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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$3,940,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4507606

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

      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

      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: 4.85% last updated on 2018-10-18

      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$3,150,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4669793

      • Residential Single Family
      • Listing Agent Name T Story Jenks
      • Construction Existing
      • Bedrooms 1
      • 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 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
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.85% last updated on 2018-10-18

      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$3,150,000The 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: 4.85% last updated on 2018-10-18

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

      3703 Popple Dungeon Road, Chester, VT 05143

      Price$960,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4704182

      • Residential Single Family
      • Listing Agent Name Debra Staniscia
      • Construction Existing
      • Bathroom 4
      • Bedrooms 4

      Tucked away custom built 4077 sq ft post and beam home designed for permanent or seasonal use sited on 289+ acres. A remodeled custom kitchen with granite counter-tops and cherry cabinetry overlook the large living and dining area with wood burning fireplace. Spacious open floor plan opens to a large deck overlooking the pond and a view of the mountains. Wide plank cherry hardwood floors. The main level offers a guest suite and ski room. The lower level is complete with family room, 2 large bedrooms a full bath and a walk in pantry. The stone patio is accessed from the family room or front bedroom. Upstairs is a private master en suite and loft sitting room. A large bunk room with full bath completes the 3rd level. Outside there is a shower with hot and cold water, a swimming pond, a 200 sq ft cabin, streams, waterfalls, hiking trails and excellent vast access. The detached 1300 sq ft barn and 3 car attached garage offers storage for your toys and cars. Your private retreat with close access to area amenities: skiing, golf, restaurants, Weston and Dorset Playhouses and Manchester outlets. Property is in Current Use and a must see!

      Listed by Debra Staniscia and Jack Menzie 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: 4.85% last updated on 2018-10-18

      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$950,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4645171

      • Residential Single Family
      • Listing Agent Name T Story Jenks
      • Construction Existing
      • Bathroom 4
      • Bedrooms 5

      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: 4.85% last updated on 2018-10-18

      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$900,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4647843

      • Residential Single Family
      • Listing Agent Name Debra Staniscia
      • Construction Existing
      • Bathroom 5
      • Bedrooms 4

      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: 4.85% last updated on 2018-10-18

      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$795,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4633581

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

      At this NEW PRICE, this is an amazing offering!...Privacy, Views, Acreage and Authentic Vermont! This dramatic stone and 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 property is in Vermont's Current Use Program and you can reap the benefits of future Timber Harvesting. 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
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.85% last updated on 2018-10-18

      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$790,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4617051

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

      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

      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
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      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.85% last updated on 2018-10-18

      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$697,000The 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: 4.85% last updated on 2018-10-18

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

      2595 Flamstead Road, Chester, VT 05143

      Price$650,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4707723

      • Residential Single Family
      • Listing Agent Name Katherine Burns
      • Construction Existing
      • Bathroom 3
      • Bedrooms 4

      Highland Ponds Country Estate Living. While maintaining historical charm and traditional New England architecture, this four bedroom, 1820 brick cape has received updates designed for modern living and entertaining. Dutch-tiled fireplace and built-in shelves in the library, classic windows, wood floors and formal dining room showcase original character. Entertaining options abound in the living room with wood stove, sun room and adjacent patio with hot tub. Lovely views of Okemo from the 28 peaceful acres of stone wall-lined pastures, ponds, woodlands and berry gardens. Several outbuildings complete the estate. The artist's studio has an attached 2 car garage, while the cozy guest cottage offers open living, kitchenette, dining room, upper bedroom and loft, and yet another two car garage. Excellent access to nature trail system.

      Listed by Katherine Burns of William Raveis Vermont Properties

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

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      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.85% last updated on 2018-10-18

      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.