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Woodstock, NY Homes for Sale

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  • /29

    $979,000

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    14 Old Forge Rd, Woodstock, NY 12498

    Discover the perfect blend of historic charm and modern luxury in this exquisitely renovated 1900 carriage house. This exceptionable home features 2 bedrooms and 2 bathrooms, offering a harmonious balance of classic elegance and contemporary convenience.Step into the brand new kitchen, equipped with state of the art Bosch appliances and custom cabinetry from Transformad.com, features a

    Agent Photo

    Danielle Sevier

    Compass Greater NY, LLC

    (845) 385-1496

    14 Old Forge Rd, Woodstock, NY 12498
  • /32

    $1,195,000

    • 4 Beds
    • 6 Baths
    • 2,980 Sq Ft

    12 Tinker St, Woodstock, NY 12498

    Prime Village Green Historic Gem in Woodstock, NY. Discover a unique opportunity to own a piece of history in the heart of Woodstock. This remarkable 1875 era property originally known as The Snyder Homestead named after its original owner, was the grandest house in town. This old style home with its distinctive Mansard roof retains its grandeur to this day. It offers the quintessential blend of

    Agent Photo

    Danielle Sevier

    Compass Greater NY, LLC

    (845) 436-3857

    12 Tinker St, Woodstock, NY 12498
  • /31

    $975,000

    • 4 Beds
    • 4 Baths
    • 1,811 Sq Ft

    33 Tannery Brook Rd, Woodstock, NY 12498

    Nestled in the heart of Woodstock, this beautifully transformed farmhouse, originally constructed in the 1870s, seamlessly blends historic charm with modern living. The current owners, a talented architect and interior designer, have meticulously renovated this property to enhance its original architecture while maximizing natural light and integrating the surrounding landscape. The zoning allows

    Agent Photo

    Danielle Sevier

    Compass Greater NY, LLC

    (845) 456-8466

    33 Tannery Brook Rd, Woodstock, NY 12498
  • /77

    $5,200,000

    • 10 Beds
    • 8 Baths
    • 7,991 Sq Ft

    16-26 Shultis Brook Rd, Bearsville, NY 12409

    Historic compound located in the iconic hamlet of Bearsville, just minutes from the Village of Woodstock. This four residence compound dates back to the mid-1700's and is believed to be the first farm in the valley as well as one of the first homes. Sprawled over 25+ acres with a pond and meandering stream, this unique property tucked away with complete privacy. The four structures include a 3+

    Agent Photo

    Amy Hawks

    Berardi Realty

    (845) 250-0616

    16-26 Shultis Brook Rd, Bearsville, NY 12409
  • /40

    $1,595,000 New Construction

    • 3 Beds
    • 4 Baths
    • 3,544 Sq Ft

    18 Ryan Dr, West Hurley, NY 12491

    Built in 2022, this modern home balances thoughtful design with a connection to nature. Every aspect of the home has been done with intention, including its private location nestled in the woods, energy efficient features and open, light-filled spaces. This is a rare find - a recently built home with privacy less than 15 minutes from both Woodstock and Kingston. As you approach the house

    Agent Photo

    Hillary Kolos

    Compass Greater NY, LLC

    (845) 534-6610

    18 Ryan Dr, West Hurley, NY 12491
  • /33

    $1,649,000

    • 3 Beds
    • 2.5 Baths
    • 3,076 Sq Ft

    16 Juniper Ln, Woodstock, NY 12498

    Welcome to Juniper Woods. Nestled on four serene acres just minutes from the center of Woodstock, Juniper Woods is a custom-designed, exquisitely renovated residence offering the perfect balance of sophistication, tranquility, and convenience. With over 3,000 square feet of thoughtfully curated living space, this three-bedroom, three-bathroom home is rare, architecturally striking, and deeply

    Victoria Stent Coldwell Banker Village Green

    16 Juniper Ln, Woodstock, NY 12498
  • /47

    $799,000

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

    39 Van Wagner Rd, Willow, NY 12495

    Experience the epitome of country living with this historic farm home nestled in the heart of the Catskill Mountains. Whether you’re looking for your forever home, a weekend escape, or to start an Airbnb, this spacious home has it all! With nearly 2000 sqft of living space, this charming abode features a BRAND NEW METAL ROOF and GUTTERS, ALL NEW WINDOWS, 5 bedrooms and 3 full bathrooms, each

