2,598

Chester, VT Homes

Section Image
  • /2

    $50,000

    Sold Oct 10, 2025

    Lot 1 Old Stage Rd, Chester, VT 05143

    • Land
    • 3.5 Acres
    • $14,286 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 9 Days On Market

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    Lot 1 Old Stage Rd, Chester, VT 05143
    • /39

      Est $377,251

      Not Listed For Sale

      43 Northfield Dr, North Springfield, VT 05150

      • 3 Beds
      • 1.5 Baths
      • 2,085 Sq Ft
      • Built 1993
      43 Northfield Dr, North Springfield, VT 05150

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • /58

    $900,000

    $25K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,800 Sq Ft

    1470 Popple Dungeon Rd, Chester, VT 05143

    Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic

    Joseph Karl William Raveis Real Estate Vermont Properties

    1470 Popple Dungeon Rd, Chester, VT 05143
  • /14

    $140,000

    Sold Oct 23, 2025

    515 Main St, Chester, VT 05143

    • 3,024 Sq Ft
    • Built 1850

    Last Sold Summary

    • 17% Below List Price
    • $46/SF
    • 422 Days On Market

    Last Listing Agent John Tolosky Barrett and Valley Associates Inc.

    515 Main St, Chester, VT 05143
    • /16

      Est $280,464

      Not Listed For Sale

      192 Kevadus Cir, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1983
      192 Kevadus Cir, Chester, VT 05143

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • /47

    $610,000

    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft

    548 Crow Hill Rd, Chester, VT 05143

    Tucked away on a quiet country road, this well-maintained 4-bedroom Cape home offers the peaceful Vermont setting so many buyers are searching for.Set on 12.86 acres, the property has been a place where generations have gathered, and now it's ready for its next chapter. Thoughtfully updated and meticulously cared for, the home features a new roof along with numerous improvements that provide

    Jay Farrar Four Seasons Sotheby's Int'l Realty

    548 Crow Hill Rd, Chester, VT 05143
  • /59

    $730,000

    Sold Aug 28, 2026

    955 Smokeshire Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,695 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $431/SF
    • 13 Days On Market

    Current Estimated Value $752,184

    Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

    955 Smokeshire Rd, Chester, VT 05143
    • /37

      Est $270,637

      Not Listed For Sale

      468 Vt Route 103 S, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1940
      468 Vt Route 103 S, Chester, VT 05143

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Frank Provance Diamond Realty

  • /9

    $119,000

    $10K PRICE DROP
    • Land
    • 7.95 Acres
    • $14,969 per Acre

    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143

    Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, beauty, and potential. Wander through a peaceful forest where moss covered stones, classic Vermont stone walls, and soft woodland light create a truly serene setting. With some thoughtful clearing, this parcel could open up to stunning views overlooking the charming fields and

    Thaddeus Abare Barrett and Valley Associates Inc.

    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
  • /53

    $359,000

    Sold May 15, 2026

    531 Main St, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 1,608 Sq Ft
    • Built 1880

    Last Sold Summary

    • 16% Below List Price
    • $223/SF
    • 115 Days On Market

    Current Estimated Value $351,875

    Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

    531 Main St, Chester, VT 05143
    • /18

      Est $435,178

      Not Listed For Sale

      183 Pleasant St, Chester, VT 05143

      • 4 Beds
      • 2.5 Baths
      • 2,686 Sq Ft
      • Built 1880
      183 Pleasant St, Chester, VT 05143

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /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
  • /23

    $195,000

    Sold Dec 10, 2025

    1833 Mattson Rd, Chester, VT 05143

    • 2 Beds
    • 2.5 Baths
    • 1,640 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Below List Price
    • $119/SF
    • 3 Days On Market

    Current Estimated Value $196,769

    Last Listing Agent Mike Masters Four Seasons Sotheby's Int'l Realty

    1833 Mattson Rd, Chester, VT 05143
    • /34

      Est $465,721

      Not Listed For Sale

      405 Church St, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,856 Sq Ft
      • Built 1967
      405 Church St, Chester, VT 05143

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  • /24

    $74,500

    Under Contract
    • Land
    • 16.24 Acres
    • $4,587 per Acre

    TBD Farrar Rd, Chester, VT 05143

    Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This piece is a clean slate that could be any of that! It has gentle slopes and flats for a potential building spots. Wooded and private, while being a short drive into lovely Chester, VT. This beautiful lot has so much potential, come take a look!

