Chester, VT Homes For Sale | Vylla Home
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Chester VT Real Estate & Homes for Sale

16 Properties Found

The median home value in Chester, VT is $342,500. This is higher than the county median home value of $260,000. The national median home value is $308,980. The average price of homes sold in Chester, VT is $342,500. Approximately 57% of Chester homes are owned, compared to 20% rented, while 23% are vacant. Chester real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Chester real estate agent to arrange a tour today!
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1–16 of 16 properties displayed
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Beds:
9
Baths:
8.50
Sq.Ft.:
5,482
Status:
Active
MLS#:
5003697
Type:
Single Family
Lot size:
10.25 Acres
Year built:
1861
A broker reciprocity listing Courtesy: Daire Gibney - Barrett and Valley Associates Inc. Daire Gibney
View additional info

Discover a unique turnkey opportunity with this beautifully updated 1800's farmhouse, perfect for an inn, B&B, short-term rental or wedding venue. Recently renovated, the stunning home combines modern comforts with timeless charm, making it an ideal choice for both private and commercial ventures. As you enter, a grand staircase warmly welcomes you, leading to spacious interiors with original wide board floors. The property has been meticulously insulated and painted, giving it a fresh, contemporary feel. The serene landscape offers a perfect setting for a retreat, ski trip, or wedding. This property is offering 9 large bedrooms, most with ensuite bathrooms. The commercial kitchen, dining room, and separate owner's quarters enhance its functionality. Additionally, the Speak Easy,cozy library, and inviting sitting room offer numerous possibilities for creating a welcoming environment. Outside, the large 2000 sqft barn is ideal for a workshop, studio or event space. The property also features a large parking area, a tranquil pond, and open areas for tents to host weddings, all set on over 10 beautiful acres. The pond is surrounded by tranquil areas to sit and relax and nature watch. Whether you're looking to create a large family home, a thriving B&B, a ski club, or an artist retreat, this versatile property is just 10 minutes from Okemo Mountain and less than 10 minutes from the stunning Victorian village of Chester. Seize the day and invest in this Vermont heriloom home!

Beds:
3
Baths:
2.25
Sq.Ft.:
2,726
Status:
Active
MLS#:
5002963
Type:
Single Family
Lot size:
77.2 Acres
Year built:
2006
A broker reciprocity listing Courtesy: Christopher Cummings - Cummings & Co Christopher Cummings
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The Grafton Village Inn was the inspiration for this truly remarkable custom built colonial home, perfectly sited on 77 private acres on the outskirts of quaint Chester, VT. High quality craftsmanship is on display throughout this lovely home. The blue stone mudroom floor leads you directly through the stone archway into a chef's kitchen with custom Vermont soapstone sink, countertops and island gas range. Dine more casually in the kitchen, or in the adjacent formal dining room. The main floor plan is complete with a large living room with beautiful built in cabinetry and a gorgeous wood burning fireplace. The elegant stairway beckons you to the second floor where you'll find two spacious bedrooms, as well as a lovely primary ensuite with a soaking tub, double vanity and a huge walk-in closet. Continue through the walk-in closet to the bonus room over the attached 2 car garage. Complete with it's own wood burning stove, this would make an ideal studio or home office. The top level, or attic is beautifully finished and would make a terrific playroom, or studio space. The full basement offers excellent storage space, and the surrounding landscape is an outdoorsman's delight with over 2 miles of marked trails ideal for hiking, running, snowshoeing, XC skiing, mountain biking or just wandering. 75 acres are enrolled in the land use program offering significant tax benefits. Great views in a tranquil, seemingly rural setting just outside of downtown.

