84 Homes For Sale in Chester, VT

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1100 SqFt House In Chester
$175,000Est. Payment
2 Beds | 2 Baths | 1,100 Sqft
71 Canal Street, Chester, VT 05143
House For Sale

This charming home is located in a quiet family neighborhood within a short walk to the elementary school and downtown Chester. It offers two bedrooms: one of which is very large. The kitchen has granite countertops and a large glass slider that leads onto the ample sized back deck. The seller has lived here for over 35 years, but the house is vacant and ready for the new owner to make it their own. It needs some attention and updating in certain areas, and with a little sweat and love, this little house can end up just the way you want it. It is being sold "as is", and the seller will only be accepting offers that are conventional or cash. The remaining contents of the house as well as the hot tub and ramp in the front will be removed, and stairs will be built off of the front porch.

New
Lot In Chester
$90,000Est. Payment
7 Acres
147 Ethan Allen Road, Chester, VT 05143
Lots Land For Sale

Stunning 7.0 acres of land located right on Ethan Allen Rd in Chester VT! Located on a private lot filled with gorgeous nature trails and wild life, this land has a ton of potential for building a forever home. A private three bedroom septic system is already in place, along with a drilled well, and power is available! Call today to check this great spot out!

1576 SqFt House In Athens
$239,000Est. Payment
2 Beds | 2 Baths | 1,576 Sqft
103 Valley Cemetery Road, Athens, VT 05143
House For Sale

Unique semi-earthen built home. Subterranean on three sides keeps you warm in the winter and cool in the summer and also helps keep utilities low. In floor radiant heat. Large 10 acre parcel with woods and open areas filled with gorgeous perennial gardens lovingly maintained since 1998. 2 bedrooms, 2 full baths with a large kitchen, dining, living room open concept floor plan. Huge laundry/utility room. Large double width attached garage, half of which has potential to be reimagined as additional living space. Radiant in floor heating extends to the entire garage space. Two additional garage structures round out the property. Lots of extras such as a sprinkler system for all the perennial beds. House is being sold mostly furnished. Showings begin 6/16/21

2316 SqFt House In Andover
$359,000Est. Payment
3 Beds | 3 Baths | 2,316 Sqft
1923 North Hill Road, Andover, VT 05143
House For Sale

Peace and quiet can be yours in this 1980s chalet on 13+ acres. A super country location, set back from the road in a park-like setting, yet easy access to all area amenities. Three levels of living space with three bedrooms and three baths. Relax on the deck with a book in the summertime or take a dip in the pond. In wintertime you can warm up in front of the main level or lower level fireplace. Lots of knotty pine walls and trim provide a true Vermont rustic ambiance. Beautifully landscaped with carefree perennials and flowering shrubs. If you would like more land the abutting 13 acre lot is also available to purchase for a total of 27.30 acres (see MLS 4866868). Be it skiing at nearby Okemo, snowmobiling from the VAST trail network or hiking on nearby trails this residence can be a year-round home or vacation retreat.

7589 SqFt House In Andover
$3,200,000Est. Payment
7 Beds | 6 Baths | 7,589 Sqft
358 Andover Ridge Road, Andover, VT 05143
House For Sale

Tucked away on Andover Ridge Rd you will find one of the most spectacular properties in Southern VT. This remarkable log home features 7 bedrooms and over 7,000 sq ft of finished living space. The main floor is an open floor plan that features, a large kitchen with granite counters, custom cabinetry, top end appliances and an full length of kitchen island. The kitchen opens up to the dining area and a living room that boasts a custom stone wood burning fireplace, vaulted ceilings and floor to ceiling windows that give you breathtaking westerly views for picturesque sunsets and year round enjoyment of all the changing seasons. The main floor also features a den study and an owners en suite bedroom with gas fireplace. The main floor includes multiple accesses to the large wrap around deck looking down to the pond and property. On the second floor you'll find a game room loft and 3 more bedrooms including another en suite master. Down below the finished basement has a large family/ rec room for gathering, 3 more bedrooms with another en-suite master. The lower floor is a walkout to the stone patio that leads down to the amazing lined pond surrounded by incredible stone work, walls and perennial gardens giving you a truly breathtaking setting. The pond even features a waterfall incorporated into the stone work. 72.8 acres with accessible road frontage on Weston-Andover Rd. Possible future development. Just a short distance to Weston, several ski resorts, and VAST trails.

