153

Homes for Sale near Reginald Bennett Elementary School

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  • /42

    $375,000

    $24K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,044 Sq Ft

    7375 New York 28, Shandaken, NY 12480

    MOUNTAIN VIEWS & GUARANTEED INCOME: The Ultimate Catskills Duplex! Unlock the best of the Catskills at 7375 Route 28! Whether you are looking for a high-performing investment, a savvy ''house hack,'' or a sprawling single-family retreat, this property delivers. Built in 1950, this charming residence radiates a warm Catskills cottage vibe, featuring 4 bedrooms, 2 baths, and approximately 2,044

    Katherine Keys The Catskill Dream Team

    7375 New York 28, Shandaken, NY 12480
  • /47

    $1,525,000

    • 3 Beds
    • 2.5 Baths
    • 3,030 Sq Ft

    457 Krumville Rd, Olivebridge, NY 12461

    Tucked into a dramatic rock ridge with sweeping views of the Catskill Mountains, this renovated farmhouse invites you to slow down and savor country living at its finest. Spanning just over 3,000 square feet, the home balances rustic character with thoughtful modern updates throughout. The renovated kitchen, anchored by warm butcher block counters, flows gracefully into a generous dining room.

    Anna Barcone BHHS Nutshell Realty

    457 Krumville Rd, Olivebridge, NY 12461
  • /30

    $349,000

    • 4 Beds
    • 2 Baths
    • 1,403 Sq Ft

    169 New York 42, Shandaken, NY 12480

    Discover the potential of this hidden gem, privately set back from the road on a spacious, level front yard. This four-bedroom ranch-style home offers the convenience of single-level living and is ready for a complete transformation. Inside, you'll find a welcoming living room featuring beautiful wood floors, a bluestone fireplace, and soaring cathedral ceilings. A breezeway with a bluestone

    Siobhan Scanlan Win Morrison Realty-K

    169 New York 42, Shandaken, NY 12480
  • /2

    $100,000

    • Land
    • 7.3 Acres
    • $13,699 per Acre

    1 Friendship Manor Rd, Pine Hill, NY 12465

    The land contains 7.3 acres and has three predrilled wells with with a reported capacity of ~80 gpm. The well was drilled in 274 feet of bedrock and a 72-hour pumping test was performed to determine the sustainable capacity.

    Thomas Dolan

    1 Friendship Manor Rd, Pine Hill, NY 12465
  • /18

    $799,000

    $99K PRICE DROP
    • Land
    • 27.19 Acres
    • $29,386 per Acre

    TBD MacDaniel Rd, Bearsville, NY 12409

    Pollinator's Pathway in Woodstock Discover 27+ acres of untouched beauty just steps from the Tibetan Monastery, Magic Meadow, and the trailheads to Meads Mountain and Overlook Mountain. A private, winding ~.5-mile driveway opens to a sunlit clearing alive with wildflowers and pollinator plants — a natural canvas awaiting your vision. With selective tree trimming, sweeping Catskill Mountain views

    Genevieve Geaney Compass Greater New York, LLC

    TBD MacDaniel Rd, Bearsville, NY 12409
  • /7

    $495,000

    • Land
    • 15 Acres
    • $33,000 per Acre

    256 MacDaniel Rd, Bearsville, NY 12409

    Rare opportunity to create your dream home on a magical piece of property! Private/ quiet road, yet minutes from the center of the town of Woodstock, with all it has to offer! Potential majestic mountain views, with clearing. A dirt road leading up to the property is already in place. This 15 acre parcel of land is located on one of the Woodstock area's most coveted roads. The Karma Triyana

    Corinne Gervai Coldwell Banker Village Green

    256 MacDaniel Rd, Bearsville, NY 12409
  • /50

    $849,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,485 Sq Ft

    18 Jomar Ln, Olivebridge, NY 12461

    You'll understand just how special this 41 Acre property is once you arrive. Just driving down the country road to get here is already a treat. Situated at the base of the majestic High Point Mountain you'll find a private driveway that takes you through a beautiful forest and then it opens up to acres of your own open farmlands.....the open fields are perfectly suited to horses and with an

    Edwin Maldonado Howard Hanna Rand Realty

    18 Jomar Ln, Olivebridge, NY 12461
  • /17

    $99,900

    $50K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 672 Sq Ft

    244 Upper Samsonville Rd, Olivebridge, NY 12461

    Perfect 1 acre Catskill Mountain property with old mobile home in need of total rehabilitation. No well or septic on site. No existing heat source.