Beds:
4
Baths:
3.25
Sq.Ft.:
3,779
Status:
Active
MLS#:
5002063
Type:
Single Family
Lot size:
193 Acres
Year built:
1972
A broker reciprocity listing Courtesy: Suzanne Garvey - Mary W. Davis Realtor & Assoc., Inc., Off: 802-228-8811 Suzanne Garvey
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Design inspired by Frank Lloyd Wright this mid-century modern home is a beacon of tranquility for those looking for privacy. Surrounded by 193 acres including 13 acres of open pasture traced with ancient stone walls. Enjoy more than 2 miles of trails crossing brooks and fields. This magnificent haven for lots of wildlife has apple trees, raspberry bushes and more than 50 blueberry bushes. Inside a wide-open main living area and great room overlooks the 10 foot deep swimming pond, and the nearby stream can be heard from the deck or kitchen with the windows open. Step into the luxurious primary suite, a sanctuary with large windows and a spa inspired bath with a free-standing tub that boasts one of the best views from the house. Enjoy the newly renovated lower level with additional bedrooms and expansive family room. This area is ready for your touch and enjoys walkout access to the yard and pond. The 2nd level of the barn is currently a wood shop with wood-stove and a 2nd access from the road allows for storing large pieces or equipment on this upper level. The ground level of the barn has traditional sliding barn doors and extensive parking in front. Underground power and water lines travel from the house to a nearby site where another barn or horse arena could be built. A unique home treasure and like its organic architectural design the land has its own special quality of character and beauty. 193 acres are in the VT Land Use program. There is a 6 bedroom septic.

Beds:
6
Baths:
5.00
Sq.Ft.:
3,680
Status:
Active
MLS#:
5001473
Type:
Single Family
Lot size:
1,928.3 Sq. Ft.
Year built:
1819
A broker reciprocity listing Courtesy: T Story Jenks - LandVest, Inc/Woodstock T Story Jenks
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In Southern Vermont's Green Mountains, Owl Hill Reserve is a sanctuary spanning 1,928 acres, an expanse over twice the size of New York City's Central Park. Assembled over half a century, this land has united generations in the celebration of the great outdoors. At the heart of the reserve stands an 1800s brick farmhouse, a testament to earlier days of farming, complemented by two historic barns, a two-bedroom barn apartment and guest house. Surrounding the farmstead are apple trees, stonewalls and a spring fed two-acre swimming pond, creating a quiet retreat or jubilant family gatherings. A 3.5-mile private, gravel road meanders with the brook, unwinding through a carefully managed northern hardwood forest, predominantly Sugar Maple, home to a rich ecosystem including bear, moose, coyote, bobcat, and deer. The changing landscape includes exceptional mountain views and rolling meadows either cut for hay or used for grazing cattle. The clear waters of the brook beckon fly fisherman to cast lines. Cross country skiing, snowshoeing, biking, hiking and equestrian pursuits are all out the backdoor with endless trails to explore. A remote cabin near an apple orchard offers a place to immerse in nature or a place to write. Owl Hill Reserve is a legacy offering. It offers the luxury of simplicity, the wealth of nature, and the bond of family heritage. Less than 3 miles from the village center and skiing nearby: 25 mins to Okemo, 33 mins to Bromley. 2.5 hrs to Boston, 4.5 hrs to NY.

Beds:
4
Baths:
3.25
Sq.Ft.:
2,710
Status:
Active
MLS#:
5000203
Type:
Single Family
Lot size:
1.79 Acres
Year built:
1990
A broker reciprocity listing Courtesy: Daire Gibney - Barrett and Valley Associates Inc. Daire Gibney
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Nestled on a serene, quiet town maintained dirt road, this spacious home offers the perfect blend of tranquility and comfort. As you approach, you'll be captivated by the stunning long-range views that greet you from the expansive deck, a haven for relaxation and outdoor enjoyment. The deck overlooks a picturesque pond, not on the property but offering a beautiful, calming view that enhances the natural charm of the setting all the same. Step inside to discover a thoughtfully designed interior where ample space meets cozy. The large, finished basement is a true bonus, featuring a cozy and convientent propane stove and serving as an ideal games room or entertainment space for family and friends. Featureing 4 large bedrooms, 3.5 bathrooms, with large primary ensuite, large living room with views and that all enticing party or craft space in the below. This is equally a perfect vacation retreat or spacious family home. Conveniently located close to the popular ski areas of Okemo, Stratton, and Magic this home is perfect for winter sports enthusiasts. Whether you're seeking a peaceful year-round residence or a seasonal getaway, this property promises a lifestyle of serene beauty and endless recreational opportunities. Welcome home to your personal oasis.

