2,722

Chester, VT Homes

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  • /29

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    447 Elm St, Chester, VT 05143

    $5000 buyer credit offered with accepted offer by 3/15/26!!!Welcome to your dream home – This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood

    Agent Photo

    Lisa Kelley

    Cummings & Co

    (802) 200-2452

    447 Elm St, Chester, VT 05143
  • /6

    $1,100 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Apartment for Rent

    32 S Main St Unit 4, Chester, VT 05143

    Traditional one bedroom apartment on Main Street in Chester. Walking distance to amenities. Coin-op laundry on site.$1,100.00 per month with heat included. No pets.References and credit check required.

    Team BVA Rentals Barrett and Valley Associates Inc.

    32 S Main St Unit 4, Chester, VT 05143
  • /2

    $30,000 Sold Jun 04, 2025

    206 Cummings Rd, Chester, VT 05143

    • Land
    • 0.5 Acre
    • $60,000 per Acre

    Last Sold Summary

    • 43% Below List Price
    • 208 Days On Market

    Current Estimated Value $34,223

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    206 Cummings Rd, Chester, VT 05143
    • /10

      Not Listed For Sale

      Lot 6 Jillie Ln, Chester, VT 05143

      Lot 6 Jillie Ln, Chester, VT 05143

      Last Sold Summary

      • 1,909 Days On Market

      Last Sold Price $50,000

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

  • /46

    $399,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 2,751 Sq Ft

    3466 Vt Route 103 N, Chester, VT 05143

    Set on .76 acres in the peaceful Chester VT countryside, this former schoolhouse offers timeless farmhouse charm, rich history, and a setting that feels both private and inviting. Framed by classic stone walls, a pond site, and a gently wooded backdrop, the home sits just off a main road, providing easy access to town while maintaining a quiet, pastoral atmosphere. Originally serving the

    Betsy Adamovich Real Broker LLC

    3466 Vt Route 103 N, Chester, VT 05143
  • /60

    $475,000 Sold Aug 27, 2025

    472 Main St, Chester, VT 05143

    • 5 Beds
    • 7 Baths
    • 5,546 Sq Ft
    • Built 1850

    Last Sold Summary

    • 5% Below List Price
    • $86/SF
    • 36 Days On Market

    Current Estimated Value $483,259

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    472 Main St, Chester, VT 05143
    • /4

      Not Listed For Sale

      1599 Mattson Rd, Chester, VT 05143

      1599 Mattson Rd, Chester, VT 05143

      Last Sold Summary

      • 82 Days On Market

      Last Sold Price $106,000

      Last Listing Agent Amy Vashaw Twin State Realty LLC

  • /57

    $599,000 Under Contract

    • 7 Beds
    • 3.5 Baths
    • 3,850 Sq Ft

    534 Elm St, Chester, VT 05143

    Have you been waiting to buy just the right property? An impressive home in a special town in an amazing state might be perfect. This well-loved Victorian has 4 bedrooms in the main house and another 3 bedrooms in the carriage house unit. There is a storage room in between the two spaces with doors to open to easily connect the units. The beautiful main house has a farmhouse-style kitchen, formal

    Tyleen Murray Kelley Real Estate, Inc.

    534 Elm St, Chester, VT 05143
  • /2

    $350,000 Sold Jun 25, 2025

    198 Coach Rd, Chester, VT 05143

    • 4 Beds
    • 2.5 Baths
    • 2,904 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Above List Price
    • $121/SF
    • 82 Days On Market

    Current Estimated Value $353,359

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    198 Coach Rd, Chester, VT 05143
    • /38

      Est $277,477 Not Listed For Sale

      3089 Vt Route 11 W, Chester, VT 05143

      • 4 Beds
      • 2 Baths
      • 1,732 Sq Ft
      • Built 1857
      3089 Vt Route 11 W, Chester, VT 05143

      Last Sold Summary

      • 75% Above List Price
      • $92/SF
      • 55 Days On Market

      Last Sold Price $159,000

      Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  • /60

    $649,000

    • 3 Beds
    • 2 Baths
    • 2,205 Sq Ft

    688 Hidden Heights Rd, Chester, VT 05143

    Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of the

    Joseph Karl William Raveis Real Estate Vermont Properties

    688 Hidden Heights Rd, Chester, VT 05143
  • /43

    $400,000 Sold Apr 25, 2025

    3057 Vt Route 11 E, Chester, VT 05143

    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft
    • Built 1984

    Last Sold Summary

    • 10% Below List Price
    • $222/SF
    • 106 Days On Market

    Current Estimated Value $431,780

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    3057 Vt Route 11 E, Chester, VT 05143
    • /17

      Est $85,234 Not Listed For Sale

      35 Depot St, Chester, VT 05143

      • 4 Beds
      • Built 1880
      35 Depot St, Chester, VT 05143

      Last Sold Summary

      • 14% Above List Price
      • $13/SF
      • 68 Days On Market

      Last Sold Price $75,000

      Last Listing Agent Debra Staniscia 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
  • /52

    $598,000 Sold Oct 10, 2025

    2510 E Hill Rd, Chester, VT 05143

    • 3 Beds
    • 2.5 Baths
    • 2,264 Sq Ft
    • Built 1978

    Last Sold Summary

    • 5% Below List Price
    • $264/SF
    • 94 Days On Market

    Current Estimated Value $588,806

    Last Listing Agent Betty McEnaney Diamond Realty

    2510 E Hill Rd, Chester, VT 05143
    • /36

      Not Listed For Sale

      141 Stage, Chester, VT 05143

      • 2 Beds
      • 1 Bath
      • 924 Sq Ft
      • Built 1996
      141 Stage, Chester, VT 05143