    Gina Nikola Keller Williams Valley Realty

    39 Van Wagner Rd, Willow, NY 12495
  • /50

    $4,999,000

    • 4 Beds
    • 4 Baths
    • 3,899 Sq Ft

    18 Striebel Rd, Woodstock, NY 12498

    Nestled in the heart of Woodstock, this extraordinary 70+ acre estate is a rare offering of artistic heritage, architectural beauty, and serene natural surroundings. Known as The Stone House on Striebel Road, this iconic bluestone compound has stood at the crossroads of music, literature, and counterculture for over a century.Built in 1914 as a country retreat, the main Stone House

    Michelle Bergkamp Corcoran Country Living

    18 Striebel Rd, Woodstock, NY 12498
  • /31

    $995,000 Open Sat 2PM - 4PM

    • 3 Beds
    • 2.5 Baths
    • 2,430 Sq Ft

    220 John Joy Rd, Wood Stock, NY 12498

    Welcome to 220 John Joy Road, a meticulously maintained and thoughtfully upgraded home tucked away in the heart of Woodstock, NY. Featuring three spacious bedrooms and two and a half baths, this property combines modern amenities with timeless charm, offering a rare opportunity to live comfortably and securely in one of the Hudson Valley's most beloved areas. Built with concrete walls for

    Donna Gray Redfin Real Estate

    220 John Joy Rd, Wood Stock, NY 12498
  • /51

    $759,000

    • 3 Beds
    • 2 Baths
    • 1,532 Sq Ft

    97 John Joy Rd, Woodstock, NY 12498

    The best of both worlds!A boho cottage paradise and a modern ADU (Accessory Dwelling Unit). Peace and tranquility and 3 miles from the center of the most famous small town in the world. Five-star dining and unique shopping opportunities.The property is situated adjacent to the Thorne Preserve - 60 acres boasting the most painted views of Overlook Mountain. The preserve is a

    Benjamin Armento Coldwell Banker Village Green

    97 John Joy Rd, Woodstock, NY 12498
  • /43

    $1,244,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,088 Sq Ft

    178 Chestnut Hill Rd, Woodstock, NY 12498

    Discover the epitome of modern luxury in this brand new build, with a sleek aesthetic that seamlessly blends style and comfort. Using ecological and state of the art building practices highlighted by exceptional craftsmanship and distinctive design. Ascend an impressive switchback floating staircase to a stunning wall of windows that flood the open concept, living, kitchen, and dining area

    Richard Vizzini Corcoran Country Living

    178 Chestnut Hill Rd, Woodstock, NY 12498
  • /47

    $1,345,000

    • 3 Beds
    • 3 Baths
    • 2,327 Sq Ft

    263 California Quarry Rd, Woodstock, NY 12498

    Live above the clouds over Woodstock, the world's most famous little town. This remarkable contemporary home is just a few minutes from the bustling center of the village, in an absolutely tranquil setting! The views are breath-taking and expansive, and seen from almost every room. The Ashokan Reservoir, the entire Shawangunk Mountain Ridge (from Mohonk to Sam's Point) Ohayo Mountain, and, even

    Daniel Winn Halter Associates Realty

    263 California Quarry Rd, Woodstock, NY 12498
  • /44

    $925,000

    • 4 Beds
    • 3 Baths
    • 2,044 Sq Ft

    4868 New York 212, Willow, NY 12495

    Escape to the Catskills with this exquisitely remodeled home in Willow - where privacy, luxury, and mountain views converge on 3.6 pristine acres just minutes from the heart of Woodstock. This 5-bedroom, 3-bathroom home is a masterclass in modern design and thoughtful craftsmanship, with every detail curated for comfort, style, and effortless living. Inside, you'll find an airy open-concept

