27

Homes for Sale in 01266

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  • /8

    $69,500

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 550 Sq Ft

    3 Jennifer Ln, West Stockbridge, MA 01266

    Nicely remodeled 2 bedroom trailer with fireplace and 2 baths. Park rent is $399.56 per month.

    Agent Photo

    John Ciepiela

    BISHOP WEST REAL ESTATE

    (413) 741-1606

    3 Jennifer Ln, West Stockbridge, MA 01266
  • /57

    $1,895,000

    • 6 Beds
    • 4.5 Baths
    • 4,139 Sq Ft

    176 W Center Rd, West Stockbridge, MA 01266

    A lovely, winding approach to this gorgeous 21-acre estate ensuring serenity, privacy, and the beauty of living in the country. The main house includes 3-4 bed, 2 1/2 bath. An impressive architect-designed guest house has 2 ensuite bedrooms with balconies, dramatic exposed beams and vaulted ceilings. The guest house is an extraordinary place to host family and friends both winter and summer. With

    Randy Thunfors STONE HOUSE PROPERTIES, LLC

    176 W Center Rd, West Stockbridge, MA 01266
  • /53

    $3,275,000

    $475K PRICE DROP
    • 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
  • /50

    $2,185,000

    • 3 Beds
    • 3.5 Baths
    • 4,752 Sq Ft

    14 Old Tree Farm Rd, Stockbridge, MA 01262

    A rare Berkshire offering w/ space, privacy, & exceptional versatility. Fabulous home & separate studio minutes from Tanglewood & Stockbridge Bowl. Charming 3 BR, 2.5 BA, 2,952 sq ft home - complemented by a beautifully renovated 1,800 sq ft studio barn w/ loft & full BA - rests on 8 picturesque acres with beautiful western views. Perfect for outdoor enthusiasts, culture lovers, or anyone seeking

    Claire Pollart WILLIAM RAVEIS - BERKSHIRE

    14 Old Tree Farm Rd, Stockbridge, MA 01262
  • /81

    $3,325,000

    • 4 Beds
    • 7.5 Baths
    • 6,000 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 wood burning 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. 4 private bedroom

    Sheila Thunfors STONE HOUSE PROPERTIES, LLC

    83 Maple Hill Rd, West Stockbridge, MA 01266
  • /50

    $2,750,000

    $245K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,932 Sq Ft

    10 Mahkeenac Shores Rd, Stockbridge, MA 01262

    Experience the best of Berkshire living in this stunning contemporary waterfront home on Stockbridge Bowl. Thoughtfully designed, this 4 BR, 3 full bath year 'round home offers a seamless blend of modern comfort and natural beauty! Sunlight pours through expansive windows, framing breathtaking water views from nearly every room. The open concept living space is anchored by a striking double sided

    Mary Jo Piretti PIRETTI REAL ESTATE

    10 Mahkeenac Shores Rd, Stockbridge, MA 01262
  • /41

    $3,850,000

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

    21A Interlaken Rd, Stockbridge, MA 01262

    A newly built modern country home of rare quality and quiet sophistication, set on five private acres in the heart of Stockbridge.Modern country living at its finest--crafted with exceptional quality, refined taste, and a true sense of warmth. Newly completed and never before lived in, this 4,000 sq ft residence sits on 5 private acres, just minutes to Lenox, downtown Stockbridge, and the Mass

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    21A Interlaken Rd, Stockbridge, MA 01262
  • /97

    $874,900

    • 5 Beds
    • 5.5 Baths
    • 3,241 Sq Ft

    4 Stockbridge Rd, West Stockbridge, MA 01266

    Nestled in the heart of West Stockbridge, this stunning 5-bedroom, 5.5-bath Federal/Greek Revival style home at 4 Stockbridge Road combines historic charm with modern luxury. Built in 1825, the residence has been beautifully renovated, maintaining its classic character while offering contemporary amenities. The spacious interior features generous living areas, perfect for family gatherings and

    Doug Collins Lamacchia Realty, Inc. - Dalton

    4 Stockbridge Rd, West Stockbridge, MA 01266
  • /52

    $1,625,000

    $50K PRICE DROP
    • 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
  • /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
  • /46

    $680,000

    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft

    7 Swamp, West Stockbridge, MA 01266

    Don't miss this rare opportunity to own this private, meticulously maintained waterfront sanctuary. The grounds feature a charming English garden, an expansive deck and a private dock for launching kayaks, offering outdoor living at its best. The main level features an eat-in kitchen with custom cabinetry, a living room, sunroom ideal for gatherings, an office, mudroom with laundry and a

    Molly Thomas COMPASS MASSACHUSETTS , LLC GB

    7 Swamp, West Stockbridge, MA 01266
  • /60

    $5,245,000

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

    50 East Rd, West Stockbridge, MA 01266

    Set on 35.6 acres in the heart of Alford, this exceptional estate offers privacy, sweeping western views to the Catskills,and direct access to the Tom Ball Mountain Trail, abutting hundreds of acres of protected land. Located just minutesfrom Great Barrington and approximately 10 minutes to the Massachusetts Turnpike, the property combines seclusionwith convenient access to the region's top

