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 Josiah Allen today for more information and to schedule a tour. Learn more about the Chester Area!

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3128 Windham Hill Road Windham VT 05359

Windham, VT3128 Windham Hill Road

Price$150,000

Est. Mortgage: $/month

MLS Number 5005075

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

Historic mid 19th century cape in the south hamlet of Windham being sold as is. Current owner has begun renovating, but there is still plenty left to do. There is a brand new boiler in the basement, but is presently not connected. This is a lovely location at the south end of town with ready access to local ski areas including Magic, Stratton, Bromley and Okemo, and close proximity to Jamaica State Park, West Townshend General Store, Londonderry Farmers Market and local shopping.

Listed by Christopher Cummings of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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2358 North Hill Road Andover VT 05143

Andover, VT2358 North Hill Road

Price$475,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5002998

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

A once in a lifetime opportunity to own this unique property in the picturesque Vermont town of Andover! This home sits on 5 wooded acres. It is 12 minutes from Okemo Resort, as well as being close to Magic, Bromley and Stratton Resorts. It is also just a short snowmobile ride to the VAST trail. The property consists of a main house, built in 1972, as well as an attached in-law apartment and garage built in 2002. The main house has 3 bedrooms and 2 bathrooms and 2 fireplaces. Lovely cathedral ceilings on the second floor with an open concept living and dining room and a galley kitchen. The main house boasts 2 decks, one connecting the first floor bedrooms and another off the living room. The in-law apartment has 1 bedroom and 1 bathroom and a kitchen and living room. This would make a wonderful retreat for family and friends as well as an amazing investment property! This property is a rare gem, come and take a look!

Listed by John Napier and Karen Wilson of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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2253 White Road Windham VT 05359

Windham, VT2253 White Road

Price$725,000

Est. Mortgage: $/month

MLS Number 5002967

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

Stunning acreage surrounds this charming home in Windham, Vermont. A quintessential get-away with a large screened-in porch overlooking the waterfall and pond. Follow the bridge across the pond to the meadow and trails. The extensive trail network is well maintained, meandering throughout the 110 acres. Enjoy all seasons of exploring! The bungalow style house was completely redone in 2001. The light colored wood floors enhance the light, open layout which includes 2 bedrooms and 2 bathrooms. A soapstone wood stove in the sitting area gives promise of cozy winter days. The basement has high ceilings and a garage door, most recently housing the John Deere that was used around the property. Find extra storage in the small barn. The acreage has been maintained with great care. There is a park-like wooded area just across the road, making the view from the front porch very tranquil. With skiing at Okemo, Bromley, Magic, Stratton and Mount Snow only 20 minutes away, dining in Grafton, Weston and Chester in minutes and theater near-by, find year-round entertainment on this very special property.

Listed by Alison Cummings of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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599 Hitchcock Hill Road Windham VT 05359

Windham, VT599 Hitchcock Hill Road

Price$589,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5002926

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

Sunlight pours in to this charming log home in Windham. It is exceptionally well sited to take advantage of the landscape, exposure and view. Many large south facing windows allow for ample light inside and the large deck that surrounds the home extends the living space to outside. Discover the space in between, a large sun room just off the living area, perfect for enjoying the sunset year round. Enter through the mudroom and into an open concept kitchen and dining area. Take in the cozy atmosphere with soaring ceilings and warm wood tones throughout. In the living room enjoy a fire in the wood burning fireplace. This thoughtful layout includes 3 bedrooms, one on each level. The ensuite on the top floor opens to a loft area for extra sleeping or an office. The nicely sized main floor bedroom has an adjacent bath. This great home on 14+ acres has direct trail access to VAST trails. The land is filled with wild berry bushes and a hidden stream complete with a waterfall. All of this is within a short distance to year round recreation including farmers markets, summer theater, 5 local ski areas and so much more of what Vermont offers. Call for a showing today!

Listed by Alison Cummings of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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26 Dorman Road Andover VT 05143

Andover, VT26 Dorman Road

Price$415,000

Est. Mortgage: $/month

MLS Number 5002282

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

This classic style four- bedroom chalet on 2.1 acres in Andover has been "a joy" to the owners who have had this property for over 40 years. It has been well maintained by them and their local caretakers. As a second home, it is being sold fully furnished and "as is". There are two bedrooms on each floor. This quintessential chalet has an entry level front porch as well as a top floor deck for relaxing and enjoying the view. Kitchen and dining areas are on the first floor with main living room and family room located on the top floor. High speed fiber optics internet is provided by VTel. Perfectly located for the skiing and outdoor enthusiast. Just a short drive to any of 4 local ski areas (Magic, Stratton, Okemo and Bromley). Of course, hiking, fishing, biking, golfing and swimming opportunities abound in the area. The VAST trail is also not far away with a number of entry points in Andover and Weston. The friendly and caring town of Andover with approximately 500 residents provides easy access to the special and famous village of Weston, area restaurants, the Weston Playhouse and Walker Farm, and country stores. ENJOY VERMONT !!!!

