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.
Set on a quiet country road in Chester, Vermont you'll find this charming 2 bedroom home on a comfortable 2 acre lot. Inside is a nicely appointed kitchen and dining area that flows into the living room and out to the back deck where there's lots of privacy as nature surrounds you. Both ensuite bedrooms are cozy and spacious. The basement could provide additional finished space as well as more storage. Built with high efficiency insulated concrete forms. A pellet stove keeps the house toasty and there are a couple plug in baseboards for back up. This is a great opportunity to get into a home and make your finishing touches.
Don’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 it’s a place to create lasting memories. All only 15 miles from Okemo Mountain!
Adorable Village Home in the Heart of Chester, Vermont This charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage. Inside, you’ll love the warm, inviting living space with wood accents, an open-concept kitchen and dining area, and cozy bedrooms filled with natural light. The updated bath has a fresh, modern feel, and the flexible layout offers space for guests, work-from-home, or hobbies. This is more than a house — it’s a home with heart, waiting for its next chapter. Located just minutes from Chester’s historic village green — shops, dining, and year-round recreation are all close by. Whether you’re looking for a starter home, Vermont getaway, or a low-maintenance lifestyle, this adorable home checks all the boxes.
Welcome to your Vermont retreat, an inviting one bedroom, one bath home sat on 2.5 acres at the end of a dead end road in Chester. This 528 square-foot cottage has been thoughtfully updated for four season, comfort, featuring full insulation, a woodstove for cozy evenings, and efficient mini-splits providing both heating and air-conditioning. Recent upgrades include a brand new three bedroom septic system, making expansion a future option and a detached two car garage that offers excellent storage for vehicles, ski gear, or workshop space, along with an electric car charging station hookup. The property is dotted with mature sugar maples, already tapped, bringing an authentic Vermont sugaring tradition right to your doorstep. Just minutes from Chester‘s, charming Village center, and Springfield amenities, and a short drive to Okemo Mountain resort, this location is ideal for year-round, living, a ski getaway, or a weekend retreat. Whether you’re seeking a low maintenance primary residence or a charming, second home, this property blends, rustic appeal with modern convenience in quintessential Vermont setting.
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.
The view from the road does not give you the fact that behind the house is a beautiful and private backyard! This property has great possibilities for you to create your own vision of what it can become. You could either do some improvements to the existing gambrel structure which has been a comfortable residence for many years, or you could use it as some kind of allowed business or rental and turn the really nice barn into your new house. The barn sits in a really nice spot overlooking the open landscaped property, with a nice private woodsy area behind. Offered for sale for the first time in almost 40 years!
They say location is key for a property, if that is true this home knocks it out of the park. Located on a quiet country road less than 3 miles to Chester and 6 miles to Springfield sits this well-maintained ranch home on 2.6 mostly open acres. The open and slightly sloping yard has of established landscaping offering lots of opportunity for gardening, recreation and just good old-fashioned relaxing. Roomy screened porch allows you to enjoy outside all summer without worrying about bugs or rain. Oversized 2 car garage, while not attached does have a covered walkway to the house providing coverage from the elements. The roomy eat-in kitchen has stainless appliances and updated countertops. The light filled living room has views of neighboring pasture as well as open yard. 3 bedrooms and full bath round out the main living area. Hardwood floors give a warm and cozy vibe. Walk out basement has a nicely finished family room with wood stove overlooking the back yard. Laundry room, 1/2 bath and a bonus room finish off this very clean and dry basement. Outbuildings include a pool house for storing all the pool supplies for the above ground pool and you might be able to find a place for a hen or two. Well-maintained, manageable in size make this the perfect home for most anyone. Please call for a showing today!
This Cozy cabin tucked away along the outskirts of Chester is sure to impress. With a brand new roof, heating system and more this is the perfect turn key retreat. The property features both open lawn and forest to explore, just up the road from snowmobiling and hiking trails this property has the ability to be your home base for all your favorite activities year around. Including close proximity to Okemo for downhill skiing and snowboarding in the winter as well as the Chester village and downtown Springfield being only about a 10 minute drive to the local shops, restaurants and more. In a quiet and serene setting this cozy cabin is well maintained, private and has so much to offer!
