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. 

Chester, Vermont is a charming small town tucked away in the Green Mountains. From its quaint buildings to its tranquil rivers and lakes, this beautiful town has something for everyone. Spend an afternoon wandering through the picturesque downtown area and local businesses, take a peaceful stroll through the surrounding countryside, or simply sit back and marvel at the magnificent mountain views – no matter what you choose to do, Chester will offer an unparalleled experience!

Learn More About Chester VT

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

2033 VT 11 West Route Chester VT 05143

Chester, VT2033 VT 11 West Route

Price$275,000

Est. Mortgage: $/month

MLS Number 4955369

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

This quaint home sits pretty overlooking the banks of the middle branch of the Williams River and is just a moment from the charming village of Chester Vermont. The home has been lovingly maintained and is ready to be yours. Access and commutability are key here with quick access to I91 but also a short distance to many of the local ski areas and recreational activities. With a direct entry garage, ground floor primary bedroom, and new electrical panel this property is ready to go as your new family home or an amenable retirement retreat. All that is needed is some cosmetic updates and you will have a stunning home in a fantastic location. Come home to the sound of the river flowing in the back yard. The lot is bright and sunny with ample space for gardens, a greenhouse, and more. Come see this pretty riverside home 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

250 North Street Chester VT 05143

Chester, VT250 North Street

Price$289,000

Est. Mortgage: $/month

MLS Number 4954942

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 2
  • Construction Existing
  • Zip 05143

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

Open House

MLS Number 4954753

  • Residential Single Family
  • Next Open House: Sat 06/3 11:00 am. to 3:00 pm.
  • Bedrooms 3
  • Bathroom 2
  • Construction New Construction

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
  • Bedrooms 7
  • Bathroom 8
  • Construction Existing
  • Zip 05143

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
  • Bedrooms 3
  • Bathroom 1
  • Construction Existing
  • Zip 05143

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

514 1st Avenue Chester VT 05143

Chester, VT514 1st Avenue

Price$549,500

Est. Mortgage: $/month

Open House

MLS Number 4954146

  • Residential Single Family
  • Next Open House: Sat 06/3 11:00 am. to 2:00 pm.
  • Bedrooms 5
  • Bathroom 5
  • Construction Existing

Charming village colonial farm house in the historic Stone Village of Chester. Enjoy a country setting farm with 4.8 acres located within walking distance to town, 10 minutes from Interstate 91 and 20 minutes to Okemo Mountain. In-law suite with private entry, kitchen and bath provide the opportunity for on-site caretakers, home business or guest quarters. Two-bay attached garage, and large barn provide plenty of storage and endless potential. Open House 06/03 from 11am-2pm.

Listed by Morriah Adams of BHG Masiello Brattleboro

$
$
%
$/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

1096 Mattson Road Chester VT 05143

Chester, VT1096 Mattson Road

Price$279,000

Est. Mortgage: $/month

MLS Number 4953451

  • Land
  • Acreage 82.5
  • Zoning residential 3 acres

Spectacular idyllic Vermont setting is being offered for you. It does not get much easier than this for parcels of land. Property includes over 80 acres and features spring fed pond, a 5 acre cleared home site with 5 bedroom state approved septic permit in place, driveway complete with drainage culverts, views of Okemo and Ascutney mountains, stonewalls, babbling brook and all within 25 minutes of Okemo Vail resort! Need I say more?? Most of the property is in current use and was last logged in 2017. There are trails that crisscross throughout the property. This is the property you have been dreaming of...room to hike, snowshoe, sled, ATV ride you name it.

