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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, Chester, VT 05143

      Price$4,650,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4507606

      • Residential Single Family
      • Listing Agent Name T Story Jenks
      • Bedrooms 6
      • Bathroom 5
      • Construction Existing

      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 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: 4.62% last updated on 2018-06-14

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

      2356 Lovers, Chester, VT 05143

      Price$3,750,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4634314

      • Land
      • Listing Agent Name T Story Jenks
      • 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

      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: 4.62% last updated on 2018-06-14

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

      2356 Lovers, Chester, VT 05143

      Price$3,750,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4669793

      • Residential Single Family
      • Listing Agent Name T Story Jenks
      • Bedrooms 1
      • Construction Existing
      • Square Feet 650

      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 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: 4.62% last updated on 2018-06-14

      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$1,025,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4645171

      • Residential Single Family
      • Listing Agent Name T Story Jenks
      • Bedrooms 5
      • Bathroom 4
      • 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: 4.62% last updated on 2018-06-14

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

      2356 Lovers, Chester, VT 05143

      Price$990,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4617051

      • Residential Single Family
      • Listing Agent Name T Story Jenks
      • Bedrooms 6
      • Bathroom 5
      • Construction Existing

      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 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: 4.62% last updated on 2018-06-14

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

      231 Christmas Tree Farm Road, Chester, VT 05143

      Price$989,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4633581

      • Residential Single Family
      • Bedrooms 4
      • Bathroom 4
      • Construction Existing
      • Square Feet 3808

      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: 4.62% last updated on 2018-06-14

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

      465 Pennell Road, Chester, VT 05143

      Price$975,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4647843

      • Residential Single Family
      • Listing Agent Name Debra Staniscia
      • Bedrooms 4
      • Bathroom 5
      • 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: 4.62% last updated on 2018-06-14

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

      397 Peck Road, Chester, VT 05143

      Price$899,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4696981

      • Residential Single Family
      • Listing Agent Name Daire Gibney
      • Construction Existing
      • Bathroom 5
      • Bedrooms 5

      Within the Okemo Valley region of southern Vermont the charming “Williams River House" is located in Chester, one of the most scenic towns in the Green Mountains. 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. Improvements include new 12 over 12 mullion glass windows, large rooms comprised of a charming tavern, 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, chicken coop, potting shed and barn/garage. Outdoor living spaces abound with a bespoke fire pit, stone terraces, courtyards and hilltop gazebo, all with spectacular views of Fox chair mountain and the Williams River. Stunning bluestone patio with stonewalls and seating overlooks the rivers, mountains and an historic c.1899 train trestle and your own 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 a new 600-foot gated corral. Nearby is an abundance of four season activities, such as downhill and cross country ski areas, golf, boating. Perfect for your Vermont Haven or charming B&B.

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

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

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      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.62% last updated on 2018-06-14

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

      76 Wolf Road, Chester, VT 05143

      Price$799,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4696447

      • Residential Single Family
      • Listing Agent Name Gary Coger
      • Construction Existing
      • Bathroom 5
      • Bedrooms 3

      Beautifully appointed above the trees this incredible post and beam home sits on 20.35 acres appropriately named “Cloudbank”. The stunning 360 degree views are second to none and offer glimpses of Okemo, Killington and Mt Ascutney. Beautifully crafted custom-built post and beam with every detail well thought out and executed to perfection. The open floor plan was built around the stunning westerly views. The kitchen boasts a large walk in pantry, granite countertops, high-end appliances and is positioned to look out to the dining and living rooms which is ideal for entertaining guests. Hardwood floors and gas fireplace add to the ambience with French doors that open out to the full house length deck where you can relax and enjoy the incredible sunsets. The first-floor master bedroom with master bath is luxurious with wide plank floors, two person walk in closet and laundry room. The master bedroom also has its own private access to a deck sitting area where you can spend the morning reading and having coffee. Upstairs are 2 large bedrooms each with private full baths. The walkout lower level has a family/rec room perfect for a game room, man cave or a bunk room for overflow guests. There is also a large storage room and a ¾ bathroom. Other highlights include a 2-car attached garage, side patio for sunny days, small pond, gardens full of perennials, potting shed and 3 bay storage shed. Located near RT 91 and major ski areas. This is truly a wonderful property.

      Listed by Gary Coger 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: 4.62% last updated on 2018-06-14

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

      147 Mineral Springs Road, Chester, VT 05143

      Price$483,900The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4670570

      • Residential Single Family
      • Listing Agent Name Amanda Stearns
      • Bedrooms 3
      • Bathroom 3
      • Construction Existing

      Your own piece of Vermont on top of the world! Come take in all of this spacious contemporary has to offer with spectacular mountain views including Okemo Mountain. It is situated just right on 41 plus acres on the outskirts of picturesque, Chester, VT. Travel up the private driveway and admire the handsome stonework that surrounds the house including a large stone patio perfectly placed to enjoy the views. The over-sized car garage is perfect for all of your toys! Come in the front door and take in the hand painted mural, continue on into the great room with cathedral ceilings, a massive fireplace which is the centerpiece of the home, a wet bar and floor to ceiling windows. The chef's kitchen is massive and boasts granite counter-tops, plenty of cabinetry, a warm wood stove and a lovely breakfast area. The master suite is where you might find yourself spending lots of time having access to the spa room that enjoys an in ground hot tub, perfect for relaxing after a long day on the slopes as well as large windows to enjoy the stunning view. The main level enjoys two more spacious bedrooms and two full baths. The loft has additional sleeping space for guests and overlooks the great room. This property has it all and is an exceptional value for all it has to offer. Don't miss an opportunity to claim this amazing piece of Vermont which is just a short distance Ludlow, Chester and Springfield.

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

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

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      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.62% last updated on 2018-06-14

      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 2018 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.