3,392

Homes in ZIP Code 05143

Section Image
  • 1470 Flamstead Rd, Chester, VT 05143
    1470 Flamstead Rd, Chester, VT 05143
    1470 Flamstead Rd, Chester, VT 05143
    /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 $354,036

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1470 Flamstead Rd, Chester, VT 05143
    • 203 Marcs Dr, Chester, VT 05143
      203 Marcs Dr, Chester, VT 05143
      203 Marcs Dr, Chester, VT 05143
      /26

      Est $311,904

      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

      • 0 Days On Market

  • 00 Vt Route 103 N, Chester, VT 05143
    00 Vt Route 103 N, Chester, VT 05143
    00 Vt Route 103 N, Chester, VT 05143
    /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
  • 1342 Old Stage Rd, Chester, VT 05143
    1342 Old Stage Rd, Chester, VT 05143
    1342 Old Stage Rd, Chester, 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 $803,047

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    1342 Old Stage Rd, Chester, VT 05143
    • 683 Church St, Chester, VT 05143
      683 Church St, Chester, VT 05143
      683 Church St, 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

      • 236 Days On Market

  • 547 Williams Rd, Chester, VT 05143
    547 Williams Rd, Chester, VT 05143
    547 Williams Rd, Chester, VT 05143
    /60

    $474,900

    $24K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    547 Williams Rd, Chester, VT 05143

    MOTIVATED SELLERS welcome you to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, direct access to VAST, located less than an hour from six renowned ski resorts and amenities. So many updates in the past two years; fully remodeled kitchen and bathrooms, fresh paint, new flooring along with numerous updates (list attached in associate documents); modern and

    Terri Edgerley Edge Realty Vermont

    547 Williams Rd, Chester, VT 05143
  • 58 Remington Rd, Chester, VT 05143
    58 Remington Rd, Chester, VT 05143
    58 Remington Rd, 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 $57,998

    Last Listing Agent John Napier TPW Real Estate

    58 Remington Rd, Chester, VT 05143
    • 401 North St, Chester, VT 05143
      401 North St, Chester, VT 05143
      401 North St, Chester, VT 05143
      /39

      Est $382,699

      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

      • 28 Days On Market

  • TBD Farrar Rd, Chester, VT 05143
    TBD Farrar Rd, Chester, VT 05143
    TBD Farrar Rd, Chester, VT 05143
    /24

    $74,500

    Under Contract
    • 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
  • 284 Flamstead Rd, Chester, VT 05143
    284 Flamstead Rd, Chester, VT 05143
    284 Flamstead Rd, Chester, 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 $221,989

    Last Listing Agent Linda Benoit Highland Realty

    284 Flamstead Rd, Chester, VT 05143
    • 196 North St, Chester, VT 05143
      196 North St, Chester, VT 05143
      196 North St, Chester, VT 05143
      /60

      Est $400,417

      Not Listed For Sale

      196 North St, Chester, VT 05143

      • 3 Beds
      • 3 Baths
      • 2,960 Sq Ft
      • Built 1844
      196 North St, Chester, VT 05143

      Last Sold Summary

      • 166 Days On Market

  • 717 Horsenail Hill Rd, Chester, VT 05143
    717 Horsenail Hill Rd, Chester, VT 05143
    717 Horsenail Hill Rd, Chester, VT 05143
    /38

    $695,000

    New Construction $94K PRICE DROP
    • 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
  • 1847 Trebo Rd, Chester, VT 05143
    1847 Trebo Rd, Chester, VT 05143
    1847 Trebo Rd, 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 $817,175

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

    1847 Trebo Rd, Chester, VT 05143
    • 250 North St, Chester, VT 05143
      250 North St, Chester, VT 05143
      250 North St, Chester, VT 05143
      /28

      Est $358,924

      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

      • 8 Days On Market

  • 3668 Vt Route 103 N, Chester, VT 05143
    3668 Vt Route 103 N, Chester, VT 05143
    3668 Vt Route 103 N, Chester, VT 05143
    /38

    $249,500

    • 1,922 Sq Ft

    3668 Vt Route 103 N, Chester, VT 05143

    Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits.The home is currently configured as two charming

    Daniel Vigeant Mary W. Davis Realtor & Assoc., Inc.

    3668 Vt Route 103 N, Chester, VT 05143
  • 1937 Green Mountain Turnpike, Chester, VT 05143
    1937 Green Mountain Turnpike, Chester, VT 05143
    1937 Green Mountain Turnpike, 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 $557,790

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    1937 Green Mountain Turnpike, Chester, VT 05143
    • 332 Marcs Dr, Chester, VT 05143
      332 Marcs Dr, Chester, VT 05143
      332 Marcs Dr, Chester, VT 05143
      /37

      Est $650,249

      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

      • 6 Days On Market

  • 00 Contro Rd, Chester, VT 05143
    00 Contro Rd, Chester, VT 05143
    00 Contro Rd, Chester, VT 05143
    /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
  • 332 Hidden Heights Rd, Chester, VT 05143
    332 Hidden Heights Rd, 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 $503,985

    Last Listing Agent John Tolosky Barrett and Valley Associates Inc.

