3,383

Homes in ZIP Code 05143

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  • /42

    $359,000 Sold Nov 05, 2025

    1470 Flamstead Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 803 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Above List Price
    • $447/SF
    • 12 Days On Market

    Current Estimated Value $336,733

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1470 Flamstead Rd, Chester, VT 05143
    • /18

      Est $345,489 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

      • 20% Above List Price
      • $208/SF
      • 2 Days On Market
      • Last Sold Price $288,000
      • Jun 14, 2023

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

  • /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
  • /56

    $805,000 Sold Jan 13, 2026

    1342 Old Stage Rd, Chester, VT 05143

    • 2 Beds
    • 2 Baths
    • 1,576 Sq Ft
    • Built 1971

    Last Sold Summary

    • 10% Below List Price
    • $511/SF
    • 97 Days On Market

    Current Estimated Value $782,319

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    1342 Old Stage Rd, Chester, VT 05143
    • /28

      Est $257,005 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

      • 7% Above List Price
      • $255/SF
      • 4 Days On Market
      • Last Sold Price $240,000
      • Jun 28, 2024

      Last Listing Agent Julie Buffum Buffum Realty

  • /55

    $340,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 2,096 Sq Ft

    335 North St, Chester, VT 05143

    Welcome to a charming village retreat in the heart of Chester, perfectly situated on Main Street in the historic Chester Stone Village. This inviting home blends classic Vermont character with comfortable, year-round living. Enter through a practical mudroom with ample space for all your seasonal gear—ideal for embracing Vermont’s four-season lifestyle. To the right, at the front of the home,

    Brendan McNamara William Raveis Real Estate Vermont Properties

    335 North St, Chester, VT 05143
  • /23

    $59,000 Sold Oct 08, 2025

    58 Remington Rd, Chester, VT 05143

    • Land
    • 2.86 Acres
    • $20,629 per Acre

    Last Sold Summary

    • 25% Below List Price
    • 169 Days On Market

    Current Estimated Value $58,744

    Last Listing Agent John Napier TPW Real Estate

    58 Remington Rd, Chester, VT 05143
    • /40

      Est $497,519 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
      • Apr 15, 2024

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

  • /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
  • /27

    $178,000 Sold Nov 05, 2025

    284 Flamstead Rd, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Built 1969

    Last Sold Summary

    • 6% Below List Price
    • $185/SF
    • 9 Days On Market

    Current Estimated Value $208,921

    Last Listing Agent Linda Benoit Highland Realty

    284 Flamstead Rd, Chester, VT 05143
    • /34

      Est $356,855 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

      • 5% Above List Price
      • $153/SF
      • 10 Days On Market
      • Last Sold Price $340,000
      • Mar 27, 2025

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

  • /9

    $129,000

    • Land
    • 7.95 Acres
    • $16,226 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
  • /49

    $950,000 Sold Dec 05, 2025

    1847 Trebo Rd, Chester, VT 05143

    • 4 Beds
    • 4 Baths
    • 3,920 Sq Ft
    • Built 1849

    Last Sold Summary

    • 19% Below List Price
    • $242/SF
    • 127 Days On Market

    Current Estimated Value $910,364

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

    1847 Trebo Rd, Chester, VT 05143
    • /24

      Est $581,028 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

      • 1% Above List Price
      • $219/SF
      • 4 Days On Market
      • Last Sold Price $575,000
      • Sep 15, 2023

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

  • /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
  • /53

    $550,000 Sold Oct 06, 2025

    1937 Green Mountain Turnpike, Chester, VT 05143

    • 2 Beds
    • 2 Baths
    • 1,812 Sq Ft
    • Built 1864

    Last Sold Summary

    • 3% Below List Price
    • $304/SF
    • 6 Days On Market

    Current Estimated Value $540,618

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    1937 Green Mountain Turnpike, Chester, VT 05143
    • /26

      Est $313,055 Not Listed For Sale

      203 Marcs Dr, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 871 Sq Ft
      • Built 1988
      203 Marcs Dr, Chester, VT 05143

      Last Sold Summary

      • 16% Above List Price
      • $310/SF
      • 0 Days On Market
      • Last Sold Price $270,000
      • Feb 05, 2025

      Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

  • /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. Whether

    Rachael Lange Lange & Lange

    00 Vt Route 103 N, Chester, VT 05143
  • /2

    $421,833 Sold Jul 10, 2025

    332 Hidden Heights Rd, Chester, VT 05143

    • 4 Beds
    • 2.5 Baths
    • 2,868 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Below List Price
    • $147/SF
    • 50 Days On Market

    Current Estimated Value $428,480

    Last Listing Agent John Tolosky Barrett and Valley Associates Inc.

