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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2267 North Hill Road Andover VT 05143

Andover, VT2267 North Hill Road

Price$159,000

Est. Mortgage: $/month

MLS Number 4996583

  • Land
  • Acreage 2.4
  • Area Rural
  • PricePerSqFt 66250
  • Zoning residential

A rare opportunity to own a slice of Vermont! This picturesque property sits on 2.40 acres in Andover most of which is level land. There is a garage/camp which was built in 2013, with a 200 amp electrical service, with a loft above, the loft has a deck off the back. The property has a drilled well and a 2 bedroom wastewater permit in place as well as a fire pit and a shed for storage. It sits on a quiet and rural road. This would be a perfect spot to build your dream or vacation home, or make a wonderful camp. It is treed and provides privacy yet is close to the VAST snowmobile trail and only 6.5 miles from the Ludlow village and Okemo Resort. Come and see for yourself!

Listed by John Napier and Karen Wilson of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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2401 North Hill Road Andover VT 05143

Andover, VT2401 North Hill Road

Price$795,000

Est. Mortgage: $/month

MLS Number 4996543

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

With an excellent layout, special features and prime location, this four bedroom, two and a half bath cape in Andover is a must see! It sits on 4+ acres of manicured grounds with a babbling brook running through the property. Situated between quintessential Weston and the action of Ludlow, it is easy to access, a peaceful setting surrounded by a natural Vermont landscape. The area is host to winter recreation, summer theatre, waterfalls and hiking trails, all ready for your enjoyment. Discover over 2900 square feet of remarkably finished living space. A chef's kitchen with ample room for entertaining opens out to a lovely patio. The primary suite on the main floor has a walk-in closet and radiant heat in the private bath. Adjoining the primary suite is a screened porch with a large round hot tub, overlooking the beautiful backyard. Large windows take full advantage of the surrounding landscape, including a silhouette of a pretty ridge line at the end of the meadow. Recent upgrades include a solar array and a stand by generator. Say goodbye to pricey electric bills! Vermont Association of Snow Travelers (VAST) trails are easy to access, no trailer needed. Large under-story of garage has direct entry for recreation vehicles. This home is being sold nicely furnished. Move right in and start enjoying this Vermont mountain oasis and all it has to offer. Make a date to see it today!

Listed by Alison Cummings of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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1749 Middletown Road Andover VT 05143

Andover, VT1749 Middletown Road

Price$359,000

Est. Mortgage: $/month

MLS Number 4995283

  • Land
  • Acreage 31
  • Utilities Gas - LP/Bottle
  • PricePerSqFt 11580.65
  • Zoning res

Tucked away on 31 beautiful acres in Andover is this lovely camp, cottage ready to be finished and enjoyed. The current owners have provided a great start with electric service, forced hot air heat and a finished living room to relax in. The land is a nature lover's dream with a year round stream in back of the camp, open area with a firepit and surrounded by a vast variety of trees on the mostly wooded acreage. The long driveway approach gives you a true sense of a cabin in the woods retreat. The addition of a septic system and well, could make this potentially a year round home. Fantastic location on Middletown Rd. Just minutes to center of Weston where you'll find the Vermont Country Store, excellent dining and the historic Weston Playhouse. Near several major ski resorts, Okemo, Magic, Stratton and Bromley Mountain. This is truly a find that offers the best of the Vermont experience.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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1749 Middletown Road Andover VT 05143

Andover, VT1749 Middletown Road

Price$359,000

Est. Mortgage: $/month

MLS Number 4995277

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

Tucked away on 31 beautiful acres in Andover is this lovely camp, cottage ready to be finished and enjoyed. The current owners have provided a great start with electric service, forced hot air heat and a finished living room to relax in. The land is a nature lover's dream with a year round stream in back of the camp, open area with a firepit and surrounded by a vast variety of trees on the mostly wooded acreage. The long driveway approach gives you a true sense of a cabin in the woods retreat. The addition of a septic system and well, could make this potentially a year round home. Fantastic location on Middletown Rd. Just minutes to center of Weston where you'll find the Vermont Country Store, excellent dining and the historic Weston Playhouse. Near several major ski resorts, Okemo, Magic, Stratton and Bromley Mountain. This is truly a find that offers the best of the Vermont experience.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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 Simonsville Road Andover VT 05143

Andover, VT00 Simonsville Road

Price$69,000

Est. Mortgage: $/month

MLS Number 4994121

  • Land
  • Acreage 3.99
  • Utilities Cable - Available
  • PricePerSqFt 17293.23
  • Zoning Res

3.99 +/- acre parcel with VT State approved Wastewater Permit for a four bedroom single family home along the Williams River in the Historic Simonsville settlement of Andover, Vermont. A tiny home would work well on this lot or a mobile home as there are no building restrictions. Or use recreationally with an RV for seasonal vacations. Driveway is roughed in with culverts and power is at the road. Level, elevated building area outside the flood zone and within an easy drive to ski areas, lakes and trails for kayaking and hiking. A good base camp for cycling and mountain biking enthusiasts. Come explore this land which has nearly 1000' of frontage. Adjoining house and acreage also available. See mls #4994070.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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566 Simonsville Road Andover VT 05143