Listed by Chuck Sweetman of Mary Mitchell Miller Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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7406 Windham Hill Road Windham VT 05359

Windham, VT7406 Windham Hill Road

Price$795,000

Est. Mortgage: $/month

MLS Number 5001885

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 4
  • Construction Existing
  • Zip 05359

Designed with an open layout, this contemporary farmhouse is awash with natural light. The chef's kitchen features local Danby Marble countertops and ample built-in storage. The soft patina of Ash wood floors are a highlight throughout the entire home. Built in 2008, with a custom interior completed in 2016, it includes two spacious en-suite bedrooms and a third bedroom with a dedicated bath and private sitting area. Additionally, there's a gym space for your fitness needs. The living room boasts nine-foot ceilings and a highly efficient fireplace that warms the entire home. The heated two-car garage, with elegant wood paneling, has hosted dinners for up to 40 guests. Above the garage is a versatile heated space, ideal for an office or studio. Whole house A/C. The fenced backyard, surrounded by hydrangeas, features a large deck and fire pit, perfect for gatherings and romping children and dogs. A dedicated storage barn offers space for gear, with a direct connection to the VAST trails, allowing snowmobile access to local dining spots such as the Townshend Dam Diner. At the base of Timber Ridge Mountain, this turn-key property is close to skiing, farmers markets, and local summer theater. Enjoy Friday pizza nights at the West Townshend Country Store, farm-to-table dining at SoLo or the Grafton Inn, and excursions to the Southern Vermont Arts Center. 5-7 miles from Magic Mt. and Viking Nordic Center and 14-18 miles to Bromley and Stratton. 2:45 hrs to Boston. 4:15 hrs to NY

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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81 Trombley Road Andover VT 05143

Andover, VT81 Trombley Road

Price$275,000

Est. Mortgage: $/month

MLS Number 5001000

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

This beautiful privately located 3 bedroom, 2 bathroom manufactured home is move in ready and just waiting for your finishing touches! It has a wonderful level yard with plenty of space for gardens, room to play, or put in a camp fire to sit around on a lovely Vermont evening. There is an additional gravel pad in place that you could put a tiny home as a rental opportunity or a guest house when company comes to visit. You can use the drilled well for both house and the tiny house you add. There is also an approved septic design in place if you choose to add a tiny house there. Other great features are a 30 x 60 hoop building with lots of storage space and another shed with even more storage potential! Would make a great first home, family home, home for someone looking to downsize, or so many other options! Call to schedule your appointment today! Agent is a relative of seller.

Listed by Erin Kendall of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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3011 A East Hill Road Andover VT 05143

Andover, VT3011 A East Hill Road

Price$698,000

Est. Mortgage: $/month

MLS Number 5000737

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

This gracious country contemporary, on the market for the first time, was designed and finished by its longtime owners, an industrial designer and an interior designer. Beautifully sited in a landscaped setting on a quiet country road, it enjoys distant mountain views and is protected on all sides by woods with nature trails. The 3 bed/3 bath interior is light and airy with plenty of living and working space including a bonus room used as a bunk room and unfinished space on the top and bottom floors allowing further expansion. There are distinctive and stylish touches exhibiting quality workmanship throughout, including floating stairs, custom built-ins, mahogany paneling in the open concept living/dining room, Saint Charles cabinets in the kitchen, a Rumford fireplace built with vintage bricks, a whirlpool tub, sauna, a workshop space and a darkroom that could be an artists studio or home office. Outdoor living possibilities abound with a wrap-around deck, fire pit, lush gardens and a designer-built shed. Peaceful and private, the property is located just minutes by car from Okemo Mountain and Ludlow's shopping amenities and, in the other direction, from Weston's theater, cafes and The Vermont Country Store. The property is also being offered without the undeveloped land parcel across the road; see MLS 5000110. Come see it in person and discover the many distinctive qualities of this much loved home. All measurements approximate.

