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Chester, VT Homes for Sale

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  • 41 Vt Route 103 S, Chester, VT 05143
    41 Vt Route 103 S, Chester, VT 05143
    41 Vt Route 103 S, Chester, VT 05143
    /33

    $299,000

    • 2,702 Sq Ft

    41 Vt Route 103 S, Chester, VT 05143

    Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. Presently, all three units are vacant. Easy to show! There is good

    Glenn Olney Barrett and Valley Associates Inc.

    41 Vt Route 103 S, Chester, VT 05143
  • 810 Quarry Rd, Chester, VT 05143
    810 Quarry Rd, Chester, VT 05143
    810 Quarry Rd, Chester, VT 05143
    /60

    $815,000

    • 3 Beds
    • 2.5 Baths
    • 2,466 Sq Ft

    810 Quarry Rd, Chester, VT 05143

    Not quite 20 years young, this charming custom-built colonial sits on a private knoll, surveying its 77+/- acre parcel. Blending country comfort and eloquence, you'll find quality craftsmanship throughout, such as blue stone floors and a stone archway. Wide plank floors lead to the country kitchen with soapstone countertops. Enter the spacious dining room with tray-beamed ceilings and oversized

    Joseph Karl William Raveis Real Estate Vermont Properties

    810 Quarry Rd, Chester, VT 05143
  • 106 Contro Rd, Chester, VT 05143
    106 Contro Rd, Chester, VT 05143
    106 Contro Rd, Chester, VT 05143
    /14

    $289,000

    • 2 Beds
    • 2.5 Baths
    • 1,475 Sq Ft

    106 Contro Rd, Chester, VT 05143

    Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided

    Christine Lewis Brattleboro Area Realty

    106 Contro Rd, Chester, VT 05143
  • 00 Contro Rd, Chester, VT 05143
    00 Contro Rd, Chester, VT 05143
    00 Contro Rd, Chester, VT 05143
    /3

    $159,000

    • Land
    • 5 Acres
    • $31,800 per Acre

    00 Contro Rd, Chester, VT 05143

    There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for a homestead farm, little get away cottage or a lovely lodge! Just build the lifestyle you want and forget the rest! A few minutes to Main Street Chester and the Common, A few more to the interstate, and nestled close to skiing, hiking and boating. The WWW permit is issued, town

    Christine Lewis Brattleboro Area Realty

    00 Contro Rd, Chester, VT 05143
  • 514 1st Ave, Chester, VT 05143
    514 1st Ave, Chester, VT 05143
    514 1st Ave, Chester, VT 05143
    /37

    $529,000

    • 5 Beds
    • 5 Baths
    • 3,880 Sq Ft

    514 1st Ave, Chester, VT 05143

    Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chester’s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. It’s a property that allows you to live outwardly—work the land, keep animals,

    Daire Gibney Barrett and Valley Associates Inc.

    514 1st Ave, Chester, VT 05143
  • 3019 Popple Dungeon Rd, Chester, VT 05143
    3019 Popple Dungeon Rd, Chester, VT 05143
    3019 Popple Dungeon Rd, Chester, VT 05143
    /20

    $169,000

    • 1 Bed
    • 1 Bath
    • 200 Sq Ft

    3019 Popple Dungeon Rd, Chester, VT 05143

    Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3019 Popple Dungeon Rd, Chester, VT 05143
  • 4351 Vermont 11, Chester, VT 05143
    4351 Vermont 11, Chester, VT 05143
    4351 Vermont 11, Chester, VT 05143
    /20

    $149,900

    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft

    4351 Vermont 11, Chester, VT 05143

    Almost there! This owner has taken this property to a new level...had the septic discovered and has a report, upgraded the electric entrance and added an EV station, laid flooring, opened up a wall for a much nicer open concept, cleaned and made into a little cottage for skiing, nature loving or just plain home. There are rain barrels for water, let nature fill them up or hire the local water

    Christine Lewis Brattleboro Area Realty

    4351 Vermont 11, Chester, VT 05143
  • 127 Trombley Rd, Chester, VT 05143
    127 Trombley Rd, Chester, VT 05143
    127 Trombley Rd, Chester, VT 05143
    /20

    $449,000

    • 5 Beds
    • 1 Bath
    • 2,856 Sq Ft

    127 Trombley Rd, Chester, VT 05143

    Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres in Andover with 5 in Chester. The setting includes over 20 acres of flat, open meadows along the Williams River, framed by wooded hills and distant ridgelines. The forest is mixed with possible timber value as well as a nice sugarbush waiting to be tapped. The original farmhouse, approached by a

    Daire Gibney Barrett and Valley Associates Inc.

