Chester Vermont Real Estate

The owners have done some significant work on the lower level, removing floor tiles, wall paper and have freshly painted! At it's new reduced price it's a great value. This four-bedroom, one-bath home is located in Chester, Vermont on a peaceful and quiet road. As you enter the house, you walk into the large living room that has a wood burning stove and skylights that provide great natural light. Directly through the large living room is the dining room and kitchen. The main level also features a full bathroom, laundry room and has access to the secluded back deck. Two of the bedrooms are located on the main floor near the living room, and both bedrooms are spacious with wooded views. As you go down the stairs, there are two more bedrooms and an exterior door. For those that enjoy fresh air, the front of the house features a screened in porch and the rear large deck is ready for stargazing. The house is a blank canvas ready to update to your vacation dream home. Taxes are based on current town assessment.
Welcome to 346 First Avenue! This family home is ready for new owners to make their own lifetime of memories! Come sit on the welcoming front porch and watch the Green Mountain Flyer or just listen to birds chirping from the perennial gardens. Stroll to the local store and downtown Chester. Only a few minutes drive to several ski areas, shopping and easy access to I91. Once inside you can tell this home was LOVED! Lots of light, pretty woodwork and main level bedroom are on your wish list and this home offers all those things. Kitchen is functional with tons of cabinet space and counter top space. Need more room? The attached barn is ready for your ideas! Expand the kitchen and take advantage of the large pantry! The bedrooms are spacious and upstairs bathroom is sunny and bright! This home is deserving of the work that someone will put into it and will be well worth it and most of what needs to be done is cosmetic. Two car garage with lean-to off the back are perfect to hold "all the toys, tools and equipment". Unfinished space in the upper part of the garage could be awesome game room, man cave or yoga studio! This is a truly wonderful property just waiting for you...come take a look.
Beautifully maintained 3 BR Ranch only minutes to town. Home boasts 3 good sized bedrooms including a primary with Bath/Laundry room and direct access to the side deck. Entryway Mudroom with built in cabinetry that serves as a pantry. Nice kitchen and dining area that opens up to a large living room. The sunroom is a bright space overlooking the yard with access to the side deck. Can also be used as an excellent office space. Hardwood floors throughout with the exception of the kitchen. Full unfinished basement with garage and stair access to the main floor. The driveway is paved and you also have a paved landing for parking by the side entrance which is used as the main entry. The 1/2 acre lot is level with a great backyard. Close to several major ski areas and all of what Vermont has to offer. This is a gem so come and take a look.
Lovely ski chalet in Chester - just in time for winter! Have you ever wanted to kick back and relax at your Vermont getaway? Here's your chance. Seclusion and serenity are your friends here, and this home on 10+ acres is perfect for a ski vacation getaway. It has been lovingly maintained and is ready for new owners. Enjoy the partially open backyard and fire pit. Then, head inside to warm up next to the cozy fireplace. Vaulted ceilings and the open-concept kitchen/living space make it perfect for entertaining. The two main level bedrooms share a full bathroom. The primary bedroom is upstairs, just off the loft area which is perfect for your at-home office, and features its own 3/4 attached bathroom. New furnace and huge propane tank - great for epic winters. Williams Road is on the VAST trail. The driveway is steep but nothing crazy, with plenty of room to turn around at the top. Close to ski trails but far enough away to forget about the traffic for a while. Fiber optic internet is on site. A bit on how to get here: "You can't get there from here". Williams Road is a dirt road that follows the Williams River. Be careful not to follow phone GPS, but follow written directions. Enter from Popple Dungeon Road onto Nudist Camp Road. Don't wait. This one won't last long! Video tour available upon request.
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.
This well-loved home sits handsomely overlooking the middle branch of the Williams River and provides exceptional access to all that VT has to offer. Just a few moments from the village of Chester and an easy drive to Okemo, Stratton or Magic Mountains. And with I91 just 15 minutes away this is a great access point for commuting and exploring the area. This home has so much potential whether it be a full-time residence, home-based business or vacation getaway. The "workshop/office" with almost 1500 square feet of additional space that can easily be a rec room; garage, host your toy collection, or additional living space. The choice is yours!!Abutting town-owned land on one side and an open meadow on the other this lot feels vast yet easily maintained. There is a wonderful 2-stall horse barn with power and water. Also, there is a neat fenced-in area for the precious pooch in your life. A small-scale home hobby farm would be ideal on this well-laid-out level lot. The central breezeway provides access to the large patio and gardens that overlook the river behind and will provide an exceptional outdoor living space! Come see this wonderfully versatile home today!
