Chester and Grafton VT and Area Towns Real Estate

Below, browse all real estate for sale in Chester, Andover, Grafton and Windham Vermont. Don't hesitate to contact us today for more information and to schedule a tour.

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1100 Farrar Road Andover VT 05143

Price$189,000

Est. Mortgage: $/month

MLS Number 4777706

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 1
  • Construction Existing
  • Zip 05143

Almost to the end of a long, winding country road, this 3 bedroom, 1 bath contemporary home with a mountain view on 6.2 +/- acres awaits your enjoyment. Built in 2006, the open concept living space is enhanced by a soaring cathedral ceiling with natural woodwork, arts & crafts lighting, hardwood and cork flooring and an attractive wood stove on slate hearth. Sliders to rear deck and front covered porch provide easy access to the private, wooded outdoors which even includes a frog pond! The first floor master bedroom has sliders to the large deck and view and a bright, spacious 2nd floor bedroom provides ample additional living/sleeping quarters. The walkout basement is ready to be finished and has been prepped for a second bath. A separate drive under garage provides storage for atv's/snowmobiles/lawn equipment while the detached insulated 1 car garage has room for your vehicle and workshop space. If privacy and outdoor recreation are must haves for your criteria, don't miss this property which has been the owners special retreat for many years. Direct access to VAST.

Listed by Geralyn Donohue of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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935 Andover Ridge Road Andover VT 05143

Price$339,000

Est. Mortgage: $/month

MLS Number 4777229

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 2
  • Construction Existing
  • Zip 05143

Just in time for Fall Foliage...come enjoy spectacular, long-range views overlooking the Village of Weston! Experience the stunning sunsets and thirty mile views of the Vermont mountains from every major room in the house. Plenty of space for family & friends in this architecturally unique, four bedroom, two bath contemporary chalet, featuring a three story energy efficient Solar Sunspace. The spacious living room boasts a cathedral ceiling, wet bar & new triple glazed oversized windows. Dining area opens to the living room and shares new circular soapstone-clad wood-burning stove. Upper level comfortable Master suite has incredible mountain views, master bath & plentiful closet space. Ground level features 3 bedrooms with new windows and thermal window treatments as well as a split bath, 6 person Sauna and cozy family room area. The basement level provides additional finished recreation room and a new 200 bottle custom wine cellar & custom paneled wall & door. The architect of this energy efficient home receives high accolades/awards for his quality construction & energy efficient design. Conveniently located between Chester & Weston; less than 30 minutes to Okemo, Stratton, Bromley & Magic ski resorts; hiking trails, VAST snowmobiling trails, swimming and kayaking. 2 miles to the charming village of Weston & the Weston Playhouse & the iconic Vermont Country Store. Are you ready to start living your Vermont dream? Come relax and enjoy the solitude of 935 Andover Ridge!

Listed by McLaughlin Team of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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1490 Middletown Road Andover VT 05143

Price$579,000

Est. Mortgage: $/month

MLS Number 4773375

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 3
  • Construction Existing
  • Zip 05143

Year round beauty is found on this gorgeous 12.5 acre horse property. The tree lined driveway leads you to a lovely contemporary home featuring 4 bedrooms and 3 baths including a large first floor master with master bath with a large jacuzzi soaking tub. Country style kitchen with granite counter tops, double sink and double oven with eat in counter space. The dining room features hardwood floors and sliding glass doors that lead to a 20X12 deck overlooking the breath taking property and mountain views. The living room has a wood burning F/P for those winter nights. The upstairs boasts 3 more good sized bedrooms and a full bath. In basement you'll find a family room with pellet stove, 3/4 bath, laundry and lots of extra storage all connecting to the walk out garage. The property is wonderfully maintained with a back patio off the kitchen to sit and relax. The 48X36 barn is truly exceptional. Center aisle with 5, 12X12 stalls that have double planked walls w/rubber mats, water and overhead lighting. Insulated heated tack room and wash stall w/hot and cold water. Feed and storage room, hay drop area. 2000 bale hay storage. 50X50 paddock w/ 36X12 run in shed. 100X200 riding arena. Beautiful fenced in pastures. Outstanding location on Middletown Rd just a short drive to Chester, Weston and Londonderry. Located in the middle of ski country with Okemo, Bromley, Magic and Stratton Mountain resorts just a short drive away. Come and take a look at this one of kind offering.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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42 Cobb Road Andover VT 05143

