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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.

465 Pennell Road Chester VT 05143

Chester, VT465 Pennell Road

Price$1,135,000

Est. Mortgage: $/month

MLS Number 4869423

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • 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 Vermonts best ski areas which create 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 including a sugarbush with 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: 2.88% last updated on Sep 9, 2021
* 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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141 Stage Road Chester VT 05143

Chester, VT141 Stage Road

Price$925,000

Est. Mortgage: $/month

MLS Number 4822981

  • Land
  • Area Near Skiing, Rural
  • Acreage 526.4
  • Utilities None
  • Zoning Residential

Don't miss the rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning 526 +/- acres has it all. Made up of 4 contiguous preexisting lots the parcel has road frontage on Stage Road in Chester giving multiple opportunities for a number of small subdivisions. Three lots also front onto route 35 between Chester and Grafton which includes two 70 +/- acres lots. There are also gravel deposits on the site which could be used to develop the logging trails further. If you have conservation on your mind the entire lot is enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded and hosts a large open area for staging a logging operation. There are also a network of marked logging trails throughout the property making it easily accessible. The beautifully crafted ponds offer a welcome spot to take in the beauty of the landscape as well attracting all manner of wildlife. The seller will entertain selling individual lots separately. Whether you wish to develop or keep this pristine site as is you will find endless choices and opportunity for this very special place. Come see today!!

Listed by Daire Gibney of Barrett & Valley Associates,Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 2021
* 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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445 Trebo Road Chester VT 05143

Chester, VT445 Trebo Road

Price$859,000

Est. Mortgage: $/month

MLS Number 4860366

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 3,818

This custom one-of-a-kind timber frame home sits on 10+ acres, located just outside the charming village of Chester. The stunning craftsmanship, and superior quality of this home is evident from the moment you step inside. Surrounded by beautiful scenery, the open layout boasts vaulted ceilings in the great room and radiant heat maple flooring throughout. An abundance of natural light streams into the living space where a modern kitchen includes a built-in grill and stainless-steel, Energy-Star appliances. There is an en-suite primary bedroom, guest room, and guest bath on the first floor along with an office/study built for two. A separate entrance from the attached, heated two-car garage opens into a mudroom/laundry room with exquisite slate flooring. The second floor incorporates an open loft area overlooking the great room and surrounded by three bedrooms and a full bath. Central AC, and whole house ventilation allows you to enjoy this home in all four seasons. The pastoral grounds accented by stone walls, an orchard, and a hillside backyard highly favorable for solar panel placement, largely out of view. This idyllic property is close to Okemo Mountain Resort and many golf courses, and the villages of Chester and Ludlow. You must see this stunning home and the beautiful private grounds to be able to . describe the fulfillment of living in this classic Vermont home. Owners are relocating.

Listed by Suzanne Garvey and Michael Normyle of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 2021
* 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 ROUTE 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: 2.88% last updated on Sep 9, 2021
* 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 Chester VT 05143

Chester, VT698 Vermont RT 11

Price$650,000

Est. Mortgage: $/month

MLS Number 4820671

  • Residential Single Family
  • Construction Existing
  • Bedrooms 10
  • Bathroom 12
  • 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: 2.88% last updated on Sep 9, 2021
* 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

38 Vt Rte 11 West Chester VT 05143

Chester, VT38 Vt Rte 11 West

Price$550,000

Est. Mortgage: $/month

Pending

MLS Number 4850599

  • Residential Single Family
  • Square Feet 5,976
  • Bathroom 5
  • Bedrooms 12
  • Construction Existing

Welcome to the Wylie House, a historic 12 bedroom, 5 bath home on .87 acres with many original details such as Victorian gingerbread, stained glass, an elegant period stairway and a rustic, original 2 story barn. The updated kitchen has attractive tile flooring, crown moldings, center island and a lovely eat-in area with a nook to enjoy morning coffee/tea. The living room has a brick hearth for a wood or pellet stove and built-ins for a great study/home office. The main bedroom features a lovely picture window overlooking the garden & a full bath w/clawfoot tub. An additional front bedroom could also serve as living area. Upstairs there are 2 baths, 5 bedrooms and a finished 3rd floor w/full bath, common area and two additional bedrooms. A 2004 addition adds a spacious gathering room that opens to the large rear deck. A huge, light and bright bonus space w/cathedral ceilings on the 2nd floor is perfect for yoga, a home theater, craft room or professional space. The attached rustic 2-story barn is an amazing space w/an efficiency kitchen, woodstove, full bath, laundry area and large picture window. A custom detailed stairway leads to 3 bedrooms on the 2nd floor. The yard has been lovingly cultivated with perennial gardens and features a garden cottage shed, outdoor sauna, workshop, studio/office wood storage and gazebo. An auto generator keeps things running smoothly and an outdoor wood boiler is a great alternative for heat! Next to town rec area & walkable to town.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 2021
* 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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38 Vt Rte 11 West Chester VT 05143
Pending

