- Chester VT Homes $250000 to $500000
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Viewing 1 to 13 of 13 listings
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- New Listing!
$250,000 | $219 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 1140 | Acres: 0.25 CHESTER VT
View Details & 20 images
Description:There’s something quietly reassuring about a home that’s stood the test of time—and this classic dormered Cape in Chester delivers just that, with a clean, updated feel that suits today’s lifestyle. Built circa 1945, the home offers three comfortable bedrooms—including a convenient ground-floor bedroom—and 1.5 baths, giving you flexibility for guests or single-level living. The layout is practical and easy to live in, and the enclosed rear entry porch adds everyday function—perfect for muddy boots, groceries, or easing into the house after a long Vermont day. Out back, the porch doubles as a relaxed hangout space, or step out onto the sun-filled deck for a bit more light and fresh air. It’s an easy, inviting setup for morning coffee or winding down at the end of the day. Downstairs, a full basement provides solid storage or workspace potential, while the detached two-car garage—with workshop space and automatic openers—offers flexibility for projects, hobbies, or extra gear. The paved driveway, standing seam metal roof, and straightforward systems like the oil-fired hot water setup all point toward low-maintenance ownership—something buyers appreciate more and more. The home is being offered with key appliances already in place, including an electric range, refrigerator, microwave, washer, dryer, and dehumidifier, making for an easy transition whether you’re just starting out or simplifying your next chapter. Set in one of Southern Vermont’s most loved villages, this is the kind of property that works just as well as a first home as it does for downsizing. Simple, solid, and well-located—if Chester’s been on your radar, this one’s worth a closer look before it slips by.
- Under Contract
$269,000 | $230 per sq.ft. | 3 Beds | 1 Baths | Total Sq. Ft. 1168 | Acres: 0.5 CHESTER VT
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Description:This cozy gambrel style home tucked away on a nice level 1/2-acre lot just on the outskirts of Chester village offers lots of yard space, lots of storage space and is an easy keeper. This cute home offers hardwood floors on the first floor, has lots of natural light, an enclosed porch that could work as a home office, dining area, mud room or just a place to hang out. 2nd floor features three bedrooms with the primary leading out to a deck overlooking the yard. Nice high ceilings on the second floor make the rooms very open and bright. There's an attached storage room allowing room for freezers, storage or a second mud/entry room. Large 2 bay garage with second floor storage, a side shed that would be perfect for a garden shed and a separate space for lawn and snow blowers. The owners have done lots of upgrades, including a full house generator. So, if you are looking, be sure to add this home to your list.
- Under Contract
$270,000 | $263 per sq.ft. | 2 Beds | 1 Baths | Total Sq. Ft. 1026 | Acres: 0.32 CHESTER VT
View Details & 37 images
Description:Not your cookie cutter home, this charming 2 BR home is located on the outskirts of Chester. One floor living for those wanting an easy keeper and carefree living. Hardwood floors throughout, large living room, formal dining room, galley kitchen and 2 roomy bedrooms. And let's not forget the spacious breezeway/entry. This area is perfect for hosting a gathering of friends and neighbors under shade or away from summer rains. Current owners have spent three years developing extensive perennial beds ensuring that there is always a flower in bloom. Along with perennials, owners have added lots of specialty trees-hardwood and fruit trees and bushes along with raised and in-ground beds and a new garden shed to store your tools. All this and there is still lawn to play on.
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$289,000 | $196 per sq.ft. | 2 Beds | 3 Baths | Total Sq. Ft. 1475 | Acres: 9 CHESTER VT
View Details & 14 images
Description:Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided from the parcel across the street and they may be purchased together. See MLS #5069927 This is a nice level to rolling lot with some open and some woods, has a 2 car garage, 2 enclosed porches and is well put together inside. The outside needs some finish work, so not likely to go a federal program. With some TLC this will be a fab get away. The town maintains the road to the house...such a benefit! This is a must see for location
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Price Change! reduced by $70,000 down 21% on May 6th 2026
$329,000 | $221 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 1488 | Acres: 0.25 CHESTER VT
View Details & 29 images
Description:Welcome to your dream home – This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by the gorgeous hardwood floors that add warmth and character to every room. Bask in the great natural light that fills every corner of this lovely abode, making every day feel bright and inviting. This home includes a main level bedroom, dining room and family room. In addition there is an attached garage and a barn for all your hobbies. This home is perfect for families and outdoor enthusiasts alike. Imagine being just a short stroll away from the village store for all your essentials and enjoying nearby skiing adventures in winter, along with shopping and restaurants year-round! Don't miss out on this incredible opportunity to own a piece of paradise in the heart of it all! Schedule your visit today and get ready to fall in love – your perfect home awaits!
