30

Homes for Sale in 01266

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  • /16

    $295,000

    • Land
    • 25.22 Acres
    • $11,697 per Acre

    0 Glendale Rd Unit 245211, Stockbridge, MA 01262

    Beautiful 25 Acres in Stockbridge. Stockbridge Bowl, Tanglewood, the villages of Stockbridge, Lenox, and Housatonic are all nearby. The property consists of two separate building lots - the south lot with 12.56 acres, and the north lot with 12.66 acres. Potential for mountain views from both lots with some clearing. Many possibilities - build on the north lot and keep the south lot for extra

    Sheila Thunfors STONE HOUSE PROPERTIES, LLC

    0 Glendale Rd Unit 245211, Stockbridge, MA 01262
  • /40

    $389,000

    • 3 Beds
    • 1 Bath
    • 1,269 Sq Ft

    26 Lenox Rd, West Stockbridge, MA 01266

    1900's cottage set above the village of West Stockbridge. Open plan living with updated kitchen and bath, with laundry tucked in below the stairs and second floor has three bedrooms. Fenced yard creating a nice private space with wraparound deck. Shed at the back of the property providing a lovely additional space.

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    26 Lenox Rd, West Stockbridge, MA 01266
  • /52

    $1,675,000

    • 12 Beds
    • 7 Baths
    • 8,881 Sq Ft

    29 Main St, West Stockbridge, MA 01266

    Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully

    Suzann Ward HOUSATONIC REAL ESTATE

    29 Main St, West Stockbridge, MA 01266
  • /3

    $975,000

    • Land
    • 131.69 Acres
    • $7,404 per Acre

    0 Lenox Rd Unit 246122, West Stockbridge, MA 01266

    This is a generous hillside parcel with a perc and potential views to the west. It is just over the hill from Stockbridge Bowl and Tanglewood, in an area of fine homes.

    Jim Stark L. J. STARK AND CO.

    0 Lenox Rd Unit 246122, West Stockbridge, MA 01266
  • /69

    $2,250,000

    • 4 Beds
    • 3.5 Baths
    • 4,445 Sq Ft

    50 Old Village Rd, Great Barrington, MA 01230

    Nestled beside 900 acres of Alford Springs Nature Preserve, this contemporary colonial is sited on 5.8 acres. Built in 2005 and fully renovated in 2021, it boasts high-efficiency HVAC and hot water, 14GW of seller-owned solar, an open main floor plan, gorgeous kitchen with top-of-the-line appliances, front porch, screened porch, large 2-car garage, and generously-sized rooms throughout. Two

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    50 Old Village Rd, Great Barrington, MA 01230
  • /14

    $250,000

    • Land
    • 1.98 Acres
    • $126,262 per Acre

    181 W Center Rd, West Stockbridge, MA 01266

    Lots of preparation work went into this building lot with a handsome meadow and dramatic ledge formations with large pockets of cool ferns. Some western views and a north east field stone wall. Almost 2 acres. Old well in place. Excellent percolation test results with 1 inch per min. Curb cut. Ready to build.

    Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    181 W Center Rd, West Stockbridge, MA 01266
  • /19

    $775,000

    • 8 Beds
    • 4 Baths
    • 3,192 Sq Ft

    35 Main St, West Stockbridge, MA 01266

    Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 &3 all in 2023.

    Matt Carlino MACCARO REAL ESTATE

    35 Main St, West Stockbridge, MA 01266
  • /53

    $3,750,000

    • 4 Beds
    • 3.5 Baths
    • 3,225 Sq Ft

    40 E Alford Rd, West Stockbridge, MA 01266

    Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living

    Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    40 E Alford Rd, West Stockbridge, MA 01266
  • /12

    $212,900

    • Land
    • 4 Acres
    • $53,225 per Acre

    0 Cross Rd, West Stockbridge, MA 01266

    Spectacular 4+/- acre parcel in a peaceful setting. It is backed up to a state conservatory so your privacy will remain in tact! This beautiful parcel is ready for your new home with a recent survey and perc test. Nestled in a tranquil area, that’s close to Card Pond and downtown Lenox. Come develop your dream home on this private parcel, but yet still be near all of the local attractions and

