Flat Fee Real Estate logo

Chester VT Real Estate

Nestled in the Deerfield Valley of Vermont, Chester is a small town known for its old-world charm and hospitality in Windham County. This picturesque community boasts numerous attractions such as Grafton Village Cheese Factory, Southern Vermont Arts Center, and Silver Lake State Park. Visitors can explore local history at sites like Old Fort West or visit the Basketville store to purchase unique handmade crafts. With plenty of restaurants, cafes and pubs to choose from, Chester offers something for everyone. Whether you're looking for a romantic getaway or simply an enjoyable place to spend time with family and friends, Chester is sure to deliver an unforgettable experience.

Browse available Chester VT real estate below. 

Find Real Estate for Sale in Chester Vermont

Tip - Create an account (it’s free) to save your favorite Vermont real estate listings and get notified when similar properties are posted.

Questions? Call Flat Fee Real Estate at​ 802-318-0833 or contact us online!

548 Main Street Chester VT 05143

Chester, VT548 Main Street

Price$550,000

Est. Mortgage: $/month

MLS Number 4955974

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,622

One of the most remarkable homes you'll ever see. This 1841 historic stone home in the Chester downtown has been completely renovated to near perfection, paying homage to its long history while adding the modern comforts you'd expect. It all starts with a beautifully landscaped front and a welcoming covered porch. On the first floor you will find an elegant front parlor, dining room and a fully renovated country kitchen. The primary bedroom is also on the first with an ensuite bathroom. As you make your way through the back of the home you'll find a side entry mudroom off the paved driveway, A laundry and a 3/4 bathroom with exposed stone wall, one of the many character touches you'll notice. You'll then step down to the new family room with built-in shelving, gas stove and a bay window looking out to the incredible backyard. The second floor gives you three good sized bedrooms including one with ensuite bathroom. There is also a newly finished bonus room above the extension for your extra guests or just additional living space.The attached barn boasts a one car garage, a heated workshop and a hallway that leads to a back balcony. The property is nothing less than a gardener's paradise. Beautifully landscaped with spectacular perennial gardens, raised vegetable beds, garden sheds and even a new greenhouse. The new side patio with privacy fence is a wonderful place to relax and enjoy the property. Showing begin Friday June 9th with an open house Saturday June 10th. 10-2pm.

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

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

117 South Main Street Chester VT 05143

Chester, VT117 South Main Street

Price$435,000

Est. Mortgage: $/month

MLS Number 4956139

  • Multifamily
  • Units 3
  • Bathroom 3
  • Acreage 0.75
  • Square Feet 2,008

Opportunity awaits! This three unit has been very well maintained and cared for. This property features an in town location in walking distance to shopping, restaurants and more. All units are currently rented with long term tenants that have cared for the building well. This property even includes addition unfinished square footage in the barn currently used for storage with much potential for new ideas.

Listed by Thaddeus Abare 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

17 Grafton Street Chester VT 05143

Chester, VT17 Grafton Street

Price$305,000

Est. Mortgage: $/month

MLS Number 4955578

  • Multifamily
  • Units 2
  • Acreage 0.37
  • Square Feet 1,824
  • Area In Town

Classic 1852 brick colonial home located on the corner of Grafton and Main Streets in beautiful downtown Chester. A short stroll to the town green, library, shops and antique shops. Currently a 2 unit apartment, it's top floor consists of a two bedroom one bath unit while the downstairs is set up as a one bedroom cozy apartment. The house can very easily be converted back to a single family home by simply removing a wall on the lower level which was installed only a few years ago. The whole house has electric and plumbing updates. Two recent hybrid water heaters and furnace. A new roof was just installed. Priced to sell, please note current tenants are occupying both units. Appointments with at least 48 hours notice are needed. Showings will be scheduled in blocks of time. This is an excellent opportunity to either convert the home back to a single family or live in one and rent the other. Visit the Okemo real estate community today Taxes are based on town assessment.

Listed by Katherine Burns and Joseph Karl of William Raveis Vermont Properties

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

17 Grafton Street Chester VT 05143

Chester, VT17 Grafton Street

Price$305,000

Est. Mortgage: $/month

MLS Number 4955577

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,824

Classic 1852 brick colonial home located on the corner of Grafton and Main Streets in beautiful downtown Chester. A short stroll to the town green, library, shops and antique shops. Currently a 2 unit apartment, it's top floor consists of a two bedroom one bath unit while the downstairs is set up as a one bedroom cozy apartment. The house can very easily be converted back to a single family home by simply removing a wall on the lower level which was installed only a few years ago. The whole house has electric and plumbing updates. Two recent hybrid water heaters and furnace. A new roof was just installed. Priced to sell, please note current tenants are occupying both units. Appointments with at least 48 hours notice are needed. Showings will be scheduled in blocks of time. This is an excellent opportunity to either convert the home back to a single family or live in one and rent the other. Visit the Okemo real estate community today. Taxes are based on town assessment.

