589

Berkshires, MA Homes for Sale with Acreage

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  • /31

    $995,000

    • 2 Beds
    • 2 Baths
    • 1,620 Sq Ft

    18 Creamery Rd, Great Barrington, MA 01230

    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

    Allison Rada STONE HOUSE PROPERTIES, LLC

    18 Creamery Rd, Great Barrington, MA 01230
  • /27

    $630,000

    • 4 Beds
    • 3 Baths
    • 1,950 Sq Ft

    245 Clubhouse Dr, Otis, MA 01253

    Fantastic 4 BR Otis Wood Lands Contemporary situated at the end of a cul-de-sac close to all community amenities! This spacious home has great spaces for family and friends. Price includes furniture. Community amenities include pool, tennis/pickleball courts, fitness room, playground, lodge, lake and beach. New septic in 2023, new hot water heater 06/2025, new roof 2003. $4,000 reserve fund

    Emily Piacquadio LANCE VERMEULEN RE, INC

    245 Clubhouse Dr, Otis, MA 01253
  • /6

    $152,999

    • Land
    • 6 Acres
    • $26,842 per Acre

    8 Brook Ln, Monterey, MA 01245

    Nestled in the heart of the Berkshires, this 5.7-acre wooded lot offers privacy, tranquility, and endless potential. With no HOA restrictions, this oversized parcel is ideal for your dream getaway or year-round retreat. Located directly across from Lake Buel and just a 5-minute drive to Butternut Ski Resort, it's a prime spot for both winter sports lovers and summer lakegoers. Enjoy the best of

    Steven Bintz PlatLabs, LLC

    8 Brook Ln, Monterey, MA 01245
  • /14

    $575,000

    • 1,708 Sq Ft

    292 E Hawley Rd, Charlemont, MA 01339

    Set on 77 acres, this exceptional property features the shell of an antique Cape, offering a blank canvas for your vision. It includes septic design, well, new electrical panel and architect-designed plans for a beautiful 2,360 sq ft home with 4 bedrooms, 2.5 baths, and 2-car garage. The land is a captivating mix of open fields and woods, with approximately 15-20 acres of sweeping meadows framed

    Wanda Mooney COLDWELL BANKER COMMUNITY REALTORS

    292 E Hawley Rd, Charlemont, MA 01339
  • /24

    $569,000

    • 5 Beds
    • 3.5 Baths
    • 3,307 Sq Ft

    867 Notch Rd, Cheshire, MA 01225

    A charming, spacious Colonial with privacy, and lovely grounds. Breathtaking mountain views. Built in 2005 and set on 7.25 acres, this 5-bedroom, 4.5-bathroom residence offers 3,307 square feet of living space. Two primary suites, one up and one down. The open-concept kitchen flows seamlessly into a great room, perfect for entertaining. This home does need work but is priced accordingly. Make

    Marnie Garzone THE KINDERHOOK GROUP - PITTSFIELD

    867 Notch Rd, Cheshire, MA 01225
  • /40

    $650,000

    • 4 Beds
    • 3 Baths
    • 2,548 Sq Ft

    93 Colrain Stage Rd, Charlemont, MA 01339

    Discover the enchanting allure of country living in this beautifully renovated and spacious home, nestled in the tranquil town of Heath. Set on an impressive 131 protected acres, with land on both sides of the street, this property is a paradise for outdoor enthusiasts. Imagine hosting unforgettable gatherings in the expansive kitchen and dining area, or unwinding beside the stunning fireplace in

    Herb Butzke William Pitt Sotheby's International Realty

    93 Colrain Stage Rd, Charlemont, MA 01339
  • /63

    $995,000

    • 3 Beds
    • 2.5 Baths
    • 3,292 Sq Ft

    2017 Monterey Rd, Otis, MA 01253

    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

    Katie Soules WILLIAM RAVEIS REAL ESTATE

    2017 Monterey Rd, Otis, MA 01253
  • /5

    $15,999

    • Land
    • 2.15 Acres
    • $7,441 per Acre

    8 William Holmes Rd, Becket, MA 01223

    Please note- seller has lowered the price several times and are now firm at the asking price. Nestled in the Deerhaven community, this 2.15-acre oversized wooded lot offers the perfect opportunity for those seeking privacy and seclusion in a serene natural setting. Ideally located just minutes from cultural landmarks like Jacob's Pillow and Tanglewood, and close to all the outdoor recreation and