    Erin Kendall EXP Realty

    TBD Farrar Rd, Chester, VT 05143
  • /42

    $359,000

    Sold Nov 05, 2025

    1470 Flamstead Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 803 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Above List Price
    • $447/SF
    • 12 Days On Market

    Current Estimated Value $363,687

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1470 Flamstead Rd, Chester, VT 05143
    • /48

      Est $433,869

      Not Listed For Sale

      102 Church St, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 1,990 Sq Ft
      • Built 1895
      102 Church St, Chester, VT 05143

      Last Sold Summary

      • 142 Days On Market

      Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  • /22

    $100,000

    • Land
    • 23,958 Sq Ft
    • $181,818 per Acre

    427 Depot St, Chester, VT 05143

    Situated in the heart of Chester, Vermont, this 0.55-acre parcel offers approximately 254 feet of frontage on Depot Street and 254 feet of frontage on First Avenue - both public, paved roads with a sidewalk accessible on Depot Street. The land is open, landscaped, and dotted with apple trees, creating a welcoming setting for your future plans. Town water and town sewer are available at the

    Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

    427 Depot St, Chester, VT 05143
  • /56

    $805,000

    Sold Jan 13, 2026

    1342 Old Stage Rd, Chester, VT 05143

    • 2 Beds
    • 2 Baths
    • 1,576 Sq Ft
    • Built 1971

    Last Sold Summary

    • 10% Below List Price
    • $511/SF
    • 97 Days On Market

    Current Estimated Value $801,853

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    1342 Old Stage Rd, Chester, VT 05143
    • /28

      Est $255,287

      Not Listed For Sale

      386 1st Ave, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 943 Sq Ft
      • Built 1960
      386 1st Ave, Chester, VT 05143

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Julie Buffum Buffum Realty

  • /60

    $250,000

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    3781 Flamstead Rd, Chester, VT 05143

    Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An

    Amy Hill EXP Realty

    3781 Flamstead Rd, Chester, VT 05143
  • /23

    $59,000

    Sold Oct 08, 2025

    58 Remington Rd, Chester, VT 05143

    • Land
    • 2.86 Acres
    • $20,629 per Acre

    Last Sold Summary

    • 25% Below List Price
    • 169 Days On Market

    Current Estimated Value $58,560

    Last Listing Agent John Napier TPW Real Estate

    58 Remington Rd, Chester, VT 05143
    • /40

      Est $484,998

      Not Listed For Sale

      595 Main St, Chester, VT 05143

      • 6 Beds
      • 3 Baths
      • 3,892 Sq Ft
      • Built 1988
      595 Main St, Chester, VT 05143

      Last Sold Summary

      • 7 Days On Market

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

  • /25

    $229,000

    • Land
    • 27.8 Acres
    • $8,237 per Acre

    00 Quarry Rd, Chester, VT 05143

    27.8 +/- acre wooded parcel close to Chester Village with beautiful views. Driveway is roughed in and a clearing prepared at the entry to the land for a house site and a Vt state approved 4 bedroom wastewater Permit. Newly opened views from the plateau along the ridge accessed by an established logging road are a must see. Soil tests indicate a 3 bedroom home site is possible at the scenic

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    00 Quarry Rd, Chester, VT 05143
  • /27

    $178,000

    Sold Nov 05, 2025

    284 Flamstead Rd, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Built 1969

    Last Sold Summary

    • 6% Below List Price
    • $185/SF
    • 9 Days On Market

    Current Estimated Value $200,839

    Last Listing Agent Linda Benoit Highland Realty

    284 Flamstead Rd, Chester, VT 05143
    • /34

      Est $368,483

      Not Listed For Sale

      489 Main St, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 2,220 Sq Ft
      • Built 1860
      489 Main St, Chester, VT 05143

      Last Sold Summary

      • 10 Days On Market

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

  • /38

    $249,500

    • 1,922 Sq Ft

    3668 Vt Route 103 N, Chester, VT 05143

    Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits.The home is currently configured as two charming

    Daniel Vigeant Mary W. Davis Realtor & Assoc., Inc.

