Chester Vermont Real Estate

Single level living with large two bay garage. This house is located an equal distance to Chester and Ludlow via VT RT 103, both offer small town shopping and dining. Ludlow is home to Okemo Mountain Ski Resort and is a short 10 minute drive. Bring your imagination with you when you view this property, the possibilities are endless.
A swan in the making!! Business..Residential Opportunity! This 2 story property features large partially renovated 1st floor retail space with a large 2 bedroom apartment on the 2nd floor. Enjoy 2.22 +/- acres with easy in and out access. A great "owner occupied" business or investment property. Act 250 permitted for retail and/or deli with exposure on Route 103 South in Chester. Approved for 10 parking spaces. A 3/4 bath is on the first floor for the business space. Additional features include, full basement, new furnace, baseboard heat, flexible floor plan with high ceilings, hardwired smoke and CO detectors. This property has so much potential! Put in some work and bring it's activity back! It's ready!
This picturesque lot commands a stunning view from its lofty perch overlooking Stage Road in Chester. The lot is a mix of open field and forest. This would be perfect for your new dream home, gentleman's farm or simply a great getaway location.  This location has so much potential for expansion and will be easily developable. Just insert your imagination.
This has been a loving family home for over 20 years! Great location with easy access to Springfield and Chester. The outdoor patio and garden space are simply gorgeous. The home is surprisingly spacious so don't let the exterior fool you! Large entry way could be redesigned for home office, storage or expand the kitchen.
Great entry level or retirement 2 bedroom, 1 bath Chester home on .90 +/- acres convenient to skiing and recreational activities with pond and apple trees! The first floor layout features a small kitchen and adjoining dining room that opens to the wrap-around deck. The large living room with soapstone woodstove and mini split will keep you comfortable in any season. A stairway leads to the attic for expansion if more living space is needed. The detached two car garage is old but useable with extra storage/workplace and an auto opener for 1 bay. The backyard is level, spacious and lovely and is enhanced by the secret pond with beautiful flowering lily pads and a lovely view! Close to Chester hiking trails, Reservoir and Town Rec area.
Cute as a button and ready to move into this lovely house is perfectly situated on the main street and offers all the conveniences of village life. The yard is large and has lots of pretty flowers to admire. The Williams River out back offers a wonderfully refreshing spot to listen to the relaxing sounds of the water and will simply captivate you.
This charming home is located in a quiet family neighborhood within a short walk to the elementary school and downtown Chester. It offers two bedrooms: one of which is very large. The kitchen has granite countertops and a large glass slider that leads onto the ample sized back deck. The seller has lived here for over 35 years, but the house is vacant and ready for the new owner to make it their own. It needs some attention and updating in certain areas, and with a little sweat and love, this little house can end up just the way you want it. It is being sold "as is", and the seller will only be accepting offers that are conventional or cash. The remaining contents of the house as well as the hot tub and ramp in the front will be removed, and stairs will be built off of the front porch.
You will recognize the quality of this 1942 built home of this home. Solid, with hard wood floors, a fireplace, 3 bedrooms, 1 bath, a standing seam roof, and great expansion space, ready for your imagination on the second floor. There is no question regarding the care this home has received during its lifetime. The grounds are manicured and nicely landscaped! Enjoy a 2 car garage and a paved driveway. Walk to the many conveniences offered within the village of Chester.
This spacious double wide features a large master en suite, cozy fireplace, two full bathrooms and an open concept living area. Situated on a bright and open 3 acre lot this home has quick access to Chester Village and the surrounding mountains. One level living is the way to go whether you are retiring to a more easily manageable home or you are just starting out with your first home. This property is turnkey and ready to go. Come see this lovely home today.
There's a lot of value to be had with great square footage and potential for a one of a kind property! Featuring 11.43 acres, 4 bedrooms, 4 bathrooms plus multiple other "office" rooms as well as a living room, great room and playroom, there's plenty of space for your large household or perhaps other uses where you just need that extra space. There's a garage door into the basement that could provide inside parking. Tucked nicely off the road, you get privacy and country living while being a couple miles outside the village of Chester. There's a lot of value to be had for those with the ambition and know how to make this home their own!
