2,722

Chester, VT Homes

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  • /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 $901,511

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

    1847 Trebo Rd, Chester, VT 05143
    • /39

      Est $358,324 Not Listed For Sale

      312 North St, Chester, VT 05143

      • 4 Beds
      • 1 Bath
      • 2,090 Sq Ft
      • Built 1850
      312 North St, Chester, VT 05143

      Last Sold Summary

      • 12% Above List Price
      • $153/SF
      • 150 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Heather Gleim CENTURY 21 North East

  • /30

    $650,000

    • 3 Beds
    • 3 Baths
    • 4,324 Sq Ft

    3630 Vt Route 103 N, Chester, VT 05143

    Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3630 Vt Route 103 N, 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 $543,493

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    1937 Green Mountain Turnpike, Chester, VT 05143
    • /37

      Est $624,886 Not Listed For Sale

      332 Marcs Dr, Chester, VT 05143

      • 4 Beds
      • 3.5 Baths
      • 2,795 Sq Ft
      • Built 1988
      332 Marcs Dr, Chester, VT 05143

      Last Sold Summary

      • 6% Above List Price
      • $211/SF
      • 6 Days On Market

      Last Sold Price $589,000

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /37

    $399,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,148 Sq Ft

    40 Fenton Rd, Chester, VT 05143

    This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of

    John Napier TPW Real Estate

    40 Fenton Rd, Chester, VT 05143
  • /2

    $421,833 Sold Jul 10, 2025

    332 Hidden Heights Rd, Chester, VT 05143

    • 4 Beds
    • 2.5 Baths
    • 2,868 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Below List Price
    • $147/SF
    • 50 Days On Market

    Current Estimated Value $425,093

    Last Listing Agent John Tolosky Barrett and Valley Associates Inc.

    332 Hidden Heights Rd, Chester, VT 05143
    • /10

      Est $317,709 Not Listed For Sale

      784 Vt Route 103 N, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,214 Sq Ft
      • Built 1972
      784 Vt Route 103 N, Chester, VT 05143

      Last Sold Summary

      • 38% Above List Price
      • $190/SF
      • 124 Days On Market

      Last Sold Price $231,000

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

  • /40

    $280,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    818 Davidson Hill Rd, Chester, VT 05143

    Located on the Chester, N. Springfield town line, this cute house sited on just under 3 acres is move in ready. It offers It offers 3 bedrooms two full baths and a designated laundry room. The renovated kitchen featuring stone countertops and nicely styled cabinets. In addition, there is beautiful post and beam back porch that is perfect for morning coffee and late afternoon quiet. With a small

    John Tolosky Barrett and Valley Associates Inc.

    818 Davidson Hill Rd, 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 $163,293

    Last Listing Agent Chelsea Richardson Barrett and Valley Associates Inc.

    469 Williams Rd, Chester, VT 05143
    • /40

      Est $248,811 Not Listed For Sale

      244 Main St, Chester, VT 05143

      • 7 Beds
      • 8 Baths
      • 4,475 Sq Ft
      • Built 1825
      244 Main St, Chester, VT 05143

      Last Sold Summary

      • 57% Below List Price
      • $129/SF
      • 70 Days On Market

      Last Sold Price $579,000

      Last Listing Agent Katie Ladue Gilbert KW Vermont Woodstock

  • /22

    $290,000

    • Land
    • 75 Acres
    • $3,867 per Acre

    1175 Quarry Rd, Chester, VT 05143

    An extraordinary potential homesite set in the hills of southern Vermont. This expansive 75-acre parcel offers the perfect blend of privacy, natural beauty, and endless potential. Whether you dream of building a secluded hilltop retreat or preserving land for recreation and conservation, this property invites endless possibilties. Improvements include a septic system, dug well, electricity and a

    Jessica Samples BHG Masiello Keene

    1175 Quarry Rd, Chester, VT 05143
  • /56

    $402,239 Sold Nov 12, 2025

    4877 Vt Route 103 N, Chester, VT 05143

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1980

    Last Sold Summary

    • 10% Below List Price
    • $233/SF
    • 10 Days On Market

    Current Estimated Value $406,359

    Last Listing Agent Erin Kendall EXP Realty

    4877 Vt Route 103 N, Chester, VT 05143
    • /39

      Est $415,541 Not Listed For Sale

      160 Peck Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 2,068 Sq Ft
      • Built 1925
      160 Peck Rd, Chester, VT 05143

      Last Sold Summary

      • 9% Above List Price
      • $184/SF
      • 5 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

