Chester Vermont homes for sale starting at Fifty Thousand Dollars

$1,125,000 - Chester, VT

1502 Popple Dungeon Road Chester, VT - Welcome to paradise! Enjoy all four seasons in this handsome, 1989 colonial-style home with modern amenities. From the covered porch, relax and take in views of the front gardens and your land across the road with apple trees and brook frontage. A large solar array is tucked out of sight producing all the power you would need. Behind the house is a fenced-in garden and greenhouse, a couple of useful sheds and a large, fenced pasture bordered by a brook. Off to the side are two livestock barns and a new 24’ x 48’ equipment shed. If you have use for a large studio space, you are in luck. Above the 2-car garage is a suite outfitted with a kitchen, ¾ bath, and a large open room with fiber internet, perfect for working, writing, creating art, or exercising. Saving the best for last, the home is just lovely. The dream country kitchen with high end appliances and custom tile is open to the sitting room with fireplace. The dining room enjoys the wall of windows overlooking the back acreage. There is a den with closets and ¾ bath, and second living room with French doors to the porch. There is a large, functional mudroom for all your gear. Upstairs is the primary suite with steam shower and two very generous bedrooms and another renovated bath. Located 3.5 from the town green on a paved road, and close to 3 ski resorts, this unique property provides a wonderful place for living, working, or vacationing. View the video tour and look at the attachments for all the recent improvements.

$689,000 - Chester, VT

31 Palmer Road Chester, VT - Rivers Edge Farm is an absolutely diverse agricultural property which serves bovine, equine and many other farm animals currently and in its past history. 22+ organic acres of rich river bottom land yields a robust crop of haylage, corn or hay or whatever suits your needs. The buildings are mixed use for the owners. Some are animal occupied and feed storage and one is a large garage/workshop that any mechanic would covet. The home is as warm and welcoming as you can get with an updated kitchen, wood floors and a foyer with individual cubbies for occupants to claim as their own. 3 large bedrooms on the second floor and an option for a first floor bedroom vs a playroom exists. Keep the weather and earth outdoors with your covered porches surrounding most sides of the home. Enjoy the river with a seasonal swimming hole under the railroad bridge and there's even a tiny house for those city folk who want a taste of country life. The current owners also sell meats and eggs. Lots of income generation can be gained at Rivers Edge Farm. Come see the potential for yourself!

$669,000 - Chester, VT

31 Palmer Road Chester, VT - This is not your typical Vermont farmhouse—it’s far better. Surrounded by rolling fields and pastoral views, this beautifully updated home combines classic country charm with modern ease. Inside, you’ll find a warm, sunlit layout anchored by a stunning chef’s kitchen featuring high-end Viking appliances, granite counters, and custom cabinetry. The spacious primary suite is a luxurious retreat, offering peace, comfort, and incredible storage. A flexible floor plan adds to the home's appeal, with a first-floor bonus room—currently a playroom—offering potential as a guest suite or private bedroom, complete with its own covered deck overlooking the fields. Outside, the property is built for both lifestyle and purpose. A 4-stall horse barn with run-in, large cattle barn, oversized workshop, and detached 2-car garage make it ready for your dreams—be it hobby farming, equestrian living, or simply room to roam. A charming one-room cabin tucked in the treeline is perfect for guests, creative space, or glamping. All located in the heart of Vermont ski country—just minutes from Okemo, with easy access to Stratton, Bromley, and Magic. Whether you're looking for a forever home, a modern homestead, or a lifestyle upgrade, this one-of-a-kind property offers beauty, function, and endless inspiration.

$649,000 - Chester, VT

656 Main Street Chester, VT - 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 picture window. A formal dining room is ready for entertaining as is the well-appointed timeless kitchen with breakfast bar and a large picture window. The elegant great room is a wonderful living space and features skylights, radiant flooring and a dramatic Venetian window overlooking a lovely view in all seasons. Full length glass sliders lead to a side deck with automatic awning for evening sunset meals. An oversized swim spa/hot tub overlooks the meadow beyond and is a great place to unwind! The second floor has 3 bedrooms, a large bath with a clawfoot soaking tub, walk-in shower and a laundry room with half bath. A finished third floor provides office space, storage or room for overflow guests. The house has been thoughtfully outfitted with a dual heating system. In 2000 a barn/garage was constructed with a second floor for hobbies or additional office space. The lovely fenced in yard has garden space and perennial gardens and a lovely maple tree with a perfectly shaped crown. Walk to the Chester Commons, town recreation area and enjoy all that Chester has to offer!

$599,000 - Chester, VT

534 Elm Street Chester, VT - Have you been waiting to buy just the right property? An impressive home in a special town in an amazing state might be perfect. This well-loved Victorian has 4 bedrooms in the main house and another 3 bedrooms in the carriage house unit. There is a storage room in between the two spaces with doors to open to easily connect the units. The beautiful main house has a farmhouse-style kitchen, formal dining room for holiday dinners, 2 connecting living spaces with fireplace, a bedroom and a full bath. Upstairs are 3 more bedrooms and a full and half bath. The character and antique doors and trim make this house a home. The carriage house unit has 3 bedrooms, a kitchen and full bath and a large open great room and is perfect for guests. There are also more areas with potential - two more levels of barn space plus the attic. Outside you will find a large covered porch, a level back yard for games, and the Williams River down at the back of the property. Sold turnkey. Be the 4th family to own this home since 1868 and see why Chester has been voted one of the top 10 most beautiful towns in Vermont! Discover the tasty food options, pubs, antique shops, art galleries, yoga & pottery studios, and a country market with great sandwiches, fresh meats and produce. Experience Vermont - hiking trails, world class skiing, farms, refreshing rivers, restaurants, breweries and more. Be close to the best of Vermont's ski resorts! (Okemo, Killington, Stratton, Bromley, and Magic Mountains).