Price$225,000

Est. Mortgage: $/month

MLS Number 4773023

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05143

Immaculate and cozy 3 bedroom two bath ranch style home, sits perfectly on 1.60 acres that have been beautifully landscaped, in the town of Andover. Inside, find an open floor plan with spacious living room and large picture window, perfect for admiring the incredible mountain views. The home also enjoys a galley kitchen, cozy dining area and a rear deck, perfect for grilling in the summer months. Travel down the hall to find 2 large bedrooms, a fully updated bath, as well as a nice master with new 1/2 bath. The basement is completely dry and could easily be finished off to add more space. Included, is a brand new industrial dehumidifier, as well as a state of the art sump pump system, whole house Kohler generator and foam insulation. With two-bay garage, newer vinyl windows, exterior doors, heating system, central air system and a fresh paint job, this home is ready and waiting for your personal touches. Only minutes to Ludlow and Chester.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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519 Spruce Drive Andover VT 05143

Price$275,000

Est. Mortgage: $/month

MLS Number 4771733

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 3
  • Construction Existing
  • Zip 05143

This fun, very well-maintained mountain home is perfect for all seasons and winter sports enthusiasts will be especially happy! Snowmobile and cross-country skiing trails run along the edge of the property and it is an easy 15 minute drive to Ludlow and great skiing at Okemo Mountain. The property is mostly level, offers all-day sun and there are stunning wide-ranging long-distance views. The light-filled house was designed to take advantage of the location and views and it offers creative and comfortable spaces with room for the family (and more). There are three bedrooms, plus a den and a loft, and the house offers plenty of room to spread out and make yourself at home . . . or, it can comfortably accommodate a group. The 6.69+/- acres includes 2+ acres of open meadows and another 4+ acres of beautiful hardwood forest. The beautiful wood siding has the patina of an old Vermont barn (but none of the trouble or draftiness!) and there is a one-car garage at the house, a detached two-car garage/barn with a finished upper level and storage shed. The house is truly turn-key and is offered mostly furnished.

Listed by Claudia Harris of Mary Mitchell Miller Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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5303 Windham Hill Road Windham VT 05359

Price$120,000

Est. Mortgage: $/month

MLS Number 4767815

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 1
  • Construction Existing
  • Zip 05359

AFFORDABLE! If you are looking for an affordable get away vacation home, or a more than affordable primary home, this is it! Close to Skiing and all that southern Vermont has to offer in recreation, this home is in a perfect location for either summer or winter sports. If you want to downsize and retire, there is a first floor bed and bath for aging in place! The second floor bedroom is amazing with lots of windows and plenty of extra room to hide away. Starting out? The basics are here, take your time and add to the cosmetics to make this your own. Sitting in it's own little meadow, you will love coming home to the peace and quite of a small village, close enough to action but just far enough away to appreciate the country.

Listed by Christine Lewis of Brattleboro Area Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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7038 Windham Hill Road Windham VT 05359

Price$339,750

Est. Mortgage: $/month

MLS Number 4767086

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 3
  • Construction Existing
  • Zip 05359

A fine home for all seasons! The house enjoys a fine floor plan with granite, stainless and hardwood flooring. The three acres with swimming pond are beautifully landscaped and an incredible water feature adds special interest and VAST access for those that snowmobile! Entertain friends and family on the multi level deck that takes in the fabulous local views. Windham Vermont is a great location to enjoy all that this area has to offer. Use as home base to ski Stratton, Magic, Bromley, Mount Snow, or Okemo. A shopping excursion to Manchester is sure to please. Golf at Tater Hill is minutes away and hiking is always right outside the door. You won't want to leave this home in the fall when the local hillsides put on their annual festival! This builders home that was taken down to the studs after purchase, the roof was raised and a metal framed addition was added. Anderson perma-shield windows, thick insulated walls and roof, a composite deck and fine cedar siding create an energy efficient envelope. A nice two car garage with large storage above was built and a neighboring property was purchased and the timber frame home was re purposed as a barn. Great storage for all of your equipment and toys! Enjoy neighboring property views that add additional ponds and acres of fields and hillsides to this serene setting!

