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

374 Richardson Road Chester VT 05143

Chester, VT374 Richardson Road

Price$749,000

Est. Mortgage: $/month

MLS Number 4908861

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

Gracefully settled between the villages of Chester and Londonderry, sits a Vermont Farmhouse at road's end, sited on eleven+ acres of wood'n meadow. Dotted with old stone walls, a wildlife pond and enchanting views. The setting is magical. A wide country porch invites rocking chairs and visitors while the screened area encourages outdoor entertaining much of the year. The vintage flavor is apparent throughout the home- opening panel doors with antique latches or stepping foot on wide wood floors milled from indigenous trees from decades ago. This location is central to recreating: ski, hike, snowmobile, swim, or enjoy our local restaurants, theater and shopping. A center island kitchen with breakfast nook overlooks the rolling meadows and glass doors allows life to spill over onto the porch, deck or firepit area. A traditional dining room, adjacent to the intimate living room, awaits memorable dinner parties. The great room's remarkable soaring ceiling creates a central gathering spot and includes a cast iron wood burning stove to warm by when winter is settling in and snow abounds . The main floor bedroom would also make a delightful home office overlooking the fields to the rear. Upstairs you'll find additional bedrooms including a large “beamed ceiling” primary and a fun multi-functional den/game room. Two sets of farmhouse stairs give easy access. If quiet and open and vintage is your desire..Look no further. Showings begin Thursday, May 12th. Owner is a licensed Realtor.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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

835 Quarry Road Chester VT 05143

Chester, VT835 Quarry Road

Price$675,000

Est. Mortgage: $/month

Pending

MLS Number 4908734

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

If you are searching for the perfect Vermont setting for year round living and enjoyment look no further than "Hidden Meadow". Situated on a very private 23.52 acres you will find a home and property that has been lovingly cared for by its original owners. The house features a tile entry way that leads to a comfortable living room with vaulted ceilings, hardwood floors and a custom built modified Rumford Fireplace that will heat the room on those winter nights. The living room leads out to a screened in porch were you can relax, bird watch and look out over one of the most beautiful properties you will ever see. The rest of the main floor boasts an open kitchen with an island, ample counter and cabinet space, a formal dining room, 3 large bedrooms including a Master with private bath and a laundry room. The second floor space can used as a bedroom or a great home office with fiber optic internet. 2 car attached garage with heated workshop and a full basement offers a tremendous amount of storage. The property is special with a wealth of perennial gardens, mature abundantly producing blueberry bushes, lupine fields, custom stonework and steps. The large pond is 20 ft deep suitable for swimming and home to 100's of rainbow trout. The barn is suitable for animals with plenty of open pasture. The location is ideal, just 1 mile to the historic Chester Green and only minutes to the picturesque town of Grafton. Skiing and outdoor activities are also just minutes away.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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

266 Main Street Chester VT 05143

Chester, VT266 Main Street

Price$529,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4907617

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

This 1780's stunning yet quaint home in the heart of Chester and Southern Vermont is truly the ideal location for a spectacular private residence or successful hospitality business. Owned and operated with love this building has provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. Currently rented out as an extended stay rental and generating $8,800 monthly. The period home with newly renovated 2 bedroom separate living quarters comes mostly furnished leaving you space to add your personal touches. The main floor is easily accessible with first floor accommodations for those needing to avoid stairs. Gracious rooms and cozy common areas invite you to relax in a central location allowing easy access exploring the surrounding Chester village and with mountains, lakes and streams all within short drive you will not lack options for fun and relaxation. Come see this charmer; you may want to stay awhile!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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

125 and 61 Trebo Road Chester VT 05143

Chester, VT125 and 61 Trebo Road

Price$249,000

Est. Mortgage: $/month

MLS Number 4906704

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

How sweet it is!!!....this home is perfect for those looking for full time or part time use. The main house is being offered furnished and will be ready to enjoy! Situated close to Route 103 for easy access to downtown Chester and short drives to 4 major ski areas. What items on your home wish list?? Mudroom/entryway (check), Garage for the car (check), country charm with nice wood beams (check), large deck for entertaining and relaxing outdoors (check)country setting with view (check), open living area (check)....included with the house is a guest cottage. Great income potential! Open house for both homes Saturday May 7th 11-2pm. Appointments for the main house anytime. New flooring in one bathroom and new hot water heater done this past month.

Listed by Lisa Kelley of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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

Lot 7 Jillie Lane Chester VT 05143

Chester, VTLot 7 Jillie Lane

Price$90,000

Est. Mortgage: $/month

MLS Number 4904758

  • Land
  • Acreage 7.76
  • Area Rural
  • Utilities None
  • Zoning Residential

Beautiful, wooded, and private! Located just outside of downtown Chester, on a private road with a maintenance agreement in place. Underground electric on site. Septic plans for a 3 bedroom single family home.