    Richard Vizzini Corcoran Country Living

    4868 New York 212, Willow, NY 12495
  • /43

    $1,450,000

    • 4 Beds
    • 5 Baths
    • 3,080 Sq Ft

    27 Old Wagon Rd, Woodstock, NY 12498

    Just a half mile from the center of Woodstock, this bucolic 3.7-acre compound offers a rare blend of architectural charm, natural beauty, and versatile living. The property includes the main house and two outbuildings, a one-bedroom cottage and a studio with an attached three-bay garage. Bedroom and bath layout described as the primary residence having three bedrooms and three full baths

    Megan Rios Berardi Realty

    27 Old Wagon Rd, Woodstock, NY 12498
  • /45

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 3,080 Sq Ft

    11 Grogkill Rd, Willow, NY 12495

    Classic Country ''Haven'' — it's HEAVEN really! Elegance that checks off every box! This timeless and enduring style home designed with graciously proportioned rooms with high ceilings and light streaming through windows from every direction. Centrally located and perched on 3 exclusive landscaped acres with a pool, an oversized 2-car garage, and mountain views; all next door to your own country

    Sharon Breslau BHHS Hudson Valley Properties

    11 Grogkill Rd, Willow, NY 12495
  • /47

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 3,080 Sq Ft

    11 Grog Kill Rd, Willow, NY 12495

    Classic Country ''Haven'' — it's HEAVEN really! Elegance that checks off every box! This timeless and enduring style home designed with graciously proportioned rooms with high (12') ceilings and light streaming through windows from every direction. Centrally located and perched on 3 exclusive landscaped acres with a pool, an oversized 2-car garage, and mountain views; all next door to your own

    Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

    11 Grog Kill Rd, Willow, NY 12495
  • /53

    $1,695,000

    • 3 Beds
    • 3.5 Baths
    • 3,072 Sq Ft

    253 Upper Byrdcliffe Rd, Woodstock, NY 12498

    Historic Byrdcliffe Estate on One of Woodstock's Most Beloved Roads.Step into a piece of Woodstock's storied past with this enchanting 1910 Arts & Crafts masterpiece, gracefully situated on nearly six bucolic acres along one of the town's most picturesque and sought-after roads.Originally owned by Jane BYRD Whitehead and Ralph RadCLIFFE Whitehead, two of the visionary founders of the

    John Kralik Compass Greater New York, LLC

    253 Upper Byrdcliffe Rd, Woodstock, NY 12498
  • /39

    $1,100,000

    • 3 Beds
    • 3.5 Baths
    • 2,337 Sq Ft

    94 the Middle Way, Mount Tremper, NY 12457

    Privately sited on a quiet back road in the Catskills, Noorden House is a modern retreat offering both seclusion and convenience—just 20 minutes to Woodstock, 15 to Phoenicia, and 30 to two ski mountains. Elevated on over 5 acres, the home enjoys distant mountain views, beautifully landscaped grounds, and serene natural features including a heated freeform pool, a small pond, and a picturesque

    Jennifer Grimes Country House Realty, Inc.

    94 the Middle Way, Mount Tremper, NY 12457
  • /39

    $1,100,000

    • 2 Beds
    • 2 Baths
    • 2,209 Sq Ft

    11 Louie Way, Woodstock, NY 12498

    A spectacular view of Bass Meadow and mountains is just one of the highpoints of this beautiful Cape Cod home on 6.1 acres located a few miles from Woodstock Village. From the home's wraparound stone patio and large windows, imagine looking out at a serene 70-acre vista of meadow and woods that is protected from development. This lovely, turnkey 2209-square-foot home features an open-plan living

    Gary Heckelman Halter Associates Realty Inc

    11 Louie Way, Woodstock, NY 12498
  • /31

    $1,099,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,252 Sq Ft

    32 Maurizi Ln, Woodstock, NY 12498

    Blending classic country charm with modern sophistication, this newly built modern farmhouse offers over 3,000 square feet of beautifully finished living space. Designed with clean lines, a neutral palette, and layered textures, it delivers a timeless aesthetic full of warmth and character. The home features four spacious bedrooms, three and a half baths, a fully finished lower level, and

    Richard Vizzini Corcoran Country Living

    32 Maurizi Ln, Woodstock, NY 12498
  • /15

    $540,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 1.5 Baths
    • 1,804 Sq Ft

