Chester VT Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,352
Status:
NEW LISTING
MLS#:
5089116
Type:
Single Family
Lot size:
51.2 Acres
Year built:
1986
Courtesy: EXP Realty
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ADDITIONAL INFORMATION

Looking to find your own peaceful piece of the Vermont countryside? Look no further than this move in ready homestead on 51.2 rolling acres with two paddocks already fenced and ready waiting for your animals. Also complete with two spacious sheds for animals or storage, and a chicken coop ready to house them. Established asparagus patch, garden plot, blueberry bushes, apple trees, and even your own cranberry bog meticulously maintained by the current owners await you. Live in the updated home or build the home of your dreams up on the hill overlooking the farm. Make hay for your animals in the fields up on top of the hill, dig gravel from your own private gravel pit, or sit next to the beautiful pond! Plenty of space to hike, homestead, hunt, vacation close to lots of ski resorts or just relax away from the hustle and bustle of the world. Soak up the sun in the attached sunroom or have plenty of room to have all the indoor plants you can dream of. Close to VAST snowmobile trail and within 10-45 minutes of Bromley, Okemo, Stratton, and Magic Mountains! The current owners have done a lots of improvements and cleared the land and are ready to retire to a smaller lot. Don't let this opportunity get away, come take a look today.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,140
Status:
NEW LISTING
MLS#:
5088678
Type:
Single Family
Lot size:
0.25 Acres
Year built:
1945
Courtesy: Barrett and Valley Associates Inc.
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ADDITIONAL INFORMATION

Thereâ??s something quietly reassuring about a home thatâ??s stood the test of timeâ??and this classic dormered Cape in Chester delivers just that, with a clean, updated feel that suits todayâ??s lifestyle. Built circa 1945, the home offers three comfortable bedroomsâ??including a convenient ground-floor bedroomâ??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 functionâ??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. Itâ??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 garageâ??with workshop space and automatic openersâ??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 ownershipâ??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 youâ??re just starting out or simplifying your next chapter. Set in one of Southern Vermontâ??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-locatedâ??if Chesterâ??s been on your radar, this oneâ??s worth a closer look before it slips by.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,308
Status:
NEW LISTING
MLS#:
5088175
Type:
Single Family
Lot size:
7.8 Acres
Year built:
1864
Courtesy: Four Seasons Sotheby's Int'l Realty
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ADDITIONAL INFORMATION

Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal-style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation. Inside, youâ??ll find four spacious bedrooms, wide plank wood floors, and inviting gathering spaces designed for relaxed country living. The heart of the home is the warm and welcoming country kitchen featuring soapstone counters, a center island, and ample room for entertaining. A large living room with a pellet stove creates a cozy retreat after a day on the slopes or trails, while the den offers an ideal space for a home office or quiet study. The screened front porch captures the essence of Vermont living â?? perfect for morning coffee, evening conversations, and taking in the peaceful surroundings. Outdoors, enjoy evenings around the firepit beneath star-filled skies, surrounded by the natural beauty and privacy of the property. A standout feature is the remarkable multi-level 55â?? x 40â?? barn, full of rustic character and endless potential. Having hosted countless gatherings and celebrations, it offers incredible space for entertaining, hobbies, storage, or future creative use. Tucked away just two miles from town, this serene retreat offers both privacy and convenience, with easy access to skiing, snowmobiling, hiking, and all the outdoor adventure and small-town charm that make Vermont so special.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,332
Status:
Active
MLS#:
5087965
Type:
Single Family
Lot size:
2 Acres
Year built:
1854
Courtesy: Cummings & Co
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ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
5.00
Sq.Ft.:
5,400
Status:
Active
MLS#:
5087874
Type:
Single Family
Lot size:
18 Acres
Year built:
1989
Courtesy: Four Seasons Sotheby's Int'l Realty
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ADDITIONAL INFORMATION

Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg-style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design. Inside, the home is defined by warm, handcrafted detailsâ??wide-plank wood floors, paneled walls, layered moldings, and reclaimed beams create a sense of comfort and authenticity throughout. The scale and layout offer a balance of inviting gathering spaces and quieter rooms, well-suited for both everyday living and hosting. Originally operated as a bed-and-breakfast, the home was thoughtfully designed to welcome guests while maintaining a natural flow and sense of privacy. The surrounding land provides a peaceful and private setting, with stone walls, established gardens, wildflowers, fruit trees, and a blueberry patch woven into the natural landscape. Open areas and wooded sections create a property that feels both curated and comfortably natural, offering space to explore, relax, and enjoy Vermontâ??s changing seasons. A guest house and dedicated woodworking barn add to the propertyâ??s appeal, offering flexibility for hosting, hobbies, or creative pursuits. Ideally located near the charming village of Chester, the property offers convenient access to year-round outdoor recreation, including skiing, hiking, biking, fishing, and scenic trails. Throughout the home, the builderâ??s attention to detail is unmistakable, with thoughtfully crafted custom woodwork and timeless finishes that reflect a genuine commitment to quality and design. Quiet, private, and rooted in tradition, this is a property well suited for those seeking a classic Vermont retreat and lifestyle.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,676
Status:
Active
MLS#:
5087175
Type:
Single Family
Lot size:
2 Acres
Year built:
1951
Courtesy: Real Broker LLC
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ADDITIONAL INFORMATION

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. Youâ??ll enter through the heated attached two-car garage into a layout thatâ??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, youâ??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, thereâ??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 Chesterâ??s shops, dining, and village amenities. If youâ??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!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,304
Status:
Active
MLS#:
5086202
Type:
Single Family
Lot size:
1 Acres
Year built:
1890
Courtesy: Real Broker LLC
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ADDITIONAL INFORMATION

Fully renovated from top to bottom, this Chester property offers the kind of peace of mind thatâ??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 Chesterâ??s Stone Village, the Grist Mill, and Smittyâ??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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,464
Status:
Active
MLS#:
5086105
Type:
Single Family
Lot size:
2.13 Acres
Year built:
2014
Courtesy: Barrett and Valley Associates Inc.
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ADDITIONAL INFORMATION

Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at dayâ??s end. Step outside to a sunny, open lot with a peaceful pond, expansive deck ideal for entertaining, and a handsome shed for storage or hobbies. A recent fresh coat of interior paint and a newer high-efficiency boiler add modern reliability and make this home move-in ready. The large unfinished basement offers excellent potential for additional living space, a home gym, or a workshop. Ideally located near Okemo, Magic, and Stratton Mountains, with easy access to local dining, shops, and year-round recreation. This in a truly special location that is both private and practical.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,026
Status:
Active
MLS#:
5086079
Type:
Single Family
Lot size:
0.32 Acres
Year built:
1953
Courtesy: Buffum Realty
View additional info

ADDITIONAL INFORMATION

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.

Open House:

Saturday, 5/23 12:00-2:00PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
1,320
Status:
Active
MLS#:
5085214
Type:
Single Family
Lot size:
10.86 Acres
Year built:
1989
Courtesy: Edge Realty Vermont
View additional info

ADDITIONAL INFORMATION

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 wonâ??t want to miss on your home buying adventure! Truly a stunning property with so much to offer!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,966
Status:
Active
MLS#:
5084462
Type:
Single Family
Subdivision:
No
Lot size:
3.08 Acres
Year built:
1993
Courtesy: Four Seasons Sotheby's Int'l Realty
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ADDITIONAL INFORMATION

