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

Discover a rare opportunity to own 181 extraordinary acres in the picturesque town of Adams. Available for the first time, this expansive property features an ideal blend of open meadows, rolling hills, mature woodlands and stunning views - perfect for nature lovers, outdoor enthusiasts, or visionary developers. The land boasts gently sloping topography from east to west, creating a dynamic landscape rich in wildlife and diverse ecosystems. Property borders Savoy Mountain State Forest to the east, providing direct access to hundreds of acres of protected land. Extensive frontage on East Hoosac Street and additional right-of-way access from East Road opens the door to potential development. Priced at just under $5,000 per acre, this is a unique opportunity in the heart of the Berkshires.

An exceptional commercial opportunity on busy Route 7 at the Sheffield-Great Barrington line, this 7.29-acre property offers over 1,000 feet of frontage and unmatched visibility. Formerly a GMC dealership and auto repair shop, the site includes a 5,540 sq ft garage with five oversized service bays and heavy-duty power--ideal for automotive, fleet, or light industrial use. An additional storage building on-site expands functionality.The expansive paved lot can accommodate over 100 vehicles, making it ideal for dealerships, rentals, or display. The location benefits from steady traffic, close proximity to tri-state area schools & businesses, and easy access to downtown Great Barrington's shops, restaurants, and cultural venues.

Modern Elegance Meets Tranquil Nature on the Clam River - a short ride to Gt Barrington on the Monterey Line! Tucked away on a private drive that gracefully winds over the scenic Clam River, this meticulously maintained residence is a hidden gem offering the perfect blend of sophistication and natural beauty. From the moment you arrive, the approach sets the tone--a tree-lined driveway leads to a thoughtfully designed home where every detail has been curated for elevated living. The main level features an open-concept layout anchored by a chef's kitchen with a full-length picture window that lets nature in. Soaring cathedral ceilings and an expansive window wall flood the dining and living areas with natural light, while a sleek 3-sided gas fireplace offers a warm focal point--

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.

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...

Rare Waterfront Offering on Prospect Lake - 10.5 Acres Across Four Subdivided Lots. Nestled along the tranquil shores of beautiful Prospect Lake, this extraordinary property presents a once-in-a-lifetime opportunity to own a unique and versatile slice of the Berkshires. With direct water frontage, lightly wooded acreage, and breathtaking western views, this is the perfect setting to create your dream retreat, family compound, or multiple home sites--all within a serene and private natural landscape. The land is lightly wooded, offering a blend of privacy and openness, with subtle clearings that invite sunlight through the trees. A network of light trails winds through the forest, ideal for peaceful walks, snowshoeing, or morning jogs. One of the lots features a charming pond,

Ready to move into New York style living in the Berkshires! This last unit available in this fabulous setting! Poised above Main Street Great Barrington, this Southworth Penthouse Condo offers 1,974 sq ft comprised of 2 bedrooms, 2 full baths, kitchen, laundry, storage, dining and living rooms with high ceilings and, views of East Mt. Walk to the heart of town, shopping, Coop market, restaurants, movie theater and, The Mahaiwe Performing Arts Center and more! Elevator access. Interior will be newly constructed beginning in Fall 2024! Proposed finished interiors included in photos.

Set on just over seven acres between Lee and Stockbridge, this c.1850 Greek Revival delivers classic Berkshire character with real scale. Nearly 4,700 square feet with a gracious flow, tall windows, and preserved period details. Every bedroom offers an en suite, creating an easy setup for hosting family and friends. Common spaces include a welcoming foyer, two living rooms, a formal dining room, a library, and a large cook's kitchen with eat-in area and pantry. Three period fireplaces add warmth and charm. Outside, mature trees frame open meadow, with room for gardens, games, and long summer evenings. The setting is remarkably convenient. Tanglewood, Lenox, Stockbridge, and downtown Lee are a short drive, and access to Route 7 and the Mass Pike keeps weekend trips simple.

