Windsor, VT Homes

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  /52

  $625,000

  • 4 Beds
  • 3 Baths
  • 1,360 Sq Ft

  261 Hawk Spur Rd, Plymouth, VT 05056

  Peaceful Retreat at Hawk Resort. Located on the west side of Hawk Resort, this home sits on a quiet, town-maintained road in a peaceful, wooded setting. The double lot offers privacy and potential for expanded views.The main level has an open layout with a stone wood-burning fireplace with efficient insert and glass sliders leading to a large deck. There is also a bedroom and full bath on

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  261 Hawk Spur Rd, Plymouth, VT 05056
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  /24

  $3,850 per month

  • 4 Beds
  • 3.5 Baths
  • 2,225 Sq Ft
  • House for Rent

  1802 Vt 100a, Plymouth, VT 05056

  This property at 1802 VT 100A features 4 bedrooms and 3.5 bathrooms, offering a total of 2,225 square feet of living space. An additional room could be converted to a fifth bedroom. This charming home is available for long-term lease starting Sept. 1 (or possibly earlier) and offers a perfect blend of rustic character and modern comfort. The great room provides ample space for relaxation and

  1802 Vt 100a, Plymouth, VT 05056
• 

  

  

  /54

  $535,000 Sold Aug 01, 2025

  • 2,135 Sq Ft
  • $251/SF
  • 51 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1985

  228 Birch Landing Rd Unit 27, Plymouth, VT 05056

  Welcome to Birch Landing on Echo Lake in historic Plymouth, Vermont.This spacious end-unit condominium offers over 2,000 square feet of living space in one of the most sought-after private locations within the complex. Set at the quiet end of the road, it boasts a direct path from the back deck to the lake, perfect for morning swims or sunset paddles. The main level includes a bedroom, a

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  228 Birch Landing Rd Unit 27, Plymouth, VT 05056
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  /40

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,484 Sq Ft

  954 E Ash Rd Unit L-17, Plymouth, VT 05056

  954 E Ash Rd Unit L-17, Plymouth, VT 05056
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  /51

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 1,788 Sq Ft

  162 Bear Hill Rd, Plymouth, VT 05056

  Beautifully renovated 3-bedroom, 2.5-bath chalet perched on the slope of the former Plymouth Notch Ski Area. This move-in-ready home combines mountain charm with modern comfort. Interior upgrades include new flooring, fully renovated bathrooms, stylish lighting, and a refreshed kitchen with granite countertops, tile backsplash, pot filler, and all-new stainless steel appliances. The open-concept

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  162 Bear Hill Rd, Plymouth, VT 05056
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  /40

  $20,000 per month

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft
  • Townhouse for Rent

  71 Lakeview Rd Unit 20, Plymouth, VT 05056

  Enjoy Your Ski Season In Comfort and Style!Get ready to elevate your ski season experience with this stunning 3 bedroom, 3 bath, townhouse for rent in Plymouth, Vermont! This gem features a cozy wood burning fireplace, atrium windows for natural light, vaulted ceilings for a spacious feel, a charming loft area with extra sleeping space, Echo Lake views, and a serene back deck. Located in a

  Frank Provance Diamond Realty

  71 Lakeview Rd Unit 20, Plymouth, VT 05056
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  /22

  $55,000 Sold Aug 01, 2025

  • Land
  • 1.29 Acres
  • $42,636 per Acre

  • 66 Days On Market

  00 Dublin Rd, Plymouth, VT 05056

  Tucked away off a quiet country dirt road in the heart of Plymouth, Vermont, this serene 1.26 - acre parcel offers the perfect canvas for your mountain retreat. Wooded and mostly cleared for privacy and natural beauty, this lot combines peaceful seclusion with practical convenience—featuring an existing power meter already in place, making hook-ups a breeze. Relax to the soothing sounds of a

  Kevin Barnes William Raveis Real Estate Vermont Properties

  00 Dublin Rd, Plymouth, VT 05056
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  /37

  Est $599,226 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  18 Town Line Rd, Plymouth, VT 05056

