2,743

Chester, VT Homes

Section Image
  • 758 Weston-Andover Rd, Chester, VT 05143
    758 Weston-Andover Rd, Chester, VT 05143
    758 Weston-Andover Rd, Chester, VT 05143
    /60

    $625,000

    • 4 Beds
    • 3.5 Baths
    • 2,656 Sq Ft

    758 Weston-Andover Rd, Chester, VT 05143

    A rare opportunity to own two well-maintained homes on one beautiful country property! The main residence offers 3 bedrooms and 3 baths with a warm, inviting interior featuring hardwood floors, abundant built-ins, and thoughtfully designed living spaces that blend character with everyday comfort. Step outside to the back deck overlooking beautifully landscaped gardens and a spacious lawn—an ideal

    Kevin Barnes William Raveis Real Estate Vermont Properties

    758 Weston-Andover Rd, Chester, VT 05143
  • Lot 1 Old Stage Rd, Chester, VT 05143
    Lot 1 Old Stage Rd, Chester, VT 05143
    /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
    • 183 Pleasant St, Chester, VT 05143
      183 Pleasant St, Chester, VT 05143
      183 Pleasant St, Chester, VT 05143
      /18

      Est $442,528

      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

  • 955 Smokeshire Rd, Chester, VT 05143
    955 Smokeshire Rd, Chester, VT 05143
    955 Smokeshire Rd, Chester, VT 05143
    /60

    $750,000

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

    955 Smokeshire Rd, Chester, VT 05143

    Tucked away on a quiet country road in one of Chester’s most coveted areas, this striking contemporary home offers the ultimate Vermont lifestyle—just miles from the Okemo Mountain base lodge. Embraced by nature and thoughtful landscape, the property seamlessly connects refined indoor living with the natural beauty of its private riverfront, complete with your own summer swimming hole. Inside,

    Katherine Burns William Raveis Real Estate Vermont Properties

    955 Smokeshire Rd, Chester, VT 05143
  • 442 Elm St, Chester, VT 05143
    442 Elm St, Chester, VT 05143
    /2

    $259,000

    Sold Jul 31, 2025

    442 Elm St, Chester, VT 05143

    • 1,488 Sq Ft
    • Built 1950

    Last Sold Summary

    • $174/SF
    • 43 Days On Market

    Current Estimated Value $254,915

    Last Listing Agent Lisa Kelley Cummings & Co

    442 Elm St, Chester, VT 05143
    • 64 Highland Ct, Chester, VT 05143
      64 Highland Ct, Chester, VT 05143
      64 Highland Ct, Chester, VT 05143
      /30

      Est $350,979

      Not Listed For Sale

      64 Highland Ct, Chester, VT 05143

      • 3 Beds
      • 1.5 Baths
      • 1,267 Sq Ft
      • Built 1952
      64 Highland Ct, Chester, VT 05143

      Last Sold Summary

      • 8 Days On Market

  • 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 Lange Lange & Lange

    00 Vermont 103, Andover, VT 05143
  • 1502 Popple Dungeon Rd, Chester, VT 05143
    1502 Popple Dungeon Rd, Chester, VT 05143
    1502 Popple Dungeon Rd, Chester, VT 05143
    /59

    $910,000

    Sold Aug 28, 2025

    1502 Popple Dungeon Rd, Chester, VT 05143

    • 3 Beds
    • 4 Baths
    • 3,739 Sq Ft
    • Built 1989

    Last Sold Summary

    • 24% Below List Price
    • $243/SF
    • 105 Days On Market

    Current Estimated Value $924,538

    Last Listing Agent Betty McEnaney Diamond Realty

    1502 Popple Dungeon Rd, Chester, VT 05143
    • 405 Church St, Chester, VT 05143
      405 Church St, Chester, VT 05143
      405 Church St, Chester, VT 05143
      /34

      Est $479,259

      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

  • 0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
    /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
  • 515 Main St, Chester, VT 05143
    515 Main St, Chester, VT 05143
    515 Main St, 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
    • 102 Church St, Chester, VT 05143
      102 Church St, Chester, VT 05143
      102 Church St, Chester, VT 05143
      /48

      Est $412,076

      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

  • 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
  • 4150 Trebo Rd, Chester, VT 05143
    4150 Trebo Rd, Chester, VT 05143
    4150 Trebo Rd, Chester, VT 05143
    /42

    $315,000

    Sold Aug 06, 2025

    4150 Trebo Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • Built 1995

    Last Sold Summary

    • $201/SF
    • 5 Days On Market

    Last Listing Agent Alexandra Eatmon Kelley Real Estate, Inc.