Listed by Steve Stettler of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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3011 East Hill Road Andover VT 05143

Andover, VT3011 East Hill Road

Price$615,000

Est. Mortgage: $/month

MLS Number 5000110

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

This gracious country contemporary, on the market for the first time, was designed and finished by its longtime owners, an industrial designer and an interior designer. Beautifully sited in a landscaped setting on a quiet country road, it enjoys distant mountain views and is protected on three sides by woods with nature trails. The 3 bed/3 bath interior is light and airy with plenty of living and working space including a bonus room used as a bunk room and unfinished space on the top and bottom floors allowing further expansion. There are distinctive and stylish touches exhibiting quality workmanship throughout, including floating stairs, custom built-ins, mahogany paneling in the open concept living/dining room, Saint Charles cabinets in the kitchen, a Rumford fireplace built with vintage bricks, a whirlpool tub, sauna, a workshop space and a darkroom that could be an artists studio or home office. Outdoor living possibilities abound with a wrap-around deck, fire pit, lush gardens and a designer-built shed. Peaceful and private, the property is located just minutes by car from Okemo Mountain and Ludlow's shopping amenities and, in the other direction, from Weston's theater, cafes and The Vermont Country Store. The property is also listed including the undeveloped 5 acres across the road - see MLS 5000737. Come see it all in person and discover the many distinctive qualities of this much loved home. All measurements approximate.

Listed by Steve Stettler of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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1337 Andover Ridge Road Andover VT 05143

Andover, VT1337 Andover Ridge Road

Price$1,550,000

Est. Mortgage: $/month

MLS Number 4999325

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

Meticulous and spacious home that has been thoughtfully and lovingly updated on the prestigious Andover Ridge Road. Overlooking the Green Mountain National Forest and the village of Weston, this beautiful custom-built 4800+sf log home exudes privacy, warmth, comfort and charm. The kitchen has heated stone flooring, abundant light and breathtaking views. There are two spacious living areas currently set up with two bedrooms on each level, a library with custom cabinetry, a loft for additional space, a well appointed home gym and three full baths. The amazing 1200+sf two-tiered mahogany deck is ideal for entertaining and enjoying the sunsets over the mountain range. Or relax in the hot tub while listening to the premium outdoor sound system. The new gazebo provides additional serenity and picturesque views, complete with windows, a sound system and Wi-Fi - allowing you to redefine “working remotely”. This one of a kind 6+ acre property abuts 2000 acres of protected State Forest. Centrally located within 25 minutes of Okemo, Stratton, Bromley, Magic and just a few minutes from Weston. Embrace all that this property has to offer: fresh air, peaceful days, great skiing, hiking, golf, the iconic Weston Playhouse, local shopping & restaurants all right outside your door. This stunning craftsman's home has been updated with a new roof, central a/c, hardwood floors in the primary suite and new carpeting downstairs as well as many other fine finishing touches.

Listed by Liz Moore and Sean Dillon of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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2181 White Road Windham VT 05143

Windham, VT2181 White Road

Price$999,000

Est. Mortgage: $/month

MLS Number 4998938

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 2
  • Construction Existing
  • Zip 05143

Nestled along a serene country road, this enchanting home exudes rustic charm and timeless elegance. The “Twin Brooks” that flank the property and private pond round out the much desired water features. Hand hewn beamed ceilings welcome you into a cozy haven where every detail tells a story. Adorned with captivating features, the interior boasts a marble-faced fireplace, a soapstone stove radiating warmth and comfort, wood flooring, transitional lighting and a hand painted mural. Delightful granite countertops adorn the kitchen, complemented by a Viking range and solid antique butcher block. The primary bedroom offers a tranquil retreat with its own fireplace and displaying a whimsical contrasting of crystal chandeliers poised below the rusty touched metal ceiling. The antique barnwood too evokes a sense of the history embedded in this mid 19th century homestead. Many outdoor living spaces including a hot tub oasis and a patio with a fire pit are perfect for gatherings under the stars. Deep fieldstone walls by Dan Field frame the home and meadows while old pines and maple trees line the landscape. A three-car garage, workshop and sheds provide ample space for projects. All of this is surrounded by lush perennials and breathtaking hill vistas! The field of sunflowers, a chicken coop, raised beds and greenhouse give homage to the farm. This home is a sanctuary where modern comfort meets rustic allure, offering a peaceful retreat for those who cherish the beauty of nature.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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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00 Marsh Hill Road Andover VT 05143

Andover, VT00 Marsh Hill Road

Price$4,000,000

Est. Mortgage: $/month

MLS Number 4998559

  • Land
  • Acreage 506
  • Utilities None
  • PricePerSqFt 7905.14
  • Zoning Unknown

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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 2024 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 July 23, 2024 8:08 PM EDT