Charming opportunity on 3.18 open acres with a stream along the back of the property adding natural beauty and a peaceful setting. This 3-bedroom ranch offers easy single-level living and a functional layout, ready for updates and your personal touch. Ideal for handy buyers, renovators, or buyers looking to build equity. The spacious land provides room for gardening, animals, recreation, or future expansion while enjoying privacy and a country feel. Property includes a garage, chicken coop, and additional shed for storage, hobbies, or projects. A rare chance to create your dream rural retreat, homestead, or renovation investment with land, outbuildings, and water feature all in one.
Set on .76 acres in the peaceful Chester VT countryside, this former schoolhouse offers timeless farmhouse charm, rich history, and a setting that feels both private and inviting. Framed by classic stone walls, a pond site, and a gently wooded backdrop, the home sits just off a main road, providing easy access to town while maintaining a quiet, pastoral atmosphere. Originally serving the community as a schoolhouse until the early 1960s, the property was thoughtfully converted into a residence that honors its roots while offering comfortable modern living. The original schoolroom now anchors the home as a warm, open living space filled with natural light, where hardwood floors and tall windows create an airy yet cozy environment ideal for everyday living and gathering. The farmhouse-style kitchen flows seamlessly into the living area and features butcher block countertops, a professional-grade gas convection range with double ovens, and a breakfast bar with a charming pass-through window, perfect for casual meals and entertaining. A spiral staircase adds rustic character and leads to the upper level, offering a spacious bedroom or studio and flexible use for guests, creative space, or a private retreat. The primary suite serves as a peaceful sanctuary with vaulted ceilings, custom built-in shelving, a private full bath, and a cozy wood stove. Doors open to a rear deck overlooking the private yard and surrounding countryside. Additional features include a generous first-floor laundry area, enclosed sun porch, outdoor patio, a private hot tub with a heated walkway for truly maintenance-free winter access (no shoveling, ever!) and an attached two-car garage currently used as a game room, easily adapted back to garage space or reimagined as a workshop, studio, or home office. With commercial zoning, just 10 minutes from Okemo Mountain Resort, and a history as a successful Airbnb, this rare property offers character, flexibility, income potential, and true country charm.
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.
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.
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.
Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area â?? a practical entryway for Vermont living. The open kitchen and dining area provide plenty of room for gatherings, while the cozy living room invites relaxation after a long day. A full bathroom completes the main level for easy accessibility. Upstairs, youâ??ll find three comfortable bedrooms filled with natural light. The attached back barn offers exciting potential for additional living space, a workshop, or studio. Outside, enjoy your private fenced backyard with garden space, a fire pit, and even a bar area â?? perfect for entertaining family and friends. This inviting village home combines charm, functionality, and opportunity â?? come experience all that Chester has to offer! Visit the Okemo real estate community today. Taxes are based on current town assessment.
Much more here than meets the eye. This home had heating efficiency completed with SEVCA, new siding, new hot water heater, chimney and furnace inspected and some new exterior paint. Nice level yard, attached two car garage PLUS detached barn! Close to downtown Chester and 15 minutes to Ludlow and Okemo/Vail resort. There is a large 3-season porch, two spacious bedrooms and large country kitchen. This little gem is just waiting for a little polish and it will make a wonderful home. Easy to view, improvements are listed in documents.
Not quite 20 years young, this charming custom-built colonial sits on a private knoll, surveying its 77+/- acre parcel. Blending country comfort and eloquence, you'll find quality craftsmanship throughout, such as blue stone floors and a stone archway. Wide plank floors lead to the country kitchen with soapstone countertops. Enter the spacious dining room with tray-beamed ceilings and oversized windows. A beautifully ballastered central staircase separates the main level. The living room features a masonry brick fireplace and built-in cabinetry. The house has radiant heat on the main level to combat cold winter days. The second floor features a primary suite with a soaking tub and a double sink. Bedrooms two and three share a 3/4 bath. On the top floor, you'll find a large finished space ready for your creativity. Over the two-car garage is office space or a bonus room, which is also accessed by a second staircase. The exterior offers a stone patio ready for summer BBQs or a new firepit for the colder months, and trails that crisscross the 77 acres. There are long-range views that can be opened. Located near the historic Chester Village and a short drive to Okemo, Magic, or Bromley. (acreage is enrolled in the Current Use Program for tax benefits). If you're looking for acreage, plenty of space, and privacy, don't wait to view this unique property. Visit the Okemo real estate community today. Taxes are based on current town assessment.
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
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!!
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.