  18 Town Line Rd, Plymouth, VT 05056
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  /60

  $649,000

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  5100 Route 100, Plymouth, VT 05056

  (Das Grunebergehaus) The Green Mountain House. First time offered on market since 1978. This gorgeous farmhouse, circa 1831, has been lovingly maintained & updated over the current owner's term of ownership. Previously owned by the Coolidge Family. During the years of Calvin Coolidge's presidency this home was used as a guest house for political figures to come & stay while visiting President

  Marni Rieger KW Vermont-Killington

  5100 Route 100, Plymouth, VT 05056
• 

  

  /22

  $12,000 Sold Jul 29, 2025

  • Land
  • 1.01 Acres
  • $11,881 per Acre

  • 53 Days On Market

  0 Crimson Hawk Rd, Plymouth, VT 05056

  This parcel is part of the Hawk West side of Hawk Mountain Resort and is one of the most affordable ways to get into the Hawk Mountain Resort Community. Easy access to Route 100 and only minutes to Okemo or Killington. There are 4 lakes all within a few minutes as well. Plenty of hiking, biking, boating, and fishing in the area. All plans and permits must be approved by the Hawk Architectural

  Kevin Barnes William Raveis Real Estate Vermont Properties

  0 Crimson Hawk Rd, Plymouth, VT 05056
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  /40

  Est $682,833 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,285 Sq Ft

  65 Woodpecker Rd, Plymouth, VT 05056

  65 Woodpecker Rd, Plymouth, VT 05056
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  /55

  $739,000

  • 4 Beds
  • 4 Baths
  • 1,730 Sq Ft

  78 Coopers Trace, Plymouth, VT 05056

  Located in Hawk Resort, halfway between Killington and Okemo, this four-bedroom, four-bath home offers both privacy and convenience.The main floor features an open layout with cathedral ceilings, wide pine floors, and plenty of natural light from large windows and skylights. The kitchen has been updated, and fresh paint throughout gives the home a clean, refreshed look. The dining area opens

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  78 Coopers Trace, Plymouth, VT 05056
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  /37

  $190,000 Sold Jul 23, 2025

  • 1,479 Sq Ft
  • $128/SF
  • 96 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  182 Upper Round Top Rd Unit E, Plymouth, VT 05056

  Sweet mountain 3 bedroom plus loft and 2 full bathrooms furnished and equipped townhouse vacation retreat with beautiful views located minutes to Killington or Okemo Mountain Resort. Offering very close access direct from the townhouse to VAST snowmobiling trails/hiking/mountain biking trails. There are superb lakes right down the road to kayak, swim and fish. The floor plan is open concept ideal

  Marni Rieger KW Vermont-Killington

  182 Upper Round Top Rd Unit E, Plymouth, VT 05056
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  /40

  Est $668,383 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft

  131 Upper Round Top Rd, Plymouth, VT 05056

  131 Upper Round Top Rd, Plymouth, VT 05056
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  /60

  $649,900

  • 4 Beds
  • 4 Baths
  • 2,818 Sq Ft

  200 Peregrine Rd, Plymouth, VT 05056

  Located in between the two largest ski resorts in the East- Killington and Okemo Mountain Resorts. Custom design & built 4 bedroom/ 4 bathroom Hawk home faces directly South and affords beautiful seasonal lake and mountain views from this gorgeous open concept contemporary with loads of glass pouring in natural sunlight in every room and lovely wood floors throughout. The floor plan is ideal for

  Marni Rieger KW Vermont-Killington

  200 Peregrine Rd, Plymouth, VT 05056
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  /45

  $354,000 Sold Jul 21, 2025

  • 862 Sq Ft
  • $411/SF
  • 67 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1988

  1226 E Ash Rd Unit L-33, Plymouth, VT 05056

  Enjoy all-season comfort in this spacious two-bedroom condominium at Hawk Resort, nestled in the picturesque lakes region between Killington and Okemo Mountain Resorts. Featuring over 1,700 square feet of living space, the main level offers an open living and dining area with warm wood flooring, an ensuite bedroom, a galley kitchen, a convenient half bath, and a lockout entry for winter warmth.

