2,718

Chester, VT Homes

Section Image
  • 1767 Rockingham Rd, Chester, VT 05143
    1767 Rockingham Rd, Chester, VT 05143
    1767 Rockingham Rd, Chester, VT 05143
    /24

    $310,000 Sold Dec 03, 2024

    • 1,293 Sq Ft
    • $240/SF
    • 116 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1988

    1767 Rockingham Rd, Chester, VT 05143

    This beautiful turnkey Log home is the perfect weekend getaway or a convenient and tasteful primary residence. Located less than 30 minutes from both Okemo and Magic Mountain, it offers plenty of opportunities for mountain adventures. Whether you're into skiing, hiking, or simply enjoying the stunning landscapes, you'll find it all within easy reach. The home has recently received numerous

    Thaddeus Abare Barrett and Valley Associates Inc.

    1767 Rockingham Rd, Chester, VT 05143
    • 739 Gould Rd, Chester, VT 05143
      739 Gould Rd, Chester, VT 05143
      739 Gould Rd, Chester, VT 05143
      /32

      Est $281,997 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,664 Sq Ft

      739 Gould Rd, Chester, VT 05143

      739 Gould Rd, Chester, VT 05143
  • 0 Remington Rd Unit 12 5001944, Chester, VT 05143
    0 Remington Rd Unit 12 5001944, Chester, VT 05143
    0 Remington Rd Unit 12 5001944, Chester, VT 05143
    /12

    $19,000 Sold Nov 29, 2024

    • Land
    • 5.51 Acres
    • $3,448 per Acre
    • 183 Days On Market

    0 Remington Rd Unit 12 5001944, Chester, VT 05143

    REUCDUED $18,000.00, PRICED TO SELL! One of the larger lots in the lower Remington subdivision. This private lot has underground power at the lot and the permitted septic is an inground system. Bring your plans and your builder or have the seller build your dream home! PLEASE NOTE THERE IS A MINIMUM OF 1,800 Sq Ft Of Finished Living Space.

    Frank Provance Diamond Realty

    0 Remington Rd Unit 12 5001944, Chester, VT 05143
    • 5051 Vt Route 103 N, Chester, VT 05143
      5051 Vt Route 103 N, Chester, VT 05143
      5051 Vt Route 103 N, Chester, VT 05143
      /8

      Est $221,362 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft

      5051 Vt Route 103 N, Chester, VT 05143

      5051 Vt Route 103 N, Chester, VT 05143
  • 56 Hidden Newton Rd, Chester, VT 05143
    56 Hidden Newton Rd, Chester, VT 05143
    56 Hidden Newton Rd, Chester, VT 05143
    /41

    $410,000 Sold Nov 08, 2024

    • 1,410 Sq Ft
    • $291/SF
    • 44 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1999

    56 Hidden Newton Rd, Chester, VT 05143

    This log home in Windham includes a large yard with fruit trees, room for gardening and recreation, privately situated on a quiet dead-end street. Enjoy the peace and quiet of the natural surroundings with a small pond, apple trees and large deck to relax on. This 3 bedroom , 2 bath home has a nice interior flow with an open kitchen/living/dining floor plan. Enter through the large mudroom and

    Alison Cummings Cummings & Co

    56 Hidden Newton Rd, Chester, VT 05143
    • 247 Cavendish Rd, Chester, VT 05143
      247 Cavendish Rd, Chester, VT 05143
      247 Cavendish Rd, Chester, VT 05143
      /20

      Est $308,254 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft

      247 Cavendish Rd, Chester, VT 05143

      247 Cavendish Rd, Chester, VT 05143
  • 2656 Weston-Andover Rd, Chester, VT 05143
    2656 Weston-Andover Rd, Chester, VT 05143
    2656 Weston-Andover Rd, Chester, VT 05143
    /40

    $595,000 Sold Nov 08, 2024

    • 2,080 Sq Ft
    • $286/SF
    • 55 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 2004

    2656 Weston-Andover Rd, Chester, VT 05143

    One of a kind! If you wanted to be 100% off the grid, but in a home that looks & functions like a traditional home, then look no further. This is a special home-from the quiet spot on the Ox Bow with long brook frontage to the handsome architecture & interior detail. No other house will ever be visible, your privacy is protected, but you are minutes from Weston, Chester & Ludlow. The floorplan is

    Betty McEnaney Diamond Realty

    2656 Weston-Andover Rd, Chester, VT 05143
    • 538 Clemons Rd, Chester, VT 05143
      538 Clemons Rd, Chester, VT 05143
      538 Clemons Rd, Chester, VT 05143
      /23

