Just outside the charming village of Housatonic, this extraordinary Queen Anne Victorian stands as a true architectural gem, nested amid lush gardens and beautifully landscaped grounds. From its distinctive urn shaped columns to its twin towers, gables and wrap around porch, every detail reflects the grace and grandeur of a bygone era - balanced perfectly with thoughtful modern updates. Sweeping lawn with private patio and mature plantings. Currently configured as a two family residence, the layout offers easy conversion back to a magnificent single-family home, making it ideal for a grand Berkshire retreat, full time residence, or multi-generational living. Inside you will find historical character, original millwork & trim, and updated kitchens & baths. Whether you're seeking a stately

Escape to the Berkshires nature's preserve out your door overlooking Mass Audubon land to experience the ultimate easterly mountain and meadow view while in the midst of city conveniences and pleasures. Surprisingly exceptional views can be enjoyed from most rooms influencing your mind and spirit with a calming energy. This treelined one way street enhances the quiet and peaceful essence of the beautiful Berkshires. A charming neighborhood offers close-in city conveniences and pleasures near the Upstreet Cultural District yet minutes to Lenox dining and Tanglewood. Hike or snowshoe at Canoe Meadows bordering your .80 acres, bike October Mt.and kayak nearby. This stately and solidily constructed home is impeccably improved with an eye for design and quality. Restoration Hardware f

Situated on Great Barrington's highly sought after neighborhood of 'The Hill', 11 Prospect delivers on style, convenience and of course, location! This four bedroom home with two and a half baths over three floors and hardwood floors throughout, offers lots of room for family and friends. An oversized screened in porch, attached two car garage and a finished basement are just some of the 'must haves' to enjoy in this recently updated property. Steps away from the shoreline of Lake Mansfield and a simple stroll to downtown Great Barrington's many coffee shops, restaurants, bakeries and theaters, this property is the perfect move in ready home!

Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, BUpstreet Cultural District and is ideally just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved over this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring guest house featuring 3 bedrooms, 1 bath plus a first floor in-law bedroom suite and a 2 car garage, if one so chooses to accommodate extended family, friends or caregiver

PANORAMIC VIEW, PRIVACY AND A STUNNING CONTEMPORARY is waiting to become your country sanctuary. As you drive up the long, private driveway, you feel your shoulders relax and then..peaceful thoughts take over as you soak in the sweeping south west view at the top of your private hill. The multi-level design of this home offers living with peace and tranquility for both gathering and quiet time alone, all while capturing the nature surrounding you on 5+ acres. Main level bedroom with private deck, full bath, office, cozy den and open kitchen/dining with direct access to the attached 3 car heated garage for convenience, dramatically opens to the Great Room in one direction and the primary bedroom with fireplace and newly designed luxurious ensuite bath with another guest bedroom and bath on

Welcome to The Vanna Building at Winden Hill. An excuisite example of Period living, this sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms and two baths on the second floor. The primary suite comes with an oversized walk out deck large enough to place your summer lounge furniture, the perfect spot for your morning coffee. Amenities at Winden Hill include a heated pool and a tennis and pickleball court....all this and and only a 20 minute stroll to the center of Lenox. This truly is the perfect place to call home.

This historic 4-bedroom 3.5-bath home sits on a beautifully landscaped 1-acre lot surrounded by ornamental trees, vibrant flower gardens and mature plantings. Originally built around 1800, this comfortable well-maintained house features high ceilings, warm wood flooring, and plenty of period charm. The main level welcomes you with a spacious living room accented with Greek Revival moldings, an expansive bay window with built-in window seats, and an inviting wood-burning fireplace. Nearby, a charming den offers another wood burning fireplace and quiet spot to relax with a book. Off the living room, the formal dining room can comfortably accommodate a large crowd at holiday gatherings...

This is the one you've been waiting for. A classic mid-century home on over 4 private acres, offering the ultimate Berkshire lifestyle. The bright, open-mid century floor plan provides a seamless flow, while two fireplaces add classic comfort. The home features 4 bedrooms, 3 baths, large office and a media room, offering flexibility for family and guests. Outside, your private resort awaits. A beautiful heated swimming pool and a dedicated tennis court provide endless recreation. The expansive grounds, located at the end of a quiet road, guarantee unmatched privacy. Plus, a large solar array and new heating system drastically cuts utility costs. Enjoy total seclusion while being in the middle of everything that makes Great Barrington one of the most desirable towns in the Berkshires.

FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for single-family, multi-unit, or live/work conversion--with no sprinkler system required for up to 3 residential units. Already equipped with 1 full bath and 4 powder rooms, and featuring two finished floors, the layout adapts effortlessly to your vision--be it modern apartments, stylish offices, retail space, or a dynamic studio. Spacious and bright with 5,180 sq ft across two levels Excellent bones

GORGEOUS LOW MAINTENANCE HOME IN LOW TAX EGREMONT. A move-in ready opportunity, just minutes to the NY & CT borders AND Great Barrington. This home is ready for occupancy just in time for Ski Season. Wonderful chef's kitchen with open plan Living/Dining. The upper level hosts a grand primary en- suite, with a dedicated office space and seating area, AND its own screened porch. Two additional Bedrooms and full Bath provide total comfort for family and guests. The expanded deck, fire pit and level yard great for family & friends. Two car attached garage, Generator, and meticulously maintained grounds. Custom shed, has studio or play house potential. Dog fenced area. Hy's Fried, Egremont Barn & Catamount Ski area minutes away. Trains 20 minutes away.

