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!

28 Mineral Springs Road Chester VT 05143

Chester, VT28 Mineral Springs Road

Price$159,000

Est. Mortgage: $/month

MLS Number 4991554

  • Mobile
  • Area Rural
  • Listing Agent Name Daire Gibney
  • Year Built 1993
  • Garage Spaces 2

This wonderfully well-maintained home sits back nestled off of route 12 between the village of Chester and town of Springfield. This property features 2 bedrooms and 1 1/2 bathrooms, a standing seam roof, an oversized two car garage and a nice open lot.

Listed by Daire Gibney and Thaddeus Abare of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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

12 Common Street Chester VT 05143

Chester, VT12 Common Street

Price$485,000

Est. Mortgage: $/month

MLS Number 4990677

  • Multifamily
  • Units 3
  • Bathroom 1
  • 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 2bedroom 1 bathroom which has recently been updated with a freshly painted interior as well as new flooring and other updates. Along with the many benefits of this property's 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.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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

4877 Vt Route 103 Chester VT 05143

Chester, VT4877 Vt Route 103

Price$675,000

Est. Mortgage: $/month

MLS Number 4986618

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,728

Looking for the perfect ready to move in home in Vermont? This beautiful home is centrally located in the quiet town of Chester, Vermont on Route 103. Close to many ski mountains, within 10 minutes to Okemo mountain. House features a beautiful indoor and outdoor fireplace, outside hot tub, beautiful stone patio, large private deck, 2 car garage, 4 bedrooms (but lots of room for more people), 2 bathrooms, a bonus bunk room, 2 extra lofts for an office or library, extra recreation room, and paved driveway. The house is a short distance to several beautiful lakes, mountains to hike, near the VAST trails, and interstate 91. Very spacious and also currently a great short term rental income property. And if you happen to lose power there is a 20kw stand-by propane generator ready to go. Call for a showing today!

Listed by Erin Kendall of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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

242 Mattson Road Chester VT 05143

Chester, VT242 Mattson Road

Price$225,000

Est. Mortgage: $/month

Pending

MLS Number 4984020

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,344

Built in 2004 sits this ranch style home situated on 2.3 acres. Features 3 bedrooms. 2 full baths, eat in kitchen , full basement, 2 car detached garage, back deck and a nice level yard!

Listed by Dick Thackston of R.H. Thackston & Company

$
$
%
$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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

341 Whitmore Brook Road Chester VT 05143

Chester, VT341 Whitmore Brook Road

Price$645,000

Est. Mortgage: $/month

MLS Number 4981700

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,400

With it's stone fireplace, exposed beams, and textured logs, this home offers an authentic connection to the great outdoors. For nature enthusiasts, the property's proximity to Okemo Mountain, hiking trails, VAST trails, golf courses, and swimming spots is unbeatable, all within 8 miles. Tucked away on Whitmore Road just up off of 103, this home offers privacy in a serene setting, yet still very close to all amenities. Though the house itself requires some tender loving care, it presents an exciting opportunity for those with vision and ambition. Picture transforming the spacious living area with its impressive stone fireplace to match your unique style. Cathedral ceilings create an expansive and airy ambiance. A designated area with a bar offers the potential to create a remarkable entertainment space. Adjacent to the house, a poured foundation awaits your creative touch, approved for a barn or additional structure. Whether you choose to complete the vision or let your imagination run wild, this property offers endless possibilities for customization and personalization. Escape the hustle and bustle of modern life and envision your own Vermont retreat in this charming log home. Schedule a showing today and take the first step toward turning your vision into reality.

Listed by Frank Provance and Dana Haley of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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

49 Putnam Hill Road Chester VT 05143

Chester, VT49 Putnam Hill Road

Price$350,000

Est. Mortgage: $/month

MLS Number 4972797

  • Residential Single Family
  • Construction New Construction
  • Bedrooms 5
  • Bathroom 4
  • Acreage 3.21

Located in the neighborhood of Putnam Hill in Chester, this newly constructed dormered 2.5 story 5 bedroom, 4 bath home on 3.2+/- acres has been framed and is utility ready with septic, well, electric in place. The first floor space features a Great Room with 16' ceilings at its highest points, large kitchen with work area and plenty of cabinet space, a separate dining room for large gatherings, a formal living room and full bath which could also function as a first floor bedroom. The second floor is designed for 4 bedrooms and 2 full baths and the third floor has flex space with four large dormers and beautiful views. This thoughtfully designed home includes a walkout basement with 9' ceilings and intentional framing to include large windows. Solid wood doors are on site along with 10” wide plank pine flooring, furnace and misc. materials. This home was built by a Master tradesman with years of experience. The architectural framing is quite remarkable as is the desirable location of Chester VT with short drives to various ski mountains.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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

117 South Main Street Chester VT 05143

Chester, VT117 South Main Street

Price$399,000

Est. Mortgage: $/month

MLS Number 4956139

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

Opportunity awaits! This three-unit property has been very well maintained and is fully rented with long term tenants. This investment features an in-town location within walking distance to shopping, restaurants and local conveniences. This property also includes additional unfinished square footage in the barn, currently used for storage, with great potential for new ideas. Even the basement is impressive. The outside of this home has been freshly painted as of 6/6/2023. All apartments are in good shape and fully applianced.

Listed by Thaddeus Abare of Barrett & Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.1% last updated on Apr 18, 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

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: 7.1% last updated on Apr 18, 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

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: 7.1% last updated on Apr 18, 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

Broker Reciprocity 

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 April 22, 2024 9:24 AM EDT