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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. 

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50 Grafton Street Chester VT 05143

Chester, VT50 Grafton Street

Price$329,000

Est. Mortgage: $/month

MLS Number 4977939

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,351

Discover your new home in Chester, VT! This versatile property features 4 beds, 3 baths, a spacious garage, and an RV port, accommodating single or two-family living. The flexible layout includes the potential for an in-law suite, or rental unit, making it adaptable to your needs. Well-maintained, has modern updates, and is a family-friendly and practical space filled with possibilities. Life in Chester is both convenient and charming. Enjoy the village atmosphere within walking distance to the Victorian village boasting historic charm, quaint shops, and local eateries. Schools and churches are within walking distance, adding to the community feel. Explore the Vermont outdoors with scenic trails and fishing spots, creating a serene environment. Winter enthusiasts can delight in the proximity of Okemo and Magic Mountain ski resorts for endless snow-filled adventures. Quick access to both I91 and VT Route 11 makes this a wonderful access point to the entire state of Vermont. This property isn't just a house; it's an opportunity to craft your ideal Vermont lifestyle. Join the welcoming community and make this house your home. Chester, VT offers practical living, a genuine community, and endless possibilities. Your dream home awaits in the heart of Vermont!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Dec 7, 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.

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3019 Popple Dungeon Road Chester VT 05143

Chester, VT3019 Popple Dungeon Road

Price$185,000

Est. Mortgage: $/month

Pending

MLS Number 4977752

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Square Feet 200
  • Bedrooms 1

Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage undergoing a complete renovation. Most of the interior demo work has been completed, waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny house while working on the original home. Consider the possibility of removing the older structure to make way for something new, or simply relish the tiny house as your Vermont getaway. A stone walkway leads gracefully down to the river, providing a tranquil connection to nature. Both structures are elevated above the flood zone, ensuring peace of mind in all seasons. This exceptional property is a nature lover's dream and a rare opportunity to embrace the essence of Vermont's natural beauty.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Dec 7, 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.

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656 Depot Street Chester VT 05143

Chester, VT656 Depot Street

Price$170,000

Est. Mortgage: $/month

Pending

MLS Number 4974297

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

Here's a good chance to have an investment property with three 1 bedroom units, or you can use one for your own Vermont getaway while enjoying the rental income from the other two. One unit is vacant and will remain that way giving the new owner the choice to either rent it out or use it themselves. Located in Chester Depot, within walking distance to the market etc. Fronted on the back by the Williams River, giving you an opportunity to have a nice place to relax in the summer. An easy drive to Okemo for skiing this winter!

Listed by Glenn Olney of Barrett & Valley Associates,Inc/Sprin

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Dec 7, 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.

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49 Putnam Hill Road Chester VT 05143

Chester, VT49 Putnam Hill Road

Price$399,000

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: 7.03% last updated on Dec 7, 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.

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1709 Potash Brook Road Chester VT 05143

Chester, VT1709 Potash Brook Road

Price$499,000

Est. Mortgage: $/month

MLS Number 4970124

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,688

This spacious custom 4 bed,3 bath home sits on 7 acres of land near the end of a dead-end country road and is minutes from the Village of Chester. Built in 2008, this home has ample storage, a large laundry room with a ¾ bath and a roomy primary suite with a custom tile shower, a Japanese soaking tub, and a private deck. The main level of the house has a large living room with brand-new flooring, a wood stove and stone hearth and sits adjacent to the gourmet kitchen featuring a commercial hood over the “Blue Star” 6 burner gas range and pot-filler faucet. The large open plan main level opens to the covered deck and 12 x 22 blue stone patio. On the same level is a large den/office which could be used as a 2nd living room, library or guest bedroom. While the living areas are spacious and comfortable the wrap-around porch is where you will want to spend all your time. This home was built in a controlled environment using 2 x 6 construction with plywood (not composite), copper piping, 10” basement concrete walls & radiant heat in the basement floor. The decking is low-maintenance Trex material and the siding is a high-quality vinyl. The grounds include several perennial gardens and a 6' deep pond. The basement level is just waiting for your imagination. Skiers, snowboarders, snowmobilers, or just an out door enthusiast be aware, this is an ideal property and location; less than 30 minutes to 3 major ski resorts, close to VAST snowmobile trail, and a short drive to the Chester!!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Dec 7, 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.

