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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700 Weston-Andover Road Andover VT 05143

MLS Number 4953335

  • Land
  • Acreage 3.3
  • Area Village
  • Utilities Other
  • Waterfront 415

Located in the center of Andover, this 3.3+/- acre parcel is all set and waiting for your Vermont adventure. The land is mostly open with some wooded areas along the edges, completely level, and enjoys all-day sun and attractive gentle mountain views. There is over 400 feet of frontage on the Andover Branch of the Williams River, and the house site sits above the river but affords accessibility and the quintessential sound of your own babbling brook year-round. An application has been filed for a 5-bedroom wastewater permit (anticipated early summer 2023). This property is situated just 6 miles from the villages of Weston or Chester (shops, restaurants, theater/music and more), 8 miles to Magic Mountain and about 15-25 minutes to Okemo, Bromley or Stratton for skiing and snow sports galore! The 911 address number will be assigned once a driveway permit application has been approved, but it is in the neighborhood of 700 Weston Andover Road and plugging that into your GPS will get you to the site.

Listed by Claudia Harris of Mary Mitchell Miller Real Estate

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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506 Andover Ridge Road Andover VT 05143-5500

Andover, VT506 Andover Ridge Road

Price$635,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4952873

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05143-5500

Look no further for your true Vermont experience! High atop your private drive is your mountainside retreat. Enjoy your morning coffee on the covered porch overlooking magnificent panoramic views. This unique post and beam constructed by a well known builder invites you to a relaxing casual atmosphere of luxury with low maintenance. The first floor boasts of high ceilings, natural wood beams, open kitchen with large antique island, walk in pantry and granite countertop. Relax in the living room, work remotely from the office space designed for two! Up the open staircase the second floor has wide plank flooring throughout, vaulted ceilings, beams and more amazing views. Here you will find a large landing area inviting you to the three bedrooms and bath. Outside you will find everything you need to relax by the stone fire-pit and put something on the grill. Enjoy your outside shower while taking in the vistas. Take advantage of a hike on your own personal trails. The barn/garage located at the entrance to the property is well prepared for its next owners with heat, AC, electricity and rooms upstairs! Location is a must! While you are up on the ridge you are minutes from the Okemo State Forest, and the quintessential Vermont village of Weston. Only a short drive to Ludlow, Okemo, Bromley and Magic Mountains! Make this your special place in Vermont! By appointment only, no drive-bys please.

Listed by Sandy Laserte of Berkshire Hathaway HomeServices Stratton Home

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%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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Route 100 Andover VT 05143

Andover, VTRoute 100

Price$199,000

Est. Mortgage: $/month

MLS Number 4949155

  • Land
  • Acreage 12
  • Zoning res

Don't miss this incredible opportunity to own 4 subdivided lots that total 12 acres, only 7 minutes down the road from Ludlow and Okemo Mountain! Located right on State Route 100 (easy access and constant plowing), this gorgeous property has a small brook running through it (not near the build sites) and borders both Weston and Ludlow. Also, there is over 1400 acres of the Okemo State Forest right across the street from this lot!! The location is truly unbeatable: less than 10 minutes away from Okemo Mountain and the bustling town of Ludlow, less than 30 minutes from Killington and Stratton mountains, literally across the street from a National Forest, 2.5 hours from Boston, and under 4 hours to NYC. Ready to build your dream home or rental property? The work has been done for you! This property comes with a town approved (4/4/23) Major Subdivision permit, along with engineered wastewater permits for (2) 4-bedroom septics. Survey and engineered plans include FOUR(!) separate home sites, each one with plenty of flat, dry, and buildable land complete with and road plans. The property was also previously engineered for a single large home + septic too. With electric hookup directly at the street, this property couldn't be more ready to build your dream home(s!). Sellers are also open to providing fully engineered house plans done in modern Scandinavian styling. Perfect for an investment, family compound, or anything you can imagine!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

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%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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5852 Windham Hill Road Windham VT 05359

Windham, VT5852 Windham Hill Road

Price$675,000

Est. Mortgage: $/month

MLS Number 4945838

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 5
  • Construction Existing
  • Zip 05359

A quintessential colonial Vermont home situated on 6.5 lovely acres with distant ridgeline views, located in the quaint town of Windham. Built in 1910 with an addition completed in 2000, this impeccably maintained 4,000 sq. ft., four bedroom, five bath home, featuring on the main level a large, bright and airy great room with a wood burning fireplace, custom built-in shelves and wood beams adorning the high ceilings. An office/library, breakfast nook, kitchen, dining room, family room with an additional fireplace, and primary bedroom with ensuite and laundry room. The second level has another primary bedroom with ensuite, two additional bedrooms and a bathroom. The full basement is appr. 1,100 sq. ft. There is an attached 2 car garage and additional bay for all your outdoor toys as well as a potting shed for anyone with a green thumb! Beautiful perennials gardens are spread throughout the pastoral grounds. There is an outdoor shed for additional storage and a house generator for the rare occasion of a power outage. In the winter, enjoy snowshoeing or cross country skiing out your back door, or just a short drive to the local ski areas of Stratton, Mount Snow and Okemo. Summer activities such as hiking, biking, swimming, kayaking, and golf, not to mention the spectacular fall foliage, this property's location is ideal for year-round enjoyment. If you are looking for a peaceful retreat that exudes Vermont country living, look no further!

