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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$1,150,000

Est. Mortgage: $/month

MLS Number 4763930

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

Four season retreat with VAST Trail access and great skiing close by. This 158 acre estate provides all you would want in a VT country farm/wilderness property. Sited within it's 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 bldgs include a circa 1780 barn, an 1860 cape and a 1970's addition. The barn is being re-done as a grand finished space. All of the original beams are exposed. It will be a perfect studio, family room or game room upon completion. MUST be seen! The owner has also done extensive renovations to the residence to increase energy efficiency and to merge the older charm with modern improvements. The cape wing of the residence has a stunning state of the art kitchen, an open dining area, a gracious living room with re-worked original floors and a second floor master bedroom. The 1970's addition has been re-worked to enhance the bedroom spaces and the overall flow. A 2nd floor great-room boasts a massive fireplace and a great wrap-around deck to take in the beautiful views of your 158 ac acre 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! Additional +/- 234 acres available.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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: 3.15% last updated on May 28, 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: 3.15% last updated on May 28, 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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1346 Goldthwaite Road Chester VT 05143

Chester, VT1346 Goldthwaite Road

Price$750,000

Est. Mortgage: $/month

MLS Number 4804206

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3,976

Functionality is essential and this custom designed C.2006 three bedroom post and beam home with a seperate two bedroom guest apartment has everything you need to live with ease. Drop your gear in the expansive mudroom and head upstairs where you will find all the main rooms with high ceilings, beautiful light and spaces that take the outside in. Gather large groups around the quarry stone fireplace with raised hearth, entertain outside on the deck while enjoying music from the sound system, relax in the bar/game room which overlooks the meadow and pond, work in your own private office/studio, or take on a project in the workshop. A whole house generator means you'll never be without the amenities you expect everyday. The yard is delightful, mature flowering bushes and trees provide pops of color, fenced in garden with 5 raised beds and additional planting area. The are two separate garages one with three bays and an additional storage space for your ATV's, Snowmobiles and recreational gear, the second garage includes an addtional 2 parking bays and an oversized workshop area with room for ski and board tuning, motorcycle parking and maintenace. Snowmobile to the VAST trails from your house! Target practice in your own shooting range or play Bocce on your own court. The 27 acres is a mix of meadow and woods, pond and brook, a wonderful Vermont retreat.

Listed by Lavinia Lee Brown and Nancy Jensen of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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 master 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: 3.15% last updated on May 28, 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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1502 Popple Dungeon Road Chester VT 05143

Chester, VT1502 Popple Dungeon Road

Price$640,000

Est. Mortgage: $/month

MLS Number 4762267

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,445

Come fall in love! Just 3.5 miles from the green in Chester, is this stunning farmhouse built in 1989. A superb country location. The land is split onto both sides of the road providing permanent protection. Across the road from the house is a large, flat field that is perfect for horses. Over 1,300 feet of frontage along the South Branch of the Williams River. On the house side of the road, you will find multiple outbuildings & barns. Sheep & horses are currently at home here. Gardens, sheds, & a car barn with a huge studio above awaits craftspeople, writers, woodworkers, or exercise enthusiasts. Saving the best for last, the home is just stunning. Covered porches for quiet time. Enter through the front door to large foyer & hall. To the left is a formal parlor, & to the right, a large country kitchen with sitting room. The kitchen is every chef's dream from the appliances to the tile work. The dining room has a wall of windows overlooking the gardens & pasture. A mudroom & first-floor bedroom with bath & walk-in closet round out the first floor. Upstairs are three very generous bedrooms & two baths. The custom features throughout the home are fantastic -- tile work, painting, trim detail & more. The full, dry basement has loads of space. There is fiber optic internet, a generator, wood boiler, along with a traditional multi-zone oil boiler. This is a spot to call home for horse people, home business owners, artisans, families or retirees. Wait until you see it for yourself!

