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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466 Wheeler Road Windham VT 05359

Price$155,000

Est. Mortgage: $/month

MLS Number 4741358

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

This affordable chalet is conveniently located close to resort mountains but tucked back on a quiet country road on 2.6 wooded acres. Features include 3 bedrooms, 2 1/2 baths, open concept living, dining, kitchen on the main level and a wrap-around deck. There are a few projects underway that need finishing but with a little TLC, this cute and cozy home could really shine. Highly rentable, a great getaway or both! More pictures coming soon...

Listed by Adam Granger of Redbud Real Estate

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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316 Little Pond Road Andover VT 05143

Price$274,000

Est. Mortgage: $/month

MLS Number 4740606

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

Private! Upgraded and Updated Retro! Solid Chalet Home! Acreage to play on! HUGE Deck off the living area with huge sliders that open the space to be all inclusive. Beautiful full sized field-stone fireplace. Close to: Downhill skiing, XC skiing, VAST Snowmobiling, Quaint Village Shopping, dining and culture (Weston Playhouse), THE Vermont Country Store, summer activities, lakes and trails! 8 mins to magic mountain, 15 mins to okemo, 20 mins to stratton, 20 mins to Bromley, 45 mins to killington, 40 min to mount snow. Upgrades include: new septic tank and piping, new heavy gauge Metal roof, professional sealing/caulk/spray foam for better insulation, new Andersen sliding doors, Vermont castings wood stove, kitchen counter tops and appliances, new washer & drier, new crawl space vapor barrier, new mini split unit heat/and AC, water heater. Property Also runs all the way through to Marsh Hill Road.... Subdivision is a possibility if you choose. Room for about 18 snowmobiles under the deck! Turn key and ready to become YOUR Vermont Get-a-way!

Listed by Steve Goldfarb of Hermitage Deerfield Valley Real Estate

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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300 Fairway Meadows Road Windham VT 05359

Price$840,000

Est. Mortgage: $/month

MLS Number 4739427

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 3
  • Construction Existing
  • Zip 05359

If you ever wanted to leave the "rat race" behind and find paradise, serenity and peace and quiet in Vermont... this idyllic spot is for you. It's like having your own resort and special hideaway! Total privacy on 28+ acres with 270 degree views, including the peaks and trails of Okemo in the distance. This fabulously unique timber frame, designed by Pete Newton and built by Scott Wilkins Custom Home Builders will captivate your imagination. What it is and what it could be! Literally 100's of thousand of $$$'s of gorgeous Windham Dark Green Ledge Slate from this very property, makes up the massive and dramatic wood burning fireplaces inside and the slate also lines the huge Vt. country pool/pond and huge patio area. Pool area also with a Vt. timber beam Cabana for entertaining. The home enjoys Southern sunny exposure in all the living areas. Incredible living room, master bedroom and kitchen all flowing out to poolside summer living and splendid mature gardens in bloom. Entertaining is world class with pool table and state of art golf simulator with over 200 courses to test your skills. Just a short distance is Vail's Tater Hill Golf Club and the VAST snowmobile trail has direct link access from the property to enjoy ALL that Vermont has to offer in EVERY season. Magic, Stratton and Okemo all within 25 minutes. Come see this magnificent home and be ready to be wowed.

Listed by Wilkie Bushby of TPW Real Estate

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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2402 Simonsville Road Andover VT 05143

Price$279,000

Est. Mortgage: $/month

MLS Number 4737121

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

Located on a very private 4.5 acres sits this lovely gambrel style home beautifully cared for and loaded with rustic charm. The property features a 2 stall barn with water, electric and a large hayloft. Fenced in pasture and level arena area. All set up and ready to go. There is also a trail system for riding and hiking beyond the property accessible by a neighborly agreement that connects to Little pond Rd, Middletown and Marsh Hill Rd. The house is move in ready and has had many updates over the years including a well, furnace and windows. Renovated kitchen with all new appliances installed in 2017. Granite counter tops and a large island. The living room is all about Vermont. Beautiful custom built stone fireplace that is efficient enough to heat the room and beyond. Perfect for winter nights. The first floor also has an office/den that could be used as a bedroom if needed. The second floor has three ample sized bedrooms including a large master with a balcony. The home also boasts a full length covered back porch to sit an enjoy the serene surroundings. This home and property is truly a gem to be enjoyed year round. Conveniently located directly between Chester and Londonderry. Just minutes to Magic Mountain, Lowell Lake and a short drive to Bromley and Stratton Mountain resorts.

