Jamaica, VT Homes

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  /54

  $639,900

  • 3 Beds
  • 3 Baths
  • 2,700 Sq Ft

  98 Gleason Farm Ln, Jamaica, VT 05343

  Nestled within a peaceful pine grove on 11.5 private acres between Stratton Mountain Resort and Mount Snow, this renovated 3-bedroom, 3-bathroom residence offers the perfect blend of secluded Vermont beauty and modern design. The heart of the home is a dramatic great room featuring 20+ foot soaring ceilings, skylights, and expansive windows that flood the space with natural light. On chilly

  

  Lauren Behm

  Berkshire Hathaway HomeServices Stratton Home

  (802) 988-7628

  98 Gleason Farm Ln, Jamaica, VT 05343
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  /29

  $18,000 per month

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • House for Rent

  67 Vermont Route 100, Jamaica, VT 05155

  Discover the charm of this delightful rental nestled along a quintessential river in Vermont! With its prime location on a major road, you're just 7 miles away from the slopes of the Stratton Mountain ski resort, making it the perfect getaway for winter sports enthusiasts. This spacious home boasts multiple living areas, ensuring everyone has their own space to relax and unwind. With four

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  67 Vermont Route 100, Jamaica, VT 05155
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  $125,000 Sold Dec 11, 2025

  0 Dalewood Rd Unit 4955807, Jamaica, VT 05343

  • Land
  • 1.51 Acres
  • $82,781 per Acre

  Last Sold Summary

  • 880 Days On Market

  Last Listing Agent Mike England Michael England Real Estate

  0 Dalewood Rd Unit 4955807, Jamaica, VT 05343
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  Est $431,203 Not Listed For Sale

  559 Pratt Bridge Rd, Jamaica, VT 05343

  • 4 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1978

  559 Pratt Bridge Rd, Jamaica, VT 05343

  Last Sold Summary

  • 5% Above List Price
  • $333/SF
  • 181 Days On Market

  Last Sold Price $410,000

  Last Listing Agent Joe Castaluccio Winhall Real Estate
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  /35

  $2,399,000

  • 4 Beds
  • 4.5 Baths
  • 3,569 Sq Ft

  662 Howe Farm Rd, Jamaica, VT 05343

  Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  662 Howe Farm Rd, Jamaica, VT 05343
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  $6,000 per month

  • 5 Beds
  • 3 Baths
  • 2,912 Sq Ft
  • House for Rent

  1138 River Rd, Jamaica, VT 05343

  WINTER MONTHLY RENTAL - $6,000/Month Plus prepaid utilities ($750/month) | Total due in Full Before Occupancy. Spend the winter in the mountains with this spacious and fully updated 5-bedroom, 3-bath home with a cozy loft in scenic Jamaica, VT. Nestled in a quiet wooded setting, this inviting retreat comfortably accommodates up to 12 guests. After a day on the slopes, relax by the fireplace with

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1138 River Rd, Jamaica, VT 05343
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  $200,000 Sold Oct 17, 2025

  533 Pratt Bridge Rd, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 2,613 Sq Ft
  • Built 1970

  Last Sold Summary

  • 27% Below List Price
  • $77/SF
  • 25 Days On Market

  Current Estimated Value $236,326

  Last Listing Agent Mike England Michael England Real Estate

  533 Pratt Bridge Rd, Jamaica, VT 05343
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  Est $472,927 Not Listed For Sale

  476 Edie Ln, Jamaica, VT 05343

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft
  • Built 1988

  476 Edie Ln, Jamaica, VT 05343

  Last Sold Summary

  • 5% Above List Price
  • $249/SF
  • 40 Days On Market

  Last Sold Price $449,000

  Last Listing Agent Carrie Mathews Winhall Real Estate
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  /60

