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Homes for Sale in 12529

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  • /33

    $1,398,000

    • 3 Beds
    • 3 Baths
    • 2,366 Sq Ft

    63 Knapp Hollow Ln, Hillsdale, NY 12529

    Where Nature and Serenity Take Center Stage!At the end of a private road, a magical country retreat awaits. Offered with two lots totaling over 10 acres, this secluded sanctuary brings together tranquility, natural beauty, and privacy.A winding gravel drive leads to the home, framed by colorful gardens and two picturesque ponds. A stone pathway meanders through vibrant flowers and

    Martin Salerno The Kinderhook Group, Inc.

    63 Knapp Hollow Ln, Hillsdale, NY 12529
  • /43

    $649,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    261 Yonderview Rd, Copake, NY 12516

    Nestled on 3.36 serene acres near the New York-Massachusetts line, this completely renovated ranch-style home is a stunning blend of modern elegance and rural charm. Spanning 1,600 square feet, the open floor plan invites you into a sleek kitchen that boasts contemporary cabinetry, a spacious center island, stainless steel appliances, and luxurious quartz countertops, making it a dream for any

    Barbara Robinson Red Apple Realty Inc

    261 Yonderview Rd, Copake, NY 12516
  • /30

    $995,000

    • 3 Beds
    • 2 Baths
    • 1,890 Sq Ft

    2227 New York 23, Hillsdale, NY 12529

    COUNTRY CONTEMPORARY RANCH ON 9.5 ACRES WITH FOREVER WILD VIEWSA truly special country getaway, this distinctive 3-bedroom, 2-bath contemporary home is set on 9.5 beautiful acres with sweeping views of protected farmland and forever-wild Audubon sanctuary lands. Designed to embrace its natural surroundings, the home enjoys southern exposure and passive solar orientation, creating a warm

    Theresa Westlake Copake Lake Realty Corp.

    2227 New York 23, Hillsdale, NY 12529
  • /38

    $879,000

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

    310 Pine Ridge Ln, Hillsdale, NY 12529

    Located on a quiet country cul-de-sac in Hillsdale, this spacious three-bedroom home sits on 4.7 private acres. One of just three residences along the road, it enjoys an exceptionally peaceful setting, with open lawn, well-maintained woods, trails, and old stone walls.Inside, the living space provides generously proportioned rooms and abundant natural light. The living room centers around

    THEADORA VENGRIN Corcoran Country Living

    310 Pine Ridge Ln, Hillsdale, NY 12529
  • /66

    $1,300,000

    • 4 Beds
    • 3.5 Baths
    • 3,115 Sq Ft

    351 Dugway Rd, Austerlitz, NY 12017

    Welcome to Bons Reves House, a beautifully designed escape tucked away on nearly seven acres in the most desirable part of the Austerlitz hills. Built in 1985 and meticulously renovated and expanded by a top builder in 2012 and again in 2025, this 4-bedroom, 3.5-bath contemporary home feels like a luxury treehouse hidden among mature hardwoods and surrounded by large estates and high-end

    Anthony D'Argenzio Houlihan Lawrence Inc.

    351 Dugway Rd, Austerlitz, NY 12017
  • /30

    $575,000

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

    416 Whippoorwill Rd, Hillsdale, NY 12529

    PRIVATE SETTING!! Cape Cod style home, built in 2000, 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 additional living space.Ideally located on one of Hillsdale's

    Margaret Bower Avenia Columbia County RE Specialist

    416 Whippoorwill Rd, Hillsdale, NY 12529
  • /52

    $21,000,000

    • 5 Beds
    • 5.5 Baths
    • 5,203 Sq Ft

    21 Schoolhouse Rd, Hillsdale, NY 12529

    There are beautiful homes in the Hudson Valley, and then there are properties that seem to occupy a world entirely their own. Set at one of the most extraordinary vantage points in the region, this exceptional contemporary estate presides over 135 private acres with sweeping, unobstructed views across the Hudson Valley to the Catskill Mountains. The sense of scale is remarkable: open sky, rolling

    Nikki Carchedi STONE HOUSE PROPERTIES, LLC

    21 Schoolhouse Rd, Hillsdale, NY 12529
  • /68

    $649,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    261 Yonderview Rd, Hillsdale, NY 12529

    Nestled on 3.36 serene acres near the New York-Massachusetts line, this completely renovated ranch-style home is a stunning blend of modern elegance and rural charm. Spanning 1,600 square feet, the open floor plan invites you into a sleek kitchen that boasts contemporary cabinetry, a spacious center island, stainless steel appliances, and luxurious quartz countertops, making it a dream for any

    Barbara Robinson Red Apple Realty

    261 Yonderview Rd, Hillsdale, NY 12529
  • /36

    $729,900

    • 3 Beds
    • 2.5 Baths
    • 1,834 Sq Ft

    417 Overlook Dr, Hillsdale, NY 12529

    Discover Your Dream Cape-Style Home: A Serene Escape on 2.1 AcresNestled 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

