2,744

Chester, VT Homes

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  • /41

    $325,000

    $24K PRICE DROP Under Contract
    • 4 Beds
    • 3 Baths
    • 3,332 Sq Ft

    397 River St, Chester, VT 05143

    Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting on the front porch and listening the soft rustle of the willow tree leaves and the babbling brook trickling by, then you step inside and feel that you have walked into a home that was truly loved. The large kitchen offers nice upgrades including tile floor, granite countertops

    Agent Photo

    Lisa Kelley

    Cummings & Co

    397 River St, Chester, VT 05143
  • /17

    $3,200

    Total Monthly Price

    • 4 Beds
    • 2.5 Baths
    • 2,220 Sq Ft
    • House for Rent

    96 S Main St, Chester, VT 05143

    Spacious 4-Bedroom Home with Large Backyard in the Heart of Chester, VT.Welcome to 96 S Main St — a charming and well-appointed 4-bedroom, 2.5-bath home offering 2,215 square feet of comfortable living space in the very heart of Chester village.Inside, you’ll find a bright and generous living room and dining room perfect for relaxing or entertaining, a functional kitchen with all

    96 S Main St, Chester, VT 05143
  • /42

    $415,000

    Sold Mar 30, 2026

    1979 N Hill Rd, Chester, VT 05143

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • Built 2005

    Last Sold Summary

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

    Current Estimated Value $396,718

    Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    1979 N Hill 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

  • /17

    $75,000

    • 2 Beds
    • 1 Bath
    • 620 Sq Ft

    1144 Potash Brook Rd, Chester, VT 05143

    Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

    Agent Photo

    Julie Buffum

    Buffum Realty

    1144 Potash Brook Rd, Chester, VT 05143
  • /2

    $1,200

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    34 School St Unit A, Chester, VT 05143

    Lovely 1 bedroom apartment available for rent on the Green in Chester Vermont. Apartment has a large living room, kitchen, full bathroom and 1 bedroom. 12 month lease required. First, last and 1 month security deposit. Tenant pays utilities. Owner pays for water, sewer and hot water.

    34 School St Unit A, 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 $473,496

    Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    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

  • /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

    Agent Photo

    John Napier

    TPW Real Estate

    40 Fenton Rd, Chester, VT 05143
  • /8

    $1,400 Per Month

    • 2 Beds
    • 1 Bath
    • 750 Sq Ft
    • Apartment for Rent

    32 S Main St Unit 7, Chester, VT 05143

    Traditional two bedroom apartment on Main Street in Chester. Walking distance to amenities. Coin-op laundry on site.$1,400.00 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 7, Chester, VT 05143
  • /34

    $269,000

    Sold Jun 15, 2026

    45 Dalrymple St, Chester, VT 05143

    • 3 Beds
    • 1 Bath
    • 1,168 Sq Ft
    • Built 1986

    Last Sold Summary

    • $230/SF
    • 6 Days On Market

    Current Estimated Value $265,992

    Last Listing Agent Julie Buffum Buffum Realty

    45 Dalrymple St, Chester, VT 05143
    • /38

      Est $238,447

      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

      • 55 Days On Market

  • /60

    $479,000

    • 3 Beds
    • 3 Baths
    • 2,676 Sq Ft

    64 Maple St, Chester, VT 05143

    Located in the village of Chester, this 3-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You’ll enter through the heated attached two-car garage into a layout that’s both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area

    Betsy Adamovich Real Broker LLC

    64 Maple St, Chester, VT 05143
  • /11

    $3,300 Per Month

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft
    • House for Rent

    735 Main St, Chester, VT 05143

    SUMMER SEASON RENTAL!! ...Lovely antique home within walking distance of Chester Village. Fully furnished, clean & comfortable. A great place to relax and enjoy all of what VT has to offer. All utilities except rubbish removal are paid by the owner. $3,300.00 per month plus deposit. Available for the 2026 summer season, June 1 - September 30. References and credit check required.

    Team BVA Rentals Barrett and Valley Associates Inc.