Listed by Lisa Kelley 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

332 Marcs Drive Chester VT 05143

Chester, VT332 Marcs Drive

Price$559,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4952412

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

This pristine home simply shines with modern charm. From maple cabinets to marble countertops this home oozes comfort but with clean lines and a cozy modern touch. The home sits in the middle of beautifully landscaped 5-acre lot that is private yet minutes to the charismatic and charming village of Chester. Featuring 4 bedrooms including an additional in-law or rental suite with private deck and patio; finished basement large 2 car attached garage, covered and open decks on two sides, lots of outside storage, Horseshoe pit, gardens and even an area to park the RV. This wonderful home offers many opportunities as both a full-time home and vacation get away. The oversized barn is perfect for a car collection or recreational vehicles. Close to the VAST and with Okemo Mtn less than 15 minutes away there is lots to do close by. Thankfully this home needs nothing and has been exceptionally maintained leaving you time to enjoy the Vermont beauty that surrounds you. Come see this beautiful home today. Open House 5/13/2023 10.30am to 2.30pm!!

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

674 Williams Road Chester VT 05143

Chester, VT674 Williams Road

Price$549,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4951527

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

This beautiful log home is in the perfect end of the road location for an outdoorsman and is in immaculate condition. This home has been cared for with tremendous attention to detail and has many features including an amazing wrap around porch, plenty of privacy, wonderful woodwork, a partially finished basement, a metal roof that is in fantastic condition and much more! The very nice pine floor is lined with radiant heat to help fight the Vermont winters but also has baseboard heating and a wood stove. The kitchen features all custom maple cabinets and newer appliances. The open concept floor plan is perfect for hosting friends or family with plenty of space for sleeping on the second floor in the primary bedroom with a bathroom, the two bedrooms on the first floor that are generously sized or the massive loft area perpendicular to the primary bedroom. This home offers a fantastic opportunity to getaway from the every day hustle and bustle and enjoy peace and quiet. Snowmobiles do have direct access to the vast trail system, many other hiking and walking trails can be completed from the property as well.

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

268 South Main Street Chester VT 05143

Chester, VT268 South Main Street

Price$215,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4950657

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

This remarkable home is a site to behold. Charming single level cape style home has been renovated with tons of major improvements including, newly painted exterior, new roof in 2022, completely renovated full bath with tub/shower from Bath Fitters with a lifetime warranty. New oversized Anderson Windows throughout the home, new front door with storm door all with a transferable lifetime warranty. All new appliances, Vermont Castings wood stove that can heat the house. Two mini-splits were installed in the living room and bedroom for A/C and an additional heating option to go along with the woodstove and the forced hot air oil furnace. Sellers rarely use the furnace making this an incredibly efficient home. There is no wasted space with this layout. Basement also has a versatile room that would be ideal for an office or additional living space. The kitchen is very functional with good storage and it leads out the patio and the beautiful backyard with river frontage on the middle branch of the Williams River. Outstanding location with easy accessibility to local restaurants, shops and services. Just a short distance to several major ski areas, the town green and the Chester town recreational area with pool, tennis, skateboard park, disc golf, ballfields, basketball courts, sledding, skating, snowmobiling, hiking and much more.. Just about 7 miles to Rt 91. This is a true find and a must see.

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

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
  • Bathroom 4
  • Construction Existing
  • Zip 05143

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

135 Stone Hedge Lane Chester VT 05143

Chester, VT135 Stone Hedge Lane

Price$649,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4950609

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

Welcome to 135 Stonehedge Lane. Situated at the end of the road sits this beautiful three-bedroom, two-bathroom home on a breathtaking ten acres. This home is majestically perched above offering panoramic views, from inside and out, of open fields and the picturesque pond all bordered by stonewalls. Inside, the sprawling open floor plan consists of a chef's kitchen and breakfast nook with French doors looking out to the stone patio with views of the pond. The living room features a custom entertainment center and gas fireplace for those chillier Vermont days. Open to the living room, the formal dining room has an abundance of space for entertaining your family and friends. The en suite primary bedroom looks out to the backyard and views beyond. Enjoy the convenience of an attached garage entering into the mudroom area. Floor-to-ceiling arched windows and trey ceilings are found throughout. Solar panels will provide much of the electricity needed for use of the heating, cooling, and electrical. Prime location close to ski areas (15 min to Okemo), golf courses, our lakes region, shopping, and amazing local restaurants. Taxes are based on current town assessment.

Listed by Katherine Burns and Sarah Sheehan 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

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 2, 2023 9:12 AM EDT