3,368

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 $361,936

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1470 Flamstead Rd, Chester, VT 05143
    • /26

      Est $322,299 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

      • 19% Above List Price
      • $310/SF
      • 0 Days On Market

      Last Sold Price $270,000

      Last Listing Agent Sarah Sheehan William Raveis Real Estate Vermont Properties

  • /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
  • /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 $851,028

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    1342 Old Stage Rd, Chester, VT 05143
    • /40

      Est $1,369,102 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

      • 9% Below List Price
      • $269/SF
      • 236 Days On Market

      Last Sold Price $1,500,000

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • /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
  • /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 $59,194

    Last Listing Agent John Napier TPW Real Estate

    58 Remington Rd, Chester, VT 05143
    • /39

      Est $351,480 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

      • 1% Below List Price
      • $178/SF
      • 28 Days On Market

      Last Sold Price $355,000

      Last Listing Agent Jamie Watson BHG Masiello Keene

  • /60

    $889,000

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

    201 Spruce Dr, Chester, VT 05143

    Situated on more than five acres of rolling Vermont hillside, this three bedroom, two bath home offers effortless access to Okemo, Stratton, Bromley, and Magic ski resorts and is being sold turnkey. Designed for those who value both comfort and connection to the outdoors, the home delivers updated living space surrounded by peaceful countryside. Nearby VAST trail access and a sweeping wraparound

    Mendi Michael Engel & Völkers Okemo

    201 Spruce Dr, Chester, VT 05143
  • /2

    $285,000 Sold Mar 26, 2025

    17 Grafton St, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft
    • Built 1852

    Last Sold Summary

    • 2% Below List Price
    • $156/SF
    • 87 Days On Market

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

    17 Grafton St, Chester, VT 05143
    • /28

      Est $384,236 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

      • 33% Above List Price
      • $134/SF
      • 8 Days On Market

      Last Sold Price $289,000

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

  • /24

    $89,000

    • Land
    • 10.4 Acres
    • $8,558 per Acre

    0 Snell Rd, Chester, VT 05143

    This rolling, wooded 10.4+/- acre surveyed parcel in Chester offers 244 feet of road frontage and gently rolling land with a mix of hardwoods and pine. A lovely stream meanders through the property which is also dotted with interesting large boulders and old stone walls. If you are looking for privacy, there is potential for a secluded home site set back from the road. Utility pole is at the road

    Geralyn Donohue Engel & Völkers Okemo

    0 Snell 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 $200,377

    Last Listing Agent Linda Benoit Highland Realty

    284 Flamstead Rd, Chester, VT 05143
    • /39

      Est $358,324 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

      • 12% Above List Price
      • $153/SF
      • 150 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Heather Gleim CENTURY 21 North East

  • /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
  • /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 $886,020

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

    1847 Trebo Rd, Chester, VT 05143
    • /37

      Est $624,886 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% Above List Price
      • $211/SF
      • 6 Days On Market

      Last Sold Price $589,000

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /21

    $150,000

    • Land
    • 13.96 Acres
    • $10,745 per Acre

    0 Valley View Dr Unit 5009431, Andover, VT 05143

    Great Value in a great setting ! 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 state-approved wastewater permit and

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    0 Valley View Dr Unit 5009431, Andover, 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 $543,493

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    1937 Green Mountain Turnpike, Chester, VT 05143
    • /10

      Est $317,709 Not Listed For Sale

      784 Vt Route 103 N, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,214 Sq Ft
      • Built 1972
      784 Vt Route 103 N, Chester, VT 05143

      Last Sold Summary

      • 38% Above List Price
      • $190/SF
      • 124 Days On Market

      Last Sold Price $231,000

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

  • /22

    $275,000

    • Land
    • 91 Acres
    • $3,022 per Acre

    000 Green Mountain Turnpike, Andover, VT 05143

    91± Acres with Stunning Mountain Views in Chester, VermontDiscover a breathtaking 91± acre 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

    Daire Gibney Barrett and Valley Associates Inc.

    000 Green Mountain Turnpike, Andover, 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 $425,093

    Last Listing Agent John Tolosky Barrett and Valley Associates Inc.