    332 Hidden Heights Rd, Chester, VT 05143
    • /40

      Est $1,280,938 Not Listed For Sale

      683 Church St, Chester, VT 05143

      • 7 Beds
      • 6 Baths
      • 5,566 Sq Ft
      • Built 1801
      683 Church St, Chester, VT 05143

      Last Sold Summary

      • 15% Below List Price
      • $269/SF
      • 236 Days On Market
      • Last Sold Price $1,500,000
      • Aug 04, 2023

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • /18

    $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
  • /10

    $129,000 Sold Feb 24, 2026

    469 Williams Rd, Chester, VT 05143

    • Land
    • 10.88 Acres
    • $11,857 per Acre

    Last Sold Summary

    • 7 Days On Market

    Current Estimated Value $140,473

    Last Listing Agent Chelsea Richardson Barrett and Valley Associates Inc.

    469 Williams Rd, Chester, VT 05143
    • /39

      Est $389,949 Not Listed For Sale

      401 North St, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 1,990 Sq Ft
      • Built 1840
      401 North St, Chester, VT 05143

      Last Sold Summary

      • 10% Above List Price
      • $178/SF
      • 28 Days On Market
      • Last Sold Price $355,000
      • Jul 31, 2024

      Last Listing Agent Jamie Watson BHG Masiello Keene

  • /11

    $85,000 Under Contract

    • 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
  • /53

    $862,000 Sold Jul 18, 2025

    75 Baltimore Rd, North Springfield, VT 05150

    • 5 Beds
    • 3 Baths
    • 4,020 Sq Ft
    • Built 1850

    Last Sold Summary

    • 2% Below List Price
    • $214/SF
    • 63 Days On Market

    Current Estimated Value $881,000

    Last Listing Agent McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    75 Baltimore Rd, North Springfield, VT 05150
    • /28

      Est $375,812 Not Listed For Sale

      250 North St, Chester, VT 05143

      • 5 Beds
      • 2 Baths
      • 2,152 Sq Ft
      • Built 1844
      250 North St, Chester, VT 05143

      Last Sold Summary

      • 30% Above List Price
      • $134/SF
      • 8 Days On Market
      • Last Sold Price $289,000
      • Feb 23, 2024

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

  • /38

    $749,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    717 Horsenail Hill Rd, Chester, VT 05143

    Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances.The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious

    Robin Apps Four Seasons Sotheby's Int'l Realty

    717 Horsenail Hill Rd, Chester, VT 05143
  • /16

    $205,000 Sold Apr 10, 2026

    1876 Popple Dungeon Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1984

    Last Sold Summary

    • $166/SF
    • 6 Days On Market

    Current Estimated Value $207,147

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1876 Popple Dungeon Rd, Chester, VT 05143
    • /39

      Est $375,802 Not Listed For Sale

      312 North St, Chester, VT 05143

      • 4 Beds
      • 1 Bath
      • 2,090 Sq Ft
      • Built 1850
      312 North St, Chester, VT 05143

      Last Sold Summary

      • 17% Above List Price
      • $153/SF
      • 150 Days On Market
      • Last Sold Price $320,000
      • Jun 02, 2023

      Last Listing Agent Heather Gleim CENTURY 21 North East

  • /25

    $229,000

    • Land
    • 27.8 Acres
    • $8,237 per Acre

    00 Quarry Rd, Chester, VT 05143

    Discover your perfect Vermont getaway on this exceptional 27.8± acre hillside parcel in picturesque Chester, Vermont. Offering sweeping mountain views, privacy, and endless possibilities, this property is ready for your vision. With an approved Vermont state wastewater permit for a 4-bedroom home, you can begin designing your dream family retreat or vacation home right away. A cleared preliminary

