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Homes for Sale near Red Hook Senior High School

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  • /37

    $1,799,000

    • 5 Beds
    • 4.5 Baths
    • 5,490 Sq Ft

    161 Whalesback Rd, Red Hook, NY 12571

    Don’t miss this rare opportunity to own a breathtaking, fully renovated 5,500 sq ft converted barn in the heart of the Hudson Valley. Nestled on 15 private, picturesque acres in the safety and tranquility of Red Hook, NY, this extraordinary 5-bedroom, 4.5-bathroom home seamlessly blends historic charm with modern luxury.Originally built in 1900, the barn has been thoughtfully transformed to

    Agent Photo

    Ann Stettner

    Neil Charles Real Estate, LLC

    (845) 448-2559

    161 Whalesback Rd, Red Hook, NY 12571
  • /32

    $485,000

    • 4 Beds
    • 2 Baths
    • 2,238 Sq Ft

    5165 Route 9g, Tivoli, NY 12583

    Welcome to the Tivoli Farmhouse! Built in 1900 and renovated in 2018, it has been lovingly updated to offer country living with modern amenities. Having had several uses over the years, the 2328 square foot property is a functional home with 4 bedrooms and 2 bathrooms. The first level has a very nice floor plan; from the hallway entry you can enter the appointed living room that conveniently

    Victoria Stent Coldwell Banker Village Green

    5165 Route 9g, Tivoli, NY 12583
  • /50

    $839,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 2 Baths
    • 1,784 Sq Ft

    280 Pitcher Ln, Red Hook, NY 12571

    Step into timeless elegance with this beautifully maintained and thoughtfully updated 2-story, Craftsman style home, perfectly situated on 1.06 acres of mature, landscaped grounds in the heart of the Hudson Valley. This 4-bedroom, 2-bath residence blends original charm with modern conveniences, offering the perfect balance of character and comfort.From the moment you arrive, you will be

    Vincenza Seche Howard Hanna Rand Realty

    280 Pitcher Ln, Red Hook, NY 12571
  • /47

    $729,000

    • 4 Beds
    • 3 Baths
    • 2,559 Sq Ft

    7432 S South Broadway, Red Hook, NY 12571

    Take a step back to a simpler time in this charming Circa 1920 4 bed 3 bath Victorian home. Located in the beautiful village of Red Hook, Dutchess county. The town once named Hardscrabble offers all the convenience of modern day life. Multiple excellent restaurants, supermarket, juice bar, a health food shop, art galleries, a Pilates studio and much more. The 2,559 square foot stately

    Anthony Winters Upstate Down

    7432 S South Broadway, Red Hook, NY 12571
  • /50

    $750,000

    • 3 Beds
    • 2.5 Baths
    • 1,992 Sq Ft

    7641 N Broadway, Red Hook, NY 12571

    Discover the charm of Red Hook, New York, in this captivating ranch-style residence at 7641 N Broadway. This beautifully maintained single-family home offers 2,657 sq. ft. of total space across two floors, with 1,992 sq. ft. of living area on the main level and a full basement below.Inside, you'll find four generously sized bedrooms and two full bathrooms, plus a convenient half bath. The

    Ryan Sylvestri RE/MAX Town & Country

    7641 N Broadway, Red Hook, NY 12571
  • /31

    $799,999

    • 4 Beds
    • 2.5 Baths
    • 3,370 Sq Ft

    117 Deer Run Rd, Red Hook, NY 12571

    Welcome to this elegant four bedroom, two and a half-bath Colonial gracefully set on three beautifully manicured acres in one of Red Hook’s most desirable executive neighborhoods. Thoughtfully designed for both comfort and style, this home offers timeless curb appeal with its charming rocking chair front porch and classic architectural lines.Step inside to a spacious and light-filled layout

    Peggy Santamorena Houlihan Lawrence Inc.