    127 Trombley Rd, Chester, VT 05143
  • 1979 N Hill Rd, Chester, VT 05143
    1979 N Hill Rd, Chester, VT 05143
    1979 N Hill Rd, Chester, VT 05143
    /42

    $429,000

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    1979 N Hill Rd, Chester, VT 05143

    Welcome to this attractive Andover Contemporary home, perfectly suited for year-round living or as a Vermont vacation retreat. Built in 2005, this 3 bedroom, 2 bath residence offers modern comfort in a peaceful country setting on 2.1 acres while being just minutes from Okemo Mountain Resort and close to scenic snowmobile trails—ideal for outdoor enthusiasts in every season. The inviting

    Geralyn Donohue Engel & Völkers Okemo

    1979 N Hill Rd, Chester, VT 05143
  • 00 Remington Rd, Chester, VT 05143
    00 Remington Rd, Chester, VT 05143
    00 Remington Rd, Chester, VT 05143
    /14

    $74,000

    • Land
    • 15.5 Acres
    • $4,774 per Acre

    00 Remington Rd, Chester, VT 05143

    Bring your ideas for building your own home on this 15.5 acre parcel of land in the quintessential town of Chester. Located minutes to the 91 FWY. Vermont Academy nearby along with several hiking and snowmobile trails. Seller has included the cost for clearing the building site and a driveway to house site. Come look at this property and enjoy all it has to offer.

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    00 Remington Rd, Chester, VT 05143
  • 447 Elm St, Chester, VT 05143
    447 Elm St, Chester, VT 05143
    447 Elm St, Chester, VT 05143
    /27

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    447 Elm St, Chester, VT 05143

    Welcome to your dream home – This meticulously maintained New England-style gem is bursting with charm and modern convenience. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by the beautiful hardwood floors that add warmth and character to every room.Bask in the great natural light that fills

    Lisa Kelley Cummings & Co

    447 Elm St, Chester, VT 05143
  • 918 Lovers Lane Rd, Chester, VT 05143
    918 Lovers Lane Rd, Chester, VT 05143
    918 Lovers Lane Rd, Chester, VT 05143
    /21

    $145,000

    • Land
    • 22.23 Acres
    • $6,523 per Acre

    918 Lovers Lane Rd, Chester, VT 05143

    Located only 2 miles from the picturesque Chester Green you will encounter this newly created 22 acre building parcel on scenic Lover's Lane. This property consists of a 2 acre meadow ideal for building and a 20 acre woodlot consisting of pine, hemlock, oak and maple for sugaring. Beautiful fieldstone walls border most of the boundary lines. The surveyed parcel has an approved 4 bedroom State

    Alan Gombosi Northland Real Estate

    918 Lovers Lane Rd, Chester, VT 05143
  • 1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    1175 Quarry Rd, Chester, VT 05143
    /22

    $300,000

    • Land
    • 75 Acres
    • $4,000 per Acre

    1175 Quarry Rd, Chester, VT 05143

    An extraordinary potential homesite set in the hills of southern Vermont. This expansive 75-acre parcel offers the perfect blend of privacy, natural beauty, and endless potential. Whether you dream of building a secluded hilltop retreat or preserving land for recreation and conservation, this property invites endless possibilties. Improvements include a septic system, dug well, electricity and a

    Jessica Samples BHG Masiello Keene

    1175 Quarry Rd, Chester, VT 05143
  • 717 Horsenail Hill Rd, Chester, VT 05143
    717 Horsenail Hill Rd, Chester, VT 05143
    717 Horsenail Hill Rd, Chester, VT 05143
    /38

    $749,000 New Construction

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

    717 Horsenail Hill Rd, Chester, VT 05143

    Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances.The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious

    Robin Apps Four Seasons Sotheby's Int'l Realty

    717 Horsenail Hill Rd, Chester, VT 05143
  • 1342 Old Stage Rd, Chester, VT 05143
    1342 Old Stage Rd, Chester, VT 05143
    1342 Old Stage Rd, Chester, VT 05143
    /56

    $879,000

    • 2 Beds
    • 2 Baths
    • 1,576 Sq Ft

    1342 Old Stage Rd, Chester, VT 05143

    Welcome to your own private retreat—98 acres of Vermont beauty offering meadows, woods, two ponds, and eight versatile outbuildings. Thoughtfully maintained, this charming home is nestled in a park-like setting complete with long, historic rock walls, mature trees, and lovely perennial gardens. Nature lovers will appreciate the abundance of wildlife, from hummingbirds and ducks to deer and the

    Jessica Landers Barrett and Valley Associates Inc.