  $849,000

  • 5 Beds
  • 4.5 Baths
  • 3,840 Sq Ft

  42 Blackberry Ln, Jamaica, VT 05343

  Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living

  MaryKate Grey Stratton Real Estate

  42 Blackberry Ln, Jamaica, VT 05343
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  /14

  $2,500 per month

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • House for Rent

  4591 Vermont 30, Jamaica, VT 05343

  ITS NOT TOO LATE.. SNOW IS JUST STARTING TO FLY..This is a delightful Winter retreat...After a long fun day of skiing come home to this warm and cozy, meticulously maintained 4 bedroom home that is in great shape. Just 8 minutes from Stratton access Rd.Upstairs there are 2.5 bedrooms , kitchen, and living room with wood burning fireplace. Downstairs is another full bedroom and a 2nd kitchen,

  Wilkie Bushby TPW Real Estate

  4591 Vermont 30, Jamaica, VT 05343
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  /46

  $299,000 Sold Jan 22, 2026

  4410 Pikes Falls Rd, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 2,194 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Below List Price
  • $136/SF
  • 5 Days On Market

  Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  4410 Pikes Falls Rd, Jamaica, VT 05343
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  Est $462,542 Not Listed For Sale

  3796 Vt Route 30, Jamaica, VT 05343

  • 4 Beds
  • 1.5 Baths
  • 3,169 Sq Ft
  • Built 1860

  3796 Vt Route 30, Jamaica, VT 05343

  Last Sold Summary

  • 25% Above List Price
  • $117/SF
  • 7 Days On Market

  Last Sold Price $371,195

  Last Listing Agent Jacki Murano Southern Vermont Realty Group
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  /8

  $275,000 Under Contract

  • Land
  • 34.53 Acres
  • $7,964 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need to be

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /31

  $405,000 Sold Mar 05, 2026

  132 Pratt Bridge Rd, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft
  • Built 1987

  Last Sold Summary

  • 13% Below List Price
  • $223/SF
  • 140 Days On Market

  Current Estimated Value $444,102

  Last Listing Agent Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  132 Pratt Bridge Rd, Jamaica, VT 05343
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  Est $395,409 Not Listed For Sale

  3996 Vt Route 30, Jamaica, VT 05343

  • 4 Beds
  • 3 Baths
  • 3,081 Sq Ft
  • Built 1850

  3996 Vt Route 30, Jamaica, VT 05343

  Last Sold Summary

  • 5% Above List Price
  • $122/SF
  • 133 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Britt Wohler
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  /11

  $495,000 Under Contract

  • Land
  • 68.89 Acres
  • $7,185 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a solid woods

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  $1,300,000 Sold Jul 31, 2025

  0 W Hill Rd S Unit 5006431, Jamaica, VT 05343

  • Land
  • 591 Acres
  • $2,200 per Acre

  Last Sold Summary

  • 32% Below List Price
  • 136 Days On Market

  Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

  0 W Hill Rd S Unit 5006431, Jamaica, VT 05343
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  Est $294,656 Not Listed For Sale

  3790 S Hill Rd, Jamaica, VT 05343

  • 2 Beds
  • 1 Bath
  • 576 Sq Ft
  • Built 1960

  3790 S Hill Rd, Jamaica, VT 05343

  Last Sold Summary

  • 9% Below List Price
  • $564/SF
  • 80 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Mike England Michael England Real Estate
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  /7

  $195,000 Under Contract

  • Land
  • 15.27 Acres
  • $12,770 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /30

  $1,000,000 Sold Jan 30, 2026

  585 Pleasant Valley Rd, Jamaica, VT 05343

  • Land
  • 108 Acres
  • $9,259 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 293 Days On Market

  Current Estimated Value $1,013,711

  Last Listing Agent Britt Wohler

  585 Pleasant Valley Rd, Jamaica, VT 05343
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  /18

  Est $568,428 Not Listed For Sale

  155 Pratt Bridge Rd, Jamaica, VT 05343

  • 4 Beds
  • 2.5 Baths
  • 2,050 Sq Ft
  • Built 1971

  155 Pratt Bridge Rd, Jamaica, VT 05343

  Last Sold Summary

  • 11% Above List Price
  • $249/SF
  • 3 Days On Market

  Last Sold Price $510,000

  Last Listing Agent Kevin Moran Four Seasons Sotheby's Int'l Realty
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  /15