    Timothy Ayers Berardi Realty

    244 Upper Samsonville Rd, Olivebridge, NY 12461
  • /27

    $975,000

    • 3 Beds
    • 1.5 Baths
    • 394 Sq Ft

    938 Woodland Valley Rd, Phoenicia, NY 12464

    This unique and lavishly landscaped 14-acre property features visual privacy and extensive mountain views. It is replete with flowering shrubs, perennial borders, charming pathways through hidden gardens, an eight-foot-deep, surface acre swimming, boating, and fishing pond, and a labyrinth! Your ready-to-build three bedroom approved homesite is fully equipted with electric, septic, telephone,

    Derek Greene Greene Realty Group

    938 Woodland Valley Rd, Phoenicia, NY 12464
  • /53

    $849,000

    • 3 Beds
    • 2 Baths
    • 1,485 Sq Ft

    18 Jomar Ln, Olivebridge, NY 12461

    You'll understand just how special this 41 Acre property is once you arrive. Just driving down the country road to get here is already a treat. Situated at the base of the majestic High Point Mountain you'll find a private driveway that takes you through a beautiful forest and then it opens up to acres of your own open farmlands.....the open fields are perfectly suited to horses and with an

    Edwin Maldonado Howard Hanna Rand Realty

    18 Jomar Ln, Olivebridge, NY 12461
  • /51

    $2,400,000

    • 2 Beds
    • 2 Baths
    • 1,654 Sq Ft

    262 MacDaniel Rd, Bearsville, NY 12409

    Wend up your forested driveway to this idyllic piece of paradise -- 12 secluded acres, just minutes from Woodstock Village. The current owner/architect/builder designed this uniquely curated home and its surroundings to create the penultimate natural setting. As the house is revealed through the trees, a mirror image is reflected in the 13' deep, swimmable, mini-lake. BREATHE! That's the perfect

    Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

    262 MacDaniel Rd, Bearsville, NY 12409
  • /17

    $1,995,000

    • 8 Beds
    • 10 Baths
    • 12,393 Sq Ft

    20 Country Club Ln, Wood Stock, NY 12498

    Experience the legacy of Woodstock through this extraordinary historic offering. Once home to the iconic Woodstock Lodge and The Pinecrest, this storied 6.5-acre property offers a unique opportunity to reimagine a legacy estate in one of the Hudson Valley's most sought-after destinations. Set on scenic, gently rolling land with a blend of open clearings, wooded trails, and a seasonal stream, the

    Kathryn Johnson William Pitt Sothebys Int Rlty

    20 Country Club Ln, Wood Stock, NY 12498
  • /24

    $375,000

    • Land
    • 25 Acres
    • $15,000 per Acre

    101 Stone Rd, West Hurley, NY 12491

    Located in the heart of the beautiful Hudson Valley, this remarkable 25-acre woodland retreat offers a rare blend of natural beauty, privacy, and history. A thoughtfully engineered driveway winds through mature trees and dramatic rock outcroppings, crossing rugged gorges carved into the landscape and leading to a choice of two exceptional building sites, or the opportunity to create a primary

    Michael Tellerday Houlihan Lawrence Inc.