Absolutely charming Cape right on Main Street in Chester has everything you need. Step onto the new side deck to enter into the large sitting/mudroom equipped with hidden laundry. The open concept kitchen and dining area are perfect for entertaining and enjoys warm wood floors and a lovely bay window. A large living room in the front gets great natural light throughout the day. The upstairs is home to 2 bedrooms with potential for a third or could be converted into a large master bathroom. A large barn/garage offers ample space for storage as well as a place to park your car. Newer corrugated metal roof, boiler, and fresh paint complete this adorable in-town property. This home offers a great rear yard for garden space or play area for children. Just a short walk to The Green, elementary school and dining is another great feature! Could be the perfect full-time home or used seasonally as you are only a short drive to 3 ski areas.
Country home perched on a one acre lot in Chester, Vermont! Ready and waiting! Welcome yourself through the convenient mudroom to the spacious living room warmed by a pellet stove. Continue on to find an eat in kitchen with granite counter tops. Enjoy dinner by the stone fireplace! Peer around the corner and see the cozy master bedroom suite with it's full bath. Traveling up the stairs, you will find two more bedrooms with a bonus room ready for your office or play space! Other notable features include the private country location, equidistant to Ludlow and Chester villages, convenience to I-91, skiing, shopping, golf, not to mention the newly engineered 3 bedroom septic system. A country gem worth visiting!
Absolutely turn key home in Chester neighborhood has it all! This home has been renovated top to bottom by it's current owners and you wont have to do a single thing but move in and enjoy. The corner double lot offers privacey and the home placement is perfect for great southern exposure while still maintaining privacey. The mudroom is welcoming with stylish modern finishes and plenty of space to leave all your gear. The formal dining room is adjacent to the mudroom and is just as inviting. Next find the modern kitchen with pendant and recessed lighting hovering over the center wood block island. New counters, under cabinet light and beautiful cabinetry complete this area. The open concept continues on into the living room with plenty of space for guests to enjoy chatting while you chef up dinners in the kitchen. The brand new 3/4 guest bath is closed off with a sliding barn door and adds to the charm and feel of this modern, sheik property. The master bedroom enjoys a fabulous master bath with soaking tub, walk-in closet even equipped with a laundry shoot that's hidden under a lifetable bench. Wander upstairs and find two cozy bedrooms currently being used as great home offices space. Speaking of working from home, you can enjoy Fiber Optic internet to make the process easy as can be! A few additional bonuses include new wiring throughout, knew insulation, new electric panel and a freshly painted an sealed basement. This property won't last long!
This unique home has been a great seasonal property as well as a full time home during it's lifetime. Cozy and simple in design with a comfortable common area open to the eat-in kitchen flanked on either side by bedrooms and baths. On the lower level walk in to a den or family room with a wood stove. Then, up the stairs to the main living quarters. Enjoy the one car garage which has walk in access to the home. PLUS: A additional small cottage is on the lot. Perfect for an in law suite or rental or caretaker. A tenant currently resides there and would like to stay.
This pretty home sits proudly on Church Street and will, with a little effort, make a fabulous home. Just a few minutes walk to the center of the village and with three major ski resorts all within 15 -30 minutes drive this will be perfect for a second OR primary home. The house has had several updates over the years leaving you the opportunity live in comfort as you put your finishing touches to the remaining spaces. The 2 car garage is an excellent space with plenty of storage up above. The lot has lovely stone walls and a nice private area in the back to enjoy with lots of space for flower or vegetable gardens. A lovely old attached barn also offers opportunity to restore and create additional space for whatever you decide. This home is being offered As Is. Come see this quaint Chester home today!
Fully renovated Raised Ranch will surly impress! This home has been updated and offers ample space with 4 bedrooms, 2 baths and plenty of yard space for gardening and entertaining. Come through the front entry to a split level and head upstairs to find warm hardwood flooring in your living room equipped with an oversized Ashley pellet stove. continue on to the brand new renovated kitchen with state of the art stainless appliances two tone cabinetry and a dining area that overlooks the rear deck. The main level is also home to 2 bedrooms and stylish full bathroom. The Lower level offers 2 more additional bedrooms, a great office or playroom and a new 3/4 bath. The large decks are great for entertaining and enjoying the full day sunshine and with 4 acres of mostly cleared land you can surly find lots to do on your grounds. The barn can house 1 car and doubles as a great storage and includes an enclosed chicken coop. This property offers convenience with smart bulbs, thermostat and doorbell so you can monitor your home 24/7. The perfect home for full time living or enjoy seasonally, you decide!
