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Homes for Sale near John Dewey Academy

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  • /11

    $425,000

    • Land
    • 2 Acres
    • $212,500 per Acre

    11 Rowe Rd, Great Barrington, MA 01230

    Privacy and big potential! Build your Berkshire dream home in the quiet Alford hills on this 2 acre parcel surrounded by trees. Foundation for a new home is already built with architectural plans included as an added bonus. The property includes a new septic system and well, plus 1 outbuilding and additional barn at the back of the property.

    John Segalla HOUSATONIC REAL ESTATE

    11 Rowe Rd, Great Barrington, MA 01230
  • /32

    $795,000

    • 3 Beds
    • 2 Baths
    • 2,460 Sq Ft

    85 Main Rd, Monterey, MA 01245

    OUTSTANDING COUNTY LIVING in idyllic Monterey with its low real estate taxes and easy access to Lake Garfield and Lake Buel. Butternut Ski Area is only 5 minutes away. 8 minutes to downtown Great Barrington. This Timber Fame (open floor plan) contemporary home features beautiful (wide-plank) pinewood floors, a cathedral ceiling Great Room, and a bonus sleeping loft area. A fireplace on the

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    85 Main Rd, Monterey, MA 01245
  • /13

    $275,000

    • Land
    • 2.1 Acres
    • $130,952 per Acre

    14 Blue Hill Rd, Monterey, MA 01245

    A 2400 sq. ft. barn in Monterey ready for residential conversion. The property has a completed, successful perc test and established access to a shared well. The project is ready for immediate architectural planning. This is a prime opportunity for a buyer looking to fast-track construction on a desirable Berkshire lot.

    Tony Segalla LANCE VERMEULEN RE, INC

    14 Blue Hill Rd, Monterey, MA 01245
  • /6

    $265,000

    • Land
    • 1.97 Acres
    • $134,518 per Acre

    14 McGee Rd, Egremont, MA 01230

    Lovely building lot on a quiet road in bucolic Egremont. Well has been drilled, septic design done for two structures and power is brought to site. Truly ready for your design/build.

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    14 McGee Rd, Egremont, MA 01230
  • /37

    $796,000

    • 2 Beds
    • 2 Baths
    • 1,622 Sq Ft

    324 Park St, Great Barrington, MA 01230

    Architectural gem with lots of glass perched like a treehouse on the backside of Monument Mountain. The open, mid-century modern home was built in 2012 for maximum light, efficiency, and provides glittering views through the trees of the Housatonic River! 2 bedroom, 2 full baths-both ensuite + central AC, and a Scandinavian soapstone wood stove, permit included! Minutes from hiking trails, Taft

    Claudia Laslie LANCE VERMEULEN RE, INC

    324 Park St, Great Barrington, MA 01230
  • /29

    $629,000

    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft

    14 Miller View Rd, Egremont, MA 01230

    The private drive into this property says it all... Set well off a quiet cul-de-sac in a sought-after Egremont neighborhood on nearly 6 acres of lush, mature landscaping, this charming raised ranch offers the perfect blend of privacy and proximity. This beautifully maintained property is neat as a pin and move-in ready. With 3 bedrooms and 2 full baths, the main level features a light-filled open

    Dana Fuchs LANCE VERMEULEN RE, INC

    14 Miller View Rd, Egremont, MA 01230
  • /19

    $589,500

    • 3 Beds
    • 2 Baths
    • 1,520 Sq Ft

    74 Prospect Lake Rd, Egremont, MA 01230

    Enjoy lake access to Prospect Lake in a desirable low-tax area! This beautifully maintained contemporary home offers a first-floor primary bedroom with full bath, an open-concept kitchen, dining, and living area, plus an additional sitting room for flexible living space. Cherry wood floors, central air conditioning, and multiple skylights fill the home with natural light. Double French doors lead

    Suzann Ward HOUSATONIC REAL ESTATE

    74 Prospect Lake Rd, Egremont, MA 01230
  • /30

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,618 Sq Ft

    212 Highland St, Housatonic, MA 01236

    Nestled on a corner lot in the desirable town of Housatonic, this New England Farmhouse offers an abundance of space, a rocking chair front porch, a private rear courtyard, and a one-car garage. On the first floor is a comfortable living room with wood floors, a primary bedroom, a full bathroom, a dining room, a kitchen, and a gathering room with a wood stove. The second floor has 2 bedrooms and