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  1226 E Ash Rd Unit L-33, Plymouth, VT 05056
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  /27

  Est $532,099 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,176 Sq Ft

  2908 Route 100a, Plymouth, VT 05056

  2908 Route 100a, Plymouth, VT 05056
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  /60

  $1,025,000 Under Contract

  • 6 Beds
  • 6 Baths
  • 3,209 Sq Ft

  181 Meadow Hawk Rd Unit PVT, Plymouth, VT 05056

  Striking and spacious, this beautifully expanded and renovated home offers over 4,000 sq ft of open-concept living and scenic views. Set on ~3 private acres near the Hawk Resort trail system and just a short walk to Lake Amherst, this ideal location offers easy access to Okemo, Killington, and Woodstock.Completed in 2006, the home features three levels of well-designed living. A tiled

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  181 Meadow Hawk Rd Unit PVT, Plymouth, VT 05056
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  /42

  $950,000 Sold Jul 03, 2025

  • 2,898 Sq Ft
  • $328/SF
  • 417 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1898

  9 Scott Terrace, Plymouth, VT 05149

  Welcome to Lakeview Retreat! Nestled on the shores of Echo Lake with stunning views of Okemo Ski Mountain, this exceptional property offers the perfect blend of natural beauty and recreational opportunities. Situated on two acres of land, this estate boasts not one, but two charming houses, making it ideal for hosting guests or having a family compound.Additionally, the small garden plot

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  9 Scott Terrace, Plymouth, VT 05149
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  /39

  Est $888,249 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,819 Sq Ft

  286 Dix Hill Rd, Ludlow, VT 05149

  286 Dix Hill Rd, Ludlow, VT 05149
• 

  

  /27

  $650,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  952 Scout Camp Rd, Plymouth, VT 05056

  This is a little bit of heaven right here. Located on the backside of quiet Lake Amherst is a home that is much more than a summer camp. Built in 2015, so there are virtually no headaches to be expected. The structure is in great shape and so are the mechanicals. There is a porch across the entire front of the house to overlook the lake...room for dining, sleeping or relaxing in the rockers with

  Betty McEnaney Diamond Realty

  952 Scout Camp Rd, Plymouth, VT 05056
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  /10

  $130,000 Sold Jun 18, 2025

  • Land
  • 50 Acres
  • $2,600 per Acre

  • 236 Days On Market

  00 Route 100a, Plymouth, VT 05056

  Raw land ready for your Vermont dreams to begin. Looking to build your cabin in the woods away from it all? This could be your spot! With some imagination this 50 acre wooded parcel of pristine Vermont land could be many things. Bordered by the Coolidge State Forest this is a paradise for hiking or exploring the forest. Nearby watersports, biking and golf add to the list of activities. If larger

  Elevations Team Real Broker LLC

  00 Route 100a, Plymouth, VT 05056
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  /40

  Est $897,002 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,958 Sq Ft

  284 Soaring Hawk Rd, Plymouth, VT 05056

  284 Soaring Hawk Rd, Plymouth, VT 05056
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  /44

  $545,000

  • 4 Beds
  • 2.5 Baths
  • 1,674 Sq Ft

  2110 Lynds Hill Rd, Plymouth, VT 05056

  Wonderful location on over 14 acres with outstanding mountain views! Immediate access to VAST snowmobile trails and endless hiking/mountain biking trails. This 4 bedroom, 2 1/2 bath mountain contemporary chalet has an open concept floor plan with loads of glass to soak in the amazing views. Handsome fieldstone hearth with wood burning fireplace on the main living level. The primary bedroom with

