Chester VT Real Estate

Scroll down to browse homes for sale in Chester, Vermont. Contact us to schedule a showing of your favorite Chester properties for sale or if you have any questions. Register with us to save your favorite Chester real estate listings and to receive email notifications when similar properties become available. 

You May Also be Interested in Browsing Homes for Sale in
Andover - Grafton - Windham

Learn More About the Chester Area

Clemons Chester VT 05143

Chester, VTClemons Road

Price$27,500

Est. Mortgage: $/month

MLS Number 4799774

  • Land
  • Acreage 5
  • Zoning Residential

Great location close to the town of Chester, quick access to Springfield and 10 minutes to Okemo Mountain yet is on a quiet town maintained dirt road. Secluded but quick access to the areas amenities make this a perfect parcel. This build-able lot has suitable areas for a home site and has power at road. The stone walls and the remnants of an old farm house foundation make this a very charming site indeed. Come look today!!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

442 Main Street Chester VT 05143

Chester, VT442 Main Street

Price$175,900

Est. Mortgage: $/month

MLS Number 4799855

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 1
  • Construction Existing
  • Zip 05143

This antique home maintains many characteristics of it's time. Always a family home, and ready for upgrades from it's new family to be. Live on Main Street and enjoy the benefits of sidewalks, conveniences, and meeting your neighbors on a stroll. Enjoy an outdoor covered patio, attached barn, garage, and an exceptionally large rear and side yard. The home has 4 bedrooms, amazing common area and super extended space on the second floor over the barn. Bring your creativity when you visit and imagine how you can nurture this home and make it your own!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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 A VisitAsk A QuestionMore Details

1031 Cummings Chester VT 05143

Chester, VT1031 Cummings Road

Price$29,000

Est. Mortgage: $/month

MLS Number 4799391

  • Land
  • Acreage 5
  • Zoning Res

Prime 5+/- acre Chester wooded corner lot with frontage on Cummings Rd. and Rte 11 East has residential and/or home business potential. Remainder land from old farm across the road, the parcel has Stone walls, dirt road and paved road frontage. A Stream traverses the property. Located in close proximity to Chester and convenient to Springfield. Make your access off the country road or utilize the major road frontage and exposure this property affords. The old camp on Cummings Road side marks the spot as possible building site.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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 A VisitAsk A QuestionMore Details

125 Whitmore Brook Road Chester VT 05143

Chester, VT125 Whitmore Brook Road

Price$189,500

Est. Mortgage: $/month

MLS Number 4797878

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

Tucked away on a quiet town road between Ludlow and Chester is this 4 bedroom home with lots of natural light, wood floors and open beams. Large open floor plan downstairs with a big updated kitchen, dining area and large living room with a stone hearth and gas burning stove. Enjoy the 2 +/- acres with an ample yard, matured landscaping & wooded trails. Poured slab for a garage. Would make a great ski house only 6 miles to Jackson Gore/ Okemo, Ludlow and all the amenities it has to offer.

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

Crow Hill Chester VT 05143

Chester, VTCrow Hill Road

Price$110,000

Est. Mortgage: $/month

MLS Number 4797415

  • Land
  • Acreage 46
  • Area Rural
  • Zoning Res

46 acres situated just off Flamstead Road on Crow Hill in Chester, VT. The property includes some level areas as well as wooded acres. The property might be just right for you to hunt, hike or build once a wastewater permit is approved through the state of Vermont. Over 700 feet of road frontage and lots to explore on your land!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

5032 Vt Rte 103 Highway Chester VT 05143

Chester, VT5032 Vt Rte 103 Highway

Price$155,500

Est. Mortgage: $/month

MLS Number 4795856

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

This 3 bedroom energy efficient ranch has been fully and professionally insulated, in addition to the weatherization that includes exterior vinyl siding and newer replacement windows, and a standing seam roof. An adjacent two story 4 bay garage...perfect storage for all of your toys, to include automobiles, snowmobiles, motorcycles. There is concrete flooring, a separate office area, and the the garage is also set up for heat (the oil tank and oil lines are in place for a furnace) and there is separate circuit breaker power. The second floor, with full stairway access, is open for a variety uses. Three of the doors are 8'x 8' and one is 8' x 10'. The home interior has a large, centrally located, eat-in kitchen, adjacent to both the living room and the dining room (with electric fireplace). There are two bedrooms, and a full bath, and a master bedroom with a 1/2 bath. The rear entry/access offers a large 4' x 17' storage/mud room. The partially finished basement includes 4 partitioned rooms with baseboard heat, plus a separate laundry area and an easy bulkhead outside access to the rear yard. Outside, there is 100' of Williams River rear yard access to fishing, swimming, and family enjoyment.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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 A VisitAsk A QuestionMore Details

465 Pennell Road Chester VT 05143

Chester, VT465 Pennell Road

Price$878,500

Est. Mortgage: $/month

MLS Number 4793511

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 5
  • Construction Existing
  • Zip 05143

