Chester, NY Homes

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  $730,000

  • 4 Beds
  • 3.5 Baths
  • 2,780 Sq Ft

  7 Park Place, Chester, NY 10918

  Welcome to your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional

  

  Luanne McGann

  Century 21 Full Service Realty

  (845) 447-0221

  7 Park Place, Chester, NY 10918
• Explore Chester

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  /20

  $12,040 per month

  • 7 Beds
  • 6 Baths
  • Condo for Rent

  45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

  The advertised rate of $12,041/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 7, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918
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  $43,000 Sold Oct 31, 2025

  L17 Vanderwalker Rd, Chester, NY 12817

  • Land
  • 4 Acres
  • $10,750 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 5 Days On Market

  Last Listing Agent Zachary Layton Four Seasons Sotheby's International Realty

  L17 Vanderwalker Rd, Chester, NY 12817
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  Est $191,621 Not Listed For Sale

  495 Laroe Rd, Chester, NY 10918

  495 Laroe Rd, Chester, NY 10918

  Last Sold Summary

  • 14% Above List Price
  • 170 Days On Market

  Last Sold Price $168,000

  Last Listing Agent Dylan Piazza Howard Hanna Rand Realty
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  $299,999 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  4508 Whispering Hills, Chester, NY 10918

  Welcome to 4508 Whispering Hills, a well-maintained and thoughtfully updated 2-bedroom, 1.5-bath home offering comfort and convenience. Recent upgrades include an updated kitchen and bathrooms, hardwood floors, a newer sliding glass door, garage door with opener, and an upgraded furnace, providing peace of mind for the next owner. The home features a one-car garage and a practical layout that

  

  Ammar Iqbal

  eXp Realty

  (845) 668-4564

  4508 Whispering Hills, Chester, NY 10918
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  $1,750 per month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  204 Pine Hollow Way, Chester, NY 10918

  Highly desirable one bedroom apartment for rent! Spacious open concept unit with lots of natural light! Relax on your own private patio and enjoy the peaceful surroundings of the outdoors. Large bedroom with great closet space! This unit has a private laundry room with hook ups. Close to all shopping, restaurants, apple picking, wineries, breweries & everything the beautiful Hudson Valley has to

  Kristie Jacques Century 21 Full Service Realty

  204 Pine Hollow Way, Chester, NY 10918
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  $320,000 Sold Mar 11, 2026

  2912 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Above List Price
  • $295/SF
  • 19 Days On Market

  Current Estimated Value $302,500

  Last Listing Agent Rebecca Matta-Candela Keller Williams Realty

  2912 Whispering Hills, Chester, NY 10918
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  Not Listed For Sale

  303 Sugarloaf Mountain Rd, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 2,287 Sq Ft
  • Built 2024

  303 Sugarloaf Mountain Rd, Chester, NY 10918

  Last Sold Summary

  • $306/SF
  • 35 Days On Market

  Last Sold Price $700,000

  Last Listing Agent Courtney Tablante Keller Williams Realty
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  $509,999 Pending

  • 2 Beds
  • 2 Baths
  • 1,714 Sq Ft

  391 Bull Mill Rd, Chester, NY 10918

  Motivated Seller!! Welcome home to this storybook setting, where a majestic weeping cherry blossom greets you with it's graceful cascade of blossoms each spring. This beautifully preserved historical farmhouse set on 1.7 acres along a scenic country road just down the lane from a local farm where the soft "mooing" adds to the peaceful rural charm. Sitting pretty on a corner lot with a circular

  

  Alexandra Zinko

  Century 21 Realty Center

  (845) 412-9860

  391 Bull Mill Rd, Chester, NY 10918
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  /23

  $3,400 per month

  • 5 Beds
  • 2.5 Baths
  • 1,815 Sq Ft
  • House for Rent

  208 Glenmere Rd, Chester, NY 10918

  A charming country cottage is available for rent and is situated on a picturesque country road. The main level features an eat-in kitchen, dining room, and two bedrooms, while the upper level has three bedrooms. The cottage boasts updated flooring, windows, kitchen, and heating. The interior has been freshly painted, and new appliances and flooring have been added in 2021. The older "Hamptons"

