29 Houses For Sale in Chester, VT

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$110,000Est. Payment
3 Beds | 1 Bath | 1,214 Sqft
663 Depot Street, Chester, VT 05143
House For Sale

1890's Farmhouse with attached 2-story post & beam barn on 1 acre +/- in the heart of Chester Village. This 3 bedroom, 1 bath home already has a standing seam roof and replacement windows. Now the interior with its high ceilings and generously sized rooms awaits your ideas. Covered front porch and walkout basement with full windows and separate workshop space. Impressive two story barn has 1 garage bay with overhead door. With imagination and creativity, this would make an affordable second home or primary residence. Excellent potential for a home business and en route to Okemo. Short walk to Smitty's Chester Market, a great meat market and small grocery store. Continue down the side walk to the town green to visit the local shopping area, then the town pool/park!

$289,000Est. Payment
3 Beds | 2 Baths | 1,356 Sqft
742 Grafton Street, Chester, VT 05143
House For Sale

Nestled along the banks of the south branch of the Williams River this classic 1908 home awaits you. Just a mile from the center of Chester this welcoming home will be ideal as a full time family home or vacation getaway. With a new septic system installed in 2019, and open and bright 4.98+/- acre lot with large barn, river frontage and easy access to all Vermont has to offer this property has tremendous potential and charm.

$419,000Est. Payment
3 Beds | -- Baths | 3,444 Sqft
26 Common Street, Chester, VT 05143
House For Sale

Very cool property on the Chester Green! 26 The Common has been infused with new energy & exudes a fun vibe helping to revitalize the Chester village. The 1st floor retail space has been incubating as the template of a play-based school and demonstrates how versatile the floor plan can be. With Central air, high ceilings, a pellet stove and a back room that would make a great caf/serving space, there is also a 1/2 bath and a full basement with built in storage. A separate entrance, complete with doorbell and air-lock vestibule, leads to the 2nd floor, a totally roomy living space with a double living room that can alternate as a bedroom with closet space and an outdoor balcony. The spacious kitchen w/breakfast bar is open to the laundry area and a 3/4 bath. A dining room/bedroom and a second kitchen w/full bath & laundry hookups could easily be a mother-in-law apt. The third floor has been brilliantly renovated to add 2 more bedrooms and a luxurious bathroom with soaking tub and interesting tiered crown moldings. Each floor has access to exterior decking and stairways: a top deck perfect for growing plants off the 3rd floor bedroom, a covered porch with 2 entrances to the 2nd floor and a lower deck that could easily accommodate a hot tub. A fenced yard is a plus for pets and a detached 2 car garage provides extra storage. The back property line adjoins the town's Cobleigh field- an amazing resource to have in your backyard!

$599,000Est. Payment
12 Beds | -- Baths | 5,976 Sqft
38 Vt Rte 11 West, Chester, VT 05143
House For Sale

Welcome to the Wylie House, a historic 12 bedroom, 5 bath home on .87 acres with many original details such as Victorian gingerbread, stained glass, an elegant period stairway and a rustic, original 2 story barn. The updated kitchen has attractive tile flooring, crown moldings, center island and a lovely eat-in area with a nook to enjoy morning coffee/tea. The living room has a brick hearth for a wood or pellet stove and built-ins for a great study/home office. The main bedroom features a lovely picture window overlooking the garden & a full bath w/clawfoot tub. An additional front bedroom could also serve as living area. Upstairs there are 2 baths, 5 bedrooms and a finished 3rd floor w/full bath, common area and two additional bedrooms. A 2004 addition adds a spacious gathering room that opens to the large rear deck. A huge, light and bright bonus space w/cathedral ceilings on the 2nd floor is perfect for yoga, a home theater, craft room or professional space. The attached rustic 2-story barn is an amazing space w/an efficiency kitchen, woodstove, full bath, laundry area and large picture window. A custom detailed stairway leads to 3 bedrooms on the 2nd floor. The yard has been lovingly cultivated with perennial gardens and features a garden cottage shed, outdoor sauna, workshop, studio/office wood storage and gazebo. An auto generator keeps things running smoothly and an outdoor wood boiler is a great alternative for heat! Next to town rec area & walkable to town.

$389,000Est. Payment
3 Beds | 2 Baths | 1,918 Sqft
205 Hill Top Road, Andover, VT 05143
House For Sale

This comfortable log home is nestled with privacy on 9+/- acres in the tiny town of Andover with excellent access. This may be your home sweet home! Stone walls, an open field and woods, private drive highlight the location. The large front porch has enhanced many family gatherings through the years and is located just off the comfortable living room. An exceptional brick fireplace, which currently is home to an efficient woodstove, completes the joy of this room. The kitchen is roomy with plenty of counterspace and light, enjoying lovely exposed beams. The first floor also includes a sitting room for quiet space, a dining room, an additional family room/ first floor bedroom, and a full bath. The second level has 3 bedrooms and a full bath, all with spacious side walls due to the gambrel style. Enjoy an engineered septic, a drilled well, attached two car garage, a full poured concrete basement, a well designed easy-rise driveway, and wonderful sun exposure!