$595,000 - Chester, VT

525 Route 103 N Chester, VT - 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 love, and this property is looking for that person who can bring it back to its former glory days. As they say, the buildings have good bones, so consider this a blank canvas to do whatever you please for renovations. Since it's very original, you can update without having to tear out former "improvements" that might have taken away the antique charm. Since it was a working farm at one time, it still has the old silo. Years ago, this was made into a 4-level living unit. You can bring this back to life and use it as a very unique vacation rental or keep it as a very cool place for your kids and grandkids - much cooler than a treehouse! The attached barn is huge and for years it was used as a barn antique store. You could do that again, or you could use it for animals. With the open land which supplies a big supply of hay each year, this property would be great for horses, cows, and other large animals. There is also a sugar house, plus a separate building out front that was also used for the antique business. Several apple trees, a huge rhubarb patch, and more! Don't wait on this one!

$499,000 - Chester, VT

472 Main Street Chester, VT - The Laurin Whiting House, circa 1850, is a Greek Revival style home with 5 bedrooms and 7 baths on 1 +/- acre. The curved, multi-bay veranda wraps around the front of the house with neo-classical columns and an oculus that punctuates the front gable end. A light-filled living room has French doors that open to the lovely porch and adjoin a large bedroom and full bath. The formal dining room connects with the eat-in kitchen with side entrance. An elegant foyer staircase leads to the large landing area on the second floor and a large, ensuite primary bedroom. A third bedroom adjoins a full bath and connects to a back stairway and two additional bedrooms and a bath. The convenient mudroom with adjoining half bath and laundry room connects the house to the barn/event space. The original barn is redesigned to function as a conference center. The meeting space has a separate bar area, two half baths, a tv/game room with exposed beams and a second floor billiard room. The potential uses for this multi-faceted property are many- a spacious full-time home with a business, a duplex, vacation home, ski club or an investment property with rental potential. A large, level yard offers space for gardening, badminton or croquet and a back deck for enjoying summer evenings. Walk to the Town Green for Summer Concerts, shopping and festivals and to the Town Rec area around the corner for year-round exercise and fun!

$450,000 - Chester, VT

4877 Vt Route 103 Chester, VT - Tucked along the scenic curves of Route 103 & surrounded by the rolling beauty of Chester, Vermont, this unique French Provincial–meets–Vermont cabin is more than just a house—it’s an invitation to breathe deeper, slow down, & reconnect with the rhythm of nature. Wake each morning to the soothing sound of a nearby creek & the scent of fresh mountain air drifting through the trees. Step outside with your coffee & feel the day begin gently, with birdsong & the promise of adventure all around you. Inside, the home blends rustic charm with modern comfort. A spacious living room welcomes you with its wood-burning fireplace—the perfect gathering place after a day on the slopes or exploring the nearby trails. The main floor also features a private master bedroom & a three-piece bath, creating a quiet corner for rest & retreat. Upstairs, three cozy bedrooms offer peaceful views of the surrounding woods, while two inviting lofts provide just the right nooks for curling up with a book or watching your favorite films. A separate recreation room gives everyone space to spread out & make their own memories. Outside, life continues in every season: soak under the stars in the outdoor hot tub, grill with friends on warm summer evenings, or toast marshmallows at the dual fire pit. Recent upgrades- a brand-new roof (June 2024), A/C, a 20kW standby propane generator, & new egress windows, you can settle in with comfort & confidence. This home is ready to be the backdrop for your next chapter!

$440,000 - Chester, VT

332 Hidden Heights Road Chester, VT - This charming multi-level home provides 4 bedrooms and a variety of places to find private space for quiet. Also a large open recreation room which includes a full size pool table/table tennis table and dry bar. Located just 3 miles from the charming Town of Chester. An easy drive to Bromley Mt, Magic Mt and Okemo, this makes a great home for an active family. Beautiful views from the deck provide a great place for morning coffee and an evening watching the stars. There is plenty of space for gardens and outdoor activities as well as wooded land to spend relaxing time in. House has automatic whole house propane generator. There are two firemen that live on the road, so it is always well plowed and maintained.

$425,000 - Chester, VT

196 North Street Chester, VT - The Simeon Sherwin House, built in 1844, is one of three look-alike houses known as "Three Sisters". The house was owned by Olivia Goldsmith in the 1990's who wrote The First Wives Club. Her worldly, vibrant imprint is still evident in many of the home's unique features. Architecturally, the stone exterior is unique with large blocks (quoins) of schist and mica at the corners. Inside, there is a delightful three season sunroom and formal dining room with woodstove insert, chandelier and an array of full light doors which open to the large, bright kitchen and first floor full bath. A sitting room with a double-sided fireplace connects to the spacious living room. The inviting foyer leads to the second floor which features 3 bedrooms, 2 baths and a sitting room. An addition added by the author and named the Queen's Room during the current owners bnb tenure features built-ins, a partition wall with transom window and a wood stove insert flanked by cozy built-in seats. The primary bath features gold-plated fixtures, a skylight and soaking tub. The first floor also has a heated, retail space for a home business with a separate entrance and office above that has served as an antique shop. The two-car attached, garage has unfinished, overhead space. The exterior needs some sprucing up and a new owner will want to add cosmetic upgrades. The property on .70 acres has a lovely yard with a hydrangea bush, charming bridge, small pond and stone bench overlooking the picturesque village.

Chester, Vermont listings for sale

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