  Abraham Schwartz Priority Management

  208 Glenmere Rd, Chester, NY 10918
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  $260,000 Sold Mar 11, 2026

  2104 Whispering Hills, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1984

  Last Sold Summary

  • 13% Below List Price
  • $195/SF
  • 24 Days On Market

  Current Estimated Value $310,993

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  2104 Whispering Hills, Chester, NY 10918
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  Est $110,853 Not Listed For Sale

  30 Mount Ridge Ct, Monroe, NY 10950

  30 Mount Ridge Ct, Monroe, NY 10950

  Last Sold Summary

  • 21% Above List Price
  • 49 Days On Market

  Last Sold Price $91,500

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales
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  $369,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft

  3910 Whispering Hills, Chester, NY 10918

  Welcome to 3910 Whispering Hills — a refined, turnkey townhome in one of Chester’s most desirable residential enclaves. This thoughtfully appointed 3-bed, 2.5-bath home blends classic suburban elegance with low-maintenance living. Set within a mature, amenity-rich community, you’ll enjoy direct access to commuter transit, shops, and parks while savoring the quiet privacy prized by Hudson Valley

  

  Randolph Rogers

  eXp Realty

  (845) 957-9249

  3910 Whispering Hills, Chester, NY 10918
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  $3,200 per month

  • 3 Beds
  • 2.5 Baths
  • 1,670 Sq Ft
  • Townhouse for Rent

  404 Mountain Laurel Dr, Monroe, NY 10950

  Welcome to this beautifully maintained and updated 3 bedroom 2 and a half bath end-unit condo offering comfort, style, and scenic surroundings. This spacious home features a bright and open layout designed for both everyday living and entertaining. Step inside the sun drenched living space and notice the large family room which flows seamlessly into the dining area and kitchen. Your kitchen is

  Nicholas Carbone HomeSmart Homes & Estates

  404 Mountain Laurel Dr, Monroe, NY 10950
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  $415,000 Sold Apr 08, 2025

  2 Fields Ln, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,604 Sq Ft
  • Built 1972

  Last Sold Summary

  • 4% Above List Price
  • $159/SF
  • 24 Days On Market

  Current Estimated Value $457,579

  Last Listing Agent Margaret Galatro ARC Realty 1 in Sales

  2 Fields Ln, Chester, NY 10918
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  Est $350,404 Not Listed For Sale

  1110 Whispering Hills Dr, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1985

  1110 Whispering Hills Dr, Chester, NY 10918

  Last Sold Summary

  • 5% Above List Price
  • $252/SF
  • 16 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Yalitza Sepulveda Keller Williams Realty
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  $48,000

  • Land
  • 3.6 Acres
  • $13,333 per Acre

  1414 N Gore Rd, Chester, NY 12817

  North Gore Lot - Come build your dream on home this 3.6 acre wooded lot with power available roadside and perc test completed. Secluded location, yet only 15 minutes to Gore Mountain and 10 minutes to Minerva Beach with abundant outdoor recreation opportunities.

  

  Amanda Gadway

  Gadway Realty

  (518) 768-9981

  1414 N Gore Rd, Chester, NY 12817
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  $2,800 per month

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft
  • House for Rent

  71 Greycourt Rd, Chester, NY 10918

  Lovely and Private! Welcome to 71 Greycourt rd. this house is conveniently located just in the right location being close to major highways and shopping! This home was recently renovated with lots of upgrades. nice size kitchen, upgraded electricity, and much more! This house is private, sitting on a 2-acre property and a fenced-in yard for total privacy. This house is your dream rental! Don't

  Mordechai Ungar HFA Realty Group

  71 Greycourt Rd, Chester, NY 10918
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  $735,000 Sold Jul 21, 2025

  189 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft
  • Built 2004

  Last Sold Summary

  • 5% Above List Price
  • $247/SF
  • 19 Days On Market

  Current Estimated Value $711,177

  Last Listing Agent Patricia Brady Keller Williams Realty

  189 Creamery Pond Rd, Chester, NY 10918
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  Not Listed For Sale

  78 Panther Mtn Rd, Chester, NY 12817

  • 3 Beds
  • 1 Bath
  • 876 Sq Ft
  • Built 1961

  78 Panther Mtn Rd, Chester, NY 12817

  Last Sold Summary

  • $291/SF
  • 68 Days On Market

  Last Sold Price $255,000

  Last Listing Agent Angie Mead Gallo Realty ADK Inc
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  $289,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  3308 Whispering Hills Dr, Chester, NY 10918