MLS Number 4851883

  • Commercial
  • Year Built 1904
  • Acreage 0.87

The Historic Wylie House on .87 +/- acres with 12 bedrooms and 5 baths would lend itself to many commercial uses such as office/professional space, bed and breakfast, mutli-units, air b&b rentals, a retreat or a ski house. An owner occupied therapeutic retreat for many years, the property would also convert to a 3 unit or as owner occupied with a 2 unit rental that would be easily leased, rentals are in demand! A large 2 story addition with radiant heat would make a wonderful professional meeting space, yoga/exercise space or alternative school. The adjoining barn with efficiency kitchen, 3 bedrooms and bath could be an event space or separate apartment. The yard has multiple, customized sheds including a sauna, an office/studio with heat and water, a work shop, garden shed, potting shed and gazebo. A whole house propane generator and outdoor wood boiler provide back up and alternative heat. The yard adjoins the town park in the back which offers skating, disc golf, skateboard park, outdoor pool, tennis courts and a sledding hill.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 2021
* 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

266 Main Street Chester VT 05143

MLS Number 4837044

  • Commercial
  • Year Built 1780
  • Acreage 0.75

This circa 1780's stunning, country inn is located in the heart of Chester and southern Vermont, the ideal setting for a hospitality business. Owned and operated with care, this home and it's owners have provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. This well established business is ready for you to put your mark on the hospitality for the long list of returning guests! The 7 guest rooms and common areas are fully furnished. The newly renovated owners quarters, including two spacious bedrooms, will be unfurnished allowing your own personal décor. Enjoy a comfortable lifestyle in Vermont, in concert with your guests! The main floor is easily accessible with first floor accommodations for those needing to avoid stairs. Gracious rooms and cozy common areas invite you to relax. The central village location allows easy access to the surrounding community on foot!. Come see this charmer; you may want to stay awhile!

Listed by Daire Gibney and Joan Morey of Barrett & Valley Associates,Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 2021
* 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

266 Main Street Chester VT 05143

Chester, VT266 Main Street

Price$539,000

Est. Mortgage: $/month

MLS Number 4845016

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 9
  • Square Feet 5,242

This 1780's stunning yet quaint home in the heart of Chester and Southern Vermont is truly the ideal location for a spectacular private residence or successful hospitality business. Owned and operated with love this building has provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. The period home with newly renovated 2 bedroom separate living quarters comes mostly furnished leaving you space to add your personal touches. The main floor is easily accessible with first floor accommodations for those needing to avoid stairs. Gracious rooms and cozy common areas invite you to relax in a central location allowing easy access exploring the surrounding Chester village and with mountains, lakes and streams all within short drive you will not lack options for fun and relaxation. Come see this charmer; you may want to stay awhile!

Listed by Daire Gibney of Barrett & Valley Associates,Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 2021
* 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

690 Trebo Road Chester VT 05143

Chester, VT690 Trebo Road

Price$475,000

Est. Mortgage: $/month

Pending

MLS Number 4877533

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,112

Country colonial playground - Everything just feels right from the moment you pull in the driveway and slide into the large two car attached garage. Spacious oversized modern kitchen with cozy woodstove in the dining area will keep you warm on those long winter days. A half bath, bedroom and "comfy" living room round out the main floor. A large deck spans the full width of the house to take in the beautiful eastern views and fields. Upstairs are a private master suite with a beautiful tiled bath, two bedrooms and another tiled bath. The full basement is ready for a transformation to a movie or rec room. Current owners have sheep and chickens but you can remove the fencing and open the land back up. There are endless trails woven throughout the 19 acres consisting of open fields and woodland. There's even a small creek that runs through the bottom corner of the lot. Outbuildings consist of a heated "she shed", a free standing two car work barn, a run in shed and a chicken coop. This updated home is equipped with a state of the art solar array. If you are looking for your slice of Vermont, this charming house is minutes off Rte 103 and a five minute ride to Smitty's general store for some of the best deli meats, craft beer and sandwiches in the area.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 9, 2021
* 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

Broker Reciprocity

Copyright 2021 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 September 16, 2021.