    101 Stone Rd, West Hurley, NY 12491
  • /8

    $69,000

    $10K PRICE DROP
    • Land
    • 33,976 Sq Ft
    • $88,462 per Acre

    0 Deerfield Rd Unit 20254253, Boiceville, NY 12412

    Rare lot in Boiceville with sewer connection available. This is a lightly wooded lot on a quiet dead end street but yet walking distance to Onteora High School, local supermarket, bus route, pharmacy, liquor store and Convenient Mart Gas Station and the Boiceville Rail Trail. Come take a look. The lot is near the end of the dead end so rarely any traffic. Boiceville has a lot to offer in this

    Siobhan Scanlan Win Morrison Realty-K

    0 Deerfield Rd Unit 20254253, Boiceville, NY 12412
  • /5

    $159,888

    $40K PRICE DROP
    • Land
    • 2.04 Acres
    • $78,376 per Acre

    515 Acorn Hill Rd, Olivebridge, NY 12461

    OLIVEBRIDGE, NY 12461 ULSTER COUNTY...Rare Turn-Key Development Opportunity in the Heart of the Catskills – Olive, NY GREAT FOR BUILDERS, DEVELOPERS & SAVVY INVESTORS!!!!! • Addresses: 515 & 517 Acorn Hill Rd, Olive, NY 12461. This prime offering features 2.04 acres of beautiful, usable land in a highly desirable residential area of the Catskills..... There are two uninhabitable mobile homes on

    Joseph Lombardo Listing by Lombardo Homes & Estates

    515 Acorn Hill Rd, Olivebridge, NY 12461
  • /44

    $1,325,000

    $250K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,360 Sq Ft

    94 Chestnut Hill Rd, Woodstock, NY 12498

    A rare opportunity to own a truly special piece of the Hudson Valley. Nestled in the heart of Woodstock, NY, this iconic property offers 11.17 breathtaking acres of open meadows and sweeping mountain views that change beautifully with every season. The well-maintained 3-bedroom, 1-bath ranch house spans 1,360 square feet and offers comfortable single-level living with a warm, classic character. A

    Henry Ford Coldwell Banker Village Green

    94 Chestnut Hill Rd, Woodstock, NY 12498
  • /19

    $799,000

    $60K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,562 Sq Ft

    2323 Glasco Turnpike, Woodstock, NY 12498

    A rare Byrdcliffe Colony offering, this 1911 Woodstock artist home sits just off Lower Byrdcliffe Road on a private half-acre of garden, lawn, patio, and woods. Rich with history and creative spirit, the original structure features the classic north-facing artist's window designed for painter's light, along with original beams and woodwork that speak to the home's early 20th-century

    Mark Kanter BHHS HUDSON VALLEY PROP-WDST

    2323 Glasco Turnpike, Woodstock, NY 12498
  • /30

    $1,599,000

    • 4 Beds
    • 6 Baths
    • 5,300 Sq Ft

    110 Lost Clove Rd, Big Indian, NY 12410

    Welcome to Lost Clove Mountain House, a rare and remarkable Catskills retreat set along a quiet country road in Big Indian. Surrounded by nearly nine private, wooded acres and bordered by protected state land, this fully renovated estate offers over 5,300 square feet of refined mountain living, where privacy, nature, and thoughtful design come together seamlessly. Just across the road, a mountain

    Brock Anderson Four Seasons Sotheby's Int.

    110 Lost Clove Rd, Big Indian, NY 12410
  • /50

    $868,000

    $60K PRICE DROP
    • 9 Beds
    • 3.5 Baths
    • 3,755 Sq Ft

    18 Barley Rd, Big Indian, NY 12410

    Set on 5.7 private acres in the heart of the Belleayre Mountains, this historic estate known as “Bella Vista” offers a rare blend of character, scale, and opportunity. Originally built in 1890 and thoughtfully updated over time, the residence features 9 bedrooms and 3.5 baths across approximately 3,755 square feet.The home showcases expansive living spaces, high ceilings, hardwood flooring,

    Jana Bangova LAFFEY REAL ESTATE

    18 Barley Rd, Big Indian, NY 12410
  • /51

    $495,000

    • Land
    • 5 Acres
    • $99,000 per Acre

    0 Yerry Hill Rd, Woodstock, NY 12498

    Tucked away just minutes from the heart of Woodstock, this exceptional 5-acre parcel offers a rare opportunity to create something truly special in one of the Hudson Valley's most sought-after locations. Surrounded by mature woods and natural beauty, the property features the serene Little Beaver Kill winding through the land along with seasonal mountain views from the upper elevation, creating

