Andover, VT Homes

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  /16

  $3,150,000

  • Land
  • 506 Acres
  • $6,225 per Acre

  Markham Mountain, Andover, VT 05143

  Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence.This land's historical roots run deep, originally belonging to the Marsh

  Story Jenks LANDVEST

  Markham Mountain, Andover, VT 05143
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  /42

  $415,000 Sold Mar 30, 2026

  1979 N Hill Rd, Chester, VT 05143

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • Built 2005

  Last Sold Summary

  • 10% Below List Price
  • $222/SF
  • 113 Days On Market

  Current Estimated Value $422,667

  Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  1979 N Hill Rd, Chester, VT 05143
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  /29

  Est $331,711 Not Listed For Sale

  201 Hill Top Rd, Chester, VT 05143

  • 3 Beds
  • 1 Bath
  • 1,137 Sq Ft
  • Built 1983

  201 Hill Top Rd, Chester, VT 05143

  Last Sold Summary

  • 2% Above List Price
  • $286/SF
  • 18 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home
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  /16

  $3,150,000

  • Land
  • 506 Acres
  • $6,225 per Acre

  00 Marsh Cross Rd, Andover, VT 05143

  Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence. This land's historical roots run deep, originally belonging to the Marsh

  Story Jenks LandVest, Inc/Woodstock

  00 Marsh Cross Rd, Andover, VT 05143
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  /52

  $598,000 Sold Oct 10, 2025

  2510 E Hill Rd, Chester, VT 05143

  • 3 Beds
  • 2.5 Baths
  • 2,264 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $264/SF
  • 94 Days On Market

  Current Estimated Value $578,215

  Last Listing Agent Betty McEnaney Diamond Realty

  2510 E Hill Rd, Chester, VT 05143
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  /40

  Est $584,600 Not Listed For Sale

  2656 Weston-Andover Rd, Chester, VT 05143

  • 3 Beds
  • 1 Bath
  • 2,080 Sq Ft
  • Built 2004

  2656 Weston-Andover Rd, Chester, VT 05143

  Last Sold Summary

  • 2% Below List Price
  • $286/SF
  • 55 Days On Market

  Last Sold Price $595,000

  Last Listing Agent Betty McEnaney Diamond Realty
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  /11

  $149,900

  • Land
  • 12.7 Acres
  • $11,803 per Acre

  360 Dorman Rd, Andover, VT 05143

  Discover the perfect blend of privacy, natural beauty, and convenience on this stunning 12.7-acre parcel nestled in the heart of the Green Mountains in Andover. This mostly wooded property offers a peaceful, secluded setting with a cleared homesite ideally positioned for southern exposure and the potential for breathtaking long-range mountain views with additional clearing.A 5-bedroom

  Gary Coger Four Seasons Sotheby's Int'l Realty

  360 Dorman Rd, Andover, VT 05143
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  /36

  $1,400,000 Sold Aug 27, 2025

  938 Stigers Rd, Chester, VT 05143

  • 3 Beds
  • 3.5 Baths
  • 2,614 Sq Ft
  • Built 2011

  Last Sold Summary

  • 15% Below List Price
  • $536/SF
  • 42 Days On Market

  Current Estimated Value $1,456,688

  Last Listing Agent Liz Moore Real Broker LLC

  938 Stigers Rd, Chester, VT 05143
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  /40

  Est $352,544 Not Listed For Sale

  42 Cobb Rd, Chester, VT 05143

  • 3 Beds
  • 1.5 Baths
  • 1,087 Sq Ft
  • Built 1965

  42 Cobb Rd, Chester, VT 05143

  Last Sold Summary

  • 1% Below List Price
  • $327/SF
  • 39 Days On Market

  Last Sold Price $355,000

  Last Listing Agent Geralyn Donohue Engel & Völkers Okemo
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  /15

  $85,000

  • Land
  • 4.05 Acres
  • $20,988 per Acre

  00 Hillcrest Dr, Andover, VT 05143

  Ready to Build in Southern Vermont! Dreaming of a serene mountain getaway or your forever home in Vermont? This 4.± acre gem on a quiet dead-end road offers peace, privacy, and convenience. With a State-issued wastewater permit already in hand for a 5-bedroom home, you can hit the ground running on your build. Power is right at the road and fiber-optic internet is available—ideal for remote work

  Daire Gibney Barrett and Valley Associates Inc.

