Chester Vermont Real Estate

This one is ready for you to do your thing! Convert the barn? Build a new home? Park an RV even! This pretty lot sits nicely between Chester and Andover, close to Okemo Mtn and has great access to paved and dirt roads not to mention the nearby Vast trails. The  original house site has been levelled after a structure fire but a wonderful spring well, septic system, driveway, barns, and riverside access all remain. Perfect for a small horse farm, hobby farm or amazing campsite.  Build your dream home, just pick your spot!

Looking for a primary or second home in the beautiful town of Chester? This 3 bedroom home is ready for a new family. Split level entry with nice sized living room, spacious kitchen, and dining area and 3 bedrooms and a bath on the main level. The lower level has plenty of storage, a carpeted bonus room and a drive-in 2 car garage with automatic openers. There is an outdoor furnace that heats the home with wood and oil that has heated the house for many years. If you need an additional bath, the lower level is plumbed for that along with washer, dryer hook ups. There is a large backyard deck, blueberry bushes and a perennial garden area. Beautiful front yard set back off the road and a back yard of trees and trails.

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. This is an excellent opportunity to either convert the home back to a single family or live in one and rent the other. Visit the Okemo real estate community today. Taxes are based on town assessment.

Discover your new home in Chester, VT! This versatile property features 4 beds, 3 baths, a spacious garage, and an RV port, accommodating single or two-family living. The flexible layout includes the potential for an in-law suite, or rental unit, making it adaptable to your needs. Well-maintained, has modern updates, and is a family-friendly and practical space filled with possibilities. Life in Chester is both convenient and charming. Enjoy the village atmosphere within walking distance to the Victorian village boasting historic charm, quaint shops, and local eateries. Schools and churches are within walking distance, adding to the community feel. Explore the Vermont outdoors with scenic trails and fishing spots, creating a serene environment. Winter enthusiasts can delight in the proximity of Okemo and Magic Mountain ski resorts for endless snow-filled adventures. Quick access to both I91 and VT Route 11 makes this a wonderful access point to the entire state of Vermont. This property isn't just a house; it's an opportunity to craft your ideal Vermont lifestyle. Join the welcoming community and make this house your home. Chester, VT offers practical living, a genuine community, and endless possibilities. Your dream home awaits in the heart of Vermont!

Located in the neighborhood of Putnam Hill in Chester, this newly constructed dormered 2.5 story 5 bedroom, 4 bath home on 3.2+/- acres has been framed and is utility ready with septic, well, electric in place. The first floor space features a Great Room with 16' ceilings at its highest points, large kitchen with work area and plenty of cabinet space, a separate dining room for large gatherings, a formal living room and full bath which could also function as a first floor bedroom. The second floor is designed for 4 bedrooms and 2 full baths and the third floor has flex space with four large dormers and beautiful views. This thoughtfully designed home includes a walkout basement with 9' ceilings and intentional framing to include large windows. Solid wood doors are on site along with 10” wide plank pine flooring, furnace and misc. materials. This home was built by a Master tradesman with years of experience. The architectural framing is quite remarkable as is the desirable location of Chester VT with short drives to various ski mountains.

This spacious custom 4 bed,3 bath home sits on 7 acres of land near the end of a dead-end country road and is minutes from the Village of Chester. Built in 2008, this home has ample storage, a large laundry room with a ¾ bath and a roomy primary suite with a custom tile shower, a Japanese soaking tub, and a private deck. The main level of the house has a large living room with brand-new flooring, a wood stove and stone hearth and sits adjacent to the gourmet kitchen featuring a commercial hood over the “Blue Star” 6 burner gas range and pot-filler faucet. The large open plan main level opens to the covered deck and 12 x 22 blue stone patio. On the same level is a large den/office which could be used as a 2nd living room, library or guest bedroom. While the living areas are spacious and comfortable the wrap-around porch is where you will want to spend all your time. This home was built in a controlled environment using 2 x 6 construction with plywood (not composite), copper piping, 10” basement concrete walls & radiant heat in the basement floor. The decking is low-maintenance Trex material and the siding is a high-quality vinyl. The grounds include several perennial gardens and a 6’ deep pond. The basement level is just waiting for your imagination. Skiers, snowboarders, snowmobilers, or just an out door enthusiast be aware, this is an ideal property and location; less than 30 minutes to 3 major ski resorts, close to VAST snowmobile trail, and a short drive to the Chester!!

This beautiful log home is perched upon a hill providing great views and an on top of the world feeling. The long range views can be appreciated outside on the wrap around deck or inside through the large windows in the living space. This property features a wonderfully sculpted eye catching stone fireplace that is sure to set the mood on a snowy evening or late summer night. The property also features a pine board interior with the classic Vermont log cabin look and feel as well as a wood stove to add to the ambiance. The primary bedroom features a large walk in closet with a 3/4 bathroom attached as well as a balcony overlooking the back woods. All this plus a garage in the basement to fit all of your winter or summer toys and, it's also only about 20 minutes to Okemo Resort, 30 minutes to Magic Mountain Resort and 18 minutes to the Weathersfield hiking trail on Ascutney Mountain.

