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Homes for Sale in 12529

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  • /13

    $325,000

    • Land
    • 24.4 Acres
    • $13,320 per Acre

    120 Dugway Rd, Hillsdale, NY 12529

    If the home you dream of building includes a private setting, on a hill that's surrounded by nature, and valuable infrastructure already in place, then this is the land for you. The lot is 24.40 acres of beautiful, mostly wooded land with a cleared one-acre meadow BUILD SITE that is located high on the hill and far from the road. There's a roughed-in DRIVEWAY that starts at the road with a bridge

    Jeffrey McKinney Beach & Bartolo Realtors

    120 Dugway Rd, Hillsdale, NY 12529
  • /58

    $3,300,000

    • 4 Beds
    • 3 Baths
    • 5,760 Sq Ft

    124 Syre Ln, Hillsdale, NY 12529

    PRIVATE & QUIET ~ 124 Syre Lane, Hillsdale NYFederal Style Colonial home in Hillsdale, perched on the top of the mountain, pairing historical accuracy with state-of-the-art modern conveniences. This stately country home offers unparalleled, endless views in every direction of the valley and Catskill Mountains. Offering Immeasurable beauty, from every window and large back deck, perfect for

    Margaret Bower Avenia Columbia County RE Specialist

    124 Syre Ln, Hillsdale, NY 12529
  • /75

    $290,000

    • Land
    • 40.25 Acres
    • $7,205 per Acre

    0 Anthony St Unit LotWP001, Copake, NY 12529

    Located within the Town of Hillsdale itself, this unique 40.25 acre offering presents a rare opportunity to own a sizable tract of land in one of Columbia County's most desirable communities. While the property enjoys immediate access to the restaurants, shops, services, and amenities that make Hillsdale such a sought-after destination, its layout and surrounding landscape create a surprisingly

    Mitchell Serlin Whitetail Properties Real Estate

    0 Anthony St Unit LotWP001, Copake, NY 12529
  • /19

    $392,500

    • 2 Beds
    • 2 Baths
    • 1,494 Sq Ft

    155 Pumpkin Hollow Rd N, Hillsdale, NY 12529

    Colonial Home on a Beautiful Country Parcel with New Garage Nestled on a peaceful country road, this charming two-bedroom Colonial offers the perfect blend of privacy, comfort, and convenience. Set back from the road on a beautiful parcel, the home welcomes you into a bright, open-concept living and dining area filled with natural light and complemented by attractive hardwood floors. The

    Jonathan Scarinzi Elyse Harney Real Estate

    155 Pumpkin Hollow Rd N, Hillsdale, NY 12529
  • /66

    $290,000

    • Land
    • 40.25 Acres
    • $7,205 per Acre

    00WTP Anthony St, Hillsdale, NY 12529

    Located within the Town of Hillsdale itself, this unique 40.25± acre offering presents a rare opportunity to own a sizable tract of land in one of Columbia County's most desirable communities. While the property enjoys immediate access to the restaurants, shops, services, and amenities that make Hillsdale such a sought-after destination, its layout and surrounding landscape create a surprisingly

    Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

    00WTP Anthony St, Hillsdale, NY 12529
  • /24

    $675,000

    • Land
    • 9.57 Acres
    • $70,533 per Acre

    109-Lot 4 Lake Ridge Ln, Copake Lake, NY 12521

    The Ridge at Copake Lake is a gated private road of 11 ready-to-build lots nestled in the lush landscape of an untouched mountain top. Each designated building site has been artfully tailored to visually isolate one home from another. Access the waterfront from your individually appointed boat slip on the 99ft of private water frontage owned by the Association. A special opportunity to enjoy lake

    John Barbato Compass, Hillsdale

    109-Lot 4 Lake Ridge Ln, Copake Lake, NY 12521
  • /26

    $650,000

    • Land
    • 10.55 Acres
    • $61,611 per Acre

    162-Lot 10 Lake Ridge Ln, Copake Lake, NY 12521

    The Ridge at Copake Lake is a gated private road of 11 ready-to-build lots nestled in the lush landscape of an untouched mountain top. Each designated building site has been artfully tailored to visually isolate one home from another. A special opportunity to enjoy lake living within a uniquely private setting. The 10+ acres of Lot 10 embrace direct views of the Taconic mountains to the east.

