2,737

Chester, VT Homes

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  • /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
    • /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

  • /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
  • /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
    • /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

  • /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
  • /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
    • /39

      Est $380,636 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

      • 7% 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

  • /28

    $89,000

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

    0 Snell Rd, Chester, VT 05143

    Rolling, wooded 10.4+/- acre surveyed parcel in Chester offering 244 feet of road frontage and 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. Atop the plateau further into the lot there are nice

    Geralyn Donohue Engel & Völkers Okemo

    0 Snell 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
    • /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

  • /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
  • /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

  • /22

    $249,000

    • 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
  • /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
    • /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.

  • /12

    $219,000 Under Contract

    • 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
  • /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
    • /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

  • /31

    $349,000

    • 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
  • /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
    • /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

  • /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
  • /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
    • /34

      Est $904,036 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% Below List Price
      • $425/SF
      • 4 Days On Market
      • Last Sold Price $945,000
      • Sep 10, 2023

      Last Listing Agent Alison Cummings Cummings & Co

  • /37

    $399,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,148 Sq Ft

    40 Fenton Rd, Chester, VT 05143

    This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of

    John Napier TPW Real Estate

    40 Fenton Rd, Chester, VT 05143
  • /2

    $165,000 Sold Oct 23, 2025

    1436 Route 103, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft
    • Built 1825

    Last Sold Summary

    • 4% Above List Price
    • $107/SF
    • 2 Days On Market

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    1436 Route 103, Chester, VT 05143
    • /59

      Est $562,824 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

      • 7% Below List Price
      • $352/SF
      • 27 Days On Market
      • Last Sold Price $608,000
      • Dec 27, 2024

      Last Listing Agent Jeremy Collins Ridgeline Real Estate

  • /17

    $279,000

    • 5 Beds
    • 3 Baths
    • 1,812 Sq Ft

    2100 Baltimore Rd, Chester, VT 05143

    COUNTRY LIVING ON 4.97 ACRES, JUST 6 MILES TO SPRINGFIELD SHOPPING PLAZA. 9 ROOM HOME OFFERS GROUND FLOOR WITH APPLIANCED KITCHEN W/ DINING AREA, LIVING ROOM, SUNROOM, FULL BATH, FRONT BEDROOM, & ANOTHER BEDROOM W/ FULL BATH. THE SECOND FLOOR HAS 2 BEDROOMS PLUS ANOTHER BEDROOM W/ 3/4 BATH AND WALK-IN CLOSET. SEVCA RECENTLY INSULATED ENTIRE HOUSE AND ADDED A NEW FHA OIL FURNACE IN THE SUMMER OF

    Don Chabot Town and Country Realty

    2100 Baltimore Rd, Chester, VT 05143
  • /36

    $425,000 Sold Jul 30, 2025

    115 Orcutt Dr, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,360 Sq Ft
    • Built 1955

    Last Sold Summary

    • $312/SF
    • 26 Days On Market

    Current Estimated Value $426,092

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    115 Orcutt Dr, Chester, VT 05143
    • /33

      Est $645,150 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

      • 8% Below List Price
      • $318/SF
      • 27 Days On Market
      • Last Sold Price $705,000
      • Oct 20, 2023

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

  • /53

    $1,690,000

    • 5 Beds
    • 5 Baths
    • 5,400 Sq Ft

    1302 Popple Dungeon Rd, Chester, VT 05143

    Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg-style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design.Inside, the home is defined by warm, handcrafted details—wide-plank wood floors, paneled walls,

    Gary Coger Four Seasons Sotheby's Int'l Realty

    1302 Popple Dungeon Rd, Chester, VT 05143
  • /60

    $815,000 Sold Feb 13, 2026

    810 Quarry Rd, Chester, VT 05143

    • 3 Beds
    • 2.5 Baths
    • 2,466 Sq Ft
    • Built 2006

    Last Sold Summary

    • $330/SF
    • 4 Days On Market

    Current Estimated Value $811,612

    Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

    810 Quarry Rd, Chester, VT 05143
    • /19

      Est $207,914 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

      • 7% Above List Price
      • $390/SF
      • 211 Days On Market
      • Last Sold Price $195,000
      • Mar 15, 2024

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /60

    $549,000

    • 2 Beds
    • 2 Baths
    • 2,016 Sq Ft

    35 Upper Bartonsville Rd, Chester, VT 05143

    Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009 and complete with a newer barn, chicken coop, treehouse, and storage shed could be what you have been dreaming of. Conveniently located just a short drive to 91, not far to the Vast trail access for snowmobiling, and near to many Vermont mountains for skiing or snowboarding. The warm and welcoming home

    Erin Kendall EXP Realty

    35 Upper Bartonsville Rd, Chester, VT 05143
  • /2

    $350,000 Sold Nov 09, 2025

    491 Farrar Rd, Chester, VT 05143

    • 4 Beds
    • 3.5 Baths
    • 2,710 Sq Ft
    • Built 1990

    Last Sold Summary

    • 12% Below List Price
    • $129/SF
    • 123 Days On Market

    Current Estimated Value $346,743

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    491 Farrar Rd, Chester, VT 05143
    • /26

      Est $357,608 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

      • 28% Above List Price
      • $215/SF
      • 52 Days On Market
      • Last Sold Price $280,000
      • Dec 15, 2023

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

  • /12

    $120,000

    • Land
    • 3.24 Acres
    • $37,037 per Acre

    508 Mattson Rd, Chester, VT 05143

    This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn—ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded

    Jessica Citera Cummings & Co

    508 Mattson Rd, Chester, VT 05143
  • /2

    $229,000 Sold Aug 29, 2025

    87 Kevadus Cir, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 840 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Above List Price
    • $273/SF
    • 2 Days On Market

    Current Estimated Value $232,375

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    87 Kevadus Cir, Chester, VT 05143

Showing Results 81 - 120, Page 3 of 18

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