3,368

Homes in ZIP Code 05143

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  • /16

    $3,150,000

    • Land
    • 506 Acres
    • $6,225 per Acre

    00 Marsh Cross Rd, Andover, VT 05143

    Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence. This land's historical roots run deep, originally belonging to the Marsh

    Story Jenks LandVest, Inc/Woodstock

    00 Marsh Cross Rd, Andover, VT 05143
  • /58

    $475,000 Sold Oct 10, 2025

    1923 N Hill Rd, Chester, VT 05143

    • 5 Beds
    • 3 Baths
    • 2,316 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $205/SF
    • 6 Days On Market

    Last Listing Agent Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    1923 N Hill Rd, Chester, VT 05143
    • /32

      Est $480,217 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

      • 2% Below List Price
      • $406/SF
      • 24 Days On Market

      Last Sold Price $490,000

      Last Listing Agent Steve Stettler Four Seasons Sotheby's Int'l Realty

  • /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

    $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 $241,677

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    154 Reed Rd, Chester, VT 05143
    • /39

      Est $340,471 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

      • 4% Below List Price
      • $170/SF
      • 19 Days On Market

      Last Sold Price $355,000

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • /36

    $369,000

    • 5 Beds
    • 1 Bath
    • 2,243 Sq Ft

    2029 N Hill Rd, Chester, VT 05143

    Come, enjoy the quiet charm of Andover in this inviting, private Vermont home—perfect for year-round living or a peaceful getaway. Nestled among evergreens with beautiful snowy views, this property offers easy access to Okemo Mountain, and is also close to Stratton, Magic, and Bromley for skiing, riding, and four-season adventure. Snowmobile enthusiasts will love the nearby VAST trails, and the

    Daire Gibney Barrett and Valley Associates Inc.

    2029 N Hill Rd, Chester, VT 05143
  • /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 $413,237

    Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

    3091 Route 121, Windham, VT 05359
    • /14

      Est $273,018 Not Listed For Sale

      184 Kevadus Cir, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1988
      184 Kevadus Cir, Chester, VT 05143

      Last Sold Summary

      • 21% Above List Price
      • $223/SF
      • 9 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /37

    $1,995,000

    • 4 Beds
    • 2.5 Baths
    • 3,839 Sq Ft

    198 Piper Hill Rd, Weston, VT 05161

    Uplands is a gracious 105-acre hill farm on the south-facing slope of Markham Mountain, located just outside the historic village of Weston. Anchored by an 1800s farmhouse, the main residence has been thoughtfully added on to and renovated over the years and offers over 3,839 square feet of living space, including four bedrooms, three fireplaces and an attached two bay garage. The guest house

    Story Jenks LandVest, Inc/Woodstock

    198 Piper Hill Rd, Weston, VT 05161
  • /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 Rogala Lange & Lange

    00 Boone Rd, Andover, VT 05143
    • /16

      Est $266,227 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

      • 4% Above List Price
      • $255/SF
      • 6 Days On Market

      Last Sold Price $257,000

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • /15

    $85,000

    • Land
    • 4.05 Acres
    • $20,988 per Acre

    00 Hillcrest Dr, Andover, VT 05143

    Ready to Build in Southern Vermont! Dreaming of a serene mountain getaway or your forever home in Vermont? This 4.± acre gem on a quiet dead-end road offers peace, privacy, and convenience. With a State-issued wastewater permit already in hand for a 5-bedroom home, you can hit the ground running on your build. Power is right at the road and fiber-optic internet is available—ideal for remote work

    Daire Gibney Barrett and Valley Associates Inc.

    00 Hillcrest Dr, Andover, 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 $281,959

    Last Listing Agent Jim Bialowski BHG Masiello Keene

    230 Kevadus Cir, Chester, VT 05143
    • /37

      Est $255,288 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

      • $266/SF
      • 5 Days On Market

      Last Sold Price $255,000

      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
  • /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
    • /40

      Est $251,422 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

      • 62% Above List Price
      • $69/SF
      • 114 Days On Market

      Last Sold Price $155,000

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  • /53

    $390,000

    • 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
  • /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
    • /18

      Est $423,939 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

      • 25% Above List Price
      • $127/SF
      • 22 Days On Market

      Last Sold Price $340,000

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /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
  • /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 $260,171

    Last Listing Agent Lisa Kelley Cummings & Co

    442 Elm St, Chester, VT 05143
    • /30

      Est $346,573 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% Below List Price
      • $276/SF
      • 8 Days On Market

      Last Sold Price $350,000

      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 Rogala Lange & Lange

    00 Vermont 103, Andover, 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 $946,252

    Last Listing Agent Betty McEnaney Diamond Realty

    1502 Popple Dungeon Rd, Chester, VT 05143
    • /34

      Est $450,901 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

      • 21% Below List Price
      • $307/SF
      • 28 Days On Market

      Last Sold Price $570,000

      Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  • /16

    $205,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    1876 Popple Dungeon Rd, Chester, VT 05143

    Charming opportunity on 3.18 open acres with a stream along the back of the property adding natural beauty and a peaceful setting. This 3-bedroom ranch offers easy single-level living and a functional layout, ready for updates and your personal touch. Ideal for handy buyers, renovators, or buyers looking to build equity. The spacious land provides room for gardening, animals, recreation, or

    Thaddeus Abare Barrett and Valley Associates Inc.

    1876 Popple Dungeon Rd, 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 $332,721 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

      • 16% Above List Price
      • $208/SF
      • 2 Days On Market

      Last Sold Price $288,000

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

    Rachael Rogala Lange & Lange

    00 Vt Route 103 N, 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
    • /28

      Est $253,802 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

      • 6% Above List Price
      • $255/SF
      • 4 Days On Market

      Last Sold Price $240,000

      Last Listing Agent Julie Buffum Buffum Realty

  • /16

    $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
  • /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 $408,057

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    270 North St, Chester, VT 05143
    • /40

      Est $497,455 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

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

  • /48

    $899,000 Under Contract

    • 3 Beds
    • 3 Baths
    • 2,172 Sq Ft

    1269 Howard Hill Rd, Chester, VT 05143

    Discover a truly one-of-a-kind Vermont retreat set on 10 acres of peaceful woodland and open meadow. Originally built as a family-run maple sugar shack, this architect-designed home has been thoughtfully reimagined and newly completed, seamlessly blending rustic charm with contemporary comfort to create a warm and inviting hideaway unlike anything else on the market. Post-and-beam construction,

    Cheyanne Pugliese

    1269 Howard Hill 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 $198,308

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

    1833 Mattson Rd, Chester, VT 05143
    • /24

      Est $545,448 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

      • 5% Below List Price
      • $219/SF
      • 4 Days On Market

      Last Sold Price $575,000

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

  • /11

    $85,000

    • Land
    • 15.68 Acres
    • $5,421 per Acre

    00 E Hill Rd, Andover, VT 05143

    Rooted in along scenic East Hill Road in the bucolic town of Andover, this 16-acre parcel offers a rare opportunity to create your own private haven in one of Southern Vermont’s most peaceful and charming settings. Just minutes from Ludlow and the slopes of Okemo Mountain, this location strikes the perfect balance between quiet countryside and convenient access to skiing, shopping, dining, and

    Daire Gibney Barrett and Valley Associates Inc.

    00 E Hill Rd, Andover, VT 05143

Showing Results 41 - 80, Page 2 of 18

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