  00 Hillcrest Dr, Andover, VT 05143
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  /37

  $600,000 Sold May 09, 2025

  43 Lee Way, Andover, VT 05143

  • 3 Beds
  • 3 Baths
  • 2,076 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $289/SF
  • 575 Days On Market

  Last Listing Agent Britt Wohler

  43 Lee Way, Andover, VT 05143
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  /35

  Est $427,148 Not Listed For Sale

  351 Lovejoy Brook Rd, Ludlow, VT 05149

  • 3 Beds
  • 2 Baths
  • 1,171 Sq Ft
  • Built 1975

  351 Lovejoy Brook Rd, Ludlow, VT 05149

  Last Sold Summary

  • $365/SF
  • 3 Days On Market

  Last Sold Price $427,000

  Last Listing Agent Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.
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  /19

  $595,000

  • Land
  • 220.11 Acres
  • $2,703 per Acre

  0 Markham Mountain Rd, Andover, VT 05143

  Discover 220± acres of pristine woodland offering the ultimate blend of privacy, recreation, and opportunity. With a mix of gently level terrain and elevated ridgelines that may offer sweeping mountain views, this remarkable parcel provides endless possibilities — from a private estate setting to potential subdivision. The VAST snowmobile trail runs directly through a portion of the property,

  Kevin Barnes William Raveis Real Estate Vermont Properties

  0 Markham Mountain Rd, Andover, VT 05143
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  /60

  $40,000 Sold Jul 11, 2025

  00 Boone Rd, Andover, VT 05143

  • Land
  • 5 Acres
  • $8,000 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 77 Days On Market

  Last Listing Agent Rachael Rogala Lange & Lange

  00 Boone Rd, Andover, VT 05143
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  /53

  Est $549,652 Not Listed For Sale

  566 Simonsville Rd, Chester, VT 05143

  • 3 Beds
  • 2.5 Baths
  • 2,650 Sq Ft
  • Built 1820

  566 Simonsville Rd, Chester, VT 05143

  Last Sold Summary

  • 10% Above List Price
  • $188/SF
  • 229 Days On Market

  Last Sold Price $499,000

  Last Listing Agent Geralyn Donohue Engel & Völkers Okemo
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  /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
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  /41

  $845,000 Sold Nov 20, 2025

  2904 E Hill Rd, Andover, VT 05143

  • 4 Beds
  • 4 Baths
  • 3,278 Sq Ft
  • Built 1989

  Last Sold Summary

  • 11% Below List Price
  • $258/SF
  • 78 Days On Market

  Last Listing Agent Steve Stettler Four Seasons Sotheby's Int'l Realty

  2904 E Hill Rd, Andover, VT 05143
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  /31

  Est $503,851 Not Listed For Sale

  345 Lovejoy Brook Rd, Ludlow, VT 05149

  • 3 Beds
  • 2 Baths
  • 2,311 Sq Ft
  • Built 1987

  345 Lovejoy Brook Rd, Ludlow, VT 05149

  Last Sold Summary

  • 8% Above List Price
  • $201/SF
  • 5 Days On Market

  Last Sold Price $465,000

  Last Listing Agent Gary Coger Four Seasons Sotheby's Int'l Realty
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  /48

  $899,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,172 Sq Ft

  1269 Howard Hill Rd, Chester, VT 05143

  Discover a truly one-of-a-kind Vermont retreat set on 10 acres of peaceful woodland and open meadow. Originally built as a family-run maple sugar shack, this architect-designed home has been thoughtfully reimagined and newly completed, seamlessly blending rustic charm with contemporary comfort to create a warm and inviting hideaway unlike anything else on the market. Post-and-beam construction,

  Cheyanne Pugliese

  1269 Howard Hill Rd, Chester, VT 05143
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  /2

  $290,000 Sold Dec 22, 2025

  26 Dorman Rd, Andover, VT 05143

  • 4 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1970

  Last Sold Summary

  • 19% Below List Price
  • $232/SF
  • 252 Days On Market

  Current Estimated Value $285,622

  Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  26 Dorman Rd, Andover, VT 05143
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  /39

