3,383

Homes in ZIP Code 05143

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  • /37

    $529,000 Under Contract

    • 5 Beds
    • 5 Baths
    • 3,880 Sq Ft

    514 1st Ave, Chester, VT 05143

    Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chester’s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. It’s a property that allows you to live outwardly—work the land, keep animals,

    Daire Gibney Barrett and Valley Associates Inc.

    514 1st Ave, Chester, 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
    • /18

      Est $330,525 Not Listed For Sale

      3264 Trebo Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,487 Sq Ft
      • Built 1910
      3264 Trebo Rd, Chester, VT 05143

      Last Sold Summary

      • 12% Above List Price
      • $198/SF
      • 41 Days On Market
      • Last Sold Price $295,000
      • Nov 01, 2024

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

  • /44

    $675,000

    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    518 Baltimore Rd, Chester, VT 05143

    Nestled on 10 picturesque rolling acres, just minutes from Chester Village Green and Okemo Mountain Resort, this beautiful country home offers the perfect blend of charm, comfort, and convenience. The property features established gardens, apple trees, blueberry bushes, and a stone patio—ideal for relaxing or entertaining.Inside, you’ll find two levels of well-designed living space. The

    Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    518 Baltimore 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 $254,784

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    154 Reed Rd, Chester, VT 05143
    • /6

      Not Listed For Sale

      00 Vt Route 11 W, Chester, VT 05143

      00 Vt Route 11 W, Chester, VT 05143

      Last Sold Summary

      • 470 Days On Market
      • Last Sold Price $20,000
      • Jan 16, 2024

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

  • /20

    $449,000 Under Contract

    • 5 Beds
    • 1 Bath
    • 2,856 Sq Ft

    127 Trombley Rd, Chester, VT 05143

    Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres in Andover with 5 in Chester. The setting includes over 20 acres of flat, open meadows along the Williams River, framed by wooded hills and distant ridgelines. The forest is mixed with possible timber value as well as a nice sugarbush waiting to be tapped. The original farmhouse, approached by a

    Daire Gibney Barrett and Valley Associates Inc.

    127 Trombley 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 $377,349

    Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

    3091 Route 121, Windham, VT 05359
    • /4

      Est $567,962 Not Listed For Sale

      1709 Potash Brook Rd, Chester, VT 05143

      • 4 Beds
      • 3 Baths
      • 2,688 Sq Ft
      • Built 2008
      1709 Potash Brook Rd, Chester, VT 05143

      Last Sold Summary

      • 16% Above List Price
      • $182/SF
      • 137 Days On Market
      • Last Sold Price $490,000
      • Mar 01, 2024

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /39

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 3,308 Sq Ft

    76 Goldthwaite Rd, Chester, VT 05143

    Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal-style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

    Gary Coger Four Seasons Sotheby's Int'l Realty

    76 Goldthwaite Rd, Chester, 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
    • /29

      Est $337,227 Not Listed For Sale

      201 Hill Top Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,137 Sq Ft
      • Built 1983
      201 Hill Top Rd, Chester, VT 05143

      Last Sold Summary

      • 4% Above List Price
      • $286/SF
      • 18 Days On Market
      • Last Sold Price $325,000
      • Oct 04, 2024

      Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  • /3

    $175,000

    • Land
    • 12.51 Acres
    • $13,989 per Acre

    377 Coach Rd, Chester, VT 05143

    Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home.Located in an area identified for development, it offers both a wonderful building site and long-term

    Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    377 Coach Rd, 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 $273,572

    Last Listing Agent Jim Bialowski BHG Masiello Keene

    230 Kevadus Cir, Chester, VT 05143
    • /25

      Est $302,185 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

      • 10% Above List Price
      • $249/SF
      • 12 Days On Market
      • Last Sold Price $275,000
      • Feb 22, 2024

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • /31

    $299,000

    • 2 Beds
    • 1 Bath
    • 750 Sq Ft

    29 Markham Ln, Weston, VT 05161

    This delightful 2-bedroom, 1-bath cottage located in the heart of the picturesque village of Weston is waiting for a new owner that is looking for a sweet little Vermont retreat. Built in 1947, this home offers timeless character with cozy living spaces and classic Vermont charm. Perfectly situated within walking distance to the Weston Playhouse, the iconic Vermont Country Store, and locally

    Catherine Cairns Maple Leaf Realty

    29 Markham Ln, Weston, VT 05161
  • /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
    • /32

      Est $497,417 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% Above List Price
      • $406/SF
      • 24 Days On Market
      • Last Sold Price $490,000
      • Jul 12, 2024

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

  • /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
  • /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
    • /39

      Est $336,503 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

      • 5% Below List Price
      • $170/SF
      • 19 Days On Market
      • Last Sold Price $355,000
      • Aug 29, 2024

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • /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

    $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 $258,193

    Last Listing Agent Lisa Kelley Cummings & Co

    442 Elm St, Chester, VT 05143
    • /16

      Est $272,961 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% Above List Price
      • $255/SF
      • 6 Days On Market
      • Last Sold Price $257,000
      • Oct 11, 2024

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • /11

    $149,900

    • 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
  • /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 $920,103

    Last Listing Agent Betty McEnaney Diamond Realty

    1502 Popple Dungeon Rd, Chester, VT 05143
    • /37

      Est $252,093 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

      • 1% Below List Price
      • $266/SF
      • 5 Days On Market
      • Last Sold Price $255,000
      • Oct 18, 2024

      Last Listing Agent Frank Provance Diamond Realty

  • /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
  • /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
    • /40

      Est $256,442 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

      • 65% Above List Price
      • $69/SF
      • 114 Days On Market
      • Last Sold Price $155,000
      • May 01, 2023

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  • /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
  • /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
    • /18

      Est $396,386 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

      • 17% Above List Price
      • $127/SF
      • 22 Days On Market
      • Last Sold Price $340,000
      • Sep 15, 2023

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /15

    $85,000 Under Contract

    • 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
  • /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 $378,030

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    270 North St, Chester, VT 05143
    • /30

      Est $354,044 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% Above List Price
      • $276/SF
      • 8 Days On Market
      • Last Sold Price $350,000
      • Jun 23, 2023

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • /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
  • /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 $196,648

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

    1833 Mattson Rd, Chester, VT 05143
    • /34

      Est $467,835 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

      • 18% Below List Price
      • $307/SF
      • 28 Days On Market
      • Last Sold Price $570,000
      • Aug 21, 2024

      Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  • /53

    $359,900 Under Contract

    • 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

Showing Results 41 - 80, Page 2 of 18

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