Listed by Katherine Burns and Joseph Karl of William Raveis Vermont Properties

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

250 North Street Chester VT 05143

Chester, VT250 North Street

Price$289,000

Est. Mortgage: $/month

MLS Number 4954942

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,152

An incredible opportunity to own one of the most historic homes in Chester. Located in the Chester Stone Village this classic stone home was built in 1844 and is loaded with character and history. ( See attached information sheet). Home has over 2,100 Sq Ft of living space with 4 bedrooms and 2 baths including a first floor bath that has been redone. Large kitchen is ready for expansion and the large dining room and front family room are great places to gather in. The back barn room is attached and would a perfect studio space. Electrical updating and rewiring is currently being completed. The .32 acre stone village lot is lovely with room to garden and enjoy the outside. The side screened in porch will give you a peaceful place spend time. You also have a two car garage. This historic home and property is in need of updating but it would be well worth the investment. Priced accordingly and ready for its next chapter. Located just 20 minutes to Okemo Mountain, close to RT 91 and a short distance to the town green. Don't miss this opportunity to own a piece of Vermont history.

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

Save FavoriteSchedule TourAsk A QuestionMore Details

157 Murdock Road Chester VT 05143

Chester, VT157 Murdock Road

Price$675,000

Est. Mortgage: $/month

MLS Number 4954753

  • Residential Single Family
  • Bathroom 2
  • Construction New Construction
  • Square Feet 2,051
  • Bedrooms 3

A mix of artistry and environmental features are the strong points. This 3 bedroom house on 30+/- acres is only 8 miles to Okemo. This dream home was started with only the best materials and construction techniques. The dream is 95% finished and due to health factors the owner must sadly find the right owner who will bring this project to completion. Originally an off the grid fully sustainable home, it's now hooked up to the grid with backup Kohler generator and solar panels. Cedar siding with natural insect fighting abilities adorns the exterior and is protected by a high end standing seam roof. This house is ready for the elements! Inside the details continue, enter the garage and find a spacious mudroom space. The kitchen offers environmental quartz countertops of seashells and sea glass, equipped with an Italian LaNordica wood cook stove and stainless appliances with plenty of space to entertain. The beautiful oak floors and trim were cut from the homesite and milled locally. The main level is open concept and also includes a bedroom, office with French doors, full bath and laundry. Upstairs are the second and third bedrooms with a half bath. On the lower level walkout there is a Morso wood stove and to be finished rooms. The property comes with a cottage with a kitchen, wood stove, solar panels and a loft. This cottage is still off grid. Priced so you can finish this masterpiece! Taxes are based on current town assessment. Showings begin June 3rd at 11am.

Listed by Katherine Burns and Joseph Karl of William Raveis Vermont Properties

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

244 Main Street Chester VT 05143

Chester, VT244 Main Street

Price$599,999

Est. Mortgage: $/month

MLS Number 4954502

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 8
  • Square Feet 4,475

You can sometimes search a lifetime for a property like this, a home that has a story, a town that is known to be quintessential VT living, and one that you can operate as an Inn or Bed & Breakfast, or have a wonderful family compound. Seek no further than this 1800's historical Victorian. The main house has 6 bedrooms on the second floor each with it's own private bathroom. On the first floor you'll find a kitchen prime for your renovation ideas, a formal dining room, front living room and a den that's ideal for a home office with fiber optic internet. You will also find gorgeous hardwood floors, original interior oak trim and a grand stairway leading up to the second floor. There is also a 1 bedroom apartment upstairs above the barn area. The porch overlooks a gorgeous green and town setting with shopping and restaurants alike. Complete this package with a guest cottage that was just fully renovated. Being sold mostly furnished, this will not last through the Summer.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

154 Fletcher Hill Road Chester VT 05143

Chester, VT154 Fletcher Hill Road

Price$329,000

Est. Mortgage: $/month

MLS Number 4954295

  • Residential Single Family
  • Square Feet 1,324
  • Construction Existing
  • Bathroom 1
  • Bedrooms 3