  Marni Rieger KW Vermont-Killington

  2110 Lynds Hill Rd, Plymouth, VT 05056
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  /32

  $425,000 Sold Jun 06, 2025

  • 3,316 Sq Ft
  • $128/SF
  • 110 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1970

  147 Davis Rd, Ludlow, VT 05149

  Check out this wonderful family retreat! With 5 generous bedrooms, large living room, large deck and country setting...BONUS "rec area" in the barn and deck is “hot tub “ ready with power in place ! There is more than enough room for everyone! Only minutes to world class skiing at Okemo-Vail resort or Killington, close to the lakes and snowmobile trails. Lower level is mostly finished with living

  Lisa Kelley Cummings & Co

  147 Davis Rd, Ludlow, VT 05149
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  /40

  Est $747,633 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,565 Sq Ft

  122 Dead End Rd, Plymouth, VT 05056

  122 Dead End Rd, Plymouth, VT 05056
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  /35

  $399,000

  • 3 Beds
  • 3.5 Baths
  • 2,038 Sq Ft

  1497 Route 100a, Plymouth, VT 05056

  Talk about a convenient location! Central to Killington, Woodstock, and Ludlow. This home is absolutely suitable for full time living or vacation usage. Once upon a time, this was an old schoolhouse. Since then, it was reborn as a home. The floorplan is tremendously flexible with a den/office/TV room upstairs and down along with bedrooms both upstairs and down. A couple of really nice bay

  Betty McEnaney Diamond Realty

  1497 Route 100a, Plymouth, VT 05056
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  /35

  $630,000 Sold May 02, 2025

  • 2,072 Sq Ft
  • $304/SF
  • 0 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1975

  177 Black River Rd, Plymouth, VT 05056

  Tucked away at the end of a quiet dead-end road, this classic Lindal Cedar home offers privacy, charm, and a flexible layout perfect for year-round enjoyment. Originally built in 1975, this Lindel Cedar home has been thoughtfully expanded over the years to include a sunny dining/living room, heated sunroom, enclosed lower-level porch, and an expansive composite deck featuring a sleek steel cable

  Franchesca Collins Hall Collins Real Estate Group

  177 Black River Rd, Plymouth, VT 05056
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  /40

  Est $577,629 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  181 Upper Round Top Rd, Plymouth, VT 05056

  181 Upper Round Top Rd, Plymouth, VT 05056
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  /33

  $225,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  2579 Vermont Route 100, Plymouth, VT 05056

  Tucked among the trees in beautiful Plymouth, this rustic getaway offers a peaceful setting with easy access to outdoor recreation. This property offers unbeatable access to some of Vermont’s best recreation. Just a short drive to both Killington and Okemo for world-class skiing, and minutes from Echo Lake and Plymouth State Park, this is a four-season location ideal for outdoor lovers.The home

  Frank Provance Diamond Realty

  2579 Vermont Route 100, Plymouth, VT 05056
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  /32

  $83,000 Sold May 02, 2025

  • Land
  • 2.21 Acres
  • $37,557 per Acre

  • 286 Days On Market

  000 Echo View Dr, Plymouth, VT 05149

  Welcome to Echo View Estates. Perfectly located between Okemo and Killington Mountain Resorts with deeded Echo Lake access. This is a rare find! This 2.2+/- acre lot has an installed mound system for a permitted wastewater system for a four-bedroom home. Lot has been partially cleared and has the beginnings of a driveway. The deeded access on Echo Lake is a quick drive from the lot and provides

  Mendi Michael Engel & Völkers Okemo

  000 Echo View Dr, Plymouth, VT 05149
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  /25

  Not Listed For Sale

  00 Chapman Rd, Plymouth, VT 05056

  00 Chapman Rd, Plymouth, VT 05056
• 

  