    1342 Old Stage Rd, Chester, VT 05143
  • 688 Hidden Heights Rd, Chester, VT 05143
    688 Hidden Heights Rd, Chester, VT 05143
    688 Hidden Heights Rd, Chester, VT 05143
    /59

    $685,000

    • 3 Beds
    • 2 Baths
    • 2,205 Sq Ft

    688 Hidden Heights Rd, Chester, VT 05143

    Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of

    Joseph Karl William Raveis Real Estate Vermont Properties

    688 Hidden Heights Rd, Chester, VT 05143
  • 95 Church St, Chester, VT 05143
    95 Church St, Chester, VT 05143
    95 Church St, Chester, VT 05143
    /52

    $625,000

    • 4 Beds
    • 3 Baths
    • 2,794 Sq Ft

    95 Church St, Chester, VT 05143

    Charming Renovated Farmhouse in the Heart of Chester This beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway. Inside, enjoy a spacious kitchen with custom pantry shelving, a

    McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    95 Church St, Chester, VT 05143
  • 00 Vermont 103, Andover, VT 05143
    00 Vermont 103, Andover, VT 05143
    00 Vermont 103, Andover, VT 05143
    /60

    $200,000

    • Land
    • 6.63 Acres
    • $30,166 per Acre

    00 Vermont 103, Andover, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

    Rachael Rogala Lange & Lange

    00 Vermont 103, Andover, VT 05143
  • 00 Vt Route 103 N, Chester, VT 05143
    00 Vt Route 103 N, Chester, VT 05143
    00 Vt Route 103 N, Chester, VT 05143
    /60

    $115,000

    • Land
    • 3.28 Acres
    • $35,061 per Acre

    00 Vt Route 103 N, Chester, VT 05143

    Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life.The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing.

    Rachael Rogala Lange & Lange

    00 Vt Route 103 N, Chester, VT 05143
  • 0 Remington Rd Unit 5049900, Chester, VT 05143
    0 Remington Rd Unit 5049900, Chester, VT 05143
    0 Remington Rd Unit 5049900, Chester, VT 05143
    /21

    $55,000

    • Land
    • 1.52 Acres
    • $36,184 per Acre

    0 Remington Rd Unit 5049900, Chester, VT 05143

    If you're dreaming of open skies, peaceful surroundings, and your own slice of Vermont, this property delivers. Just minutes from the charming Chester village green, this land offers the best of both worlds—seclusion and convenience. Step onto the property and take in the wide-open space surrounded by mature trees, offering privacy and natural beauty in every season. Whether you're envisioning

    Frank Provance Diamond Realty

    0 Remington Rd Unit 5049900, Chester, VT 05143
  • 611 Simmons Rd, Chester, VT 05143
    611 Simmons Rd, Chester, VT 05143
    611 Simmons Rd, Chester, VT 05143
    /32

    $1,995,000

    • 2 Beds
    • 4 Baths
    • 3,514 Sq Ft

    611 Simmons Rd, Chester, VT 05143

    Skygate Farm is a historic Vermont farmstead first settled in the 1800s, which today spans over 300 acres of meadows, forests, trails, and weathered stone walls. The setting speaks of an early farmer’s wisdom — sited along a gentle hill to shield against the northwest winds, while opening to the first light of day and the vast mountain views to the east. Found at the end of a winding gravel road,

    Dia Jenks LandVest, Inc/Woodstock

    611 Simmons Rd, Chester, VT 05143
  • 157 Thompson Rd, Chester, VT 05143
    157 Thompson Rd, Chester, VT 05143
    157 Thompson Rd, Chester, VT 05143
    /56

    $1,125,000

    • 4 Beds
    • 2.5 Baths
    • 2,772 Sq Ft

    157 Thompson Rd, Chester, VT 05143

    Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system,

    Joe Castaluccio Winhall Real Estate

    157 Thompson Rd, Chester, VT 05143
  • 419 Coach Rd, Chester, VT 05143
    419 Coach Rd, Chester, VT 05143
    419 Coach Rd, Chester, VT 05143
    /12

    $239,000

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    419 Coach Rd, Chester, VT 05143

    Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.

    Amy Carson Lowe's Real Estate, LLC

    419 Coach Rd, Chester, VT 05143
  • 534 Elm St, Chester, VT 05143
    534 Elm St, Chester, VT 05143
    534 Elm St, Chester, VT 05143
    /60

    $599,000

    • 7 Beds
    • 3.5 Baths
    • 3,850 Sq Ft

    534 Elm St, Chester, VT 05143

    Have you been waiting to buy just the right property? An impressive home in a special town in an amazing state might be perfect. This well-loved Victorian has 4 bedrooms in the main house and another 3 bedrooms in the carriage house unit. There is a storage room in between the two spaces with doors to open to easily connect the units. The beautiful main house has a farmhouse-style kitchen, formal

    Tyleen Murray Kelley Real Estate, Inc.