    Kimber Bradley Robin Delaney Real Estate

    0 Cross Rd, West Stockbridge, MA 01266
  • /95

    $13,500,000

    • 7 Beds
    • 9 Baths
    • 10,429 Sq Ft

    30 East Rd, West Stockbridge, MA 01266

    Majestic 71 acre Tudor Estate atop Tom Ball Mountain in the quaint hamlet of Alford, MA. Enjoy total privacy and breathtaking views from nearly every room. The main house features 5 en-suite bedrooms, a gourmet kitchen, formal living and dining rooms, den, family room, gym, billiard room and massage room. A separate 2-bedroom guest house offers beamed ceilings and full amenities. Manicured

    Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    30 East Rd, West Stockbridge, MA 01266
  • /56

    $1,395,000

    • 4 Beds
    • 2 Baths
    • 2,058 Sq Ft

    45 Swamp, West Stockbridge, MA 01266

    1950s retro home, rich with family history, situated on 30+ acres of land & offering expansive westerly views & gentle sloping fields. Pathways lead to Shaker Mill Pond & Cone Brook which run the entire length of the property. Interior features include 2 BRs, office & full bath on the main level, 2 BRs & full bath on the second floor, a quaint kitchen, & living room. Additionally, a fully heated

    Paige Paluch LANCE VERMEULEN RE, INC

    45 Swamp, West Stockbridge, MA 01266
  • /60

    $5,475,000

    • 5 Beds
    • 8 Baths
    • 9,400 Sq Ft

    Unlisted Address

    Nestled in the heart of Alford, Massachusetts, this extraordinary 35.6-acre Berkshire County estate offers unparalleled privacy with sweeping western Catskill Mountain views and direct access to conservation land. The impressive 9,400 sq ft main residence, built in 2003 and comprehensively updated beginning in 2020, features 4 bedrooms, 5 full baths, and resort-caliber amenities throughout its

    Elyse Morris ELYSE HARNEY REAL ESTATE

    Unlisted Address
  • /33

    $399,000

    • 3 Beds
    • 1.5 Baths
    • 1,677 Sq Ft

    20 Moscow Rd, West Stockbridge, MA 01266

    Short walk to quaint downtown West Stockbridge featuring local coffee shop, variety store, restaurants and shops. Just a few minutes to local theatres, music venues, Tanglewood, historic Stockbridge, and the Mass Pike. Beautiful open yard great for summer entertaining including cookouts, yard games or just relaxing and reading a book! Cozy fireplace for those beautiful snowy New England nights.

    Mark Harris SIGNATURE ASSOCIATES

    20 Moscow Rd, West Stockbridge, MA 01266
  • /19

    $550,000

    • 4 Beds
    • 3 Baths
    • 2,600 Sq Ft

    15 W Stockbridge, Stockbridge, MA 01262

    The ideal Berkshire escape can be yours. Prime location between historic Stockbridge & vibrant West Stockbridge, minutes to Tanglewood. This turnkey 4-bed, 3-bath home is a sanctuary of light where thoughtful upgrades ensure peace of mind. Key systems are new: a lifetime metal roof, 3 year old re-engineered and designed septic, high-efficiency Buderus boiler, and oversized windows that connect

    C. Ethan Watt WILLIAM PITT SOTHEBY'S - SALISBURY

    15 W Stockbridge, Stockbridge, MA 01262
  • /49

    $949,000

    • 1 Bed
    • 1.5 Baths
    • 3,810 Sq Ft

    30 Great Barrington Rd, West Stockbridge, MA 01266

    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

    Cortney Dupont COHEN & WHITE ASSOCIATES

    30 Great Barrington Rd, West Stockbridge, MA 01266
  • /76

    $950,000

    • 3 Beds
    • 4 Baths
    • 2,900 Sq Ft

    29 Old Village Rd, Great Barrington, MA 01230

    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

    Thomas Doyle, Sr. BISHOP WEST REAL ESTATE

    29 Old Village Rd, Great Barrington, MA 01230
  • /83

    $3,325,000

    • 5 Beds
    • 7.5 Baths
    • 7,957 Sq Ft

    83 Maple Hill Rd, West Stockbridge, MA 01266

    Hawks Nest Ridge. Quiet privacy on 8.6 acres. Decks, patio, screened porch and pool all enjoy the view and the natural setting. Dramatic open floor plan with walls of windows to the views, soaring stone fireplace spanning three stories. Cook's kitchen with walk-in pantry. First floor primary suite with gas fireplace and dressing room all abutting library and office. 5 private bedroom suites in