    John Barbato Compass, Hillsdale

    162-Lot 10 Lake Ridge Ln, Copake Lake, NY 12521
  • /28

    $474,900

    Open Sat 2PM - 4PM
    • 3 Beds
    • 1.5 Baths
    • 1,912 Sq Ft

    41 Cold Water St, Hillsdale, NY 12529

    OPEN HOUSE - (Saturday) August 8 from 2-4 p.m. The Edward Herrington House, circa 1886 - 1898 is one of the historic homes in thecharming hamlet of Hillsdale, New York. A multi-century-old sugar maple greets you as you enter this quaint Hamlet Historic District home. This spacious 3-bedroom, 1.5 bathroom heritage residence takes you back in time with its many original details while providing

    Ramona Bellamy Copake Lake Realty Corp.

    41 Cold Water St, Hillsdale, NY 12529
  • /36

    $749,000

    • 3 Beds
    • 2 Baths
    • 2,040 Sq Ft

    695 Wolf Hill Rd, Hillsdale, NY 12529

    This country home is nestled on 8.7 private acres just five miles from the center of Hillsdale, this charming retreat offers the perfect blend of comfort, character, and natural beauty. A meandering driveway winds through the woods, leading to a welcoming cottage-style home surrounded by perennial gardens filled with native ferns and plantings.The inviting covered front porch opens to a

    Kimberly Baker BHHS Hudson Valley Properties

    695 Wolf Hill Rd, Hillsdale, NY 12529
  • /33

    $890,000

    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft

    49 Knapp Hollow Ln, Hillsdale, NY 12529

    On 5 park-like acres this well maintained and thoughtfully designed home overlooks a tranquil pond and offers a serene getaway. Designed by architect Dennis Wedlick to maximize space and ease of living the home features 3-4 bedrooms and 3 full baths of which one is a separate guest suite. A renovated kitchen and updated bathrooms blend seamlessly with gleaming wood floors. A striking double sided

    marylou Kersten COPAKE LAKE REALTY CORP.

    49 Knapp Hollow Ln, Hillsdale, NY 12529
  • /36

    $650,000

    • 3 Beds
    • 2.5 Baths
    • 1,977 Sq Ft

    3493 County Route 7, Hillsdale, NY 12529

    Escape to your own private retreat where lake living, outdoor adventure, and timeless country charm come together! Just steps from scenic Copake Lake, this property offers access to one of Columbia County's premier recreational destinations. The 410-acre, motorboat-friendly lake is perfect for boating, waterskiing, kayaking, paddleboarding, and excellent fishing, while nearby Copake Country Club

    Agent Photo

    Sabrina Puppolo

    Corcoran Country Living

    3493 County Route 7, Hillsdale, NY 12529
  • /51

    $729,900

    • 3 Beds
    • 2.5 Baths
    • 2,210 Sq Ft

    417 Overlook Dr, Hillsdale, NY 12529

    Discover Your Dream Cape-Style Home: A Serene Escape on 2.1 Acres Nestled in a tranquil setting, this stunning Cape-style home offers the perfect blend of comfort and luxury, with 2.1 acres of nature at your doorstep. Imagine sipping your morning coffee on the spacious front porch while listening to the gentle rustle of leaves around you. Step inside to an inviting and dramatic living room, where