  $650,000 Under Contract

  • Land
  • 51.93 Acres
  • $12,517 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very unique, and

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  /43

  $887,000 Sold Oct 17, 2025

  460 Stratton Gate Rd, Jamaica, VT 05343

  • 4 Beds
  • 3 Baths
  • 3,155 Sq Ft
  • Built 1992

  Last Sold Summary

  • 1% Below List Price
  • $281/SF
  • 12 Days On Market

  Current Estimated Value $975,095

  Last Listing Agent Helen Nault

  460 Stratton Gate Rd, Jamaica, VT 05343
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  /40

  Est $955,104 Not Listed For Sale

  1223 Cole Pond Rd, Jamaica, VT 05343

  • 3 Beds
  • 4 Baths
  • 2,197 Sq Ft
  • Built 1970

  1223 Cole Pond Rd, Jamaica, VT 05343

  Last Sold Summary

  • 1% Above List Price
  • $432/SF
  • 7 Days On Market

  Last Sold Price $950,000

  Last Listing Agent Karin Hardy Berkshire Hathaway HomeServices Stratton Home
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  $1,450,000

  • 5 Beds
  • 3.5 Baths
  • 3,040 Sq Ft

  4427 W Hill Rd S, Jamaica, VT 05343

  One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want—an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two

  Carrie Mathews Winhall Real Estate

  4427 W Hill Rd S, Jamaica, VT 05343
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  /27

  $245,000 Sold Nov 14, 2025

  8365 Vermont 30, Jamaica, VT 05343

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft
  • Built 1967

  Last Sold Summary

  • 2% Below List Price
  • $324/SF
  • 0 Days On Market

  Last Listing Agent TG Glazer Winhall Real Estate

  8365 Vermont 30, Jamaica, VT 05343
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  Est $433,054 Not Listed For Sale

  1706 Vt Route 30, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 848 Sq Ft
  • Built 1967

  1706 Vt Route 30, Jamaica, VT 05343

  Last Sold Summary

  • 14% Below List Price
  • $591/SF
  • 6 Days On Market

  Last Sold Price $501,000

  Last Listing Agent Christopher Cummings Cummings & Co
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  $1,140,000

  • 4 Beds
  • 3 Baths
  • 4,193 Sq Ft

  70 Hunter Ln, Jamaica, VT 05343

  Discover a truly special Vermont retreat at 70 Hunter Lane, nestled in the private Cole Pond community of Jamaica. This exceptional residence offers over 4,200 square feet of living space, thoughtfully designed to blend comfort, luxury, and the natural beauty of its surroundings. Newer Stainless Steel appliances in kitchen! Featuring four spacious bedrooms, this home provides plenty of room for

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  70 Hunter Ln, Jamaica, VT 05343
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  /30

  $510,000 Sold Jun 05, 2025

  5600 Pikes Falls Rd, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 1,459 Sq Ft
  • Built 1977

  Last Sold Summary

  • 24% Below List Price
  • $350/SF
  • 170 Days On Market

  Current Estimated Value $637,305

  Last Listing Agent Jamie Wylie Stratton Real Estate

  5600 Pikes Falls Rd, Jamaica, VT 05343
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  Est $290,000 Not Listed For Sale

  192 Howe Farm Rd, Jamaica, VT 05343

  • 1 Bed
  • 1 Bath
  • 956 Sq Ft
  • Built 1963

  192 Howe Farm Rd, Jamaica, VT 05343

  Last Sold Summary

  • 5% Above List Price
  • $288/SF
  • 3 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Alison Cummings Cummings & Co
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  $860,000

