Chester Vermont Real Estate

This quaint Chester home is located on a double lot with a private driveway about 1 mile from the Chester Green with local restaurants, shopping and entertainment . It features a private sitting area under cover, enclosed garage, two good sized bedrooms, walk in shower, and more!
This unique 3 Bedroom 1 Bathroom Chester home is just awaiting the finishing touches! The home is located on 0.50 acres about 1 mile from the Chester Green which has restaurants, shopping, entertainment and is about 15 minutes from Ludlow. This property features in town convenience and the privacy of country living!
Classic Farmhouse with 4 Bedrooms, 2 baths. Currently zoned two family, it can easily return to its single-family origins. Open one door to live as a single family, or rent out the upstairs 2 bedroom apartment and enjoy the spacious first floor. Many classic features: large foyer, wrap around porch, original wood floors, 2 story bay window and large rooms. Improvements include replacement windows, recently replaced hot water heater, furnace, roof and a 'great' room with pellet stove added to the first floor. Full home energy audit/weatherization in 2018. Has a rural feel with yard and gardens, but located close to amenities right off Chester Depot and Route 103.
This pristine Colonial is sure to impress! The home is situated perfectly in one of the best locations in town and only a short walk to The Chester Green. Come inside & find an updated country eat-in kitchen, with a center brick chimney as the focal point. New cabinets, large farmers sink and warm maple floors will welcome you to this fully functional yet great gathering space, where many memories will be made. The formal dining area is perfect for family get togethers and enjoys a large bay window, hardwood floors, and a large pellet stove. The inviting living room is the perfect place to unwind and allows access to the staircase which brings you to the upstairs landing. There you will find the laundry conveniently located around 3 bedrooms. A newly renovated 3/4 bathroom offers ample space and a full glass shower stall. The partially finished barn is the perfect workspace and offers office space along with ample room for extra guests to stay and feel separated from the main living space. The second story of the barn is perfect for dry storage. Relax in your back yard or enjoy no pesky bugs on the large screened-in porch with a lovely view of the well cared for yard. The 2 bay garage and third bay workspace in the barn, as well as triple-pane windows, and Peerless boiler all complete this magnificent village home. Come see for yourself!
Beautiful New Englander in the quaint town of Chester, VT! This well-kept home is boasting with bright sunlight and gorgeous gardens ready for you. Five bedrooms, two full baths, two living rooms, an expansive kitchen with cathedral ceiling, large island and gorgeous exposed beams. Attached garage/shop with two bonus rooms above. The property includes apple and pear trees, herbs, perennials, a small horse barn, a patio and beautiful stonework. Finished in-law suite above garage, recent blown-in insulation in walls and attic, new support posts in basement, to name a few of the recent updates. Charming country setting less than 10 minutes from Chester and Springfield. Close to outdoor recreation, skiing, hiking and more.
Classic 1852 brick colonial home located on the corner of Grafton and Main Streets in beautiful downtown Chester. A short stroll to the town green, library, shops and antique shops. Currently a 2 unit apartment, it's top floor consists of a two bedroom one bath unit while the downstairs is set up as a one bedroom cozy apartment. The house can very easily be converted back to a single family home by simply removing a wall on the lower level which was installed only a few years ago. The whole house has electric and plumbing updates. Two recent hybrid water heaters and furnace. A new roof was just installed. Priced to sell, please note current tenants are occupying both units. Appointments with at least 48 hours notice are needed. Showings will be scheduled in blocks of time. Preferred closing is this spring. This is an excellent opportunity to either convert the home back to a single family or live in one and rent the other. Taxes are based on current town assessment.
Tucked away in the serene town of Chester VT you will find yourself amongst some of the best views the town has to offer. Located on a dead end road you will find this well taken care of home nestled down the long private driveway. Enjoy the backyards breathtaking mountain views from the three season porch. The open kitchen, dining area and living room offers plenty of sunlight throughout the home. First floor living is achievable with both a bedroom and bathroom on the first level. Blueberry bushes are in the backyard ready to be picked and there is plenty of garden space for more to grow with the partially cleared oversized yard. Your tools and equipment are ready to be placed in the large sheds. 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 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!