Ready for a life change? A farmhouse in Vermont is waiting for you! Once featured in Country Inns of New England, this property could be yours! The prior owner once operated a successful 24-seat restaurant and an inn. There are five guest rooms - 3 with their own bathrooms and 2 that share a bath, plus 2 double-room suites with their own bathrooms, as well as a four-room owner's suite. One guest suite is undergoing renovations. The stone-floored "Speak Easy" tavern is a great space for conversations and fun. The barn has endless potential for business, guests, yoga, events, or even animals. Set up the white tent on the level lawn next to the barn and decorate the bridge for weddings at the pond (recently dredged and ready for swimming or Winter skating). The small barn is perfect for many uses, smoking meats, or raising chickens. There is even an old milk house for a farm stand! Located conveniently to I91, Okemo Mountain (only a few minutes drive), several other ski resorts, the villages of Chester, Weston and Cavendish. There is much to love about this antique farmhouse property...start your business, your farm, or just enjoy it yourself as a retreat or workplace. Ten acres, a pond, barns, and a large farmhouse. More photos and information will be added as work is being completed. An extensive list of the current owners' improvements and is available and being updated as work is done. New photos will continue to be posted as well. This property is easy to view.

This 3-bedroom house on 30+/- acres near Okemo, with a blend of artistry and environmental features, is a dream home in progress. The use of high-quality materials, sustainable construction, and off-grid origins make it unique. This home is so close to being finished, the new owner will get to personalize it and make it their very own. The house is ready to occupy so you could jump right in and enjoy VT living! The house, now grid-connected, boasts a Kohler generator, solar panels, cedar siding, and a standing seam roof. Inside, eco-friendly quartz countertops, an Italian LaNordica wood cook stove, and locally milled oak floors showcase the commitment to sustainability. The open main level includes a bedroom, office, full bath, and laundry. Upstairs houses two bedrooms, while the lower level walkout features a Morso wood stove and unfinished rooms. Additionally, the property includes an off-grid cottage with a kitchen, wood stove, solar panels, and loft. Priced for completion, it awaits a new owner to bring this masterpiece to life.

Presenting the Walter Austin House, a 3+ bedroom, 2.5 bath Queen Anne style Victorian on .37 +/- acres in the Chester Village. This grand home has many period features and combines qualities from the Gilded Age with a more contemporary lifestyle. The first floor features a tiled mudroom, elegant foyer and spacious living room with an attractive gas marble fireplace. Pocket doors open from the living room to the large formal dining room. The efficient, classically styled kitchen has a breakfast bar, Corian countertops and accented glass-paned cabinets. The spacious great room with cathedral ceilings, skylights and radiant flooring has a palladium-crowned triptych window that showcases a pastoral view which delights year round. The second floor features 3 bedrooms and continues the elegance of the foyer with crown moldings and stained glass windows. A spacious bathroom with a clawfoot soaking tub and large tiled shower is located across the hall from the convenient laundry room with half bath. The finished third floor Aerie offers two cozy rooms for office and study or guest overflow. The grounds are lovely and feature a side deck with an awning off the great room, a private courtyard and a luxurious relaxing swim spa! In addition to the 1 car garage, a two story post & beam barn provides additional garage and workshop space with a second floor rec room or private office. Proximity to skiing, Chester Village Green and town rec area make this a wonderful primary or vacation home

This fantastic and spacious modern farmhouse, sitting on 11 acres, is perfect for anyone who loves to entertain, with plenty of room for friends and family. New flooring and paint throughout. The first floor is open and bright with white shiplap walls and bar, laundry room, and updated half bath with marble vanity and farmhouse sink. The kitchen has granite counters, stainless steel appliances, wine fridge, large island, and walk in pantry for extra storage. The radiant heat, HearthStone wood stove, and Lifebreath air system make this home efficient. The second floor has cathedral ceilings, full bath and three bedrooms; one with a loft. The large primary suite with window seat is perfect for reading. The barn doors open to the primary bath with jetted tub and oversized shower. The primary also has a large walk in closet with custom built-ins. The bonus room is perfect for a home gym. The basement with walk out can be finished for added living space. The additional 30X40 building would make a great workshop or studio. Enjoy the spectacular views from the expansive farmers wrap around porch. The deck offers extra outdoor space. This wonderful private property provides garden space, fenced in yard, chicken coop, and space for animals. With its ideal location to amenities and Okemo Mountain Resort, this modern farmhouse is a must see. Delayed showings until 10/28/23 from 10AM-1PM by appointment.