Listed by Susan LeCours and Jessica Landers of Barrett & Valley Associates, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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2 Route 100 Andover VT 05143

Price$49,900

Est. Mortgage: $/month

MLS Number 4766254

  • Land
  • Acreage 11
  • Zoning RES

Located half-way between Ludlow and Weston, this 11-acre parcel is ready for you! Engineering shows a three-bedroom home can be built. Close proximity to skiing, dining and shops in Ludlow (5 minutes away) or theater, shops and summer recreation in Weston (also 5 minutes away).

Listed by Claudia Harris of Mary Mitchell Miller Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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1989 Andover Ridge Road Andover VT 05143

Price$475,000

Est. Mortgage: $/month

MLS Number 4764793

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 3
  • Construction Existing
  • Zip 05143

Stunning long distant views from the top of Andover Ridge. An architecturally unique property providing awesome views from every room. The open floor plan for the kitchen/dining/living area is the perfect room to entertain family and friends. Amenities include a stone fireplace, wet bar, kitchen island, skylights, and sliders to an expansive deck. The enclosed entryway and 3/4 bath are just off the kitchen area. The 'piece de resistance' is the lovely master suite providing 800 SF of living space. This special retreat features hardwood flooring, a marble fireplace, generous master bath with whirlpool tub, shower and double sink, plus spiral stairs to upper level study. A wall of sliding doors providing sunlight, views and entry to the deck. The upper level includes a guest bedroom and large loft area that doubles as a sleeping space. To feel on top of the world, take the stairs to the roof deck and enjoy your evening cocktail. The lower level has a cozy family room with a pool table, more sleeping space, a wood burning stove and 3/4 bathroom. The laundry room, walkout entryway and attached 2 car garage with extra storage space complete the lower level. Ideally located near the quaint village of Weston making easy access to Okemo, Stratton, and Bromley resorts. Privacy, perennial gardens with an open lower field make this a very special Vermont home. Sold Completely Furnished!

Listed by Meredith Stock and Nancy Jensen of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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1574 Burbee Pond Windham VT 05359

Price$147,500

Est. Mortgage: $/month

MLS Number 4763067

  • Mobile
  • Year Built 1987
  • Bedrooms 2
  • Square Feet 1,050
  • Acreage 4.1

Escape to the country! Great hunting Camp - just in time for the season! Country living in a great location! This four + acre parcel has lovely landscaping, a nice pond and great access. Blueberry bushes, perennials and fruit trees are painstakingly cared for by the owners. This clean Mobile home has recently been upgraded with new Kitchen and baths. Bright and homey inside, ready to move in! There are 3 sheds, 2 are nicely sized wooden garages and the other is a shed for the garden tools! Plenty of room to build a place at the "top of the hill" with access from Windham Hill Road and views of Stratton if desired. There are so many possibilities for this property! Come see it today!

Listed by Alison Clayton-Cummings of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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Gates Andover VT 05143

Price$21,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4761258

  • Land
  • Acreage 3
  • Zoning Residential

This neat 3 +/- acre lot is perfectly situated on a quiet dirt road, yet minutes to many of the area attractions. It has nice easy access off the town maintained road. With some clearing you could park your camper or build your dream home. Come look today. Motivated Seller!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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772 Hilltop Road Andover VT 05143

Price$265,000

Est. Mortgage: $/month

MLS Number 4760616

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05143

Ever dreamed of a life away from it all . . . now is your chance! This adorable and well-maintained log home sits on 3+ acres at the top of Hilltop Road in Andover and enjoys year-round views and close proximity to both Chester and Londonderry (shops, school, etc.) and skiing, golf, hiking and Lowell Lake are all nearby. Enjoy the views and some true peace and quiet from your front porch in the summer, or pull up a chair in front of the cozy fire in the spacious living room come winter. Main level has large living room, separate dining room, kitchen and a bath with shower. Upstairs are three bedrooms and a bath with tub, and the lower level has a rec room and utility area. The cabin is offered fully furnished and is ready to be enjoyed . . . just bring yourselves!

Listed by Claudia Harris of Mary Mitchell Miller Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

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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 September 23, 2019.