    117 Deer Run Rd, Red Hook, NY 12571
  • /23

    $650,000

    • 3 Beds
    • 1 Bath
    • 2,154 Sq Ft

    2322 Us Route 9, Hudson, NY 12534

    Charming Home on 10.27 acres with Pond & Vineyard - Zoned Commercial.Welcome to 2322 US Route 9, a unique 10.27-acre property in the town of Livingston offering a blend of historic charm and modern opportunity.This 1930s single-family home includes a two-car detached garage with an attached shed, plus a spacious two-story barn in the back, providing ample storage or workspace.Zoned commercial,

    Laurel Jurkowski Coldwell Banker Advisor Realty

    2322 Us Route 9, Hudson, NY 12534
  • /46

    $1,100,000

    • 4 Beds
    • 2 Baths
    • 2,763 Sq Ft

    345 Metzger Rd, Rhinebeck, NY 12572

    Escape with us to Red Hook, NY! Hidden amongst a canopy of trees, down a long, meandering, private drive, sits this spacious Cape Cod overlooking 10+ acres of the most beautiful, organic gardens and orchards. Enjoy having the convenience of both Rhinebeck and Red Hook Villages at your fingertips, but the feeling of being in your own little piece of Hudson Valley paradise. Head out in the morning

    Miranda Alger Mondello Upstate Properties

    345 Metzger Rd, Rhinebeck, NY 12572
  • /43

    $699,000

    • 3 Beds
    • 2 Baths
    • 2,200 Sq Ft

    47 Clay Hill Rd, Tivoli, NY 12583

    Charming recently renovated ranch nestled on a private corner lot in a quiet neighborhood in the Village of Tivoli yields a scenic view and walkable distance to all the picturesque shops. This property offers a perfect blend of privacy and space with almost an acre yet convenience with access as the heart of town is around the corner and a quick drive Bard college, Poets Walk, Rhinebeck, Red Hook

    Lorraine Little LITTLE LORRAINE ML

    47 Clay Hill Rd, Tivoli, NY 12583
  • /31

    $759,900

    • 4 Beds
    • 4 Baths
    • 3,858 Sq Ft

    37 Pine Ln, Tivoli, NY 12583

    Get ready to have the summer of your dreams in this impeccably cared for turnkey Center Hall Colonial style home in serene country setting. Tucked away at the end of a private road, you instantly feel welcomed as you enter a spacious and bright Living Room with a pellet stove. You will love to dine in the eat in Kitchen with brand new appliances and multitude of counter space. Formal Dining Room

    ANGELINA POLLARD Mondello Upstate Properties

    37 Pine Ln, Tivoli, NY 12583
  • /42

    $759,900

    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft

    224 Fraleigh Ln, Red Hook, NY 12571

    Country Cape on near end cul-de-Sac situate on 6 private acres , country kitchen with dining area ,LR with mason chimney pellet stove. double dutch door lead to4 season room, access to L shaped decking with jacuzzi, overlooking fire pit and landscaped yard and fenced in pool 16x36 area.Hardwd floors on main floor, and tile flrd baths ,4 Bedrooms,( 2 up, 2 down) 2 updated full baths (1

    Karen Vetere Vetere, Karen Real Estate

    224 Fraleigh Ln, Red Hook, NY 12571
  • /38

    $799,000

    • 3 Beds
    • 3.5 Baths
    • 3,600 Sq Ft

    12 Broadview Ln, Red Hook, NY 12571

    Tucked right outside the village of Red Hook, is the lovely neighborhood on Broadview Lane, where you have the unique luxury of extensive private acreage but also enjoy the community setting. This custom colonial is both elegant and cozy; it has been carefully curated with immaculate details featuring crown moldings, recessed lighting, and beautiful hardwood floors. Welcome your guests into the

    Chelsea Pollard-Seiler Mondello Upstate Properties

    12 Broadview Ln, Red Hook, NY 12571
  • /39

    $649,000

    • 6 Beds
    • 2 Baths
    • 3,100 Sq Ft

    11-13 Eldridge Ln, Red Hook, NY 12571

    Red Hook Village Compound! Once in a generation a property offering like this is available. Tucked in at the end of Eldridge lane in the village walkable to parks, shoppes, and restaurants. This is composed of a lovely four bedroom home, with 2 sunrooms, large living room with stone fireplace, massive bathroom with skylights, new roof with warranty, new skylights and carpets. The home is light