      Est $466,694 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,115 Sq Ft

      538 Clemons Rd, Chester, VT 05143

      538 Clemons Rd, Chester, VT 05143
  • 3264 Trebo Rd, Chester, VT 05143
    3264 Trebo Rd, Chester, VT 05143
    3264 Trebo Rd, Chester, VT 05143
    /18

    $295,000 Sold Nov 01, 2024

    • 1,487 Sq Ft
    • $198/SF
    • 41 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1910

    3264 Trebo Rd, Chester, VT 05143

    Discover the potential of this 1910 farmhouse, nestled on 15 picturesque acres at the corner of Trebo Rd and Crow Hill Rd. 5 of the acres are across the road featuring a large pond big enough for swimming and kayaking, this property offers a canvas for your vision. The Farmhouse is in need of extensive rehab but whether renovating the existing structure or building anew this property is ideal for

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3264 Trebo Rd, Chester, VT 05143
    • 3483 Popple Dungeon Rd, Chester, VT 05143
      3483 Popple Dungeon Rd, Chester, VT 05143
      3483 Popple Dungeon Rd, Chester, VT 05143
      /29

      Est $276,878 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 910 Sq Ft

      3483 Popple Dungeon Rd, Chester, VT 05143

      3483 Popple Dungeon Rd, Chester, VT 05143
  • 276 Old Coach Rd, Chester, VT 05143
    276 Old Coach Rd, Chester, VT 05143
    276 Old Coach Rd, Chester, VT 05143
    /39

    $715,000 Sold Oct 26, 2024

    • 1,735 Sq Ft
    • $412/SF
    • 108 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2021

    276 Old Coach Rd, Chester, VT 05143

    This magnificent newly constructed home has it all! Located in the peaceful Popple Dungeon area of Chester, Vermont, you'll feel a million miles away from the world, nestled within 29 beautifully wooded acres along the South Branch of the Williams River. With just a short walk, you have over 1/4 mile of your very own stream to cool off in. There is no urban glow, little to no traffic, and the

    Daire Gibney Barrett and Valley Associates Inc.

    276 Old Coach Rd, Chester, VT 05143
    • 3019 Popple Dungeon Rd, Chester, VT 05143
      3019 Popple Dungeon Rd, Chester, VT 05143
      3019 Popple Dungeon Rd, Chester, VT 05143
      /20

      Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 200 Sq Ft

      3019 Popple Dungeon Rd, Chester, VT 05143

      3019 Popple Dungeon Rd, Chester, VT 05143
  • 22 White Rd, Chester, VT 05143
    22 White Rd, Chester, VT 05143
    22 White Rd, Chester, VT 05143
    /12

    $124,000 Sold Oct 25, 2024

    • 630 Sq Ft
    • $197/SF
    • 6 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1940

    22 White Rd, Chester, VT 05143

    Priced below town assessment and just in time for hunting season, this cute cottage/camp is being sold "as is." This camp sits on 1.1 acres of land, septic tank installed 10 to 15 years ago. It features living room, kitchen, bedroom and a 3/4 bath on the main floor and a loft in part of the second floor. It also has a shed and an outhouse. Don't miss this opportunity!!!

    Darlene Conca Keller Williams Realty Metro-Keene

    22 White Rd, Chester, VT 05143
    • 138 Farrar Rd, Chester, VT 05143
      138 Farrar Rd, Chester, VT 05143
      138 Farrar Rd, Chester, VT 05143
      /23

      Est $360,060 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,464 Sq Ft

      138 Farrar Rd, Chester, VT 05143

      138 Farrar Rd, Chester, VT 05143
  • 468 Vt Route 103 S, Chester, VT 05143
    468 Vt Route 103 S, Chester, VT 05143
    468 Vt Route 103 S, Chester, VT 05143
    /37

    $255,000 Sold Oct 18, 2024

    • 960 Sq Ft
    • $266/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1940

    468 Vt Route 103 S, Chester, VT 05143

    Come check out this Main St., turn-key charmer, on a level corner lot, in the Village of Chester. A great neighborhood, walking distance to local shops, schools and in town amenities. You'll love the convenience of the attached (via breezeway) one car garage. This home boasts new paint in every room, updated floors, kitchen and bath, with new furnishings and mattresses. The lighting in the

    Frank Provance Diamond Realty

    468 Vt Route 103 S, Chester, VT 05143
    • 788 Farrar Rd, Chester, VT 05143
      788 Farrar Rd, Chester, VT 05143
      788 Farrar Rd, Chester, VT 05143
      /35

      Est $457,406 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 1,872 Sq Ft

      788 Farrar Rd, Chester, VT 05143

      788 Farrar Rd, Chester, VT 05143
  • 2253 White Rd, Chester, VT 05143
    2253 White Rd, Chester, VT 05143
    2253 White Rd, Chester, VT 05143
    /38