  /37

  $469,000

  • 4 Beds
  • 3 Baths
  • 1,920 Sq Ft

  1226 E Ash Rd Unit L-34, Plymouth, VT 05056

  Mountain Retreat in Plymouth – Between Killington & OkemoWelcome to your Vermont getaway! This spacious four-bedroom, three-bathroom condo is nestled in the scenic hills of Plymouth, perfectly located between Killington and Okemo for easy access to world-class skiing, snowboarding and year-round mountain and lake adventures.Enjoy breathtaking winter views from this top-level,

  Katie McFadden RE/MAX North Professionals

  1226 E Ash Rd Unit L-34, Plymouth, VT 05056
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  /15

  $80,000 Sold Apr 25, 2025

  • Land
  • 3.02 Acres
  • $26,490 per Acre

  • 329 Days On Market

  Lot 4 Echo View Dr, Plymouth, VT 05149

  Ideally located between Okemo and Killington, this 3-acre lot has view potential with clearing. This parcel has a four-bedroom wastewater permit and deeded shared access to 100 feet of frontage on Echo Lake. Perfect location to build your four-season home! View photos were taken a few years ago when leaves were off the deciduous trees.

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  Lot 4 Echo View Dr, Plymouth, VT 05149
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  /25

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 994 Sq Ft

  145 Blueberry Ledge Ridge Unit L-48, Plymouth, VT 05056

  145 Blueberry Ledge Ridge Unit L-48, Plymouth, VT 05056
• 

  

  /60

  $4,850,000

  • 5 Beds
  • 6 Baths
  • 6,313 Sq Ft

  476 Salt Ash Rd, Plymouth, VT 05056

  Serena Lodge was inspired by the legendary William Rockefeller estate in the Adirondacks, known as The Point, and thoughtfully designed to reflect its inviting look and warm, rustic elegance. This 9,000+ square foot residence sits atop a knoll beside a lively creek with small waterfalls, creating a peaceful, natural soundtrack.The Great Room is the centerpiece of the home, with a soaring

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  476 Salt Ash Rd, Plymouth, VT 05056
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  /48

  $650,000 Sold Apr 18, 2025

  • 2,030 Sq Ft
  • $320/SF
  • 8 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1987

  529 E Ash Rd, Plymouth, VT 05056

  Tucked away in the peaceful setting of Hawk Resort, this well-maintained 4-bedroom, 4-bath home offers a comfortable retreat in every season. Designed to complement its natural surroundings, the home features an open and bright main floor with cathedral ceilings, skylights, and large windows that bring in plenty of natural light. Wide pine floors and a beautiful stone fireplace add warmth and

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  529 E Ash Rd, Plymouth, VT 05056
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  /32

  Est $397,093 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,727 Sq Ft

  1787 Route 100 N, Ludlow, VT 05149

  1787 Route 100 N, Ludlow, VT 05149
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  /7

  $35,000

  • Land
  • 1.71 Acres
  • $20,468 per Acre

  2-49 E Ash Rd, Plymouth, VT 05056

  Looking for an ideal piece of land to build your forever home? If so, don't miss out on this stunning 1.71 acres of land with mountain views! Located on a quiet road this peaceful property offers tons of privacy and views of the VT mountains and the beautiful forestry all around you. Just a short drive off of the main road VT route 100 that takes you easily to all the surrounding attractions and

  Daniel Preston KW Vermont Woodstock

  2-49 E Ash Rd, Plymouth, VT 05056
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  /34

  $475,000 Sold Apr 17, 2025

  • 2,474 Sq Ft
  • $192/SF
  • 13 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1920

  5534 Route 100, Plymouth, VT 05056

  Attention Skiers and Snowmobilers! This newly updated, open concept 3 bedroom plus den, 2 full bathroom vacation retreat is minutes to Killington, Okemo or Woodstock. Conveniently located off of scenic Vermont Route 100 on 7.9 +/- acres with direct access to VAST Snowmobile Trails from the property. The property is situated across the street from Chloe's Market/ Plymouth Country Store to walk and

  Marni Rieger KW Vermont-Killington

  5534 Route 100, Plymouth, VT 05056

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