This beautifully crafted salt- box style home features high ceilings, 3 large bedrooms, 2 bathrooms, spacious living room with Vermont casting stove, all located in a private rural neighborhood making this a great fulltime home or vacation retreat. Close to the welcoming village of Chester and 20 minutes to Okemo Mountain this is ideally situated close to I91 giving you easy access to all Vermont has to offer. Standing seam metal roof, large 2 car garage with direct entry via the newly added breezeway will make for easy living in the winter months. And the private deck off the kitchen is great for cooling off on a hot summer day. Open house is scheduled for Sunday June 12th from Noon to 3PM. Come see this beautiful home.
This immaculately maintained home was built in 2013 and is situated on over 23 acres with a pond and oversized 3-car garage! Enjoy privacy and solitude with plenty of room to garden, hike, cross country ski or snowshoe without ever leaving your own property. If motorized fun is more your style, there is ample indoor storage space for snowmobiles, boats or ATV's. When at full capacity the pond is 12 feet with a sandy "beach" area. Add a floating swim platform for summer fun or enjoy the peaceful spot with a fire in the large stone hearth pond side. The home itself is bright and cheery with open concept living spaces that open to either the front deck or back deck and patio spaces for a great indoor/outdoor flow. Primary suite with large full bath, double sinks, soaking tub, and additional shower. On the other end of the home are a guest bedroom and den with an additional full bath. Also on the main floor is a spacious and functional mud room with a utility sink and full laundry.  If you need more space, the full basement is clean with large windows, high ceilings and could be finished to suit. Heated garage w/3 large bays, workshop space and full second floor for recreation, office space, or could be finished for more living area.  If you do find yourself out and about there is plenty to do nearby. Okemo Resort is only 12 miles away and downtown Chester boasts many boutique shops, restaurants, yoga, and art studios, farmers' market and more! Showings begin Sunday Aug 14.
This home has been completely refinished with fresh paint, both interior and exterior, new flooring, bathrooms, kitchens, a 200 amp electric panel and wiring, a Buderus boiler, insulation, decks, light fixtures and more! If you're looking for a turn-key home on a private road with plenty of land, look no further. Enter into a large open concept kitchen/dining/living room with a cozy fireplace. Upstairs you'll find 3 spacious bedrooms including a primary bedroom with shiny wood floors and a gorgeous ensuite bathroom with double sink. Upstairs you'll also find an office, laundry room and another full bath and an additional 3/4 bath. Plus a loft!! A very sturdy ladder brings you to a great reading nook or possibly a child's dream bedroom, with plush new wall-to-wall carpeting. Back downstairs, off the living room is a beautiful refinished in-law suite! This features a galley kitchen with butcher block counters, rustic white wooden backsplash and an eat-in bar. There are two bedrooms or offices in the suite as well as a full bathroom and expansive living room. In addition to all this, there are two walk out basements with big enough doors to drive your lawn mower or possibly something larger into. All this on almost 12 acres of sloping lawn and garden space surrounded by the privacy of the woods. Come see if this is the dream house for you!
Welcome to Vermont living! This spacious, well-kept home has lots of room for your family, pets, and even an RV in the oversized garage! Situated on over 2.5 acres, there is plenty of privacy. The beautiful yard includes raised beds for veggies or flowers as well as a fenced in area for your animals to stay safe. Located just outside the village of Chester, this home is within 30 minutes to several ski areas. There is a hospital just 15 minutes away as well as grocery and restaurants. Access to VAST trail system right from Marcs Drive. The home is filled with lots of natural wood along with plenty of windows. Downstairs you'll find a large master with an en-suite bath and two closets. The master has a radiant heat floor. The laundry room is also conveniently located on the lower level. Upstairs the three bedrooms and a bath offer plenty of space for the family. Over the garage is an office, and in the basement there's a big bonus room with a walkout into the yard. High speed fiber internet is installed; perfect to work from home. Some of the recent improvements include: paving the driveway; installing a split pump (a/c - heat), staining the house, a new well pump, and installing a bay window. This home has three heating systems and is wired for and includes a portable generator. There isn't much to do here except move in!