    Steven Bintz PlatLabs, LLC

    8 William Holmes Rd, Becket, MA 01223
  • /40

    $575,000

    • 3 Beds
    • 3 Baths
    • 2,032 Sq Ft

    308 Hidden Ln, Sandisfield, MA 01255

    GORGEOUS STREAM FRONT LOCATION. Well maintained 3BR/3B home in popular Otis Wood Lands offering a private lake & beach, heated gunnite, olympic size pool, tennis & pickleball courts, clubhouse & fitness center. Very private setting overlooking a beautiful rushing stream, yet a short walk to all club amenities. Remodeled kitchen, AC, two screened porches, updated bath, over-size 2 car garage, hot

    Jeff Wilkinson Jeff Wilkinson

    308 Hidden Ln, Sandisfield, MA 01255
  • /27

    $500,000

    • 3 Beds
    • 1 Bath
    • 2,148 Sq Ft

    609 Berkshire Trail, Cummington, MA 01026

    Fantastic Opportunity on Busy Route 9! Full of charm and character, this colonial home offers tons of potential and plenty of space. Inside, you'll find a generous living room, a spacious eat-in kitchen, three bedrooms, and a full bath—perfect for comfortable everyday living. Attached to the home is a large bonus space with both interior and exterior access. Once a quaint store and bakery, it's

    Liz Helliwell 5 College REALTORS® Northampton

    609 Berkshire Trail, Cummington, MA 01026
  • /34

    $395,000

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    66 Reil Ln, Colrain, MA 01340

    Attention outdoor enthusiasts, this is the ultimate retreat you've been waiting for! Tucked away in a peaceful and private setting, this 122-acre property features a babbling brook, streams and meandering trails providing endless opportunities to explore and enjoy nature. Whether you're seeking solitude or adventure, this serene escape offers the perfect balance. The rustic Cape-style home, while

    Wanda Mooney Coldwell Banker Community REALTORS®

    66 Reil Ln, Colrain, MA 01340
  • /64

    $1,900,000

    • 5 Beds
    • 4.5 Baths
    • 4,500 Sq Ft

    355 Adsit Crosby Rd, New Marlborough, MA 01230

    Stunning contemporary nestled in tranquility. The main level boasts a gracious great room with cathedral ceilings, fireplace and walls of windows that wash the common spaces with natural light and bring nature in. Gourmet chefs kitchen with ample storage and dining room with direct access to the oversized porch that features a gas stove for the chillier days. First floor primary en suite with

    Cortney Dupont COHEN & WHITE ASSOCIATES

    355 Adsit Crosby Rd, New Marlborough, MA 01230
  • /49

    $949,000 Open Sun 11AM - 12:30PM

    • 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
  • /5

    $84,000

    • Land
    • 9 Acres
    • $9,261 per Acre

    Lot 15 Colebrook River Rd, Tolland, MA 01034

    Beautiful 9.07-acre lot in the foothills of the Berkshires, perfect for your dream home or getaway. Perc tested and ready to build. Enjoy the peace and natural beauty of quiet Tolland, MA.

    Stephanie Widun Nexthome Elite Realty

    Lot 15 Colebrook River Rd, Tolland, MA 01034
  • /42

    $499,000

    • 3 Beds
    • 3 Baths
    • 1,708 Sq Ft

    531 Old Rd N, Worthington, MA 01098

    Fabulous three-bedroom, three, full bath home with an open floor plan in pristine move-in condition. A totally updated, Turn-key property with hardwood floors throughout. Newer kitchen with quality cabinets, quartz countertops and tile floors. There is plenty of room on the main level with two full baths and three bedrooms. The main bedroom has an ensuite full bath and walk-in closet. The

    James Adams Hilltown Real Estate by Adams Realty

    531 Old Rd N, Worthington, MA 01098
  • /15

    $160,000

    • Land
    • 28 Acres
    • $5,680 per Acre

    0 Maxwell Rd Unit 246884, Charlemont, MA 01339

    Build, explore, or earn on this 25-acre sanctuary in Charlemont. Nestled between conservation lands with no visible neighbors, this expansive property includes two lots (12B & 12C), held in an LLC for streamlined sale. A freshwater stream winds through lush woods, while logging trails and a hand-built hunter's cabin make it ideal for recreation, hunting, or glamping. Income is already flowing via

    Justin Washburn MORESI REAL ESTATE PARTNERS

    0 Maxwell Rd Unit 246884, Charlemont, MA 01339
  • /23

    $523,995

    • Land
    • 10 Acres
    • $52,279 per Acre

    0 Swamp Rd, Richmond, MA 01254

    This 10-acre parcel in scenic Richmond, available for the first time in generations, offers a rare chance to build your dream home in the heart of the Berkshires. Surrounded by open farmland and natural beauty, this property provides a peaceful and inspiring setting for a country retreat or a year-round residence. The land features gently rolling meadows filled with wildflowers and native

