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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$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

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      Price Down Payment Interest Rate Years
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      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.95% last updated on 2017-05-25

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

      141 Stage, Chester, VT 05143

      Price$1,250,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4648068

      • Land
      • Zoning Res/Ag
      • Acreage 552

      A rarity to find so much contiguous acreage. This 552+/- acres is located in Chester & Grafton. A mix of open pasture, woodlands, ponds, potential gravel pit for maintaining the gravel roads found throughout the property. Added bonus with an existing mobile home and large pole barn for storage.

      Listed by Lori Muse of Muse and Associates Real Estate

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

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      Price Down Payment Interest Rate Years
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      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.95% last updated on 2017-05-25

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

      572 Horseshoe Rd, Chester, VT 05143

      Price$1,100,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4645171

      • Residential Single Family
      • Bedrooms 5
      • Bathroom 5
      • Stories 2
      • Construction Existing

      C1850's Hidden Pond Farm blends the classic Vermont farmhouse and setting, views and privacy with tasteful renovation and addition that provide a more open floor plan. Sited on 170 acres at the end of a road shared with just one other residence, the farmstead is surrounded by meadows and includes a swimming pond, 5-stall barn, detached garage and trails throughout the property. The farmhouse, with 4,786 square feet and 5 bedrooms, has a classic New England style with brick fireplaces, antique floor boards and original paneled doors. The addition's complementary style transitions to a great room with high ceilings, big windows and mountain views. Located within 3 miles of Chester village and 7 miles of Route 91.

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

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

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      Price Down Payment Interest Rate Years
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      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.95% last updated on 2017-05-25

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

      231 Christmas Tree Farm, Chester, VT 05143

      Price$989,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4633581

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

      Privacy, Views, Acreage and Authentic Vermont! This dramatic log home began in 1981 as a small classic log cabin; but the big view and setting just deserved more. Between 2003 and 2008 the owner added nearly 3,000 square feet. Now this lovely large home sits at the top of an open meadow easily taking in the dramatic Southerly views. With 245 acres and being located at the end of the private drive, you don't have to see anything but wildlife. The newer Main House features a custom-crafted entry door that was imported from Belgium. It takes you in to a large entry area with an additional room just off the entry that is waiting for your finishing (a large half bath, laundry room or pantry - you decide). The kitchen features high ceilings with skylights, Jenn-aire cooktop, Bosch Dishwasher & GE Profile Refrigerator, granite counters and a wood stove. Just off the kitchen/dining area is a huge living room with large windows to take in the amazing views and a stone fireplace to add warmth and ambiance on a cold evening. This South-central small town of Chester is just 3 hours from Boston, less than 4 hours to NYC and 4 hours to Montreal.

      Listed by Gail Graves-Beardmore and Kenneth Saccardo of Engel & Volkers Okemo-Woodstock

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

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      Price Down Payment Interest Rate Years
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      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.95% last updated on 2017-05-25

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

      465 Pennell Rd, Chester, VT 05143

      Price$975,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4647843

      • Residential Single Family
      • Bedrooms 4
      • Bathroom 5
      • Stories 2
      • Construction Existing

      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

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

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      Price Down Payment Interest Rate Years
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      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.95% last updated on 2017-05-25

      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. 2nd floor apt. could possibly be owners quarters. 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. Sellers will entertain owner financing to a qualified buyer with 30% down

      Listed by Dick Palmer of Hospitality Consultants, LLC

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

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      Price Down Payment Interest Rate Years
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      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.95% last updated on 2017-05-25

      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$495,000The 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

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      Federal 30-year interest rate: 3.95% last updated on 2017-05-25

      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

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      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.95% last updated on 2017-05-25

      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 kitchen 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.! 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

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      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.95% last updated on 2017-05-25

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      350 Farrar Rd, Chester, VT 05143

      Price$368,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4638382

      • Residential Single Family
      • Bedrooms 4
      • Bathroom 3
      • Stories 2
      • Construction Existing

      Step away from the hustle and bustle, leave the pavement, and wind through the tree canopy on a quiet road with gentle curves carved by the rocky stream alongside. Pull into a true Vermont homestead exposing a traditional saltbox, car barn and sugarhouse with sunshine, open lawn and room to park and play. The Green Mountain view from anywhere feels private whether you are working in the organic garden or oversize potting shed, sitting at the fire pit, or enjoying a beverage on the screened porch. Spacious open-living emerges after the entry/mudroom. Granite counters and warm wood cabinets anchor the kitchen side with dining centered and living area enjoying the radiating wood stove. Adjacent is the office/study and beyond are the family room and porch. Light and views from the southern exposure and 8/8 oversize windows is enjoyed all throughout most of the first floor and second. The second floor hosts three bedrooms with hall bath plus a master wing with private bath featuring a custom Vermont slate shower, walk-in closet and skylights. Wood flooring, handcrafted wood doors and access to the bonus area of a walk-up attic complete the upstairs. The lower level finished area is now used as a weight room and unfinished areas as workshop, utilities and lots of storage. The newer detached oversize garage with storage wings offers wood heat on the first floor while the spacious finished upstairs is utilized as an office and heated by propane heater- again with views- Lovely site!

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

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

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      Price Down Payment Interest Rate Years
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      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.95% last updated on 2017-05-25

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

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      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.