This home has many surprises hidden from a casual drive by. It has a full rear dormer allowing for three comfortable bedrooms and a both on the second floor. This classic cape has a spacious rear yard and a beautiful enclosed flagstone patio ( an incredible summer room) which attaches to the one car garage. This picture perfect property enjoys hardwood floors, a Harmon pellet stove insert within the fireplace in the living room, 4 bedrooms, 2 baths, an office, kitchen, and dining room. Extensive basement work has been completed allowing for a dry, clean, useable space! So close to all Chester conveniences, even skiing and vast trails, and an easy walk to the center of town. This is simply a lovely home, ready for you to make your own.
A True Vermont country gem is nestled atop of a Mountain on Goodrich Road just outside of the Chester Village. This charming property has been well kept and well loved by its current owners. The grounds are impeccably maintained offering lush perennial's, level lawn space and wooded areas ready for exploring. Enter the home through the convenient mud-room where you can leaves boots and outdoor equipment. Then head inside to the country kitchen offering great natural light and area for dining. The main living room is lined with reclaimed barn boards and a warm Jotul Wood stove. The open concept offers space and skylights let in great sunlight. The best place to relax is in the family room with double glass sliders on both sides of the room. The center floor to ceiling fireplace is the focal point and also offers a nice ambiance on chilly Vermont nights. You will also find two cozy bedrooms as well as bath on the main level. Head upstairs to the open loft which looks down on the living room and is adjacent to the master bedroom with skylights to admire the night sky while you lay in bed and a lovey mountain view. Go explore well manicured lawn and relax on the deck with access to the family room. This property has had many upgrades including handy attached wood shed, oversized shed/workshop, newly insulated to help with heating costs and the list goes on. A true country retreat just off Route 103, a short drive to skiing, shopping and dining. A MUST see!
Located just a short distance for the center of town this 1840 farmhouse has an abundance of character and charm including wide plank pine floors and many great details such as original doors and moldings. You will find an inviting from porch that will lead you into the entry. Country kitchen with Viking range, built in shelving and a wood burning stove for the winter days and nights. Off the kitchen is a cozy den ideal for a home office (fiber optic internet). On the first floor you will also find a beautiful formal dining room that leads to large living room with a classic wood burning fireplace and access to the backyard stone patio. The upstairs has two bedrooms as well as a common space and a second full bath. Off the kitchen you can access the multi-level attached barn that can be used for work space, storage, garage as well as a ground floor ideal for equipment and tractors. The barn is in good shape for its age but could most likely use some shoring up in some areas. It is a beauty. The 16.5 acres are separated by Grafton Rd. The house side is approx 5 acres with a lovely meadow, privacy and about 800 ft of gorgeous frontage on the south branch of the Williams River. The rest of the acreage is across the street with frontage on both Grafton Rd and Quarry Rd. Could be an opportunity for building or selling in the future. This is a must see classic home. Close to all VT has to offer including several major ski areas, town amenities and easy access to Rt 91.
Have you been looking for the perfect log cabin to call your own? Here it is!! Fully furnished and ready for new owners! This log home is super cute and will not disappoint. The current owners have enjoyed the great location with easy access to skiing, shopping, Chester village and Grafton yet it feels like you are in your own private piece of Vermont. Wonderful front porch with brand new swing, firepit with chairs and an incredible shed with power (means this space has many options...bunkroom, expanded family room, storage, etc). This home has been loved and it shows!
This fine 3 bedroom 1 1/2 bath home enjoys southern solar gain, beautiful gardens, stone work and a sweet pond. Reclaim the old hiking trails in the forest behind the house and enjoy the 10 acres of land. This lovely property is set midway between Chester and Springfield with easy access to Okemo Mountain Resort, Springfield Hospital and Dartmouth Hitchcock. A great property that offers a multitude of possibilities! Call with your ideas today!