  • /21

    $145,000 Under Contract

    • Land
    • 22.23 Acres
    • $6,523 per Acre

    918 Lovers Lane Rd, Chester, VT 05143

    Located only 2 miles from the picturesque Chester Green you will encounter this newly created 22 acre building parcel on scenic Lover's Lane. This property consists of a 2 acre meadow ideal for building and a 20 acre woodlot consisting of pine, hemlock, oak and maple for sugaring. Beautiful fieldstone walls border most of the boundary lines. The surveyed parcel has an approved 4 bedroom State

    Alan Gombosi Northland Real Estate

    918 Lovers Lane Rd, Chester, VT 05143
  • /47

    $1,375,000 Sold Sep 30, 2025

    465 Pennell Rd, Chester, VT 05143

    • 4 Beds
    • 4.5 Baths
    • 5,700 Sq Ft
    • Built 1967

    Last Sold Summary

    • 8% Below List Price
    • $241/SF
    • 20 Days On Market

    Current Estimated Value $1,330,738

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

    465 Pennell Rd, Chester, VT 05143
    • /34

      Est $918,206 Not Listed For Sale

      835 Quarry Rd, Chester, VT 05143

      • 3 Beds
      • 4 Baths
      • 2,221 Sq Ft
      • Built 1998
      835 Quarry Rd, Chester, VT 05143

      Last Sold Summary

      • 3% Below List Price
      • $425/SF
      • 4 Days On Market

      Last Sold Price $945,000

      Last Listing Agent Alison Cummings Cummings & Co

  • /33

    $299,000

    • 2,702 Sq Ft

    41 Vt Route 103 S, Chester, VT 05143

    Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. Presently, all three units are vacant. Easy to show! There is good

    Glenn Olney Barrett and Valley Associates Inc.

    41 Vt Route 103 S, Chester, VT 05143
  • /2

    $70,000 Sold Oct 21, 2025

    Lot 2 Old Stage Rd, Chester, VT 05143

    • Land
    • 6.3 Acres
    • $11,111 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 35 Days On Market

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    Lot 2 Old Stage Rd, Chester, VT 05143
    • /59

      Est $561,842 Not Listed For Sale

      50 Howard Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 1,728 Sq Ft
      • Built 1986
      50 Howard Rd, Chester, VT 05143

      Last Sold Summary

      • 8% Below List Price
      • $352/SF
      • 27 Days On Market

      Last Sold Price $608,000

      Last Listing Agent Jeremy Collins Ridgeline Real Estate

  • /2

    $165,000 Sold Oct 23, 2025

    1436 Route 103, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft
    • Built 1825

    Last Sold Summary

    • 4% Above List Price
    • $107/SF
    • 2 Days On Market

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1436 Route 103, Chester, VT 05143
    • /33

      Est $655,222 Not Listed For Sale

      50 Goldthwaite Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 2,214 Sq Ft
      • Built 1987
      50 Goldthwaite Rd, Chester, VT 05143

      Last Sold Summary

      • 7% Below List Price
      • $318/SF
      • 27 Days On Market

      Last Sold Price $705,000

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

  • /36

    $425,000 Sold Jul 30, 2025

    115 Orcutt Dr, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,360 Sq Ft
    • Built 1955

    Last Sold Summary

    • $312/SF
    • 26 Days On Market

    Current Estimated Value $428,129

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    115 Orcutt Dr, Chester, VT 05143
    • /39

      Est $817,200 Not Listed For Sale

      76 Goldthwaite Rd, Chester, VT 05143

      • 4 Beds
      • 3 Baths
      • 3,308 Sq Ft
      • Built 1864
      76 Goldthwaite Rd, Chester, VT 05143

      Last Sold Summary

      • 7% Below List Price
      • $266/SF
      • 33 Days On Market

      Last Sold Price $881,000

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

  • /60

    $815,000 Sold Feb 13, 2026

    810 Quarry Rd, Chester, VT 05143

    • 3 Beds
    • 2.5 Baths
    • 2,466 Sq Ft
    • Built 2006

    Last Sold Summary

    • $330/SF
    • 4 Days On Market

    Current Estimated Value $818,480

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    810 Quarry Rd, Chester, VT 05143
    • /19

      Est $206,224 Not Listed For Sale

      83 Potash Brook Rd, Chester, VT 05143

      • 2 Beds
      • 500 Sq Ft
      • Built 1970
      83 Potash Brook Rd, Chester, VT 05143

      Last Sold Summary

      • 6% Above List Price
      • $390/SF
      • 211 Days On Market

      Last Sold Price $195,000

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /2

    $350,000 Sold Nov 09, 2025

    491 Farrar Rd, Chester, VT 05143

    • 4 Beds
    • 3.5 Baths
    • 2,710 Sq Ft
    • Built 1990

    Last Sold Summary

    • 12% Below List Price
    • $129/SF
    • 123 Days On Market

    Current Estimated Value $364,475

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    491 Farrar Rd, Chester, VT 05143
    • /19