Almost there! This owner has taken this property to a new level...had the septic discovered and has a report, upgraded the electric entrance and added an EV station, laid flooring, opened up a wall for a much nicer open concept, cleaned and made into a little cottage for skiing, nature loving or just plain home. There are rain barrels for water, let nature fill them up or hire the local water company. Provision has been made for a spring in the back area. There is a seasonal stream bed next to the deck for a touch of nature. It is your turn, lift this affordable A frame to the next level. Seller has estimates for some of the upgrades. Or, use it as it is as a camp in Vermont.
Welcome to your dream home â?? 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 â?? your perfect home awaits!
Charming Renovated Farmhouse in the Heart of Chester This beautifully renovated farmhouse sits on a level half-acre lot just steps from Chesterâ??s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway. Inside, enjoy a spacious kitchen with custom pantry shelving, a convenient first-floor laundry room and cozy mudroom. Two main-floor bedrooms provide flexible living options. The second level has a cozy 3rd bedroom and 3/4 bath plus the luxurious primary suite boasting a brand-new custom bathroom with a soaking tub, oversized steam shower, walk-in closet, and a peaceful sitting area. Outdoor living is equally inviting, with a covered wrap-around porch, screened porch opening to a stone patio, and a tranquil Zen garden. A vegetable garden awaits your green thumb, and the small attached barn offers extra storage or workshop potential. A newly added one-car garage and whole-house generator completes the package. Conveniently situated within 15 minutes of Okemo or Magic Mountain, and under 30 minutes to Bromley and Strattonâ??this is Vermont living at its best!
Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.
Have you been waiting to buy just the right property? An impressive home in a special town in an amazing state might be perfect. This well-loved Victorian has 4 bedrooms in the main house and another 3 bedrooms in the carriage house unit. There is a storage room in between the two spaces with doors to open to easily connect the units. The beautiful main house has a farmhouse-style kitchen, formal dining room for holiday dinners, 2 connecting living spaces with fireplace, a bedroom and a full bath. Upstairs are 3 more bedrooms and a full and half bath. The character and antique doors and trim make this house a home. The carriage house unit has 3 bedrooms, a kitchen and full bath and a large open great room and is perfect for guests. There are also more areas with potential - two more levels of barn space plus the attic. Outside you will find a large covered porch, a level back yard for games, and the Williams River down at the back of the property. Sold turnkey. Be the 4th family to own this home since 1868 and see why Chester has been voted one of the top 10 most beautiful towns in Vermont! Discover the tasty food options, pubs, antique shops, art galleries, yoga & pottery studios, and a country market with great sandwiches, fresh meats and produce. Experience Vermont - hiking trails, world class skiing, farms, refreshing rivers, restaurants, breweries and more. Be close to the best of Vermont's ski resorts! (Okemo, Killington, Stratton, Bromley, and Magic Mountains).
Donâ??t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer, which is a great space to store the skis, poles and helmets from a great day of skiing. The main level features a generous living room anchored by a classic wood-burning fireplace ideal for cozy winter evenings. The sunny eat-in kitchen provides ample space for meals and gatherings, while the full bath with laundry adds everyday practicality. All windows were replaced in 2019, offering energy efficiency and bright natural light throughout. Upstairs, you'll find three spacious bedrooms, including a stunning turret space that creates a bright and airy nook perfect for reading or relaxing under the sun-drenched windows. The original woodwork and architectural details throughout highlight the craftsmanship of a bygone era. Outside, the covered wrap-around porch invites you to unwind and enjoy the peaceful sounds of the nearby babbling brook. Take a short stroll to the local market or explore the picturesque village with its shops, restaurants, and small-town charm. This home is more than just a place to stay itâ??s a place to create lasting memories. All only 15 miles from Okemo Mountain!
Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living spaceâ??perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside, youâ??ll find an open-concept kitchen, dining, and living area that flows effortlessly onto a large deckâ??ideal for hosting gatherings or enjoying the quiet outdoors. Two oversized primary suites with private ensuites provide luxurious comfort for guests or multigenerational living. A standout feature is the expansive bonus room, currently outfitted as a professional recording studio with soundproofingâ??ideal for musicians, podcasters, or anyone in need of a creative or quiet workspace. Step outside to a private, tree-lined backyard with multiple decks perfect for relaxing or entertaining. A two-car garage adds convenience, while the whole-house Tesla battery ensures seamless comfort and peace of mind year-round. Whether you're entertaining a crowd or enjoying a peaceful evening at home, this one-of-a-kind Chester retreat offers space, versatility, and thoughtful features throughout. A wonderful value as a primary home or as a vacation home 2 families could share and still have privacy.
Chester is located in Vermont. Chester, Vermont has a population of 3,010. Chester is less family-centric than the surrounding county with 24.13% 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 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 is 53.2 years.
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.
