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

662 Main Street Chester VT 05143

Chester, VT662 Main Street

Price$395,000

Est. Mortgage: $/month

MLS Number 4828399

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

Located in the heart of the village, just a short distance from the historic Chester Green you will find this absolute gem of a home and property. This is a wonderfully cared for 3 bedroom, 3 bathroom family home that boasts refinished hardwood floors and freshly painted rooms. The first floor has a large kitchen with tons of counter space and cabinets as well as a brand new gas range. You'll find a lovely formal dining room with a built in china cabinet. Off the dining room is a den ideal for a home office or study. The living room features and abundance windows facing the front yard that allows for great sunlight all throughout the day. You will also find a full bath and laundry room on the first floor as well as a four season sky lit sunroom off the kitchen that opens out to the back wrap around deck. The second floor features a large primary bedroom with new flooring and its own private bath with walk in closet and a soaking tub. You'll also have fantastic view of the beautiful pastures of neighboring Buttonwood farm. There are two other good sized bedrooms and an additional bathroom rounding out the second floor. All on a level village lot with a classic New England front porch to relax and watch the world go by. Property also boasts a one car garage and a nice private back yard. Conveniently located close to 4 major ski resorts and a short distance to all town amenities. This sweet village home is move in ready and waiting for it's next chapter.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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 TourAsk A QuestionMore Details

489 Main Street Chester VT 05143

Chester, VT489 Main Street

Price$237,900

Est. Mortgage: $/month

MLS Number 4828325

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

Village home. Stroll to Chester Green. Zoned residential/commercial. Large casually elegant living, or combo home/gallery. Possibilities are many! Spaces filled with artistic touches from recent-years' restored original hardware to a basement with granite stone floor created by the true craftsmen of Old Vermont. Charm & character fill this c.1860 farm-style house. Artful restoration & renovation give this clean elder dame a balance of the past with today's convenience & comfort. Lot has been transformed into low-maintenance perennial gardens that bloom from early spring until November's freeze. Back gate opens to enclosed courtyard - your very own Secret Garden! Enter house through an always-sunny Sun Room. Dutch door opens to spacious kitchen-dining, recently updated with matte stone farmhouse sink, quality faucet, new countertops & backsplash. Chef-friendly appliances. Soapstone wood stove. Large walk-in pantry has shelves, countertop & cabinets. From kitchen-dining area, pass a bright hallway to the charming side entrance.1st level then opens to library-living room with wall of solid built-ins & rugged stone fireplace. More upstairs: Bedrooms, full bath, & laundry-utility room. Charming enclosed porch leads to exit & covered exterior stairs back to the private courtyard. Into the happy blue Barn door is a potting shed/workbench, upstairs storage & 1-car garage. In back of barn is ScreenRoom, side & front doors that open to large fenced & gated yard & majestic Black Walnut

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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 TourAsk A QuestionMore Details

Stage Chester VT 05143

Chester, VTStage

Price$149,000

Est. Mortgage: $/month

MLS Number 4827417

  • Mobile
  • Listing Agent Name Daire Gibney
  • Year Built 1996
  • Bedrooms 2
  • Square Feet 924

This picturesque lot commands a stunning view from its lofty perch overlooking Stage Road in Chester. The lot is a mix of open field and forest. This would be perfect for your new dream home, gentleman's farm or simply a great getaway location. This location has so much potential for expansion and will be easily developable. Just insert your imagination.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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 TourAsk A QuestionMore Details

Grafton Chester VT 05143

Chester, VTGrafton

Price$65,000

Est. Mortgage: $/month

MLS Number 4827526

  • Land
  • Listing Agent Name Daire Gibney
  • Acreage 21.6
  • Area Rural
  • Zoning Res

This 21 +/- acre lot has an active Act 250 permit allowing for a 1 +/- acre Mica schist stone quarry. The site has a driveway into a level area that could host a camp or be developed for a home. Ideal as an investment opportunity or would make a wonderful location for a hunting camp. This lot can be sold separately or as part of a larger land holding of 540 +/- acres that is currently enrolled in the value use program. see MLS 4822981

