Chester Vermont MLS Listings Homes For Sale

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CHESTER VT Home for sale $$370,000 | $137 per sq.ft.

$370,000 | $137 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $109,000 down 29% on October 2nd 2024

3590 VT 103 North 4 Beds | 2 Baths |   Total Sq. Ft. 2702  |  Acres: 0.89

"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 See MLS Property & Listing Details & 26 images.


Under Contract CHESTER VT Home for sale $$429,000 | $238 per sq.ft.

$429,000 | $238 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $15,000 down 3% on September 13th 2024

3057 VT Rte 11 East 3 Beds | 2 Baths |   Total Sq. Ft. 1800  |  Acres: 10.08

Unique Chester property on 10.08+/- acres with home business potential! This 3 bedroom, 1.5 bath Contemporary Saltbox has lovely grounds that feature a pond, landscaped rock gardens, a vegetable garden and ample open space for more gardening endeavors. The detached 3-bay garage offers multiple large spaces and oversized doors. Whether you are an artist, contractor, carpenter or mechanic, the high ceilings and huge amount of work space will be appreciated. Set back from the road with plenty of parking area, there is room to add more outbuildings for business needs. The efficient house features a cozy living room, first floor bedroom, full bath and kitchen/dining that opens to the back deck overlooking the private pond. The second floor has a large common area adjoined by two bedrooms and a half bath with laundry. The whole house generator and Fiber Optic internet service will keep your systems and business running during power outages. Commutable to the Upper Valley, convenient to Springfield, skiing, shopping, Chester Village and all the area has to offer. See MLS Property & Listing Details & 43 images. Includes a Virtual Tour


CHESTER VT Home for sale $$459,000 | $169 per sq.ft.

$459,000 | $169 per sq.ft. CHESTER VT HOME FOR SALE

491 Farrar Road 4 Beds | 4 Baths |   Total Sq. Ft. 2710  |  Acres: 1.79

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. See MLS Property & Listing Details & 35 images.


Under Contract CHESTER VT Home for sale $$599,000 | $197 per sq.ft.

$599,000 | $197 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $50,000 down 8% on September 13th 2024

656 Main Street 3 Beds | 3 Baths |   Total Sq. Ft. 3040  |  Acres: 0.37

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. See MLS Property & Listing Details & 56 images. Includes a Virtual Tour


CHESTER VT Home for sale $$648,888 | $376 per sq.ft.

$648,888 | $376 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $26,112 down 4% on May 29th 2024

4877 VT Route 103 4 Beds | 2 Baths |   Total Sq. Ft. 1728  |  Acres: 1.12

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! Added bonus is owner is willing to offer financing with 30% down payment to approved buyer. See MLS Property & Listing Details & 40 images.


CHESTER VT Home for sale $$649,000 | $242 per sq.ft.

$649,000 | $242 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $140,000 down 22% on October 15th 2024

686 Green Mountain Turnpike 2 Beds | 2 Baths |   Total Sq. Ft. 2680  |  Acres: 3

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. See MLS Property & Listing Details & 35 images.


CHESTER VT Home for sale $$699,000 | $297 per sq.ft.

$699,000 | $297 per sq.ft. CHESTER VT HOME FOR SALE

559 Davidson Hill Road 4 Beds | 4 Baths |   Total Sq. Ft. 2356  |  Acres: 1.3

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. See MLS Property & Listing Details & 27 images.


Under Contract CHESTER VT Home for sale $$699,000 | $373 per sq.ft.

$699,000 | $373 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $180,000 down 26% on October 16th 2024

994 Dodge Road 3 Beds | 2 Baths |   Total Sq. Ft. 1876  |  Acres: 26

Discover this extraordinary property, available for the first time! Nestled on 26 pristine, private acres at the end of a serene road, this 3-bedroom contemporary home is a true gem. Impeccably maintained by its original owners, every detail of this residence has been thoughtfully designed. The home features a welcoming entryway mudroom, a cozy sitting area leading into the dining space, and a spacious kitchen with a granite island, ample cabinets, and extensive counter space. The inviting living room boasts a wood-burning stove, while the main floor includes two large bedrooms, including an ensuite primary. The oversized loft provides the third bedroom and additional office space. Enjoy the expansive, covered wrap-around deck that seamlessly extends your living area outdoors. The property itself is a visual masterpiece with open spaces, exquisite stonework, and several matching outbuildings: an animal barn, an octagon chicken coop, a 2-car garage, and a large storage barn that could easily be transformed into a workshop. Conveniently located just a few miles from town, major ski resorts, and Rt 91, this property offers everything Vermont has to offer. This is truly one of Chester's finest properties -- don't miss this rare opportunity! See MLS Property & Listing Details & 40 images. Includes a Virtual Tour


CHESTER VT Home for sale $$725,000 | $132 per sq.ft.

$725,000 | $132 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $174,999 down 24% on August 20th 2024

665 Route 10 9 Beds | 10 Baths |   Total Sq. Ft. 5482  |  Acres: 10.25

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. Motivated Seller is offering Owner Financing. See MLS Property & Listing Details & 37 images.


CHESTER VT Home for sale $$995,000 | $359 per sq.ft.

$995,000 | $359 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $4,000 down 0% on July 29th 2024

157 Thompson Road 4 Beds | 3 Baths |   Total Sq. Ft. 2772  |  Acres: 32.97

Welcome to this beautiful historic farm dating back to 1825. At one time known as the Thompson Farm, in 1995 it was purchased by the current owner who lovingly restored it to its former glory. In 1999 it became the "Jersey Girls Farm". Attention was given to retain all of the antique charm, including keeping the original slate roof on main house, all original doors and original wide board floors. The house was also modernized with conveniences such as a new heating system, new wiring, new windows (retaining the original design), and a full array of solar panels to make the house fully self-sufficient. You will find plenty of room and charm inside, beginning with the large country kitchen which includes a working antique Glenwood stove. There's a huge pantry which doubles as a laundry room. The dining room, living room, library, one bedroom, and spacious 1/2 bath complete the downstairs living area. On the second level are 3 large bedrooms and a full bath in the main structure. The expansive master suite even has a spa tub! This room has a 2nd stairway which leads you back to the kitchen. On almost 33 acres of open and wooded land, all of which sits at the end of a town-maintained road. There's a large pond for swimming, fishing, or even kayaking. 5 outbuildings including a nice 1800's 30 x 80 barn! Endless possibilities: small dairy or horse farm, Airbnb, or bed and breakfast. Just 5 minutes to Chester. Shopping, hospital, skiing at Okemo, I-91 - all within 15 - 20 minutes! See MLS Property & Listing Details & 50 images.