Recently Sold Chester, VT Homes

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  /59

  $608,000 Sold Dec 27, 2024

  • 1,728 Sq Ft
  • $352/SF
  • 27 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1986

  50 Howard Rd, Chester, VT 05143

  Discover your private sanctuary in Chester, Vermont! This beautifully upgraded 1986 post-and-beam Saltbox is set on 5 serene, wooded acres, offering 3 bedrooms, 2.5 bathrooms, and a versatile living space. Recent updates, totaling over $100k, include a renovated kitchen with new flooring, countertops, sink, faucet, and backsplash and updated bathrooms on 1st and 2nd floors. A new skylight will be

  Jeremy Collins Ridgeline Real Estate

  50 Howard Rd, Chester, VT 05143
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  /25

  $107,000 Sold Dec 27, 2024

  • Land
  • 8 Acres
  • $13,375 per Acre

  • 206 Days On Market

  0 Brookside Dr Unit 4994316, Chester, VT 05143

  Brookside Dr. Chester. Eight acres high on a hill side, a cross valley view with a little clearing, possible down the valley too. Property is partially wooded, has a small stream and has a field are that will need to be reclaimed for a nice house site. Survey shows a spring. State permit WW-2-2138 for a 5 bedroom too Own your piece of Vermont.

  Mike England Michael England Real Estate

  0 Brookside Dr Unit 4994316, Chester, VT 05143
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  /36

  $925,000 Sold Dec 13, 2024

  • 2,916 Sq Ft
  • $317/SF
  • 169 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1850

  2181 White Rd, Chester, VT 05143

  Nestled along a serene country road, this enchanting home exudes rustic charm and timeless elegance. The “Twin Brooks” that flank the property and private pond round out the much desired water features. Hand hewn beamed ceilings welcome you into a cozy haven where every detail tells a story. Adorned with captivating features, the interior boasts a marble-faced fireplace, a soapstone stove

  Lee Brown Four Seasons Sotheby's Int'l Realty

  2181 White Rd, Chester, VT 05143
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  /31

  $1,900,000 Sold Dec 10, 2024

  • 4,171 Sq Ft
  • $456/SF
  • 38 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1980

  231 Christmas Tree Farm Rd, Chester, VT 05143

  The Cabin is a private retreat on 245 acres with sweeping views of the Green Mountains. Rebuilt in 2024, the home blends modern amenities with the rustic charm of a log cabin. A long drive follows a mountain brook to the cabin. Inside, a bright, airy space features a spacious kitchen flowing into the dining and living area, centered around a stone fireplace and floor-to-ceiling windows. The

  Dia Jenks LandVest, Inc/Woodstock

  231 Christmas Tree Farm Rd, Chester, VT 05143
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  /40

  $635,000 Sold Dec 06, 2024

  • 1,876 Sq Ft
  • $338/SF
  • 89 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2012

  994 Dodge Rd, Chester, VT 05143

  Discover this extraordinary property, available for the first time! Nestled on 26 pristine, private acres at the end of a serene road, this 3-bedroom contemporary home is a true gem. Impeccably maintained by its original owners, every detail of this residence has been thoughtfully designed. The home features a welcoming entryway mudroom, a cozy sitting area leading into the dining space, and a

  Gary Coger Four Seasons Sotheby's Int'l Realty

  994 Dodge Rd, Chester, VT 05143
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  /34

  $1,250,000 Sold Dec 05, 2024

  • 1,918 Sq Ft
  • $652/SF
  • 27 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2004

  209 Ingraham Hill Rd, Chester, VT 05143

  Large acreage and vast views. The cabin on Steadman Hill is a newly finished off-grid home on 477 acres. With breathtaking south-facing views of a large meadow and the Green Mtns, this retreat offers an inspiring setting to write the great American novel, create art, or simply enjoy the peacefulness in nature. The mature woodlands are filled with towering oak, maple and beech trees. The land is

  Dia Jenks LandVest, Inc/Woodstock

  209 Ingraham Hill Rd, Chester, VT 05143
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  /24

  $310,000 Sold Dec 03, 2024

  • 1,293 Sq Ft
  • $240/SF
  • 116 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1988

  1767 Rockingham Rd, Chester, VT 05143

  This beautiful turnkey Log home is the perfect weekend getaway or a convenient and tasteful primary residence. Located less than 30 minutes from both Okemo and Magic Mountain, it offers plenty of opportunities for mountain adventures. Whether you're into skiing, hiking, or simply enjoying the stunning landscapes, you'll find it all within easy reach. The home has recently received numerous

  Thaddeus Abare Barrett and Valley Associates Inc.

  1767 Rockingham Rd, Chester, VT 05143
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  /12

  $19,000 Sold Nov 29, 2024

  • Land
  • 5.51 Acres
  • $3,448 per Acre

  • 183 Days On Market

  0 Remington Rd Unit 12 5001944, Chester, VT 05143

  REUCDUED $18,000.00, PRICED TO SELL! One of the larger lots in the lower Remington subdivision. This private lot has underground power at the lot and the permitted septic is an inground system. Bring your plans and your builder or have the seller build your dream home! PLEASE NOTE THERE IS A MINIMUM OF 1,800 Sq Ft Of Finished Living Space.