$339,000Est. Payment
3 Beds | 2 Baths | 1,700 Sqft
3057 Route 11, Chester, VT 05143
House For Sale

Barrett & Valley Associates Inc proudly offers this fantastic opportunity! Although a business is not being sold, this property includes a large garage that has housed an automotive and auto body business for over 30 years. Included in sale is a nine ton lift and a paint room with downdraft system. The land also previously supported a used car sales lot. Set above the garage is a fine 3 bedroom 1 1/2 bath home that 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. Not a mechanic? How about car collector, woodworker, cabinetmaker or artist? This versatile 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 Susan LeCours with your ideas today!

$979,000Est. Payment
4 Beds | 4 Baths | 2,676 Sqft
816 Popple Dungeon Road, Chester, VT 05143
House For Sale

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.

$329,000Est. Payment
3 Beds | -- Baths | 3,463 Sqft
197 Lower Bartonsville Road, Rockingham, VT 05143
House For Sale

Lovely 1830's 3 bedroom country cape on 3 acres+/- with attached office/artist/professional space. Until recently, it was the site of the local country veterinarian, where a wide range of pets, including a goldfish, traveled with their owners over the covered bridge to be treated. This property includes a 3 bedroom, 1 bath home with open land, large fenced-in area for pets, an attached former clinic space and two barns. The inviting living room features a pellet stove, built-in shelving and hardwood flooring salvaged from an old church. The kitchen features a center island and hand hewn beams that accent the natural woodwork. There is a delightful first floor full bath w/clawfoot tub. A spacious, tiled sunroom provides additional first floor living space and opens onto the deck/patio. Upstairs are 3 large bedrooms connected by a hallway with ample storage. A lovely enclosed 3 season porch adjoins the front of the house to enjoy summer evenings. The attached professional space includes an office/waiting area, 2 exam rooms, a center lab counter, half bath and several additional spaces that could be customized for your needs. The house and clinic space have independent septic systems as well as two separate furnaces. An auto generator and fiber optic internet makes working remotely possible and keeps you connected. The two barns make great additions to the property; one next to the house that is useful as a garage and the other a 3-stall horse barn set on an upper plateau.

$579,000Est. Payment
9 Beds | 9 Baths | -- Sqft
266 Main Street, Chester, VT 05143
House For Sale

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!

$147,900Est. Payment
2 Beds | 2 Baths | 2,688 Sqft
2220 Vt Route 103 South Highway, Chester, VT 05143
House For Sale

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!

$299,000Est. Payment
6 Beds | 2 Baths | 1,600 Sqft
74 High Street, Chester, VT 05143
House For Sale

Only once in a while does such a rare property as this come on the market! This 7 +/- acre farm is just 4 minutes walk to the center of Chester village and features 6 bedrooms, 2 of which are on the ground floor, 2 full bathrooms and ample living space to relax. Additionally this stunning lot with views over the pretty Victorian village is mostly fenced in making it perfect for horses or any other farm animal and will make a great working farm or spacious lot for recreation and gardening. Amazingly the property has several thousand square feet of covered barn space with an impressive 8 bays, plus heated oversized workshop, separate garage and gambrel style hay barn. So much space to store your toys or rent the spaces out for supplemental income.A must see so don't delay!!

$1,499,000Est. Payment
9 Beds | 5 Baths | 4,326 Sqft
339 Richardson Road, Chester, VT 05143
House For Sale

This home with over 207 accessible acres in both Chester and Andover is perfect for a large family or group. 9 bedrooms including master suite on first floor, 5 full baths, large public spaces, and an oversized 3 bay heated garage with full finished game room overhead. Privately set between Chester, Londonderry and Weston with southern and western views. Top quality, recent construction and all amenities: granite counters, double ovens, central AC, radiant and baseboard heating, large stone fireplace, full house automatic generator, shining wood floors, and comfortable dining seating for 15-20. Sled, ski or snowmobile through the front yard, meadows or wooded trails. Small pond in view from front porch. The land is enrolled in VT Current Use and VT Land Trust for tax reduction and land conservation. Most house furnishings are included - list available.

$525,000Est. Payment
3 Beds | 3 Baths | 2,509 Sqft
9 Markham Mountain Road, Andover, VT 05143
House For Sale

Custom built in 2002, this incredibly meticulous home is ready to move right in! This cared for home with 3 bedroom, 2.5 bathroom is on highly sought after Markham Mountain Road, Andover VT. Listen to the stream that borders the back of the just over 2.5 acre parcel while sitting in the screened porch. Beautifully finished with classic details in and out. Radiant heat throughout. Double sided gas fireplace adds ambiance to the living room and the dining area. First floor has cherry wood floors. Large kitchen/dining area suitable for entertaining opens to a three-season screen porch (custom windows replace the screens for colder weather) as well as the expansive patio with built in fire pit, tastefully situated hot tub with a view. Kitchen has Viking gas Range. Large double door kitchen pantry closet with more shelves than you can use! Master bedroom has ample closets. Master bathroom features two separate vanity spaces, a whirlpool tub with a view out to the second floor balcony porch, as well as a separate steam shower. Two additional bedrooms on the opposite end of the house with a full bath and a separate stairway to the kitchen. A bonus loft space is big enough for an extra sleeping area, game room, den or office. The large unfinished walk out basement offers so many options - you decide. Access to VAST snowmobile trail system also trails for hiking, snowshoeing and cross-country skiing. Easy drive to several southern Vermont ski areas including Okemo and more!

