Woodstock, NY Homes

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  $1,195,000

  • 3 Beds
  • 4 Baths
  • 3,120 Sq Ft

  540 Mount Tobias Rd, Mount Tremper, NY 12457

  Step into the pages of Dwell magazine and immerse yourself in this architect-designed gem offering a harmonious blend of modern design and natural beauty. Feel a wave of calm wash over you, greeted by resplendent views, clean lines, and a wall of windows overlooking majestic mountain vistas. Modernists rejoice. Design aficionados delight. And nature enthusiasts revel. A minimalist aesthetic

  Alexander James Compass Greater NY, LLC

  540 Mount Tobias Rd, Mount Tremper, NY 12457
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  /53

  $4,900 per month

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft
  • House for Rent

  17 Cross Patch Rd, Willow, NY 12495

  Beautifully renovated farmhouse set on 4.65 private acres with seasonal mountain views. This fully furnished 3BR/2BA home features an open floor plan, custom kitchen with vaulted ceilings, high-end appliances, marble countertops, and hardwood floors throughout. Living room with cobblestone fireplace and French doors to covered porch. Screened porch and large back deck overlook lush grounds.

  Susanna Scott-Mitchell Compass Greater NY, LLC

  17 Cross Patch Rd, Willow, NY 12495
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  /25

  $770,000 Sold Mar 11, 2026

  86 Rock City Rd, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 1,754 Sq Ft
  • Built 1910

  Last Sold Summary

  • 7% Below List Price
  • $439/SF
  • 90 Days On Market

  Current Estimated Value $782,934

  Last Listing Agent Michael Shaughnessy Halter Associates Realty

  86 Rock City Rd, Woodstock, NY 12498
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  /24

  Est $776,989 Not Listed For Sale

  7 Lark Dr, Wood Stock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 1,345 Sq Ft
  • Built 2024

  7 Lark Dr, Wood Stock, NY 12498

  Last Sold Summary

  • 4% Above List Price
  • $554/SF
  • 37 Days On Market

  Last Sold Price $745,000

  Last Listing Agent Richard Vizzini Corcoran Country Living
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  /72

  $1,495,000

  • 3 Beds
  • 3 Baths
  • 2,566 Sq Ft

  1 Wittenberg Rd, Bearsville, NY 12409

  Welcome to Bearsville Record House, a landmark property with a legacy deeply rooted in American music. Originally built in 1873 and once home to famed Bearsville Records, this storied compound includes two dwellings; the main farmhouse and a guest cottage, plus a studio building waiting to be finished to your specs. A gunite saltwater pool, outdoor kitchen, and fenced-in plum orchard complete the

  Jessica Brasseur Houlihan Lawrence Millbrook Of

  1 Wittenberg Rd, Bearsville, NY 12409
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  /37

  $5,300 per month

  • 3 Beds
  • 2 Baths
  • 2,739 Sq Ft
  • House for Rent

  33 Race Track Rd, Bearsville, NY 12409

  ANNUAL FURNISHED RENTAL w POOL Lovely, meticulously maintained 3 bd/2 ba home with flex room and finished basement on amazing road. 3 plus bucolic acres minutes to the center of Woodstock HW floors, gourmet kitchen, living room with beautiful stone fireplace. Stone patio perfect for eating al fresco Sprawling grounds and gardens. Plenty of room to enjoy hosting family and friends.

  Johanna Trimboli Halter Associates Realty

  33 Race Track Rd, Bearsville, NY 12409
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  $1,150,000 Sold Aug 22, 2025

  11 Louie Way, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 2,209 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Above List Price
  • $521/SF
  • 31 Days On Market

  Last Listing Agent Gary Heckelman Halter Associates Realty Inc

  11 Louie Way, Woodstock, NY 12498
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  /35

  Est $1,695,646 Not Listed For Sale

  85 Baumgarten Rd, Woodstock, NY 12498

  • 7 Beds
  • 3.5 Baths
  • 4,582 Sq Ft
  • Built 1720

  85 Baumgarten Rd, Woodstock, NY 12498

  Last Sold Summary

  • $371/SF
  • 54 Days On Market

  Last Sold Price $1,700,000

  Last Listing Agent Anne Rajs Corcoran Country Living
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  /42