Beautifully set in total privacy, this cozy cabin is the perfect retreat! Nestled on a secluded, level lot, this charming home offers a peaceful escape surrounded by nature. Inside, you’ll find wide pine floors, granite countertops, and a freshly painted interior and exterior that give the space an updated feel. The spacious layout includes large rooms and a versatile loft ideal for guests, a small home office, or extra storage. Unwind in the large Jacuzzi jet tub after a long day, or step outside to enjoy the beautifully landscaped grounds. A serene, oversized pond adds to the tranquil setting, while a fenced-in garden area is perfect for growing your own vegetables or flowers. Relax or entertain under the covered stone patio, and enjoy the many thoughtful touches throughout the property that make it truly special. Whether you're looking for a weekend getaway or a full-time home, this private cabin has everything you need and more!
This wonderful home has so much to offer! This property has many great features including a brand new roof just put on this summer, great large windows allowing nature light into the living space, a very large oversized Two car garage which also has a magnificent workshop with 220 electric already hooked up, wonderful garden areas with flowers and bushes and so much more! The property also features a newly built timber frame sugar style shack perfect for many different uses. There is the possibility for single level living with the downstairs bedroom being right across from the full bathroom as well as the laundry hook up's being on the first floor. In a great location just a few minutes from the quaint town of Chester 13 minutes from Magic Mountain and just 25 minutes from Okemo Mountain where there are shops, restaurants, Skiing and so much more!
Welcome to your dream home – This meticulously maintained New England-style gem is bursting with charm and modern convenience. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by the beautiful 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!
A big price improvement! The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some love, and this property is looking for that person who can bring it back to its former glory days. As they say, the buildings have good bones, so consider this a blank canvas to do whatever you please for renovations. Since it's very original, you can update without having to tear out former "improvements" that might have taken away the antique charm. Since it was a working farm at one time, it still has the old silo. Years ago, this was made into a 4-level living unit. You can bring this back to life and use it as a very unique vacation rental or keep it as a very cool place for your kids and grandkids - much cooler than a treehouse! The attached barns are huge and for years they were used as an antique store. You could do that again, or you could use it for animals. With the open land which supplies a big supply of hay each year, this property would be great for horses, cows, and other large animals. There is also a sugar house, plus a separate building out front that was also used for the antique business. Several apple trees, a huge rhubarb patch, and more!
Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep. Inside, the home is open and inviting, with plenty of room to relax or entertain. The large finished basement provides valuable living space, ideal for a game room, media area, or accommodating guests. Recent improvements include a brand-new roof and a high-efficiency propane furnace, both installed just last year, offering modern comfort and peace of mind. Ideally located close to Okemo, plus Stratton, and Magic Mountain are just a short hop away; this property offers the perfect balance of privacy and accessibility. With Vast trails, dirt roads to roam on this is a heavenly location. Whether you're seeking a full-time residence or a weekend escape, this home welcomes you to experience the best of Vermont living.
Historically known as the Frank Harris House, this distinguished circa 1880 Queen Anne style Victorian commercial building on .75+/- acres has long been a landmark presence in the village of Chester. With its welcoming veranda and timeless charm, the property has served as a thriving office for many years and has many period architectural details throughout such as, a unique, colored transom window in the first floor meeting room, a white brick decorative fireplace with accent mirror in the large office/reception area, graceful bay windows, a mix of hardwood and softwood floors and a slate roof with diamond patterned bands. The heating system has recently been upgraded with a new direct vent boiler and efficient hydronic wall units to ensure comfort throughout the seasons. Additional features include a spacious kitchen area, 1.5 baths, a handicap access ramp and public water and sewer. The attached rustic two-story barn offers additional storage space and there is a large, second story three-season porch! Whether your vision involves refreshing the property for use as office space, transforming it to a multi-unit investment property or restoring it to a grand, single family home, the Harris House presents a rare opportunity—centrally located in the heart of Chester and within walking distance to the town green, shops, elementary school and recreation area. Also listed as under MLS #5058558.