Renovated 4-Bedroom Farm In Chester
$339,000Est. Payment
4 Beds | -- Baths | 1,804 Sqft
124 Grafton Road, Chester, VT 05143
Farm For Sale

Superb 4 bedroom, 1.5 bath farmhouse in Chester village with fabulous chef's kitchen featuring an attractive island with Dekton counter and pendant lighting, stainless steel appliances and farmhouse stainless steel sink. A first floor laundry with sliding barn door and newly remodeled first floor half bath with novelty sink flank the welcoming foyer. The light-filled dining room with built-ins and bay window opens to the spacious living room with wood burning fireplace and built-in shelves for your library. The spacious second floor landing connects with four bedrooms and a beautifully renovated tiled full bath. The exterior has classic moldings and is accented by a lovely screened porch, stone patio with firepit, raised garden beds and attached barn. This exceptional location is within walking distance to town green, shops and other conveniences. An additional parcel was obtained to expand the yard which includes frontage along the Williams River! A restored classic front porch and thoughtful landscaping enhances the presence of this lovely home.

1518 SqFt House In Athens
$249,000Est. Payment
4 Beds | 1 Bath | 1,518 Sqft
107 Brookline Road, Athens, VT 05143
House For Sale

"Handy" Antique lovers wanted! An unspoiled historic farmhouse with great potential, being sold "AS IS" by the estate. Nice room sizes, an oversized attic for expansion, large attached barn/garage and about 10 exceptional open level acres. Most of the home is original but needs updsating to bring it to todays standards. The land borders Athens Brook and Mill Brook with large open spaces for gardens (or soccer) on both sides of home, and 3+ acres of woodland across the road for protection and firewood. also included is an adjoining 7 acre meadow, planted or mowed every year with a beautiful potential home site (no soil tests done). This house is worth restoring to it's former glory, in a beautiful setting. Almost everything on the premises (car excepted) at time of showing may be included, if desired - list of possible exclusions provided upon contract. Land totals 12.7 acres, by tax map, in 3 parcels. A great investment opportunity and rewarding project for a special Buyer. Drilled well.

1300 SqFt House In Andover
$249,000Est. Payment
1 Bed | 2 Baths | 1,300 Sqft
1264 East Hill Road, Andover, VT 05143
House For Sale

Built in 2016 this wonderfully crafted log home is a sight to behold. With fantastic views looking East out over Finn Hill,as it locally known, this is sure to please. Relax on the porch, take in the mountain breeze and enjoy a peaceful moment. The logs were locally sourced, milled and profiled to craft this comfy home. With a 2 bedroom septic you can expand and add more space. Don't Miss this chance to own a slice of heaven. The home is occupied so 48 hours notice is required to view it.

Restored 3-Bedroom House In Rockingham
$315,000Est. Payment
3 Beds | 2 Baths | 1,800 Sqft
118 Lower Bartonsville Road, Rockingham, VT 05143
House For Sale

Immaculately restored 1887 Brick home perched perfectly on a Vermont country road. This turn key home has been restored stylishly while maintaining all its original character and charm. The brand new front porch is perfect for sitting on a warm summer day. The side entry brings you into an open concept kitchen equipped with brand new Corian counter-tops, Kraft-made cabinetry, LG stainless appliances with a Bluetooth oven to set your meals to cook even while away. The impressive hardwood floors have been completely brought back to life and run through the kitchen, living room and brand new full bathroom with laundry. The cozy office is perfect for working from home! The rear of the house is home to three spacious bedrooms. The master suite with custom tile shower is bright clean and fresh! Open the slider out to the rear deck and this is where you will surly want to spend your time. With privacy and fully fenced yard you can lounge for hours. The massive garage doubles as a workshop and is perfect for your boat, ATV or all of your outside gear as well as space for 2 cars. With newer heating system , new hot water heater, new plumbing and electrical there is nothing left for you to do but move in and enjoy! A short walk to the Bartonsville Covered Bridge and less then 10 minutes I91 convenience and beauty surround you.

