2,725

Windsor, VT Homes

Section Image
    • 199 Maple Ridge Rd, Chester, VT 05143
      199 Maple Ridge Rd, Chester, VT 05143
      199 Maple Ridge Rd, Chester, VT 05143
      /31

      Est $384,763 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,492 Sq Ft

      199 Maple Ridge Rd, Chester, VT 05143

      199 Maple Ridge Rd, Chester, VT 05143
  • 1295 Middletown Rd, Chester, VT 05143
    1295 Middletown Rd, Chester, VT 05143
    /2

    $792,000 Sold Jul 15, 2025

    • 2,133 Sq Ft
    • $371/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
    • 739 Gould Rd, Chester, VT 05143
      739 Gould Rd, Chester, VT 05143
      739 Gould Rd, Chester, VT 05143
      /32

      Est $306,414 Not Listed For Sale

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

      739 Gould Rd, Chester, VT 05143

      739 Gould 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
    • 1698 Dean Brook Rd, Chester, VT 05143
      1698 Dean Brook Rd, Chester, VT 05143
      1698 Dean Brook Rd, Chester, VT 05143
      /32

      Est $469,056 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,602 Sq Ft

      1698 Dean Brook Rd, Chester, VT 05143

      1698 Dean Brook Rd, 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 $226,476 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
    • 247 Cavendish Rd, Chester, VT 05143
      247 Cavendish Rd, Chester, VT 05143
      247 Cavendish Rd, Chester, VT 05143
      /20

      Est $362,110 Not Listed For Sale

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

      247 Cavendish Rd, Chester, VT 05143

      247 Cavendish Rd, Chester, VT 05143
    • 538 Clemons Rd, Chester, VT 05143
      538 Clemons Rd, Chester, VT 05143
      538 Clemons Rd, Chester, VT 05143
      /23

      Est $499,215 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,900 Sq Ft

      538 Clemons Rd, Chester, VT 05143

      538 Clemons Rd, Chester, VT 05143
    • 529 Nudist Camp Rd, Chester, VT 05143
      529 Nudist Camp Rd, Chester, VT 05143
      529 Nudist Camp Rd, Chester, VT 05143
      /26

      Est $585,229 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,665 Sq Ft

      529 Nudist Camp Rd, Chester, VT 05143

      529 Nudist Camp 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
    • 374 Richardson Rd, Chester, VT 05143
      374 Richardson Rd, Chester, VT 05143
      374 Richardson Rd, Chester, VT 05143
      /40

      Est $713,887 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,776 Sq Ft

      374 Richardson Rd, Chester, VT 05143

      374 Richardson Rd, Chester, VT 05143
    • 138 Farrar Rd, Chester, VT 05143
      138 Farrar Rd, Chester, VT 05143
      138 Farrar Rd, Chester, VT 05143
      /23

      Est $421,079 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,944 Sq Ft

      138 Farrar Rd, Chester, VT 05143

      138 Farrar Rd, Chester, VT 05143
    • 788 Farrar Rd, Chester, VT 05143
      788 Farrar Rd, Chester, VT 05143
      788 Farrar Rd, Chester, VT 05143
      /35

      Est $441,348 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
    • 2370 Baltimore Rd, Chester, VT 05143
      2370 Baltimore Rd, Chester, VT 05143
      2370 Baltimore Rd, Chester, VT 05143
      /23

      Est $189,766 Not Listed For Sale

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

      2370 Baltimore Rd, Chester, VT 05143

      2370 Baltimore Rd, Chester, VT 05143
    • 1248 Baltimore Rd, Chester, VT 05143
      1248 Baltimore Rd, Chester, VT 05143
      1248 Baltimore Rd, Chester, VT 05143
      /18

      Est $193,063 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 600 Sq Ft

      1248 Baltimore Rd, Chester, VT 05143

      1248 Baltimore Rd, Chester, VT 05143
    • 870 Baltimore Rd, Chester, VT 05143
      870 Baltimore Rd, Chester, VT 05143
      870 Baltimore Rd, Chester, VT 05143
      /40

