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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.

1782 Quarry Road Chester VT 05143

Chester, VT1782 Quarry Road

Price$1,299,000

Est. Mortgage: $/month

MLS Number 4763930

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,866

Now listed with +/- 244 acres! Chester VT ranked as the best small town in VT by Business Insider for 2019. Come and see why! This beautiful estate provides all you would want in a VT country farm/wilderness property. Sited within its own three hilltops and at the end of a town maintained road, there is ultimate privacy. You will find open fields, wooded trails, a swimming pond and beaver ponds, a former soapstone quarry hidden within one of the peaks, a Morton Barn full of equipment and off road vehicles...even a dirt track to test your riding skills! The buildings include a circa 1780 barn, an 1860 cape and a 1970's addition. All fiber connected! The barn is being re-done as a grand finished space with original beams exposed. It will be a perfect studio, family room or game room. The owner has done extensive renovations to the residence to increase energy efficiency and to merge the older charm with modern features. The cape wing has a stunning state of the art kitchen, an open dining area, a gracious living room with re-worked original floors and a 2nd floor master bedroom. And of course Soapstone counters! The 1970's addition has been totally reworked in a very tasteful way. A 2nd floor great-room boasts a massive fireplace and a great wrap-around deck to take in the beautiful views of your country estate. This property has been the dream project of its retired owner and this 5 year plan is coming to an end. This turnkey property awaits its next steward! Do not miss it!

Listed by Mark Roden of BH&G - The Masiello Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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321 Main Chester VT 05143

MLS Number 4811623

  • Commercial
  • Year Built 1854
  • Acreage 0.28

Inn Victoria offers a new owner the opportunity to step into a very successful operation business. The Inn has 9 guest bedrooms all with private baths, assistant managers suite of 10th bedroom, plus 1,000 sq ft owners quarters, first floor professional laundry facility and large public spaces which are beautifully decorated and well maintained. The outdoor patio and wedding garden with 3 large pergolas is idea for small gatherings. The annual occupancy and average daily rate is higher than most B&B's of this size. It is a testament to the current owners sincere dedication to the business and providing a wonderful guest experience. The Inn is a member of a 4 Inn to Inn walking group. The revenue from the Inn to Inn walking tours is substantial. It attracts guests from all over the world. The location is only a few miles from I-91, a north south interstate on the east side of Vermont allowing millions of people within a 4 hour drive to visit the INN. There is also upside to the revenue with an enhanced marketing plan. The Village of Chester is considered one of the most picturesque Villages in Vermont. You do not want to miss out on this opportunity if you are serious about owning a B&B. Benefits of Inn Victoria Written by the Sellers can be found under "D" below the picture above.

Listed by Dick Palmer of Hospitality Consultants, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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465 Pennell Road Chester VT 05143

Chester, VT465 Pennell Road

Price$878,500

Est. Mortgage: $/month

MLS Number 4793511

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,044

This extraordinary residence and property is located in the vibrant community of Chester. Chester is easily accessed from Interstate 91 and is the gateway to many of Vermont best ski areas which creates an abundance of exceptional restaurants, cultural events and recreational options. The property is a south facing, very private 79 acres which consists of well maintained woodlands with a sugarbush and state of the art sugarhouse and open meadows in the forefront of long range views. Located just below the residence is a large swimming, fishing pond with an adjacent lighted tennis court. Trails for hiking, cross country skiing and mountain biking are throughout the property. Truly an exceptional setting that has been enhanced by the residence which is expertly sited to take in all that the property offers. The residence was designed and built by the owner who is a renowned wood craftsman. The level of craftsmanship displayed throughout the house is without equal. The choicest woods combined with incredible execution make for a truly unique environment. Every room and space in the house is warm and inviting while offering efficiency and sustainability. Combine this with state of the art systems and unexpected amenities including an adult sized and scaled treehouse make this property a must see for the discerning buyer. You won't be disappointed.

Listed by Wade Treadway of Wade I Treadway Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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228 Vermont Route 11 Route Chester VT 05143

MLS Number 4757103

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,912

Right outside the Village of Chester tucked away on a hillside, is this tastefully updated contemporary home. Terrific southern views. Totally private. With great separation of space, you will want to invite all your friends. There are four bedrooms each with their own bath including separate guest quarters with a private entrance. Delight in preparing a meal in the brand new kitchen. Dine in front of the stone fireplace. Sip a cocktail in the cozy living room. Snowshoe or mountain bike on the nearby trails. Kick your shoes off in the new slate mudroom. Relax on the outdoor patio in the summertime. So much to enjoy throughout all four seasons in Southern Vermont - close to golf and skiing at nearby Okemo Mountain Resort. This property is enrolled in Vermont's Current Use Plan to manage the forestry and generate tax benefits with additional acreage available for those who seek more land. A perfect Vermont retreat!