      Est $365,482 Not Listed For Sale

      100 Fletcher Hill Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,551 Sq Ft
      • Built 1974
      100 Fletcher Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 12% Above List Price
      • $210/SF
      • 5 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /2

    $229,000 Sold Aug 29, 2025

    87 Kevadus Cir, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 840 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Above List Price
    • $273/SF
    • 2 Days On Market

    Current Estimated Value $238,800

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    87 Kevadus Cir, Chester, VT 05143
    • /26

      Est $342,906 Not Listed For Sale

      154 Fletcher Hill Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,300 Sq Ft
      • Built 1979
      154 Fletcher Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 22% Above List Price
      • $215/SF
      • 52 Days On Market

      Last Sold Price $280,000

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

  • /52

    $1,850,000 Sold Apr 30, 2025

    1328 Chandler Rd, Chester, VT 05143

    • 4 Beds
    • 3.5 Baths
    • 3,779 Sq Ft
    • Built 1972

    Last Sold Summary

    • 21% Below List Price
    • $490/SF
    • 220 Days On Market

    Current Estimated Value $1,622,939

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

    1328 Chandler Rd, Chester, VT 05143
    • /24

      Est $273,583 Not Listed For Sale

      1369 Flamstead Rd, Chester, VT 05143

      • 3 Beds
      • 1.5 Baths
      • 1,096 Sq Ft
      • Built 1973
      1369 Flamstead Rd, Chester, VT 05143

      Last Sold Summary

      • 19% Above List Price
      • $210/SF
      • 8 Days On Market

      Last Sold Price $230,000

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • /21

    $320,000 Sold Dec 18, 2025

    870 Cummings Rd, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,525 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $210/SF
    • 30 Days On Market

    Current Estimated Value $320,135

    Last Listing Agent Julie Buffum Buffum Realty

    870 Cummings Rd, Chester, VT 05143
    • /40

      Est $619,465 Not Listed For Sale

      1573 Trebo Rd, Chester, VT 05143

      • 2 Beds
      • 2.5 Baths
      • 1,444 Sq Ft
      • Built 1988
      1573 Trebo Rd, Chester, VT 05143

      Last Sold Summary

      • 5% Below List Price
      • $450/SF
      • 5 Days On Market

      Last Sold Price $650,000

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  • /41

    $327,500 Sold Aug 21, 2025

    769 Davidson Hill Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2002

    Last Sold Summary

    • 2% Below List Price
    • $234/SF
    • 7 Days On Market

    Current Estimated Value $336,676

    Last Listing Agent Frank Provance Diamond Realty

    769 Davidson Hill Rd, Chester, VT 05143
    • /13

      Not Listed For Sale

      28 Mineral Spring Rd, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 852 Sq Ft
      • Built 1993
      28 Mineral Spring Rd, Chester, VT 05143

      Last Sold Summary

      • $153/SF
      • 27 Days On Market

      Last Sold Price $130,500

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /37

    $389,000 Sold Sep 22, 2025

    62 Circle Dr, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • Built 1945

    Last Sold Summary

    • $325/SF
    • 6 Days On Market

    Current Estimated Value $414,851

    Last Listing Agent Chelsea Bevis KW Vermont Woodstock

    62 Circle Dr, Chester, VT 05143
    • /38

      Est $321,246 Not Listed For Sale

      616 Mattson Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,349 Sq Ft
      • Built 1940
      616 Mattson Rd, Chester, VT 05143

      Last Sold Summary

      • 1% Below List Price
      • $241/SF
      • 119 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Jessica Citera Cummings & Co

  • /26

    $311,688 Sold May 30, 2025

    3590 Vt 103, Chester, VT 05143

    • 4 Beds
    • 2 Baths
    • 2,702 Sq Ft
    • Built 1850

    Last Sold Summary

    • 35% Below List Price
    • $115/SF
    • 387 Days On Market

    Last Listing Agent Jessica Samples BHG Masiello Keene

    3590 Vt 103, Chester, VT 05143
    • /36

      Est $451,664 Not Listed For Sale

      231 Snell Rd, Chester, VT 05143

      • 3 Beds
      • 3 Baths
      • 2,465 Sq Ft
      • Built 1986
      231 Snell Rd, Chester, VT 05143

      Last Sold Summary

      • 6% Above List Price
      • $174/SF
      • 18 Days On Market

      Last Sold Price $428,000

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

Showing Results 81 - 120, Page 3 of 18

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