      Last Sold Summary

      • $920/SF
      • 17 Days On Market

      Last Sold Price $850,000

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /37

    $529,000

    • 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
  • /60

    $400,000 Sold May 19, 2025

    196 North St, Chester, VT 05143

    • 3 Beds
    • 3 Baths
    • 2,960 Sq Ft
    • Built 1844

    Last Sold Summary

    • 6% Below List Price
    • $135/SF
    • 166 Days On Market

    Current Estimated Value $419,335

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    196 North St, Chester, VT 05143
    • /5

      Not Listed For Sale

      00 Trebo Rd, Chester, VT 05143

      00 Trebo Rd, Chester, VT 05143

      Last Sold Summary

      • 349 Days On Market

      Last Sold Price $100,000

      Last Listing Agent Brian Gehlich RE/MAX

  • /60

    $589,000

    • 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
  • /36

    $1,400,000 Sold Aug 27, 2025

    938 Stigers Rd, Chester, VT 05143

    • 3 Beds
    • 3.5 Baths
    • 2,614 Sq Ft
    • Built 2011

    Last Sold Summary

    • 15% Below List Price
    • $536/SF
    • 42 Days On Market

    Current Estimated Value $1,468,702

    Last Listing Agent Liz Moore Real Broker LLC

    938 Stigers Rd, Chester, VT 05143
    • /18

      Est $315,835 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

      • 7% Above List Price
      • $198/SF
      • 41 Days On Market

      Last Sold Price $295,000

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

  • /20

    $449,000

    • 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
  • /55

    $605,000 Sold Oct 02, 2025

    656 Main St, Chester, VT 05143

    • 3 Beds
    • 2.5 Baths
    • 3,040 Sq Ft
    • Built 1904

    Last Sold Summary

    • 7% Below List Price
    • $199/SF
    • 47 Days On Market

    Current Estimated Value $599,499

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    656 Main St, 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

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

  • /52

    $625,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 2,794 Sq Ft

    95 Church St, Chester, VT 05143

    Charming Renovated Farmhouse in the Heart of Chester This beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway. Inside, enjoy a spacious kitchen with custom pantry shelving, a

    McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    95 Church St, Chester, VT 05143
  • /60

    $220,000 Sold Nov 07, 2025

    442 Vermont 103, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft
    • Built 1941

    Last Sold Summary

    • 8% Below List Price
    • $215/SF
    • 70 Days On Market

    Current Estimated Value $232,676

    Last Listing Agent Rachael Rogala Lange & Lange

    442 Vermont 103, Chester, VT 05143
    • /4

      Est $557,497 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

      • 14% Above List Price
      • $182/SF
      • 137 Days On Market

      Last Sold Price $490,000

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /42

    $429,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    1979 N Hill Rd, Chester, VT 05143

    Welcome to this attractive Andover Contemporary home, perfectly suited for year-round living or as a Vermont vacation retreat. Built in 2005, this 3 bedroom, 2 bath residence offers modern comfort in a peaceful country setting on 2.1 acres while being just minutes from Okemo Mountain Resort and close to scenic snowmobile trails—ideal for outdoor enthusiasts in every season. The inviting

    Geralyn Donohue Engel & Völkers Okemo

    1979 N Hill Rd, Chester, VT 05143
  • /21

    $227,000 Sold Jan 30, 2026

    1374 Vt Route 103 N, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,222 Sq Ft
    • Built 1949

    Last Sold Summary

    • 5% Below List Price
    • $186/SF
    • 20 Days On Market

    Current Estimated Value $234,843

    Last Listing Agent Lisa Kelley Cummings & Co

    1374 Vt Route 103 N, Chester, VT 05143
    • /29

      Est $333,587 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

      • 3% Above List Price
      • $286/SF
      • 18 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  • /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
  • /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
    • /39

      Est $340,471 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

      • 4% Below List Price
      • $170/SF
      • 19 Days On Market

      Last Sold Price $355,000

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

  • /36

    $369,000

    • 5 Beds
    • 1 Bath
    • 2,243 Sq Ft

    2029 N Hill Rd, Chester, VT 05143

    Come, enjoy the quiet charm of Andover in this inviting, private Vermont home—perfect for year-round living or a peaceful getaway. Nestled among evergreens with beautiful snowy views, this property offers easy access to Okemo Mountain, and is also close to Stratton, Magic, and Bromley for skiing, riding, and four-season adventure. Snowmobile enthusiasts will love the nearby VAST trails, and the

    Daire Gibney Barrett and Valley Associates Inc.

    2029 N Hill 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 $241,677

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    154 Reed Rd, Chester, VT 05143
    • /14

      Est $273,018 Not Listed For Sale

      184 Kevadus Cir, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1988
      184 Kevadus Cir, Chester, VT 05143

      Last Sold Summary

      • 21% Above List Price
      • $223/SF
      • 9 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /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
  • /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 $281,959

    Last Listing Agent Jim Bialowski BHG Masiello Keene

    230 Kevadus Cir, Chester, VT 05143
    • /16

      Est $266,227 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

      • 4% Above List Price
      • $255/SF
      • 6 Days On Market

      Last Sold Price $257,000

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

Showing Results 1 - 40, Page 1 of 18

Home Trends in Chester, VT

Housing Trends

Median Sale Price
$400,000
Median Single Family Sale Price
$389,500
Median Townhouse Sale Price
$598,000
Average Price Per Sq Ft
$271
Number of Homes for Sale
13
Last 12 months Home Sales
56
Months of Supply
2.80
Median List Price
$448,888
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
4%
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