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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 TourAsk A QuestionMore Details

225 Pleasant Street Chester VT 05143

Chester, VT225 Pleasant Street

Price$399,000

Est. Mortgage: $/month

MLS Number 4826630

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

This beautiful Victorian has been a successful Inn for many years and will make a wonderful location for anything you can imagine, be it a business or a family home. With 9 bedrooms and 8 bathrooms plus parking for 8-10 vehicles there is ample space to run a business or host a large family retreat. With several Ski resorts all under 30 minutes away this is an ideal property for a Ski/recreational club house. There is plenty of room to entertain with a large dining room, living rooms and the old tavern with a large deck for lounging on after a day of exploring the area. The property has been lovingly maintained and it shows. Just moments from the quaint Village of Chester and quick access to I91 it is conveniently situated to access all the wonders Vermont has to offer. This is without doubt a special place. Come look today!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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 TourAsk A QuestionMore Details

538 Clemons Road Chester VT 05143

Chester, VT538 Clemons Road

Price$299,900

Est. Mortgage: $/month

Pending

MLS Number 4826184

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

Nestled in the woods, with a big clearing around the house, this property is everything one would want for easy living with lots of storage/garage space. The house is an easy keeper; ranch style with large mudroom/entry, open concept living/dining/modern kitchen, master suite with large walk-in closet and designer master bath, another main floor bedroom/den & bath. Finished basement with family room, summer kitchen, bathroom, craftroom/bedroom, laundry room and impressive utility room. Heated attached garage is three plus bays wide (one drive through bay) with oversized doors, high ceilings and overhead storage. Multiple extras include: Deck, outdoor furnace, solar, mini-splits, radiant heat, fire pit, shed and so much more...

Listed by Lori Muse of Muse and Associates Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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 TourAsk A QuestionMore Details

1072 Grafton Chester VT 05143

Chester, VT1072 Grafton

Price$85,000

Est. Mortgage: $/month

MLS Number 4826247

  • Mobile
  • Listing Agent Name Daire Gibney
  • Year Built 1995
  • Bedrooms 2
  • Square Feet 952

This is a fantastic location just minutes to the Village of Chester. This lot and the adjacent one, which is also available, are separated by a lovely pond making this a wonderful location for a family compound. These are also ideal sites to build your dream house and have an investment property right next door! See MLS 4826249

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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 TourAsk A QuestionMore Details

1074 Grafton Chester VT 05143

Chester, VT1074 Grafton

Price$85,000

Est. Mortgage: $/month

MLS Number 4826249

  • Mobile
  • Listing Agent Name Daire Gibney
  • Year Built 1987
  • Bedrooms 1
  • Square Feet 952

This is a fantastic location just minutes to the Village of Chester. This lot and the adjacent lot, which is also available, are separated by a lovely pond making this a wonderful location for a family compound. These are also ideal sites to build your dream house and have an investment property right next door! See MLS 4826247

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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 TourAsk A QuestionMore Details

656 Depot Chester VT 05143

Chester, VT656 Depot

Price$167,000

Est. Mortgage: $/month

MLS Number 4825906

  • Multifamily Multi-Family
  • Square Feet 2,280
  • Units 3
  • Bathroom 3
  • Acreage 0.13

Configure this property to your liking. This property can easily be a three unit with Three one bedroom units or or as two units with a one bedroom first floor a two bedroom townhouse. Located near the Chester Depot with the Williams River to the rear, this property is within walking distance to all the local amenities. Easy care with metal roof, vinyl siding, laminate and low pile carpet. Newer propane heating system services the entire property, electric is split out between the units, town water/sewer, shed for storage.