    Eliana Amodio Amodio Real Estate & Prop

    0 Yerry Hill Rd, Woodstock, NY 12498
  • /52

    $848,000

    • 3 Beds
    • 2 Baths
    • 1,764 Sq Ft

    1311 Wittenberg Rd, Mount Tremper, NY 12457

    Set well back from the road behind a handsome gated entry, this modern Catskills hideaway delivers the privacy everyone wants and the volume everyone hopes for. The approach is long and quiet; the house reveals itself slowly--wrapped by trees, with sky above and room to breathe on 4.04 acres. Inside, an airy great room rises with high ceilings and broad windows that pull in daylight and treetops.

    WINTON MORRISON Win Morrison Realty - W

    1311 Wittenberg Rd, Mount Tremper, NY 12457
  • /24

    $495,000

    • 3 Beds
    • 1.5 Baths
    • 1,310 Sq Ft

    198 Spillway Rd, West Hurley, NY 12491

    Nestled in the heart of the Catskills, this charming Cape Cod home sits on generous land and delivers the perfect blend of classic appeal and modern flexibility: three bedrooms, one and a half baths, beautiful hardwood floors, and a thoughtful layout ideal for comfortable year-round living or effortless weekend escapes.An accessory dwelling unit apartment on the property provides outstanding

    James Angelakis BHHS HUDSON VALLEY PROP-WDST

    198 Spillway Rd, West Hurley, NY 12491
  • /42

    $799,900

    $195K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,316 Sq Ft

    5 Maverick Terrace, Woodstock, NY 12498

    Tucked away on a peaceful, wooded lane, this inviting home offers the perfect blend of privacy, space, and convenience- just minutes to the heart of Woodstock. Inside, the home opens to an expansive living room anchored by a beautiful brick fireplace, creating a warm and inviting centerpiece for gatherings or quiet evenings. This oversized space includes a full bathroom and flows effortlessly to

    Dominique Musialkiewicz Howard Hanna Rand Realty

    5 Maverick Terrace, Woodstock, NY 12498
  • /72

    $900,000

    • 4 Beds
    • 2 Baths
    • 2,380 Sq Ft

    317 New York 375, West Hurley, NY 12491

    OPEN HOUSE MAY 31!!! 11:00 to 2:00First time on market in over 37 years! This historic 1840's Farmhouse offers the rustic charm of yesteryear only 5 minutes to the Village of Woodstock. Brimming with personality this home offers 4 bedrooms and 2 full baths set on over 2 idyllic acres. A welcoming feeling immediately takes over when you walk up the bluestone stairs and onto the front steps.

    Scott Helsmoortel Helsmoortel Realty Inc.

    317 New York 375, West Hurley, NY 12491
  • /34

    $530,000

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

    2013 County Road 3, Olivebridge, NY 12461

    Nestled among the trees and tucked back from the road, this immaculate Olivebridge retreat offers the kind of peace and privacy people move upstate for. Quiet, serene, and thoughtfully updated throughout, the property feels effortlessly welcoming from the moment you arrive. Inside, the home feels bright, comfortable, and incredibly well cared for. Sun pours through the windows, the wood stove

    Davina Thomasula Four Seasons Sothebys Intl

    2013 County Road 3, Olivebridge, NY 12461
  • /21

    $625,000

    • 5 Beds
    • 3 Baths
    • 1,620 Sq Ft

    16 Moggre Rd, Chichester, NY 12416

    Completely renovated & rebuilt modular ranch home with 5 bedrooms, 3 full bathrooms and open concept. From the modern kitchen to the elegant new bathrooms, this home has it all. Outside you have a large composite deck that overlooks the private 1.1 acres with patio and firepit. Close to Belleayre, Hunter and Windham Mountains. The home can come fully furnished for the right price. Currently being