    Barbara Robinson Red Apple Realty

    417 Overlook Dr, Hillsdale, NY 12529
  • /19

    $325,000

    • 2 Beds
    • 1 Bath
    • 736 Sq Ft

    81 SW Colony Rd, Hillsdale, NY 12529

    Welcome to THE UPSTATE RETREAT--where every day feels like a vacation on Copake Lake, the largest lake in Columbia County, spanning approximately 425 acres. Whether you're searching for the perfect weekend escape, a summer lake house, or a year-round getaway, this charming 2-bedroom, 1-bath bungalow offers the quintessential upstate lifestyle just over two hours from New York City. Beyond the

    Agent Photo

    Mark Saxby

    Berkshire Hathaway HomeService

    81 SW Colony Rd, Hillsdale, NY 12529
  • /22

    $365,000

    • 1 Bed
    • 1 Bath
    • 684 Sq Ft

    251 Overlook Dr, Hillsdale, NY 12529

    Are you dreaming of times spent tucked away in a rustic cabin, preferably wrapped in a cozy blanket in front of a roaring fireplace? Or maybe you're dreaming of barefoot in the stream that feds into the Green River and sunbathing with rays of sunshine beaming through the trees? Welcome to 251 Overlook, Hillsdale NY! Cira 1900 Cottage in the woods, built on the side of a mountain, on 4.5 Acres. A

    Margaret Bower Avenia Columbia County RE Specialist

    251 Overlook Dr, Hillsdale, NY 12529
  • /43

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    65 Meadow Ln, Hillsdale, NY 12529

    With a view as far as the eye can see, 65 Meadow Lane, Hillsdale never fails to amaze from sunrise to sunset, as a full moon lights up your bedroom; hawks fly past wandering clouds, the fiery yellow and burnt red leaves of autumn and the pine trees dripping with snow like confectionary sugar in a winter wonderland. The only sounds you hear are woodpeckers and wild turkeys and your heartbeat

    Margaret Bower Avenia Columbia County RE Specialist

    65 Meadow Ln, Hillsdale, NY 12529
  • /44

    $1,485,000

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

    51 Taconic Creek Rd, Hillsdale, NY 12529

    This perfect modern farmhouse retreat is tucked away on one of Columbia County's most quiet and beautiful roads guaranteeing a tranquil respite from the city. Being one of just a handful of properties on the road creates a sense of peace and quiet that is unmatched. While a feeling of simplicity emanates throughout the land there is a clear level of sophistication in the design details. The

    Thomas Pawlowski Four Seasons Sotheby's Int.

    51 Taconic Creek Rd, Hillsdale, NY 12529
  • /7

    $39,900

    • Land
    • 26,571 Sq Ft
    • $65,410 per Acre

    0 Prach Road Extension Unit 20263433, Claverack, NY 12513

    Take advantage of this opportunity to build your dream home on this cleared, flat, .61 acre parcel (with well on property). Conveniently located just minutes to Hudson's restaurants, shops, and Amtrak station, or if you prefer outdoor activities e.g. hiking, kayaking, skiing, and ariel adventure, it's all within a short drive to Bash Bish Falls State Park, Copake Lake, and Catamount Mountain

    Wendy Kenney Davala Real Estate, LLC

    0 Prach Road Extension Unit 20263433, Claverack, NY 12513
  • /33

    $389,000

    • 4 Beds
    • 1 Bath
    • 2,229 Sq Ft

    1953 County Road 11, Claverack, NY 12513

    Step into a home that feels like it has been quietly telling its story since the 1800's, where every beam and board carries the charm of a bygone era. This classic colonial residence preserves its original character with exposed beams stretching across the main floor and a layout that balances simplicity with purpose. The kitchen is modest yet functional, anchored by a traditional wood store that

    Karen Davala Davala Real Estate, LLC

    1953 County Road 11, Claverack, NY 12513
  • /7

    $95,000

    • Land
    • 12.95 Acres
    • $7,336 per Acre

    00 Stone Ledge Rd, Hillsdale, NY 12529

    Quiet location next to the Berkshires. Dead end road with a 12 acre parcel. Hiking trails throughout. Glorious views off the top. Great value. More land available.