Beds:
4
Baths:
2.50
Sq.Ft.:
2,772
Status:
Active
MLS#:
5000207
Type:
Single Family
Lot size:
32.97 Acres
Year built:
1860
A broker reciprocity listing Courtesy: Glenn Olney - Barrett & Valley Associates, Inc/Sprin Glenn Olney
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Until recently this was a working dairy farm and it certainly can be again. Or a horse farm! This 1860 farmhouse sits on 32 acres at the end of a town maintained road. 5 barns and outbuildings including a barn with cattle stanchions. Open meadows with river frontage and also a huge private pond. If you are looking for Vermont property with lots of Vermont charm, look no further than this beautiful property. Located in the peaceful town of Chester, just five minutes to the center of Chester and 10 or 15 minutes to Springfield shopping. Okemo Mountain is just 15-20 minutes away for great skiing and year-round activities! Several other ski areas are within a 30 to 45 minute drive.

Beds:
2
Baths:
0.75
Sq.Ft.:
960
Status:
Active
MLS#:
4998257
Type:
Single Family, Mobile Home, Manufactured Home
Lot size:
10.1 Acres
Year built:
1970
A broker reciprocity listing Courtesy: Amy L Vashaw - Twin State Realty LLC Amy L Vashaw
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Experience the tranquility of country living with this stunning 10.1-acre property. Enjoy breathtaking views, a fully functional septic system, and a drilled well. The property features a solid structure and 2.5 acres of maintained land, complete with a chicken coop, an apple tree, and blueberry bushes. Located in a quiet neighborhood, this land offers peace and privacy. Additionally, over 7 acres of untouched land with possible granite, providing potential for various uses. Don't miss out on this unique opportunity! Contact us for more details.

Beds:
3
Baths:
2.50
Sq.Ft.:
3,040
Status:
Active
MLS#:
4998244
Type:
Single Family
Lot size:
0.37 Acres
Year built:
1904
A broker reciprocity listing Courtesy: Geralyn Donohue - Engel & Volkers Okemo, Cell: 802-377-7096 Geralyn Donohue
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The Walter Austin House, a 3+ bedroom, 2.5 bath Queen Anne Victorian on .37 +/- acres in the Chester Village is a grand home that blends 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 marble gas fireplace. Original pocket doors open to the formal dining room. The efficient, classically styled kitchen has a breakfast bar, Corian countertops and accented glass-paned cabinets with a lovely picture window. The inviting Great Room has a cathedral ceiling, skylights and hardwood flooring with radiant heat and features a beautiful palladium-crowned triptych window overlooking the lovely pastoral view which delights in all seasons. The second floor features 3 bedrooms, a spacious bathroom with a clawfoot soaking tub and large tiled walk-in shower. The laundry room with half bath is across the hall and the finished third floor provides a quiet retreat with two finished rooms for office, study or guest overflow. The lovely, private grounds feature a deck with auto awning, a courtyard , a luxurious relaxing hot tub/swim spa, raised garden beds and established flower gardens. In addition to a one car garage, a two story post & beam barn provides additional garage and work space and a second floor rec room or office. Stroll to the Green or play Pickle Ball at the Rec area! Close to skiing, Summer theater, hiking and all the area has to offer. Showings begin on June 2nd.

Beds:
3
Baths:
1.75
Sq.Ft.:
1,735
Status:
Active
MLS#:
4997178
Type:
Single Family
Lot size:
29.57 Acres
Year built:
2021
A broker reciprocity listing Courtesy: Daire Gibney - Barrett and Valley Associates Inc. Daire Gibney
View additional info