    332 Hidden Heights Rd, Chester, VT 05143
    • 244 Main St, Chester, VT 05143
      244 Main St, Chester, VT 05143
      244 Main St, Chester, VT 05143
      /40

      Est $231,360

      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

      • 70 Days On Market

  • 201 Spruce Dr, Chester, VT 05143
    201 Spruce Dr, Chester, VT 05143
    201 Spruce Dr, Chester, VT 05143
    /60

    $879,999

    $9K PRICE DROP
    • 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
  • 469 Williams Rd, Chester, VT 05143
    469 Williams Rd, Chester, VT 05143
    469 Williams 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 $129,687

    Last Listing Agent Chelsea Richardson Barrett and Valley Associates Inc.

    469 Williams Rd, Chester, VT 05143
    • 160 Peck Rd, Chester, VT 05143
      160 Peck Rd, Chester, VT 05143
      160 Peck Rd, Chester, VT 05143
      /39

      Est $415,046

      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

      • 5 Days On Market

  • 4769 Pikes Falls Rd, Jamaica, VT 05143
    4769 Pikes Falls Rd, Jamaica, VT 05143
    4769 Pikes Falls Rd, Jamaica, VT 05143
    /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
  • 75 Baltimore Rd, North Springfield, VT 05150
    75 Baltimore Rd, North Springfield, VT 05150
    75 Baltimore Rd, North Springfield, VT 05150
    /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 $824,777

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

    75 Baltimore Rd, North Springfield, VT 05150
    • 835 Quarry Rd, Chester, VT 05143
      835 Quarry Rd, Chester, VT 05143
      835 Quarry Rd, Chester, VT 05143
      /34

      Est $911,536

      Not Listed For Sale

      835 Quarry Rd, Chester, VT 05143

      • 3 Beds
      • 4 Baths
      • 2,221 Sq Ft
      • Built 1998
      835 Quarry Rd, Chester, VT 05143

      Last Sold Summary

      • 4 Days On Market

  • 00 Little Pond Rd, Andover, VT 05143
    00 Little Pond Rd, Andover, VT 05143
    00 Little Pond Rd, Andover, VT 05143
    /16

    $650,000

    • Land
    • 10.03 Acres
    • $64,806 per Acre

    00 Little Pond Rd, Andover, VT 05143

    Located in the town of Andover, VT, this 10.4 acre parcel, showcasing an amazing long range mountain view, awaits the home of your dreams. The approach to the property is gorgeous with dramatic views and large neighboring parcels. The house site is tucked in the forest, with a roughed-in driveway already in place. This property has been thoughtfully composed, setting the stage for your custom

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    00 Little Pond Rd, Andover, VT 05143
  • 202 Mountain View, Chester, VT 05143
    202 Mountain View, Chester, VT 05143
    202 Mountain View, Chester, VT 05143
    /20

    $250,000

    Sold Jun 30, 2026

    202 Mountain View, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,140 Sq Ft
    • Built 1945

    Last Sold Summary

    • $219/SF
    • 5 Days On Market

    Current Estimated Value $246,118

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    202 Mountain View, Chester, VT 05143
    • 50 Howard Rd, Chester, VT 05143
      50 Howard Rd, Chester, VT 05143
      50 Howard Rd, Chester, VT 05143
      /59

      Est $561,752

      Not Listed For Sale

      50 Howard Rd, Chester, VT 05143

      • 3 Beds
      • 2.5 Baths
      • 1,728 Sq Ft
      • Built 1986
      50 Howard Rd, Chester, VT 05143

      Last Sold Summary

      • 27 Days On Market

  • 00 Remington Rd, Chester, VT 05143
    00 Remington Rd, Chester, VT 05143
    00 Remington Rd, Chester, VT 05143
    /14

    $74,000

    • Land
    • 15.5 Acres
    • $4,774 per Acre

    00 Remington Rd, Chester, VT 05143

    Bring your ideas for building your own home on this 15.5 acre parcel of land in the quintessential town of Chester. Located minutes to the 91 FWY. Vermont Academy nearby along with several hiking and snowmobile trails. Seller has included the cost for clearing the building site and a driveway to house site. Come look at this property and enjoy all it has to offer.