    Tracy Tassinari Gabel Real Estate

    00 Stone Ledge Rd, Hillsdale, NY 12529
  • /25

    $995,000

    • 2 Beds
    • 2 Baths
    • 2,060 Sq Ft

    17 Memory Ln, Hillsdale, NY 12529

    Lakefront living in one of the most peaceful and serene locations on Copake Lake. An expansive 75 feet of private waterfront with an existing dock, this charming home offers beautiful eastern views across the lake, where sunrises and tranquil water vistas become part of everyday life.The home's inviting open-concept layout has a spacious kitchen, dining, and living area. A first-floor primary

    John Barbato Compass, Hillsdale

    17 Memory Ln, Hillsdale, NY 12529
  • /12

    $95,000

    • Land
    • 6.25 Acres
    • $15,200 per Acre

    0 Stone Ledge Rd, Hillsdale, NY 12529

    Quiet parcel with a small cabin and a shed. Shed with loft area and porch. Nestled on a dead end road in Hillsdale. Cleared paths with trails. Quiet location close to MA. Great value.

    Tracy Tassinari Gabel Real Estate

    0 Stone Ledge Rd, Hillsdale, NY 12529
  • /50

    $949,900

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    2955 State Route 23, Hillsdale, NY 12529

    Steeped in Hillsdale’s rich history, this extraordinary property began its life as one of the area’s original grist mills, situated in the area of Hillsdale once known as Murray’s Corner. Thoughtfully transformed over the years into a distinctive residence, it seamlessly blends historic character with the tranquility of a private country retreat. Set on 8.7 enchanting acres, the property feels as

    Jason Walch Coldwell Banker Advisor Realty

    2955 State Route 23, Hillsdale, NY 12529
  • /58

    $949,900

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    2955 New York 23, Hillsdale, NY 12529

    Steeped in Hillsdale's rich history, this extraordinary property began its life as one of the area's original grist mills, situated in the area of Hillsdale once known as Murray's Corner. Thoughtfully transformed over the years into a distinctive residence, it seamlessly blends historic character with the tranquility of a private country retreat. Set on 8.7 enchanting acres, the property feels as

    Jason Walch Coldwell Banker Advisor Realty

    2955 New York 23, Hillsdale, NY 12529
  • /5

    $225,000

    • Land
    • 6 Acres
    • $37,500 per Acre

    L135.2 Rockledge Rd, Hillsdale, NY 12529

    Escape to your own private sanctuary in the heart of Columbia County's coveted Hudson Valley. This 6 acre wooded parcel on scenic Rockledge Road offers the perfect canvas for your dream retreat, with mature trees providing natural privacy and a peaceful, secluded setting that feels worlds away from the everyday. Ideally situated in the Town of Hillsdale -- one of the region's most sought-after

    Agent Photo

    Jamie Mazuryk

    Venture Fox Realty Group LLC

    L135.2 Rockledge Rd, Hillsdale, NY 12529
  • /31

    $349,900

    • 4 Beds
    • 2 Baths
    • 2,080 Sq Ft

    9161 Ny-22, Copake, NY 12516

    Just minutes from the center of Hillsdale, Roe Jan Park, and the Harlem Valley Rail Trail, this split-level ranch offers a convenient location with easy access to some of the area's most popular outdoor and community amenities. The 2,080-square-foot home features four bedrooms and two bathrooms, providing a practical layout with space for everyday living. A bright sunroom serves as a natural

    Paige Backhaus William Raveis Real Estate

    9161 Ny-22, Copake, NY 12516
  • /5

    $399,000

    • Land
    • 12.18 Acres
    • $32,759 per Acre

    3551 County Rd 7, Copake, NY 12516

    A true beauty! Discover the perfect setting for your dream home on this stunning 12.18-acre parcel featuring mostly open, sprawling fields and breathtaking distant countryside views. With ample space for a private estate, hobby farm, gardens, or recreational enjoyment, this picturesque property offers the ideal blend of rural tranquility and convenient access to area amenities.Enjoy a prime

    Theresa Westlake Copake Lake Realty Corp.