This magnificent newly constructed home has it all! Located in the peaceful Popple Dungeon area of Chester, Vermont, you'll feel a million miles away from the world, nestled within 29 beautifully wooded acres along the South Branch of the Williams River. With just a short walk, you have over 1/4 mile of your very own stream to cool off in. There is no urban glow, little to no traffic, and the sounds of nature all around. The property features a picturesque pond, open pasture, and a par 3, 140-yard range for you to practice your golf swing. The oversized front deck and private deck off the living area provide several options for outdoor entertainment. The grill is hardlined for convenience and the deck is plumbed to add a gas firepit if you desire. Inside, you will find a meticulously designed and constructed home that is both modern yet classic. The living and gathering areas take advantage of the fully windowed facade, offering stunning views of the surrounding countryside from each level of the home. The everchanging views are enchanting at any time of year! The warm hardwood floors throughout, a kitchen island, central air, a standby generator, and a two-car garage truly make this a wonderful family home or vacation getaway. The forest land is enrolled in the Vermont Current Use Program and is managed by a local forester. All you have to do is sit back, relax, and enjoy your serene surroundings. Open House 5/25/2024 10.30PM to 2.30PM.

Beds:
4
Baths:
3.25
Sq.Ft.:
2,356
Status:
Active
MLS#:
4996384
Type:
Single Family
Lot size:
1.3 Acres
Year built:
1989
A broker reciprocity listing Courtesy: Julie Buffum - Buffum Realty Julie Buffum
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Luxurious contemporary home in a naturalized setting. Beautiful mountain views from family room and expansive deck. This home is a unique blend of country charm and modern convenience. Everyone will gather round the large center island in this amazing kitchen designed for cooking and entertaining. Open concept floor plan flows from kitchen to dining area and into the family room where you can set and take in the mountain views beyond. Slider leads to the deck combining indoor and outdoor living space. A private den is connected to the family room with French doors and can be opened up for addition living space or closed off for a quiet retreat. Second floor has three generous sized bedrooms, two of which are en suites. There is also a bonus room on the second floor that can be used for crafts, or additional den, home office or playroom. Wired for generator as well. Currently used as a family getaway and Airbnb. Home is located within minutes from year-round outdoor fun. Chester Recreation Center has a beautiful pool and lots of play area too. There are also local swimming holes, lots of hiking trails with lots to do. Just 18 minutes to the ski lifts at Okemo.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,008
Status:
Active
MLS#:
4996225
Type:
Multi-Family
Lot size:
0.75 Acres
Year built:
1850
A broker reciprocity listing Courtesy: Thaddeus J Abare - Barrett and Valley Associates Inc. Thaddeus J Abare
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Opportunity awaits! This three-unit property has been very well maintained with 2 long term tenants and 1 Vacant unit that has just been painted and is ready to be owner occupied or rented out. 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 as 2 rented storage units with great potential for new ideas. Even the basement is impressive as it has all been gone through. The outside of this home was just painted last year. All units are in good shape and fully applianced. This property also has a large in town open lot.

Beds:
2
Baths:
1.75
Sq.Ft.:
2,680
Status:
Active
MLS#:
4995602
Type:
Single Family
Lot size:
3 Acres
Year built:
1980
A broker reciprocity listing Courtesy: Daire Gibney - Barrett and Valley Associates Inc. Daire Gibney
View additional info

This charming home in Chester combines Vermont's rural charm with modern amenities. Surrounded by the serene beauty of Fox Chair Mountain, it offers an enchanting escape from daily life's hustle and bustle. Within the home, you'll find cozy spaces perfect for relaxation. From the inviting great room that opens onto a beautiful stone patio to the tranquil library, or the large private deck off the primary suite, and even the attached horse barn, there are several private areas to unwind and rejuvenate in this retreat. With two fireplaces and a wood stove, this home ensures comfort year-round. The modern kitchen is central to the flowing home and the porches and stone patio make gathering with friends and family a breeze whether it be an intimate dinner or a large crowd. The home's southern exposure over a stunning alpine valley provides endless opportunities to appreciate Vermont's natural beauty. With a rich history as a working farm, this property is ready for its next chapter. Additionally, beyond the 3-acre home site being offered is the opportunity to own a further 90+/- acres of stunning land with an outdoor riding arena, and perhaps an opportunity to create additional building lots. Whichever you choose you will find yourself poised for the enriching experience of living in this captivating haven. Don't miss the chance to create your sanctuary in Vermont. Schedule a viewing today and explore the possibilities of this pastoral paradise.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,702
Status:
Active
MLS#:
4994539
Type:
Single Family
Lot size:
0.89 Acres
Year built:
1850
A broker reciprocity listing Courtesy: Kimberly Matson - BHG Masiello Keene Kimberly Matson
View additional info