    Jamie Sittner Find Advisors

    16 Moggre Rd, Chichester, NY 12416
  • /43

    $1,300,000

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

    5327 New York 212, Mount Tremper, NY 12457

    The Pines | Mt Tremper, New York A rare chance to steward one of the Catskills' most storied properties has quietly arrived. The Pines -- a cherished roadside inn and restaurant nestled between Woodstock and Phoenicia -- is ready for its next chapter. With more than five decades as a beloved Italian restaurant followed by a decade-long reinvention as a community gathering place, The Pines carries

    Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST

    5327 New York 212, Mount Tremper, NY 12457
  • /38

    $1,475,000

    • Land
    • 25.38 Acres
    • $58,117 per Acre

    132 Valley View Way, Woodstock, NY 12448

    The Ledges at Valley View High above the Beaverkill River, where the Catskills unfold in a sweep of peaks and light, lies The Ledges at Valley View - a design-ready estate site where modern architecture meets the mountain. Sited on more than 25 private acres, this south-facing ridgeline property captures cinematic views of Twin, Indian Head, Overlook, and Mount Guardian. The land adjoins more

    Margaret Bellar The Catskill Dream Team

    132 Valley View Way, Woodstock, NY 12448
  • /12

    $225,000

    $25K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,120 Sq Ft

    10 B Holland Dr, West Hurley, NY 12491

    Discover comfort and convenience in this charming two-story unit in Hurley, just minutes from the heart of Woodstock. Featuring 3 spacious bedrooms and 1.5 baths, this home offers the perfect blend of functionality and style. The open kitchen flows seamlessly into the dining area and features a cozy eat-in space with a slider door that leads directly to the patio--perfect for indoor-outdoor

    Ronnie Rebis Grist Mill Real Estate

    10 B Holland Dr, West Hurley, NY 12491
  • /24

    $375,000

    • Land
    • 25 Acres
    • $15,000 per Acre

    101 Stone Rd, Hurley, NY 12443

    Located in the heart of the beautiful Hudson Valley, this remarkable 25-acre woodland retreat offers a rare blend of natural beauty, privacy, and history. A thoughtfully engineered driveway winds through mature trees and dramatic rock outcroppings, crossing rugged gorges carved into the landscape and leading to a choice of two exceptional building sites, or the opportunity to create a primary

    Michael Tellerday Houlihan Lawrence, Inc.

    101 Stone Rd, Hurley, NY 12443
  • /42

    $1,925,000

    • 4 Beds
    • 3.5 Baths
    • 4,134 Sq Ft

    147 Bristol Hill Rd, Glenford, NY 12433

    Ever-changing light rises from the Ashokan Reservoir and travels uphill, casting its spell across this elegantly designed contemporary colonial on 4 acres. The home's construction reflects an uncommon commitment to quality. Built well beyond code requirements, it is framed with kiln-dried Douglas fir, insulated to exceptional standards, and fitted throughout with argon-filled, double-paned

    Laurie Ylvisaker Coldwell Banker Village Green

    147 Bristol Hill Rd, Glenford, NY 12433
  • /61

    $730,000

    $45K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,410 Sq Ft

    15 Lake View Dr, Lake Hill, NY 12448

    Own this stunning, architect-designed contemporary home in Woodstock, NY. Professionally decorated and thoughtfully crafted with passive solar principles, this energy-efficient residence seamlessly blends modern design with its natural surroundings. Set just across the road from the famous Cooper Lake, the home is nestled in a beautiful, 3 acre wooded setting—private yet not isolated—surrounded

    Mackenzie Grate The Machree Group, LLC

    15 Lake View Dr, Lake Hill, NY 12448
  • /15

    $169,900

    • Land
    • 1.4 Acres
    • $121,357 per Acre

    TBD Bristol Hill Rd, Glenford, NY 12433

    This buildable lot on Bristol Hill Road offers a peaceful Catskill neighborhood setting with wooded surroundings, privacy, and easy access to Woodstock and Kingston. Located in an R1 residential zoning district, the property provides an opportunity to create a full-time residence or weekend retreat surrounded by quiet roads, outdoor recreation, and classic Catskills charm.