Listed by Betty McEnaney of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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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2356 Lovers Lane Chester VT 05143

Chester, VT2356 Lovers Lane

Price$605,000

Est. Mortgage: $/month

Pending

MLS Number 4617051

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 6
  • Square Feet 4,931

This 73.7 acre farm in Southern Vermont has been carefully managed as a family retreat providing complete privacy, and excellent views. The property includes a c1819 Farmhouse with 4,930 square feet and 6 bedrooms surrounded by stonewalls and beautiful birch trees, a 2-bedroom house, and two antique barns. The diverse landscape includes open meadows suitable for agriculture, a 2-acre pond, orchard and streams. Located just 4 hours from NYC, and 2.5 hours from Boston.

Listed by T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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

101 Stonehedge Lane Chester VT 05143

Chester, VT101 Stonehedge Lane

Price$475,000

Est. Mortgage: $/month

MLS Number 4748048

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 3,516

Beautiful country estate in village setting. Welcome to 101 Stonehedge - located just above the historic Stone Village in the quaint town of Chester. You will be met with a beautiful stone walled entrance and a hedge lined drive. An oversized 3 car garage has plenty of room for your vehicles as well as room to expand above. The atrium welcomes you into the home that is bright with sun filled rooms and quality finishes throughout. The 2 story living room has a fireplace, discreet wet bar, and 2 sets of French doors that lead out to a large deck. A second living space and game room provides ample room for entertaining year-round. The first floor master bedroom wing also has French doors to the deck, a den, walk in closet, and well appointed bathroom. Views of Flamstead Mountain can be seen from most rooms, the deck, and the well designed, easy care, perennial gardens. Nice sprawling grounds with ornamental trees, an arbor, brick pathways and even a chicken coop make this a perfect private retreat. Being centrally located allows ease of access to several ski areas, lakes, hiking, biking, and shopping. Come see what this home has to offer.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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

244 Main Street Chester VT 05143

Chester, VT244 Main Street

Price$470,000

Est. Mortgage: $/month

MLS Number 4721840

  • Residential Single Family
  • Construction Existing
  • Bathroom 8
  • Bedrooms 7
  • Square Feet 4,424

Built in Circa 1820 Victorian Inn is rich with history and located in the heart of Chester Village. Property offers an operating Inn with a gift shoppe, a beautiful Carriage House, flower gardens, chicken coop and peaceful lawn area separating a private cottage at the rear of the property. The Inn has beautiful details and many of its original features . Exquisite woodwork and large windows that allow for natural light. Offering six en-suite bedrooms and a small apartment space just above the gift shoppe. The common spaces include a dining area with a bay window, a cozy den with a gas fireplace and a gracious living room. The detached two-story Carriage House once offered home for horses and has a garage space for one vehicle. Both the Inn and Carriage House are registered on the National Historic Registry. The three bedroom cottage is full of character and offers privacy. Perfect for an owner, inn keeper quarters or an additional rental property. This property is a true gem with so many possibilities.

Listed by Jessica Citera of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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

244 Main Chester VT 05143

MLS Number 4720476

  • Commercial
  • Year Built 1825
  • Acreage 0.6

Built in Circa 1820 Victorian Inn is rich with history and located in the heart of Chester Village. Property offers an operating Inn with a gift shoppe, a beautiful Carriage House, flower gardens, chicken coop and peaceful lawn area separating a private cottage at the rear of the property. The Inn has beautiful details and many of its original features . Exquisite woodwork and large windows that allow for natural light. Offering six en-suite bedrooms and a small apartment space just above the gift shoppe. The common spaces include a dining area with a bay window, a cozy den with a gas fireplace and a gracious living room. The detached two-story Carriage House once offered home for horses and has a garage space for one vehicle. Both the Inn and Carriage House are registered on the National Historic Registry. The three bedroom cottage is full of character and offers privacy. Perfect for an owner, inn keeper quarters or an additional rental property. This property is a true gem with so many possibilities

Listed by Jessica Citera of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 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

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 May 31, 2020.