Listed by Lori Muse of Muse and Associates Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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 TourAsk A QuestionMore Details

527 North Chester VT 05143

Chester, VT527 North

Price$249,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4824826

  • Multifamily Multi-Family
  • Square Feet 2,310
  • Units 3
  • Bathroom 2
  • Acreage 0.5

Rare opportunity to own one of the finest commercial/residential properties in the area. Property includes two 1 bedroom apartments that have been completely renovated with fully separate utilities and a 1,200 commercial space that has been a successful country store and is currently leased to a successful local business. Also in the past has been run as deli and pizza restaurant. This is an excellent opportunity for an investor or an entrepreneur. So many possibilities exist including living and working on the property or just collecting rental income. As a business opportunity you'll be glad to know the VT Transportation Dept study in 2019 determined the average number of cars passing by per day is 4,200. This is an terrific location on RT 103 on the way to Okemo Mountain. Even with the high visibility you'll be pleasantly surprised to find it to be a very peaceful location. The property itself has been beautifully cared for by the current owners. The property boasts paver walkways, perennial plantings, manicured lawn and a 900 Sq Ft storage barn with a front porch that makes it look like a small home. The possibility exists to turn this into living space. The apartments have a wonderful private fenced in patio exclusively for the tenants or the owner as well as designated parking. This is a unique property that is well worth a look.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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 TourAsk A QuestionMore Details

233 Dodge Road Chester VT 05143

Chester, VT233 Dodge Road

Price$649,000

Est. Mortgage: $/month

MLS Number 4824858

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 4
  • Construction Existing
  • Zip 05143

Expanded Colonial home nicely tucked away on a lovely 3.6 acre lot. The original home was built in 1985 and has been meticulously cared for and maintained. You'll find a large formal living room with wide pine floors and gas fireplace that leads out to a balcony deck that overlooks the property. The kitchen boasts granite counters, ample storage with shelves and cabinet space and an eat-in counter with stools. It opens up to a breakfast sitting area and a large dining room that is a wonderful gathering area for family and friends with its openness to the rest of the home. This leads out to a large year round sunroom with access to the back deck for grilling and the hot tub. 3 Large bedrooms upstairs comprise the original home. The expansion of the house includes a 2 car attached garage and completely finished upstairs that has an open den area, bath, and three more bedrooms also attached to the original home. In the walkout basement you will find a large 20X15 mudroom for ski equipment and outdoor toys. A 16"X27" rec room, game room, laundry room and utility room with workshop and ample storage. The property is wonderful with a street light lined driveway, a storage barn with many uses and even a small cottage that could be restored for a playhouse or maybe an office. The house is being offered fully furnished and turn-key. All this less than a 1/2 mile to the town green. Located just 20 minutes to Okemo. Perfect family retreat or year round residence. Must see.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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 TourAsk A QuestionMore Details

580 Marcs Drive Chester VT 05143

Chester, VT580 Marcs Drive

Price$449,999

Est. Mortgage: $/month

MLS Number 4825102

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

Immaculate Custom Ranch situated on 5.3 acres on quiet cul-de-sac awaits you. This stylishly designed property features a large covered front porch, 2 car attached garage and a great view of the rear yard from the cedar screened porch with Trex decking. Welcome yourself through the mudroom which doubles as a convenient laundry room. Adjacent is a spacious state of the art eat-in kitchen including light birch cabinetry, granite countertops and wine chiller. The formal dining room is perfect for family holiday dinners. The open living room is home to the center brick wood burning fireplace and just around the corner is a cozy study/office, two bedrooms, full bath and a generous-sized master bedroom suite with a private bath and sizable walk-in closet. The partially finished lowest level offers natural daylight in the finished bonus space perfect for extra guests with a large living area and 1/2 bath. There is more to be desired with plenty of additional space that is currently set up as an in-home gym. This property even includes direct access to the VT Vast trail system. Within walking distance to the Village Green, a short drive to Okemo, Magic and Bromley mountains and only a 15 minute drive to Interstate 91. Also close by you can enjoy Echo Lake at Plymouth State Park. With Fiber-optic internet you can work from home with ease. You really can have the quintessential Vermont home for part time or year round living. Do not miss this pristine property with so much to offer!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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 TourAsk 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 September 19, 2020.