    5 Violet Place, Woodstock, NY 12498

    Lovely 3-4 bedroom home located in a quiet, friendly neighborhood, just minutes from the shopping, dining, and arts in the village of Woodstock, and about 15 minutes to bustling Kingston and Saugerties. 12 minutes to Thruway, 15 minutes to Trailways bus in Kingston (5 minutes to Woodstock stop), 25 minutes to Rhinecliff Amtrak train station for car-free access to NYC. Upstairs you'll find 3

    Fawn Denue Keller Williams Hudson Valley

    5 Violet Place, Woodstock, NY 12498
  • /23

    $699,000

    • 3 Beds
    • 2 Baths
    • 1,212 Sq Ft

    424 John Joy Rd, Woodstock, NY 12498

    This Woodstock beauty is set on 1.6 private acres on the very desirable John Joy Road. Step into the gracious entry and first notice the abundant light streaming into the spacious living room from the large picture windows. There is a fireplace for cozy evenings at home which can be enjoyed from either the living area or the large dining area which currently seats 8 with room to spare. The

    Richard Stoll Halter Associates Realty

    424 John Joy Rd, Woodstock, NY 12498
  • /62

    $695,000

    • 4 Beds
    • 2 Baths
    • 1,550 Sq Ft

    12 Arnold Dr, Woodstock, NY 12498

    Located on a quiet, country road is this meticulously maintained raised ranch home with ample privacy. Enjoy nature in the many sitting areas in this beautifully landscaped yard with charming bluestone walkway and walls, and lovely shade trees. Upon entering the house the inviting tiled foyer takes you up to the first floor where the first thing you'll notice are those beautiful well cared for

    Rodney Batista Howard Hanna Rand Realty

    12 Arnold Dr, Woodstock, NY 12498
  • /33

    $729,000

    • 2 Beds
    • 2 Baths
    • 1,565 Sq Ft

    28 Pine Grove St, Woodstock, NY 12498

    Nestled in the heart of the Village of Woodstock, this enchanting cottage awaits your arrival. Just a block from exquisite restaurants and vibrant shopping, it graces an oversized corner lot, providing a sense of space in its beautifully landscaped, fully fenced yard.With two generous bedrooms and two full bathrooms, the home invites you into an extended living area that radiates warmth

    Sheena Lepez Compass Greater New York, LLC

    28 Pine Grove St, Woodstock, NY 12498
  • /74

    $2,950,000

    • 3 Beds
    • 3 Baths
    • 2,608 Sq Ft

    235 California Quarry Rd, Woodstock, NY 12498

    Architect-Designed Modern Retreat with Unparalleled Views Over WoodstockPerched high above the town of Woodstock, this rare and exceptional home offers a front-row seat to breathtaking panoramic views that stretch from the mountains to the Ashokan Reservoir. Designed by noted architect Les Walker, this contemporary residence evokes the magic of living in a luxurious treehouse—where every

    Ellen Osgood Coldwell Banker Village Green

    235 California Quarry Rd, Woodstock, NY 12498
  • /12

    $1,168,250

    • Land
    • 38 Acres
    • $31,054 per Acre

    33 Mamoud Hills Rd, Woodstock, NY 12401

    The Grand Estate at Mamoud HillsA Singular Offering of 37.62 Private Acres in the Catskills' Most Prestigious Hidden EnclaveLegacy has a location. This is it.Now offered as a complete estate assemblage, this extraordinary 37.62-acre landholding within the exclusive Mamoud Hills enclave is a rare opportunity in the heart of the Catskills. Comprising several contiguous,

    Cameron Ashkarkhizani Serhant LLC

    33 Mamoud Hills Rd, Woodstock, NY 12401
  • /8

    $277,550

    • Land
    • 8 Acres
    • $35,000 per Acre

    39 Mamoud Hills Rd, Kingston, NY 12401

    39 Mamoud Hills: The Art of Arrival7.93 Acres of Prepared, Private, and Inspired Land in the Catskills' Most Exclusive EnclaveDesign the life. Shape the land. Set the tone.At 39 Mamoud Hills, you are not simply buying 7.93 acres you're claiming your own corner of one of the Catskills' most prestigious private communities, just minutes from Woodstock. This is land that doesn't