Looking for your dream Vermont escape? Look no further than this unique and spacious home conveniently located between the towns of Chester and Ludlow. The main floor has a master bedroom, bathroom, dining room, kitchen, and two large living rooms complete with wood burning fireplace. Upstairs are 3 more bedrooms, a bathroom, 2 large bonus rooms, 2 lofts for office, storage, or playroom space, and a book nook with a couch overlooking the main floor living room. Outside you will find a recently added stone patio with wood and propane fireplace, deck, hot tub under cover, a 20kw standby propane generator. Other great updates include a brand new roof, egress windows, newer mini splits for a/c and heat in each bedroom, paved driveway. Lots of furnishings will stay with the house, so just bring your suitcase and skis/snowboards and you are ready for the season! Magic, Okemo, Bromley, and Stratton are not far away! Don't wait, schedule your appointment today to see this beauty!
Discover the perfect balance of privacy, convenience, and sustainable living in this artisan-designed post and beam home. Thoughtfully sited on 10 acres at the end of a country road, this 3 bedroom, 3.5 bath farmhouse offers a rare sanctuary just a short stroll from the charming village center. Designed for today's lifestyle, the home is equipped with solar power and battery backup, ensuring energy efficiency and seamless functionality. The inviting open-concept layout features a modern/rustic kitchen with concrete counters and butcher block island and a free standing brick hearth that warms the living and dining areas. A first floor bedroom/study has a large, private bath with walk-in tiled shower steps away from the studio/exercise room with concrete flooring and a cozy loft. Upstairs, you’ll find playful architectural details such as a whimsical, window-paned hallway partition that leads to the chic primary ensuite bedroom with laundry, 2 additional bedrooms, custom built-ins and an additional full bath. Enjoy the beauty of Vermont from the large screened porch with tiled floor overlooking wildlife and natural surroundings. The garden has a frost free pump, raised beds, pear and peach trees and nearby are two unique vernal, seasonal pools. Modern conveniences include high-speed fiber optics for remote work and a handicap ramp for easy accessibility. This one-of-a-kind residence offers privacy, craftsmanship and connection to nature all within minutes to town.
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 space—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, you’ll find an open-concept kitchen, dining, and living area that flows effortlessly onto a large deck—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 soundproofing—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.
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).
You have got to see this stunning, fully renovated home, rebuilt from the studs up with meticulous attention to detail while maintaining its classic New England charm! Perfectly perched on the picturesque rolling hills of desirable Chester, this 4bdrm, 3bath beauty offers the ideal balance of comfort, elegance, and modern functionality. Set on 6 private acres overlooking open fields and peaceful pastures, this home is designed to take full advantage of its breathtaking surroundings. Step inside and you’re greeted by a spacious, sun-filled kitchen and dining area where large windows frame panoramic views of the countryside. The easy flow and layout blends seamlessly, perfect for entertaining friends, hosting family gatherings, or simply relaxing by the warmth of the Vermont seasons. The 1st floor primary bedroom, 3/4 bath, and laundry room offer an ideal layout for aging in place. Upstairs, you’ll find a primary en suite, 2 addtl bdrms, and a full bath, giving everyone their own space and privacy. A full basement provides excellent storage, hobby, or workshop space. Every aspect of this home has been thoughtfully reimagined, from the quality craftsmanship to the modern finishes, offering a true turn-key living experience in one of Vermont’s most desirable locations. Outside, enjoy six acres of serene land with plenty of room for gardens or outdoor recreation. Easy access to skiing, hiking, biking, and endless outdoor adventures, I-91, Dartmouth Hospital and more.
Charming Renovated Farmhouse in the Heart of Chester This beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’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 Stratton—this is Vermont living at its best!
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.