Lot In Andover
$99,000Est. Payment
3.32 Acres
1500 Andover Ridge Road, Andover, VT 05143
Lots Land For Sale

Not to be missed... if you are interested in building your Vermont home, look no further than this perfect mountaintop building lot with potential for sunrise AND sunset views! The beautiful wooded parcel offers a mix of hardwood and evergreen trees and has a pond site. The parcel has frontage on Andover Ridge Road and is from there or Stear Road. A Vermont wastewater permit for five bedrooms is in place, and this parcel is just waiting for you! Andover is centrally located and just a few minutes from Weston village (shops, galleries, restaurants and the wonderful Weston Playhouse offering live theater and music year-round), Ludlow (home of Okemo Ski Resort and lots of shops, restaurants and more) and Chester (one of Vermont's prettiest small towns with a great little book shop, antiques, restaurants and more).

864 SqFt House In Chester
$105,000Est. Payment
2 Beds | 1 Bath | 864 Sqft
5051 Vt Rt 103 N, Chester, VT 05143
House For Sale

Single level living with large two bay garage. This house is located an equal distance to Chester and Ludlow via VT RT 103, both offer small town shopping and dining. Ludlow is home to Okemo Mountain Ski Resort and is a short 10 minute drive. Bring your imagination with you when you view this property, the possibilities are endless.

Lot In Rockingham
$39,900Est. Payment
1.08 Acres
1441 Brockway Mills Road, Rockingham, VT 05143
Lots Land For Sale

If you are ready to build, here is the a plot of land that is ready to go! This land is permitted for a 3 bedroom home and has a state approved septic design. Drive by, check it out!

1122 SqFt House In Andover
$199,000Est. Payment
3 Beds | 1 Bath | 1,122 Sqft
356 Gates Road, Andover, VT 05143
House For Sale

This country charmer has it all. Quiet dirt road, yet quick access to the area's attractions and at just under half an acre this lovely parcel will be super easy to maintain. With a huge sugar house style barn there are lots of options to convert or just store all your toys. The screened in porch with hot tub and stunning forests and fields all around make this the perfect Vermont retreat. Just add you!! Come see today.

Lot In Andover
$65,000Est. Payment
-- Acres
00 North Hill Road, Andover, VT 05143
Lots Land For Sale

Located on a quiet country road, this building lot has a road roughed in and a home site cleared. Access to the VAST trail network at the top of the lot. Rural with easy access to Weston for shopping and the acclaimed Weston Playhouse and Ludlow for skiing and golf at Okemo Mountain Resort. Perked for a waste water system many years ago - engineering is needed to design a system. A peaceful environment to build your dream home.

Renovated Private House
$225,000Est. Payment
4 Beds | 2 Baths | 1,380 Sqft
63 Marshall Road, Chester, VT 05143
House For Sale

This beautiful home has been lovingly renovated very recently. The kitchen is brand new with all stainless steel appliances. With four bedrooms, a large master en suite and a main floor laundry offering convenience at home. With easy access to Chester village and best of all it is located in a beautiful neighborhood. The garage is large, 24 X 20, so plenty of room for toys and a workshop. Just like the garage; the back porch, roof, pellet stove and driveway are less than 2 years old. Every inch has been painted, improved and is ready to go. The private access to the South Branch of the Williams river is off the very private fenced in back yard and is simply charming. Come cool your toes and splash around a bit when you come to view this wonderfulhome.

1356 SqFt House In Chester
$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.