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656 Main Street Chester VT 05143

Chester, VT656 Main Street

Price$625,000

Est. Mortgage: $/month

MLS Number 4963158

  • Residential Single Family
  • Bedrooms 3
  • Construction Existing
  • Bathroom 3
  • Square Feet 3,040

Presenting the Walter Austin House, a 3+ bedroom, 2.5 bath Queen Anne style Victorian on .37 +/- acres in the Chester Village. This grand home has many period features and combines qualities from the Gilded Age with a more contemporary lifestyle. The first floor features a tiled mudroom, elegant foyer and spacious living room with an attractive gas marble fireplace. Pocket doors open from the living room to the large formal dining room. The efficient, classically styled kitchen has a breakfast bar, Corian countertops and accented glass-paned cabinets. The spacious great room with cathedral ceilings, skylights and radiant flooring has a palladium-crowned triptych window that showcases a pastoral view which delights year round. The second floor features 3 bedrooms and continues the elegance of the foyer with crown moldings and stained glass windows. A spacious bathroom with a clawfoot soaking tub and large tiled shower is located across the hall from the convenient laundry room with half bath. The finished third floor Aerie offers two cozy rooms for office and study or guest overflow. The grounds are lovely and feature a side deck with an awning off the great room, a private courtyard and a luxurious relaxing swim spa! In addition to the 1 car garage, a two story post & beam barn provides additional garage and workshop space with a second floor rec room or private office. Proximity to skiing, Chester Village Green and town rec area make this a wonderful primary or vacation home

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Dec 7, 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.

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83 Potash Brook Road Chester VT 05143

Chester, VT83 Potash Brook Road

Price$210,000

Est. Mortgage: $/month

MLS Number 4961980

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Square Feet 500
  • Acreage 15

This one is ready for you to do your thing! Convert the barn? Build a new home? Park an RV even! This pretty lot sits nicely between Chester and Andover, close to Okemo Mtn and has great access to paved and dirt roads not to mention the nearby Vast trails. The original house site has been levelled after a structure fire but a wonderful spring well, septic system, driveway, barns, and riverside access all remain. Perfect for a small horse farm, hobby farm or amazing campsite. Build your dream home, just pick your spot!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Dec 7, 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$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 and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Dec 7, 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: 7.03% last updated on Dec 7, 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
  • Bedrooms 3
  • Square Feet 1,824
  • Bathroom 2
  • Construction Existing

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: 7.03% last updated on Dec 7, 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$585,000

Est. Mortgage: $/month

MLS Number 4954753

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

This 3-bedroom house on 30+/- acres near Okemo, with a blend of artistry and environmental features, is a dream home in progress. The use of high-quality materials, sustainable construction, and off-grid origins make it unique. This home is so close to being finished, the new owner will get to personalize it and make it their very own. The house is ready to occupy so you could jump right in and enjoy VT living! The house, now grid-connected, boasts a Kohler generator, solar panels, cedar siding, and a standing seam roof. Inside, eco-friendly quartz countertops, an Italian LaNordica wood cook stove, and locally milled oak floors showcase the commitment to sustainability. The open main level includes a bedroom, office, full bath, and laundry. Upstairs houses two bedrooms, while the lower level walkout features a Morso wood stove and unfinished rooms. Additionally, the property includes an off-grid cottage with a kitchen, wood stove, solar panels, and loft. Priced for completion, it awaits a new owner to bring this masterpiece to life.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Dec 7, 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 December 8, 2023 7:54 AM EST