    Conor Meehan STONE HOUSE PROPERTIES, LLC

    0 Swamp Rd, Richmond, MA 01254
  • /9

    $59,000

    • 4 Beds
    • 1.5 Baths
    • 2,244 Sq Ft

    477 Mohawk Trail, Drury, MA 01343

    Nestled along the scenic Mohawk Trail in Drury, MA, this 3.5-acre parcel offers a unique opportunity to build your dream home or getaway retreat in the heart of the Berkshires. While the existing structure is likely a teardown, the land itself boasts natural beauty, privacy, & convenient road frontage. Just minutes from Savoy Mountain State Forest, Mohawk Trail State Forest, and the Western

    Laiken Rapisarda LAMACCHIA REALTY, INC

    477 Mohawk Trail, Drury, MA 01343
  • /20

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,449 Sq Ft

    841 Moberg Rd, Becket, MA 01223

    Charming 3BR/2B home in popular Indian Lake Estates. Sunny great room and expansive decks welcome you to this cozy home. Screened porch for al fresco dining and a Vermont Castings wood stove for toasty winter get-togethers. Community offers two (non-motorboat) lakes with beaches and tennis courts. Excellent location with easy access to Jacob's Pillow Dance Festival, Tanglewood and most other

    Jeff Wilkinson STONE HOUSE PROPERTIES, LLC

    841 Moberg Rd, Becket, MA 01223
  • /38

    $414,500

    • 2 Beds
    • 2 Baths
    • 1,350 Sq Ft

    265 Fox Den Rd, Granville, MA 01034

    Beautiful, well maintained, sunny, airy home in coveted private lake community of Wildwood, nestled in the foothills of the Berkshires. Updated, open floor plan, year-round home with propane furnace and fireplace, walk to 1 of 5 sandy beaches with bath houses. New 3 Bedr septic installed 2019. Large 1.13 acre lot(s), provides room for much family fun and entertaining. Vaulted ceiling and many

    Joan Maxson Park Square Realty

    265 Fox Den Rd, Granville, MA 01034
  • /6

    $150,000

    • Land
    • 4.10 Acres
    • $36,585 per Acre

    37 N Farms Rd, West Whately, MA 01039

    Set in the quiet town of Williamsburg, this 4-acre parcel offers a peaceful setting and is only 10 minutes from Northampton and I-91. The location provides a nice balance of rural charm and convenience, with easy access to local conservation trails and a nearby bike path. The lot has a completed perc test and is well-suited for a single-family home. Whether you're looking to build now or planning

    Liz Helliwell 5 College REALTORS® Northampton

    37 N Farms Rd, West Whately, MA 01039
  • /44

    $1,600,000

    • 9 Beds
    • 4.5 Baths
    • 8,406 Sq Ft

    2049 S Undermountain Rd, Sheffield, MA 01257

    An exceptional opportunity awaits on 11 private acres in Sheffield. This unique property, currently utilized as a functional therapy facility, offers a massive footprint and a flexible canvas for your next venture. The centerpiece is an 8,000+ sq. ft. building comprised of over 10 offices, multiple conference rooms, common areas, and three residential apartments, creating an ideal setup for a

    Tony Segalla LANCE VERMEULEN RE, INC

    2049 S Undermountain Rd, Sheffield, MA 01257
  • /58

    $435,000 Open Sun 10AM - 12PM

    • 3 Beds
    • 1.5 Baths
    • 1,632 Sq Ft

    1689 E Windsor Rd, Windsor, MA 01270

    A rare find: 3 Bedroom colonial home with a picturesque pond for endless enjoyment. Dining under the stars in your private backyard oasis and waking up to breathtaking views and gentle melodies of nature. Discover the magic where memories are waiting to be made. Anderson windows and doors. A brick chimney with a wood stove adds seasonal warmth to the living room. The back porch entices you to

    Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

    1689 E Windsor Rd, Windsor, MA 01270
  • /53

    $997,000

    • 8 Beds
    • 6 Baths
    • 6,460 Sq Ft

    138 Ridge Rd, Worthington, MA 01098

    LOOKING FOR A COUNTRY ESTATE IN THE FOOTHILLS OF THE BERKSHIRES? This spectacular 6,460 sf custom built Colonial home has just been completed and has additional unfinished space over the attached 5 car garage, perfect for car enthusiasts! This spectacular property is set on nearly 9 picturesque acres w/possible additional building lot and sits beside the Worthington Golf Club! Quality throughout