  $1,199,000

  • 4 Beds
  • 2 Baths
  • 3,378 Sq Ft

  3207-3209 New York 212, Bearsville, NY 12409

  Enchanting Woodstock Compound with a Craftsman Home, Cottage, and Historic Barn. Welcome to a truly rare offering in the heart of the Catskills, just minutes from the center of Woodstock, yet tucked away in a storybook setting of trees, meadows, and the soothing sounds of the Sawkill stream. This private 1.85-acre homestead compound blends rustic charm with modern versatility, featuring a

  Michelle Bergkamp William Pitt Sotheby's Interna

  3207-3209 New York 212, Bearsville, NY 12409
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  /14

  $4,000 per month

  • 4 Beds
  • 2 Baths
  • 2,158 Sq Ft
  • House for Rent

  295 Grog Kill Rd, Willow, NY 12495

  SHORT TERM RENTAL: Private, fully furnished Woodstock Oasis with mountain views, is ready to be your country getaway! On a dead-end rd. up high on a hill, this Willow home has everything you need, close to hiking, skiing, restaurants and shopping, just minutes from Woodstock, Phoenicia and the NYS Thruway, this private retreat is available beginning March 2026

  Mark Kanter BHHS HUDSON VALLEY PROP-WDST

  295 Grog Kill Rd, Willow, NY 12495
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  /38

  $620,000 Sold Sep 26, 2025

  3 Oriole Dr, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 2,158 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Above List Price
  • $287/SF
  • 32 Days On Market

  Current Estimated Value $615,912

  Last Listing Agent Mario Geissler Four Seasons Sotheby's Int'l R

  3 Oriole Dr, Woodstock, NY 12498
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  /20

  Not Listed For Sale

  TBD Jessop Rd, Woodstock, NY 12498

  TBD Jessop Rd, Woodstock, NY 12498

  Last Sold Summary

  • 65 Days On Market

  Last Sold Price $625,000

  Last Listing Agent Paula Chandler Past Member
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  /29

  $1,499,900

  • 3 Beds
  • 4 Baths
  • 3,330 Sq Ft

  106 Mountain Laurel Ln, Woodstock, NY 12498

  A truly one-of-a-kind residence and rare opportunity, this exceptional home offers a seamless blend of architecture and art in the heart of Woodstock, walking distance to Tinker Street, yet set privately on 1.73 secluded acres just minutes from the village.Designed as a fusion of a Frank Lloyd Wright–inspired contemporary addition and an original Buckminster Fuller–style geodesic dome, the

  Ashley Olson Minard eXp Realty

  106 Mountain Laurel Ln, Woodstock, NY 12498
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  /23

  $6,500 per month

  • 4 Beds
  • 2.5 Baths
  • 1,853 Sq Ft
  • House for Rent

  11 Shultis Farm Rd, Bearsville, NY 12409

  AVAIL FROM SEPT 2025. Private & Serene Modern Farmhouse Near Woodstock - Nestled on a private road just minutes from the heart of Woodstock, this beautifully renovated 4-bedroom, 2.5-bathroom modern farmhouse offers the perfect blend of charm, space, and privacy. Surrounded by mature trees, stone walls, and tall hedges, this home feels like a secluded retreat while remaining conveniently close to

  Alexis Li Corcoran Country Living

  11 Shultis Farm Rd, Bearsville, NY 12409
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  /43

  $2,700,000 Sold Jun 13, 2025

  2655 Glasco Turnpike, Woodstock, NY 12498

  • 4 Beds
  • 3 Baths
  • 3,390 Sq Ft
  • Built 1945

  Last Sold Summary

  • 16% Below List Price
  • $796/SF
  • 209 Days On Market

  Current Estimated Value $2,714,516

  Last Listing Agent Richard Vizzini Corcoran Country Living

  2655 Glasco Turnpike, Woodstock, NY 12498
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  /32

  Est $1,034,744 Not Listed For Sale

  185 John Joy Rd, Wood Stock, NY 12498

  • 3 Beds
  • 3 Baths
  • 2,258 Sq Ft
  • Built 2015

  185 John Joy Rd, Wood Stock, NY 12498

  Last Sold Summary

  • 9% Above List Price
  • $421/SF
  • 37 Days On Market

  Last Sold Price $950,000

  Last Listing Agent Sheena Lepez Compass Greater New York, LLC
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  /37