    Cameron Ashkarkhizani Serhant LLC

    39 Mamoud Hills Rd, Kingston, NY 12401
  • /9

    $364,800

    • Land
    • 12 Acres
    • $30,000 per Acre

    40 Mamoud Hills Rd, Kingston, NY 12401

    Mamoud Hills: The Best-Kept Secret in the Catskills12.16 Acres of Elevated Potential in a Private Estate Community Minutes from WoodstockNot just land. Legacy.Tucked behind a gated, lamp-lit private road in the Catskills' most exclusive hideaway, this 12.16 acre estate parcel in Mamoud Hills is where architectural daydreams grow up and get built.Imagine: a long, tree-lined

    Cameron Ashkarkhizani Serhant LLC

    40 Mamoud Hills Rd, Kingston, NY 12401
  • /11

    $269,700

    • Land
    • 9 Acres
    • $30,000 per Acre

    41 Mamoud Hills Rd, Kingston, NY 12401

    Your Private Sanctuary in the Catskills' Elite Mamoud HillsDiscover a once-in-a-generation opportunity in the prestigious Mamoud Hills enclave, nestled in the luxury real estate market of the Catskills. Demonstrating the pinnacle of bespoke development potential, this over 8-acre parcel is woven into a secure private community just minutes from Woodstock, the ultimate destination for

    Cameron Ashkarkhizani Serhant LLC

    41 Mamoud Hills Rd, Kingston, NY 12401
  • /11

    $256,200

    • Land
    • 9 Acres
    • $30,000 per Acre

    21 Mamoud Hills Rd, Kingston, NY 12401

    Welcome to The Place Where Masterpieces Take Shape Tucked away in the serene embrace of the Catskills, this expansive parcel in the sought-after Mamoud Hills enclave offers more than just land—it offers a legacy. Set within a refined private community just minutes from the iconic hamlet of Woodstock, this over 8-acre homesite lies at the gateway to inspiration.A graceful

    Cameron Ashkarkhizani Serhant LLC

    21 Mamoud Hills Rd, Kingston, NY 12401
  • /64

    $1,900,000

    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    67 Cricket Ridge, Bearsville, NY 12409

    Welcome to Cricket Ridge Tower House, a Woodstock artists' mountaintop retreat with breathtaking views and meditative sculpture gardens located 5 minutes to the Village. Surrounded by spectacular perennial gardens, there is visual interest in all seasons with a chorus of beautiful and vibrant blooms throughout the warmer months. This home was built by and has served as inspiration for the owners,

    Amy Lonas Coldwell Banker Village Green

    67 Cricket Ridge, Bearsville, NY 12409
  • /44

    $525,000

    • 4 Beds
    • 2 Baths
    • 1,652 Sq Ft

    1502 Sawkill Rd, Kingston, NY 12401

    Nestled between the vibrant arts community of Woodstock and the historic charm of Kingston, this unique 2.13-acre property offers a rare opportunity to create your own riverside sanctuary along the serene Saw Kill Creek. The main residence is a 1,073-square-foot home featuring two bedrooms and one full bathroom. Oversized windows in the living room provide stunning views of the creek, allowing

    Savannah Miceli Century 21 Alliance-NP

    1502 Sawkill Rd, Kingston, NY 12401
  • /37

    $720,000

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft

    273 Grog Kill Rd, Willow, NY 12495

    Once in a while a listing comes along that offers buyers a unique opportunity for peaceful living with luxury finishes... At 273 Grog Kill Road, you have an opportunity to treat your home like a getaway experience. The design of this contemporary home blends with tranquil scenery. As you pull in the driveway, you are provided a detached one car garage, with additional driveway parking. Enjoy

    Jorge Lugo Real Broker NY LLC

    273 Grog Kill Rd, Willow, NY 12495
  • /62

    $825,000

    • 2 Beds
    • 1 Bath
    • 1,256 Sq Ft

    90 Aarons Way, Mount Tremper, NY 12457

    Tucked away at the end of a quiet private road near the top of Roundtop Mountain, this 2-bedroom, 1-bath home offers serene seclusion surrounded by protected DEP land and a private forest preserve. A true nature lover's paradise, the property is alive with wildlife and boasts beautifully landscaped grounds, seasonal mountain views, and the potential for year-round vistas with the clearing of