Ever dreamed of getting away from it all? Here is your chance to own a secluded, mountain home in the woods! It offers the best of all worlds- privately tucked away on nearly 26 acres but only 12 miles to Okemo Mountain and minutes to the quaint town of Chester! The living room is the star of the show for this house with cathedral ceilings, ample picture windows and a large deck for entertaining or just watching the wildlife. There are two bedrooms on the main floor and a bonus lofted room with it's own balcony. The galley kitchen opens to the living room. Large unfinished walkout basement with sliding doors and a bathroom could be finished to provide another living area and has a pellet stove as an additional heating source. Okemo Mountain is less than 20 mins, Stratton and Killington Mountains less than 50 mins, close to VAST trail and less than 5 miles to Chester town center with dining and shopping. 2.5 hours to Boston
This charming Greek revival located within the stone village of Chester, VT, has remained true to it's original in many ways. The yard is small but inviting. A beautiful view, an apple tree, raspberry bushes, white lilacs and a side patio off the kitchen are all yours! There are many closets as well as a larger enclosed area that could be used as a sewing or art room. The back stairway from the master leads you to to the kitchen where you'll find plenty of room, douglas fir flooring and exposed beams. Much of the house has pine flooring and many replacement windows. There is a detached 16x24 studio that's finished space which has electric and heat. Perfect for someone to have a small business or office on site. There is a large attached two bay garage with custom doors as well as another separate one bay detached garage, both with ample storage for cars, ATVs or snowmobiles. Chester is a vital local arts and music community that's close proximity to many VAST trails as well as 30minutes from several major ski areas. A new propane furnace was installed in November 2022, along with a new water heater.
Simplicity is the key to this newly renovated 3 bedroom, 2 bath country cape on .33 acres +/- in Chester Stone Village. Located just steps away from the walking loop and poised to enjoy the picturesque open valley view, this thoughtfully reconstructed and reimagined 1880 homestead is filled with natural light and wide pine flooring and will capture your heart with its minimal artisan sensibility. The open concept floorplan is accentuated with exposed beams and features a first floor bedroom and full bath with laundry hookups. The expanded second floor features 2 additional bedrooms with ample, walk-in storage and a tiled full bath. Across from the Williams River and convenient to skiing, shopping, Upper Valley, I91 and beyond.
Welcome to 81 Main Street! Built in 1820 and located in the heart of the Chester village, this property is historically known as the Guy Earle House and has been a year round vacation home and short term rental property. This quintessential VT gem on .44 acres+/- features 5 bedrooms and 4 baths. Among it's many attractive features are a large living room with wood burning fireplace, formal dining room, two first floor bedrooms, one en suite and an additional bathroom. The 2nd floor includes a large living area, en suite bedrooms, a bonus game room with a handsome wet bar, hand-crafted from school benches. and a pellet stove. Additional Features include: first floor laundry, mudroom/workshop and unfinished attic space. The double lot has generous parking, an oversized 1 car detached garage with potential space to be finished and a separate shed for gardening in the large level yard. The 4 porches adorning the house offer outdoor covered gathering spaces. Stroll to the green for coffee and browse the shops. Close to 5 ski areas, recreational activities and year round fun! Also listed as Commercial see mls# 4937012
Historic turn of the Century 3+ bedroom, 2.5 bath Victorian on .37 +/- acres known as the Walter Austin house in Chester Village. This grand home has many period features fusing qualities from the Gilded Age to a more contemporary style. 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 classically styled kitchen has a breakfast bar, Corian countertops and accented glass paned cabinets. The splendid great room with cathedral ceilings and skylights has a palladium-crowned triptych window that showcases a pastoral view which will delight 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 tiled shower is located across the hall from a laundry room with half bath. The finished third floor Aerie offers two cozy rooms for office and study or guest overflow. Outside is a lovely deck with awning, a courtyard and- the centerpiece of the backyard- a luxurious relaxing swim spa. In addition to the 1 car garage, a 2 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 rec area make this a wonderful primary or second home.
A true Vermont setting - perched on a knoll with 10 acres bordering both sides of the Williams River, the landscape overlooks a swimming pond, gardens, fruit trees, perennials and beautiful vistas. Share a meal in the open updated kitchen that adjoins the dining area with fireplace and living area with a wood stove. Each of the bedrooms have their own bath. The detached post and beam barn, constructed in 2008, is fully insulated, has three levels including a drive out lower level with water, a Jotel wood stove and electricity. Recent improvements include a new septic system (2017), new heating system (2016), roof (2013), kitchen and baths (2018, 2021). Many specimen trees including several types of apples, plums, hazelnuts and more. A magical spot to take in all four seasons - watch the Green Mountain Flyer go by in the fall, ski at nearby Okemo Mountain in the winter, and swim in the pond in the summer!
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.
Spectacular 7-bedroom country home on 45+/- acres located in Chester, Vermont. This luxurious home combines the beauty of its architectural features with its magnificent country setting. Starting in the kitchen, there is an open kitchen design, large center island, a breakfast bar, a pantry with an additional oven and wine cooler, an oversized kitchen sink, and a commercial grade oven fit for a chef. In the living room there is an amazing stone fireplace with vaulted ceilings, an open post and beam design, and floor to ceiling windows. The dining room is sizeable and could be a perfect place for friends and family to gather for a meal. The main level has two bedrooms located near the back of the home. Both include their own private bathrooms. There is another half bathroom near the mudroom. Upstairs, above the three-car garage, there is a spacious primary suite with a full bath and walk-in closet. On the second floor there are three bedrooms, two of those bedrooms share a beautiful bathroom and the other bedroom has its own private bath. There are two lofted areas on the second floor. One of the lofts is spacious enough for a pool table and an extra living room space. This home includes 4 wood burning fireplaces, 1 outside fireplace and, 2 wood burning stoves. Come see a truly spectacular home that offers unique architectural accents to make you feel like you are in a house fit for royalty. Taxes are based on current town assessment.

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