Listed by Thaddeus Abare of Barrett & Valley Associates,Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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

74 Cobleigh Street Chester VT 05143

Chester, VT74 Cobleigh Street

Price$485,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4903312

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

One of the true gems of Chester. This circa 1850 home has been transformed over the years. It has the charm of the original farmhouse yet has the functionality of a newer home. You enter into a lovely enclosed screened in porch with newer windows which also serves as an entry mudroom. You'll step into a large living room with a woodburning stove with new stainless steel liner added when the chimney was rebuilt. Good sized kitchen has ample counter space and cabinets as well as an eat-in island with stools. The formal dining room has hardwood floors and a gorgeous bay window looking out to the front yard. First floor features an inviting family room with a wet bar, gas fireplace and access to the backyard patio. You'll also find on the main floor a bedroom, full bathroom, arts and crafts room and an amazing sunroom with brand new windows looking over the backyard. The upstairs features 2 bedrooms including an owners suite with a laundry room, dressing room, huge walk-in closet and a master bath with radiant heat and a double marble sink. There is also a second floor office for working at home. The property is special. It's beautifully landscaped all around with a vegetable garden bed, multiple outbuildings including a new 10X14 shed, small fish pond,fire pit and patio for endless hours of outdoor enjoyment. A 3 bay garage was also added in the past year. The house was recently painted and is move in ready. All this just a short distance to the historic town green.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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

Grafton Road Chester VT 05143

Chester, VTGrafton Road

Price$360,000

Est. Mortgage: $/month

MLS Number 4903171

  • Land
  • Acreage 142.1
  • Area Near Skiing, Rural
  • Utilities None
  • Zoning Residential

Don't miss the rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning 142.1 +/- lot is made up of two separate but adjoining parcels, one in Chester comprising of 70.1 acres and 72 acres in Grafton. Each has road frontage on onto route 35 between Chester and Grafton. If you have conservation on your mind both parcels are enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded with small ponds on the Chester lot. There are also a network of logging trails throughout the property. Come see today!!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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

Howard Road Chester VT 05143

Chester, VTHoward Road

Price$65,000

Est. Mortgage: $/month

Pending

MLS Number 4903023

  • Land
  • Acreage 6
  • Zoning Residential

Beautiful, quiet 6 acre wooded lot located just 2.5 miles from the center of lovely Chester, VT. Undeveloped land is becoming harder to find so don't miss out on the opportunity to build your Southern Vermont dream home and enjoy all this sweet spot has to offer. Just 20 minutes to Okemo, and another 30 minutes to Killington, and only 15 minutes from I-91.

Listed by Christopher Cummings of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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

3078 VT Rt 10 Chester VT 05143

Chester, VT3078 VT Rt 10

Price$399,000

Est. Mortgage: $/month

Pending

MLS Number 4902497

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

Beautiful cape home on level country lot bordered by stone walls. Mature landscaping, above ground pool, screened gazebo, large back deck, 2-car attached garage along with attached utility shed, additional single car garage, walk out basement, first floor bedroom, open floor concept, stainless steel appliances. Second floor has two generous sized bedrooms, full bath and a bonus room for a home office, reading nook craft area or whatever you like. Home has been nicely updated. This home is turn-key. DELAYED SHOWINGS START WEDNESDAY MARCH 30, 2022

Listed by Julie Buffum of Buffum Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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

5032 Vt Route 103 N Chester VT 05143

Chester, VT5032 Vt Route 103 N

Price$214,500

Est. Mortgage: $/month

Pending

MLS Number 4901597

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

This three bedroom, 1.5 bath home is just minutes to Ludlow and Okemo Mtn. ski resort. There is a large 4 car detached garage with office space and finished space above offering plenty of room for your hobbies and storage for all of your "toys". Large storage / mud room entry, walk in pantry, partially finished basement and direct access to the Williams River for outdoor recreation. There will be no showings. No trespassing.

Listed by Judith Thompson of Walnut Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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

3074 VT Route 10 Chester VT 05143

Chester, VT3074 VT Route 10

Price$329,500

Est. Mortgage: $/month

Active With Contract

MLS Number 4900961

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

Set back from the main road, is a very well-maintained 3 BR / 2 BA home with attached 2-car garage. Lovely and sun-lit living room. Eat-in kitchen is fully applianced with many cabinets and counterspace. Off of the kitchen is a deck. Master bedroom includes a large closet [2'x7.9"] and adjoining bath. Two additional bedrooms; one bedroom currently being used as an office. Lower level is finished [16x27.7] and can be considered to be a bonus room; perhaps bring in a pool table or ping pong table! Additional storage rooms in the basement. Very nice level land parcel: plenty of room for gardens and a back patio area. There is a firepit in the backyard along with a small pond. On the front side of the house is a small shed which could be ideal for a garden shed, and/or a small playhouse. [Subject to Sellers' finding suitable housing].

Listed by Amy Messina of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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

369 Logan Drive Chester VT 05143

Chester, VT369 Logan Drive

Price$369,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4899093

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

COUNTRY COMFORT.....This home and detached heated garage/shop enjoys a peaceful setting on 14+ acres. The homes interior has been recently and tastefully updated consisting of 2 bedrooms, 2 baths and an open living/dining/kitchen floor plan. The custom kitchen with bar island and pantry will please even the most critical cook in the family. The large master suite has slider access to an oversize covered deck that overlooks the property. With only a little tiding up of siding where new windows were installed, this home has very little left that is undone and is ready to move into. The well maintained road provides access to just a few neighboring properties with easy access to a paved town maintained road just a minute away.

Listed by Roger Danyew of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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

Broker Reciprocity

Copyright 2022 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 May 25, 2022.