3,392

Homes in ZIP Code 05143

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  • 397 River St, Chester, VT 05143
    397 River St, Chester, VT 05143
    397 River St, Chester, VT 05143
    /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
  • 96 S Main St, Chester, VT 05143
    96 S Main St, Chester, VT 05143
    96 S Main 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
  • 1979 N Hill Rd, Chester, VT 05143
    1979 N Hill Rd, Chester, VT 05143
    1979 N Hill Rd, 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
    • 87 Trombley Rd, Andover, VT 05143
      87 Trombley Rd, Andover, VT 05143
      87 Trombley Rd, Andover, VT 05143
      /59

      Not Listed For Sale

      87 Trombley Rd, Andover, VT 05143

      • 2 Beds
      • 1 Bath
      • 1,134 Sq Ft
      • Built 1983
      87 Trombley Rd, Andover, VT 05143

      Last Sold Summary

      • 473 Days On Market

  • 1144 Potash Brook Rd, Chester, VT 05143
    1144 Potash Brook Rd, Chester, VT 05143
    1144 Potash Brook Rd, Chester, VT 05143
    /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
  • 34 School St Unit A, Chester, VT 05143
    34 School St Unit A, 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
  • 472 Main St, Chester, VT 05143
    472 Main St, Chester, VT 05143
    472 Main St, 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
    • Lot 6 Jillie Ln, Chester, VT 05143
      Lot 6 Jillie Ln, Chester, VT 05143
      Lot 6 Jillie Ln, 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

  • 40 Fenton Rd, Chester, VT 05143
    40 Fenton Rd, Chester, VT 05143
    40 Fenton Rd, Chester, VT 05143
    /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
  • 32 S Main St Unit 7, Chester, VT 05143
    32 S Main St Unit 7, Chester, VT 05143
    32 S Main St Unit 7, 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
  • 45 Dalrymple St, Chester, VT 05143
    45 Dalrymple St, Chester, VT 05143
    45 Dalrymple St, 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
    • 1599 Mattson Rd, Chester, VT 05143
      1599 Mattson Rd, Chester, VT 05143
      1599 Mattson Rd, 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

  • 64 Maple St, Chester, VT 05143
    64 Maple St, Chester, VT 05143
    64 Maple St, Chester, VT 05143
    /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
  • 735 Main St, Chester, VT 05143
    735 Main St, Chester, VT 05143
    735 Main 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
  • 2510 E Hill Rd, Chester, VT 05143
    2510 E Hill Rd, Chester, VT 05143
    2510 E 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 $591,115

    Last Listing Agent Betty McEnaney Diamond Realty

    2510 E Hill Rd, Chester, VT 05143
    • 1751 Rockingham Rd, Rockingham, VT 05143
      1751 Rockingham Rd, Rockingham, VT 05143
      1751 Rockingham Rd, Rockingham, VT 05143
      /24

      Est $229,848

      Not Listed For Sale

      1751 Rockingham Rd, Rockingham, VT 05143

      • 2 Beds
      • 1.5 Baths
      • 1,120 Sq Ft
      • Built 1989
      1751 Rockingham Rd, Rockingham, VT 05143

      Last Sold Summary

      • 14 Days On Market

  • 81 Main St, Chester, VT 05143
    81 Main St, Chester, VT 05143
    81 Main St, Chester, VT 05143
    /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
  • 240 Piper Hill Rd, Weston, VT 05161
    240 Piper Hill Rd, Weston, VT 05161
    240 Piper Hill Rd, Weston, VT 05161
    /60

    $2,950,000

    Sold Dec 22, 2025

    240 Piper Hill Rd, Weston, VT 05161

    • 5 Beds
    • 6.5 Baths
    • 8,056 Sq Ft
    • Built 1990

    Last Sold Summary

    • $366/SF
    • 28 Days On Market

    Last Listing Agent Steve Stettler Four Seasons Sotheby's Int'l Realty

    240 Piper Hill Rd, Weston, VT 05161
    • 3089 Vt Route 11 W, Chester, VT 05143
      3089 Vt Route 11 W, Chester, VT 05143
      3089 Vt Route 11 W, 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

  • Markham Mountain, Andover, VT 05143
    Markham Mountain, Andover, VT 05143
    Markham Mountain, Andover, VT 05143
    /16

    $3,150,000

    • Land
    • 506 Acres
    • $6,225 per Acre

    Markham Mountain, Andover, VT 05143

    Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence.This land's historical roots run deep, originally belonging to the Marsh

    Story Jenks LANDVEST

    Markham Mountain, Andover, VT 05143
  • 938 Stigers Rd, Chester, VT 05143
    938 Stigers Rd, Chester, VT 05143
    938 Stigers 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 $1,246,867

    Last Listing Agent Liz Moore Real Broker LLC

    938 Stigers Rd, Chester, VT 05143
    • 35 Depot St, Chester, VT 05143
      35 Depot St, Chester, VT 05143
      35 Depot St, 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