Berkshires Sanctuary - A Fully Renovated Retreat with Appalachian Trail Access & Nearby Three Mile Pond.Tucked away in a landscape of towering trees and rolling hills, this exquisite four-bedroom and three-bathroom, retreat has been reimagined with over $650,000 in premium renovations, offering the perfect balance of luxury and nature. With direct access to Appalachian trail and Three Mile Pond, just minutes away, this home is a haven for those who crave both serenity and adventure.Where Modern Elegance Meets Natural Beauty A Grand Welcome - A wraparound deck, inground pool, and upper balcony invite you to take in the forested surroundings, framed by black aluminum railings and Trex boards built for beauty and longevity.

Nestled on 36 private acres, this contemporary home offers breathtaking mountain views and an extraordinary blend of modern design, energy efficiency, and meticulous craftsmanship. The multi-level open floor plan features sun-drenched rooms, soaring cathedral ceilings, and stunning architectural details throughout.French doors create a seamless indoor-outdoor flow, leading to expansive decks and a patio complete with a hot tub, perfect for entertaining or relaxing among the lush perennial gardens. The sunroom overlooks a serene swimming pond and gazebo and sits conveniently beside the kitchen, which is outfitted with granite countertops and stainless steel appliances.Constructed with green technology this residence is both eco-conscious and structurally superior.

A unique farming opportunity on a self-sufficient 51-acre parcel, highlighted by an 1802 antique Colonial exuding historical charm. A thoughtfully conserved agrarian sanctuary with organic soil, a fruit orchard, maple sugar house, trails, gated pastures, and a running brook. The large barn and mature gardens are framed by stone walls and outbuildings. Bright rooms with wood floors, antique beams, 4 fireplaces with generous common spaces ideal for family or community living. Sustainable energy solutions: grid-tie solar, photovoltaic hot water, a hydronic wood boiler and on-demand hot water, ensure economic fuel usage. A soulful property reflecting American heritage offering privacy & tranquility. A unique opportunity for farm-to-table living, historical immersion and rural sustainability.

A remarkable offering of this restored 18th century Georgian home built in 1764 on almost 4 acres with the possibiilty of an additional building site as part of the listing price; with an early barn and shed opposite the Clark Art Institute. Once located on Main St where the College President's house now sits, it was moved by oxen to its current location in 1800. (RRBrooks.)Restoration efforts follow the Deerfield tradition of interior feather-edged sheathing and paneling, wide pine board flooring and a large colonial cooking fireplace with adjacent beehive oven in the keeping room. 4-5 bedrooms/3.5 baths.

Discover this enchanting 1900s Town Colonial, where historic charm meets modern sophistication. Nestled in a tranquil neighborhood, this home offers four spacious bedrooms, two updated full baths, and a stunning chef's kitchen, blending comfort with style. From the moment you enter through the newly renovated mudroom, you'll appreciate the original wood floors and built-in shelving that preserve the home's historic character. The first floor features a convenient en suite bedroom. The heart of the home, the chef's kitchen/dining room is a culinary delight equipped with top-of-the-line appliances and ample counter space. Partially renovated barn. Nice yard.

This 1700's-era former inn has been recently renovated from top to bottom, preserving its historic New England charm & seamlessly blending all the modern amenities for a comfortable country cottage lifestyle. The home offers 4 bedrooms and 4 baths over 3 generous levels of living areas. The ground level first floor features a cozy & inviting great room with decorative antique fireplace and new radiant heat, a connected yoga studio/home office, also with radiant heat & a full bath, and a very convenient and efficient mudroom & adjoining laundry room. The main floor features an open country kitchen and dining area, charming parlor with fireplace, and a first floor primary bedroom suite with modern bath and walk-in closet.

TURN-KEY Nestled on 19.2 private, bucolic acres, this meticulously maintained 3-4 bedroom/3 bath log home is being offered fully furnished with numerous upgrades, all within the past 3 years. 1st floor features an open floor plan with hardwood floors, vaulted ceilings, an abundance of natural light, along with the convenience of a 1st floor laundry and full bath. 2nd floor is home to a generous loft, spacious primary bedroom w/ensuite bath, 2 additional bedrooms and full bath. Entertain year-round on your new trex deck and throughout manicured grounds; enjoy N.E. winter nights fireside by your new gas fireplace and bluestone/cultured stone hearth! All representations are from the seller or public source; broker has not verified same. Recommended buyer independently verify all information.

Your waterfront lifestyle begins at this Hayes Pond sanctuary. From sunrise paddles to sunsets savored from the deck, this home is your private four-season escape in the Berkshires. The modern, open interior is designed to celebrate the water, with soaring cathedral ceilings and a wall of windows that frames the stunning lake view. A cozy wood stove, bright sunroom, and a large deck provide perfect spaces for relaxing or entertaining. This 4-bedroom retreat includes a primary suite featuring a calming soaking tub. Your private, grassy shoreline is your personal gateway to the lake--perfect for launching kayaks, fishing, swimming, or the occasional bonfire. This is the ultimate waterfront escape, where every detail is focused on a life lived by the water.

Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, Upstreet Cultural District and is ideally just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved over this long term owners' commitment to preservation and restoration. This prominent manor style home may be coupled with the neighboring guest house featuring 3 bedrooms, 1 bath plus a first floor in-law bedroom suite and a 2 car garage, if one so chooses to accommodate extended family, friends or caregivers

Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming gazebo and a generous deck, perfect for hosting gatherings or relaxing in your own outdoor oasis.The oversized garage provides ample storage and includes a versatile space above, ready for your expansion ideas. With rough plumbing and electrical already in place, customizing this area is effortless. Located 2 min from Monument Mountain Reservation and 6 min to Main Street.