plus a spacious family room offers plenty of room to gather. Linger on the screened porch, entertain on 2 decks, or unwind in the hot tub as the sun sets over the water. Privately sited on 2.5 acres, this is refined Berkshire living -- a truly magical place to escape, gather and enjoy.

Uncommonly Superb View -- A Vermont Meadow Retreat Tucked quietly into a broad meadow and surrounded by lush Vermont landscape, this property enjoys one of those rare, completely unspoiled western vistas: a full, harmonious sweep of the Taconic Mountain ridgeline, framed perfectly within human scale. The almost 40 acre setting--meadow bordered by deep woodland--creates a sense of arrival, privacy, and permanence that is difficult to replicate. The architect designed home blends natural materials inside and out, offering a calming, organic environment that feels inseparable from the land around it. One of the sellers' guiding goals the architect skillfully interpreted, was harmony with the landscape, expressed most beautifully in the roofline: ... (see more)

Fabulous historic church. Located in the Stockbridge hamlet of Interlaken. Quiet and exclusive neighborhood just off Rt.183. Stylishly decorated by a renowned architect and designer. High ceilings, huge windows, and mahogany fittings. Beautifully restored kitchen with many original details. Marble topped sink/counter. Walk through to the magnificent living area to step back in time to an earlier era. Then on to the nave to enjoy soaring ceilings, oversized windows and room for entertaining. Enjoy this 'party space.' Or use for an artist studio, recording studio or any pastime that needs space. Minutes to Berkshire Botanical Garden, Tanglewood and the center of Historic Stockbridge.

Historic 9-Unit Bed & Breakfast | ±10,560 SF on ±0.33 Acres Exceptional opportunity to own a beautifully maintained three-story historic bed & breakfast offering approximately 10,560 square feet on a ±⅓-acre lot. Within walking distance to the downtown theater/business district. This well-appointed property features nine unique guest suites, each with private baths and kitchenettes, blending classic charm with modern amenities. Large parking lot in the rear of the property also offers a separate right of way directly onto East Housatonic St. Guests are welcomed through an elegant entry foyer, leading to inviting common spaces including a parlor, formal dining room, and fully equipped common kitchen. The first floor also includes two spacious guest suites.

Imagine owning your own secluded sanctuary, where total privacy and tranquility are yours for the taking. This extraordinary property offers the rare opportunity to build your dream retreat on a breathtaking piece of land, untouched by the outside world. With 20-foot-tall mountain laurel trails leading to the top of a mountain with stunning views right at your doorstep, you'll have endless access to nature's beauty, all while remaining completely secluded. The land consists of 6 separate parcels, all being sold together, creating the perfect canvas for whatever you envision. Don't miss out on staking your claim to this hidden gem, an unparalleled escape !

Discover this sleek 2022 contemporary set on a beautifully landscaped parcel of just over 2 acres. Thoughtfully designed for low-maintenance, efficient living, this home offers 3 bedrooms, 3 bathrooms, and approximately 2,400 square feet, with every detail crafted for both beauty and everyday convenience.

Elevated Living - Inside and Out! Exceptional design and craftsmanship distinguish this stunning home. The single-level interior is warm, sophisticated and filled with natural light, with the kitchen, dining and living areas flowing together in one open space surrounded by specialty windows and French doors. Set on four private acres amid the highest peaks in South County, the home offers immediate access to premier hiking and protected lands. Locally sourced Massachusetts walnut floors, Scavolini cabinetry, Miele and Sub-Zero appliances, extensive custom woodwork, shoji-inspired glass sliding doors, and a dramatic stone fireplace wall speak to the quality and attention to detail throughout.

A DRILLED WELL, A COMPLETE 6 BEDROOM SEPTIC SYSTEM, A HORSE BARN AND A SHED COMES WITH THIS FABULOUS 42 PLUS ACRE PARCEL. BEAUTIFUL STONE WALLS SURROUND THE BUILDING SITE AND ACROSS FROM PROTECTED LAND

Tucked away at the end of a long driveway and perched atop its own private hill, this stunning 3-bedroom, 2.5-bath post-and-beam home offers complete privacy and breathtaking mountain views. The open floor plan is centered around a dramatic floor-to-ceiling fieldstone wood-burning fireplace, with soaring ceilings, exposed beams, and beautiful pine floors throughout. The primary suite includes a private bath, while two additional vaulted-ceiling bedrooms share a full bath. Enjoy central AC, a metal roof, board-and-batten siding, portable generator hookup, and a large dry basement for storage. Outside, relax on the expansive rear deck, swim in your spring-fed pond, fish on a lazy Sunday afternoon, and enjoy spectacular sunsets and incredible stargazing from your own hilltop retreat.

Gracious, stately, and filled with distinct warmth, this impressive Colonial is a rare offering of exceptional scale and character. With more than 4,300 square feet, five bedrooms, two and a half baths, and an abundance of beautifully proportioned gathering spaces, the home offers an extraordinary sense of presence while remaining remarkably welcoming. Original detail remains beautifully intact, including exquisite wood trim, handsome hardwood floors, a grand stairway, and elegant bay windows. Huge windows and wonderful natural light illuminate the large, gracious rooms throughout the day, highlighting the craftsmanship and timeless beauty of the home.

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio

*** MOTIVATED SELLER**Nestled in the heart of Great Barrington, this spacious 4 bedroom, 4 bathroom residence offers the perfect blend of family-friendly comfort and private sophistication. The home greets you with gleaming wood floors and a stunning fieldstone fireplace that anchors the living spaces in warmth and character. Cook like a chef in the large open kitchen, where generous countertops, a welcoming island, and ample natural light inspire everyday gatherings. The first-floor primary suite provides convenience without sacrificing privacy, ideal for busy households seeking single-level living when desired. Step outside to your expansive outdoors: a grand deck that overlooks lush acreage, plus a screened-in porch and an oversized porch ideal for morning coffees,