Our mobile site is optimized for smaller screens.

TRY IT NO THANKS
Advanced Search

      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$5,500,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4507606

      • Residential Single Family
      • Bedrooms 6
      • Bathroom 5
      • Area Mountain
      • Stories 2

      This 1,929 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, Caretaker 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 and Wade Weathers of LandVest, Inc/Woodstock

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.17% last updated on 2017-02-09

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      2356 Lovers Lane, Chester, VT 05143

      Price$1,550,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4617051

      • Residential Single Family
      • Bedrooms 6
      • Bathroom 5
      • Area Mountain
      • Stories 2

      This 118 acre farm in Southern Vermont has been carefully managed as a family retreat providing complete privacy, and excellent views. The property includes a c1819 brick farmhouse with 4,930 square feet and 6 bedrooms surrounded by stonewalls and beautiful birch trees, a 2-bedroom guest house, 2-bedroom caretaker 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. Additional land available, see MLS 4507606.

      Listed by T Story Jenks and Wade Weathers of LandVest, Inc/Woodstock

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.17% last updated on 2017-02-09

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      90 The Common, Chester, VT

      Price$625,000The price has recently decreased

      MLS Number 4625158

      • Commercial
      • Year Built 1880
      • Acreage 0.16

      Fabulous opportunity for an Investor or a Chef Owner to step into a very successful operating restaurant business located on one of Vermont's most photographed Town Greens."The Free Range Restaurant"speaks for its self. Just look at the reviews posted on Trip Adviser. The current owners are an entrepreneurial couple who were never in the restaurant business. But after spending their career in the corporate world and retiring decided to follow their passion of food and wine. To that extent they purchased a neglected Victorian Home on the Green in Chester, Vermont, once the location of another successful restaurant, remodeled it with love and care, hired a wonderful Chef and great staff and that is the beginning. They have some other things that they would like to accomplish and have decided it is time for them to offer their bounty of success with "The Free Range Restaurant" to the next operator.They have an outstanding staff in place who have aided in the success of the business and this affords a new owner the opportunity to hit the ground running. There is plenty of upside to the business should a new owner decide to be open for lunch and holidays. There is a 2nd floor apt.which is currently rented but could possibly be owners quarters. The apt has a separate entrance at the rear of the building. It consists of 2 bedrooms, remodeled bath & kitchen, family room w/propane fireplace & laundry room,possible 3rd BR on 3rd fl. must meet fire code. NOT utilized presently

      Listed by Dick Palmer of Hospitality Consultants, LLC

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.17% last updated on 2017-02-09

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      902 Cummings, Chester, VT 05143

      Price$549,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4628625

      • Residential Single Family
      • Bedrooms 5
      • Bathroom 3
      • Area Other
      • Stories 2

      This quintessential Farmhouse has many unique features throughout, including a fireplace in the kitchen, living room, and master, the home is prominently sited on 10 acres of farmland with a separate barn for animals and another that houses an indoor swimming pool and hot tub! A large first floor Master Suite and expansive Great Room shares views both in the front and back of the farmhouse of the pasture land. Enjoy the screened in patio and fenced in yard area out back! The home's central eat-in Kitchen joins casual living spaces with the more formal Living & Dining Rooms, Upper-Level Guest Bedrooms. Beautiful stone walls surround this classic New England Style home that reaps the benefits of the surrounding farmland and picturesque setting, and offers fun for all with the pool and animal barns!

      Listed by Carrie Mathews of William Raveis Winhall

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.17% last updated on 2017-02-09

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      244 Main, Chester, VT 05143

      Price$490,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4617243

      • Residential Single Family
      • Bedrooms 7
      • Bathroom 8
      • Stories 3
      • Construction Existing

      Come explore this charming, historic Victorian home located in the heart of the Chester Village on the Village Green of shops and restaurants, adjacent to a historical schoolhouse, a cemetary dating back to 1761 and city owned open space. Built circa 1820, the Inn was established in 1982 and is currently an operating BnB Inn. It has been lovingly maintained over the years and it shows. Appreciate the grand staircase, the exquisite bay windows, turret and wrap around porch. Enjoy the formal entry, comfortable living room, and the oak pocket door entry to the library! Relax with a book by the fireplace! The 2nd floor has 7 bedrooms all with private baths and plenty of closet space. The house and carriage barn buildings are on the National Historic Registry.At the back of the house, in the attached barn is the current toy and teddy bear shop. Additional to the property is a two story carriage horse barn. In the rear of the property stands a delightful 3 bedroom, 2 bath cottage ready for service as an inn keeper cottage, MIL, or income producing rental. This property includes an expansive yard for family activities, pets, and even chickens. This amazing home, rich in history, is ready and waiting for your commercial or residential inquiry. Okemo, Magic & Grafton Nordic SKi Center are all close by.