    Chelsea Pollard-Seiler Mondello Upstate Properties

    11-13 Eldridge Ln, Red Hook, NY 12571
  • /34

    $749,000

    • 4 Beds
    • 4 Baths
    • 2,300 Sq Ft

    8 Orlich Rd, Red Hook, NY 12571

    Welcome to 8 Orlich Road - a beautifully designed home offering endless possibility! This property is perfect for those seeking both space and versatility, with features that cater to a wide range of needs and lifestyles. The main level boasts four bedrooms including a private primary suite with large en-suite bath and plenty of closet space. The heart of the home includes an open-plan living and

    Hayes Clement Compass Greater New York, LLC

    8 Orlich Rd, Red Hook, NY 12571
  • /44

    $998,000

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

    6 Livingston St, Red Hook, NY 12571

    This pristine condition, thoughtfully designed home in Tradition at Red Hook offers a rare blend of sophistication, comfort, and low-maintenance living—just a two hour drive from NYC. Immaculately maintained and featuring high-end finishes throughout, this move-in-ready retreat provides a seamless living experience with four distinct sleeping environments, in a vibrant, community-oriented

    Harris Safier Compass Greater NY, LLC

    6 Livingston St, Red Hook, NY 12571
  • /36

    $734,900

    • 3 Beds
    • 2.5 Baths
    • 2,864 Sq Ft

    7 Glen View Dr, Red Hook, NY 12571

    Begin each morning in tranquil serenity at this 1993 Cape Cod style residence, positioned at the end of a peaceful country lane just two miles from the center of Red Hook Village. The country kitchen and dining room flow seamlessly into a screened porch, creating an ideal setting for both daily moments and memorable gatherings. Sip your morning coffee while watching wildlife in the wooded

    Linda Lindsay Upstate Down

    7 Glen View Dr, Red Hook, NY 12571
  • /25

    $695,000

    • 3 Beds
    • 2 Baths
    • 1,984 Sq Ft

    81 W Market St, Red Hook, NY 12571

    The A.J. Davis Mid- 19th Century Gardener's Cottage -A rare opportunity to own a piece of Hudson Valley history, The Gardener's Cottage, once part of Maizefield. This property was built in the mid- 19th century and the architect commissioned was Alexander Jackson Davis, a very prominent man of his time. It is a two story, three-by-one-bay timber frame cottage, on an exposed stone foundation, with

    Brock Anderson Four Seasons Sotheby's Int.

    81 W Market St, Red Hook, NY 12571
  • /15

    $399,925

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft

    10 Aspinwall Rd, Red Hook, NY 12571

    Upgraded one level living ranch in wonderful location, close to Route 9 and all amenities. This home has been freshly painted, new carpeting installed, new doors, new bathroom and is ready for its next owner. Perfect for first time home buyer or anyone downsizing.Large Country kitchen with sizeable eating area and sliding glass doors to large level backyard, walk into the large living room

    Patricia Cannizzaro Century 21 Alliance Rlty Group

    10 Aspinwall Rd, Red Hook, NY 12571
  • /25

    $599,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    44 Woods Rd, Tivoli, NY 12583

    The one you have been waiting for is finally here! Located on a picturesque side street in Tivoli Village, is this practical and one of a kind one level home. Greeting you when you pull up is wide plank front porch with ceiling fan, made perfect for sitting on summer evenings with a cold beverage in hand listening to the crickets. Enter into the living room with bay window and wood stove, it

    Chelsea Pollard-Seiler Mondello Upstate Properties

    44 Woods Rd, Tivoli, NY 12583
  • /35

    $75,000

    • 2 Beds
    • 2 Baths
    • 1,064 Sq Ft

    16 Spruce St, Hudson, NY 12534

    PLEASE NOTE: Seller is unable to close until late January/early February 2026. Will firm up the timing w Seller. Washing machine not included in sale.Original owner has beautifully maintained her home. It is in move-in condition! Situated on a roomy corner lot in the Red Hook School District section of Maple Lane Mobile Home Park. Lovely, comfortable front porch w sunshades is the