    Sheila Thunfors STONE HOUSE PROPERTIES, LLC

    83 Maple Hill Rd, West Stockbridge, MA 01266
  • /43

    $1,790,000

    • 5 Beds
    • 4.5 Baths
    • 6,000 Sq Ft

    248 East Rd, West Stockbridge, MA 01266

    A luxurious home on one of the most scenic roads in The Berkshires, surrounded by 15 pastoral acres, with picturesque mountain views. Enter a sun-drenched living room with a soaring cathedral ceiling and an elegant fireplace centerpiece. Enjoy an expansive 3-season porch, with panoramic windows and classic mahogany floors. A recently updated eat-in kitchen features Sub Zero appliances and a

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    248 East Rd, West Stockbridge, MA 01266
  • /22

    $824,000

    • Land
    • 29 Acres
    • $28,414 per Acre

    416 West Rd, Alford, MA 01266

    Experience the Berkshires Like Never BeforeNestled on West Road in Alford, this exceptional 29-acre estate offers a rare blend of natural beauty, flexibility, and investment potential. A meandering brook, Alford Brook gently courses through the property, creating serene waterside vistas and the soothing soundtrack of flowing water day and night.From the open meadows and wooded glens, enjoy

    Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    416 West Rd, Alford, MA 01266
  • /36

    $595,000

    • 3 Beds
    • 3 Baths
    • 2,476 Sq Ft

    4 Main St, West Stockbridge, MA 01266

    Beautiful two family riverside home offering comfort, flexibility, and in-town convenience. The front 2BR/2BA residence features soaring ceilings, skylights, an open kitchen, private riverfront deck, and an oversized ensuite bedroom. A spacious lower level provides room for guests, hobbies, or work. A charming garden area overlooking the Williams River adds outdoor enjoyment. The attached 1BR/1BA

    Conor Meehan STONE HOUSE PROPERTIES, LLC

    4 Main St, West Stockbridge, MA 01266
  • /60

    $2,185,000

    • 3 Beds
    • 2.5 Baths
    • 2,952 Sq Ft

    14 Old Tree Farm Rd, Stockbridge, MA 01262

    Set on a quiet country road w/ private driveway, this charming 3 BR, 2.5 BA home sits on 8 picturesque acres just minutes from Tanglewood, Stockbridge Bowl & the villages of Stockbridge, Lenox & West Stockbridge. Perfect for outdoor enthusiasts, culture lovers or anyone seeking a peaceful Berkshire retreat. The location offers hiking, yoga & wellness centers, boating, skiing, & convenient access

    Claire Pollart LANCE VERMEULEN RE, INC

    14 Old Tree Farm Rd, Stockbridge, MA 01262
  • /42

    $589,000

    • 3 Beds
    • 2 Baths
    • 1,842 Sq Ft

    16 Swamp Rd, West Stockbridge, MA 01266

    The George Tyler Homestead appears on West Stockbridge maps as early as 1855. This charming 3-bedroom cottage exudes warmth and character with plenty of original detail. The wood-paneled living room features a handsome brick hearth with beehive oven and beautifully aged pine floors. The L-shaped kitchen offers ample storage and opens to a formal dining room, where a large window overlooks the

    Vashti Poor LANCE VERMEULEN RE, INC

    16 Swamp Rd, West Stockbridge, MA 01266
  • /28

    $349,000

    • 4 Beds
    • 3 Baths
    • 2,276 Sq Ft

    44 Main St, West Stockbridge, MA 01266

    Discover the charm of downtown living in this Colonial home located in the heart of West Stockbridge. This home features four bedrooms, two full baths, kitchen, living room, dining room and a deck overlooking the river. In addition to the main living area the property also includes an in-law or studio apartment with it's own kitchen and bathroom. With a nice flat yard for outdoor activities,