One of the towns Victorian crown jewels is ready for it's new owners. Two Bedroom apartment with over 2,000 sq ft of living space located right on the chester common. Apartment boasts a large living room with a gas fireplace, deck of the entry. Good sized kitchen with large dining room and an extra 400 sq ft of living space on the finished third floor. The first floor commercial space has been the long time home of successful restaurant ventures over many years. The property is completely set up and ready to go with a fully loaded commercial kitchen that was redone new in 2014. 65 seat facility with enclosed front porch seating with windows looking out over the common. Also features an inviting bar area as you walk in. Basement is set up for storage and has a large walk in refrigerator. Many recent updates including electric, plumbing and foam insulation. This property is ideal for a chef-owner who would like to live and work in a beautiful town setting. Also great extra income potential using the upstairs apartment as a rental. Located in an area of Vermont that is vibrant in all seasons. Near several major ski areas, all town amenities and convenient access to route 91. Come and take a look.
Enjoy the sweet Vermont life in this spacious tri-level 5 bedroom, 2 bathroom renovated farmhouse with detached garage. As you walk through the front door, an over whelming feeling of warmth and comfort envelops you. With newly laid solid hickory flooring along with stunning hand hewn beams which compliment the striking cathedral ceilings above the living room. We invite you to explore this extraordinary open space concept home. This forever home features a brand new heating system along with updated plumbing and electrical. Truly move in ready. The master suite has a private deck to enjoy your morning coffee as you watch the wildlife and listen to the zen sounds of the Williams River from your very own modern farmhouse oasis. The kitchen boasts hand poured concrete counter tops and new state of the art stainless steel appliances. Conveniently located on a quiet dead end street, overlooking the majestic Buttonwood Farms rolling green fields. A stroll around the block leads to the lively charm of Chester Village. With shops, dining and more. A short 15 minute drive takes you to Vails Okemo mountain resort for summer and winter fun, with even more shopping and excursions to choose from. Not to mention the Vas trail access. A property not to be missed. Schedule your showing today!
You will love this classic saltbox home that sits on 5.5 acres a half-mile away from the town pool/recreation center and one mile from Chester village. The large kitchen features high ceilings, ample cabinets and counter space, as well as a breakfast nook overlooking the expansive backyard and gardens. A convenient laundry room/pantry is off to the side. With floor-to-ceiling windows and sliding glass doors onto the back deck, the dining area is the perfect place for warm family meals and dinner parties. The living room is equally spacious with a wood stove and brick hearth that warms the entire foam-insulated home. A den and 1/2 bath complete the first floor. A wrap-around staircase leads to two bedrooms, full bathroom, master suite, and an office perfect for working from home. Hardwood floors are found throughout the first 2 floors. The basement features a rec room with a walkout to the backyard. A must-see
This exquisite home has been tastefully renovated throughout. The front porch invites a bit of respite and observation with a pause now and then as folks walk by with a hello. A visit offers quite a surprise in terms of the spacious floor plan and great flow! Family and friends easily gather throughout the common space, yet plenty of quiet time area is available. The modern kitchen is open, with ample stone counter tops, and newer appliances. The pantry has been saved and serves as incredible storage! A large office or den is adjacent to an expansive great room combination. A full bath is located just off the kitchen. The second floor landing is comfortable introducing four bedrooms and a full bath and a laundry. The great carriage barn retains it's one holer and has had substantial work done to add to it's long life. It is an incredible building to explore! The side yard is level and enjoys a patio offering expanded fair weather family enjoyment.
Overlooking the south branch of the Williams River, this expansive, 3+ bedroom, 3.5 bath 2006 contemporary home on 5 acres +/- is located on a country road just outside the village of Chester. With a subtle nod to Victorian style and high ceilings throughout, there are many attractive features to enjoy such as an open kitchen/living area with breakfast bar, wood stove and half-bath located near the mudroom entry. Lovely interior French doors open to the living room with a formal gas fireplace and bay window alcove, an inviting foyer, a first floor study/office, and a wonderful sunroom with floor to ceiling windows flanked by two deck/patios. The second floor features a large, private en suite bedroom with a large walk-in closet and full bath. The relaxing sounds of the river can be heard from the two additional bedrooms connected by a full bath and laundry. The walkout basement has a large, semi-finished space that would make a terrific game room or in-law apt with a 3/4 bath, a work sink, laundry hook-ups in place and a storage room accessed on either side of the basement. The attached two car garage adjoins the mudroom entry includes workshop space, and a large, second floor unfinished bonus space that could serve as a home office. The landscaped grounds feature two decks, a covered porch, perennial gardens and a riverside firepit accented by a dramatic vertical stone. A path through the woods leads to a super cool treehouse with a swing for two!