This extraordinary residence and property is located in the vibrant community of Chester. Chester is easily accessed from Interstate 91 and is the gateway to many of Vermont best ski areas which creates an abundance of exceptional restaurants, cultural events and recreational options. The property is a south facing, very private 79 acres which consists of well maintained woodlands with a sugarbush and state of the art sugarhouse and open meadows in the forefront of long range views. Located just below the residence is a large swimming, fishing pond with an adjacent lighted tennis court. Trails for hiking, cross country skiing and mountain biking are throughout the property. Truly an exceptional setting that has been enhanced by the residence which is expertly sited to take in all that the property offers. The residence was designed and built by the owner who is a renowned wood craftsman. The level of craftsmanship displayed throughout the house is without equal. The choicest woods combined with incredible execution make for a truly unique environment. Every room and space in the house is warm and inviting while offering efficiency and sustainability. Combine this with state of the art systems and unexpected amenities including an adult sized and scaled treehouse make this property a must see for the discerning buyer. You won't be disappointed.

Listed by Wade Treadway of Wade I Treadway Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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 A VisitAsk A QuestionMore Details

289 Grafton Road Chester VT 05143

Chester, VT289 Grafton Road

Price$125,000

Est. Mortgage: $/month

MLS Number 4791875

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

Contractors and ambitious do-it-yourselfers: This is definitely worth a look! This once grand home and B&B has lacked maintenance and attention for about 10 years and needs your love and sweat equity. It was completely renovated about 30 years ago, so the bones are good - electric and mechanicals are up to code. It will need lots of cosmetic work and some basic plumbing repairs. The 4 bedrooms include a rather large suite upstairs that could be used for an owners quarters if you want to do the B&B. The yard, with some cutting could come back to the "old neighborhood ball field" again. This project will be well worth the investment. Walking distance to downtown Chester. Come and take a look.

Listed by Gail Beardmore and Uli Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

Brookside Chester VT 05143

Chester, VTBrookside Drive

Price$125,000

Est. Mortgage: $/month

MLS Number 4791293

  • Land
  • Acreage 16.4
  • Zoning R 120

16.4 acre Chester property with long range Southwestern views. Current owner purchased to plant a vineyard, and all research on this idea indicated it would work for grapes, but it could work for virtually any northern suitable farm or orchard crop. This private, 16+/- acre property has a western exposure with a southern tilt that basks in sunshine all day. There are three potential building sites with roughed-in driveways. At the top of the property is a private, small, spring fed pond. An inground cistern and underground concrete piping allow for water drainage. Pathways were roughed in but now need some clearing. This property would be perfect for carbon neutral development with on site wind, solar and hydro power all possible and practical. Enjoy Western views of Magic Mountain and romantic sunsets from your hilltop villa. With some vision and small growth clearing, the building sites can be reclaimed. Current septic permit in place for a 3 bedroom home.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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 A VisitAsk A QuestionMore Details

710 Baileys Mill Road Chester VT 05143

Chester, VT710 Baileys Mill Road

Price$365,000

Est. Mortgage: $/month

MLS Number 4790047

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

Privately sited among trees and open fields on 43.7 acres, this 2001 cape style home abuts 1,000's of acres of forest. The house features two bedrooms (town records say 3 bedrooms), 2 baths, a fireplace, farmers porch overlooking the field, and an open deck off the back of the house. There is a two-car attached garage. The driveway runs along a 3-acre field to a second field where the house is located. Much of the property is forested with sugar maple, red oak, white pine and hemlock.

Listed by T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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 A VisitAsk A QuestionMore Details

868 Goodrich Road Chester VT 05143

Chester, VT868 Goodrich Road

Price$39,999

Est. Mortgage: $/month

MLS Number 4789868

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

A Glamper's dream property! Charming, furnished 1 bedroom with sleeping loft, efficiency galley kitchen, living room and an outhouse built to state specs with elec. and heat on .25+/- acres in prime hunting, skiing, snowmobiling, recreation area. Town maintained road, newly re-built wall furnace, covered porch & a brand new deck. The lot is open and the cabin is close to the road for easy access. There is a nice yard with stone walls and borrowed landscaping beyond. A great way to be close to skiing for those who don't mind roughing it a little. Half mile to snowmobile trail.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

1782 B Quarry Chester VT 05143

Chester, VT1782 B Quarry Road

Price$175,000

Est. Mortgage: $/month

MLS Number 4788262

  • Land
  • Acreage 86
  • Zoning res

+/- 86 acre parcel with approximately 2200' of road frontage at the end of a dead end public road. Create your private estate or potential for subdivision. Some selective cutting done in early 2000 has opened up parts and created some nice logging roads. Land has a rolling hills, good remaining timber, trails and some elevated knolls for potential views. This parcel contains a former soapstone quarry. This is a great place to be out in nature but also have easy access via a town maintained road to electric, fiber and only five minutes to downtown Chester. Additional 148 acres (Lot C) or residence with +/-158 acres are also available. Subject to survey and subdivision approval. Don't miss this gorgeous parcel with unlimited potential.

Listed by Mark Roden of BH&G - The Masiello Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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 A VisitAsk A QuestionMore Details

Broker Reciprocity

Copyright 2020 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 April 7, 2020.