    $680,000 Sold Oct 17, 2024

    • 1,171 Sq Ft
    • $581/SF
    • 53 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1990

    2253 White Rd, Chester, VT 05143

    Stunning acreage surrounds this charming home in Windham, Vermont.110 acres of curated land with trails throughout. Lots of places to explore and enjoy, all on your own land! A quintessential get-away with a large screened-in porch overlooking the waterfall and pond. Follow the bridge across the pond to the meadow and trails. The extensive trail network is well maintained, meandering throughout

    Alison Cummings Cummings & Co

    2253 White Rd, Chester, VT 05143
    • 2370 Baltimore Rd, Chester, VT 05143
      2370 Baltimore Rd, Chester, VT 05143
      2370 Baltimore Rd, Chester, VT 05143
      /23

      Est $170,269 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,124 Sq Ft

      2370 Baltimore Rd, Chester, VT 05143

      2370 Baltimore Rd, Chester, VT 05143
  • 1295 Middletown Rd, Chester, VT 05143
    1295 Middletown Rd, Chester, VT 05143
    /2

    $792,000 Sold Jul 15, 2025

    • 3,614 Sq Ft
    • $219/SF
    • 0 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2012

    1295 Middletown Rd, Chester, VT 05143

    Discover this beautifully maintained 3-bedroom, 31⁄2-bath home on over 3 acres along a quiet country road—just minutes from the village of Weston. Inside, an open-concept layout brings together a bright kitchen, dining, and living area, while the walk-out lower level adds flexible room for a family area or recreation. Spacious entry/mudroom and an attached 2-car garage, this home balances

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    1295 Middletown Rd, Chester, VT 05143
    • 1248 Baltimore Rd, Chester, VT 05143
      1248 Baltimore Rd, Chester, VT 05143
      1248 Baltimore Rd, Chester, VT 05143
      /18

      Est $179,818 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 600 Sq Ft

      1248 Baltimore Rd, Chester, VT 05143

      1248 Baltimore Rd, Chester, VT 05143
  • 17 Grafton St, Chester, VT 05143
    17 Grafton St, Chester, VT 05143
    /2

    $285,000 Sold Mar 26, 2025

    • 1,824 Sq Ft
    • $156/SF
    • 87 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1852

    17 Grafton St, Chester, VT 05143

    Discover this beautifully maintained 1852 Colonial home situated on a prime corner lot in the heart of downtown Chester. Currently configured as a two-unit apartment, this property features a spacious two-bedroom, one-bath unit on the upper level and a cozy one-bedroom, one-bath unit on the first floor. With its versatile layout, you can easily convert it back to a single-family residence or live

    Gary Coger Four Seasons Sotheby's Int'l Realty

    17 Grafton St, Chester, VT 05143
    • 870 Baltimore Rd, Chester, VT 05143
      870 Baltimore Rd, Chester, VT 05143
      870 Baltimore Rd, Chester, VT 05143
      /40

      Est $416,515 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,100 Sq Ft

      870 Baltimore Rd, Chester, VT 05143

      870 Baltimore Rd, Chester, VT 05143
    • 42 Cobb Rd, Chester, VT 05143
      42 Cobb Rd, Chester, VT 05143
      42 Cobb Rd, Chester, VT 05143
      /40

      Est $346,251 Not Listed For Sale

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

      42 Cobb Rd, Chester, VT 05143

      42 Cobb Rd, Chester, VT 05143
    • 135 Lower Bartonsville Rd, Chester, VT 05143
      135 Lower Bartonsville Rd, Chester, VT 05143
      135 Lower Bartonsville Rd, Chester, VT 05143
      /14

      Est $307,103 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,904 Sq Ft

      135 Lower Bartonsville Rd, Chester, VT 05143

      135 Lower Bartonsville Rd, Chester, VT 05143
    • 234 Athens Rd, Chester, VT 05143
      234 Athens Rd, Chester, VT 05143
      234 Athens Rd, Chester, VT 05143
      /37

      Est $204,000 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,800 Sq Ft

      234 Athens Rd, Chester, VT 05143

      234 Athens Rd, Chester, VT 05143
    • 116 Reed Rd, Chester, VT 05143
      116 Reed Rd, Chester, VT 05143
      116 Reed Rd, Chester, VT 05143
      /21

      Est $351,836 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft

      116 Reed Rd, Chester, VT 05143

      116 Reed Rd, Chester, VT 05143
    • 1096 Mattson Rd, Chester, VT 05143
      1096 Mattson Rd, Chester, VT 05143
      1096 Mattson Rd, Chester, VT 05143
      /26