    534 Elm St, Chester, VT 05143
  • 160 Depot St, Chester, VT 05143
    160 Depot St, Chester, VT 05143
    160 Depot St, Chester, VT 05143
    /26

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,327 Sq Ft

    160 Depot St, Chester, VT 05143

    Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

    Joshua Lemieux Remax Summit

    160 Depot St, Chester, VT 05143
  • 1057 Quarry Rd, Chester, VT 05143
    1057 Quarry Rd, Chester, VT 05143
    1057 Quarry Rd, Chester, VT 05143
    /56

    $594,000

    • 5 Beds
    • 3.5 Baths
    • 3,470 Sq Ft

    1057 Quarry Rd, Chester, VT 05143

    Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

    Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

    1057 Quarry Rd, Chester, VT 05143
  • 3630 Vt Route 103 N, Chester, VT 05143
    3630 Vt Route 103 N, Chester, VT 05143
    3630 Vt Route 103 N, Chester, VT 05143
    /30

    $625,000

    • 3 Beds
    • 3 Baths
    • 4,324 Sq Ft

    3630 Vt Route 103 N, Chester, VT 05143

    Exceptional Investment Opportunity in Chester, VTDiscover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3630 Vt Route 103 N, Chester, VT 05143
  • 000 Green Mountain Turnpike, Andover, VT 05143
    000 Green Mountain Turnpike, Andover, VT 05143
    000 Green Mountain Turnpike, Andover, VT 05143
    /22

    $275,000

    • Land
    • 91 Acres
    • $3,022 per Acre

    000 Green Mountain Turnpike, Andover, VT 05143

    91± Acres with Stunning Mountain Views in Chester, VermontDiscover a breathtaking 91± acre property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this

    Daire Gibney Barrett and Valley Associates Inc.

    000 Green Mountain Turnpike, Andover, VT 05143
  • 0 Snell Rd, Chester, VT 05143
    0 Snell Rd, Chester, VT 05143
    0 Snell Rd, Chester, VT 05143
    /24

    $89,000

    • Land
    • 10.4 Acres
    • $8,558 per Acre

    0 Snell Rd, Chester, VT 05143

    This rolling, wooded 10.4+/- acre surveyed parcel in Chester offers 244 feet of road frontage and gently rolling land with a mix of hardwoods and pine. A lovely stream meanders through the property which is also dotted with interesting large boulders and old stone walls. If you are looking for privacy, there is potential for a secluded home site set back from the road. Utility pole is at the road

    Geralyn Donohue Engel & Völkers Okemo

    0 Snell Rd, Chester, VT 05143
  • 00 Quarry Rd, Chester, VT 05143
    00 Quarry Rd, Chester, VT 05143
    00 Quarry Rd, Chester, VT 05143
    /27

    $219,000

    • Land
    • 27.8 Acres
    • $7,878 per Acre

    00 Quarry Rd, Chester, VT 05143

    Discover your perfect Vermont getaway on this exceptional 27.8± acre hillside parcel in picturesque Chester, Vermont. Offering sweeping mountain views, privacy, and endless possibilities, this property is ready for your vision. With an approved Vermont state wastewater permit for a 4-bedroom home, you can begin designing your dream family retreat or vacation home right away. A cleared preliminary

    Geralyn Donohue Engel & Völkers Okemo

    00 Quarry Rd, Chester, VT 05143
Vermont Windsor County Chester

Real Estate & Homes for Sale in Chester, VT

Frequently Asked Questions

What is the average home price in Chester, VT?
Homes for sale in Chester, VT have an average home price of $625,729.
How many homes have sold over the last 12 months in Chester, VT?
53 homes have sold in Chester, VT over the last 12 months.
What are the most popular zip codes in Chester, VT?
The most popular zip codes in Chester, VT include 05143, 05156, 05146, 05149 and 05150.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $469,000. If you put a 20% down payment of $93,800 and had a 30-year fixed mortgage with an interest rate of 6.24%, your estimated principal and interest payment would be $2,310 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $99K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chester, VT?
Chester, VT has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Cavendish Town Elementary School, Ludlow Elementary School and Grafton Elementary School. Browse all the schools in Chester, VT to learn more.

Home Trends in Chester, VT

On average, homes in Chester, VT sell after 70 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, VT over the last 12 months is $412,000, up 12% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$412,000
Median Single Family Sale Price
$416,916
Median Townhouse Sale Price
$778,000
Average Price Per Sq Ft
$293
Number of Homes for Sale
17
Last 12 months Home Sales
53
Months of Supply
3.80
Median List Price
$469,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
12%
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Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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