    Ronin Ingwersen Berardi Realty

    TBD Bristol Hill Rd, Glenford, NY 12433
  • /70

    $3,600,000

    • 4 Beds
    • 4 Baths
    • 5,272 Sq Ft

    306 Meads Mountain Rd, Woodstock, NY 12498

    Inside Swoop House there is a versatile floor plan that includes four en suite bedrooms, one an attached guest suite, and two two-story great rooms, one of which was designed as a professional art studio. Designed by FT Architecture & Interiors and inspired by the Diller Scofidio Slow House, two non-parallel curved walls and sloping ceilings create a graceful series of shapes. This singular

    Kimberly Cantine Halter Associates Realty

    306 Meads Mountain Rd, Woodstock, NY 12498
  • /53

    $1,149,000

    $100K PRICE DROP
    • 4 Beds
    • 3 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
  • /31

    $2,300,000

    $200K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 2,978 Sq Ft

    177 Tinker St, Woodstock, NY 12498

    Fall in love with this artfully reimagined and expanded 1930 farmhouse, privately set on a gentle hill just moments from the heart of Woodstock. Rich in history and character, this special home was once owned by Michael Lang, the legendary founder of the 1969 Woodstock Festival—adding a rare and meaningful connection to the town's iconic past.Thoughtfully renovated, the home offers a

    Joan Capria Four Seasons Sotheby's Int'l R

    177 Tinker St, Woodstock, NY 12498
  • /12

    $58,000

    • Land
    • 1.1 Acres
    • $52,727 per Acre

    0 Blueberry Hill Rd, Olive, NY 12461

    Tucked away at the end of a quiet dead-end road, this 1.1-acre property offers a rare opportunity to create your own Catskills retreat in the heart of West Shokan. Hidden from view and bordered by forest, the land feels wonderfully secluded while remaining just minutes from everyday conveniences. A year-round stream winds through the property, adding the peaceful sound of moving water and a true

    Megan Avery Listing by Keller Williams Upstate NY Properties

    0 Blueberry Hill Rd, Olive, NY 12461
  • /32

    $569,000

    • 3 Beds
    • 1.5 Baths
    • 1,754 Sq Ft

    11 Mary Lou Ln, Shokan, NY 12481

    Move right into this beautifully maintained country home, thoughtfully designed with a modern open concept floor plan that is ideal for both comfortable everyday living and effortless entertaining. The custom kitchen features rich cherry cabinetry, quartz countertops which seamlessly flows into the dining area, where sliding glass doors open to a spacious deck, as well as the inviting living room

    Sharon Farley Corcoran Country Living

    11 Mary Lou Ln, Shokan, NY 12481
  • /19

    $752,000

    $33K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,194 Sq Ft

    12 Mountain Valley Rd, Boiceville, NY 12412

    Nestled on the hills of Mountain Valley you will find this one of a kind uniquely designed and engineered by the original owner. The home is fully documented in both words and illustrations and was created in a model. The home includes two bedrooms, two full baths, two car garage. In the basement you will find 2 areas which was used for tools and the other for creative space. Continuing through

    Robyn Awand Country Connections

    12 Mountain Valley Rd, Boiceville, NY 12412
  • /20

    $299,000

    • Land
    • 9.04 Acres
    • $33,061 per Acre

    000 Upper Samsonville Rd, Krumville, NY 12461

    Build your ideal country retreat or year-round home on this beautiful 9-acre property in the coveted Upper Samsonville Road area of Olivebridge, featuring a 200-foot roughed-in driveway and striking views of High Point Mountain. Bordered by original stone walls this buildable property offers multiple potential home sites with privacy. With a survey on record (Lot #13), completed and partial

    Amy Owens Coldwell Banker Village Green

    000 Upper Samsonville Rd, Krumville, NY 12461

Showing Results 81 - 120, Page 3 of 4

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