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Chester Vermont Real Estate

Windsor County
Chartered: February 22, 1754
Area: 35,773 Acres = 55.9 Square Miles
Population (US Census, 2000): 3,044
Population Density (persons per square mile): 54.5

Schools

Windsor Southwest Supervisory Union 802-875-3365
Chester-Andover School 802-875-2108
Green Mountain Union High School 802-875-2146

Chester Vermont is a short drive from Springfield Vermont and Bellows Falls Village Vermont. A picturesque downtown with family-owned shops, restaurants, and bread and breakfasts beckons residents for an afternoon stroll along Main Street or a picnic in the town green. An annual fall craft show and a late winter chili contest are just a taste of the goings-on in this quaint Vermont town. Chester Vermont real estate and properties puts Vermont skiing less than an hour away, like Okemo Mountain Resort, Ascutney Mountain Resort, Pico Ski Resort, Killington Resort, Magic Mountain Ski Resort, Stratton Mountain Ski Resort, Suicide Six Ski Area, and Bromley Mountain Ski Resort.

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3590 Vt 103 North Chester VT 05143

Chester, VT3590 Vt 103 North

Price$399,000

Est. Mortgage: $/month

MLS Number 4994539

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

“Fully furnished! This home on .89 acres is located in the beautiful area of Gassetts in Chester, Vermont. Zoning is versatile and provides a wide range of options for commercial, retail, residential, or industrial use. Recent upgrades to the home include a brand new roof, siding, all new flooring, new kitchen cabinets and quarts countertops, new sheetrock and paint in the majority of the house, new sub flooring in the living room, laundry area, and mudroom, new window sills, new mini split, removal of all previous knob and tube wiring, replaced windows, new french door in the living room, new patio and fire pit area, freshly leveled and graveled driveway, two-car carport, refinished front deck, and freshly leveled backyard. This three bedroom, two bathroom home has an open concept as well as a traditional rustic ambiance with a beautiful modern touch. The three bedrooms are located on the second floor, with one bathroom being on the first floor as well as the second. The home is a mere 5 minute drive to the down center or about 8 miles to Okemo Ski Resort in the other direction. Hiking, mountain biking, and snowmobiling trails surround the town, making this home ideal for anyone who enjoys the natural beauty of Vermont. High speed internet is available (currently VTEL). LET'S MAKE A DEAL on LOT MLS# 4994538

Listed by Kimberly Matson and Jessica Samples of BHG Masiello Keene

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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117 South Main Street Chester VT 05143

Chester, VT117 South Main Street

Price$375,000

Est. Mortgage: $/month

MLS Number 4996225

  • Multifamily
  • Units 3
  • Bathroom 3
  • Acreage 0.75
  • Square Feet 2,008

Opportunity awaits! This three-unit property has been very well maintained with 2 long term tenants and 1 Vacant unit that has just been painted and is ready to be owner occupied or rented out. This investment features an in-town location within walking distance to shopping, restaurants and local conveniences. This property also includes additional unfinished square footage in the barn, currently used as 2 rented storage units with great potential for new ideas. Even the basement is impressive as it has all been gone through. The outside of this home was just painted last year. All units are in good shape and fully applianced. This property also has a large in town open lot.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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784 Route 103 N Chester VT 05143

Chester, VT784 Route 103 N

Price$350,000

Est. Mortgage: $/month

MLS Number 5013994

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Nestled on a hill above Route 103 and the Williams River, this charming 3 bedroom, two bathroom ranch makes for a perfect home. The house has had many recent upgrades - two renovated bathrooms, new custom wallpaper, new flooring and a fresh exterior paint job. The basement has been cleaned and painted - it's a blank canvas for the next owner - game room? movie room? or perhaps workshop... The yard is large enough for games and there are plenty of woods to explore or even potential subdivision. The driveway has been freshly graded and there is a carport to keep your car clean from snow. Location is perfect - 3 minutes to Smitty's market, downtown Chester or under 15 minutes to Okemo Mountain Resort. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Listed by Katherine Burns and Joseph Karl of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3483 Popple Dungeon Road Chester VT 05143

Chester, VT3483 Popple Dungeon Road

Price$285,000

Est. Mortgage: $/month

Pending

MLS Number 5003042

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 910

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 for additional living space. A Tesla wall is rented so that the home stays functional during power outages. Beautiful stone walls and garden beds surround the exterior. A wood shed and patio area located off the main living area, perfect to enjoy outdoor dining.

