Houses for Sale in 05143

Perched on 60 acres with views of Okemo Mountain from its second floor, this custom designed contemporary is hitting the market for the first time. Built by an international journalist and his writer wife as a retreat for their family and high profile friends, it now awaits its next lucky stewards. Filled with natural light, the rambling home was inspired by a friend's classic Vermont

Steve Stettler Four Seasons Sotheby's Int'l Realty

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

Immaculately maintained 2,700+ sq ft home offers privacy, peace, and mountain views—just 15 minutes to Okemo Mountain and 4 minutes to the village of Chester. Step inside to find an open, flowing layout with timeless and gorgeous Brazilian rosewood floors, a wood burning fireplace in the living room, and walls of windows that frame the landscape. The family chef will happily welcome opportunities

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

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

Magnificent Queen Ann Style Victorian with 3 bedrooms, 2.5 baths on .37 acres in Chester Village. The remarkable front porch has a beautiful archway and intricate, colorful ornamentation. A tiled entryway/coatroom leads to the elegant foyer with dramatic stairway and beautiful glass Art Nouveau Newel post light. The living room features a marble fireplace, pocket doors and original stained glass

Geralyn Donohue Engel & Völkers Okemo

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.

Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

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

This home on East Hill Road commands one of the area's best views all the way to Stratton! It is one of those spots where the view is different every day & spectacular! The home sits on 14 acres & it overlooks land protected by the Vermont Land Trust and mountains beyond. From the moment you enter, you won't want to leave. It is immaculate and ready to go. A large mudroom with a slate floor &

Betty McEnaney Diamond Realty

This lovely raised ranch is a sight to behold. Impeccably maintained by its current owners, this property is truly in move in condition. New architectural shingles and chimney work in 2016 along with a new furnace, and bathroom remodel in 2023, all you will have to do is sit back and relax on your private back deck enjoying nature. Nicely proportioned living room off the kitchen for easy

Jim Bialowski BHG Masiello Keene

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.

Tucked away on 31 beautiful acres in Andover is this lovely camp, cottage ready to be finished and enjoyed. The current owners have provided a great start with electric service, forced hot air heat and a finished living room to relax in. The land is a nature lover's dream with a year round stream in back of the camp, open area with a firepit and surrounded by a vast variety of trees on the

Gary Coger Four Seasons Sotheby's Int'l Realty

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

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 for an opportunity in an ideal location? This property offers unbeatable potential in the sought-after town of Chester. Located on a quiet country road, but still just a couple miles from downtown shopping and dining you get the best of both worlds. This property offers both open and wooded acreage with fruit trees to enjoy! Featuring two generously sized garages, this home is ideal for

Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

Prepare for an exhilarating mountain getaway at this enchanting four-bedroom chalet, nestled on a lush 2.1-acre estate in the heart of Andover. 2025 Ski season has been epic so far! Envision yourself minutes away from four renowned ski resorts, making this the perfect launchpad for your winter adventures. Immerse yourself in the local charm with easy access to the VAST trail network, offering a

Daire Gibney Barrett and Valley Associates Inc.

Escape to Moosewalk Lane, a fully furnished and equipped luxury estate in Andover, Vermont, set on 384 acres in the iconic Green Mountains. This one of a kind property offers a rare blend of seclusion, natural beauty, and timeless craftsmanship. The custom built 10,062 square foot main house features an expansive open concept design. Crafted with post and beam timber frame construction, the

Steve Stettler Four Seasons Sotheby's Int'l Realty

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.