      Listed by Susan Wylie of Vermont Realty Group

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.17% last updated on 2017-02-09

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      147 Mineral Springs, Chester, VT 05143

      Price$484,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4377572

      • Residential Single Family
      • Bedrooms 3
      • Bathroom 3
      • Stories 1.5
      • Construction Existing

      Perched high on a hill with sweeping panoramic mountain views to include Okemo is this custom contemporary home. The kitchen boast wood cabinetry, stainless appliances and granite counters. Large bedrooms, to include the master suite with adjoining hot tub room with one of many hand painted murals. The Greatest of great rooms is a wide open concept of the dinning, living and wet bar with sitting area flooded with natural light from many large Anderson windows and sliders. Enhanced with wood floors, exposed beams, tongue and groove wood cathedral ceiling and beautiful stone fireplace. Above the loft area 16x25 with natural wood stairs and railings. The downstairs is a blank canvas of 3,500 sq ft of wide open space. This exceptional home is easy to maintain with quality vinyl siding. Over sized 2 car garage, grounds are graced with stone walls, mowed lawn and 40+ acres of play ground. A must see to appreciate all of the its fine qualities and the exceptional long range panoramic views.

      Listed by Frank Provance of Diamond Realty

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.17% last updated on 2017-02-09

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      2319 Vt Route 11, Chester, VT 05143

      Price$449,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4504491

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

      Kingdom Valley Farm. Enjoy a visit to this beautiful antique farm house with graceful pillars greeting you as you arrive.All the original detail you are seeking mixed with the modern conveniences we need!Large open living area encompasses the country kitchen, dining room, tavern area and parlor.Big pantry, office and family room also on the first floor. Large bedrooms, high ceilings and beautiful wood floors at the top of the stairs.Big closets, nooks and crannies everywhere, built-ins a bunch! Passers-by in the springtime enjoy the line of lilac bushes that shield the farm house from the road. It is a hallmark of this farm for as long as most of us can remember! Tall maples provide privacy and surprisingly traffic noise is minimal at this property. Enjoy the easy access to RT#11. Sugar house is ready for its next productive sugar season. Barns and outbuildings are in great shape. Established gardens and trails up the hillside.Also a private cabin retreat up the hillside!

      Listed by Rebecca Sanford of Walnut Hill Realty, LLC

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.17% last updated on 2017-02-09

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      7 Pine View Drive, Chester, VT

      Price$425,000The price has recently decreased

      MLS Number 4603243

      • Commercial
      • Year Built 2007
      • Acreage 1.56

      In 2007, Artists built an incredible 3,000 sq ft building on 103 South in Chester, Vermont. They chose this location for their business because of it's hometown location flavor as well as it's placement on one of the most traveled roads in southern Vermont. The building, designed by architect Dan Ferguson , was designed for multi-purpose use. Recently a 25 seat cafe (Green Leaf Cafe), was added to the mix. A portion of the building is also permitted for classes or large gatherings. The owners would like to see the building and property used to promote Crafts and Arts as well as other community orientated, cooperative, and nonprofit ventures. The property is for lease or for sale for this type of venture. We look forward to your thoughts, ideas, and offers!

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

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.17% last updated on 2017-02-09

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      15 DEPOT STREET, Chester, VT

      Price$395,000The price has recently decreased

      MLS Number 4467042

      • Commercial
      • Area Business District
      • Year Built 1850
      • Acreage 0.12

      A one-of-a-kind opportunity! This beautifully redone commercial property consists of a spacious studio with black walnut floors, audio system/media room, A/C, and LED lighting. Main floor commercial space also has a full kitchens and two 1/2 bathrooms. Upstairs you'll find two cheerfully redone apartments, a one bedroom and a two bedroom which includes a unique loft space that the owner found while renovating.Both apartments have fully equip kitchen and baths. Head down to the basement to find a temperature and humidity controlled room for storing pieces of art, delicate papers, you name it! This is a wonderful opportunity for a retreat, art gallery, cafe, yoga studio, you name it in the beautiful town of Chester! The property sits just steps from the town Green

      Listed by Carrie Mathews of William Raveis Winhall

      Rutland
      182 Woodstock Avenue
      Rutland VT, 05701
      Office: 802-773-3500

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.17% last updated on 2017-02-09

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      159 Murdock, Chester, VT 05143

      Price$349,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4494083

      • Land
      • Area Rural
      • Zoning R
      • Acreage 90

      Big views of valleys and mountainsides from this private piece of land. Build your dream home, be it an incredible vacation retreat, primary estate or hunting preserve. A drilled well, septic for 4 bedroom home, electric and internet is on the site. Fronts on the Willimas River which is known for it's hotspots! If removed from Land use, buyer to pay penalty.

      Listed by Rebecca Sanford of Walnut Hill Realty, LLC

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.17% last updated on 2017-02-09

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      Broker Reciprocity

      Copyright 2017 Northern 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. Subject to errors, omissions, prior sale, change or withdrawal without notice. This web site is updated daily.