    3551 County Rd 7, Copake, NY 12516
  • /48

    $3,600,000

    $250K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,083 Sq Ft

    335 Dawson Rd, Hillsdale, NY 12529

    Presiding over 27 acres of rolling hills, meadows, and dramatic mountain views, Southview Farm is a fully reimagined country estate in the heart of Hillsdale farm country. Once part of a 300-acre dairy farm with a grand farmhouse on this site for over a century, the property has been expanded and rebuilt from the ground up to deliver modern luxury, efficiency, and comfort while honoring its

    Norah Burden Brown Harris Stevens HV LLC

    335 Dawson Rd, Hillsdale, NY 12529
  • /12

    $850,000

    • Land
    • 19.7 Acres
    • $43,147 per Acre

    2 Ridge Ln, Hillsdale, NY 12529

    Shangri - La Off of Overlook Drive, on Ridge Lane a harmonious, breathtakingly beautiful 19 acre property with outstanding views over rolling pastures, distant hills and the Catskill Mountains; privacy and peace pervade. A dirt drive gently curves around a lovely pond and through the woods landing in a high clearing and perfect building site. BOHA approved. For an interested buyer, a stunning

    Nicole Vidor Nicole Vidor Real Estate Inc.

    2 Ridge Ln, Hillsdale, NY 12529
  • /5

    $259,000

    • Land
    • 15.47 Acres
    • $16,742 per Acre

    191 Berkshire Rd, Hillsdale, NY 12529

    Discover the perfect opportunity to build your dream home on this expansive 15.47-acre parcel at 191 Berkshire Road, bordering Copake Country Club and just minutes from Copake Lake. This fully undeveloped property is part of the desirable Sam Hill Road community, offering shared waterfront access through the HOA. Ideally located just 25 minutes from Hudson and Great Barrington, MA, you'll enjoy

    Austin Urban Venture Fox Realty Group

    191 Berkshire Rd, Hillsdale, NY 12529
  • /55

    $1,525,000

    • 4 Beds
    • 4.5 Baths
    • 3,666 Sq Ft

    83 Schmeichel Rd, Hillsdale, NY 12529

    Custom contemporary home built in 1996 with thoughtful gathering spaces. Main floor has a vaulted ceiling living room with fireplace, open to dining and the eat-in-kitchen. Down a hall to the south end there is the primary suite, a powder room, laundry, the den with a vaulted ceiling and a woodstove and access to the garage. On the north side of the main living room is a large entry foyer, a

    Jennifer Harvey Compass Greater NY LLC

    83 Schmeichel Rd, Hillsdale, NY 12529
  • /41

    $2,195,000

    • 3 Beds
    • 3 Baths
    • 2,755 Sq Ft

    292 White Hill Rd, Hillsdale, NY 12529

    Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side captures the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    292 White Hill Rd, Hillsdale, NY 12529
  • /20

    $299,000

    $26K PRICE DROP
    • Land
    • 22.84 Acres
    • $13,091 per Acre

    0 County Route 21, Hillsdale, NY 12529

    Welcome to DREAMLAND.Set along a quiet country road, this exceptional 22 acre parcel offers the rare combination of privacy, curated natural beauty, and effortless access from New York City. Just minutes from the Taconic State Parkway, the property is ideally positioned for seamless weekend escapes or full-time living. A sun-drenched open meadow--perfectly oriented for southern

    Pamela King-Belfor Four Seasons Sotheby's Int.