    Lori Rose STONE HOUSE PROPERTIES, LLC

    212 Highland St, Housatonic, MA 01236
  • /56

    $1,200,000

    • 3 Beds
    • 3.5 Baths
    • 2,447 Sq Ft

    6 Muddy Brook Cir, Great Barrington, MA 01230

    Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming

    Eric Steuernagle FAIRGROUND REAL ESTATE, INC

    6 Muddy Brook Cir, Great Barrington, MA 01230
  • /27

    $365,000

    • 3 Beds
    • 1 Bath
    • 872 Sq Ft

    26 Pine St, Great Barrington, MA 01230

    LAKE BUEL, NEW MARLBOROUGH COTTAGE!For the past 60 years this cottage has been a source of joy for the same family, now it is your turn. Affordable, simple, rustic three season cottage with deeded access to the lake. Well loved and nicely maintained, with updated kitchen, and a beautiful stone fireplace for those chilly evenings. Nice open plan Living/Dining area. Relax on the Deck or gather

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    26 Pine St, Great Barrington, MA 01230
  • /78

    $4,500,000

    • 4 Beds
    • 3 Baths
    • 5,256 Sq Ft

    381 Sheffield-Egremont Rd, Sheffield, MA 01257

    SPECTACULAR ONE OF A KIND BERKSHIRE PROPERTY! This compound includes an elegant and updated 4 bedroom 1759 Colonial home and fabulous RED BARN with 2 separate guest spaces. Mill pond for fishing, heated pool, patios and screen porch, 66 protected SUBDIVIDABLE ACRES...with views of Mount Washington. The perfect place to entertain friends and family. An incredible opportunity for additional

    Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    381 Sheffield-Egremont Rd, Sheffield, MA 01257
  • /58

    $1,325,000

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    105 Christian Hill Rd, Great Barrington, MA 01230

    CLASSIC ARCHITECTURE WITH CONTEMPORARY ELEGANCE! A beautifully maintained home set back from the road. Exceptional landscaping embraces the property, offering a private sanctuary. A front porch welcomes you to the first floor. A light-filled,capacious living room, dining room with a fireplace opened to both main rooms, a primary suite with two walk-in closets, a 1/2 bath, and study open to a

    Mandy Victor-pieczarka STONE HOUSE PROPERTIES, LLC

    105 Christian Hill Rd, Great Barrington, MA 01230
  • /24

    $695,000

    • 2 Beds
    • 2 Baths
    • 1,308 Sq Ft

    80 Taconic Ave Unit 3, Great Barrington, MA 01230

    Welcome to Oakwood Condominium. A one car garage comes with unit. Plenty of additional parking. Lovely inground well manicured pool. Beautiful outdoor landscaping and sitting area. Private deck attached to unit for outdoor entertaining. This unit has been renovated over the years with updated kitchen with eat in nook area. All new windows and sliding doors. Gorgeous primary bathroom with radiant

    Suzann Ward HOUSATONIC REAL ESTATE

    80 Taconic Ave Unit 3, Great Barrington, MA 01230
  • /37

    $600,000

    • 6 Beds
    • 5 Baths
    • 3,502 Sq Ft

    53 Mahaiwe St, Great Barrington, MA 01230

    A prime investment opportunity in the heart of downtown Great Barrington. This 5-unit residential property features a desirable mix of four one-bedroom apartments and one two-bedroom unit. A significant advantage for this building is that all units are serviced by their own separate heating and electrical systems. Its convenient downtown location ensures high demand due to walking proximity to

    Tony Segalla LANCE VERMEULEN RE, INC

    53 Mahaiwe St, Great Barrington, MA 01230
  • /31

    $589,000 Open Sat 12:30PM - 2PM

    • 4 Beds
    • 2 Baths
    • 2,148 Sq Ft

    70 Main St, Great Barrington, MA 01230

    Charming 1790 Historic Home in the Heart of South EgremontNestled on a beautifully landscaped 0.8-acre lot in the heart of the village, this 4-bedroom, 2-bath home blends timeless charm with modern convenience. Built in 1790 it features wide plank floors, built-ins, and a fireplace with a historic Dutch oven.Enjoy local access to shops and dining, with scenic hiking at Jug End Reservation just