    4150 Trebo Rd, Chester, VT 05143
    • 386 1st Ave, Chester, VT 05143
      386 1st Ave, Chester, VT 05143
      386 1st Ave, Chester, VT 05143
      /28

      Est $249,976

      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

  • 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. Whether

    Rachael Lange Lange & Lange

    00 Vt Route 103 N, Chester, VT 05143
  • 531 Main St, Chester, VT 05143
    531 Main St, Chester, VT 05143
    531 Main St, 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 $352,893

    Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

    531 Main St, Chester, VT 05143
    • 595 Main St, Chester, VT 05143
      595 Main St, Chester, VT 05143
      595 Main St, Chester, VT 05143
      /40

      Est $496,523

      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

  • 547 Williams Rd, Chester, VT 05143
    547 Williams Rd, Chester, VT 05143
    547 Williams Rd, Chester, VT 05143
    /60

    $474,900

    $24K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    547 Williams Rd, Chester, VT 05143

    MOTIVATED SELLERS welcome you to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, direct access to VAST, located less than an hour from six renowned ski resorts and amenities. So many updates in the past two years; fully remodeled kitchen and bathrooms, fresh paint, new flooring along with numerous updates (list attached in associate documents); modern and

    Terri Edgerley Edge Realty Vermont

    547 Williams Rd, Chester, VT 05143
  • 270 North St, Chester, VT 05143
    270 North St, Chester, VT 05143
    270 North St, Chester, VT 05143
    /58

    $373,000

    Sold Jul 10, 2025

    270 North St, Chester, VT 05143

    • 4 Beds
    • 1.5 Baths
    • 2,919 Sq Ft
    • Built 1810

    Last Sold Summary

    • 7% Below List Price
    • $128/SF
    • 61 Days On Market

    Current Estimated Value $401,420

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    270 North St, Chester, VT 05143
    • 489 Main St, Chester, VT 05143
      489 Main St, Chester, VT 05143
      489 Main St, Chester, VT 05143
      /34

      Est $409,948

      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

  • TBD Farrar Rd, Chester, VT 05143
    TBD Farrar Rd, Chester, VT 05143
    TBD Farrar Rd, Chester, VT 05143
    /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
  • 1833 Mattson Rd, Chester, VT 05143
    1833 Mattson Rd, Chester, VT 05143
    1833 Mattson 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 $207,859

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

    1833 Mattson Rd, Chester, VT 05143
    • 548 Main St, Chester, VT 05143
      548 Main St, Chester, VT 05143
      548 Main St, Chester, VT 05143
      /24

      Est $566,588

      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

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

    $695,000

    New Construction $94K PRICE DROP
    • 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
  • 1470 Flamstead Rd, Chester, VT 05143
    1470 Flamstead Rd, Chester, VT 05143
    1470 Flamstead 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 $354,036

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1470 Flamstead Rd, Chester, VT 05143
    • 203 Marcs Dr, Chester, VT 05143
      203 Marcs Dr, Chester, VT 05143
      203 Marcs Dr, Chester, VT 05143
      /26

      Est $311,904

      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

  • 3668 Vt Route 103 N, Chester, VT 05143
    3668 Vt Route 103 N, Chester, VT 05143
    3668 Vt Route 103 N, Chester, VT 05143
    /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
  • 1342 Old Stage Rd, Chester, VT 05143
    1342 Old Stage Rd, Chester, VT 05143
    1342 Old Stage Rd, 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 $803,047

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    1342 Old Stage Rd, Chester, VT 05143
    • 683 Church St, Chester, VT 05143
      683 Church St, Chester, VT 05143
      683 Church St, Chester, VT 05143
      /40

      Est $1,280,938

      Not Listed For Sale

      683 Church St, Chester, VT 05143

      • 7 Beds
      • 6 Baths
      • 5,566 Sq Ft
      • Built 1801
      683 Church St, Chester, VT 05143

      Last Sold Summary

      • 236 Days On Market

  • 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
  • 58 Remington Rd, Chester, VT 05143
    58 Remington Rd, Chester, VT 05143
    58 Remington 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 $57,998

    Last Listing Agent John Napier TPW Real Estate

    58 Remington Rd, Chester, VT 05143
    • 401 North St, Chester, VT 05143
      401 North St, Chester, VT 05143
      401 North St, Chester, VT 05143
      /39

      Est $382,699

      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

  • 201 Spruce Dr, Chester, VT 05143
    201 Spruce Dr, Chester, VT 05143
    201 Spruce Dr, Chester, VT 05143
    /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
  • 284 Flamstead Rd, Chester, VT 05143
    284 Flamstead Rd, Chester, VT 05143
    284 Flamstead 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 $221,989

    Last Listing Agent Linda Benoit Highland Realty

    284 Flamstead Rd, Chester, VT 05143
    • 196 North St, Chester, VT 05143
      196 North St, Chester, VT 05143
      196 North St, Chester, VT 05143
      /60

      Est $400,417

      Not Listed For Sale

      196 North St, Chester, VT 05143

      • 3 Beds
      • 3 Baths
      • 2,960 Sq Ft
      • Built 1844
      196 North St, Chester, VT 05143

      Last Sold Summary

      • 166 Days On Market

  • 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
  • 1847 Trebo Rd, Chester, VT 05143
    1847 Trebo Rd, Chester, VT 05143
    1847 Trebo Rd, 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 $817,175

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

    1847 Trebo Rd, Chester, VT 05143
    • 250 North St, Chester, VT 05143
      250 North St, Chester, VT 05143
      250 North St, Chester, VT 05143
      /28

      Est $358,924

      Not Listed For Sale

      250 North St, Chester, VT 05143

      • 5 Beds
      • 2 Baths
      • 2,152 Sq Ft
      • Built 1844
      250 North St, Chester, VT 05143

      Last Sold Summary

      • 8 Days On Market

  • 000 Green Mountain Turnpike, Andover, VT 05143
    000 Green Mountain Turnpike, Andover, VT 05143
    000 Green Mountain Turnpike, Andover, VT 05143
    /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

Showing Results 41 - 80, Page 2 of 18

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