  Est $488,541 Not Listed For Sale

  2358 N Hill Rd, Chester, VT 05143

  • 4 Beds
  • 3 Baths
  • 2,070 Sq Ft
  • Built 1975

  2358 N Hill Rd, Chester, VT 05143

  Last Sold Summary

  • 1% Above List Price
  • $235/SF
  • 6 Days On Market

  Last Sold Price $485,500

  Last Listing Agent John Napier TPW Real Estate
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  /11

  $85,000 Under Contract

  • Land
  • 15.68 Acres
  • $5,421 per Acre

  00 E Hill Rd, Andover, VT 05143

  Rooted in along scenic East Hill Road in the bucolic town of Andover, this 16-acre parcel offers a rare opportunity to create your own private haven in one of Southern Vermont’s most peaceful and charming settings. Just minutes from Ludlow and the slopes of Okemo Mountain, this location strikes the perfect balance between quiet countryside and convenient access to skiing, shopping, dining, and

  Daire Gibney Barrett and Valley Associates Inc.

  00 E Hill Rd, Andover, VT 05143
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  /24

  $330,000 Sold Oct 24, 2025

  1749 Middletown Rd, Andover, VT 05143

  • Land
  • 31 Acres
  • $10,645 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 86 Days On Market

  Current Estimated Value $320,137

  Last Listing Agent Gary Coger Four Seasons Sotheby's Int'l Realty

  1749 Middletown Rd, Andover, VT 05143
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  /38

  Est $731,682 Not Listed For Sale

  2401 N Hill Rd, Chester, VT 05143

  • 4 Beds
  • 2.5 Baths
  • 2,242 Sq Ft
  • Built 1990

  2401 N Hill Rd, Chester, VT 05143

  Last Sold Summary

  • 2% Below List Price
  • $335/SF
  • 67 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Alison Cummings Cummings & Co
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  /60

  $889,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 3,310 Sq Ft

  201 Spruce Dr, Chester, VT 05143

  Situated on over five acres of rolling Vermont hillside, this three-bedroom, two-bath home offers effortless access to Okemo Mountain Resort, Stratton Mountain Resort, Bromley Mountain, and Magic Mountain Ski Area, and is being sold turnkey. Designed for those who value both comfort and connection to the outdoors, this property is a true four-season retreat. In winter, enjoy world-class skiing

  Mendi Michael Engel & Völkers Okemo

  201 Spruce Dr, Chester, VT 05143
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  /21

  $105,000 Sold Dec 19, 2025

  00 Hill Top Rd, Andover, VT 05143

  • Land
  • 13.34 Acres
  • $7,871 per Acre

  Last Sold Summary

  • 22% Below List Price
  • 275 Days On Market

  Last Listing Agent Flex Realty Group Flex Realty

  00 Hill Top Rd, Andover, VT 05143
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  /10

  Not Listed For Sale

  0 Spruce Dr Unit 4973323, Andover, VT 05143

  0 Spruce Dr Unit 4973323, Andover, VT 05143

  Last Sold Summary

  • 468 Days On Market

  Last Sold Price $150,000

  Last Listing Agent Alan DeAngelo Element Real Estate
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  /21

  $150,000

  • Land
  • 13.96 Acres
  • $10,745 per Acre

  0 Valley View Dr Unit 5009431, Andover, VT 05143

  Great Value in a great setting ! Bordering the Ludlow line and set at an elevation of 2,000+ feet, this exceptional parcel offers privacy, expansive long-range views, and an ideal setting for your Southern Vermont dream home. Located within a peaceful community of fine homes, this is one of the few remaining opportunities to build in this highly desirable area. The property includes a

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  0 Valley View Dr Unit 5009431, Andover, VT 05143
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  /2

  $792,000 Sold Jul 15, 2025

  1295 Middletown Rd, Chester, VT 05143

  • 3 Beds
  • 3.5 Baths
  • 3,614 Sq Ft
  • Built 2012

  Last Sold Summary

  • 7% Below List Price
  • $219/SF
  • 0 Days On Market

  Current Estimated Value $775,610

  Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

  1295 Middletown Rd, Chester, VT 05143
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  /30

  Not Listed For Sale

  3011 A East Hill Rd, Andover, VT 05143

  • 3 Beds
  • 3 Baths
  • 1,504 Sq Ft
  • Built 1976

  3011 A East Hill Rd, Andover, VT 05143

  Last Sold Summary

  • $455/SF
  • 88 Days On Market

  Last Sold Price $685,000

  Last Listing Agent Steve Stettler Four Seasons Sotheby's Int'l Realty
• 

  

  /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, Vermont Discover 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 property

  Daire Gibney Barrett and Valley Associates Inc.

