Chester Vermont Real Estate

Looking to live near the Chester Green? This may be the home for you! Currently used as a four-unit apartment building I believe that the highest and best use would be to return it to a single-family home with one accessory apartment in the back. The house is in need of renovation however, the style and location would lend well to that investment, or renovate the four units as your next venture, either way you will have a fine home near the center of all that Chester has to offer!

Tucked back from the paved road and surrounded by woods, this charming 3-bedroom, 1.5-bath home offers both privacy and convenience. With a little updating and personal touch, it has all the makings of a wonderful starter home or the perfect Vermont getaway. Ideally located near several major ski areas and the lakes region, you’ll enjoy year-round recreation — from winter skiing to summer days on the water. A true four-season retreat waiting for its next chapter! Best suited as cash or conventional purchase.

Looking for an opportunity in an ideal location? This property offers unbeatable potential in the sought-after town of Chester. Located on a quiet country road, but still just a couple miles from downtown shopping and dining you get the best of both worlds. This property offers both open and wooded acreage with fruit trees to enjoy! Featuring two generously sized garages, this home is ideal for buyers looking to create their dream space. Whether you're a car enthusiast, need extra room for tools, toys, and equipment, or just want the flexibility of additional secure space, these garages add both value and versatility to the home. If you're an investor or a homeowner with vision, this is your chance to transform a fixer-upper into something truly special. This property is an ideal location to Okemo Mountain Resort (under 10 miles) as well as Magic Mountain (11 miles), Bromley Mountain (20 miles) and Stratton Mountain Resort (24 miles) where you can enjoy skiing and all of Vermonts seasonal activities alternating year round. Schedule your private showing today!

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.

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.

Open House Thursday, September 11, 4:00 - 6:00 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.

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!

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 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!

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!

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.

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!

Everything you’ve been looking for in a Vermont home—completely renovated with care and character. Nearly every aspect of this Chester property is new: electrical, plumbing, heating, insulation, drywall, windows, and more—offering the low-maintenance peace of mind homeowners crave. The kitchen features a stylish farmhouse sink and stone countertops, while the upstairs bathroom includes a beautifully curated vintage Martini pedestal sink. Original wide plank wood floors have been lovingly refinished, preserving a sense of warmth and history. The standing seam metal roof offers long-term durability, and outside, the expansive level lawn and massive post-and-beam barn are overflowing with potential—whether for gardening, recreation, storage, or transforming into additional living space. A standout opportunity for anyone seeking a move-in-ready home with timeless charm and room to grow. This home is in a prime location near Chester’s Stone Village, Grist Mill, Smitty’s Market, and more. Just 15 min to Okemo and the lakes, 30 min to Bromley, and under an hour to Killington, Stratton, and Mount Snow, it’s ideal for year-round fun. Currently enjoyed as both a family getaway and a successful Airbnb, it offers strong income potential. Whether you’re looking for a primary home or investment, this timeless property is not to be missed.

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.

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 barn is huge and for years it was used as a barn 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! Don't wait on this one!

The Stone Cottage began its long history as a schoolhouse built as the Civil War was nearing its conclusion in 1864. Scottish craftsmen from the Aberdeen region constructed the sturdy structure using a technique referred to as 'snecked ashlar' with hewn ashlar stones laid in horizontal and vertical courses with spaces filled with smaller 'snecks joined with mortar. The random patchwork yields a strong and handsome bond that endures the harsh climates of Scotland and Vermont. Comprehensively renovated 25 years ago the home centers around great room featuring a substantial stone fireplace with vaulted wood paneled ceiling and a wall of windows overlooking the Williams River below. The gracious country kitchen is accented with custom cherry cabinets, built-in dish hutch, granite topped island and expansive bay windows next to the kitchen table and a sliding glass doors opening out to a wide stone paved patio. The light and airy primary bedroom and ensuite bath is located on the second floor, and the private guest quarter bedroom is sited on the lower level with walk-out access to a sitting area above the scenic waterfront. The detached 3 level gambrel barn-garage offers potential for a variety of uses including a workshop and additional residential accommodation. Chester's famous 'Stone Village' is nearby and the Okemo Ski is a 20 minute drive away.

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.

Magnificent Queen Ann Style Victorian with 3 bedrooms, 2.5 baths on .37 acres in Chester Village. The remarkable front porch has a beautiful archway and intricate, colorful ornamentation. A tiled entryway/coatroom leads to the elegant foyer with dramatic stairway and beautiful glass Art Nouveau Newel post light. The living room features a marble fireplace, pocket doors and original stained glass picture window. A formal dining room is ready for entertaining as is the well-appointed timeless kitchen with breakfast bar and a large picture window. The elegant great room is a wonderful living space and features skylights, radiant flooring and a dramatic Venetian window overlooking a lovely view in all seasons. Full length glass sliders lead to a side deck with automatic awning for evening sunset meals. An oversized swim spa/hot tub overlooks the meadow beyond and is a great place to unwind! The second floor has 3 bedrooms, a large bath with a clawfoot soaking tub, walk-in shower and a laundry room with half bath. A finished third floor provides office space, storage or room for overflow guests. The house has been thoughtfully outfitted with a dual heating system. In 2000 a barn/garage was constructed with a second floor for hobbies or additional office space. The lovely fenced in yard has garden space and perennial gardens and a lovely maple tree with a perfectly shaped crown. Walk to the Chester Commons, town recreation area and enjoy all that Chester has to offer!

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.

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.

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

Discover a truly exceptional, custom-built contemporary home nestled on approximately 79 breathtaking acres with panoramic views, offering the ultimate Vermont lifestyle. This versatile 4-bedroom residence features a flexible floor plan that includes a private in-law suite, perfect for extended family, guests, or additional living options. The setting is nothing short of spectacular. Enjoy two spring-fed ponds ideal for swimming and fishing, a charming sugar house, and an enchanting treehouse tucked among the trees. Sports enthusiasts will love the full-size tennis court, while hobbyists and makers will appreciate the oversized detached garage, perfect as a workshop or studio space. Recent updates add comfort and peace of mind, including a whole-house generator, updated appliances, new flooring and carpeting, and a freshly painted entryway. The expansive wrap-around deck invites you to relax and soak in the stunning scenery year-round. Located just minutes from Okemo Mountain and the vibrant village of Chester, this rare property is the perfect blend of seclusion, recreation, and convenience. Whether you are looking for a family compound, private retreat, or year-round residence, this one-of-a-kind estate has it all.