    735 Main St, 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 $591,115

    Last Listing Agent Betty McEnaney Diamond Realty

    2510 E Hill Rd, Chester, VT 05143
    • /17

      Est $83,511

      Not Listed For Sale

      35 Depot St, Chester, VT 05143

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

      Last Sold Summary

      • 68 Days On Market

  • /58

    $475,000

    • 5 Beds
    • 4 Baths
    • 3,865 Sq Ft

    81 Main St, Chester, VT 05143

    Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning

    Betsy Adamovich Real Broker LLC

    81 Main St, 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 $1,246,867

    Last Listing Agent Liz Moore Real Broker LLC

    938 Stigers Rd, 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

  • /39

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 3,308 Sq Ft

    76 Goldthwaite Rd, Chester, VT 05143

    Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal-style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

    Gary Coger Four Seasons Sotheby's Int'l Realty

    76 Goldthwaite 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 $596,275

    Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    656 Main St, Chester, VT 05143
    • /18

      Est $314,286

      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

      • 41 Days On Market

  • /3

    $175,000

    • Land
    • 12.51 Acres
    • $13,989 per Acre

    377 Coach Rd, Chester, VT 05143

    Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home.Located in an area identified for development, it offers both a wonderful building site and long-term

    Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    377 Coach Rd, 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 $228,101

    Last Listing Agent Rachael Lange Lange & Lange

    442 Vermont 103, 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

  • /22

    $85,000

    • Land
    • 5 Acres
    • $17,000 per Acre

    0 Linden Way Unit 5093908, Chester, VT 05143

    Privacy doesn't have to mean isolation!!Wooded acreage, village convenience, and modern connectivity are rarely found in the same package. This newly approved 5 acre parcel in Chester, Vermont offers a private setting surrounded by mature forest while remaining just minutes from the historic village center. Accessed via a private right-of-way, the property provides a peaceful location for a

    Daire Gibney Barrett and Valley Associates Inc.

    0 Linden Way Unit 5093908, 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 $232,848

    Last Listing Agent Lisa Kelley Cummings & Co

    1374 Vt Route 103 N, Chester, VT 05143
    • /4

      Est $568,393

      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

      • 137 Days On Market

  • /44

    $849,000

    • 5 Beds
    • 3 Baths
    • 4,388 Sq Ft

    223 Coach Rd, Chester, VT 05143

    Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to

    Daire Gibney Barrett and Valley Associates Inc.

    223 Coach 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
    • /29

      Est $338,798

      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

      • 18 Days On Market

  • /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
  • /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 $248,331

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    154 Reed Rd, Chester, VT 05143
    • /39

      Est $356,057

      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

      • 19 Days On Market

  • /51

    $390,000

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft

    663 Depot St, Chester, VT 05143

    Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that’s hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates.

    Betsy Adamovich Real Broker LLC

    663 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 $278,909

    Last Listing Agent Jim Bialowski BHG Masiello Keene

    230 Kevadus Cir, Chester, VT 05143
    • /16

      Est $269,674

      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

      • 6 Days On Market

  • /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
  • /2

    $230,000

    Sold Nov 07, 2025

    2739 Route 11, Chester, VT 05143

    • 1 Bed
    • 1 Bath
    • 1,424 Sq Ft
    • Built 1987

    Last Sold Summary

    • 23% Below List Price
    • $162/SF
    • 13 Days On Market

    Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

    2739 Route 11, Chester, VT 05143
    • /37

      Est $253,286

      Not Listed For Sale

      468 Vt Route 103 S, Chester, VT 05143

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1940
      468 Vt Route 103 S, Chester, VT 05143

      Last Sold Summary

      • 5 Days On Market

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$389,000
Median Single Family Sale Price
$384,000
Median Townhouse Sale Price
$677,000
Median 2 Bedroom Sale Price
$309,500
Median 1 Bedroom Sale Price
$210,000
Average Price Per Sq Ft
$268
Number of Homes for Sale
21
Last 12 months Home Sales
57
Months of Supply
4.40
Median List Price
$449,500
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-3%
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