$194,900Est. Payment
2 Beds | 2 Baths | 1,224 Sqft
22 Vt Rte 35, Athens, VT 05143
House For Sale

Lovely setting overlooking grazing sheep . This sweet rural ranch is just off the road convenient but private . One level living with large family room , warm paneled living room with fireplace . The kitchen has plenty of cabinet space with pine wood floors , complete with 2 bedrooms and 2 bathrooms . The back mudroom leads to a private level back yard for kids, pets or entertaining . The one car garage has an oversized area with work bench and a bonus three room apartment above, that just needs a little TLC to provide rental income of an in-law apartment . That's not all ! there is small barn with stalls for those goats, chickens or that pony you always wanted. Locate on 2 acres , but abuts the Windmill Ridge Trails of the Pinnacle Association . Come see this wonderful property while it last . listed at 194,900.00

$639,000Est. Payment
12 Beds | 12 Baths | 6,976 Sqft
2206 Green Mountain Turnpike, Chester, VT 05143
House For Sale

Come fall in love with Vermont and this charming late 1700s colonial farmhouse set in a quintessential country location. With 35 acres to call your own, and only minutes away from beautiful Chester Village, you will discover the peace and tranquility this safe and private property has to offer. Cherish its history as a stagecoach inn and tavern back in the 1700s with reminders of those earlier days with original wide-plank pine floors, Rumford fireplaces, and hand-hewn beams. Many possibilities are yours - use the 9 pleasantly furnished guest rooms as a bed & breakfast, airbnb or ski house. Or, enjoy as a large family home with plenty of space for home offices (with high-speed fiber optic wifi throughout), remote schooling, sewing/crafting, or home gym/yoga space. The third-floor owners quarters can be a great spot for teens, older children returning home or visiting friends and family. Bright and spacious inside; breathtaking natural surroundings in every season. So much to enjoy right on the premises with your own spring-fed pond, acres of meadow, woods and paths for hiking, swimming, ice-skating, snowshoeing and cross-country skiing! Fall in love with it all - this one-of-a-kind Vermont home - as you relax comfortably on the back porch swing! This is Vermont peace and serenity at its finest!

$374,000Est. Payment
9 Beds | 9 Baths | 5,788 Sqft
225 Pleasant Street, Chester, VT 05143
House For Sale

Don't miss this comfortable Victorian home, having been a successful Inn for many years, will also be a wonderful location for the life style of your family, be it a business or a residence. With 9 bedrooms and 8 bathrooms plus parking for 8-10 vehicles there is ample space to run an Airbnb or host a large family retreat. With several ski resortsall under 30 minutes away this is an ideal property for a ski/recreational club house. There is plenty of room to entertain with a large dining room, living rooms and the old tavern with a large deck for lounging, after a day of exploringthe area. The propertyhas been lovinglymaintained and it shows. Just moments from the quaint Village of Chester and quick access to I-91, it is convenientlysituated to access all the wonders Vermont has to offer. This is without doubt a specialplace with the value you are seeking! Come, look, see for yourself!

$450,000Est. Payment
5 Beds | 7 Baths | 5,546 Sqft
472 Main Street, Chester, VT 05143
House For Sale

This is one of a kind! Whether you are looking for a home for your family and guests, or something you can use for a home business, this one is for you. It isn't often you find a house in this condition - just look at that porch. Located just a short distance to the village green, shops and eateries. In the other direction you will find the Chester recreation area for pool, tennis, and hiking. You have your choice of ski mountains with Okemo, Magic, Bromley and Stratton all a short drive away... golf, fishing, hiking, biking and so much more that Vermont has to offer. The home is lovely. There is a large kitchen, dining room and living room for formal relaxation. An office and first floor bedroom and full bath, too. Upstairs are 4 more bedrooms and 3 more baths. There is a back staircase off the kitchen. The back end of the house is where fun can happen. There is a bar and sitting area along with two rec rooms, currently with ping-pong, air hockey, billiards and poker tables! In addition, there is a large multipurpose room... exercise, shop, studio, rental space.... you decide! The fiber optic internet means you can stay in touch with work or take in your favorite movies. The landscaping is very attractive. Off the back of the house, there is a private deck that overlooks the huge, flat back yard. Every inch of it is usable for play or gardens! There is much to love here and in Chester. Offered mostly furnished. Be sure to take in the video to see all there is to offer. TPW Real Estate 802-228-9400 TPWrealestate.com

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