    Elizabeth Barrett Dachs Chris Barrett Realty

    16 Spruce St, Hudson, NY 12534
  • /35

    $9,450,000

    • 3 Beds
    • 4.5 Baths
    • 6,216 Sq Ft

    151 Rowe Rd, Red Hook, NY 12571

    Crestline is a visionary to-be-built residence with 6,216 finished square feet of meticulously designed living space, including three bedroom suites and four-and-a-half luxurious baths. Perched atop a 41-acre hilltop with commanding 360-degree views of the Catskills, Stissing Mountain, and the rolling agricultural valleys below, this architectural masterpiece harmonizes with its natural

    Sean Eidle BHHS Hudson Valley Properties

    151 Rowe Rd, Red Hook, NY 12571
  • /32

    $3,450,000

    • 4 Beds
    • 3.5 Baths
    • 4,110 Sq Ft

    15 Shookville Rd, Red Hook, NY 12571

    Introducing Shookville Road, a striking 4,000+ sq ft modern contemporary home set on park-like grounds with sweeping views to a spring fed 25-foot-deep swimming pond and verdant forest beyond. Designed by Architect James Bartholomew, this residence is a study in light, space, and harmony with nature. A soaring two-story wall of windows anchors the main living space, artfully blurring the line

    Julia Crowley Rouse + Co Real Estate, LLC

    15 Shookville Rd, Red Hook, NY 12571
  • /29

    $625,000

    • 3 Beds
    • 3 Baths
    • 2,300 Sq Ft

    110 Read Rd, Red Hook, NY 12571

    This well-maintained Cape Cod Style exemplifies a "pride of ownership". You will enjoy relaxing in the comfortable Living Room with its vaulted ceilings, skylights and hardwood floors. The Eat in Kitchen has been upgraded with stainless appliances and is abundant with cabinetry and conveniently accesses a two-car Garage with a loft for storage or other potential. The "Crown Jewel" of the home is

    Catherine Mondello Mondello Upstate Properties

    110 Read Rd, Red Hook, NY 12571
  • /39

    $459,000

    • 4 Beds
    • 1.5 Baths
    • 1,672 Sq Ft

    252 Route 199, Red Hook, NY 12571

    This well-loved property has been owned by the same family for almost 65 years! Hardwood floors & natural woodwork are throughout. More recent 2 rm addition features a 3-season room w vaulted wood ceiling & propane stove, plus an additional bedroom or family room w 3 closets. Dry basement features a 4th BR or FR, utility room, plus room for 3 cars. This space could easily be finished for extra

    Elizabeth Barrett Dachs Chris Barrett Realty

    252 Route 199, Red Hook, NY 12571
  • /30

    $365,000

    • 3 Beds
    • 1 Bath
    • 1,160 Sq Ft

    9 Roger Ct, Red Hook, NY 12571

    Nestled on a private road shared with just two other homes, this recently renovated ranch offers an out-of-the-way location, minutes from the heart of Red Hook.A newly built front deck welcomes you home, providing the perfect spot to enjoy your morning coffee or entertain guests. Step inside to a light-filled living room featuring large windows and warm wood wainscoting, seamlessly connected

    KIMBERLEY MILLER BHHS Hudson Valley Properties

    9 Roger Ct, Red Hook, NY 12571
  • /22

    $434,900

    • 3 Beds
    • 2 Baths
    • 1,302 Sq Ft

    18 Amherst Rd, Red Hook, NY 12571

    Beautiful town of Red Hook home that has been lived in and loved for years. With many updates and additions this 5 bedroom home is priced to sell quickly. Private 1st floor main bedroom with ensuite bathroom plus 2 more bedrooms and another full bath on the first floor. Downstairs has been fully finished with a bedroom, full bath, storage room and a tv/work out area. Walk into town to enjoy

    MARIE MONROE BHHS Hudson Valley Properties

    18 Amherst Rd, Red Hook, NY 12571
  • /32

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    167 Benner Rd, Red Hook, NY 12571

    In the much requested Red Hook School District, this 1900 SF, 3 BR, 2.5 bath, 7 room one story is move-in ready, is the PERFECT COUNTRY HOME. On a very pretty country road just 1/2 mile from the village, this home is surrounded by 1.47 manicured acres. There is exceptional privacy here, buffered level lawns, & a huge 19 x 26 Trex deck for outdoor living. Inside is special with the most

