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.

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.

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.

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

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.

*** 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,

Welcome to Merritt Farm - The original home built in 1780 oozes with charm. Front of the house faces south with a large heated sun porch flanking the west side overlooking the pool and tennis court. The main floor rambles with a front parlour, a keeping room off the kitchen with back stair, formal dining and office. In 2008 a large studio addition was added with a first floor primary, full basement and heating system supplying the kitchen and boot room with radiant heat as well as the studio. Second floor has two additional bedrooms, one with a large deck over the sunporch and a generous hall bath. Over 35 acres with mature landscaping, gunite pool and tennis court nicely tucked away this property is set up to be the modern homestead.

Blending historic craftsmanship with modern comfort and versatility, this exceptional Berkshire estate presents a truly unique opportunity. The stately home is in remarkable condition and beautifully maintained. Comfortable floor plan with a grand foyer with sweeping staircase, expansive kitchen with butler's pantry, formal living spaces, sun porch, and multiple covered porches. The luxurious primary suite offers a sitting room, balcony, sun porch, and spa-like bath. Three additional bedrooms, two baths and two offices complete the second floor. A finished third floor provides flexible additional space. Excellent mechanicals. Attached spacious garage that can park 4 cars in double tandem. Surrounded by mature grounds on 5.7 acres and within walking distance of village of Dalton . . . .

An excellent opportunity to blend immediate cash flow with long term upside in a desirable and growing area! An added advantage of this exciting property is its potential for short-term rental income, subject to local ordinances! Rare opportunity to acquire two apartment buildings totaling nine units in a convenient Adams location. These properties are thoughtfully updated throughout, with a newer roof, boilers, hot water, windows, electrical systems, and modern finishes. Kitchens are remodeled with stylish touches, including quartz countertops, newer cabinetry, and updated appliances. with stylish touches including marble countertops, new cabinetry, and updated appliances.

An excellent opportunity to blend immediate cash flow with long term upside in a desirable and growing area! An added advantage of this exciting property is its potential for short-term rental income, subject to local ordinances! Rare opportunity to acquire two apartment buildings totaling nine units in a convenient Adams location. These properties are thoughtfully updated throughout, with a newer roof, boilers, hot water, windows, electrical systems, and modern finishes. Kitchens are remodeled with stylish touches, including quartz countertops, newer cabinetry, and updated appliances. with stylish touches including marble countertops, new cabinetry, and updated appliances.

An excellent opportunity to blend immediate cash flow with long term upside in a desirable and growing area! An added advantage of this exciting property is its potential for short-term rental income, subject to local ordinances! Rare opportunity to acquire two apartment buildings totaling nine units in a convenient Adams location. These properties are thoughtfully updated throughout, with a newer roof, boilers, hot water, windows, electrical systems, and modern finishes. Kitchens are remodeled with stylish touches, including quartz countertops, newer cabinetry, and updated appliances. with stylish touches including marble countertops, new cabinetry, and updated appliances.

Magical Egremont setting. Step into timeless charm with the comfort and craftsmanship of a beautifully renovated 1860 home abutting Karner Brook. The brook flows just beyond the sitting room and deck overlooking the beautiful landscaping and bridge that leads to the garden and brand-new outbuilding. Offering three/four bedrooms, three bathrooms, and over 3,000 square feet, this distinctive property blends historic character with thoughtful modern upgrades, including cherry cabinetry, granite countertops, a Sub-Zero refrigerator, Viking six-burner range and hood, and two dishwashers. Wide-plank pine floors, beautiful woodworking, and a fireplace create inviting spaces throughout.

A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent century-old oak tree, and follow the gentle brook that borders the property. This remarkable landscape offers a rare combination of privacy, natural beauty, and accessibility. Create an incomparable estate overlooking the mountains, or take advantage of the property's three ready-to-build lots to establish a family compound nestled among meadows and woodland. Whether envisioned as a private retreat,