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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.

2356 Lovers Lane Chester VT 05143

Price$3,940,000

Est. Mortgage: $/month

MLS Number 4507606

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

This 1,881.19 acre farm in Southern Vermont has been assembled over 40 years and carefully managed as a family retreat providing complete privacy and excellent views. The property includes a c1819 Farmhouse with 4,930 s.f. and 6 bedrooms, Guest House with 2 bedrooms, 2 Antique Post & Beam Barns, and a secluded Log Cabin. The diverse landscape has 60 acres of meadows suitable for agriculture, a stocked 2-acre pond, orchards, streams, and 3.5 miles of top grade access roads throughout the property. The 1,839 acres of carefully managed northern hard wood forest, predominate in Sugar Maple, has a Timber Capital Value estimated at $2.67M. Located 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: 4.06% last updated on May 23, 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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2356 Lovers Lane Chester VT 05143

Price$3,150,000

Est. Mortgage: $/month

Pending

MLS Number 4669793

  • Residential Single Family
  • Construction Existing
  • Bedrooms 1
  • Square Feet 650
  • Acreage 1804

One of the best investments on the market today. Chester Forest consists of 1,803.79 acres of well-stocked and managed forest with over $2.6 million of standing timber, dominated by Sugar Maple. On the property is an easily accessible 650 square foot log home built in 1991 from logs harvested from the land and set in an apple orchard field with tremendous views to the southwest.

Listed by T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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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2356 Lovers Chester VT 05143

Price$3,150,000

Est. Mortgage: $/month

Pending

MLS Number 4634314

  • Land
  • Acreage 1807.49
  • Zoning Rural

One of the best investments on the market today. Chester Forest consists of 1,807.49 acres of a well-stocked and managed forest with over $2.67 million of standing timber, dominated by Sugar Maple. On the property is an easily accessible 650 square foot log home built in 1991 from logs harvested from the land and set in an apple orchard field with tremendous views to the southwest.

Listed by T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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: 4.06% last updated on May 23, 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: 4.06% last updated on May 23, 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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2356 Lovers Lane Chester VT 05143

Price$790,000

Est. Mortgage: $/month

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: 4.06% last updated on May 23, 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

1502 Popple Dungeon Road Chester VT 05143

Price$699,000

Est. Mortgage: $/month

MLS Number 4736271

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • 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 Bean Group / Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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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101 Stonehedge Lane Chester VT 05143

Price$539,000

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 Stonehedge 101 - 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: 4.06% last updated on May 23, 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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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 Amanda Stearns and Joan Morey of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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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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: 4.06% last updated on May 23, 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 May 25, 2019.