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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

Price$1,400,000

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. Pond Meadow Farm is a historic 392 acre estate that 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 current owner has done extensive renovations 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 nearly 400 acres estate. The owner has begun the process of visualizing a great room in the original barn. The space could be heated and plumbed after permitting to create a truly spectacular game room or art studio. 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!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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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40 Common Chester VT 05143

MLS Number 4730339

  • Commercial
  • Year Built 1920
  • Acreage 2.28

For over a century the Fullerton Inn has remained a keystone to historic Chester, Vermont.Though the hands of time have changed the facility and its ownership,The Fullerton has remained an institution.Having continued to deliver excellent quality of service throughout the years, since before the Civil War.The Inn has very spacious public rooms which include a huge reception room with stone fireplace and comfortable seating areas, tavern, several dining rooms, breakfast room, conference room, very large front porches and Rear deck.The front porches take in the activity of the Village plus offer alfresco dining in warmer weather.The huge rear deck allows for privacy and large parties. All 20 guest rooms have private baths and are individually decorated. There are handsome architectural features throughout the Inn.The property has been maintained and shows pride of ownership. She is an Elegant Lady.The owners quarters are a bonus. Large is an understatement. 3 bedrooms 4 baths, Living room w/Fireplace and Kitchen. Extensive upgrades to the property have taken place since the current owners purchased the Inn in 2003.They have paid particular attention to creating comfortable rooms for their guests and still offers the same warmth, comfort and professional service of 150 years ago. This is a wonderful opportunity to own a piece of Vermont History.The Inn is situated on 2.28 acres improved with the Inn, 3 or 4 bay Storage Garage, former horse barn, smaller shed & 2 Tennis Courts.

Listed by Dick Palmer of Hospitality Consultants, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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

Price$900,000

Est. Mortgage: $/month

MLS Number 4647843

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

At the end of a town maintained road and minutes from Okemo, this unique home offers incomparable craftsmanship and majestic views. Privately situated on 79+/- acres, there is a pond, sugar house, 3+ car garage, lighted tennis court and sophisticated tree house.The kitchen is not only beautiful with cherry cabinetry, quartz counters and soapstone floors, but a cook's delight, outfitted with large Subzero freezer and refrigerator, wine refrigerator, refrigerator drawers, Wolf double oven and 6-burner range, Blodgett salamander, warming drawer, dishwasher, compactor, and Winekeeper wine dispenser. The wall of windows in the living area overlooks the pond and beyond with long range views into NH. A round dining room is surrounded in glass and features a mahogany ceiling with a grapevine detail. Main floor also comprises an exquisitely detailed office, hot tub room and 2-room guest suite with kitchenette. Large wrap-around deck expands the living outdoors. Second floor has a grand master suite with views, sitting area, and soapstone bathroom with jetted tub and steam shower. Second bedroom has a sky light, window seats and en-suite bathroom. A stairway leads up to a second office. Walk-out lower level has a hobby room, wine cellar and family room with bathroom that could serve as a fourth bedroom, and plenty of unfinished space for storage. There is an attached garage, a detached 3-car garage with lift and a 18' X 36" sugar house. This property is a special find and must be seen!

Listed by Debra Staniscia of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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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397 Peck Road Chester VT 05143

Price$899,000

Est. Mortgage: $/month

MLS Number 4754549

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,470

Pristinely set on 45 acres of expansive green pastures and shaded woodlands, this Federal style house, built circa 1780, has been completely renovated with historic integrity back to its original beauty. Recent improvements include a refinished kitchen, landscaping and new 12 over 12 mullion glass windows. The home boasts large rooms comprised of a charming tavern with a large attached greenhouse, large living room with enormous fireplace, an ensuite master bedroom, and exterior porches. The homes' original features have been preserved to a high standard, including fireplaces, wide pine floors, moldings, balustrades, and more. Outbuildings include a custom built post and beam barn, four season studio or workshop, potting shed and barn/ four car garage. Outdoor living spaces abound. A stunning bluestone patio with stonewalls and seating overlooks the rivers, mountains and an historic c.1899 train trestle bridge with a wonderful swimming hole. The gardening enthusiast will delight in the 18th century style herb garden, and apple orchard lining a country road. For the equestrian or animal lover there is 600-foot gated corral. Nearby you will find an abundance of four season activities, such as downhill and cross country ski areas, golf, boating. Perfect for your Vermont Haven or a charming B&B.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 Chester VT 05143

Price$775,000

Est. Mortgage: $/month

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: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

231 Christmas Tree Farm Rd Chester VT 05143

MLS Number 4756393

  • 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: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

1502 Popple Dungeon Road Chester VT 05143

Price$699,000

Est. Mortgage: $/month

MLS Number 4762267

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

Be ready to fall in love! Just 3.5 miles from the green in Chester, you will find this stunning Farmhouse built in 1989. A superb country location. The land is split into both sides of the road providing permanent protection. Across the street 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 street, 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 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: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

2595 Flamstead Road Chester VT 05143

Price$595,000

Est. Mortgage: $/month

MLS Number 4760937

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,099

HIGHLAND PONDS FARM epitomizes the pastoral Vermont lifestyle you've dreamed about! The classic 1820's cape-style farmhouse on 28+ac has been carefully maintained and thoughtfully updated. The current owners have enthusiastically stewarded the land by retaining a balanced mix of open lawn and fields, hard/softwood forest, and cleared trails. Two swimming ponds (stocked with rainbow trout) are ready for cooling off in the summer or winter skating parties. A Japanese tea house adorns one pond; the other has its own sauna nearby. The home is sited to take advantage of morning coffee on the farmer's porch and sunsets on the stone patio. Wide pine floors, exposed beams, and custom tiles demonstrate the quality of craftsmanship. Inside is a comfortable living room with wood stove and a big view, a quiet library with fireplace, formal dining room, eat-in kitchen and a spectacular 3-season sunroom, plus first floor bedroom and bath. The master bedroom with custom built-ins and ensuite bath is conveniently separated from the rest of the upstairs bedrooms. On the lower level is a walk-out basement with an office and access to outdoor hot tub. Plant organic veggies in the established raised beds. Berries and assorted fruit trees dot the property. A neighbor grazes his cows in one of the fields. Rustic private guest quarters and a light-filled artist's studio surprise and delight! In a world of uncertainty, Highland Ponds will rejuvenate your soul...

Listed by Susan Hickey of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

101 Stonehedge Lane Chester VT 05143

Price$525,000

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: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

319 Main Chester VT 05143

MLS Number 4743335

  • Commercial
  • Year Built 1985
  • Acreage 8.76
  • Area Business District

This investment awaits your imagination! Are you currently a business owner and need a large facility in the heart of a thriving village? If so, this property has so much potential from its outstanding location to its large, lit parking lot. Formally a restaurant with a large dining room, we are excited to see the transformation a new owner may undertake! The possibilities seem endless, the only thing missing is your business plan and imagination. The property is located in the heart of Chester. A must see!

Listed by Joan Morey and Amanda Stearns of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 2019
* 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 A VisitAsk A QuestionMore Details

Broker Reciprocity

Copyright 2019 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 July 24, 2019.