3,392

Homes in ZIP Code 05143

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  • 223 Coach Rd, Chester, VT 05143
    223 Coach Rd, Chester, VT 05143
    223 Coach Rd, Chester, VT 05143
    /44

    $849,000

    • 5 Beds
    • 3 Baths
    • 4,388 Sq Ft

    223 Coach Rd, Chester, VT 05143

    Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to

    Daire Gibney Barrett and Valley Associates Inc.

    223 Coach Rd, Chester, VT 05143
  • 154 Reed Rd, Chester, VT 05143
    154 Reed Rd, Chester, VT 05143
    /2

    $345,000

    Sold Oct 07, 2025

    154 Reed Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $308/SF
    • 10 Days On Market

    Current Estimated Value $248,331

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    154 Reed Rd, Chester, VT 05143
    • 8 Route 35, Athens, VT 05143
      8 Route 35, Athens, VT 05143
      8 Route 35, Athens, VT 05143
      /25

      Est $297,036

      Not Listed For Sale

      8 Route 35, Athens, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,106 Sq Ft
      • Built 1980
      8 Route 35, Athens, VT 05143

      Last Sold Summary

      • 12 Days On Market

  • 106 Contro Rd, Chester, VT 05143
    106 Contro Rd, Chester, VT 05143
    106 Contro Rd, Chester, VT 05143
    /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
  • 3091 Route 121, Windham, VT 05359
    3091 Route 121, Windham, VT 05359
    3091 Route 121, Windham, VT 05359
    /41

    $364,000

    Sold Aug 15, 2025

    3091 Route 121, Windham, VT 05359

    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • Built 1860

    Last Sold Summary

    • 8% Below List Price
    • $207/SF
    • 22 Days On Market

    Current Estimated Value $374,534

    Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

    3091 Route 121, Windham, VT 05359
    • 15 Markham Ln, Weston, VT 05161
      15 Markham Ln, Weston, VT 05161
      15 Markham Ln, Weston, VT 05161
      /32

      Est $507,484

      Not Listed For Sale

      15 Markham Ln, Weston, VT 05161

      • 2 Beds
      • 2 Baths
      • 1,208 Sq Ft
      • Built 1940
      15 Markham Ln, Weston, VT 05161

      Last Sold Summary

      • 24 Days On Market

  • 360 Dorman Rd, Andover, VT 05143
    360 Dorman Rd, Andover, VT 05143
    360 Dorman Rd, Andover, VT 05143
    /11

    $149,900

    Under Contract
    • Land
    • 12.7 Acres
    • $11,803 per Acre

    360 Dorman Rd, Andover, VT 05143

    Discover the perfect blend of privacy, natural beauty, and convenience on this stunning 12.7-acre parcel nestled in the heart of the Green Mountains in Andover. This mostly wooded property offers a peaceful, secluded setting with a cleared homesite ideally positioned for southern exposure and the potential for breathtaking long-range mountain views with additional clearing.A 5-bedroom

    Gary Coger Four Seasons Sotheby's Int'l Realty

    360 Dorman Rd, Andover, VT 05143
  • 00 Boone Rd, Andover, VT 05143
    00 Boone Rd, Andover, VT 05143
    00 Boone Rd, Andover, VT 05143
    /60

    $40,000

    Sold Jul 11, 2025

    00 Boone Rd, Andover, VT 05143

    • Land
    • 5 Acres
    • $8,000 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 77 Days On Market

    Last Listing Agent Rachael Lange Lange & Lange

    00 Boone Rd, Andover, VT 05143
    • 43 Northfield Dr, North Springfield, VT 05150
      43 Northfield Dr, North Springfield, VT 05150
      43 Northfield Dr, North Springfield, VT 05150
      /39

      Est $356,057

      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

      • 19 Days On Market

  • 663 Depot St, Chester, VT 05143
    663 Depot St, Chester, VT 05143
    663 Depot St, Chester, VT 05143
    /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
  • 230 Kevadus Cir, Chester, VT 05143
    230 Kevadus Cir, Chester, VT 05143
    230 Kevadus Cir, 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 $278,909