    0 County Route 21, Hillsdale, NY 12529
  • /54

    $1,100,000

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

    2666 New York 23, Hillsdale, NY 12529

    Unique investment opportunity in the hamlet of Hillsdale. This new-to-the-market commercial/residential property has been meticulously renovated by the current owner, a commercial builder, who over-engineered the project with high-end features throughout. The property consists of four distinct rental units:2666 Route 23, Main (Blue) Building- First-Floor Commercial Unit Right Side: 360

    Margaret Bower Avenia Columbia County RE Specialist

    2666 New York 23, Hillsdale, NY 12529
  • /42

    $900,000

    $200K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,495 Sq Ft

    309 Pine Ridge Ln, Hillsdale, NY 12529

    Nestled on a wooded hillside on one of Hillsdale's prettiest country roads is where you will discover this exceptional 2,500 sq.ft. custom-built home. The 5.5-acre parcel sits above Pine Ridge Lane; a lightly travelled country road located just off Mitchell Street in the heart of Hillsdale. Surrounded by nature in every direction, the peaceful, park-like setting is unique and as beautiful as any

    Margaret Bower Avenia Columbia County RE Specialist

    309 Pine Ridge Ln, Hillsdale, NY 12529
  • /31

    $725,000

    Open Sat 10AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 2,225 Sq Ft

    2999 New York 23, Hillsdale, NY 12529

    2999 Route 23, Hillsdale, New York - Historic Country Estate on 12.5 Acres Step into a piece of living history with this beautifully preserved 1915 home, perfectly situated on a private 12.5-acre parcel in the heart of the Berkshires. Offering four generous bedrooms and three baths (2 full, 1 Half), this classic residence blends timeless charm with everyday comfort, creating an ideal setting for

    Tyler Bervy Stone House Properties, LLC

    2999 New York 23, Hillsdale, NY 12529
  • /30

    $619,000

    $30K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    416 Whippoorwill Rd, Hillsdale, NY 12529

    This one checks all of the boxes. Our newly listed two bedroom, two bath Cape Cod style home in Hillsdale has been meticulously maintained and is in excellent condition inside and out. The main level features a functional kitchen, dining area, bathroom, and living room centered around a propane fireplace; all with hardwood floors. A 12x12 great room with hardwood floors was added to provide

    Margaret Bower Avenia Columbia County RE Specialist

    416 Whippoorwill Rd, Hillsdale, NY 12529
  • /34

    $649,000

    $70K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,475 Sq Ft

    81 Black Grocery Rd, Hillsdale, NY 12529

    On a quiet country road, sit's the prettiest sunshine yellow house you've ever seen.Welcome to a property where outdoor splendor and indoor comfort merge seamlessly, where everything has been taken care of, and all you need to do is arrive and exhale. Rolling hills and open farmland stretch out before you, and they're all yours to enjoy.Inside, the dining room flows into an open kitchen

    Shaina Marron Houlihan Lawrence Inc.

    81 Black Grocery Rd, Hillsdale, NY 12529
  • /19

    $850,000

    • Land
    • 150 Acres
    • $5,667 per Acre

    0 Overlook Dr, Hillsdale, NY 12529

    Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with

    MATTHEW CAREY Rouse + Co Real Estate

    0 Overlook Dr, Hillsdale, NY 12529
  • /19

    $850,000

    • Land
    • 150 Acres
    • $5,667 per Acre

    400 Overlook Dr, Hillsdale, NY 12529

    Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with

    MATTHEW CAREY Rouse + Co Real Estate

    400 Overlook Dr, Hillsdale, NY 12529
  • /6

    $3,490,000

    • 3 Beds
    • 4 Baths
    • 7,571 Sq Ft

    351 Lakeview Rd, Craryville, NY 12521

    Welcome to Mickey's Marina, a rare waterfront opportunity located at 351 Lakeview Road. Set along the shoreline with beautiful lake views, this unique property blends recreation, income potential, and lifestyle in one exceptional offering. The marina features direct water access with multiple boat slips, making it an ideal destination for boating enthusiasts and seasonal visitors alike. With its

    Austin Urban Venture Fox Realty Group

    351 Lakeview Rd, Craryville, NY 12521

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