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

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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937 VT RT. 121 Highway Windham VT 05148

Price$79,000

Est. Mortgage: $/month

MLS Number 4730856

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05148

Three bedroom two bath ranch, easy drive to magic mountain ski area , large living room with wood stove hookup, newer kitchen cabinets and flooring.

Listed by John Morrison of Barrett and Valley Associates, Inc

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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19 Harrington Road Windham VT 05359-9626

Price$199,000

Est. Mortgage: $/month

MLS Number 4730330

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05359-9626

Windham Gem! Classic New England cape on a corner-lot with an attached garage. Minutes to Magic, Bromley, and Stratton. Nearby access to the VAST Trail System. Relax by the wood stove insert after a day on the slopes. Living space has views of the church next door or the Green Mountains in the winter. Efficient kitchen has all the comforts of home, with a stove, refrigerator and energy star rated stackable washer and dryer. Main level master bedroom has a private, recently renovated full bathroom. Upstairs two bedrooms share another full updated bathroom. Wood storage shed and furnishings included.

Listed by Andie Fusco and Mary Kate Grey of TPW Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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320 Valley View Drive Extension Andover VT 05143

MLS Number 4730176

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 5
  • Construction Existing
  • Zip 05143

Note: Two listings exist for this property in Ludlow and Andover, MLS #4730489. Located in Summit Ridge, an exclusive gated community 3.5 miles from Okemo Valley Ski Resort, this custom designed 4,732 sq ft all-seasons Bensonwood timber frame home is truly an exquisite property. The house features the finest quality finishes and elegant furnishings in an enchanting Vermont mountain setting. Situated on 16 acres, the house has spectacular, panoramic views of the Vermont and New Hampshire mountains from throughout the home. An open floor plan incorporates 5 bedrooms (3 en suite) and 4.5 baths making the home a perfect location for family gatherings. The property features a large aerated pond with a waterfall and a mountain stream, extensive picturesque landscaping including perennial gardens, flowering fruit trees and wildflower beds. Custom Douglas fir kitchen cabinets adorn a gourmet state- of-the-art kitchen, finished maple floors, designer tile baths and showers, top line appliances, surround sound theater room with sleek 80" screen and three custom stone fireplaces are just a few of the many quality finishes throughout the house. A whole house generator, discrete solar power, which generates electricity equal to the annual house demand and an EV charging outlet in the oversized 2.5 car garage are additional features of this exceptional property. Many more thoughtful features too numerous to mention make this magical home a perfect Vermont country setting.

Listed by Katherine Burns of William Raveis Vermont Properties

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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200 Edson Drive Windham VT 05359

Price$299,000

Est. Mortgage: $/month

MLS Number 4727877

  • Land
  • Listing Agent Name Christiane Carroccio
  • Acreage 100
  • Area Near Golf Course
  • Zoning Land

100 acres in southern Vermont with improvements. Sold subject to current use enrollment. Acreage has been excluded for a single family home with permit in place for a 4 bedroom single family home. Driveway and underground power installed to house site. House site is cleared, lawn mowed, ready to build. Well is drilled. Bring the RV and hook up, then build the house. View from house site, and bigger views on the trails cut throughout the property. Located close to Londonderry, Stratton, Bromley, and all that southern VT has to offer. Distance from Tater Hill Golf Club: 0.5mi Distance from Downtown Chester VT: 8.3mi Distance from Magic Mountain Ski Resort: 5.2mi

Listed by Christiane Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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141 Dorman Road Andover VT 05143-9042

