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37 Photos
MACCARO REAL ESTATE
$579,000
3 BD | 2 BA
Residential - Single Family

Beautiful 3-bedroom, 2-bath ranch home offering an inviting layout, excellent flow, and plenty of room to spread out across 2,448 square feet. You'll never feel cramped in this spacious and comfortable home. The location is hard to beat--just minutes from downtown Lee and a short drive to downtown Lenox, yet tucked away on a peaceful country road. Enjoy scenic pastoral and mountain views while walking through the neighborhood, or step onto The Pinnacle, a town-owned hiking trail located just steps from your door. After a day of exploring, relax on the back deck and take in the tranquil country setting.


28 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$579,000
3 BD | 2 BA
Residential - Single Family

Charming Historic Gem in the Heart of Stockbridge Embrace classic New England living in this 3-bedroom, 2-bathroom home boasting 1,664 square feet of old-world charm, warmth, and character. Ideally located along East Main Street, this residence offers an unbeatable, walk-to-everything village lifestyle while maintaining a remarkably quiet, private sanctuary indoors and out. Inside, a bright and open floor plan is filled with natural light, highlighted by rich hardwood floors, exposed timber beams, and thoughtful architectural details. The inviting main level features a cozy living room, a dedicated library nook with built-in shelving, and a sunlit dining area wrapped in oversized glass panels.


55 Photos
413 REAL ESTATE
$579,900
3 BD | 3 BA
Residential - Single Family

Welcome home to this well-maintained 3-bedroom, 2.5-bath Cape offering 2,561 square feet of comfortable living space. The heart of the home is the kitchen and den area, featuring durable tile flooring and an open, inviting layout perfect for everyday living and entertaining. Sliding doors lead to a large screened porch overlooking the in-ground pool and beautifully sized backyard, creating an ideal setting for summer gatherings and outdoor relaxation. A formal living room with a cozy gas fireplace provides an elegant space for unwinding. The finished lower level offers additional flexible living space, perfect for home office, gym, or recreation area. Additional highlights include attached 2 car garage and ample storage. Enjoy indoor and outdoor living at its best in this attractive home.


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RE/MAX COMPASS
$579,900
3 BD | 2 BA
Residential - Single Family

This move-in ready, sunny Cape next to the Botanical Garden offers significant upgrades, a four-season sunroom, private fenced backyard, attached garage, patio, first-floor bedroom & full bath, and low Stockbridge taxes. Hardwood floors, updated kitchen with pantry, mini-splits for heat & AC, new roof, gutters, windows, insulation, primary bath, and electric hot water heater make this truly turnkey. Minutes to Norman Rockwell (3), Tanglewood (9), The Mount (13), Shakespeare & Co (13), Ski Butternut (17), downtown Stockbridge (5), Lenox (12), Great Barrington (16) & I-90 (13). Cozy, year-round retreat on a quiet street -- won't last long!


61 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$584,900
4 BD | 4 BA
Residential - Single Family

OPEN HOUSE CANCELLED! Experience the perfect blend of professional utility and luxurious comfort at 1 Almon Ave., a beautifully constructed and impeccably maintained retreat located in a BG-zoned area. This home offers an exceptional opportunity for those looking to operate a business or maintain a home-office setup without sacrificing lifestyle quality. The main residence provides four spacious bedrooms, including a convenient first-floor bedroom w/ a walk-in closet, complemented by four full bathrooms. At the heart of the home, the gourmet kitchen showcases custom hickory cabinetry paired with solid granite countertops. The second floor--which, along with the stairs, will feature new carpet--includes three additional bedrooms, a family room, a full bath with laundry, and a


3 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$585,000
4 BD | 3 BA
Residential - Single Family

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.


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WILLIAM RAVEIS - BERKSHIRE
$585,000
3 BD | 2 BA
Residential - Single Family

Welcome to this inviting Lindal Cedar home, nestled in the sought-after Otis Wood Lands community. The open-concept kitchen, living & dining area features a soaring cathedral ceiling, a wall of windows with serene wooded views & easy access to the cedar deck--perfect for relaxing or entertaining. Lovely screened-in porch offers additional space to enjoy the peaceful setting. The main level includes 2 comfortable BRs & full bath. Upstairs, a spacious loft area leads to the primary suite. Unfinished, walk-out lower level, with radiant heat, provides excellent potential for an office, rec room, or additional living space. Enjoy the many amenities of Otis Wood Lands, including pool, tennis/pickleball courts, fitness room, lodge, playground, Owl Lake for non-motorized watercraft, & beach area.


52 Photos
COMPASS MASSACHUSETTS , LLC GB
$585,000
3 BD | 3 BA
Residential - Single Family


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ALTON & WESTALL REAL ESTATE AGENCY, LLC

An extraordinary opportunity to create a truly exceptional Berkshire estate. Set along a quiet country road in Williamstown, this stunning 17-acre parcel offers a rare combination of sweeping views, privacy and the natural beauty of the Berkshires. Surrounded by picturesque countryside, the expansive acreage provides an exceptional canvas for a private residence, country retreat or weekend escape. Imagine designing your dream home to embrace the breathtaking views and serene landscape while enjoying the peace and seclusion of this remarkable setting. Ideally located just minutes from Williams College, the Clark Art Institute, and the charming shops, restaurants, and cultural offerings of downtown Williamstown.