    Geralyn Donohue Engel & Völkers Okemo

    00 Quarry Rd, Chester, VT 05143
  • /29

    $543,000 Sold Jul 08, 2025

    35 Markham Ln, Weston, VT 05161

    • 3 Beds
    • 1.5 Baths
    • 2,185 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Above List Price
    • $249/SF
    • 38 Days On Market

    Current Estimated Value $553,915

    Last Listing Agent Christiane Carroccio TPW Real Estate

    35 Markham Ln, Weston, VT 05161
    • /37

      Est $635,304 Not Listed For Sale

      332 Marcs Dr, Chester, VT 05143

      • 4 Beds
      • 3.5 Baths
      • 2,795 Sq Ft
      • Built 1988
      332 Marcs Dr, Chester, VT 05143

      Last Sold Summary

      • 8% Above List Price
      • $211/SF
      • 6 Days On Market
      • Last Sold Price $589,000
      • Jul 07, 2023

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /3

    $159,000

    • Land
    • 5 Acres
    • $31,800 per Acre

    00 Contro Rd, Chester, VT 05143

    There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for a homestead farm, little get away cottage or a lovely lodge! Just build the lifestyle you want and forget the rest! A few minutes to Main Street Chester and the Common, A few more to the interstate, and nestled close to skiing, hiking and boating. The WWW permit is issued, town

    Christine Lewis Brattleboro Area Realty

    00 Contro Rd, Chester, VT 05143
  • /56

    $402,239 Sold Nov 12, 2025

    4877 Vt Route 103 N, Chester, VT 05143

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1980

    Last Sold Summary

    • 10% Below List Price
    • $233/SF
    • 10 Days On Market

    Current Estimated Value $407,184

    Last Listing Agent Erin Kendall EXP Realty

    4877 Vt Route 103 N, Chester, VT 05143
    • /40

      Est $234,910 Not Listed For Sale

      244 Main St, Chester, VT 05143

      • 7 Beds
      • 8 Baths
      • 4,475 Sq Ft
      • Built 1825
      244 Main St, Chester, VT 05143

      Last Sold Summary

      • 59% Below List Price
      • $129/SF
      • 70 Days On Market
      • Last Sold Price $579,000
      • Sep 29, 2023

      Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  • /60

    $889,000

    • 3 Beds
    • 2 Baths
    • 3,310 Sq Ft

    201 Spruce Dr, Chester, VT 05143

    Set on over five acres of rolling Vermont hillside, this three-bedroom, two-bath home is perfectly positioned for year-round enjoyment with a special focus on summer living and seamless access to some of southern Vermont’s top mountain destinations, including Okemo Mountain Resort, Stratton Mountain Resort, Bromley Mountain, and Magic Mountain Ski Area. Offered turnkey, it’s an ideal basecamp for

    Mendi Michael Engel & Völkers Okemo

    201 Spruce Dr, Chester, VT 05143
  • /48

    $825,000 Sold Apr 09, 2026

    1269 Howard Hill Rd, Chester, VT 05143

    • 3 Beds
    • 3 Baths
    • 2,172 Sq Ft
    • Built 2024

    Last Sold Summary

    • 8% Below List Price
    • $380/SF
    • 55 Days On Market

    Current Estimated Value $605,267

    Last Listing Agent Cheyanne Pugliese

    1269 Howard Hill Rd, Chester, VT 05143
    • /39

      Est $423,744 Not Listed For Sale

      160 Peck Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 2,068 Sq Ft
      • Built 1925
      160 Peck Rd, Chester, VT 05143

      Last Sold Summary

      • 12% Above List Price
      • $184/SF
      • 5 Days On Market
      • Last Sold Price $380,000
      • Aug 02, 2024

      Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

  • /9

    $195,000

    • Land
    • 1.2 Acres
    • $162,500 per Acre

    4769 Pikes Falls Rd, Jamaica, VT 05143

    This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

    Rachel Febbie EXP Realty

    4769 Pikes Falls Rd, Jamaica, VT 05143
  • /47

    $1,375,000 Sold Sep 30, 2025

    465 Pennell Rd, Chester, VT 05143

    • 4 Beds
    • 4.5 Baths
    • 5,700 Sq Ft
    • Built 1967

    Last Sold Summary

    • 8% Below List Price
    • $241/SF
    • 20 Days On Market

    Current Estimated Value $1,334,703

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

    465 Pennell Rd, Chester, VT 05143

Showing Results 81 - 120, Page 3 of 18

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