  000 Green Mountain Turnpike, Andover, VT 05143
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  /54

  $540,000 Sold May 23, 2025

  316 Little Pond Rd, Chester, VT 05143

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1975

  Last Sold Summary

  • $371/SF
  • 32 Days On Market

  Current Estimated Value $531,066

  Last Listing Agent Nick Sicard EXP Realty

  316 Little Pond Rd, Chester, VT 05143
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  /21

  Est $392,838 Not Listed For Sale

  1004 Williams Dr Unit 3, Middletown, PA 17057

  • 3 Beds
  • 2.5 Baths
  • 1,930 Sq Ft
  • Built 2024

  1004 Williams Dr Unit 3, Middletown, PA 17057

  Last Sold Summary

  • 2% Below List Price
  • $207/SF
  • 84 Days On Market

  Last Sold Price $398,990

  Last Listing Agent Jayson Quon Berks Homes Realty, LLC
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  /17

  $485,000

  • Land
  • 26.99 Acres
  • $17,970 per Acre

  00 Valley View Dr, Andover, VT 05143

  A premier location abutting the Ludlow border, close to Okemo with total privacy, long range panoramic views of distant mountains and valleys at an elevation of about 2000 feet. Peace and beauty abound yet easy access to all area amenities including skiing, golf, biking, hiking and all that Southern Vermont has to offer. A State wastewater permit is in place for a 6 bedroom home and a 2 bedroom

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  00 Valley View Dr, Andover, VT 05143
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  /28

  $450,000 Sold Nov 14, 2025

  1809 Marsh Hill Rd, Andover, VT 05143

  • Land
  • 57.2 Acres
  • $7,867 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 73 Days On Market

  Current Estimated Value $454,810

  Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

  1809 Marsh Hill Rd, Andover, VT 05143
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  /18

  Est $135,868 Not Listed For Sale

  2267 N Hill Rd, Andover, VT 05143

  2267 N Hill Rd, Andover, VT 05143

  Last Sold Summary

  • 1% Above List Price
  • 45 Days On Market

  Last Sold Price $135,000

  Last Listing Agent John Napier TPW Real Estate
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  /41

  $5,950,000

  • 8 Beds
  • 7.5 Baths
  • 10,062 Sq Ft

  3800 Weston-Andover Rd, Andover, VT 05143

  The ultimate family compound, award nominated video tour. This fully furnished and equipped luxury property is located in Andover, Vermont, set on 384 acres in the iconic Green Mountains, offering a rare blend of nature’s bounty, seclusion, and timeless craftsmanship. The custom built 10,062 square foot main house features an expansive open concept design. Crafted with post and beam timber frame

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  3800 Weston-Andover Rd, Andover, VT 05143
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  /32

  $1,510,000 Sold Dec 22, 2025

  611 Simmons Rd, Chester, VT 05143

  • 2 Beds
  • 4 Baths
  • 3,514 Sq Ft
  • Built 1965

  Last Sold Summary

  • 33% Below List Price
  • $430/SF
  • 151 Days On Market

  Current Estimated Value $1,647,781

  Last Listing Agent Dia Jenks LandVest, Inc/Woodstock

  611 Simmons Rd, Chester, VT 05143
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  /13

  Not Listed For Sale

  Lot 49 Andover Ridge Rd Unit 49, Andover, VT 05143

  Lot 49 Andover Ridge Rd Unit 49, Andover, VT 05143

  Last Sold Summary

  • 254 Days On Market

  Last Sold Price $125,000

  Last Listing Agent Erica Reynolds Southern Vermont Realty Group
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  /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

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