  Frank Provance Diamond Realty

  0 Remington Rd Unit 12 5001944, Chester, VT 05143
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  /41

  $410,000 Sold Nov 08, 2024

  • 1,410 Sq Ft
  • $291/SF
  • 44 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1999

  56 Hidden Newton Rd, Chester, VT 05143

  This log home in Windham includes a large yard with fruit trees, room for gardening and recreation, privately situated on a quiet dead-end street. Enjoy the peace and quiet of the natural surroundings with a small pond, apple trees and large deck to relax on. This 3 bedroom , 2 bath home has a nice interior flow with an open kitchen/living/dining floor plan. Enter through the large mudroom and

  Alison Cummings Cummings & Co

  56 Hidden Newton Rd, Chester, VT 05143
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  /40

  $595,000 Sold Nov 08, 2024

  • 2,080 Sq Ft
  • $286/SF
  • 55 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 2004

  2656 Weston-Andover Rd, Chester, VT 05143

  One of a kind! If you wanted to be 100% off the grid, but in a home that looks & functions like a traditional home, then look no further. This is a special home-from the quiet spot on the Ox Bow with long brook frontage to the handsome architecture & interior detail. No other house will ever be visible, your privacy is protected, but you are minutes from Weston, Chester & Ludlow. The floorplan is

  Betty McEnaney Diamond Realty

  2656 Weston-Andover Rd, Chester, VT 05143
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  /18

  $295,000 Sold Nov 01, 2024

  • 1,487 Sq Ft
  • $198/SF
  • 41 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1910

  3264 Trebo Rd, Chester, VT 05143

  Discover the potential of this 1910 farmhouse, nestled on 15 picturesque acres at the corner of Trebo Rd and Crow Hill Rd. 5 of the acres are across the road featuring a large pond big enough for swimming and kayaking, this property offers a canvas for your vision. The Farmhouse is in need of extensive rehab but whether renovating the existing structure or building anew this property is ideal for

  Gary Coger Four Seasons Sotheby's Int'l Realty

  3264 Trebo Rd, Chester, VT 05143
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  /39

  $715,000 Sold Oct 26, 2024

  • 1,735 Sq Ft
  • $412/SF
  • 108 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2021

  276 Old Coach Rd, Chester, VT 05143

  This magnificent newly constructed home has it all! Located in the peaceful Popple Dungeon area of Chester, Vermont, you'll feel a million miles away from the world, nestled within 29 beautifully wooded acres along the South Branch of the Williams River. With just a short walk, you have over 1/4 mile of your very own stream to cool off in. There is no urban glow, little to no traffic, and the

  Daire Gibney Barrett and Valley Associates Inc.

  276 Old Coach Rd, Chester, VT 05143
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  /12

  $124,000 Sold Oct 25, 2024

  • 630 Sq Ft
  • $197/SF
  • 6 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1940

  22 White Rd, Chester, VT 05143

  Priced below town assessment and just in time for hunting season, this cute cottage/camp is being sold "as is." This camp sits on 1.1 acres of land, septic tank installed 10 to 15 years ago. It features living room, kitchen, bedroom and a 3/4 bath on the main floor and a loft in part of the second floor. It also has a shed and an outhouse. Don't miss this opportunity!!!

  Darlene Conca Keller Williams Realty Metro-Keene

  22 White Rd, Chester, VT 05143
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  /37

  $255,000 Sold Oct 18, 2024

  • 960 Sq Ft
  • $266/SF
  • 5 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  468 Vt Route 103 S, Chester, VT 05143

  Come check out this Main St., turn-key charmer, on a level corner lot, in the Village of Chester. A great neighborhood, walking distance to local shops, schools and in town amenities. You'll love the convenience of the attached (via breezeway) one car garage. This home boasts new paint in every room, updated floors, kitchen and bath, with new furnishings and mattresses. The lighting in the

  Frank Provance Diamond Realty

  468 Vt Route 103 S, Chester, VT 05143
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  /38

  $680,000 Sold Oct 17, 2024

  • 1,171 Sq Ft
  • $581/SF
  • 53 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1990

  2253 White Rd, Chester, VT 05143

  Stunning acreage surrounds this charming home in Windham, Vermont.110 acres of curated land with trails throughout. Lots of places to explore and enjoy, all on your own land! A quintessential get-away with a large screened-in porch overlooking the waterfall and pond. Follow the bridge across the pond to the meadow and trails. The extensive trail network is well maintained, meandering throughout

  Alison Cummings Cummings & Co

  2253 White Rd, Chester, VT 05143
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  /16

  $257,000 Sold Oct 11, 2024

  • 1,008 Sq Ft
  • $255/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1983

  192 Kevadus Cir, Chester, VT 05143

  This Ranch-style home is tucked away in the back of the Kevadus Circle neighborhood and is ready for its next owner! The main level features three bedrooms, 1 bathroom with a classic ranch layout giving ample space for both the kitchen and living room. There are two additional bonus rooms that could serve as an office, playroom, or even extra storage both of which include closets and below-grade

  Thaddeus Abare Barrett and Valley Associates Inc.