      Est $515,440 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,767 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 $365,824 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
    • 46 Anderson Rd, Chester, VT 05143
      46 Anderson Rd, Chester, VT 05143
      46 Anderson Rd, Chester, VT 05143
      /19

      Est $200,302 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,273 Sq Ft

      46 Anderson Rd, Chester, VT 05143

      46 Anderson 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 $332,889 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
    • 115 Reed Rd, Chester, VT 05143
      115 Reed Rd, Chester, VT 05143
      115 Reed Rd, Chester, VT 05143
      /11

      Est $286,604 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,408 Sq Ft

      115 Reed Rd, Chester, VT 05143

      115 Reed Rd, Chester, VT 05143
    • 116 Reed Rd, Chester, VT 05143
      116 Reed Rd, Chester, VT 05143
      116 Reed Rd, Chester, VT 05143
      /21

      Est $349,719 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 $251,403 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 $289,023 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 $515,862 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
    • 126 Gould Rd, Chester, VT 05143
      126 Gould Rd, Chester, VT 05143
      126 Gould Rd, Chester, VT 05143
      /25

      Est $499,000 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 $536,200 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 3,313 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 $344,553 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
    • 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
    • 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 $228,246 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 864 Sq Ft

      222 Peck Rd, Chester, VT 05143

      222 Peck Rd, Chester, VT 05143
    • 4351 Route 11, Chester, VT 05143
      4351 Route 11, Chester, VT 05143
      4351 Route 11, Chester, VT 05143
      /18

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 980 Sq Ft

      4351 Route 11, Chester, VT 05143

      4351 Route 11, Chester, VT 05143
    • 2105 White Rd, Chester, VT 05143
      2105 White Rd, Chester, VT 05143
      2105 White Rd, Chester, VT 05143
      /37

      Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,466 Sq Ft

      2105 White Rd, Chester, VT 05143

      2105 White Rd, Chester, VT 05143
    • 341 Whitmore Brook Rd, Chester, VT 05143
      341 Whitmore Brook Rd, Chester, VT 05143
      341 Whitmore Brook Rd, Chester, VT 05143
      /39

      Est $677,185 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,400 Sq Ft

      341 Whitmore Brook Rd, Chester, VT 05143

      341 Whitmore Brook Rd, Chester, VT 05143
    • 0 Smokeshire Rd, Ludlow, VT 05149
      0 Smokeshire Rd, Ludlow, VT 05149
      0 Smokeshire Rd, Ludlow, VT 05149
      /16

      Not Listed For Sale

      0 Smokeshire Rd, Ludlow, VT 05149

      0 Smokeshire Rd, Ludlow, VT 05149
    • 50 Grafton St, Chester, VT 05143
      50 Grafton St, Chester, VT 05143
      50 Grafton St, Chester, VT 05143
      /3

      Est $365,029 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,351 Sq Ft

      50 Grafton St, Chester, VT 05143

      50 Grafton St, Chester, VT 05143
    • 252 Davidson Hill Rd, Chester, VT 05143
      252 Davidson Hill Rd, Chester, VT 05143
      252 Davidson Hill Rd, Chester, VT 05143
      /38

      Est $815,143 Not Listed For Sale

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

      252 Davidson Hill Rd, Chester, VT 05143

      252 Davidson Hill Rd, Chester, VT 05143
    • 64 Maple St, Chester, VT 05143
      64 Maple St, Chester, VT 05143
      64 Maple St, Chester, VT 05143
      /40

      Est $471,736 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,676 Sq Ft

      64 Maple St, Chester, VT 05143

      64 Maple St, Chester, VT 05143
    • 1458 Vt Route 103 S, Chester, VT 05143
      1458 Vt Route 103 S, Chester, VT 05143
      1458 Vt Route 103 S, Chester, VT 05143
      /27

      Est $311,987 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft

      1458 Vt Route 103 S, Chester, VT 05143

      1458 Vt Route 103 S, Chester, VT 05143

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