    Darlene Griffin Halter Associates Realty

    90 Aarons Way, Mount Tremper, NY 12457
  • /28

    $815,000

    • 2 Beds
    • 2 Baths
    • 1,416 Sq Ft

    2318 Glasco Turnpike, Woodstock, NY 12498

    This classic 1890s farmhouse marries period charm with high-end modern amenities in a natural setting. Bordered by quiet woodlands, meadows and a bluestone wall, the house stands out as a gem. A spacious living room, flooded with natural light, flows seamlessly into a large separate dining room featuring window benches looking onto an ample side deck-perfect for morning coffee bathed in sunrise.

    Jeannine Simmons Corcoran Country Living

    2318 Glasco Turnpike, Woodstock, NY 12498
  • /41

    $895,000

    • 5 Beds
    • 4 Baths
    • 2,426 Sq Ft

    8 Pine Grove St, Woodstock, NY 12498

    Discover a rare investment opportunity in the vibrant enclave of Woodstock, NY with this impeccably restored, easy-to-show 1920s farmhouse located just minutes from the bus to NYC and Woodstock's iconic dining, shops, galleries, and live music. Freshly painted, with a new roof, this proven income-generating property offers reclaimed wide-plank pine floors, exposed beams, and curated designer

    Gary Heckelman Halter Associates Realty

    8 Pine Grove St, Woodstock, NY 12498
  • /41

    $749,000

    • 2 Beds
    • 2 Baths
    • 1,208 Sq Ft

    18 Country Club Ln, Woodstock, NY 12498

    Stunning reimagined Ranch, just 1/2 Mile from the Center of Woodstock, 2/10 of a Mile to the NYC Bus Route,yet providing an excellent sense of privacy, and a perfect rural setting.Beautifully, and thoughtfully updated baths and kitchen, embracing the best of Modern Design principals and practicality.The perfect country escape, yet within easy access to restaurants, shopping and

    Margo Obourn Win Morrison Realty - W

    18 Country Club Ln, Woodstock, NY 12498
  • /8

    $289,000

    • Land
    • 10 Acres
    • $28,900 per Acre

    4912 New York 212, Willow, NY 12495

    Discover the opportunity to create your dream escape on this serene 10-acre parcel nestled in the quiet hamlet of Willow, NY. Tucked away in nature yet just a short drive from the vibrant village of Woodstock, this expansive property offers the perfect blend of privacy and proximity. Towering trees, dappled sunlight, and the calming sounds of nature create a peaceful setting for your future home,

    Richard Vizzini Corcoran Country Living

    4912 New York 212, Willow, NY 12495
  • /35

    $749,000

    • 2 Beds
    • 2 Baths
    • 1,868 Sq Ft

    1637 Glasco Turnpike, Woodstock, NY 12498

    Welcome to the Woodstock Retreat House.This exceptional multi-residential compound has been thoughtfully renovated to the highest standards and is fully furnished with a curated mix of vintage and contemporary pieces. A proven high-volume income producer, the property offers flexibility as a primary residence, part-time escape, or short-term rental investment.Set on 1.5 lush,

    Leslie Foti Coldwell Banker Village Green

    1637 Glasco Turnpike, Woodstock, NY 12498
  • /48

    $1,995,000

    • 2 Beds
    • 2 Baths
    • 1,531 Sq Ft

    128 Newcut Rd, Bearsville, NY 12409

    At the end of a private road and surrounded by forever-protected land, you'll find this serene 25-acre mountaintop escape—complete with an additional contiguous 10-acre buildable lot. Build your dream, expand your vision, or simply enjoy the privacy and open space. Breathtaking views, open meadows, and total seclusion create the perfect backdrop for peaceful living. The home itself is a

    Heidi Maloney Four Seasons Sotheby's Int'l R

    128 Newcut Rd, Bearsville, NY 12409

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