- Under Contract
$340,000 | $162 per sq.ft. | 3 Beds | 1 Baths | Total Sq. Ft. 2096 | Acres: 1.69 CHESTER VT
View Details & 55 images
Description:Welcome to a charming village retreat in the heart of Chester, perfectly situated on Main Street in the historic Chester Stone Village. This inviting home blends classic Vermont character with comfortable, year-round living. Enter through a practical mudroom with ample space for all your seasonal gear—ideal for embracing Vermont’s four-season lifestyle. To the right, at the front of the home, you’ll find a bright and open living space featuring a spacious kitchen with a large island, seamlessly connected to the dining area and living room. A glass door leads to a covered porch, creating the perfect spot for morning coffee or relaxing evenings. The main level also offers a dedicated office, a full bathroom, and a convenient laundry room. Toward the back of the home, two bedrooms provide comfortable accommodations, and a stunning family room showcases vaulted ceilings, exposed beams, and walls of windows that fill the space with natural light. A glass slider opens to the back deck, where you’ll find an above-ground pool—perfect for summer enjoyment. Experience the charm of Vermont living in this village home, just moments from local shops, dining, and all that Chester has to offer. Visit the Okemo real estate community today. Taxes are based on town assessment.
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Price Change! reduced by $100,000 down 29% on May 7th 2026
$349,000 | $195 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 1788 | Acres: 3.3 CHESTER VT
View Details & 31 images
Description:Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for—flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved road leads you home, winding past back woods and pastoral farmland before arriving at the property. The elevated deck becomes your front-row seat to the landscape below—perfect for morning coffee, summer dinners, or simply listening to the brook roll past. Inside, the home feels warm, functional, and comfortable. A large living room is anchored by a substantial woodstove that brings real Vermont heat and atmosphere through the colder months. The sunroom is a standout space, wrapped in windows and overlooking the brook, creating a peaceful place to read, work, or relax. From here, step directly onto the deck and into the outdoors. The layout offers three bedrooms and two bathrooms, including a ground-floor bedroom for easy everyday living. Storage is abundant throughout, making room for outdoor gear, tools, and seasonal equipment. The land itself adds real value. With acreage on both sides of the brook, there’s room to garden, explore, build trails, or simply enjoy your own stretch of water and woods. The surrounding countryside delivers classic Vermont scenery—rolling fields, forested hills, and quiet country roads. Located just minutes from the village of Chester and close to Okemo, Stratton, and Magic Mountain, this is a true four-season basecamp for skiing, hiking, biking, fishing, and exploring Vermont’s natural beauty. A property that offers privacy, water frontage, land, and mountain access—without giving up convenience.
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$349,000 | $105 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 3332 | Acres: 2 CHESTER VT
View Details & 39 images
Description:Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting on the front porch and listening the soft rustle of the willow tree leaves and the babbling brook trickling by, then you step inside and feel that you have walked into a home that was truly loved. The large kitchen offers nice upgrades including tile floor, granite countertops and appliances. The main level offers a bedroom, dining room, office space and living room. All of the windows have been replaced (except in the attic), updated electric panel, insulation done by Efficiency VT, new stoves in the barn room and living room (see MLS docs for the complete list). This property is perfect for anyone looking for a TRUE Vermont home with loads of potential. Great natural light, large bedrooms, hardwood floors and attached garage. One of the features I personally love is the screened stone patio (barn room) off the back of the house. The rustic beams and barn boards with wood stove is a wonderful space to relax and entertain. Above is unfinished space ready for your ideas, work out space? yoga studio? game room? There are pretty perennials and gardens surrounding the home. The back yard is private with attached shed space and back deck. Chester is a wonderful community and this home is perfectly situated for easy access to I91, Grafton, ski resorts, shopping and walking to the village green. The sellers have loved owning this home and have created many many memories here. Don't miss your chance to be the next stewards of this truly special property.
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$390,000 | $299 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 1304 | Acres: 1 CHESTER VT
View Details & 51 images
Description:Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that’s hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates. Refinished wide plank floors bring warmth throughout, while the kitchen features granite countertops and a farmhouse sink. Upstairs, a vintage Martini pedestal sink adds a distinctive, curated touch to the bathroom. Outside, the level lawn provides usable space for everything from gardening to entertaining, and the substantial post-and-beam barn opens the door to a wide range of future uses, storage, workshop space, or potential expansion. Located just minutes from Chester’s Stone Village, the Grist Mill, and Smitty’s Market, and within easy reach of Okemo, Bromley, Killington, Stratton, and Mount Snow, this is a strong option for both full-time living and recreational use. Currently used as a long-term rental and previously operated as a successful Airbnb and personal vacation home, the property offers flexibility for a variety of ownership goals.
