Chester VT
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Under Contract
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$319,000 | $118 per sq.ft.
Price Change! reduced by $160,000 down 50% on March 11th 2025
3590 VT 103 North
4 Beds | 2 Baths | Total Sq. Ft. 2702 | Acres: 0.89
Fully furnished! Thoughtfully upgraded home on .89 acres located in the beautiful area of Gassetts in Chester, Vermont. Easy access to I-91, 10 minutes to Okemo, 20 minutes to Magic Mountain, 30 minutes to Bromley, 40 minutes to Killington and under an hour drive to Stratton ski resort. This three bedroom, two bathroom home has an open concept. Two bedrooms on the second floor and one bedroom on the third floor. One bedroom on the second floor is a primary bedroom with a full bathroom. Large open area kitchen and dining room with plenty of room for storage, cooking and entertaining. Recent upgrades to the home include a brand new roof, siding, all new flooring, new kitchen cabinets and quartz countertops, new sheetrock and paint throughout, 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. 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). See
MLS Property & Listing Details & 26 images.
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Under Contract
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$329,000 | $113 per sq.ft.
198 Coach Road
4 Beds | 3 Baths | Total Sq. Ft. 2904 | Acres: 0.25
Imagine a home so inviting and comfortable, you'd never want to leave. Welcome to this practical and low-maintenance ranch-style home, perfectly designed for both relaxation and entertainment. Step inside and be greeted by the beautifully updated living room, bathed in natural light and warmed by a cozy wood stove--a haven during those chilly Vermont winters.This house isn't just a place to live; it's a space to thrive. The open concept kitchen and dining area, complete with a breakfast bar and ample cabinet space, serves as the heart of the home. Whether you're whipping up a family meal or hosting a casual brunch, this kitchen handles it all with ease.The practicality continues with three comfortable bedrooms on the main level alongside a full bathroom and primary ensuite. Venture downstairs to the fully finished basement, a dynamic space featuring an additional bedroom, a 1/2 bathroom, a media room, and a sizable office space currently set up as a gym. There is so much space you imagination can run wild with ideas for new uses.Maintenance is a breeze both inside and out, letting you spend more time enjoying your home and less on upkeep. The yard is just as manageable, ideal for those who appreciate outdoor space without the hassle.This clean, streamlined home is ready for you to make it your own. Don't miss out on this charming, expansive ranch--call today to schedule your viewing and start imagining your life here, where every day feels like a retreat. See
MLS Property & Listing Details & 29 images.
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$400,000 | $137 per sq.ft.
New Listing!
270 North Street
4 Beds | 2 Baths | Total Sq. Ft. 2919 | Acres: 0.5
Nestled in one of Vermont's historic locations, Chester's Stone Village offers timeless charm and rich character. This classic Federal-style home--featuring brick ends and a clapboard front--could be your next residence or vacation retreat. While this brick sided inviting 4-bedroom, 2-bath home isn't built of stone, it belongs to a rare collection of nine homes and a church constructed in the 1830s and 1840s by local masons using stone from nearby Mount Flamstead. The home maintains many of its original features while offering thoughtful updates including new roofing, upgraded electrical systems, and improved plumbing. The updated kitchen provides ample counter space and includes a charming breakfast nook or office area. You'll also find a formal dining room, a living room, and two additional spacious rooms. Upstairs, a beautifully crafted staircase leads to three bedrooms, a full bath, and a half bath. Highlights include wide board flooring, built-ins, and custom woodwork. Step outside to enjoy established gardens, blooming perennials, a hidden stone garden, a patio, and a fire pit--perfect for relaxing or entertaining. Located 12 miles from Okemo Resort, you'll have easy access to year-round activities including skiing, golfing, hiking, and snowmobiling. This unique Stone Village home is a 5 minute walk to a great local store known as Smitty's. Don't miss it--come explore Chester and the Okemo Valley community today. Taxes are based on town assessment. See
MLS Property & Listing Details & 58 images.
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$450,000 | $157 per sq.ft.
332 Hidden Heights Road
4 Beds | 3 Baths | Total Sq. Ft. 2868 | Acres: 3.21
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. See
MLS Property & Listing Details & 44 images.
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$488,888 | $283 per sq.ft.
Price Change! reduced by $186,112 down 38% on May 9th 2025
4877 VT Route 103
4 Beds | 2 Baths | Total Sq. Ft. 1728 | Acres: 1.12
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! See
MLS Property & Listing Details & 44 images.
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