This 1780's stunning yet quaint home in the heart of Chester and Southern Vermont is truly the ideal location for a spectacular private residence or successful hospitality business. Owned and operated with love this building has provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. The period home with newly renovated 2 bedroom separate living quarters comes mostly furnished leaving you space to add your personal touches.  The main floor is easily accessible with first floor accommodations for those needing to avoid stairs.  Gracious rooms and cozy common areas invite you to relax in a central location allowing easy access exploring the surrounding Chester village and with mountains, lakes and streams all within short drive you will not lack options for fun and relaxation. Come see this charmer; you may want to stay awhile!
An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.
Welcome to Deer Valley Farm also known as the Williams Homestead. This is the first time the property has been offered for sale in over 60 years! The home has been lovingly cared for with lots of improvements over the decades of ownership. Outside: The barn has undergone major work which insures its stability for years to come and includes a wine cellar. It measures 45x105 with plenty of room for cars, toys or animals. Other improvements include stonework, tennis court and pool with pool house and gardens. The walking bridge over the Williams River includes 4 staircases to the river and built in lights. The home is styled with Italian tile throughout and offers cozy antique charm with 3 fireplaces. The home does need updating but will be well worth the effort. The structure itself has been well maintained. The large acreage easily lends itself to a few other incredible homesites. Located just outside the town of Chester less than 4 hours to NYC and 2.5 hours to Boston. Minutes to all of Southern Vermont amenities including Okemo, Stratton, Killington, Vermont Country Store, Weston Playhouse, world-class golf and the shops in Manchester. This property will not disappoint.
This custom one-of-a-kind timber frame home sits on 10+ acres, located just outside the charming village of Chester. The stunning craftsmanship, and superior quality of this home is evident from the moment you step inside. Surrounded by beautiful scenery, the open layout boasts vaulted ceilings in the great room and radiant heat maple flooring throughout. An abundance of natural light streams into the living space where a modern kitchen includes a built-in grill and stainless-steel, Energy-Star appliances. There is an en-suite primary bedroom, guest room, and guest bath on the first floor along with an office/study built for two. A separate entrance from the attached, heated two-car garage opens into a mudroom/laundry room with exquisite slate flooring. The second floor incorporates an open loft area overlooking the great room and surrounded by three bedrooms and a full bath. Central AC, and whole house ventilation allows you to enjoy this home in all four seasons. The pastoral grounds accented by stone walls, an orchard, and a hillside backyard highly favorable for solar panel placement, largely out of view. This idyllic property is close to Okemo Mountain Resort and many golf courses, and the villages of Chester and Ludlow. You must see this stunning home and the beautiful private grounds to be able to . describe the fulfillment of living in this classic Vermont home. Owners are relocating.
This extraordinary residence and property is located in the vibrant community of Chester. Chester is easily accessed from Interstate 91 and is the gateway to many of Vermonts best ski areas which create an abundance of exceptional restaurants, cultural events and recreational options. The property is a south facing, very private 79 acres which consists of well maintained woodlands including a sugarbush with state of the art sugarhouse and open meadows in the forefront of long range views. Located just below the residence is a large swimming, fishing pond with an adjacent lighted tennis court. Trails for hiking, cross country skiing and mountain biking are throughout the property. Truly an exceptional setting that has been enhanced by the residence which is expertly sited to take in all that the property offers. The residence was designed and built by the owner who is a renowned wood craftsman. The level of craftsmanship displayed throughout the house is without equal. The choicest woods combined with incredible execution make for a truly unique environment. Every room and space in the house is warm and inviting while offering efficiency and sustainability. Combine this with state of the art systems and unexpected amenities including an adult sized and scaled treehouse make this property a must see for the discerning buyer. You won't be disappointed.

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