Tucked away at the end of a quiet cul-de-sac just one minute from the heart of town, this 4-bedroom retreat offers a rare blend of privacy, possibility, and connection to nature. Set on 3 mostly open acres with glimpses of the mountains and the soothing soundtrack of the nearby river, this is the kind of home that changes pace the moment you arrive. The heartbeat of the home comes from a bright and inviting great room that opens through sliding doors to an expansive deck where mornings begin with coffee and birdsong, and evenings end with the sound of rushing water under the stars. The flowing layout offers spaces that adapt beautifully to modern living â?? a dedicated office for remote work, room for a home gym, studio, creative retreat, media lounge, or whatever your lifestyle calls for next. The dining room is ready for gatherings both large and small, while the attached 2-bay garage and generous outdoor space make everyday living feel effortless. Whether you're hosting friends, growing a garden, creating art, working from home, or simply looking for a peaceful place to recharge, this property offers the flexibility to make it your own. Private yet convenient, peaceful yet connected â?? this home delivers a lifestyle thatâ??s increasingly hard to find.

Beds:
2
Baths:
3.00
Sq.Ft.:
2,310
Status:
Active
MLS#:
5083291
Type:
Single Family
Lot size:
37.51 Acres
Year built:
1988
Courtesy: Maple Sweet Real Estate
View additional info

ADDITIONAL INFORMATION

Escape it all to this beautifully efficient exposed beam log home on over thirty five acres, twenty six or so added by the current owners. Better even, you'll abut the conserved 777 acre Windmill Hill Pinnacle Association with fabulous hiking trails including the Pinnacle Cabin you can book for overnight ridgeline trekking stays. Solar panels over the detached garage, leased Tesla Powerwalls for seamless power outage prevention, western moon and sunsets from your wrap around covered deck, two toasty woodstoves and a detached sauna to soothe you so you don't sweat the small stuff. Hyper fast internet with 325 Mbps down, 413 up so you can work remotely, if you must, surf the net to your heart's content or become a luddite and give it all up. Just 45 minutes from Stratton, this wonderful south eastern Vermont town has a whopping population of 380. Shopping in Bellows Falls, Grafton (cheddar!), Westminster, Putney & Walpole. Chester, Londonderry and Brattleboro for the big time. Amazing tree house in the canopy behind the house with a zipline for onsite adventure. Wildlife, recreation and southern, easily reachable Vermont on fantastic Old County Road. Traditional life, privacy, without losing all that's modern. VAST trail access less than two and a half miles north. Lister card states 3BR home; basement twin set of bunk beds are in the 3rd practical sleeping room. Sauna optional: Sellers would be happy to remove it if you prefer not to have it on site.

Beds:
5
Baths:
2.00
Sq.Ft.:
1,982
Status:
Active
MLS#:
5082995
Type:
Single Family
Lot size:
0.27 Acres
Year built:
1945
Courtesy: Berkshire Hathaway HomeServices Stratton Home
View additional info

ADDITIONAL INFORMATION

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 youâ??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!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,168
Status:
Active
MLS#:
5082324
Type:
Single Family
Lot size:
0.5 Acres
Year built:
1986
Courtesy: Buffum Realty
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,600
Status:
Active
MLS#:
5080905
Type:
Single Family
Lot size:
10 Acres
Year built:
2004
Courtesy: Mary W. Davis Realtor & Assoc., Inc.
View additional info

ADDITIONAL INFORMATION

Nestled on 10 picturesque rolling acres, just minutes from Chester Village Green and Okemo Mountain Resort, this beautiful country home offers the perfect blend of charm, comfort, and convenience. The property features established gardens, apple trees, blueberry bushes, and a stone patioâ??ideal for relaxing or entertaining. Inside, youâ??ll find two levels of well-designed living space. The spacious kitchen is a true centerpiece, complete with granite countertops, a large island, stainless steel appliances, and abundant cabinetry. The sunlit dining room opens directly to a back deck, creating an easy indoor-outdoor flow for gatherings. The inviting living room features wood flooring and a cozy pellet stove, while a den with a gas fireplace provides an additional comfortable retreat. The main level also includes a convenient half bath and a versatile bonus room, perfect for a home office, playroom, or guest space. Upstairs, the en suite primary bedroom offers a private haven, complemented by three additional bedrooms and a full bathâ??plenty of room for family and guests. Additional highlights include a full walk-out basement, attached two-car garage, and a breezeway with laundry. A detached garage with upper-level storage adds even more flexibility. Outdoors, youâ??ll also find a chicken coop and an above-ground pool. Located close to the airport, skiing, snowmobiling trails, shopping, and endless outdoor recreation, this property is a true Vermont retreat.