Now's your chance to finally own an immaculate log cabin in Vermont. Meticulously built and maintained, the owners are heartbroken to let this house go. Nestled on 5+ acres the home has a full covered front porch for enjoying evenings outdoors. Open concept living room/kitchen with vaulted ceilings are accented by a brick floor to ceiling chimney and a soapstone woodstove. There is a matching separate 2 car garage for cars with loft area for toys. Large deciduous trees shade the property perfect for a hammock. Nudist Camp road is a quiet dead end road with little traffic. Williams River State Forest abuts this property offering wonderful opportunities for snowshoeing, hiking and wildlife viewing. Sellers are installing a brand new efficient hot air furnace and water heater. Taxes are based on current town assessment.
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. Currently rented out as an extended stay rental and generating $8,800 monthly. 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!
Amare! This jewel of Queen Anne architecture adorns a hilltop overlooking the charming village of Chester, VT. The eclectic interior design will delight, surprise, and warm your heart. The 3 bedroom and 3 bath house with attached 2 bedroom/1 bath guest /in-law suite is well appointed to accommodate family and friends. In the main house one will find an open concept kitchen/dining/entertaining area. The kitchen is well designed and equipped with Heartland appliances and opens on one side to an enchanting dining area and on the other side to an entertaining area detailed with a handsome black marble fireplace. A classic covered porch is easy to access for outdoor dining and taking in the Vermont hillside and village life. Additional living space is found in two spacious living rooms and a cozy media room. The attached guest/in-law suite is complete with a fabulous kitchen/dining/living area and an upper-level bedroom with ensuite bath. The exterior is composed of three covered porches, a stone patio, and pergola all detailed with native perennials. A gorgeous 50 x 30 three story barn completes the quintessential Vermont landscape. Updated plumbing, electrical and heating include a Bosch boiler and Buderus panel radiators, and 200 amp electrical! Perfect as a primary or secondary vacation home with easy access to village life and multi-seasonal recreation at nearby Okemo, Stratton, Killington and Bromley resorts.
Gracefully settled between the villages of Chester and Londonderry, sits a Vermont Farmhouse at road's end, sited on eleven+ acres of wood'n meadow. Dotted with old stone walls, a wildlife pond and enchanting views. The setting is magical. A wide country porch invites rocking chairs and visitors while the screened area encourages outdoor entertaining much of the year. The vintage flavor is apparent throughout the home- opening panel doors with antique latches or stepping foot on wide wood floors milled from indigenous trees from decades ago. This location is central to recreating: ski, hike, snowmobile, swim, or enjoy our local restaurants, theater and shopping. A center island kitchen with breakfast nook overlooks the rolling meadows and glass doors allows life to spill over onto the porch, deck or firepit area. A traditional dining room, adjacent to the intimate living room, awaits memorable dinner parties. The great room’s remarkable soaring ceiling creates a central gathering spot and includes a cast iron wood burning stove to warm by when winter is settling in and snow abounds . The main floor bedroom would also make a delightful home office overlooking the fields to the rear. Upstairs you'll find additional bedrooms including a large “beamed ceiling” primary and a fun multi-functional den/game room. Two sets of farmhouse stairs give easy access. If quiet and open and vintage is your desire..Look no further. Showings begin Thursday, May 12th. Owner is a licensed Realtor.
Unique opportunity to own a piece of history. This six-bedroom, five and a half-bath home on .67 acres is nestled in the heart of the historic stone village. Chester's stone village is currently recognized by the United States Department of Interior as perhaps one of the only stone villages in the country. This two-story federal-style stone home offers many opportunities with its spacious floor plan. Enjoy flexibility with an accessory apartment above and fully renovated owner's quarters below. Walk the grounds to enjoy the patio with its own stone cottage that is currently used to make maple kettle corn. Cross the garden bridge on your way to the lily pond or enjoy the shade from one of the fruit trees. The property offers the best of both worlds with a sprawling backyard yet conveniently located to restaurants and shopping. Okemo Resort and the lakes region are just a quick 12 miles away. This location offers lots to do each season including festivals, the Weston Playhouse, concerts, and much much more. Taxes are based on current town assessment.
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 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 a 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 private 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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