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

      Est $248,811 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

      • 57% Below List Price
      • $129/SF
      • 70 Days On Market

      Last Sold Price $579,000

      Last Listing Agent Katie Ladue Gilbert KW Vermont Woodstock

  • /12

    $219,000

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    419 Coach Rd, Chester, VT 05143

    Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.

    Amy Carson Lowe's Real Estate, LLC

    419 Coach 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 $163,293

    Last Listing Agent Chelsea Richardson Barrett and Valley Associates Inc.

    469 Williams Rd, Chester, VT 05143
    • /39

      Est $415,541 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

      • 9% Above List Price
      • $184/SF
      • 5 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

  • /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
  • /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 $944,129

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

    75 Baltimore Rd, North Springfield, VT 05150
    • /34

      Est $918,206 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

      • 3% Below List Price
      • $425/SF
      • 4 Days On Market

      Last Sold Price $945,000

      Last Listing Agent Alison Cummings Cummings & Co

  • /43

    $250,000

    • 3 Beds
    • 1 Bath
    • 980 Sq Ft

    64 County Rd, North Springfield, VT 05150

    Enjoy the ease of single-level living in this 2008 single-wide home set on 2.5 peaceful Vermont acres. The open-concept kitchen and living area is filled with natural light, creating a warm and inviting atmosphere. Offering three bedrooms, one full bath, and a convenient laundry area. Recent improvements include new carpeting and fresh interior paint, making this home truly move-in ready. The

    Carol Slocum Keller Williams Realty Metro-Keene

    64 County Rd, North Springfield, VT 05150
  • /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 $591,600

    Last Listing Agent Christiane Carroccio TPW Real Estate

    35 Markham Ln, Weston, VT 05161
    • /59

      Est $561,842 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

      • 8% Below List Price
      • $352/SF
      • 27 Days On Market

      Last Sold Price $608,000

      Last Listing Agent Jeremy Collins Ridgeline Real Estate

  • /31

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft

    1397 Popple Dungeon Rd, Chester, VT 05143

    Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for—flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved

    Daire Gibney Barrett and Valley Associates Inc.

    1397 Popple Dungeon 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 $406,359

    Last Listing Agent Erin Kendall EXP Realty

    4877 Vt Route 103 N, Chester, VT 05143
    • /33

      Est $655,222 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

      • 7% Below List Price
      • $318/SF
      • 27 Days On Market

      Last Sold Price $705,000

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

  • /30

    $650,000

    • 3 Beds
    • 3 Baths
    • 4,324 Sq Ft

    3630 Vt Route 103 N, Chester, VT 05143

    Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3630 Vt Route 103 N, Chester, 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 $1,330,738

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

    465 Pennell Rd, Chester, VT 05143
    • /39

      Est $817,200 Not Listed For Sale

      76 Goldthwaite Rd, Chester, VT 05143

      • 4 Beds
      • 3 Baths
      • 3,308 Sq Ft
      • Built 1864
      76 Goldthwaite Rd, Chester, VT 05143

      Last Sold Summary

      • 7% Below List Price
      • $266/SF
      • 33 Days On Market

      Last Sold Price $881,000

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

  • /41

    $5,950,000

    • 8 Beds
    • 7.5 Baths
    • 10,062 Sq Ft

    3800 Weston-Andover Rd, Andover, VT 05143

    The ultimate family compound, award nominated video tour. This fully furnished and equipped luxury property is located in Andover, Vermont, set on 384 acres in the iconic Green Mountains, offering a rare blend of nature’s bounty, seclusion, and timeless craftsmanship. The custom built 10,062 square foot main house features an expansive open concept design. Crafted with post and beam timber frame

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    3800 Weston-Andover Rd, Andover, VT 05143
  • /2

    $70,000 Sold Oct 21, 2025

    Lot 2 Old Stage Rd, Chester, VT 05143

    • Land
    • 6.3 Acres
    • $11,111 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 35 Days On Market

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    Lot 2 Old Stage Rd, Chester, VT 05143

Showing Results 81 - 120, Page 3 of 18

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