  $899,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  8 Tannery Brook Rd, Woodstock, NY 12498

  Large shade trees filter dappled sunlight across this property's private waterside retreat, where the ancient stone wall of the streambed tells the story of millennia, smoothed by the eternal passage of water. Just steps from the vibrant rhythm of Tinker Street and the creative heartbeat of Woodstock, this nearly 2,500 square foot mixed-use property is more than a home or an investment, it is a

  Laurie Ylvisaker Coldwell Banker Village Green

  8 Tannery Brook Rd, Woodstock, NY 12498
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  $16,500 per month

  • 4 Beds
  • 2.5 Baths
  • 2,394 Sq Ft
  • House for Rent

  75 Hill 99, Woodstock, NY 12498

  AVAIL FROM SEPT 2025. Secluded Mountain Chalet with Breathtaking Views and Poolside Lodge - Set atop nine private acres, this stunning mountaintop chalet offers a rare combination of serenity, seclusion, and spectacular views. A long, private driveway winds through the property, leading to a retreat unlike any other. The property features a three-story main house and a separate two-story Poolside

  Alexis Li Corcoran Country Living

  75 Hill 99, Woodstock, NY 12498
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  /28

  $257,000 Sold Feb 27, 2026

  259 Silver Hollow Rd, Willow, NY 12495

  • 1 Bath
  • 475 Sq Ft
  • Built 1950

  Last Sold Summary

  • 1% Below List Price
  • $541/SF
  • 58 Days On Market

  Current Estimated Value $259,519

  Last Listing Agent Leslie Foti Coldwell Banker Village Green

  259 Silver Hollow Rd, Willow, NY 12495
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  Not Listed For Sale

  0 Wittenberg Rd Unit KEYH6302035, Woodstock, NY 12498

  0 Wittenberg Rd Unit KEYH6302035, Woodstock, NY 12498

  Last Sold Summary

  • 64 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Sean Zimmerman Halter Associates Realty Inc
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  /11

  $499,000

  • Land
  • 15.23 Acres
  • $32,764 per Acre

  Tbd Wardwell Ln, Woodstock, NY 12498

  A rarely available large, 15+ acre parcel in Woodstock -- less than a mile from the center of town! Completely private yet moments away from restaurants, music venues, shops, golf course and hiking. A mixture of mature deciduous and conifer trees offer a forest haven, with level land, rock features and an elevated knoll building site, ready for your next chapter.Much of the heavy lifting has

  Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

  Tbd Wardwell Ln, Woodstock, NY 12498
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  $850,000 Sold May 08, 2025

  363 Cold Brook Rd, Bearsville, NY 12409

  • 3 Beds
  • 2 Baths
  • 3,126 Sq Ft
  • Built 1985

  Last Sold Summary

  • 23% Below List Price
  • $272/SF
  • 117 Days On Market

  Last Listing Agent Carol Spirig Halter Associates Realty Inc

  363 Cold Brook Rd, Bearsville, NY 12409
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  /24

  Not Listed For Sale

  18 Vandermark Rd, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft
  • Built 2024

  18 Vandermark Rd, Woodstock, NY 12498

  Last Sold Summary

  • $578/SF
  • 24 Days On Market

  Last Sold Price $549,000

  Last Listing Agent Zachary Jarvis BHHS Nutshell Realty
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  /34

  $650,000 Open Sat 12PM - 2PM

  • 2 Beds
  • 1 Bath
  • 1,436 Sq Ft

  117 Ohayo Mountain Rd, Woodstock, NY 12498

  Set against a backdrop of sweeping mountain views and quiet Woodstock landscape, this inviting country property offers a rare blend of charm, space, and opportunity. The main home features 2 bedrooms and 1 bath, with a warm, welcoming interior defined by original hardwood floors, rich wood-paneled walls, and a classic wood-burning fireplace that anchors the living room. A bluestone enclosed porch