Beds:
3
Baths:
1.00
Sq.Ft.:
2,096
Status:
Active
MLS#:
5080199
Type:
Single Family
Lot size:
1.69 Acres
Year built:
1950
Courtesy: William Raveis Real Estate Vermont Properties
View additional info

ADDITIONAL INFORMATION

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 gearâ??ideal for embracing Vermontâ??s four-season lifestyle. To the right, at the front of the home, youâ??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 youâ??ll find an above-ground poolâ??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.

Beds:
5
Baths:
3.00
Sq.Ft.:
1,812
Status:
Active
MLS#:
5078525
Type:
Single Family
Lot size:
4.97 Acres
Year built:
1950
Courtesy: Town and Country Realty
View additional info

ADDITIONAL INFORMATION

COUNTRY LIVING ON 4.97 ACRES, JUST 6 MILES TO SPRINGFIELD SHOPPING PLAZA. 9 ROOM HOME OFFERS GROUND FLOOR WITH APPLIANCED KITCHEN W/ DINING AREA, LIVING ROOM, SUNROOM, FULL BATH, FRONT BEDROOM, & ANOTHER BEDROOM W/ FULL BATH. THE SECOND FLOOR HAS 2 BEDROOMS PLUS ANOTHER BEDROOM W/ 3/4 BATH AND WALK-IN CLOSET. SEVCA RECENTLY INSULATED ENTIRE HOUSE AND ADDED A NEW FHA OIL FURNACE IN THE SUMMER OF 2025. RETIRED OWNER WANTS TO DOWNSIZE. NEED 24-HOUR NOTICE TO SHOW.

Beds:
2
Baths:
2.00
Sq.Ft.:
2,016
Status:
Active
MLS#:
5075776
Type:
Single Family
Lot size:
2 Acres
Year built:
2010
Courtesy: EXP Realty
View additional info

ADDITIONAL INFORMATION

Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009 and complete with a newer barn, chicken coop, treehouse, and storage shed could be what you have been dreaming of. Conveniently located just a short drive to 91, not far to the Vast trail access for snowmobiling, and near to many Vermont mountains for skiing or snowboarding. The warm and welcoming home features two bedrooms, a multipurpose loft space, a spacious bathroom with a lovely soaking tub, a gorgeous kitchen, spacious living room upstairs! From there you can walk outside onto the covered section of porch or the deck overlooking the spacious lot complete with corrals for animals. Back inside you can walk down the steps to the walk out basement with the utility room, a space currently used as a gym, a cozy living room with lots of space, and a another bathroom. Walk outside and admire the beautiful stone walls and steps, flower beds, and peaceful setting. The barn has so much potential and depending on what you need it could be used for animals, storage, garage or something else you dream up. The extra storage shed affords more storage space. The treehouse overlooks the house from the back yard, just waiting to be used. Set up your appointment to view this home today! Please do not pull in driveway without appointment.