    Paul Hallenbeck BHHS Hudson Valley Properties

    167 Benner Rd, Red Hook, NY 12571
  • /15

    $545,000

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft

    84 Montgomery St, Tivoli, NY 12583

    Welcome to the Obermeyer House, located on a quiet village road in the vibrant Village of Tivoli, this classic eyebrow colonial offers timeless character and an unbeatable location. Fred Obermeyer was the last veteran of the Mexican War and died at the age of 85. Built around 1860 and once used as a billiards hall, the home features original hardwood floors, vintage charm, and a welcoming layout

    TRACY DOBER Rouse + Co Real Estate LLC

    84 Montgomery St, Tivoli, NY 12583
  • /4

    $175,000

    • Land
    • 3.39 Acres
    • $51,622 per Acre

    0 Whalesback Rd, Red Hook, NY 12571

    Pretty elevated building lot with Peek a Boo Catskill views embraced and encompassed by mature oak trees. Set way back off country road minutes to Village of Red Hook, Rhinebeck, Bard College, Kingston Rhinecliff Bridge and all the finer things the Hudson Valley offers. Driveway in. BOHA in place.

    Catherine Mondello Mondello Upstate Properties

    0 Whalesback Rd, Red Hook, NY 12571
  • /19

    $425,000

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft

    10 Tobacco Ln, Red Hook, NY 12571

    Charming Village Home in the Heart of Red Hook! Tucked away on a quiet side street in the heart of Red Hook Village, this delightful one-story home offers a rare combination of comfort, convenience, and character and just a short stroll from shops, cafes, and all the village has to offer. This 2-bedroom, 1.5-bath residence features gleaming hardwood floors throughout, with abundant natural

    Margaret Niekrewicz Margaret Mondello Real Estate

    10 Tobacco Ln, Red Hook, NY 12571
  • /37

    $595,900

    • 4 Beds
    • 4 Baths
    • 3,344 Sq Ft

    2323 Us Route 9, Hudson, NY 12534

    Burroughs-Foland Farm - A Timeless Treasure in Livingston - Prime Commercial Opportunity - 2 Houses -Discover a unique opportunity with this historic property, proudly listed on the National Register of Historic Places. Built-in 1908, this mission-style home combines Old World charm with modern potential, featuring a stucco facade and classic clay tile roof. On the market for the first time in

    Laurel Jurkowski Coldwell Banker Advisor Realty

    2323 Us Route 9, Hudson, NY 12534
  • /17

    $559,000

    • 3 Beds
    • 2 Baths
    • 1,972 Sq Ft

    1626 Route 9, Tivoli, NY 12583

    This delightful 3-bedroom*, 2-bath* home offers peaceful living just minutes from Red Hook and Hudson. Set on a private lot with a pond, this property combines the best of convenience and country charm. Step inside to find sun-filled rooms, hardwood floors, and a cozy, welcoming vibe throughout. Enjoy morning coffee on the front porch and unwind on the back deck while watching the sunset over

    Lindsay Schultz JFIVE HOMES REALTY LLC

    1626 Route 9, Tivoli, NY 12583
  • /20

    $599,000

    • Land
    • 29 Acres
    • $20,669 per Acre

    78-79 Fox Ln, Clermont, NY 12583

    This exceptional 29-acre property in Tivoli, NY, presents a rare opportunity to craft a private sanctuary amidst the natural beauty of the Hudson Valley. Set at the end of quiet Fox Lane, the approach is nothing short of enchanting, with a stone bridge crossing a gentle stream and leading to a world apart. Comprising two distinct tax lots, the land is fully Board of Health approved for the

    Angelica Ferguson Houlihan Lawrence-R

    78-79 Fox Ln, Clermont, NY 12583
  • /10

    $399,000

    • Land
    • 10 Acres
    • $39,272 per Acre

    0 Pleasantvale Rd, Tivoli, NY 12583

    Your Hudson Valley dream enclave awaits. Set at the end of a quiet road lined with hard woods framing your drive to paradise, this 10-acre parcel is something out of a story book. Bucolic and majestic views unroll on every acre of this parcel. The perfect home site has already been chosen, with dreamy views of rolling greens and the tops of the Catskill mountains perched behind it. This prime