    Judi Panzano HOUSATONIC REAL ESTATE

    70 Main St, Great Barrington, MA 01230
  • /52

    $1,675,000

    • 4 Beds
    • 3.5 Baths
    • 3,783 Sq Ft

    42 Seekonk Rd, Great Barrington, MA 01230

    The Piano House was named for the ornamental Dentil wood trim at the top of the facade an 1810 Center Hall Federal Colonial, located on 4.59 acres at Alford Brook, Features a Rumford Fireplace in the Front Lounge and in the Sitting Room. Also, a Large Wood Burning Stove in the Dining Room-Family/Sunroom. In addition, an 1810, two story Barn with 1185 sq. ft. of refurbished space. Includes a

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    42 Seekonk Rd, Great Barrington, MA 01230
  • /20

    $999,999

    • 5 Baths
    • 5,180 Sq Ft

    406 Main St, Great Barrington, MA 01230

    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

    Jason Saphire www.HomeZu.com

    406 Main St, Great Barrington, MA 01230
  • /48

    $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
  • /20

    $1,250,000

    • 2 Beds
    • 2 Baths
    • 1,584 Sq Ft

    114 Brush Hill Rd, Great Barrington, MA 01230

    New Build Contemporary. Timbercraft Homes & Rosengren Architects collaborated to create this Contemporary 1584 square foot 2 bedroom home. Clean lines and simple one level living. Energy efficient Home with beautiful oak floors, custom kitchen open to dining and living room. Primary bedroom spacious and bright with well appointed bathroom and walk-in closet. Fireplace, dual fuel heating and AC. 1

    Mark Rosengren LANCE VERMEULEN RE, INC

    114 Brush Hill Rd, Great Barrington, MA 01230
  • /47

    $1,795,000

    • 4 Beds
    • 3 Baths
    • 2,686 Sq Ft

    24 Baldwin Hill Rd E, Egremont, MA 01230

    Located on one of Egremont's most picturesque roads, this beautifully designed contemporary home offers panoramic views from nearly every room. Set in a low-tax town just minutes from Great Barrington, this home is private, comfortable and versatile. The main house has perfect flow, great scale rooms, tons of light, a beautiful stone fireplace, custom Kitchen, and the prettiest of outdoor

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    24 Baldwin Hill Rd E, Egremont, MA 01230
  • /36

    $775,000

    • 10 Beds
    • 4 Baths
    • 5,293 Sq Ft

    458 Monterey Rd, Great Barrington, MA 01230

    This rare find, located on the Great Barrington/Monterey line, offers the right buyer a unique opportunity to live, work, and play in the heart of the Berkshires. Situated on 4.32 acres, this 1958 ranch-style home has evolved over the years into a sprawling 5,200 square-foot property boasting endless potential. While it currently serves as an owner-operated wellness facility, an expansive

    Cortney Dupont COHEN & WHITE ASSOCIATES

    458 Monterey Rd, Great Barrington, MA 01230
  • /46

    $649,900

    • 9 Beds
    • 4 Baths
    • 4,152 Sq Ft

    1057 Main St, Great Barrington, MA 01236

    Great investment opportunity! A very rare property offered for the first time outside the family in over 90 years! This is a well maintained and loved four unit income property that can produce over seventy five thousand dollars per year in rents! Lifetime metal roof, freshly painted exterior and updated units are just a few of the benefits of this investment. In the bustling village of

    Ryan Lane GILCREST PROPERTIES

    1057 Main St, Great Barrington, MA 01236
  • /53

    $849,000

    • 8 Beds
    • 4 Baths
    • 3,044 Sq Ft

    328 Park St, Great Barrington, MA 01230

    Two beautifully renovated duplexes within walking distance to the charming village of Housatonic. Enjoy scenic views of the Housatonic River from each unit. All utilities are separate, making this an ideal investment. All units are fully rented.

    Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    328 Park St, Great Barrington, MA 01230
  • /29

    $789,000

    • 3 Beds
    • 2 Baths
    • 1,771 Sq Ft

    165 Maple Ave Unit D, Great Barrington, MA 01230

    Beautiful condo with open plan concept, wide pine flooring and so much light. Upscale kitchen, first floor primary with bath and laundry. Three bedrooms, two full baths plus a bonus room waiting to be finished. There is also a lovely screened porch plus a rear deck for grilling. Live on one level. The walk out lower level could also be additional living space. It is beautifully landscaped within

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    165 Maple Ave Unit D, Great Barrington, MA 01230
  • /11

    $198,900

    • Land
    • 2.02 Acres
    • $98,563 per Acre

    229 Egremont Plain Rd, Egremont, MA 01230

    Discover your blank canvas in Egremont! This beautiful, cleared meadow offers flat, open field space, perfect for building your dream home, starting a small farm, or simply enjoying serene Berkshire surroundings. A rare find!