    3668 Vt Route 103 N, Chester, VT 05143
  • /49

    $950,000

    Sold Dec 05, 2025

    1847 Trebo Rd, Chester, VT 05143

    • 4 Beds
    • 4 Baths
    • 3,920 Sq Ft
    • Built 1849

    Last Sold Summary

    • 19% Below List Price
    • $242/SF
    • 127 Days On Market

    Current Estimated Value $680,089

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

    1847 Trebo Rd, Chester, VT 05143
    • /24

      Est $561,172

      Not Listed For Sale

      548 Main St, Chester, VT 05143

      • 4 Beds
      • 3 Baths
      • 2,622 Sq Ft
      • Built 1841
      548 Main St, Chester, VT 05143

      Last Sold Summary

      • 4 Days On Market

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

  • /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
  • /53

    $550,000

    Sold Oct 06, 2025

    1937 Green Mountain Turnpike, Chester, VT 05143

    • 2 Beds
    • 2 Baths
    • 1,812 Sq Ft
    • Built 1864

    Last Sold Summary

    • 3% Below List Price
    • $304/SF
    • 6 Days On Market

    Current Estimated Value $548,269

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    1937 Green Mountain Turnpike, Chester, VT 05143
    • /36

      Est $438,214

      Not Listed For Sale

      115 Orcutt Dr, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 1,360 Sq Ft
      • Built 1955
      115 Orcutt Dr, Chester, VT 05143

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • /60

    $879,999

    $9K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 3,310 Sq Ft

    201 Spruce Dr, Chester, VT 05143

    Set on over five acres of rolling Vermont hillside, this three-bedroom, two-bath home is perfectly positioned for year-round enjoyment with a special focus on summer living and seamless access to some of southern Vermont’s top mountain destinations, including Okemo Mountain Resort, Stratton Mountain Resort, Bromley Mountain, and Magic Mountain Ski Area. Offered turnkey, it’s an ideal basecamp for

    Mendi Michael Engel & Völkers Okemo

    201 Spruce Dr, Chester, VT 05143
  • /10

    $129,000

    Sold Feb 24, 2026

    469 Williams Rd, Chester, VT 05143

    • Land
    • 10.88 Acres
    • $11,857 per Acre

    Last Sold Summary

    • 7 Days On Market

    Current Estimated Value $129,946

    Last Listing Agent Chelsea Richardson Barrett and Valley Associates Inc.

    469 Williams Rd, Chester, VT 05143
    • /26

      Est $309,974

      Not Listed For Sale

      203 Marcs Dr, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 871 Sq Ft
      • Built 1988
      203 Marcs Dr, Chester, VT 05143

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

  • /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
  • /20

    $250,000

    Sold Jun 30, 2026

    202 Mountain View, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,140 Sq Ft
    • Built 1945

    Last Sold Summary

    • $219/SF
    • 5 Days On Market

    Current Estimated Value $252,046

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    202 Mountain View, Chester, VT 05143
    • /39

      Est $376,327

      Not Listed For Sale

      401 North St, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,990 Sq Ft
      • Built 1840
      401 North St, Chester, VT 05143

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Jamie Watson BHG Masiello Keene

  • /22

    $249,000

    $50K PRICE DROP
    • Land
    • 84 Acres
    • $2,964 per Acre

    000 Green Mountain Turnpike, Andover, VT 05143

    84+/- Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking 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
  • /16

    $205,000

    Sold Apr 10, 2026

    1876 Popple Dungeon Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1984

    Last Sold Summary

    • $166/SF
    • 6 Days On Market

    Current Estimated Value $213,925

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1876 Popple Dungeon Rd, Chester, VT 05143

Showing Results 41 - 80, Page 2 of 18

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