      Est $268,328 Not Listed For Sale

      1096 Mattson Rd, Chester, VT 05143

      1096 Mattson Rd, Chester, VT 05143
    • 656 Depot St, Chester, VT 05143
      656 Depot St, Chester, VT 05143
      656 Depot St, Chester, VT 05143
      /35

      Est $276,143 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,280 Sq Ft

      656 Depot St, Chester, VT 05143

      656 Depot St, Chester, VT 05143
    • 234 Lower Bartonsville Rd, Chester, VT 05143
      234 Lower Bartonsville Rd, Chester, VT 05143
      234 Lower Bartonsville Rd, Chester, VT 05143
      /17

      Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 1,116 Sq Ft

      234 Lower Bartonsville Rd, Chester, VT 05143

      234 Lower Bartonsville Rd, Chester, VT 05143
    • 2358 N Hill Rd, Chester, VT 05143
      2358 N Hill Rd, Chester, VT 05143
      2358 N Hill Rd, Chester, VT 05143
      /39

      Est $494,820 Not Listed For Sale

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

      2358 N Hill Rd, Chester, VT 05143

      2358 N Hill Rd, Chester, VT 05143
    • 2401 N Hill Rd, Chester, VT 05143
      2401 N Hill Rd, Chester, VT 05143
      2401 N Hill Rd, Chester, VT 05143
      /38

      Est $735,619 Not Listed For Sale

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

      2401 N Hill Rd, Chester, VT 05143

      2401 N Hill Rd, Chester, VT 05143
    • 126 Gould Rd, Chester, VT 05143
      126 Gould Rd, Chester, VT 05143
      126 Gould Rd, Chester, VT 05143
      /25

      Est $298,000 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,714 Sq Ft

      126 Gould Rd, Chester, VT 05143

      126 Gould Rd, Chester, VT 05143
    • 723 Chandler Rd, Chester, VT 05143
      723 Chandler Rd, Chester, VT 05143
      723 Chandler Rd, Chester, VT 05143
      /36

      Est $522,886 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,063 Sq Ft

      723 Chandler Rd, Chester, VT 05143

      723 Chandler Rd, Chester, VT 05143
    • 3208 Green Mountain Turnpike, Chester, VT 05143
      3208 Green Mountain Turnpike, Chester, VT 05143
      3208 Green Mountain Turnpike, Chester, VT 05143
      /27

      Est $358,885 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft

      3208 Green Mountain Turnpike, Chester, VT 05143

      3208 Green Mountain Turnpike, Chester, VT 05143
    • 1716 Brockway Mills Rd, Chester, VT 05143
      1716 Brockway Mills Rd, Chester, VT 05143
      1716 Brockway Mills Rd, Chester, VT 05143
      /40

      Est $561,546 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,908 Sq Ft

      1716 Brockway Mills Rd, Chester, VT 05143

      1716 Brockway Mills Rd, Chester, VT 05143
    • 505 Hidden Heights Rd, Chester, VT 05143
      505 Hidden Heights Rd, Chester, VT 05143
      505 Hidden Heights Rd, Chester, VT 05143
      /26

      Est $105,362 Not Listed For Sale

      505 Hidden Heights Rd, Chester, VT 05143

      505 Hidden Heights Rd, Chester, VT 05143
    • 0 Route 103 Unit 4999744, Chester, VT 05143
      0 Route 103 Unit 4999744, Chester, VT 05143
      0 Route 103 Unit 4999744, Chester, VT 05143
      /14

      Not Listed For Sale

      0 Route 103 Unit 4999744, Chester, VT 05143

      0 Route 103 Unit 4999744, Chester, VT 05143
    • 1291 Potash Brook Rd, Chester, VT 05143
      1291 Potash Brook Rd, Chester, VT 05143
      1291 Potash Brook Rd, Chester, VT 05143
      /35

      Est $153,609 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 704 Sq Ft

      1291 Potash Brook Rd, Chester, VT 05143

      1291 Potash Brook Rd, Chester, VT 05143
    • 3610 Vt Route 103 N Unit 50003, Chester, VT 03602
      3610 Vt Route 103 N Unit 50003, Chester, VT 03602
      3610 Vt Route 103 N Unit 50003, Chester, VT 03602
      /8

      Not Listed For Sale

      3610 Vt Route 103 N Unit 50003, Chester, VT 03602

      3610 Vt Route 103 N Unit 50003, Chester, VT 03602
    • 222 Peck Rd, Chester, VT 05143
      222 Peck Rd, Chester, VT 05143
      222 Peck Rd, Chester, VT 05143
      /20

      Est $215,297 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 864 Sq Ft

      222 Peck Rd, Chester, VT 05143

      222 Peck Rd, Chester, VT 05143

Showing Results 161 - 200, Page 5 of 18

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