34 Photos
HOUSATONIC REAL ESTATE
$589,000
4 BD | 4 BA
Multi-Family


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HOUSATONIC REAL ESTATE

Welcome to a rare opportunity to own or rent a thriving commercial business that has been family owned and operated since 1966. This unique property offers a range of possibilities, including a full-service auto garage, an auto shop with a two-bay garage, and two separate apartments for rental opportunities. With ample storage for up to six cars and additional parking, this property is a dream come true for entrepreneurs and investors alike. As you step onto the premises, you are immediately greeted by a sense of history and longevity. For over half a century, this gas station and auto service center has been a trusted resource for the local community.


35 Photos
WOLCOTT REALTY
$589,000
3 BD | 1 BA
Residential - Single Family

Escape to your own island retreat where each day is a peaceful, waterfront sojourn. Nestled on an island in Big Pond, this tranquil waterfront property offers extraordinary privacy, natural beauty and modern comfort. Thoughtfully updated, the home features a masterfully renovated kitchen and bath, a first-floor bedroom and distinctive architectural details including cedar shakes, that create warmth and character throughout. All furnishings to stay. Mornings of seasonal birdsong and the delicate beauty of the new day invite ease and comfort both on the screened, full-windowed porch or on the two outdoor decks. Breathtaking views of the lake encourage leisurely relaxation while winding garden paths and natural stone walls enhance the property's timeless appeal


30 Photos
HARSCH ASSOCIATES

This remarkable investment opportunity in the heart of the historic town of Bennington offers the future owner two beautifully and totally updated and restored historic 19th century buildings with plenty of style, character, and multiple options. The prominent North St. location stands out to the 8,000-12,000 daily traffic count passing by assuring outstanding visibility. Continue leasing to the existing business or locate a new business or professional office here while also receiving the income from the leased building next door housing a locally famous deli. 125 North St. contains 2,225 SF on two floors plus attic and full basement, all renovated in 2001. Also completely renovated in 2001, 100 Pleasant St. contains 1,500 SF on two floors.


30 Photos
BIRCH PROPERTIES
$590,000
1 BD | 2 BA
Residential - Condo/Townhouse

There is something wonderfully easy about Loft 209. Soft north light, restored wood floors, exposed brick and original mill columns give this 1,345 SF one-bedroom + study residence its character, while a thoughtful layout makes it exceptionally comfortable to actually live in. Conceived by celebrated architects LATENT Productions, Greylock WORKS reflects an uncommon respect for the historic mill, its architecture and its Berkshire setting. Original materials and industrial details have been preserved and celebrated, while highly custom modern interventions bring a quiet timelessness to the spaces. The result has a genuine sense of place--architecture that could only belong here.


32 Photos
SIGNATURE ASSOCIATES
$594,900
4 BD | 3 BA
Residential - Single Family

Welcome to 4 Filomena Drive, where comfort meets the natural beauty of the Berkshires! Tucked away in a peaceful Southeast Pittsfield neighborhood, this inviting home offers a wonderful connection to the outdoors. Enjoy the tranquil backyard, bordered by a year round brook and beautiful views of the surrounding natural landscape. Whether you are grilling on the deck, entertaining on the patio, or simply enjoying the sights and sounds of nature, this property offers a perfect place to unwind. Inside, you'll find welcoming living spaces, an enormous finished basement, and plenty of room to make yourself at home. Enjoy the serenity of your own backyard retreat while staying just minutes from all the Berkshires has to offer!


31 Photos
HOUSATONIC REAL ESTATE
$595,000
4 BD | 3 BA
Residential - Single Family

IMMACULATE 3 BEDROOM COLONIAL with ONE BEDROOM 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.


31 Photos
HOUSATONIC REAL ESTATE
$595,000
4 BD | 3 BA
Multi-Family

IMMACULATE 3 BEDROOM APARTMENT WITH DECK and ONE BEDROOM APARTMENT in SOUTH LEE on a quiet cul de sac. Zoned 2 family, partially fenced back yard, attached garage, CENTRAL AIR CONDITIONING - BRAND NEW VINYL SIDING DECEMBER 2025.


30 Photos
HOUSATONIC REAL ESTATE
$595,000
2 BD | 2 BA
Residential - Single Family

El Refugio, ''The Refuge'', a hidden gem minutes from downtown Great Barrington. A 2-bedroom, 2-bath, wood burning fireplace home - with a 46' heated pool and 2-car detached garage. Set back from the road on 7+ private acres with extensive shoreline on the Williams River.


44 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$595,000
3 BD | 2 BA
Residential - Single Family

Situated on highly desirable Mountain Drive, this expanded 3-bedroom, 2-bath Cape delivers classic Berkshire charm, thoughtful updates, and flexible living spaces. Step inside from the welcoming front porch into an inviting layout featuring hardwood floors and abundant natural light. The spacious living room is anchored by a wood-burning fireplace flanked by custom built-ins, flowing into the formal dining room and a tastefully remodeled kitchen. Enjoy year-round tranquility in the heated four-season sunroom or relax in the separate main-floor den featuring a cozy gas fireplace and sliders leading out to the rear deck. A generous first-floor bedroom, full bath, and dedicated laundry room offer effortless single-level living convenience.


32 Photos
BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$595,000
3 BD | 2 BA
Residential - Single Family

Nestled on a peaceful street, this inviting 3 bedroom, 1.5 bath home offers the perfect blend of comfort and convenience. Step inside to find a bright and welcoming living space filled with natural light, a cozy dining area, and a functional kitchen ready for your personal touch. The three bedrooms provide plenty of room for family, guests, or a home office, while the updated half bath adds extra convenience. Enjoy morning coffee on the front porch or unwind in the private backyard--ideal for relaxing or entertaining. With sidewalks leading straight to town, you'll love being just a short stroll from shops and restaurants, all while enjoying the tranquility of a quiet neighborhood setting. Move-in ready and full of charm, this home offers small-town living at its best.

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