    Tony Segalla LANCE VERMEULEN RE, INC

    229 Egremont Plain Rd, Egremont, MA 01230
  • /48

    $2,995,000

    • 4 Beds
    • 4.5 Baths
    • 5,300 Sq Ft

    116 Brush Hill Rd, Great Barrington, MA 01230

    Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna, radiant floor & forced air throughout. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout

    Mark Rosengren LANCE VERMEULEN RE, INC

    116 Brush Hill Rd, Great Barrington, MA 01230
  • /23

    $149,000

    • Land
    • 1.11 Acres
    • $134,233 per Acre

    10 Miller View Rd, Egremont, MA 01230

    Tucked away on a quiet cul-de-sac in the desirable Baldwin Hill area of North Egremont, this 1.1 acre building lot offers seasonal mountain views and a serene setting. Partially cleared with easy access to an electrical transformer at the property's edge, this property is an ideal site for your future home. Conveniently situated just minutes from great Barrington, and all the Berkshire's has to

    Vashti Poor LANCE VERMEULEN RE, INC

    10 Miller View Rd, Egremont, MA 01230
  • /30

    $655,000

    • 5 Beds
    • 3 Baths
    • 3,035 Sq Ft

    133 Front St, Great Barrington, MA 01236

    Unique Mixed-Use Property in Downtown HousatonicPrime opportunity for investors or owner-occupants! This charming property features a successful ground-floor retail space and two spacious, income-producing 2-bedroom apartments above. Each unit includes a large kitchen, full bath, washer/dryer hookups, and an enclosed porch with town views.The commercial space has its own kitchen and bath ideal

    Judi Panzano HOUSATONIC REAL ESTATE

    133 Front St, Great Barrington, MA 01236
  • /3

    $349,000

    • Land
    • 72.98 Acres
    • $4,782 per Acre

    0 Lake Buel Rd, Great Barrington, MA 01230

    Beautiful Building Site - 72.98 acres in Great Barrington. Gently sloping land abuts the Appalachian Trail and East Mountain State Forest. Shared driveway off Aberdeen Road in New Marlborough. Cleared spot with a partially built barn/workshop on site. Rough driveway in place. Tranquil spot for your dream home!

    Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    0 Lake Buel Rd, Great Barrington, MA 01230
  • /35

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 1,922 Sq Ft

    220 N Plain Rd, Great Barrington, MA 01230

    An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could

    Martin Albert COMPASS MASSACHUSETTS , LLC GB

    220 N Plain Rd, Great Barrington, MA 01230
  • /82

    $2,300,000

    • 5 Beds
    • 4.5 Baths
    • 4,842 Sq Ft

    173 Hillsdale Rd, Egremont, MA 01230

    Nestled in a secluded, serene setting and surrounded by lush gardens, fruit trees, wildlife and protected land on three sides, this one-of-a-kind, custom-built home offers extraordinary privacy and tranquility. Crafted using wood milled directly from the property, this rustic yet contemporary home boasts a wealth of unique details that highlight exceptional craftsmanship and timeless beauty.

    Robert Cohen eXp REALTY

    173 Hillsdale Rd, Egremont, MA 01230
  • /52

    $2,324,000

    • 6 Beds
    • 5.5 Baths
    • 6,000 Sq Ft

    141 Stevens Lake Way, Monterey, MA 01245

    Discover Stevens Lake! This incredible property offers you a lifestyle that is unmatched in the modern world. The residence is perched overlooking the lake to experience spectacular sunrises. Entering from the garage there is a mud/laundry room which opens to the kitchen fit for any Chef. The kitchen features granite counters, Subzero and Viking appliances, a large pantry with an additional

    Derek Strzepa NOCHER REALTY

    141 Stevens Lake Way, Monterey, MA 01245
  • /25

    $419,000

    • 4 Beds
    • 1 Bath
    • 1,337 Sq Ft

    153 State Rd, Great Barrington, MA 01230

    Neat as a pin cape walking distance to downtown Great Barrington and amenities, this home has been thoughtfully renovated top to bottom. This sweet property has 4 bedrooms, a full bath, and even a partially finished basement. The kitchen, complete with a large pantry, retains the charming mid century details, while appealing to the modern aesthetic. Outside, there is a nice flat side yard, and