    Jennifer Wilson BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

    138 Ridge Rd, Worthington, MA 01098
  • /10

    $100,000

    • Land
    • 2.44 Acres
    • $40,984 per Acre

    0 Pleasant St, Conway, MA 01341

    Terrific opportunity to build a smaller home on the upper side of an idyllic 2+acre field in the center of Conway. If you are looking for a traditional village setting, with space for gardens/animals, this spot could be the one! The entire parcel is open with a gentle slope to the Northwest. Wetter areas are along Maple street and at the lower end. Come take a look. It's not often that a parcel

    Sarah Newman Coldwell Banker Community REALTORS®

    0 Pleasant St, Conway, MA 01341
  • /9

    $215,000

    • Land
    • 32 Acres
    • $6,660 per Acre

    1282 Burt Hill Rd, Tolland, MA 01034

    Your chance to own 32.28 acres in Tolland, MA. Already subdivided into two approved lots (approx. 16 & 15 acres). Perc tests and septic design are complete. Private well and septic needed. Partially cleared with a crescent driveway layout cut in; trees are marked to guide your build. A brook runs along the back, offering a serene natural setting. Located in a quiet hilltown known for its natural

    Patricia Molina CENTURY 21 NORTHEAST

    1282 Burt Hill Rd, Tolland, MA 01034
  • /42

    $925,000

    • 4 Beds
    • 2 Baths
    • 4,105 Sq Ft

    1 Buffington Hill Rd, Worthington, MA 01098

    The Jonathan Woodbridge House, built in 1806, exhibits the classic hallmarks of Federal Georgian design: elegant proportions, symmetry and magnificent carved Palladian details. The eleven gracious rooms retain original Georgian details and moldings and include four bedrooms, two parlors, a library, two grand hallways, six fireplaces, and two baths. Few structures in the Berkshires possess this

    James Adams Hilltown Real Estate by Adams Realty

    1 Buffington Hill Rd, Worthington, MA 01098
  • /54

    $1,300,000

    • 4 Beds
    • 2.5 Baths
    • 2,180 Sq Ft

    119 Hayes Pond Rd, Otis, MA 01253

    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

    Tony Segalla LANCE VERMEULEN RE, INC

    119 Hayes Pond Rd, Otis, MA 01253
  • /29

    $912,000

    • 4 Beds
    • 4 Baths
    • 2,280 Sq Ft

    21 East St, Stockbridge, MA 01262

    **Price Improvement** Nestled in the heart of the Berkshires, this spaciously built 2003 Colonial sits on over 14 acres, offering privacy, potential, and long-term value. Currently operating as a doggy day care, but you wouldn't know it when you walk inside! Well-maintained & cared for. Recent updates include the kitchen, bathrooms, carpets, back deck, and front landscaping, while still leaving

    Brianna Boffoli Cameron Prestige, LLC

    21 East St, Stockbridge, MA 01262
  • /32

    $575,000

    • 3 Beds
    • 2.5 Baths
    • 1,603 Sq Ft

    289 Algerie Rd, Becket, MA 01223

    Let's imagine extreme privacy for a moment, yet your loved ones are simply a three minute walk away or a quick drive; because each one has their own home! With connecting roads this home is 1 of 3. This home has a hot tub and an impressive 4 garage bays for winter parking or car storage. A parcel on Indian lakes is also an attractive feature that is available. This will give you access to the

    Cristian Sanchez COHEN & WHITE ASSOCIATES

    289 Algerie Rd, Becket, MA 01223
  • /39

    $500,000

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    235 Algerie Rd, Becket, MA 01223

    Let's imagine extreme privacy for a moment, yet your loved ones are simply a three minute walk away or a quick drive; because each one has their own home! With connecting roads this home is 1 of 3. This home has a hot tub, 3 fireplaces and a garage for winter parking. A parcel on Indian lakes is also an attractive feature that is available. This will give you access to the tennis court and the

    Cristian Sanchez COHEN & WHITE ASSOCIATES

    235 Algerie Rd, Becket, MA 01223
  • /38

    $299,999

    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    192 Curran Rd, Cheshire, MA 01225

    Artful Country Retreat! Prime Berkshire Location. Tucked away on a quiet country road in Cheshire, this turnkey 3-bedroom, 1.5-bath home offers peace, privacy, & a deep connection to nature-yet it's just a short drive to both North & South County amenities. Set on nearly 2 acres of parklike grounds featuring meandering trails, woods, perennial flowers & berry bushes, grapes & a young pear &

    Dennis D'Arcangelo MONARCH REALTY, INC.