Listed by Patricia Fitzpatrick of Skihome Realty

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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$220,000

Est. Mortgage: $/month

MLS Number 4943835

  • Land
  • Acreage 8.53
  • 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

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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1114 Abbott Road Windham VT 05359

Windham, VT1114 Abbott Road

Price$45,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4943968

  • Land
  • Acreage 1.56
  • Utilities None
  • Zoning residential

Pretty country road located, small stream runs along the front left corner of the property, pretty stonewall and surrounded by neighboring open meadows. There was once a sweet small very primitive 24x24 camp built on log piers on this property that was connected to the well and a septic tank. The camp was removed several years ago, no information or representation on the condition of the well and/or location of the septic tank. No soils testing has been done. This is a sweet country location, come check it out!

Listed by Monique White of Deerfield Valley Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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48 Lee Way Andover VT 05143

Andover, VT48 Lee Way

Price$695,000

Est. Mortgage: $/month

MLS Number 4943322

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

Andover is quintessentially Norman Rockwell. In the summer, county fairs and fried dough line the streets. In the winter, snow is measured in feet. This gorgeous country cape has been renovated top to bottom with meticulous detail, Brand new maple flooring, all new interior paint, new tiling, new furnace, new light fixtures, new kitchen appliances, new washer and dryer, new Master bath, even the door knobs and hinges all match. Every detail was taken into consideration. A granite hearth with gas fireplace centers the home with bright beautiful sunlight pouring in from every side. An artisan's touch can be found in the Vermont Stone centered in the fireplace; an example of impeccable detail. If you are looking for a home that would be great for solar, this home is southern-facing and gets passive sun all day long. You will never be “out in the sticks” because this home has high-speed fiber internet at 1000 mbs. With that speed, it can easily become a smart home that you control from your phone. Even your car will feel like a Bentley in the attached, heated garage with direct entry. This home has a first floor bedroom, a large second bedroom upstairs, and a master suite. There is also a huge bonus room above the garage with its own 3/4 bath. Perfect for a guest or as a rental for additional income. The Buderus furnace and updated systems keeps this home warm & efficient. Don't sleep on this home, it will not last!

Listed by Kate Barry of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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1035 VT Route 121 Windham VT 05359

Windham, VT1035 VT Route 121

Price$655,000

Est. Mortgage: $/month

MLS Number 4942548

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 5
  • Construction Existing
  • Zip 05359

Primary or vacation retreat, this four-bedroom 4 bath home sitting on 17 acres. The open concept allows for large gatherings. The main level features a large living room with cathedral ceiling and fireplace and hardwood floors , an open sitting area, dining room and large kitchen for the chef. Second level has an en-suite and two more bedrooms, 3rd level being finished as well, a great hang out room. The lower level has its own separate entrance, can be use as it own living quarters, with living room full kitchen, 2 baths, bedroom, 2 laundry ares, and extra rooms. Nice yard meadow with a pond and stream, wooded back yard. Within 20 minutes of 4 resorts for skiing and close to the vast trail the the snowmobiler. Come enjoy . Shoes off at showings please

Listed by Michael England of Michael England Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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1834 Simonsville Road Andover VT 05143

Andover, VT1834 Simonsville Road

Price$499,000

Est. Mortgage: $/month

MLS Number 4939589

  • Residential Single Family
  • Bedrooms 8
  • Bathroom 9
  • Construction Existing
  • Zip 05143

Rowell's Inn (1826) located in the village of Simonsville in Andover, Vermont is a transitional Federal style building built in 1826 by Edward L. Simons, the village's namesake. Its most prominent feature is a three-story Connecticut River Valley porch with a recessed arched opening fronted by a square baluster railing. Above this opening “SIMONS VILLE” is painted in black lettering. The Inn was originally a stagecoach stop and was variously used as a community meeting place, post office (1826-1950) and a general store. It was purchased in 1910 by Frederick Rowell who gave the building its current name. The building was updated with Queen Anne details, likely at this time, including colored glass double-leaf doors and two-over-two windows. Today it stands as a thriving family business after recently being saved for future generations to adore. After many updates and improvements, this property now features 6 Ensuite bedrooms, 2 receiving rooms, a cozy bar, a kitchen, and dining rooms that all of which could easily be configured into a stunning family home, outdoor activity clubhouse, and many more uses besides. Additionally, there is a one-bedroom apartment AND attached partially finished space for retail, office or studio! Close to Skiing, VAST trails and all that the green mountains have to offer this property holds tremendous potential whether you are looking for an ongoing business concern or a spacious and historic family home!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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1834 Simonsville Road Andover VT 05143