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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231 Christmas Tree Farm Road Chester VT 05143

MLS Number 4803064

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,928

Own your own piece of Vermont. This is a rare find, 245 glorious acres of trails, woods, nature and wildlife with stunning views that make this property an incredible oasis to be enjoyed year round. The original home was built in 1981 and started out as a classic rustic Vermont Log Cabin. The home was expanded in 2006 and turned into one of the most unique homes in southern VT. The original cabin can now be part of the main house or a completely separate guest suite with kitchen, dining room, living room with a fireplace, two bedrooms and two full baths with a private entrance. The addition offers a large gourmet kitchen with vaulted ceiling, wood floors, island and granite countertops that open to the dining area. The living room is grand with wide plank pine floors, floor to ceiling windows and doors that bring in the amazing expanse of the property. You can step outside and enjoy the 54X14 deck with outdoor fireplace. The first floor also boasts an entry way and an office. Heading upstairs you will find a lovely owners suite with a balcony to enjoy the breathtaking views of the Green Mountains. The suite has his and her bathrooms with custom marble. The property is a true oasis for the outdoor enthusiasts, hunters and nature lovers. The property is in land use and has excellent income potential with timber. Convenient access to major ski areas, Okemo, Stratton and Bromley. Peace and tranquility is just 4 hours from NYC and Montreal and only 3 hours to Boston

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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698 VT RT 11 West Chester VT 05143

MLS Number 4820670

  • Commercial
  • Year Built 1810
  • Acreage 5.63

An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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698 Vermont RT 11 Route Chester VT 05143

Chester, VT698 Vermont RT 11 Route

Price$750,000

Est. Mortgage: $/month

MLS Number 4820671

  • Residential Single Family
  • Construction Existing
  • Bathroom 12
  • Bedrooms 10
  • Square Feet 6,848

An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

76 Wolf Road Chester VT 05143

Chester, VT76 Wolf Road

Price$725,000

Est. Mortgage: $/month

Pending

MLS Number 4809852

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 4,166

Beautifully appointed above the trees this incredible post and beam home sits on 20.35 acres appropriately named “Cloudbank”. The stunning 360 degree views are second to none and offer glimpses of Okemo, Killington and Mt Ascutney. Beautifully crafted custom-built post and beam with every detail well thought out and executed to perfection. The open floor plan was built around the stunning westerly views. The kitchen boasts a large walk in pantry, granite countertops, high-end appliances and is positioned to look out to the dining and living rooms which is ideal for entertaining guests. Hardwood floors and gas fireplace add to the ambience with French doors that open out to the full house length deck where you can relax and enjoy the incredible sunsets. The first-floor master bedroom with master bath is luxurious with wide plank floors, two person walk in closet and laundry room. Upstairs are 2 large bedrooms with ensuite baths. The walkout lower level has a family room, home office set up with fiber optic high speed internet, 3/4 bath and is perfect for a man cave or bunk house for overflow guests. Other highlights include a 2-car attached garage, side patio for sunny days, small pond, beautiful new stonework around the property, gardens full of perennials, potting shed and 3 bay storage shed. New to the property are 20 solar panels generating over 1,000 Kwh per month and covering the cost of electricity. Located near RT 91 and major ski areas.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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

92 Vt Rte 11 west Route Chester VT 05143

Chester, VT92 Vt Rte 11 west Route

Price$649,000

Est. Mortgage: $/month

MLS Number 4818070

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 2
  • Square Feet 7,610

Built and operated as a successful retail/eat-in bakery/cafe for 20 years, this fascinating structure on 3.5+/- level acres offers possibility for use as a full time residence with a home business, or, with further modification, a unique and spectacular full time home. The amazing cathedral like structure was built in 1997 on an old homestead and attached to the barn which dates back to 1850s. The entire interior is connected and finished as one seamless space. There is a 4-flu chimney which could be made into a beautiful stone fireplace. The open floor plan could be redesigned for living space. The possibilities are endless. 4 bathroom spaces are in place with two half baths to code for public use and two more bath areas with a walk-in tiled shower. A home business such as a dance studio, music space, or any form of retail business would work very well with flexible options as to where the business entrance would be. Walking distance to town, adjoins town rec area. Delayed showings until Aug. 3.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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92 VT Rte 11 West Chester VT 05143

MLS Number 4817827

  • Commercial
  • Year Built 1997
  • Acreage 3.5

Exceptional and exciting commercial offering in Chester on 3.5 acres +/- with over 7,000+/- sf of amazing finished space. Soaring cathedral ceilings and exposed arched beams culminate in a 34 ft high glass pyramid that creates a sense of ethereal balance. The fantastic structure was influenced by the spiritual philosophy of Rudolf Steiner and the great cathedrals of Europe. Anthroposophic shapes and symbols tied to meditative practice are reinforced throughout including a coptic cross design around the massive 4 flu chimney serving the ovens and a large window referencing a Pisces symbol. The building is tiled throughout with radiant heat in the main space and a back-up generator at the ready. Two Handicap access public bathrooms w/skylights are conveniently located near the front entrance. Tucked out of sight, there are two more bathrooms, including a tiled walk-in shower with laundry area and two enclosed spaces for offices and privacy. The attached 1850's attached barn was thoughtfully renovated with exposed beams, a multi level second floor, loading dock, attractive rear entrance with double glass doors and even a dumb waiter! The building has wonderful acoustics and an open floor plan that would lend itself to many occupations. There is a large garden area for farm to table cafe/restaurants and two level, spacious lawns for outdoor venues. Fabulous location within walking distance to village and town rec area. Delayed showings until 8/3.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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 2020 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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 August 15, 2020.