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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.

339 Richardson Road Chester VT 05143

Chester, VT339 Richardson Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 4842176

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 5
  • Square Feet 4,326

This home with over 207 accessible acres in both Chester and Andover is perfect for a large family or group. 9 bedrooms including master suite on first floor, 5 full baths, large public spaces, and an oversized 3 bay heated garage with full finished game room overhead. Privately set between Chester, Londonderry and Weston with southern and western views. Top quality, recent construction and all amenities: granite counters, double ovens, central AC, radiant and baseboard heating, large stone fireplace, full house automatic generator, shining wood floors, and comfortable dining seating for 15-20. Sled, ski or snowmobile through the front yard, meadows or wooded trails. Small pond in view from front porch. The land is enrolled in VT Current Use and VT Land Trust for tax reduction and land conservation. Most house furnishings are included - list available.

Listed by Judy Dickison of Barrett & Valley Associates, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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134 Gold River Extension Chester VT 05143

MLS Number 4837125

  • Commercial
  • Acreage 13.42

Rare opportunity with commercial/industrial zoning. 13+ acres of fully permitted subdividable lots. Property can be used in its entirety, or use what you need and market the permitted land parcels to others. Currently there are 6 buildings onsite to include: 1792 sq ft office building; 3364 sq ft garage building with heat, loading dock, and rail siding; 7544 sq ft open span, no ceilings, storage building; 3 additional storage buildings. Property includes an owned rail siding for direct shipment possibilities. Highway access is on Route 11 East, 3/10's of a mile from Route 103, and 9 miles to Route 91, exit 6. Office building has center entry and two administration wings, could be used by two or more businesses. Fiber-optic internet is on site. Garage building is currently used for service of trucking and excavation equipment and includes office area. This building has loading dock and direct access to rail siding. Large former ore shed with 7544 sq ft of open span. Multiple doors to access the building. Survey and permits in place for 7 lot subdivision of the industrial park. Common rail siding to be maintained for all. Currently there is a tenant in the office building. Also offered separately (building lot, ore shed building, or garage/office/storage buildings). Video attached to the MLS.

Listed by Betty McEnaney and Andy Paluch of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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$999,000

Est. Mortgage: $/month

MLS Number 4822981

  • Land
  • Acreage 548
  • Area Near Skiing, Rural
  • 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 543 +/- acres has it all. Made up of 5 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 as well as a 20.1 acre lot with permitted 1 acre +/- Mica Schist stone quarry. 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 throughout 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 and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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816 Popple Dungeon Road Chester VT 05143

Chester, VT816 Popple Dungeon Road

Price$979,000

Est. Mortgage: $/month

MLS Number 4848206

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,676

Welcome to Deer Valley Farm also known as the Williams Homestead. This is the first time the property has been offered for sale in over 60 years! The home has been lovingly cared for with lots of improvements over the decades of ownership. Outside: The barn has undergone major work which insures its stability for years to come and includes a wine cellar. It measures 45x105 with plenty of room for cars, toys or animals. Other improvements include stonework, tennis court and pool with pool house and gardens. The walking bridge over the Williams River includes 4 staircases to the river and built in lights. The home is styled with Italian tile throughout and offers cozy antique charm with 3 fireplaces. The home does need updating but will be well worth the effort. The structure itself has been well maintained. The large acreage easily lends itself to a few other incredible homesites. Located just outside the town of Chester less than 4 hours to NYC and 2.5 hours to Boston. Minutes to all of Southern Vermont amenities including Okemo, Stratton, Killington, Vermont Country Store, Weston Playhouse, world-class golf and the shops in Manchester. This property will not disappoint.

Listed by Lisa Kelley of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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321 Main Street 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: 3.13% last updated on Apr 8, 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 Route Chester VT 05143

Chester, VT698 Vermont RT 11 Route

Price$699,000

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: 3.13% last updated on Apr 8, 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: 3.13% last updated on Apr 8, 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$599,000

Est. Mortgage: $/month

MLS Number 4850599

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

Welcome to the Wiley 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: 3.13% last updated on Apr 8, 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

MLS Number 4851883

  • Commercial
  • Year Built 1904
  • Acreage 0.87

The Historic Wiley 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: 3.13% last updated on Apr 8, 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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92 Vt Rte 11 west Chester VT 05143

Chester, VT92 Vt Rte 11 west

Price$599,000

Est. Mortgage: $/month

MLS Number 4818070

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 4
  • 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.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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

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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 April 13, 2021.