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    00 Remington Rd, Chester, VT 05143
  • 1876 Popple Dungeon Rd, Chester, VT 05143
    1876 Popple Dungeon Rd, Chester, VT 05143
    1876 Popple Dungeon 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 $206,898

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1876 Popple Dungeon Rd, Chester, VT 05143
    • 50 Goldthwaite Rd, Chester, VT 05143
      50 Goldthwaite Rd, Chester, VT 05143
      50 Goldthwaite Rd, Chester, VT 05143
      /33

      Est $643,046

      Not Listed For Sale

      50 Goldthwaite Rd, Chester, VT 05143

      • 3 Beds
      • 2 Baths
      • 2,214 Sq Ft
      • Built 1987
      50 Goldthwaite Rd, Chester, VT 05143

      Last Sold Summary

      • 27 Days On Market

  • 0 Valley View Dr Unit 5009431, Andover, VT 05143
    0 Valley View Dr Unit 5009431, Andover, VT 05143
    0 Valley View Dr Unit 5009431, Andover, VT 05143
    /21

    $135,000

    $130K PRICE DROP
    • Land
    • 13.96 Acres
    • $9,670 per Acre

    0 Valley View Dr Unit 5009431, Andover, VT 05143

    UNBELIEVABLE VALUE in a great setting ! Bordering the Ludlow line and set at an elevation of 2,000+ feet, this exceptional parcel offers privacy, expansive long-range views, and an ideal setting for your Southern Vermont dream home. Located within a peaceful community of fine homes, this is one of the few remaining opportunities to build in this highly desirable area. The property includes a

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    0 Valley View Dr Unit 5009431, Andover, VT 05143
  • 35 Markham Ln, Weston, VT 05161
    35 Markham Ln, Weston, VT 05161
    35 Markham Ln, Weston, VT 05161
    /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 $541,636

    Last Listing Agent Christiane Carroccio TPW Real Estate

    35 Markham Ln, Weston, VT 05161
    • 83 Potash Brook Rd, Chester, VT 05143
      83 Potash Brook Rd, Chester, VT 05143
      83 Potash Brook Rd, Chester, VT 05143
      /19

      Est $210,589

      Not Listed For Sale

      83 Potash Brook Rd, Chester, VT 05143

      • 2 Beds
      • 500 Sq Ft
      • Built 1970
      83 Potash Brook Rd, Chester, VT 05143

      Last Sold Summary

      • 211 Days On Market

  • 000 Green Mountain Turnpike, Andover, VT 05143
    000 Green Mountain Turnpike, Andover, VT 05143
    000 Green Mountain Turnpike, Andover, VT 05143
    /22

    $249,000

    $50K PRICE DROP
    • Land
    • 84 Acres
    • $2,964 per Acre

    000 Green Mountain Turnpike, Andover, VT 05143

    84+/- Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this property

    Daire Gibney Barrett and Valley Associates Inc.

    000 Green Mountain Turnpike, Andover, VT 05143
  • 4877 Vt Route 103 N, Chester, VT 05143
    4877 Vt Route 103 N, Chester, VT 05143
    4877 Vt Route 103 N, 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 $441,953

    Last Listing Agent Erin Kendall EXP Realty

    4877 Vt Route 103 N, Chester, VT 05143
    • 154 Fletcher Hill Rd, Chester, VT 05143
      154 Fletcher Hill Rd, Chester, VT 05143
      154 Fletcher Hill Rd, Chester, VT 05143
      /26

      Est $343,841

      Not Listed For Sale

      154 Fletcher Hill Rd, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,300 Sq Ft
      • Built 1979
      154 Fletcher Hill Rd, Chester, VT 05143

      Last Sold Summary

      • 52 Days On Market

  • 00 Valley View Dr, Andover, VT 05143
    00 Valley View Dr, Andover, VT 05143
    00 Valley View Dr, Andover, VT 05143
    /17

    $485,000

    • Land
    • 26.99 Acres
    • $17,970 per Acre

    00 Valley View Dr, Andover, VT 05143

    A premier location abutting the Ludlow border, close to Okemo with total privacy, long range panoramic views of distant mountains and valleys at an elevation of about 2000 feet. Peace and beauty abound yet easy access to all area amenities including skiing, golf, biking, hiking and all that Southern Vermont has to offer. A State wastewater permit is in place for a 6 bedroom home and a 2 bedroom

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    00 Valley View Dr, Andover, VT 05143
  • 1269 Howard Hill Rd, Chester, VT 05143
    1269 Howard Hill Rd, Chester, VT 05143
    1269 Howard Hill Rd, 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 $824,804

    Last Listing Agent Cheyanne Pugliese

    1269 Howard Hill Rd, Chester, VT 05143

Showing Results 81 - 120, Page 3 of 18

Vermont Windsor County Chester 05143

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