    Last Listing Agent Jim Bialowski BHG Masiello Keene

    230 Kevadus Cir, Chester, VT 05143
    • 192 Kevadus Cir, Chester, VT 05143
      192 Kevadus Cir, Chester, VT 05143
      192 Kevadus Cir, Chester, VT 05143
      /16

      Est $269,674

      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 Days On Market

  • 688 Hidden Heights Rd, Chester, VT 05143
    688 Hidden Heights Rd, Chester, VT 05143
    688 Hidden Heights Rd, Chester, VT 05143
    /60

    $649,000

    • 3 Beds
    • 2 Baths
    • 2,205 Sq Ft

    688 Hidden Heights Rd, Chester, VT 05143

    Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of the

    Joseph Karl William Raveis Real Estate Vermont Properties

    688 Hidden Heights Rd, Chester, VT 05143
  • 2739 Route 11, Chester, VT 05143
    2739 Route 11, 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
    • 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

      Est $253,286

      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

      • 5 Days On Market

  • 0 E Hill Rd, Andover, VT 05143
    0 E Hill Rd, Andover, VT 05143
    0 E Hill Rd, Andover, VT 05143
    /17

    $225,000

    • Land
    • 27.2 Acres
    • $8,272 per Acre

    0 E Hill Rd, Andover, VT 05143

    Nestled in the heart of Vermont’s scenic countryside, this beautiful 27.2-acre parcel offers the perfect setting to build your dream home or mountain retreat. Mostly wooded with over 800 feet of road frontage, the property combines privacy, natural beauty, and easy access to some of Southern Vermont’s most desirable destinations.Enjoy mountain and scenic views that provide ideal building

    Gary Coger Four Seasons Sotheby's Int'l Realty

    0 E Hill Rd, Andover, 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

  • 794 White Rd, Windham, VT 05359
    794 White Rd, Windham, VT 05359
    794 White Rd, Windham, VT 05359
    /60

    $549,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 850 Sq Ft

    794 White Rd, Windham, VT 05359

    Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

    Erica Reynolds Southern Vermont Realty Group

    794 White Rd, Windham, VT 05359
  • 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

  • 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
  • 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

  • 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
  • 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

  • 0 Markham Mountain Rd, Andover, VT 05143
    0 Markham Mountain Rd, Andover, VT 05143
    0 Markham Mountain Rd, Andover, VT 05143
    /19

    $595,000

    • Land
    • 220.11 Acres
    • $2,703 per Acre

    0 Markham Mountain Rd, Andover, VT 05143

    Discover 220± acres of pristine woodland offering the ultimate blend of privacy, recreation, and opportunity. With a mix of gently level terrain and elevated ridgelines that may offer sweeping mountain views, this remarkable parcel provides endless possibilities — from a private estate setting to potential subdivision. The VAST snowmobile trail runs directly through a portion of the property,

    Kevin Barnes William Raveis Real Estate Vermont Properties

    0 Markham Mountain Rd, Andover, 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

  • 330 Spruce Dr, Andover, VT 05143
    330 Spruce Dr, Andover, VT 05143
    330 Spruce Dr, Andover, VT 05143
    /58

    $880,000

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft

    330 Spruce Dr, Andover, VT 05143

    Mountain View Timber Frame Retreat on 25+ Acres in Andover – This exceptional timber-frame home is true perfection and offers long-range mountain views, sunny southeastern exposure, and complete privacy and access to everything that makes you want to call Vermont home. The authentic post-and-beam retreat blends timeless craftsmanship with modern comfort and is offered fully furnished, making it

    Claudia Harris Mary Mitchell Miller Real Estate

    330 Spruce Dr, Andover, 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

  • 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
  • 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

  • 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
  • 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

  • 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

Showing Results 41 - 80, Page 2 of 18

Vermont Windsor County Chester 05143

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