Beds:
3
Baths:
2.00
Sq.Ft.:
3,310
Status:
Active
MLS#:
5074216
Type:
Single Family
Lot size:
5.5 Acres
Year built:
2000
Courtesy: Engel & Volkers Okemo
View additional info

ADDITIONAL INFORMATION

Set on over five acres of rolling Vermont hillside, this three-bedroom, two-bath home is perfectly positioned for year-round enjoyment with a special focus on summer living and seamless access to some of southern Vermontâ??s top mountain destinations, including Okemo Mountain Resort, Stratton Mountain Resort, Bromley Mountain, and Magic Mountain Ski Area. Offered turnkey, itâ??s an ideal basecamp for making the most of every season while staying ready for ski season ahead. Inside, an attached two-car garage leads into a practical mudroomideal for stashing summer gear now and ski equipment later. The light-filled great room and open-concept kitchen form a welcoming space for gathering year-round. Two comfortable bedrooms and a full bath are located on the main level, while upstairs, a private primary suite features a loft overlooking the living area, a spacious bath, walk-in closet, and a dedicated home office. The finished walkout lower level enhances the homeâ??s versatility, offering a game room, TV lounge, additional finished space, and laundry area, with direct access to a hot tub perfect after a summer hike or a winter day on the slopes. A detached one-car garage and additional outbuilding provide extra storage for all your seasonal gear. Warmer months take center stage here, with long days spent hiking and biking nearby trails, exploring local lakes and farmers markets, or relaxing on the expansive wraparound deck overlooking peaceful countryside views. The propertyâ??s partially open land and privacy create a true summer retreat atmosphere perfect for entertaining, unwinding, and reconnecting with nature. As fall arrives, the landscape transforms with classic Vermont foliage, while winter brings easy access to premier skiing and VAST snowmobile trails just a short drive away. Blending laid back summer living with effortless winter readiness, this property captures the essence of Vermont in every season inviting, adaptable, and ready for whatever the year brings.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,205
Status:
Active
MLS#:
5074094
Type:
Single Family
Lot size:
1.71 Acres
Year built:
1989
Courtesy: William Raveis Real Estate Vermont Properties
View additional info

ADDITIONAL INFORMATION

Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of the day sunlight. A bedroom and 3/4 bath round out the main floor. Upstairs you'll find two large bedrooms and a full bath. All good homes should have a family room and this doesn't disappoint. The lower walk out had a cozy spot with a large sectional to watch movies and is perfect for "hanging out" with friends. There is a work out area and a bonus room located on the lower level. This is definitely more than a ski home as there is plenty of outside living space. There is a shady front porch with begs for a rocking chair and a good book. Sun seekers will enjoy the rear deck which faces west and gets plenty of sunshine. Perennial gardens abound and offer color and character all summer long. There is a garage barn that can be used in a myriad of ways... park a car, use the workshop, store your toys... There is also an upstairs mostly finished room that can be your blank canvas. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,788
Status:
Active
MLS#:
5073930
Type:
Single Family
Lot size:
3.3 Acres
Year built:
1900
Courtesy: Barrett and Valley Associates Inc.
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ADDITIONAL INFORMATION

Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here forâ??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 belowâ??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, thereâ??s room to garden, explore, build trails, or simply enjoy your own stretch of water and woods. The surrounding countryside delivers classic Vermont sceneryâ??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 Vermontâ??s natural beauty. A property that offers privacy, water frontage, land, and mountain accessâ??without giving up convenience.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,148
Status:
Active
MLS#:
5073147
Type:
Single Family
Lot size:
1.5 Acres
Year built:
2023
Courtesy: TPW Real Estate
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ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,475
Status:
Active
MLS#:
5069928
Type:
Single Family
Lot size:
9 Acres
Year built:
1985
Courtesy: Brattleboro Area Realty
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ADDITIONAL INFORMATION

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

Beds:
5
Baths:
5.00
Sq.Ft.:
3,880
Status:
Active
MLS#:
5068855
Type:
Single Family
Lot size:
4.8 Acres
Year built:
1803
Courtesy: Barrett and Valley Associates Inc.
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ADDITIONAL INFORMATION

Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chesterâ??s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. Itâ??s a property that allows you to live outwardlyâ??work the land, keep animals, or simply enjoy open, private space. Inside, the home is warm and inviting, with a layout that supports both daily living and gathering. The large living room, anchored by two fireplaces, is a natural place to slow down. A formal dining room is ideal for hosting, and a generous room off the kitchen easily accommodates larger meals and celebrations. Original wood floors, exposed beams, and durable early craftsmanship add character throughout. A separate rental unit, currently occupied, provides steady income or flexible use for guests, family, or workspace. The barn offers storage, workshop potential, or agricultural use, expanding what the property can support. Chesterâ??s shops and everyday conveniences are close by, and skiing, rivers, and trails are within easy reach. Okemo is just minutes away, with Stratton, Magic, and Bromley all within a short drive of 20-30 minutes. Several AT access point within similar distance. The Okemo Valley is on your doorstep, and it's magical! This is a historic home ready for its next chapterâ??solid, adaptable, and full of possibility. Come See Today!!

Beds:
1
Baths:
1.00
Sq.Ft.:
200
Status:
Active
MLS#:
5067929
Type:
Single Family
Lot size:
1 Acres
Year built:
1975
Courtesy: Four Seasons Sotheby's Int'l Realty
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ADDITIONAL INFORMATION

Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny house while working on the original home. Consider the possibility of removing the older structure to make way for something new, or simply use the tiny house as your Vermont getaway. A stone walkway leads gracefully down to the river, providing a tranquil connection to nature. Both structures are believed to be elevated above the flood zone, ensuring peace of mind in all seasons. This lovely property is a nature lover's dream and a rare opportunity to embrace the essence of Vermont's natural beauty.

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Andrea D. Conner, License 71221, Xome Inc., License 68390, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Ste 100, Lewisville, TX 75067


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Chester 05143 Real Estate

Chester is located in Vermont. Chester, Vermont 05143has a population of 3,010. Chester 05143 is less family-centric than the surrounding county with 22.47% of the households containing married families with children. The county average for households married with children is 26.01%.

The median household income in Chester, Vermont 05143 is $61,397. The median household income for the surrounding county is $63,787 compared to the national median of $69,021. The median age of people living in Chester 05143 is 53.2 years.

Chester Weather

The average high temperature in July is 81.5 degrees, with an average low temperature in January of 7.4 degrees. The average rainfall is approximately 45.2 inches per year, with 67.6 inches of snow per year.

Chester Map

Chester Real Estate Market Conditions

  • Median sales price

    $379,000
    19.1%
    change since last quarter
  • # Active listings

    59
    30-day change

Chester Schools and Demographics

Education near Chester, VT

City County
High School Graduates 96.52 94.16
College Degree - 2 year 6.97 8.49
College Degree - 4 year 40.18 40.21
Graduate Degree 11.68 12.49
Expenditures per Student 26,463 26,463
Students per Teacher 12.3 12.3

Elementary Schools near Chester, VT

Grades Students P/T Ratio ZIP
Chester-Andover USD #29 PK - 06 261 13 05143
Elm Hill School PK - 02 415 17.7 05156
Flood Brook USD #301 PK - 08 322 11.1 05148
Grafton Elementary School PK - 06 103 13.7 05146
Ludlow Elementary School PK - 06 115 8 05149
Union School 03 - 05 256 10 05156

Middle Schools near Chester, VT

Grades Students P/T Ratio ZIP
Riverside School 06 - 08 291 11.2 05156

High Schools near Chester, VT

Grades Students P/T Ratio ZIP
Black River USD #39 07 - 12 172 8.6 05149
Green Mountain UHSD #35 07 - 12 336 10.2 05143
Springfield High School 09 - 12 433 11.9 05156

Ungraded Schools near Chester, VT

Grades Students P/T Ratio ZIP
River Valley Technical Center UG - UG 0 05156

Demographics near Chester, VT 05143

Zip Code City
Neighborhood Type Small town
Population 3,010 57,593
Population Density 54 59
Median Age 53.2 47.8
People per Household 2.4 2.3
Median Household Income 61,397 63,787
Average Income per Capita 35,517 39,377

Real estate near Chester