  Welcome to your 2 bedroom, 1.5 bathroom town house condo with a one car garage in the highly desirable Whispering Hills Community in Chester, NY. Well maintained and cared for by its original owner, this unit is located in a nice private section along a green space. The second floor features two spacious bedrooms and one full bathroom. The primary bedroom has cathedral ceilings and a sizable

  

  Joseph Paoli

  Howard Hanna Rand Realty

  (845) 273-3536

  3308 Whispering Hills Dr, Chester, NY 10918
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  $3,800 per month

  • 4 Beds
  • 3 Baths
  • 2,457 Sq Ft
  • House for Rent

  118 Booth Rd, Chester, NY 10918

  A tastefully, restored 2-story, 4BR, 3BTH, bi-level style home set on over 3+ prestine acres at the end of a quaint cul-de-sac. Enjoy the large open fields, secluded from all the stresses of the day. Plenty of room for an athletic field, in-ground pool or just a peaceful sanctuary. The exquisite touches throughout add to its elegance, from high-end ceramics to restored oak floors. The

  Chris Scibelli Keller Williams Realty

  118 Booth Rd, Chester, NY 10918
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  $323,500 Sold Aug 11, 2025

  98 High St, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,360 Sq Ft
  • Built 1950

  Last Sold Summary

  • 5% Below List Price
  • $238/SF
  • 35 Days On Market

  Current Estimated Value $340,964

  Last Listing Agent Zachary Foley eXp Realty

  98 High St, Chester, NY 10918
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  Not Listed For Sale

  L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817

  L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817

  Last Sold Summary

  • 16 Days On Market

  Last Sold Price $58,450

  Last Listing Agent John Palermo John R. Palermo
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  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  5 Gabriels Dr, Chester, NY 10918

  Exquisite 4 bedroom 3 bath colonial , timeless grandeur meets modern luxury nestled gracefully on a private cul de sac. Amidst meticulously manicured grounds, this colonial style home offers an unparalleled blend of classic elegance and contemporary comfort, from the moment you approach the stately wrought iron fenced property and are greeted by a wrap around porch, you are welcomed by a grand

  Claudia Lepore Keller Williams Realty

  5 Gabriels Dr, Chester, NY 10918
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  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Townhouse for Rent

  82 High St Unit 5, Chester, NY 10918

  Very bright and spacious top-floor Penthouse apartment! Come see this open layout floorplan. The updated kitchen has a new stainless steel refrigerator and dishwasher. The Primary bedroom has large double closets and can accommodate a king-size bed. The living room/dining room combination is bright and sun-filled, with plenty of windows and an outside deck. You’ll appreciate the convenience of

  Lynda Hoss Weichert Realtors

  82 High St Unit 5, Chester, NY 10918
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  $875,000 Sold Jun 13, 2025

  157 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 3.5 Baths
  • 4,021 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Above List Price
  • $218/SF
  • 17 Days On Market

  Current Estimated Value $832,789

  Last Listing Agent Carla Terranova Keller Williams Realty

  157 Creamery Pond Rd, Chester, NY 10918
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  Est $786,083 Not Listed For Sale

  25 Eagle Crest Way, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Built 2014

  25 Eagle Crest Way, Chester, NY 10918

  Last Sold Summary

  • 7% Above List Price
  • $339/SF
  • 14 Days On Market

  Last Sold Price $735,000

  Last Listing Agent Alyssa Scancarello Howard Hanna Rand Realty
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  $635,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,954 Sq Ft

  25 Sugarloaf Mountain Rd, Chester, NY 10918

  MONROE WOODBURY SCHOOLS! BRAND NEW KITCHEN! ABSOLUTE MUST SEE!Welcome to your dream home in the highly sought-after Monroe Woodbury School District. Privately set at the end of a long driveway on just under one acre, this beautifully renovated Colonial offers an incredible balance of peace, privacy, and recent upgrades.From the moment you step inside, you are greeted by a stunning foyer that

  Frank Muccari Cronin & Company Real Estate

  25 Sugarloaf Mountain Rd, Chester, NY 10918
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  $1,500 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  8 Main St, Chester, NY 10918

  Located in Historic Downtown Chester. This is a 1 bedroom apartment located on the 2nd floor. Open floor plan with exposed brick walls and lots of natural light. Walking distance to shops, restaurants, brewery, and the Heritage Trail. Close to public transportation and Route 17.