    Chelsea Pollard-Seiler Mondello Upstate Properties

    0 Pleasantvale Rd, Tivoli, NY 12583
  • /45

    $1,399,999 Open Sun 12PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 4,568 Sq Ft

    145 Whalesback Rd, Red Hook, NY 12571

    Welcome to this stunning colonial-style residence, beautifully situated on 6.26 acres in the scenic HudsonValley. This exceptional home greets you with a grand entrance, as pink cherry blossoms line thedriveway leading to a spacious three-car garage, while elegant Japanese Red Maples frame the street.Zoned for up to four horses, this private estate offers a perfect blend of charm and

    Nancy Gaska Coldwell Banker American Homes

    145 Whalesback Rd, Red Hook, NY 12571
  • /25

    $165,000

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    13 Pine St, Hudson, NY 12534

    SPACIOUS, CHARMING, & AFFORDABLE! This 3 bedroom, 2 full bath, double wide manufactured home is move-in ready with tons of recent improvements! Situated on an oversized corner lot with a small running creek and lots of full grown trees providing plenty of privacy. Enter the front door through a wonderful enclosed screened in porch large enough to fit a dining table or to create a peaceful

    JEFFREY COLTON Jeff S. Colton

    13 Pine St, Hudson, NY 12534
  • /31

    $455,000

    • 3 Beds
    • 2 Baths
    • 2,052 Sq Ft

    287 Norton Rd, Red Hook, NY 12571

    Discover the perfect blend of comfort and seclusion in this charming 3- bedroom, 2-bath ranch, ideally set on a private, wooded lot with a picturesque pond. This home welcomes you with an open and airy floor plan, featuring a spacious living area filled with natural light and views of the surrounding landscape. Whether you're looking for a year-round residence or a serene weekend retreat, this

    Amanda Wilcox eXp Realty

    287 Norton Rd, Red Hook, NY 12571
  • /47

    $2,499,000

    • 4 Beds
    • 3 Baths
    • 4,020 Sq Ft

    202 Buckwheat Bridge Rd, Germantown, NY 12526

    There will be a public Open House on Sunday 7/13 from 12:00 to 3:00. Thank you.This historic house is a timeless beauty. Ice skate on the pond, garden in the greenhouse, and fish and swim in the creek, which borders the property on its south side. Looking for a meditative practice? Stroll the orchard, practice your art in one of the many outbuildings perfect for a studio, or read a book in

    CYNTHIA FENNELL Patricia A. Hinkein Realty

    202 Buckwheat Bridge Rd, Germantown, NY 12526
  • /28

    $449,000

    • 3 Beds
    • 1.5 Baths
    • 2,100 Sq Ft

    252 Rokeby Rd, Red Hook, NY 12571

    Charming Red Hook Retreat – 3BR, 2BA + 2000 Sq Ft Workshop! Bring your vision and make this solid home your own! This spacious 3-bedroom, 2-bath property is set on a flat, private 1-acre lot with mature trees, and lush landscape, located just minutes from the Village of Red Hook, local schools, and offering a quick commute to Kingston and Hudson. Step inside to find a bright, sunny kitchen with

    Margaret Niekrewicz Margaret Mondello Real Estate

    252 Rokeby Rd, Red Hook, NY 12571
  • /49

    $2,500,000

    • 4 Beds
    • 4.5 Baths
    • 4,960 Sq Ft

    163 Hapeman Hill Rd, Red Hook, NY 12571

    Nestled in the heart of the Hudson Valley, this striking custom-built compound offers a rare combination of luxury, privacy, and serenity. Set on 3.15 acres of beautifully landscaped grounds, the estate includes a main residence, a legal accessory apartment/guest house, a commercial-sized detached garage, an in-ground heated pool, a pool pavilion, and multiple outdoor living spaces—all

    Sean Eidle BHHS Hudson Valley Properties

    163 Hapeman Hill Rd, Red Hook, NY 12571

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