MLS Number 4939588

  • Commercial
  • Year Built 1820
  • Square Feet 6,034
  • Acreage 1.29

Rowell's Inn (1826) located in the village of Simonsville in Andover, Vermont is a transitional Federal style building built in 1826 by Edward L. Simons, the village's namesake. Its most prominent feature is a three-story Connecticut River Valley porch with a recessed arched opening fronted by a square baluster railing. Above this opening “SIMONS VILLE” is painted in black lettering. The Inn was originally a stagecoach stop and was variously used as a community meeting place, post office (1826-1950) and a general store. It was purchased in 1910 by Frederick Rowell who gave the building its current name. The building was updated with Queen Anne details, likely at this time, including colored glass double-leaf doors and two-over-two windows. Today it stands as a thriving family business after recently being saved for future generations to adore. After many updates and improvements, this property now features 6 Ensuite bedrooms, 2 receiving rooms, a cozy bar, a kitchen, and dining rooms that all of which could easily be configured into a stunning family home, outdoor activity clubhouse, and many more uses besides. Additionally, there is a one-bedroom apartment AND attached partially finished space for retail, office or studio! Close to Skiing, VAST trails and all that the green mountains have to offer this property holds tremendous potential whether you are looking for an ongoing business concern or a spacious and historic family home!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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

445 Wheeler Road Windham VT 05359

Windham, VT445 Wheeler Road

Price$199,000

Est. Mortgage: $/month

MLS Number 4938853

  • Land
  • Acreage 22.25
  • Utilities Telephone At Site
  • Waterfront 1000
  • Water View

The sellers have decided to relocate and that makes you the winner! Here is 22.5 surveyed acres on a town-maintained gravel road. The house site is along the road and then you have 22 more acres of wooded land that will give you room to hike, snowshoe, hunt and gather wood for a lifetime for your fireplace. But that's not the best part. Wait until you see the stream that is beckoning you. It is the nicest brook that I have ever seen. You can hop in the little swimming hole or maybe even toss a line in and come up with a fish! That's not all. So much has been done to get this ready to build. The site has been cleared. The drilled well is in. The septic system has been designed. And best of all, the foundation is in. The sellers were going to build a reproduction cape with an ell off the back. They even went so far as to add a shelf to the foundation so that the visible base could be faced with brick or stone as if it was built in the 1800's. The good news is you can create whatever you want on this foundation. The location is great. You are right around the corner from Burpee Pond for paddling. You would be just up the road from the West Townshend store. Magic, Bromley and Stratton are close by. Okemo, Mt Snow, and Killington aren't that far either. The VAST trail is just up the road for snowmobiling. If you haven't found the house you want maybe the time is right for you to build your own!!

Listed by Betty McEnaney of Bean Group / Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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441 Markham Mountain Road Andover VT 05143

MLS Number 4931340

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

Looking for a Vermont retreat that everyone in your family will enjoy then look no further!!! This well constructed 4 season camp perched on a 10 acre mountainside parcel offers endless Vermont recreational activities on site and just down the road. There is hiking, biking, sledding, snowshoeing, snowmobiling, and hunting right out the front door, and in just a short drive you have Lowell Lake to kayak, fish, and hike, Stratton Mountain, Okemo Mountain, Bromley Mountain, and Magic Mountain ski resorts, the famous Vermont Country Store to shop and eat, the quintessential towns of Chester and Weston offering farmers markets and music. The property also has an abundance of tranquility and peace. It is located at the END of a town maintained road and borders the backside of a large neighboring parcel and town owned land. The parcel offers mountain views, moonlite and starry nights, an abundance of wildlife, streams, old stonewalls, and snowmobile vast trails located just at the base of the driveway. The parcel has many improvements including a long gravel driveway leading you up to a 28 x 36 camp that is fully insulated, many Andersen and Marvin windows and doors throughout, generator powered, a back bunk room that sleeps 7 or more, a cozy loft to make your own, and lets not forget the covered porch overlooking the ridge line mountain view. Don't miss out on this rare find with many options, keep it a camp, live off the grid, or make it your home.

Listed by Rachel Febbie of Bean Group / Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 2023 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 June 2, 2023 7:55 AM EDT