  Donna Brooks Compass Greater NY, LLC

  117 Ohayo Mountain Rd, Woodstock, NY 12498
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  /40

  $1,055,000 Sold Aug 20, 2025

  10 Magnolia Trail, Woodstock, NY 12498

  • 4 Beds
  • 3 Baths
  • 2,613 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Below List Price
  • $404/SF
  • 34 Days On Market

  Last Listing Agent Joseph Satto Fresh Air Realty

  10 Magnolia Trail, Woodstock, NY 12498
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  /35

  Not Listed For Sale

  162 Van Dale Rd Unit 170, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 2,299 Sq Ft
  • Built 1925

  162 Van Dale Rd Unit 170, Woodstock, NY 12498

  Last Sold Summary

  • $298/SF
  • 80 Days On Market

  Last Sold Price $685,000

  Last Listing Agent Jeannine Simmons Corcoran Country Living
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  /42

  $599,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 1,939 Sq Ft

  83 Ratterman Rd, Woodstock, NY 12498

  It's a WINNER! This is truly a wonderful house in an excellent location! Surrounded by trees with a quiet, rural feel, yet walking distance to the Village of Woodstock, it's everything a Woodstock buyer is looking for! From the moment you step up to this charmer, you'll be welcomed by a wide, impressive Bluestone walkway to the Bluestone front porch where you can envision many peaceful hours

  Edwin Maldonado Howard Hanna Rand Realty

  83 Ratterman Rd, Woodstock, NY 12498
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  /42

  $967,500 Sold Dec 05, 2025

  241 Silver Hollow Rd, Willow, NY 12495

  • 3 Beds
  • 2.5 Baths
  • 1,932 Sq Ft
  • Built 1963

  Last Sold Summary

  • 3% Below List Price
  • $501/SF
  • 47 Days On Market

  Current Estimated Value $974,480

  Last Listing Agent Carol Spirig Halter Associates Realty

  241 Silver Hollow Rd, Willow, NY 12495
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  /28

  Not Listed For Sale

  16 Deming St, Woodstock, NY 12498

  • 4 Beds
  • 1 Bath
  • 1,794 Sq Ft
  • Built 1930

  16 Deming St, Woodstock, NY 12498

  Last Sold Summary

  • $284/SF
  • 111 Days On Market

  Last Sold Price $510,000

  Last Listing Agent Toby Ress Win Morrison Realty - W
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  /14

  $399,000

  • 1 Bed
  • 1 Bath
  • 841 Sq Ft

  57 Ohayo Mountain Rd, Woodstock, NY 12498

  BACK ON THE MARKET! BUYER FINANCING FELL THROUGH All the charm and convenience of Woodstock village living! Adorable period bungalow moments from the center of Woodstock! This 1 BR, 1 BA charmer features an additional room/four-season sunroom, handsome masonry fireplace with wood stove and a river rock chimney, modern kitchen, a clawfoot tub, separate laundry area, and is nestled in a wooded,

  Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

  57 Ohayo Mountain Rd, Woodstock, NY 12498
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  $810,000 Sold Oct 24, 2025

  11 Grogkill Rd, Willow, NY 12495

  • 3 Beds
  • 2.5 Baths
  • 3,080 Sq Ft
  • Built 2006

  Last Sold Summary

  • 42% Below List Price
  • $263/SF
  • 78 Days On Market

  Current Estimated Value $1,097,612

  Last Listing Agent Sharon Breslau BHHS Hudson Valley Properties

  11 Grogkill Rd, Willow, NY 12495
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  Not Listed For Sale

  15 Silver Wings Ln, Woodstock, NY 12498

  • 4 Beds
  • 6.5 Baths
  • 3,746 Sq Ft
  • Built 1900

  15 Silver Wings Ln, Woodstock, NY 12498

  Last Sold Summary

  • $360/SF
  • 58 Days On Market

  Last Sold Price $1,350,000

  Last Listing Agent Hailey Kiesewetter Upstate Down
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  /15