A rare chance to own two attached full size charming houses in one of the most coveted neighborhoods! Abuts 30 acres of conservation land and offers direct access to The Spruces Park, Hoosic & Green River walk/ swimming area, public tennis courts, and Mohican multi-use bike/walk path! Original Home: (Built in 1953, updated in 2016) it has total privacy, deck, 2 bedrooms, 1 bath, a large living room with fireplace, full size eat-in kitchen and bonus rooms in the walk-out basement. Currently, Airbnb rental netting $20,000 per year for over 10 years. 2nd side is-Modern Addition (Built in 1985, fully updated in 2023-2025) 2 bedrooms, 2 bath, new kitchen, Brazilian oak floors. Additional bedrooms & recreation room, offices, workshop in lower level. So many features, see document tab & photo

The Country Village Condominiums on Copper Beech Lane remain Great Barrington's premier townhouse condos. Rarely available for sale, Unit 14 is one of few with a two-car garage and a wraparound deck facing south and west. This light-filled end unit offers privacy and three exposures. The kitchen features generous counter space and a bright breakfast area, while the living/dining room opens to the deck and side yard. Upstairs, the primary suite includes a walk-in closet and en-suite bath, with two guest bedrooms and another full bath. The garage and abundant storage are on the lower level. Enjoy the association pool, manicured grounds, and a short stroll to downtown--beneath the grand Copper Beech that inspired the name.

The Country Village Condominiums on Copper Beech Lane remain Great Barrington's premier townhouse condos. Rarely available for sale, Unit 14 is one of few with a two-car garage and a wraparound deck facing south and west. This light-filled end unit offers privacy and three exposures. The kitchen features generous counter space and a bright breakfast area, while the living/dining room opens to the deck and side yard. Upstairs, the primary suite includes a walk-in closet and en-suite bath, with two guest bedrooms and another full bath. The garage and abundant storage are on the lower level. Enjoy the association pool, manicured grounds, and a short stroll to downtown--beneath the grand Copper Beech that inspired the name.

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.

Nestled on 6.6 peaceful acres, this beautifully renovated country Cape offers exceptional privacy just minutes from town. Set well back from the road, the home enjoys a quiet, convenient location surrounded by mature trees and gardens.Inside, a spacious dining room features a striking stone fireplace, while the large living room showcases wood floors that extend throughout. Every detail has been thoughtfully updateda''from the brand-new roof, septic, and mechanical systems to upgraded electrical, plumbing, bathrooms, and a completely renovated kitchen. Perfect for the buyer that wants the charm of an older home but modern updates are a must. Relax on the charming front porcha''a perfect blend of comfort, style, and natural beauty.

The renovation of this 1930's Cape Cod by a master craftsman and his designer wife into the stunning modern day Contemporary it is today, while preserving some of the original highlights,is nothing short of a design miracle. The immense Great Room with the 60 foot wall of glass overlooking the terraced stone wall that leads to a stream and pine forest is the focal point of this special home. The exquisite chef's kitchen with 3 islands, marble counters, high end appliances with both a coffee and wine center is in full sight of the floor to ceiling fireplace, and numerous seating arrangements. From the built in sound system, to the central vac, full house generator, hydrotherapy massage tub in the primary suite, dual head shower and four fireplaces, or the waterfall in the

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

First-time for this treasured dwelling to be available for purchase. This magical setting surrounded by lush gardens and plantings is just the beginning of the enchantment. Distant mountain views to the east brings your viewscape to Butternut Ski & beyond. Inside the dwelling is a large open living space & kitchen on the first floor. Separately, there is a first-floor Ensuite. Abutting the first level, is a charming screened porch for dining or just taking in the sounds of nature. An open deck on the backside of the main level awaits your enjoyment. The 2nd level contains two VERY large bedrooms Ensuite; both with walk-in closets along with more locations for maximizing the distant views. The finished lower/walkout level has a full bath for a possible 4th Ensuite and living space