    Elyse Morris ELYSE HARNEY REAL ESTATE

    50 East Rd, West Stockbridge, MA 01266
  • /5

    $495,000

    • Land
    • 19 Acres
    • $26,053 per Acre

    0 Mohawk Lake Rd, Stockbridge, MA 01262

    Wonderful opportunity to own 19 acres in Stockbridge for your dream home! The parcel features acres of deciduous trees with an abundance of peacefulness and tranquility. Gentle upward slope from the street then levels off. Providing several options for building. Freestanding fireplace/chimney remains from a former homestead. Norman Rockwell Museum, Chesterwood and Berkshire Botanical Gardens down

    Debra Petrovsky DONOVAN REAL ESTATE

    0 Mohawk Lake Rd, Stockbridge, MA 01262
  • /18

    $315,000

    • Land
    • 10.52 Acres
    • $29,943 per Acre

    0 Lenox Rd Unit 249209, West Stockbridge, MA 01266

    A rare opportunity to own two lots totaling 10.6 acres in sought-after West Stockbridge. Accessed by a shared driveway, the parcels offer flexibility for a private compound or two thoughtfully sited homes. Mowed walking paths wind through groves of mature trees and the partially cleared landscape, creating a peaceful setting with a natural balance of privacy and usable space. The property

    Conor Meehan STONE HOUSE PROPERTIES, LLC

    0 Lenox Rd Unit 249209, West Stockbridge, MA 01266
  • /42

    $9,995,000

    $4M PRICE DROP
    • 7 Beds
    • 9 Baths
    • 10,429 Sq Ft

    30 East Rd, West Stockbridge, MA 01266

    Majestic Tudor Estate on over 71 Acres atop Tom Ball Mountain in the quaint hamlet of Alford, MA. Privacy and Breathtaking views from nearly every room. Formal Entry and Foyer. Stately Living Room and Dining Room. Comfortable Great Room with Gourmet Kitchen. Warm Den. Family Room, Gym and Massage Room. 5 en-suite Bedrooms in the Main House. Separate 2 Bedroom Guest House with beamed ceilings and

    Steven Weisz William Pitt Sotheby's International Realty

    30 East Rd, West Stockbridge, MA 01266
  • /28

    $299,000

    $50K PRICE DROP
    • 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
  • /29

    $1,295,000

    $300K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 2,835 Sq Ft

    130 East Rd, West Stockbridge, MA 01266

    Nestled in picturesque Alford, this inviting four-bedroom, 4.5-bath home blends comfort and flexibility in a serene Berkshire setting. The first-floor primary suite features a private ensuite bath, ideal for easy living. Thoughtfully designed spaces offer room for guests, work, or hobbies, while seasonal views bring natural beauty indoors throughout the year. With low Alford taxes and a peaceful

    Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    130 East Rd, West Stockbridge, MA 01266
  • /76

    $950,000

    $200K PRICE DROP
    • 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
  • /27

    $599,900

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft

    8 Lukeman Ln, Stockbridge, MA 01262

    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

    Jesse Dimitropolis RE/MAX COMPASS

    8 Lukeman Ln, Stockbridge, MA 01262
  • /22

    $799,000

    $50K PRICE DROP
    • Land
    • 29 Acres
    • $27,552 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
  • /5

    $289,000

    $26K PRICE DROP
    • Land
    • 14.74 Acres
    • $19,607 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
  • /30

    $752,000

    • 3 Beds
    • 1.5 Baths
    • 1,750 Sq Ft

    9 Interlaken Rd, Stockbridge, MA 01262

    Quitessential 1830's side hall Colonial....charming home located in the village of Interlaken in the town of Stockbridge, MA....just minutes to Lenox, Stockbridge center and the Berkshire Botanical Center. Listen to the babbeling water from the Larrywaug Brook and walk just steps to the small town park.....sit on the deck or around the firepit to soak in the atmosphere of privacy and

    Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    9 Interlaken Rd, Stockbridge, MA 01262
  • /16

    $295,000

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

    0 Glendale Rd Unit 248566, 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 248566, Stockbridge, MA 01262
  • /19

    $750,000

    • 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.Can also be purchased as part of a investment portfolio 13 Park Street Stockbridge, MA MLS#249532

    Matt Carlino MACCARO REAL ESTATE

    35 Main St, West Stockbridge, MA 01266
  • /32

    $765,000

    • 3 Beds
    • 2 Baths
    • 1,497 Sq Ft

    137 East Rd, West Stockbridge, MA 01266

    Tucked away on a bucolic country road, the only thing more enchanting than this mid-century gem is the magical property it calls home. Wrapped in the quintessential Alford setting, this inviting retreat offers all the amenities one seeks for relaxed country living. Surrounded by mature trees and timeless stone walls, the home exudes warmth & character with its cozy fireplace, front porch, rear

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    137 East Rd, West Stockbridge, MA 01266
  • /52

    $1,295,000

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

    45 Swamp, West Stockbridge, MA 01266

    Set across 30+ pristine Berkshire acres, this property offers sweeping westerly mountain views, gently rolling fields, and Cone Brook running the length of the land to Shaker Mill Pond. With approximately 2,000 feet of frontage on Swamp Road, the possibilities are wide open: farming, equestrian use, a private estate, or potential subdivision into 6+ buildable lots.Two substantial barns, both

    Paige Backhaus WILLIAM RAVEIS - BERKSHIRE

    45 Swamp, West Stockbridge, MA 01266
  • /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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