  $575,000

  • Land
  • 37 Acres
  • $15,541 per Acre

  00 Lauren Ct, Woodstock, NY 12498

  This spectacular 35+ acre property is a rare offering. Comprised of two separate lots with access points on both Lauren Ct and Church Rd - an open canvas for your boldest vision. Whether you're a developer seeking your next signature project or a homeowner dreaming of a private sanctuary, this land invites imagination and promises possibility. A harmonious blend of mature woodlands, sunlit

  Melissa Zoe Hirsch Coldwell Banker Village Green

  00 Lauren Ct, Woodstock, NY 12498
• 

  $607,000 Sold Jan 23, 2026

  18 Niles Dr, Woodstock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • Built 1965

  Last Sold Summary

  • 11% Above List Price
  • $305/SF
  • 29 Days On Market

  Current Estimated Value $568,653

  Last Listing Agent Laurel Sweeney BHHS Nutshell Realty

  18 Niles Dr, Woodstock, NY 12498
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  /35

  Not Listed For Sale

  2292 Glasco Turnpike, Woodstock, NY 12498

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft
  • Built 1924

  2292 Glasco Turnpike, Woodstock, NY 12498

  Last Sold Summary

  • $352/SF
  • 7 Days On Market

  Last Sold Price $1,010,000

  Last Listing Agent Daniel Romero Compass Greater New York, LLC
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  /24

  $2,400,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,420 Sq Ft

  420 Wittenberg Rd, Bearsville, NY 12409

  Woodstock Custom Compound - Create your own private family compound on 2.437 serene acres in the Woodstock Hamlet of Wittenberg--an exceptional to-be-built offering that brings together architectural vision, artisan materials, and the craftsmanship of noted builder James Nelson. This unique project includes a three-bedroom, three-and-a-half-bath main residence, a one-bedroom guest house, and a

  Peter Cantine Halter Associates Realty

  420 Wittenberg Rd, Bearsville, NY 12409
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  /39

  $585,000 Sold Sep 12, 2025

  148 Hutchin Hill Rd, Shady, NY 12409

  • 2 Beds
  • 1 Bath
  • 1,039 Sq Ft
  • Built 1949

  Last Sold Summary

  • 2% Below List Price
  • $563/SF
  • 76 Days On Market

  Current Estimated Value $579,336

  Last Listing Agent Mario Geissler Four Seasons Sotheby's Int'l R

  148 Hutchin Hill Rd, Shady, NY 12409
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  /34

  Est $823,853 Not Listed For Sale

  5249 Route 212, Mount Tremper, NY 12457

  • 4 Beds
  • 3 Baths
  • 2,201 Sq Ft
  • Built 1990

  5249 Route 212, Mount Tremper, NY 12457

  Last Sold Summary

  • 23% Above List Price
  • $304/SF
  • 63 Days On Market

  Last Sold Price $669,000

  Last Listing Agent Hillary Kolos Compass Greater NY, LLC
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  /10

  $125,000

  • Land
  • 0.58 Acre
  • $215,517 per Acre

  5485 New York 212, Shandaken, NY 12480

  CAUTION ! The garage on the property has previously caught fire .Must be torn down .DO NOT ENTER THE GARAGE Prime Catskills Land Listing - HB Commercial/Residential ZoningPerfectly positioned in the heart of the Catskills, this 1⁄2+ acre parcel offers dream-worthy mountain views and unbeatable access to the region's most sought-after outdoor attractions. Whether you're planning a

  Stephanie Berryann United Real Estate HV Edge

  5485 New York 212, Shandaken, NY 12480
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  /31

  $978,000 Sold Apr 21, 2025

  38 Vandebogart Rd, Woodstock, NY 12498

  • 4 Beds
  • 3.5 Baths
  • 3,914 Sq Ft
  • Built 1920

  Last Sold Summary

  • 3% Above List Price
  • $250/SF
  • 12 Days On Market

  Current Estimated Value $981,813

  Last Listing Agent Alexis Li Corcoran Country Living

  38 Vandebogart Rd, Woodstock, NY 12498

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