Chester, VT Houses for Sale

The Stone Cottage began its long history as a schoolhouse built as the Civil War was nearing its conclusion in 1864. Scottish craftsmen from the Aberdeen region constructed the sturdy structure using a technique referred to as 'snecked ashlar' with hewn ashlar stones laid in horizontal and vertical courses with spaces filled with smaller 'snecks joined with mortar. The random patchwork yields a

Laird Bradley Williamson Group Sothebys Intl. Realty

Escape to your own private Vermont retreat in this classic 1980s chalet set on 13+ acres in a serene, park-like setting. Tucked back from the road yet convenient to local amenities, the home offers three levels of living space with five bedrooms and three baths. The lower level features a second kitchen and living area perfect for guests or young adults. In summer, enjoy the best of country

Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of

Joseph Karl William Raveis Real Estate Vermont Properties

Charming Renovated Farmhouse in the Heart of ChesterThis beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway.Inside, enjoy a spacious kitchen with custom

McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

This immaculately maintained 2,700+/- sq ft- four-bedroom home with privacy, peace, and mountain views—just 15 minutes to Okemo and 4 minutes to Chester Village. The open layout features Brazilian rosewood floors, a Lopi wood-burning fireplace, and walls of windows showcasing the landscape. The chef’s kitchen offers quartz countertops, Wolf Range, Sub Zero refrigerator, and Bosch dishwasher. The

Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some

Glenn Olney Barrett and Valley Associates Inc.

Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances.The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious

Robin Apps Four Seasons Sotheby's Int'l Realty

Welcome to Silver Birches — a serene Vermont retreat nestled on 27 acres along a quiet country road, perfectly situated Grafton and Chester villages. Sprawling ranch-style home offers a fantastic floor plan with generously sized rooms and a natural flow, making it ideal as a year-round homestead or a peaceful getaway. The open-concept kitchen and dining area, complete with a cozy fireplace and

Jessica Landers Barrett and Valley Associates Inc.

Historically known as the Frank Harris House, this distinguished circa 1880 Queen Anne style Victorian commercial building on .75+/- acres has long been a landmark presence in the village of Chester. With its welcoming veranda and timeless charm, the property has served as a thriving office for many years and has many period architectural details throughout such as, a unique, colored transom

Geralyn Donohue Engel & Völkers Okemo

The view from the road does not give you the fact that behind the house is a beautiful and private backyard! This property has great possibilities for you to create your own vision of what it can become. You could either do some improvements to the existing gambrel structure which has been a comfortable residence for many years, or you could use it as some kind of allowed business or rental and

Glenn Olney Barrett and Valley Associates Inc.

This wonderful home has so much to offer! This property has many great features including a brand new roof just put on this summer, great large windows allowing nature light into the living space, a very large oversized Two car garage which also has a magnificent workshop with 220 electric already hooked up, wonderful garden areas with flowers and bushes and so much more! The property also

Thaddeus Abare Barrett and Valley Associates Inc.

Everything you’ve been looking for in a Vermont home—completely renovated with care and character. Nearly every aspect of this Chester property is new: electrical, plumbing, heating, insulation, drywall, windows, and more—offering the low-maintenance peace of mind homeowners crave. The kitchen features a stylish farmhouse sink and stone countertops, while the upstairs bathroom includes a

Betsy Adamovich Real Broker LLC

Until this last winter this was a really sweet 16 x 24 log cabin. Then it became fire damaged and now the owner would love to have someone bring it back to its former glory. Nice, private area on a town-maintained country road. All utilities are underground, including a 330-gallon propane tank, electric power from the street, and water from the 230' drilled well. The cabin has 1 bath, a

Glenn Olney Barrett and Valley Associates Inc.

Adorable Village Home in the Heart of Chester, VermontThis charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage.Inside, you’ll love the warm, inviting living space with

Rachael Rogala Rachael Rogala Inc.

This Cozy cabin tucked away along the outskirts of Chester is sure to impress. With a brand new roof, heating system and more this is the perfect turn key retreat. The property features both open lawn and forest to explore, just up the road from snowmobiling and hiking trails this property has the ability to be your home base for all your favorite activities year around. Including close proximity

Thaddeus Abare Barrett and Valley Associates Inc.

Skygate Farm is a historic Vermont farmstead first settled in the 1800s, which today spans over 300 acres of meadows, forests, trails, and weathered stone walls. The setting speaks of an early farmer’s wisdom — sited along a gentle hill to shield against the northwest winds, while opening to the first light of day and the vast mountain views to the east. Found at the end of a winding gravel road,

Dia Jenks LandVest, Inc/Woodstock

Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system,

Joe Castaluccio Winhall Real Estate

With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful; uniquely situated on 20 acres of gorgeous greenlawn, fields, forest, rolling hills, extensive stone walls. A mere 2 miles to Chester. Since 2020 the house has been transformed & restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel

Gary Coger Four Seasons Sotheby's Int'l Realty

Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

Joshua Lemieux Remax Summit

Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep.Inside, the home is open and inviting, with plenty of room to relax or

Daire Gibney Barrett and Valley Associates Inc.

Looking to live near the Chester Green? This may be the home for you! Currently used as a four-unit apartment building I believe that the highest and best use would be to return it to a single-family home with one accessory apartment in the back. The house is in need of renovation however, the style and location would lend well to that investment, or renovate the four units as your next venture,

John Tolosky Barrett and Valley Associates Inc.