Price$279,900

Est. Mortgage: $/month

MLS Number 4723803

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05143-9042

This pristine 3 bedroom 2 bath ranch sits on just over 4 acres on a quiet road in Andover. After pulling down the driveway, it offers a private and peaceful setting with its own pond, and Trout Brook runs just in back of the property line. If you like to play in the snow, Okemo is a short 8 miles away, and there is also a VAST trail that runs through the very edge of the property line. The current owners have resided here for 20 years and have taken immaculate care of the property and home. Included in the upgrades are a new roof two years ago, and granite countertops in the kitchen. There is plenty of "his and her" space! The main level offers a master suite, 2 other bedrooms, a laundry room, open living/dining room and a beautiful covered three sided screened in porch to enjoy the surroundings. There is a 2 car attached garage where the walls and ceiling are lined in wood that includes power and automatic garage doors. The basement is dry and clean and has a separate workshop room as well as a finished room (that is insulated), and also an attached woodshed that holds 7 cords of wood. This lovely light filled home is turn key and you'll see it has been cared for. This would make a great primary or second home.

Listed by Heather Gleim of Walnut Hill Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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6641 Windham Hill Rd Windham VT 05359

Price$279,000

Est. Mortgage: $/month

MLS Number 4722600

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05359

When you think about a quintessential Vermont property this one checks all the boxes. Completely renovated 1860 cape that captures the essence of it's past while incorporating the modern touches you'd expect. The country kitchen has gorgeous soapstone counter tops with a currently disconnected antique stove as a useful accent piece. Large windows allow for great morning light. The formal Dining Room boasts pine floors and a wood stove. The cozy Living Room features a classic wood burning fireplace and is an ideal spot to gather at the end the day. The house has three bedrooms including a first floor with a shared full bathroom. The second floor has the master bedroom with built-in dressers and master bath with large tile walk in shower. The other bedroom is large enough for multiple guests. The second floor is completed by an office/den that can also double as a guest room. The property is lovely bordered by a year round stream with water falls and a natural dipping pool to cool off on summer days. Surrounded by trees you'll find some perennial gardens and stone walls. Just outside the house is a blue stone patio and hot tub for relaxing. You also have a 2 car garage with a back deck that leads up to a loft space that can be a playroom, studio or just extra storage. Centrally located in the heart of ski country, just minutes to Magic Mountain and close to Bromley, Stratton Mountain and Okemo. Come and take a look at this special home.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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963 North Hill Road Andover VT 05143

Price$350,000

Est. Mortgage: $/month

MLS Number 4721718

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

Perched on a hillside with breathtaking long-distance views to the south and east, this well-designed architectural gem is beautifully finished and turn-key ready for your immediate use and enjoyment. The house is immaculate, has been exceptionally well-maintained and is offered mostly furnished. With tons of natural light and a comfortable layout, the main level features dining and living areas with woodstove, built-in bookshelves and wrap-around windows, a large well-appointed kitchen with new stainless appliances, slate-tiled entry and bathroom. Upstairs are two spacious en-suite bedrooms, including an elegant master suite with a fireplace and sitting/office area and lots of built-ins. With 3.5+/- acres bounded by stonewalls, the land is truly special and will delight in all seasons. Enjoy summer sunrise views with coffee on your covered porch, or stay cozy with a hot drink in front of the fire on chilly evenings. Other features include an adorable artists' studio and a handy oversized one-car garage. Skiing is minutes away, 4-season recreation options abound, Weston is just a couple of miles down the road and the shops and restaurants in Ludlow, Chester, Londonderry and Manchester are all close by.

Listed by Claudia Harris of Mary Mitchell Miller Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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85 Little Pond Road Andover VT 05143

Price$165,000

Est. Mortgage: $/month

MLS Number 4721356

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 1
  • Construction Existing
  • Zip 05143

Wonderful year-round recreational paradise, with VAST trail access, this property is just minutes to Lowell Lake, Tater Hill Golf Course, the town of Weston as well as Okemo, Magic, Bromley, and Stratton Mountains! Spacious and open living, kitchen, and dining room with wood stove creates the perfect atmosphere to relax after a day of fun! The current owners have made many recent upgrades to the property including a renovated master bedroom and bath, insulation, and front porch to name a few. This home sits on over 2 acres of mostly cleared land but is still nestled in the woods! ¼ mile to VAST trail marker WR55. This home is a must see!

Listed by Carrie Mathews of William Raveis Winhall

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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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 March 24, 2019.