60 Chester, VT 05143 Homes For Sale

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$69,000Est. Payment
15 Acres
267 Brookline Road, Athens, VT 05143
Lots Land For Sale

Tired of losing bidding wars on houses in Vermont? Here is a fantastic opportunity to build your dream home on a 15 acre lot. Open, level field by the road with a driveway, Sono Tubes, electric and well already in place as well as an approved permit for a 3 bedroom septic design. Significant frontage on Bull Creek with a bridge over the stream and many wooded trails beyond. Very private location on a dirt road but close to shopping, skiing etc. Don't miss this opportunity to build your dream home.

$93,000Est. Payment
12 Acres
360 Dorman Road, Andover, VT 05143
Lots Land For Sale

This wooded 12-acre lot is on one of Andover's prettiest roads and within just a few minute's drive to the villages of Weston for summer theater, Ludlow for restaurants, shopping and skiing at Okemo, or Chester for fun and dining. The land rises gently to the northeast and there are numerous building sites and even the possibility of a sizable pond. The VAST trail crosses Dorman Road about 0.2 mile away and provides access to snowmobiling and hiking trails. An outdated town-issued wastewater permit indicates suitability for building a three-bedroom house, but State wastewater permitting will need to be completed prior to building.

$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!

$124,900Est. Payment
16.4 Acres
0 Brookside Drive, Chester, VT 05143
Lots Land For Sale

This private, 16+/- acre property has a western exposure with a southern tilt that basks in sunshine all day. There are three potential building sites with roughed-in driveways. At the top of the property is a private, small, spring fed pond. An inground cistern and underground concrete piping allow for water drainage. Pathways were roughed in but now need some clearing. This property would be perfect for carbon neutral development with on site wind, solar and hydro power all possible and practical. Enjoy Western views of Magic Mountain and romantic sunsets from your hilltop villa. With some vision and small growth clearing, the building sites can be reclaimed. Current septic permit in place for a 3 bedroom home.

$33,000Est. Payment
1 Acre
0 Howard Hill Road, Andover, VT 05143
Lots Land For Sale

This sweet lot sits directly across from the back fairways of Tater Hill golf course. With some light clearing you will have pretty views of the greens, the pond, the stunning hills as a backdrop and all the peace and quiet you can hope for. A truly tranquil site in the heart of the southern Vermont hills. This bright eastward facing site has power at the road, a gentle grade and could be easily developed into a wonderful location for either a full time home or seasonal summer camp retreat. For winter fun the location is ideal with 4 major ski resorts and a number of VAST trails access points all within 30 mins. The thriving and quaint village of Chester with its shops and restaurants is just 15 minutes away. Come see today!

$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!

$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.

$79,000Est. Payment
3 Acres
363 Dodge Road 5, Chester, VT 05143
Lots Land For Sale

Just minutes walk from the village of Chester this fabulous lot features sweeping views of the surrounding countryside. With 3 bedroom septic, pond and pretty stone waterfall and patio area hidden away from the world this will be a perfect location to build your forever home or weekend hideaway.

$525,000Est. Payment
523 Acres
84 Walker Road, Athens, VT 05143
Lots Land For Sale

Come explore this expansive 523.84 +/- acre Forest that offers excellent potential for a seasonal cabin or year-round home in the southern Vermont town of Athens! Comprised of three parcels, the property offers a private nature wonderland with an excellent interconnected trail system, miles of streams, & an abundance of wildlife - all for your personal enjoyment. The private recreational opportunities are seemingly endless with the forester for the property noting that hunting, skiing, snowshoeing, hiking, nature watching, snowmobiling, and even fishing possibilities on the land exist! Setback from an existing, owner-maintained 50 right-of-way off of a quiet Class III town road, the property opens up to a large landing that would make an ideal spot for a future cabin or home site if appropriate septic is identified per state regulations. A utility pole is located at the right-of-way access off Walker Road, & utilities would need to be extended to the property. There is no town zoning! Logging trails & old woods roads provide easy access to the bulk of the acreage & the VAST snowmobile club currently makes use of some of these trails with permission from the owner. Greater views may be enjoyed from the land with some clearing. The entire property is enrolled in Current Use, offering reduced taxes with good stewardship of the land. Just minutes away from Athens Pond! Route 35 is conveniently within a mile from the property & provides easy access to I-91, MA, NY & beyond!

$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.

$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!

$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!

$89,000Est. Payment
8.53 Acres
205 Arrau Road, Andover, VT 05143
Lots Land For Sale

Located just northeast Weston village and only a few miles drive to four of southern Vermont's best-loved ski resorts, this lovely wooded retreat has 8.5+/- acres waiting for you to build your dream house. A state wastewater permit has been completed for a four-bedroom house (WW-2-1925). The lot is wooded, mostly level with graceful contours and several ideal building sites. The road is quiet, shaded and town-maintained. And, when the world gets back to normal, you'll be minutes away from world-class theater in Weston, live music throughout the region, summer fun on local lakes and ponds, and shopping, restaurants and amenities in Ludlow, Chester, Weston and Londonderry.

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