    Lauren Rosen LANCE VERMEULEN RE, INC

    153 State Rd, Great Barrington, MA 01230
  • /13

    $850,000

    • Land
    • 22.74 Acres
    • $37,379 per Acre

    0 Lake Buel Rd, Great Barrington, MA 01230

    Residential development opportunity! This expansive parcel offers potential for 17 building sites, ideally located just minutes from downtown Great Barrington and Butternut Ski Area. The property abuts the iconic Appalachian Trail, offering tranquil access to nature and recreation. Build a cul-de-sac community where residents can experience the best of the Berkshires--hiking, skiing, and vibrant

    Tony Segalla LANCE VERMEULEN RE, INC

    0 Lake Buel Rd, Great Barrington, MA 01230
  • /26

    $609,000 Open Sat 1:30PM - 2:30PM

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft

    54 Egremont Plain Rd, Great Barrington, MA 01230

    Great New England farmhouse with really nice views. Common rooms are amply sized and the kitchen great room is perfect for many different activities. Extra room on the first floor can be used as a bedroom or an office (not pictured.) Many extras - structural renovations in 2004, central air, in line generator, in ground pool, screened porch and so much charm. Nice 3.89 acre parcel with detached

    Katie Williams STONE HOUSE PROPERTIES, LLC

    54 Egremont Plain Rd, Great Barrington, MA 01230
  • /36

    $499,000 Open Sat 11AM - 2PM

    • 4 Beds
    • 2 Baths
    • 2,076 Sq Ft

    36 Egremont Plain Rd, Great Barrington, MA 01230

    Don't miss this charming 4-bed, 2-bath home with 2 first-floor bedrooms and a full bath! Offering nearly 2,100 sq. ft. of living space and almost 1 acre of flat, dry land, this home provides plenty of room to grow. The breezeway connects the 2-car garage with newer doors and electric openers. Outside, enjoy a private patio, stone wall, and a shed for extra storage. The home has also just had the

    William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    36 Egremont Plain Rd, Great Barrington, MA 01230
  • /10

    $485,000

    • 3 Beds
    • 2 Baths
    • 1,479 Sq Ft

    26 Manville St, Great Barrington, MA 01230

    Charming Updated Cape Style Home in Prime Great Barrington LocationDiscover this beautifully renovated three-bedroom, two-bath Cape style home nestled in a coveted in-town neighborhood of Great Barrington. Thoughtfully updated with modern touches, this inviting residence offers a perfect blend of classic charm and contemporary comfort.Inside, enjoy gleaming hardwood floors throughout the main

    Eric Steuernagle FAIRGROUND REAL ESTATE, INC

    26 Manville St, Great Barrington, MA 01230
  • /11

    $899,000

    • Land
    • 10.5 Acres
    • $85,619 per Acre

    55 Prospect Lake Rd, Egremont, MA 01230

    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

    Suzann Ward HOUSATONIC REAL ESTATE

    55 Prospect Lake Rd, Egremont, MA 01230
  • /14

    $1,495,000

    • Land
    • 17.97 Acres
    • $83,194 per Acre

    59 White Hill Rd, Egremont, MA 01230

    At the peak of a ridge, part of an exclusive enclave of seven luxury homes, this rare offering comprises 18 secluded acres, breathtaking views, and a set renderings (see photos) and plans evoking the best in modernist design. Part of a visionary project developed by veteran AD100 Architect Steven Haas, the property is encompassed by 220 acres of private, protected, natural beauty, which

    Gladys Montgomery WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    59 White Hill Rd, Egremont, MA 01230
  • /61

    $2,500,000

    • 4 Beds
    • 4.5 Baths
    • 3,100 Sq Ft

    1373 Boardman St, Sheffield, MA 01257

    The ULTIMATE LIVE-WORK-PLAY RETREATStep onto a property as striking as the Berkshires themselves--where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The 13,738 sq ft retreat fondly known as ''The Factory'' spans 5+ acres with views of rolling hills & protected fields. 10,000 sq ft of versatile commercial and creative space below and flanked

    Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    1373 Boardman St, Sheffield, MA 01257

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