Andover, VT566 Simonsville Road

Price$599,000

Est. Mortgage: $/month

MLS Number 4994070

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

The historic Jaquith House is located in the Andover settlement of Simonsville. This outstanding brick federal 3 bedroom, 2.5 bath home on 6.85 +/- acres has potential for either a vacation home with guest house, year round residence or investment property. The two story double-walled brick home has original features such as eyebrow windows and 4 chimneys and has been thoughtfully updated with modern amenities such as first floor radiant heat, central air and a chef's kitchen with a professional 48" Dacor range with double ovens, attractive arched, brick hearth complimented by cherry cabinets, walk-in pantry and attractive island and curly maple counters. Period details have been carefully attended to with custom interior shutters, replacement windows, a Monson slate roof, preserved softwood pine floors, clawfoot tub, custom copper top vanities/sinks and three fireplaces. A walk-up attic offers additional space to finish. A detached two bay post and beam garage adds both character and utility with oversized doors for RV use. The quaint "kissing bridge" serves as a woodshed and an auto generator adds peace of mind. A screen house by the river is a bonus feature. Two barns, original mill stones and a historic logging road tell the story of this property's history along the Williams River for over 200 years. 6.85 acres includes a 3.49+/- acre lot w/state approved wastewater permit for 4 bedroom home. Adjoining 3.99 acre lot available see mls 4994121.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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121 Windham Springs Road Windham VT 05359

Windham, VT121 Windham Springs Road

Price$289,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4994046

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 2
  • Construction Existing
  • Zip 05359

What a location! This great get-away has been loved by one family for a very long time and they are now ready to pass it on to the next owners! Large windows bring in the light and make you feel like you are in a treehouse! Slate floors and warm woodwork give this home a rustic, comfortable feel. The open concept floor plan on the main level allows for a variety of options in how the living space is laid out. There are 4 bedrooms and 1 bath on the second floor with 2 smaller bedrooms on the 3rd floor. Windham is centrally located and is in close proximity to Magic Mountain, Bromley, Stratton, Mount Snow and Okemo for winter recreation as well as a short drive to Weston, Grafton and Chester. Don't miss this one!

Listed by Alison Cummings of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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224 Arrau Road Andover VT 05143

Andover, VT224 Arrau Road

Price$179,000

Est. Mortgage: $/month

MLS Number 4993637

  • Land
  • Acreage 8.53
  • PricePerSqFt 20984.76
  • Zoning res

If you are looking for the perfect location to build your Vermont home look no further than this wonderful Andover lot in the green mountains. The best of all worlds is right here. Privacy and seclusion just a short drive to the towns of Weston, Chester and Londonderry. The 8.5 acres has been cleared and is ready to build. Driveway is in place along with a drilled well and septic design for a 4 bedroom home of your choosing. Plenty of cleared acreage for outbuildings and barn if you are looking to have horses or animals. Location is also ideal for the outdoor enthusiast with hiking, snowmobiling, mountain biking, hunting and close proximity to several major ski resorts including, Okemo, Magic, Stratton and Bromley. Come and create your Vermont dream home and experience.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

East Hill Road Andover VT 05143

Andover, VTEast Hill Road

Price$110,000

Est. Mortgage: $/month

MLS Number 4991504

  • Land
  • Acreage 5
  • Area Rural
  • Utilities Telephone Available
  • PricePerSqFt 22000

This is a great spot...easily accessed from Ludlow if you are looking to be near the recreation offerings. Just under 7 miles to Okemo. Weston isn't far, and neither is Chester! This is a handsome wooded lot that slopes up from the road. Almost 1000 feet of road frontage so you can choose where you want to locate your house-site. The property is mostly hardwoods. You can choose if you want to clear to really open your views, or do you want to keep the privacy. You will have neighbors, but you will barely see only one house from your house-site. There aren't many opportunities like this one, don't miss out!

Listed by Betty McEnaney of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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Howard Hill Road Andover VT 05143

Andover, VTHoward Hill Road

Price$1,750,000

Est. Mortgage: $/month

MLS Number 4990472

  • Land
  • Acreage 297.52
  • PricePerSqFt 5881.96

You've got creative visions - We've got your canvas Immerse yourself in the tranquility of nature as you explore the mature maples,ponds, meadows, stone walls and vista views of this remarkable 200.27-acre property. Whether you're seeking a private retreat, an investment opportunity, or your dream home, this property offers the perfect blend of natural beauty, seclusion, and potential. The possibilities are endless. Don't miss your chanceto own a piece of Vermont's pristine landscape. Schedule a viewing today and let your imagination take flight!

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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173 Horsenail Road Windham VT 05359

Windham, VT173 Horsenail Road

Price$215,000

Est. Mortgage: $/month

MLS Number 4990434

  • Land
  • Acreage 36.25
  • Utilities Cable - At Site
  • PricePerSqFt 5931.03

Over 35 acres with more than 2,500 feet of PRIME ROAD FRONTAGE on Vermont Route 11, a major east west corridor from Springfiled to Manchester. This open level lot is a perfect spot for your business starting from the ground up. With great exposure and easy access to Route 91 and Vermont Route 7 this ultimate location is waiting for you and your ideas.

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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Howard Hill Road Andover VT 05143

Andover, VTHoward Hill Road

Price$1,200,000

Est. Mortgage: $/month

MLS Number 4990111

  • Land
  • Acreage 200.27
  • PricePerSqFt 5991.91

You've got creative visions - We've got your canvas Immerse yourself in the tranquility of nature as you explore the mature maples, ponds, meadows, stone walls and vista views of this remarkable 200.27-acre property. Whether you're seeking a private retreat, an investment opportunity, or your dream home, this property offers the perfect blend of natural beauty, seclusion, and potential. The possibilities are endless. Don't miss your chance to own a piece of Vermont's pristine landscape. Schedule a viewing today and let your imagination take flight!

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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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 May 23, 2024 8:24 PM EDT