  • 4 Beds
  • 3.5 Baths
  • 4,104 Sq Ft

  25 Benson Fuller Dr, Jamaica, VT 05343

  Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape.Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Jamaica, VT 05343
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  $785,000 Sold Nov 21, 2025

  202 Pratt Bridge Rd, Jamaica, VT 05343

  • 3 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • Built 1966

  Last Sold Summary

  • 1% Below List Price
  • $280/SF
  • 28 Days On Market

  Current Estimated Value $752,095

  Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  202 Pratt Bridge Rd, Jamaica, VT 05343
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  Est $375,199 Not Listed For Sale

  60 River Rd, Jamaica, VT 05343

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 1977

  60 River Rd, Jamaica, VT 05343

  Last Sold Summary

  • 60% Above List Price
  • $111/SF
  • 171 Days On Market

  Last Sold Price $234,000

  Last Listing Agent Jacki Murano Southern Vermont Realty Group
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  /39

  $890,000

  • 5 Beds
  • 3.5 Baths
  • 3,218 Sq Ft

  4880 Pikes Falls Rd, Jamaica, VT 05343

  This majestic log home offers peaceful mountain living with room for Everyone. Discover your tranquil 5-bedroom, 4-bathroom family retreat nestled just minutes from the year-round activities at Stratton Ski Resort. This authentic and expansive log cabin exudes classic Vermont charm. The inviting main living area is flooded with natural light, featuring an efficient wood stove to provide cozy

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  4880 Pikes Falls Rd, Jamaica, VT 05343
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  $170,000 Sold Nov 07, 2025

  440 Edie Ln, Jamaica, VT 05343

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • Built 1971

  Last Sold Summary

  • 19% Below List Price
  • $81/SF
  • 16 Days On Market

  Current Estimated Value $241,932

  Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

  440 Edie Ln, Jamaica, VT 05343
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  Not Listed For Sale

  498 Goodaleville Rd, South Londonderry, VT 05155

  • 8 Beds
  • 6 Baths
  • 4,600 Sq Ft
  • Built 1860

  498 Goodaleville Rd, South Londonderry, VT 05155

  Last Sold Summary

  • $239/SF
  • 22 Days On Market

  Last Sold Price $1,100,000

  Last Listing Agent Christiane Carroccio TPW Real Estate
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  /30

  $1,040,000

  • 5 Beds
  • 4.5 Baths
  • 3,363 Sq Ft

  1189 Cole Pond Rd, Jamaica, VT 05343

  Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts. The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1189 Cole Pond Rd, Jamaica, VT 05343
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  $64,000 Sold Sep 29, 2025

  2080 Vermont 30, Jamaica, VT 05343

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1975

  Last Sold Summary

  • 8% Below List Price
  • $68/SF
  • 5 Days On Market

  Last Listing Agent TG Glazer Winhall Real Estate

  2080 Vermont 30, Jamaica, VT 05343
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  /40

  Est $572,473 Not Listed For Sale

  886 Dalewood Rd, Jamaica, VT 05343

  • 3 Beds
  • 2.5 Baths
  • 768 Sq Ft
  • Built 1965

  886 Dalewood Rd, Jamaica, VT 05343

  Last Sold Summary

  • 20% Below List Price
  • $931/SF
  • 3 Days On Market

  Last Sold Price $715,000

  Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home
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  $650,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,370 Sq Ft

  5 Linscott Rd, Jamaica, VT 05343

  PRICE ADJUSTMENT to $650,000.This irresistible renovated Forest Farms contemporary with 3 bedrooms and 2 and a half baths has an inviting ambiance as well as appealing floor plan flow. Past the foyer with half bath is the open living concept with white oak hardwood floors. The glow and warmth of the raised hearth stone fireplace in the living area is shared from windowed dining area to bright

  Diana Stugger Four Seasons Sotheby's Int'l Realty

  5 Linscott Rd, Jamaica, VT 05343

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