"Fully furnished! This home on .89 acres is located in the beautiful area of Gassetts in Chester, Vermont. Zoning is versatile and provides a wide range of options for commercial, retail, residential, or industrial use. Recent upgrades to the home include a brand new roof, siding, all new flooring, new kitchen cabinets and quarts countertops, new sheetrock and paint in the majority of the house, new sub flooring in the living room, laundry area, and mudroom, new window sills, new mini split, removal of all previous knob and tube wiring, replaced windows, new french door in the living room, new patio and fire pit area, freshly leveled and graveled driveway, two-car carport, refinished front deck, and freshly leveled backyard. This three bedroom, two bathroom home has an open concept as well as a traditional rustic ambiance with a beautiful modern touch. The three bedrooms are located on the second floor, with one bathroom being on the first floor as well as the second. The home is a mere 5 minute drive to the down center or about 8 miles to Okemo Ski Resort in the other direction. Hiking, mountain biking, and snowmobiling trails surround the town, making this home ideal for anyone who enjoys the natural beauty of Vermont. High speed internet is available (currently VTEL). LET'S MAKE A DEAL on LOT MLS# 4994538

Beds:
n/a
Baths:
Sq.Ft.:
4,060
Status:
Active
MLS#:
4990677
Type:
Multi-Family
Lot size:
0.25 Acres
Year built:
1820
A broker reciprocity listing Courtesy: Thaddeus J Abare - Barrett and Valley Associates Inc. Thaddeus J Abare
View additional info

Located at the head of the Village Green, it has been home to many successful businesses! The beautiful post and beam interior is warm and inviting. Enjoy the high foot and vehicle traffic in a very desirable area which has long benefitted owners and their businesses. There are 3 units with much potential! The first being the business store front, second is a space in the back which could easily be turned into a rental with a kitchen and separate bathroom, the third is a second floor 2bedroom 1 bathroom which has recently been updated with a freshly painted interior as well as new flooring and other updates. Along with the many benefits of this property's location comes parking right on the Green. Some recent updates are the back portion on the building has a new roof and solar was added to the whole building recently as well.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,728
Status:
Active
MLS#:
4986618
Type:
Single Family
Lot size:
1.12 Acres
Year built:
1980
A broker reciprocity listing Courtesy: Erin Kendall - EXP Realty, Phone: 802-579-5658 Erin Kendall
View additional info

Looking for the perfect ready to move in home in Vermont? Look no further than this French Provincial meets Vermont cabin centrally located in the quiet town of Chester, Vermont on Route 103. Within an hour drive to 5+ great ski mountains, within 10 minutes to Okemo mountain. House features so many great amenities and improvements--new black/grey roof just installed June 2024, new egress windows, beautiful indoor and outdoor fireplace, outside hot tub, beautiful stone patio, large private deck, 2 car garage, 4 bedrooms (but lots of room for more people), 2 bathrooms, a bonus bunk room, 2 extra lofts for an office or library, extra recreation room, and paved driveway. The house is a short distance to several beautiful lakes and state parks, mountains to hike, near the VAST trails, and interstate 91. Very spacious and also currently a great short term rental income property. And if you happen to lose power there is a 20kw stand-by propane generator ready to go. Call for a showing today!

Beds:
5
Baths:
4.00
Sq.Ft.:
4,186
Status:
Active
MLS#:
4972797
Type:
Single Family
Lot size:
3.21 Acres
Year built:
2023
A broker reciprocity listing Courtesy: Geralyn Donohue - Engel & Volkers Okemo, Cell: 802-377-7096 Geralyn Donohue
View additional info

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 to main panel in place. The first floor layout features a Great Room with 16' ceilings at its highest points, large kitchen which is a blank slate, a generously sized dining room with large picture window, a formal living room and full bath off the hall which could also be modified to a first floor en suite 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. 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. Motivated Sellers!

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Copyright © 2024 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 7/13/2024.

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