    192 Curran Rd, Cheshire, MA 01225
  • /32

    $1,250,000

    • 5 Beds
    • 5.5 Baths
    • 4,645 Sq Ft

    7 Perry Rd, Sandisfield, MA 01255

    WHERE EVERY SEASON FEELS LIKE HOME16 acres at the end of a quiet country road where your shoulders drop the moment you arrive. This five bedroom retreat with over 4,600 square feet gets Berkshire living right: soaring great room with fireplace, granite kitchen, four-season sunroom, and that incredible finished lower level with radiant floors, full bar, and walkout to covered patio. Mudroom with

    Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    7 Perry Rd, Sandisfield, MA 01255
  • /62

    $499,000

    • 4 Beds
    • 3 Baths
    • 1,188 Sq Ft

    377 Highland Way, Sandisfield, MA 01255

    Welcome to your dream getaway in Otis Woodlands, one of the Berkshires' premiere private communities. This beautiful home offers the perfect blend of rustic elegance and modern comfort, ideal for year-round living or a serene weekend escape.Nestled among the trees, this spacious 4-bedroom, 3-bathroom home features a dramatic great room with vaulted ceilings and exposed beams, complemented by a

    Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

    377 Highland Way, Sandisfield, MA 01255
  • /43

    $595,000

    • 3 Beds
    • 2 Baths
    • 2,500 Sq Ft

    214 Mohawk Trail, Florida, MA 01247

    Berkshire County log home on 10 acres affording big sky views. Gaze at Mt Greylock State Reservation from one of your four outdoor gathering spaces including the hot tub or rustic fire pit steps from the 760+ ft of unfinished space in the walkout lower level. Multiple heat pumps for your heating and cooling needs with a back up propane fired hot water boiler heating system ready to be connected.

    Jeffrey Loholdt WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    214 Mohawk Trail, Florida, MA 01247
  • /28

    $395,000

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft

    127 County Rd, Rowe, MA 01367

    Discover your oasis in the idyllic town of Rowe, where serenity meets modern living! This beautifully renovated ranch home, set on 1.17 acres, offers the perfect blend of comfort and efficiency. With a thoughtfully designed open floor plan, you'll enjoy a seamless one-floor lifestyle that includes a spacious, sunlit living room and a stunning remodeled kitchen. Step outside to your expansive

    Herb Butzke WILLIAM PITT SOTHEBY'S - LENOX

    127 County Rd, Rowe, MA 01367
  • /65

    $1,300,000

    • 2 Beds
    • 2.5 Baths
    • 2,270 Sq Ft

    200 Easthampton Rd, Westhampton, MA 01027

    Welcome to Starwind Farm, an extraordinary equestrian retreat set on 15.6 stunning acres, bordered by the North Branch of the Manhan River. A dream property for the discriminating horse enthusiast, this 2006 ranch home combines comfort, & functionality in a picturesque country setting. The home's open floor plan features 2 impressive fieldstone fireplaces, a primary en-suite, with direct access

    Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

    200 Easthampton Rd, Westhampton, MA 01027
  • /4

    $95,000

    • Land
    • 8 Acres
    • $11,296 per Acre

    39 Bow St, Plainfield, MA 01070

    Explore this prime vacant lot located in Plainfield, Massachusetts. Nestled in a serene neighborhood, this property offers an expansive buildable land parcel, ideal for your creative desires and needs. Covering a generous lot, this property offers frontage on a public road, ample outdoor space and several site options. The dimension and layout of the land are ideal for both construction and

    Ryan Brown Naples Realty Group

    39 Bow St, Plainfield, MA 01070
  • /4

    $669,000

    • 4 Beds
    • 3.5 Baths
    • 1,908 Sq Ft

    510 Main Rd, Chesterfield, MA 01012

    Incredible opportunity to personalize a nearly new construction! This home is undergoing a complete transformation—only the original first-floor framing remains. A full second-floor addition and full interior rebuild are in progress. Now framed with rough plumbing and electrical underway, this is the ideal time for a buyer to select finishes and add personal style. The second floor will feature a

    Daniel James Piasecki Coldwell Banker Community REALTORS®

    510 Main Rd, Chesterfield, MA 01012
  • /41

    $498,000

    • 3 Beds
    • 2 Baths
    • 1,504 Sq Ft

    132 Sandisfield Rd, Sandisfield, MA 01255

    This Greek Revival farmhouse in quaint Sandisfield blends historic charm with modern updates. The open-concept living/dining area features a bright sitting room w/ vaulted ceilings and french doors overlooking lush greenery in the peaceful backyard. The modern kitchen has marble countertops & new appliances. The largest bedroom and a full bath are on the first floor, along with laundry and ample

    Kate Lascar COMPASS MASSACHUSETTS , LLC GB

    132 Sandisfield Rd, Sandisfield, MA 01255

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