  192 Kevadus Cir, Chester, VT 05143
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  /4

  $106,000 Sold Oct 07, 2024

  • Land
  • 10.1 Acres
  • $10,495 per Acre

  • 82 Days On Market

  1599 Mattson Rd, Chester, VT 05143

  Experience the tranquility of country living with this stunning 10.1-acre property. Enjoy breathtaking views, a fully functional septic system, and a drilled well. The property features a solid structure and 2.5 acres of maintained land, complete with a chicken coop, an apple tree, and blueberry bushes. Located in a quiet neighborhood, this land offers peace and privacy. Additionally, over 7

  Amy Vashaw Twin State Realty LLC

  1599 Mattson Rd, Chester, VT 05143
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  /29

  $325,000 Sold Oct 04, 2024

  • 1,137 Sq Ft
  • $286/SF
  • 18 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1983

  201 Hill Top Rd, Chester, VT 05143

  Located just outside of Chester is this three bedroom log home that is close to several resorts. Expansive decks and room for your garden on over five acres. Two out buildings and a nearby seasonal stream. Interior has a cathedral ceiling spanning to the second floor bedroom. Living room has a unique pellet stove to help keep you warm during winter. Kronaspan Rocko flooring on the main floor

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  201 Hill Top Rd, Chester, VT 05143
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  /29

  $277,500 Sold Oct 01, 2024

  • 910 Sq Ft
  • $305/SF
  • 57 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1950

  3483 Popple Dungeon Rd, Chester, VT 05143

  This well maintained home is located on a country road in Chester that meanders along a brook. One level living with high ceilings and tasteful upgrades throughout. A wood stove warms the living space in the cooler months. A wood shed and patio area located off the main living area, perfect to enjoy outdoor dining. A heated two car garage with a second floor that would be perfect to finish off

  Jessica Citera Cummings & Co

  3483 Popple Dungeon Rd, Chester, VT 05143
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  /9

  $137,500 Sold Sep 23, 2024

  • Land
  • 12.51 Acres
  • $10,991 per Acre

  • 355 Days On Market

  00 Coach Rd, Chester, VT 05143

  This beautiful 12.51 acre in town lot is one of the last of it's kind! This lot features long range Views, extremely easy access to downtown Chester being only 3 minutes from the Chester green, and a pond that could make this property the perfect Vermont get-away. The owners have subdivided this parcel from their larger parcel and have agreed to allow for a 50 foot wide right-of-way for a

  Thaddeus Abare Barrett and Valley Associates Inc.

  00 Coach Rd, Chester, VT 05143
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  /38

  $750,000 Sold Sep 20, 2024

  • 2,242 Sq Ft
  • $335/SF
  • 67 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1990

  2401 N Hill Rd, Chester, VT 05143

  With an excellent layout, special features and prime location, this four bedroom, two and a half bath cape in Andover is a must see! It sits on 4+ acres of manicured grounds with a babbling brook running through the property. Situated between quintessential Weston and the action of Ludlow, it is easy to access, a peaceful setting surrounded by a natural Vermont landscape. The area is host to

  Alison Cummings Cummings & Co

  2401 N Hill Rd, Chester, VT 05143
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  /2

  $792,000 Sold Jul 15, 2025

  • 3,614 Sq Ft
  • $219/SF
  • 0 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2012

  1295 Middletown Rd, Chester, VT 05143

  Discover this beautifully maintained 3-bedroom, 31⁄2-bath home on over 3 acres along a quiet country road—just minutes from the village of Weston. Inside, an open-concept layout brings together a bright kitchen, dining, and living area, while the walk-out lower level adds flexible room for a family area or recreation. Spacious entry/mudroom and an attached 2-car garage, this home balances

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  1295 Middletown Rd, Chester, VT 05143
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  /2

  $285,000 Sold Mar 26, 2025

  • 1,824 Sq Ft
  • $156/SF
  • 87 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1852

  17 Grafton St, Chester, VT 05143

  Discover this beautifully maintained 1852 Colonial home situated on a prime corner lot in the heart of downtown Chester. Currently configured as a two-unit apartment, this property features a spacious two-bedroom, one-bath unit on the upper level and a cozy one-bedroom, one-bath unit on the first floor. With its versatile layout, you can easily convert it back to a single-family residence or live

  Gary Coger Four Seasons Sotheby's Int'l Realty

  17 Grafton St, Chester, VT 05143

Showing Results 41 - 63, Page 2 of 2