    Barbara Robinson Red Apple Realty Inc

    417 Overlook Dr, Hillsdale, NY 12529
  • /38

    $650,000

    New Construction $45K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    30 Ridge Ln, Hillsdale, NY 12529

    Offering privacy, quality construction, and an ideal location. Set in the heart of the Roe-Jan region of the Hudson Valley and at the edge of the Berkshires, this home is tucked privately among mature trees on nearly eight acres while remaining close to the center of town.Recently constructed by one of the region's top builders, the residence was designed with both quality and longevity in

    John Barbato Compass, Hillsdale

    30 Ridge Ln, Hillsdale, NY 12529
  • /35

    $620,000

    • 3 Beds
    • 2 Baths
    • 2,932 Sq Ft

    33 Twin Bridges Rd, Copake, NY 12516

    Welcome to this charming country home set along a quiet rural road in Copake. Bright, comfortable living spaces and a peaceful setting surrounded by mature trees and open lawn create an atmosphere that feels instantly relaxing. The open living area brings together the updated kitchen, dining room, and living room anchored by a brick fireplace—perfect for cozy evenings.French doors open to a

    Agent Photo

    Brad Rebillard

    DUTCHESS COUNTRY REALTY INC. M

    33 Twin Bridges Rd, Copake, NY 12516
  • /20

    $795,000

    • Land
    • 50.5 Acres
    • $15,743 per Acre

    0 Rd Unit 20264993, Hillsdale, NY 12529

    A short 5 minute drive from the Taconic State Parkway, tucked up on a mountainside with incredible far-reaching panoramic views of the Catskills and the Hudson Valley. Untouched and unencumbered, this former farmland has no archaeological issues or no endangered species. Stone walls and gentle slopes. Ready for building. Divided into 5 lots of varying sizes. Sell off the lots one by one, or keep

    John Barbato Compass, Hillsdale

    0 Rd Unit 20264993, Hillsdale, NY 12529
  • /9

    $85,000

    • Land
    • 11.09 Acres
    • $7,665 per Acre

    0 Ny 22 Unit 20264890, Hillsdale, NY 12529

    So many possibilities for this 11 acre parcel on Route 22. Approximately 240 feet of road frontage provides options for a driveway up hill to flat land and eastern views The property is currently wooded. The upper land had been cleared over 30 years ago. Use this property to build your home or for hunting. Close to The Berkshires, Great Barrington

    Peter Newman Beach & Bartolo Realtors

    0 Ny 22 Unit 20264890, Hillsdale, NY 12529
  • /59

    $3,300,000

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

    124 Syre Ln, Hillsdale, NY 12529

    PRIVATE & QUIET ~ 124 Syre Lane, Hillsdale NY Federal 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 Avenia COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC

    124 Syre Ln, Hillsdale, NY 12529
  • /28

    $499,900

    • 2 Beds
    • 2 Baths
    • 1,362 Sq Ft

    9165 New York 22, Copake, NY 12516

    This one has character. Real bones, real charm, the kind of property you can't fake. Wood construction, green metal roof, mature pines creating actual privacy on your own acre.2020 renovation means the systems work: all-electric, mini splits, two bath. Two bedrooms, a potential third first floor primary or office set up, with a very flexible layout.First-time buyer who wants

    Daniel Mahar Mahar Real Estate, LLC

    9165 New York 22, Copake, NY 12516
  • /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
  • /36

    $698,000

    $51K PRICE DROP
    • 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
  • /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

    Agent Photo

    Sabrina Puppolo

    Corcoran Country Living

    3493 County Route 7, Hillsdale, NY 12529
  • /19

    $299,888

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 736 Sq Ft

    81 SW Colony Rd, Hillsdale, NY 12529

    PRICE REDUCTION - Under 300,000 dollars on Copake Lake! Welcome to 81 SW Colony Road, a charming 2-bedroom, 1-bath bungalow now offered at a newly adjusted price point that makes owning a piece of Columbia County paradise more accessible than ever. Experience the quintessential upstate lifestyle just over two hours from New York City and 30 minutes from both the Hudson and Wassaic train

    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
  • /48

    $725,000

    $70K PRICE DROP
    • 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

    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
  • /7

    $75,000

    $20K PRICE DROP
    • Land
    • 12.95 Acres
    • $5,792 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
  • /12

    $75,000

    $20K PRICE DROP
    • Land
    • 6.25 Acres
    • $12,000 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

    $849,900

    $150K 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

    Jason Walch Coldwell Banker Advisor Realty

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

    $849,900

    $150K 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

    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
  • /13

    $815,000

    $35K PRICE DROP
    • Land
    • 19.7 Acres
    • $41,371 per Acre

    2 Ridge Ln, Hillsdale, NY 12529

    Shangri - LaOff 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

    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

    $275,000

    $50K PRICE DROP
    • Land
    • 22.84 Acres
    • $12,040 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

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