  Jeanmarie Valentin HomeSmart Homes & Estates

  8 Main St, Chester, NY 10918
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  $610,000 Sold Mar 12, 2026

  44 Cedar Pond Ln, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft
  • Built 1991

  Last Sold Summary

  • 2% Above List Price
  • $325/SF
  • 48 Days On Market

  Current Estimated Value $752,893

  Last Listing Agent Ammar Iqbal eXp Realty

  44 Cedar Pond Ln, Chester, NY 10918
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  Not Listed For Sale

  68 Conklingtown Rd, Chester, NY 10918

  • 6 Beds
  • 2 Baths
  • 2,138 Sq Ft
  • Built 1950

  68 Conklingtown Rd, Chester, NY 10918

  Last Sold Summary

  • $241/SF
  • 47 Days On Market

  Last Sold Price $515,000

  Last Listing Agent Chaim Klein MS Realty Group USA, Inc
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  $699,990

  • 4 Beds
  • 3 Baths
  • 1,867 Sq Ft

  34 Mountainside Dr, Chester, NY 10918

  ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.). FANTASTIC

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
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  $2,000 per month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  1396 Kings Hwy, Chester, NY 10918

  Newly renovated 3 bedroom unit located in the heart of Sugar Loaf and within the Warwick School District. This second-floor walkup features a bright white kitchen with stainless steel appliances, including an in-unit washer/drier, and offers a large private balcony with scenic views of Sugar Loaf Mountain. The unit is situated above a restaurant; music may be audible as late as 11 PM on Friday

  Roxanne Hartman Timothy W. Kramer

  1396 Kings Hwy, Chester, NY 10918
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  $320,000 Sold Feb 13, 2026

  2812 Whispering Hills Unit 577, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Built 1984

  Last Sold Summary

  • 10% Above List Price
  • $295/SF
  • 22 Days On Market

  Current Estimated Value $296,004

  Last Listing Agent Kathy White Exit Realty Connections

  2812 Whispering Hills Unit 577, Chester, NY 10918
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  Est $467,481 Not Listed For Sale

  20 High St, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 2,488 Sq Ft
  • Built 1825

  20 High St, Chester, NY 10918

  Last Sold Summary

  • 17% Above List Price
  • $160/SF
  • 35 Days On Market

  Last Sold Price $399,000

  Last Listing Agent George Koudounas RE/MAX Benchmark Realty Group
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  $650,000

  • 5 Beds
  • 3 Baths
  • 2,983 Sq Ft

  9 Mount Ridge Ct, Monroe, NY 10950

  Spacious Center Hall Colonial with open concept kitchen, fireplace, deck, and large primary suite with walk-in closets. A dramatic two-story entry leads to an open concept kitchen with abundant counter space, large dinette area, and sliding doors to a spacious deck --perfect for entertaining. The kitchen flows into the open family room and living room with fireplace, creating an ideal setup for

  Richard Froehlich RE/MAX Benchmark Realty Group

  9 Mount Ridge Ct, Monroe, NY 10950
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  $3,050 per month

  • 4 Beds
  • 1.5 Baths
  • 1,605 Sq Ft
  • House for Rent

  98 Main St, Chester, NY 10918

  Welcome to 98 Main St: a gracious Colonial in the center of the village of Chester!A huge "wrap-around" front porch greets you when you arrive. Once inside, you will be impressed with the "old world" charm of the stained-glass windows, dark wood trim, Hardwood floors and the pocket doors in the Living Room. Many large windows downstairs let in plenty of sunlight! Upstairs there are 4 nice

  Eveline White Hudson Valley Griffith

  98 Main St, Chester, NY 10918
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  $382,000 Sold Jan 12, 2026

  4703 Whispering Hills Dr, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1991

  Last Sold Summary

  • 4% Above List Price
  • $287/SF
  • 61 Days On Market

  Current Estimated Value $372,939

  Last Listing Agent Erin Connolly Artisan Realty

  4703 Whispering Hills Dr, Chester, NY 10918
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  Est $934,076 Not Listed For Sale

  221 Oxford Rd, Chester, NY 10918

  • 4 Beds
  • 3.5 Baths
  • 4,644 Sq Ft
  • Built 2000

  221 Oxford Rd, Chester, NY 10918

  Last Sold Summary

  • 4% Above List Price
  • $194/SF
  • 132 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group

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