    Molly Thomas COMPASS MASSACHUSETTS , LLC GB

    44 Main St, West Stockbridge, MA 01266
  • /46

    $680,000

    • 3 Beds
    • 2 Baths
    • 1,255 Sq Ft

    7 Stockbridge Rd, West Stockbridge, MA 01266

    The Amasa Spencer House, circa 1791, is a beautifully preserved gem for antique-home lovers. Tucked into a bucolic yet convenient setting in West Stockbridge, it offers the rare ability to stroll to shops, restaurants, hardware store, market, arts and entertainment, coffee shop and a bookstore in the charming village center. Thoughtfully detailed from top to bottom in vibrant Farrow & Ball

    Lauren Molk ELYSE HARNEY REAL ESTATE

    7 Stockbridge Rd, West Stockbridge, MA 01266
  • /49

    $780,000

    • 3 Beds
    • 2 Baths
    • 2,046 Sq Ft

    17 Iron Mine Rd, West Stockbridge, MA 01266

    Designed for country living and entertaining, the heart of the home centers around a sun-filled great room with vaulted ceilings, wood beams, and French doors leading to a private deck. The chic kitchen has marble counters, subway tile, stainless steel appliances, gas stove and a peninsula for prep and dining. The 1st-floor primary suite offers a walk-in closet, updated full bath and deck access.

    Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

    17 Iron Mine Rd, West Stockbridge, MA 01266
  • /3

    $315,000

    • Land
    • 14.74 Acres
    • $21,370 per Acre

    0 E Alford Rd, West Stockbridge, MA 01266

    Beautiful and pristine 14.7 acre lot, family owned since 1963. 3-4 acres are an open field; a former Christmas tree farm. Rear portion of property is largely wooded with a stream. This area of East Alford Road has many million dollar plus homes. Perfect lot to build your tranquil dream home. Lot was perc tested in 2007. 10 Minutes to the center of West Stockbridge, 15 minutes to Great

    Matt DeLucia William Pitt Sotheby's International Realty

    0 E Alford Rd, West Stockbridge, MA 01266
  • /35

    $3,650,000

    • 3 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    42 W Alford Rd, West Stockbridge, MA 01266

    MODERN LUXURY-NO UTILITY BILLS. A net zero home. Framed by sweeping walls of glass, nature itself becomes part of the design in this single-level modernist retreat. The seamless indoor-outdoor flow invites you to take in mountain views from every angle. Refined simplicity define the space, with sleek lines, a cohesive palette, and high-end finishes creating effortless sophistication. Created by

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    42 W Alford Rd, West Stockbridge, MA 01266
  • /47

    $585,000

    • 2 Beds
    • 2.5 Baths
    • 1,935 Sq Ft

    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262

    MOTIVATED SELLER! Beautiful Carriage Barn Unit located in the sought after White Pines. The main level has open common spaces that include a gracious great room with a wall of windows to let in the natural light, wet bar and wood burning fireplace. Generous dining room overlooking the picturesque sun porch with serene view and galley kitchen that is oversized with ample storage space and laundry

    Cortney Dupont COHEN & WHITE ASSOCIATES

    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
  • /43

    $3,850,000

    • 4 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    21A Interlaken Rd, Stockbridge, MA 01262

    Modern country living at its finest--crafted with exceptional quality, refined taste, and a true sense of warmth. A dramatic double-height entry and living room create a seamless dialogue with the surrounding landscape while offering the comfort of home. The main level features an open-concept kitchen, living, and dining area, anchored on one side by the primary suite and on the other by a

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    21A Interlaken Rd, Stockbridge, MA 01262
  • /2

    $289,000

    • Land
    • 3.69 Acres
    • $78,320 per Acre

    0 Interlaken Cross Rd, Stockbridge, MA 01262

    A pristine building lot in the heart of the Berkshires! Parcel B at Echo Valley is a 3.69-acre wooded, buildable lot offering a beautiful blank canvas for your dream home. Located off Interlaken Cross Road in Stockbridge, MA, this level parcel is easy to work with and provides excellent flexibility for siting your house, garage, and outdoor living spaces. Just minutes from Tanglewood, Stockbridge

    Lisa Berry Simply Sell Realty

    0 Interlaken Cross Rd, Stockbridge, MA 01262
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