Welcome to your own private retreat—98 acres of serene Vermont beauty featuring meadows, woods, two ponds, and eight versatile outbuildings. Thoughtfully maintained and tastefully appointed, this charming home is nestled in a park-like setting complete with long, historic rock walls, mature trees, and flourishing perennial gardens. Nature lovers will revel in the abundance of wildlife, from hummingbirds and ducks to deer and the occasional moose wandering past the apple trees and blueberry bushes. Step onto the screened porch overlooking the main pond, perfect for morning coffee or evening relaxation. Inside, warm wood floors and exposed beams enhance the home’s country elegance. The open-concept living and dining area can be warmed by a cozy fireplace and flows into a light-filled kitchen with floor-to-ceiling windows framing views of a mountain you own. The home features two well-sized bedrooms and two full baths, offering comfort and practicality. Additional amenities include a large pantry/laundry room and easy access to a full concrete basement, ideal for storage or workshop space. Beyond the home, wooded trails lead to the back acreage and a hidden, crystal-clear pond perfect for secluded swims. There's ripe subdivision potential, with 14+ acres already surveyed across the Grafton line—an investment opportunity or space to expand your vision. Perfectly situated between the charming villages of Chester and Grafton, this is more than a home, it's a lifestyle.
Beautifully maintained 2005 Contemporary Cape nestled on 6.7 private acres with sweeping long-range Vermont views. Owned and cherished by just one family, this move-in-ready home offers the best of country living with modern updates. The completely renovated kitchen boasts a Wolf range, Sub-Zero refrigerator, Bosch dishwasher, and quartz countertops, seamlessly flowing into the dining area—perfect for entertaining. The cozy living room features a wood-burning fireplace insert and opens via sliding doors to a multi-level deck with panoramic views. Enjoy peaceful mornings on the wraparound covered porch surrounded by nature. With 4 spacious bedrooms, including a serene primary ensuite, there's room for everyone. The finished walkout basement includes a large exercise room, office with wood stove, full bath, and guest bedroom. Recent upgrades include Brazilian rosewood flooring upstairs and a whole-house Kohler generator. The extended one-car garage includes a full workshop space. Paved driveway for easy maintenance. Outside, explore walking trails, tap 14 mature maple trees, or harvest blueberries and strawberries from your own garden. Only minutes from Chester’s charming town green—this is Vermont living at its finest. OPEN HOUSE SATURDAY OCT 11TH 11:00AM TO 2:00PM
With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful; uniquely situated on 20 acres of gorgeous green lawn, fields, forest, rolling hills, extensive stone walls. A mere 2 miles to Chester. Since 2020 the house has been transformed & restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel Solar Array, extensive drainage & excavation work for a drier basement. Radiant floor heat in 3 bathrooms, kitchen & great room. An open, sunny, 750sf apartment w/separate entrance, new kitchen, windows, cork floor, laundry hook-ups, is ready for family, guests, renters. BA w/clawfoot tub has been added between first floor BR & serene spare room which could be easily expanded to create a larger bath, dressing room, nursery, office. Attached 2 car garage has a new metal roof, drywall ceiling, EV charger. The home has delicious well water, beautiful views from every window, and because of the thick stone wall construction, stays cool in the summer, warm in the winter, incredibly quiet and draft-free. A newer, solidly built 8-stall horse barn w/wonderful hay loft, sits surrounded by fields atop a nearby knoll dotted with daffodils in springtime. Also includes: Fiber optic internet, professional landscaping including many new trees & native perennials, new boiler, buried propane tank, new electric service & some new plumbing. COME SEE THIS AMAZING PROPERTY!!! OPEN HOUSE OCT 4TH. 11AM-2PM
Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system, updated electrical wiring, windows designed to match the original style, and solar panels that make the home largely self-sufficient. Features a country kitchen with a spacious living room, and a generous dining room The first floor offers one bedroom and a half bath, while the second floor includes three additional bedrooms and a 3/4 bath. 33 stunning acres, the land includes a serene pond and river ideal for swimming or fishing, five outbuildings, and a magnificent 30x80 19thcentury barn. The property is dotted with apple trees with boundless possibilities— a horse farm, a dairy operation, an Airbnb retreat, or simply a peaceful and charming home in the countryside. Driveway and bridge are going to be moved by the state TBD freight train runs twice a day at lower end of the property wide pine flooring square head nails post and beam barn several outbuildings solid cherry cabinets/butcher block counter 2 pond 3 porches generator Glenwood Stove
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