Welcome to this delightful raised ranch, tucked away in the picturesque town of Chester, Vermont! Prepare to be swept off your feet by the sheer beauty of the Green Mountains surrounding this gem. It's an absolute dream for families and adventure seekers alike! With 3 cozy bedrooms and 1 full bathroom, this home sits on a generous 2.72 acres, offering plenty of space to frolic and revel in the great outdoors. The living area is bright and inviting, ideal for relaxing after a day of outdoor adventures. The kitchen and dining area boast an open layout, complete with newer appliances and direct access to the back deck. All three bedrooms are conveniently located on the main level, but wait, there's more! The lower level boasts an extra room that could serve as an office or den-a delightful bonus to fit your needs. And don't forget the spacious 2 car garage! It's an organizers paradise, providing ample room for all of your storage needs. Just a short jaunt of 30 minutes to Okemo Mountain, 40 minutes to Stratton Mountain, and a mere 5 minutes to the heart of Chester- a town brimming with quintessential small-town charm and a rich history. You definitely don't want to miss out on this fantastic opportunity to embrace the very best of Vermont living! Schedule your showing today! Showings begin 5/26*

Listed by Brittanie Caggige of Vermont Real Estate Company

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

32 Regina Lane Chester VT 05143

Chester, VT32 Regina Lane

Price$449,000

Est. Mortgage: $/month

Pending

MLS Number 4950705

  • Residential Single Family
  • Bedrooms 4
  • Construction Existing
  • Bathroom 4
  • Square Feet 4,104

This Beautiful expanded cape is in pristine condition. Being so new this home has many of the modern features and designs that are up to date including a wonderfully laid out and crafted kitchen with granite counter tops, a walk in pantry, perfect lighting and plenty of counter space. This home consists of an open floor plan connecting the kitchen-dining-Livingroom to make for a great space to host friends and family for whatever event may be happening. There is also plenty of space for them to stay with a handicap friendly basement level walk in accessory dwelling with a separate kitchen, bathroom, bedroom and even laundry. All this and it is nestled on a quiet private Vermont road only 14 miles from Okemo, 13 miles from Magic Mountain and only 22 miles from Bromley. You will find that this home is close enough to walk to the Chester green where you can find shops, reasturants and more!

Listed by Thaddeus Abare 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

4877 VT Route 103 Chester VT 05143

Chester, VT4877 VT Route 103

Price$675,000

Est. Mortgage: $/month

MLS Number 4947322

  • Residential Single Family
  • Construction Existing
  • Square Feet 2,208
  • Bedrooms 4
  • Bathroom 2

Incredible ready-to-go investment property or Spacious family home! 4 bed, 2 baths, large garage, 2 hot tubs, one inside and one outside. Privacy and all within 10 minutes of Okemo mountain. Many recent updates including landscaping with beautiful blue stone patio. Comes with a wonderful team of people to help you grow the business! Come See it today!

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

616 Mattson Road Chester VT 05143

Chester, VT616 Mattson Road

Price$379,000

Est. Mortgage: $/month

MLS Number 4947056

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,349

This one level Farmhouse sits on 22.5 acres just 10.4 miles from Okemo Mountain. The land offers an open field that could be perfect for horses or other farm animals, a calming stream, and a sloping wooded area with trails, ready to be explored. There is plenty of space in this charming home with a large covered front porch, mudroom perfect to store outdoor gear, a heated workshop and garden shed. A large post and beam barn has two levels an additional area with 3 stalls, a tack room and heated chicken coop. There is a new drive through barn located across the field perfect to house equipment. The owners have enjoyed this home for 23 years!

Listed by Jessica Citera of Cummings & Co

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

12 Common Street Chester VT 05143

Chester, VT12 Common Street

Price$495,000

Est. Mortgage: $/month

MLS Number 4929151

  • Multifamily
  • Units 3
  • Bathroom 2
  • Acreage 0.25
  • Square Feet 4,060

Located at the head of the Village Green, it has been home to many successful businesses! The beautiful post and beam interior is warm and inviting. Enjoy the high foot and vehicle traffic in a very desirable area which has long benefitted owners and their businesses. There are 3 units with much potential! The first being the business store front, second is a space in the back which could easily be turned into a rental with a kitchen and separate bathroom, the third is a second floor 2 bedroom 1 bathroom with much potential! Along with the many benefits of this properties location comes parking right on the Green. Some recent updates are the back portion on the building has a new roof and solar was added to the whole building recently as well. Owner may consider owner financing.

Listed by Thaddeus Abare 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

1377 Vtrt 103 Chester VT 05143

Chester, VT1377 Vtrt 103

Price$400,000

Est. Mortgage: $/month

MLS Number 4871606

  • Multifamily
  • Units 2
  • Bathroom 2
  • Acreage 3
  • Square Feet 2,280

Chester Vt 1377 VTRT 103. , Multi Family , Many good uses for property. One and two-family residential and professional office, retail store if it were a home occupation or home business.

Listed by Michael England of Michael England Real Estate

$
$
%
$/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

Broker Reciprocity 

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 7, 2023 10:53 PM EDT