Listed by Jessica Citera of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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110 Shady Grove Lane Chester VT 05143

Chester, VT110 Shady Grove Lane

Price$250,000

Est. Mortgage: $/month

MLS Number 5007717

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2

Located on private road on Shady Grove Lane, this newly constructed 2.5 story 2 bedroom, 2 bath home on 5.12 +/- acres has been framed. The first floor layout includes a large kitchen/living area with a bedroom and full bath. The second floor includes a full bath with large bedroom. This beautiful home includes a walkout basement. All building materials on site are included with the sale. This is a great location 3 miles to downtown Chester and short drives to Magic Mountain, Bromley Mountain, Okemo Mountain, Mount Snow and Stratton Mountain.

Listed by Rob Weltz of Brattleboro Area Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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00 Quarry Road Chester VT 05143

Chester, VT00 Quarry Road

Price$229,000

Est. Mortgage: $/month

MLS Number 4982433

  • Land
  • Acreage 27.8
  • Utilities None
  • PricePerSqFt 8237.41
  • Zoning R40

Explore this 27.8 acre+/- hillside parcel with mountain views and an approved VT state permit for a 4 bedroom family residence, close to the Village of Chester and adjoining Chester Town land. An easily accessed preliminary site has already been cleared. At the top of the ridge, a nice cleared plateau would be a fabulous spot for an off-the-grid bonus cabin retreat with amazing views! This parcel would qualify for the VT Current Use Program for timber management and tax savings. 1 acre (R-40) zoning and 1478' of frontage along Quarry Road makes further subdivision a possibility. Enjoy the year-round recreation the area offers. Close to Grafton for x-country skiing and mountain biking. Convenient to Magic, Okemo, Stratton and Bromley Mountains for downhill enthusiasts. Convenient to I-91, 3 hours to Boston and 4.5 hours to NYC.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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515 Main Street Chester VT 05143

Chester, VT515 Main Street

Price$169,000

Est. Mortgage: $/month

Pending

MLS Number 5007779

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Looking to live near the Chester Green? This may be the home for you! Currently used as a four-unit apartment building I believe that the highest and best use would be to return it to a single-family home with one accessory apartment in the back. The house is in need of renovation however, the style and location would lend well to that investment, or renovate the four units as your next venture, either way you will have a fine home near the center of all that Chester has to offer!

Listed by Susan LeCours of Barrett & Valley Assoc. Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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515 Main Street Chester VT 05143

Chester, VT515 Main Street

Price$169,000

Est. Mortgage: $/month

Pending

MLS Number 5007795

  • Multifamily
  • Units 4
  • Bathroom 4
  • Acreage 1
  • Square Feet 3,024

Looking to live near the Chester Green? This may be the home for you! Currently used as a four-unit apartment building with one 2 bedroom apartment, one 1 bedroom apartment and two studio apartments. The house is in need of renovation however, the style and location would lend well to that investment.

Listed by Susan LeCours of Barrett & Valley Assoc. Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

1599 Mattson Road Chester VT 05143-8744

Chester, VT1599 Mattson Road

Price$139,000

Est. Mortgage: $/month

Pending

MLS Number 4996169

  • Land
  • Acreage 10.1
  • Area Rural
  • Utilities None
  • PricePerSqFt 13762.38

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 acres of untouched land with possible granite, providing potential for various uses. Don't miss out on this unique opportunity! Contact us for more details.

Listed by Amy Vashaw of Twin State Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

255 Linden Way Chester VT 05143

Chester, VT255 Linden Way

Price$129,000

Est. Mortgage: $/month

MLS Number 5001005

  • Land
  • Acreage 2.01
  • Area Rural
  • PricePerSqFt 64179.1
  • Zoning residential

A very rare find! Here is your chance to own 2+/- acres of beautiful "action ready" land in the town of Chester. Situated in a woodsy setting, your new home will feel intimate and private, yet only a 15 minute walk into the town of Chester. Best of all, the under ground electric, well, septic, cable and gravel pad are existing and ready to be built on! There is a flat upper pad for your home site with a flat lower grass backyard or walkout basement. In addition, enjoy the sound of the babbling brook that is set safely below the home site. This is truly a one of a kind opportunity for your dream home with all your utilities and pad ready to go! A huge money and time saver! This land is ideally located for skiing! Just 18 minutes to Okemo, 30 minutes to Bromley and 45 minutes to Stratton. Grafton is 10 minutes by car, I-91 is just 15 minutes, and Lebanon/Hanover NH is 1 hour. The road has been newly renamed so there is no sign post yet. Use the Directions provided here on MLS.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity 

Copyright 2024 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated September 15, 2024 1:24 PM EDT