2,737

Chester, VT Homes

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  • /39

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 3,308 Sq Ft

    76 Goldthwaite Rd, Chester, VT 05143

    Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal-style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

    Gary Coger Four Seasons Sotheby's Int'l Realty

    76 Goldthwaite Rd, Chester, VT 05143
  • /13

    $275,000 Sold Sep 10, 2025

    230 Kevadus Cir, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 894 Sq Ft
    • Built 1970

    Last Sold Summary

    • $308/SF
    • 7 Days On Market

    Current Estimated Value $273,572

    Last Listing Agent Jim Bialowski BHG Masiello Keene

    230 Kevadus Cir, Chester, VT 05143
    • /29

      Est $337,227 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

      • 4% Above List Price
      • $286/SF
      • 18 Days On Market
      • Last Sold Price $325,000
      • Oct 04, 2024

      Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  • /3

    $175,000

    • Land
    • 12.51 Acres
    • $13,989 per Acre

    377 Coach Rd, Chester, VT 05143

    Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home.Located in an area identified for development, it offers both a wonderful building site and long-term

    Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    377 Coach Rd, Chester, VT 05143
  • /2

    $230,000 Sold Nov 07, 2025

    2739 Route 11, Chester, VT 05143

    • 1 Bed
    • 1 Bath
    • 1,424 Sq Ft
    • Built 1987

    Last Sold Summary

    • 23% Below List Price
    • $162/SF
    • 13 Days On Market

    Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

    2739 Route 11, Chester, VT 05143
    • /39

      Est $336,503 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

      • 5% Below List Price
      • $170/SF
      • 19 Days On Market
      • Last Sold Price $355,000
      • Aug 29, 2024

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • /14

    $289,000

    • 2 Beds
    • 2.5 Baths
    • 1,475 Sq Ft

    106 Contro Rd, Chester, VT 05143

    Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided

    Christine Lewis Brattleboro Area Realty

    106 Contro 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
    • /16

      Est $272,961 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% Above List Price
      • $255/SF
      • 6 Days On Market
      • Last Sold Price $257,000
      • Oct 11, 2024

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • /51

    $390,000

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft

    663 Depot St, Chester, VT 05143

    Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that’s hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates.

    Betsy Adamovich Real Broker LLC

    663 Depot 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 $258,193

    Last Listing Agent Lisa Kelley Cummings & Co

    442 Elm St, Chester, VT 05143
    • /37

      Est $257,593 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

      • 1% Above List Price
      • $266/SF
      • 5 Days On Market
      • Last Sold Price $255,000
      • Oct 18, 2024

      Last Listing Agent Frank Provance Diamond Realty

  • /26

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,327 Sq Ft

    160 Depot St, Chester, VT 05143

    Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

    Joshua Lemieux Remax Summit

    160 Depot St, 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 $920,103

    Last Listing Agent Betty McEnaney Diamond Realty

    1502 Popple Dungeon Rd, Chester, VT 05143
    • /40

      Est $256,442 Not Listed For Sale

      165 Vt Route 103 S, Chester, VT 05143

      • 6 Beds
      • 2.5 Baths
      • 2,240 Sq Ft
      • Built 1880
      165 Vt Route 103 S, Chester, VT 05143

      Last Sold Summary

      • 65% Above List Price
      • $69/SF
      • 114 Days On Market
      • Last Sold Price $155,000
      • May 01, 2023

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  • /53

    $359,900 Under Contract

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

    531 Main St, Chester, VT 05143

    Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area

    Katherine Burns William Raveis Real Estate Vermont Properties

    531 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
    • /18

      Est $401,246 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

      • 18% Above List Price
      • $127/SF
      • 22 Days On Market
      • Last Sold Price $340,000
      • Sep 15, 2023

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /55

    $340,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 2,096 Sq Ft

    335 North St, Chester, VT 05143

    Welcome to a charming village retreat in the heart of Chester, perfectly situated on Main Street in the historic Chester Stone Village. This inviting home blends classic Vermont character with comfortable, year-round living. Enter through a practical mudroom with ample space for all your seasonal gear—ideal for embracing Vermont’s four-season lifestyle. To the right, at the front of the home,

    Brendan McNamara William Raveis Real Estate Vermont Properties

    335 North St, 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
    • /30

      Est $354,044 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

      • 1% Above List Price
      • $276/SF
      • 8 Days On Market
      • Last Sold Price $350,000
      • Jun 23, 2023

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • /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
  • /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 $378,030

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    270 North St, Chester, VT 05143
    • /34

      Est $467,835 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

      • 18% Below List Price
      • $307/SF
      • 28 Days On Market
      • Last Sold Price $570,000
      • Aug 21, 2024

      Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  • /9

    $129,000

    • Land
    • 7.95 Acres
    • $16,226 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
  • /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 $196,648

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

    1833 Mattson Rd, Chester, VT 05143
    • /18

      Est $345,489 Not Listed For Sale

      17 Orcutt Dr, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,383 Sq Ft
      • Built 1960
      17 Orcutt Dr, Chester, VT 05143

      Last Sold Summary

      • 20% Above List Price
      • $208/SF
      • 2 Days On Market
      • Last Sold Price $288,000
      • Jun 14, 2023

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

  • /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
  • /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 $336,733

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1470 Flamstead Rd, Chester, VT 05143
    • /28

      Est $257,005 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

      • 7% Above List Price
      • $255/SF
      • 4 Days On Market
      • Last Sold Price $240,000
      • Jun 28, 2024

      Last Listing Agent Julie Buffum Buffum Realty

  • /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
  • /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 $782,319

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    1342 Old Stage Rd, Chester, VT 05143
    • /40

      Est $497,519 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

      • 20% Above List Price
      • $107/SF
      • 7 Days On Market
      • Last Sold Price $416,000
      • Apr 15, 2024

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

  • /18

    $74,500

    • 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
  • /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 $58,744

    Last Listing Agent John Napier TPW Real Estate

    58 Remington Rd, Chester, VT 05143
    • /34

      Est $356,855 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

      • 5% Above List Price
      • $153/SF
      • 10 Days On Market
      • Last Sold Price $340,000
      • Mar 27, 2025

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

  • /38

    $749,000 New Construction

    • 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
  • /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 $208,921

    Last Listing Agent Linda Benoit Highland Realty

    284 Flamstead Rd, Chester, VT 05143
    • /24

      Est $581,028 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

      • 1% Above List Price
      • $219/SF
      • 4 Days On Market
      • Last Sold Price $575,000
      • Sep 15, 2023

      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

    Discover your perfect Vermont getaway on this exceptional 27.8± acre hillside parcel in picturesque Chester, Vermont. Offering sweeping mountain views, privacy, and endless possibilities, this property is ready for your vision. With an approved Vermont state wastewater permit for a 4-bedroom home, you can begin designing your dream family retreat or vacation home right away. A cleared preliminary

    Geralyn Donohue Engel & Völkers Okemo

    00 Quarry Rd, Chester, VT 05143

Showing Results 41 - 80, Page 2 of 18

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