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$399,000 | $186 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2148 | Acres: 1.5 CHESTER VT
View Details & 37 images
Description:This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of living space 4 bedrooms, 2.5 bathrooms. It sits on the banks of the Williams River on a dead end street and treed backyard area. First floor consists of a large kitchen and livng room and a half bath. The second floor has a beautiful sized primary bedroom with ensuite bathroom. There are also 3 bedrooms and a 3/4 hallway bathroom.
- Under Contract
$425,000 | $214 per sq.ft. | 5 Beds | 2 Baths | Total Sq. Ft. 1982 | Acres: 0.27 CHESTER VT
View Details & 43 images
Description:The Best of Both Worlds: Modern Comfort Meets Village Charm! Discover the perfect blend of contemporary upgrades and serene neighborhood. This meticulously updated raised ranch offers an expansive layout designed for both effortless entertaining and comfortable daily living. Step inside to find a light-filled open-concept living and dining area, anchored by stunning hickory hardwood floors that flow throughout the main level. The heart of the home is the fully renovated kitchen, featuring modern finishes, apron front farmhouse sink and outfitted with stainless steel appliances. With 5 spacious bedrooms, 2 updated bathrooms, there is no shortage of space. Enjoy cozy evenings in the living room featuring a vaulted ceiling and exposed wood beams and a gas fireplace. The primary suite serves as a retreat complete with a private balcony, and an ensuite bath featuring a double vanity. On the lower level, a large bonus room provides the flexible space you’ve been looking for-ideal for a gym, playroom or office! Enjoy the fresh air without the bugs in your screened-in porch, or host summer gatherings in the peaceful yard. Located on a quiet dead-end street, this home offers privacy while remaining incredibly convenient. Additional highlights include an easy walk to the vibrant Chester Green, peace of mind with a new boiler in 2021, freshly painted interior in 2022, sump pump installed in 2023, a 1 car garage, a paved driveway done in 2024, and new windows installed throughout most of the house in 2025. Don't miss your chance to own this move-in-ready gem in a prime Chester location!
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Price Change! reduced by $20,000 down 4% on May 12th 2026
$479,000 | $363 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 1320 | Acres: 10.86 CHESTER VT
View Details & 60 images
Description:MOTIVATED SELLERS welcome you to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, direct access to VAST, located less than an hour from six renowned ski resorts and amenities. So many updates in the past two years; fully remodeled kitchen and bathrooms, fresh paint, new flooring along with numerous updates (list attached in associate documents); modern and cozy with so much charm! Nestled on over 10 acres, you will find walking trails, a fire pit and outbuildings on premises. Vaulted ceilings, open floor plan, lots of natural light and natural woodwork, this is a true move in ready beauty. The owners are leaving this home furnished; equipped with designer and custom furnishings, some locally made custom art work, alongside linens and high end kitchen items making this a true turnkey property. The rooms are nicely sized and in close proximity to bathrooms. This has been used as a vacation property and has a history of successful Airbnb. The wood burning fireplace brings a feeling of serenity on those chilly days. Fiber internet on site for those that work remotely. Town records state two bedrooms, however, the loft area has an en suite with a full bathroom and lots of closet space! Plenty of storage, full walkout basement gives ample space. This is one of those properties you won’t want to miss on your home buying adventure! Truly a stunning property with so much to offer!
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$479,000 | $179 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2676 | Acres: 2 CHESTER VT
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Description:Located in the village of Chester, this 4-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You’ll enter through the heated attached two-car garage into a layout that’s both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area that works just as well for casual dining as it does for a home office setup. The dining space flows easily into a sunken living room, where the pellet stove becomes a natural gathering spot. Two bedrooms on the main level, each with their own bath, make this a great fit for a variety of living situations. Upstairs, you’ll find a spacious bedroom, a separate flex room currently used as a movie room, and an unfinished bonus area ready for whatever you have in mind. Storage is not an issue here, between the closets and full basement, there’s plenty of space to keep things organized. The home is equipped with a new furnace and four heating zones, offering efficiency and control throughout. Outside, a wide back patio gives you a great place to relax, while the barn and oversized three-bay garage offer serious utility for storage, equipment, or hobbies. The detached garage is currently rented for $500 per month, and the tenant would be open to continuing that arrangement with the next owner. The property borders Lovers Lane Brook, adding to the natural setting and privacy, all just minutes to Chester’s shops, dining, and village amenities. If you’ve been looking for an in-town property with more space and versatility than most, this one is worth a look. Furnishings are negotiable for anyone looking for a truly turn-key property!
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