  • 76 Goldthwaite Rd, Chester, VT 05143
    76 Goldthwaite Rd, Chester, VT 05143
    76 Goldthwaite Rd, Chester, VT 05143
    /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
  • 656 Main St, Chester, VT 05143
    656 Main St, Chester, VT 05143
    656 Main St, 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
    • 5 Town Farm Rd, Town of Rockingham, VT 05101
      5 Town Farm Rd, Town of Rockingham, VT 05101
      /2

      Not Listed For Sale

      5 Town Farm Rd, Town of Rockingham, VT 05101

      • 1 Bed
      • 1 Bath
      5 Town Farm Rd, Town of Rockingham, VT 05101

  • 377 Coach Rd, Chester, VT 05143
    377 Coach Rd, Chester, VT 05143
    377 Coach Rd, Chester, VT 05143
    /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
  • 442 Vermont 103, Chester, VT 05143
    442 Vermont 103, Chester, VT 05143
    442 Vermont 103, 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
    • 00 Trebo Rd, Chester, VT 05143
      00 Trebo Rd, Chester, VT 05143
      00 Trebo 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

  • 29 Markham Ln, Weston, VT 05161
    29 Markham Ln, Weston, VT 05161
    29 Markham Ln, Weston, VT 05161
    /36

    $299,000

    • 2 Beds
    • 1 Bath
    • 750 Sq Ft

    29 Markham Ln, Weston, VT 05161

    This delightful 2-bedroom, 1-bath cottage located in the heart of the picturesque village of Weston is waiting for a new owner that is looking for a sweet little Vermont retreat. Built in 1947, this home offers timeless character with cozy living spaces and classic Vermont charm. Perfectly situated within walking distance to the Weston Playhouse, the iconic Vermont Country Store, and locally

    Catherine Cairns Maple Leaf Real Estate

    29 Markham Ln, Weston, VT 05161
  • 1374 Vt Route 103 N, Chester, VT 05143
    1374 Vt Route 103 N, Chester, VT 05143
    1374 Vt Route 103 N, 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
    • 3264 Trebo Rd, Chester, VT 05143
      3264 Trebo Rd, Chester, VT 05143
      3264 Trebo Rd, 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

  • 00 Simonsville Rd, Andover, VT 05143
    00 Simonsville Rd, Andover, VT 05143
    00 Simonsville Rd, Andover, VT 05143
    /20

    $85,000

    • Land
    • 3.99 Acres
    • $21,303 per Acre

    00 Simonsville Rd, Andover, VT 05143

    ANDOVER 3.99 Acres on the Williams River that was once a part of the Historic Jaquith Homestead. Walk the old mowing road that winds through the property, leading to three meadow areas along the river. The central meadow has a designated home site for a 4 bedroom state approved septic. The owners have just had the house location resighted to make sure it is out of the flood zone. A great spot for

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    00 Simonsville Rd, Andover, VT 05143
  • 373 Brookline Rd, Athens, VT 05143
    373 Brookline Rd, Athens, VT 05143
    /2

    $250,000

    Sold Jul 25, 2025

    373 Brookline Rd, Athens, VT 05143

    • 3 Beds
    • 1 Bath
    • 900 Sq Ft
    • Built 1971

    Last Sold Summary

    • 9% Above List Price
    • $278/SF
    • 9 Days On Market

    Current Estimated Value $247,508

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    373 Brookline Rd, Athens, VT 05143
    • 00 Vt Route 11 W, Chester, VT 05143
      00 Vt Route 11 W, Chester, VT 05143
      00 Vt Route 11 W, 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

  • 0 Linden Way Unit 5093908, Chester, VT 05143
    0 Linden Way Unit 5093908, Chester, VT 05143
    0 Linden Way Unit 5093908, Chester, VT 05143
    /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
  • 00 Hillcrest Dr, Andover, VT 05143
    00 Hillcrest Dr, Andover, VT 05143
    00 Hillcrest Dr, Andover, VT 05143
    /15

    $70,000

    Sold May 14, 2026

    00 Hillcrest Dr, Andover, VT 05143

    • Land
    • 4.05 Acres
    • $17,284 per Acre

    Last Sold Summary

    • 26% Below List Price
    • 274 Days On Market

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    00 Hillcrest Dr, Andover, VT 05143
    • 1709 Potash Brook Rd, Chester, VT 05143
      1709 Potash Brook Rd, Chester, VT 05143
      1709 Potash Brook Rd, 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

  • 00 Marsh Cross Rd, Andover, VT 05143
    00 Marsh Cross Rd, Andover, VT 05143
    00 Marsh Cross Rd, Andover, VT 05143
    /16

    $3,150,000

    • Land
    • 506 Acres
    • $6,225 per Acre

    00 Marsh Cross Rd, Andover, VT 05143

    Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence. This land's historical roots run deep, originally belonging to the Marsh

    Story Jenks LandVest, Inc/Woodstock

    00 Marsh Cross Rd, Andover, VT 05143
  • 1923 N Hill Rd, Chester, VT 05143
    1923 N Hill Rd, Chester, VT 05143
    1923 N Hill 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
    • 201 Hill Top Rd, Chester, VT 05143
      201 Hill Top Rd, Chester, VT 05143
      201 Hill Top 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

Showing Results 1 - 40, Page 1 of 18

Vermont Windsor County Chester 05143

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