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78 Homes For Sale in Chester, VT

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$269,000Est. Payment
3 Beds | 2 Baths | 2,208 Sqft

141 Dorman Road, Andover, VT 05143

House For Sale

Mature gardens and the deep water spring fed pond are just a few attributes of the beautiful setting of this private idaho on Dorman Rd. Set back from the quiet dead end road, shared with about a dozen homes is this well cared for ranch home. Pull right into your attached two car garage and stay out of the elements. Enter the home and you have the option to go directly into the large laundry room. The eat in kitchen with granite counters, stainless appliances has wonderful screened in porch for summer dinning or just hanging. Large living room with fireplace and formal dinning room top off the living space of main floor. Three bedrooms and two baths including the master suite with walk in closet are all on the east wing of this ranch. Downstairs to to a large living space with wood stove, larger storage area and spacious workshop. Out buildings can include green house and storage shed. All of this on over 4 private acres with direct access to snowmobiling on the VAST trail network.

New
$175,000Est. Payment
3 Beds | 1 Bath | 1,340 Sqft

62 Davidson Hill Road, Chester, VT 05143

House For Sale

Charming, bucolic setting with easy access to Ludlow, Chester and Woodstock. Grapes, blueberry bushes, large deck, smaller deck as well as a private balcony off the second floor bedroom. A short drive off the main road for easy access...Sits up high and is set back from the road for privacy and prestige. 15 Minutes to Downtown Ludlow, 10 to Chester. Large Fenced in area to one side of the home for your pets to play. The current owners have put a lot of TLC over the years into making this a very welcoming, very comfortable second home to spend time with friends and family. If you're looking for your own special place (whether it be seasonal, occasional or year-round) here in ski country...you owe it to yourself to come take a look.

$239,000Est. Payment
3 Beds | 2 Baths | 1,591 Sqft

3851 Trebo Road, Chester, VT 05143

House For Sale

Great opportunity to own in Chester! Pretty post and beam home and nice country road. Stonewalls, fruit trees and berry bushes adorn the back yard. Radiant heat with wonderfully open main level floor plan. Mudroom, enclosed screened porch, attached garage and large pantry all make this a must see! Only minutes to downtown Chester and easy access to Springfield.

$750,000Est. Payment
10 Beds | 12 Baths | 6,848 Sqft

698 Vermont Rt 11 Route, Chester, VT 05143

House For Sale

An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.

$124,900Est. Payment
83 Acres

1227 Howard Hill Road, Andover, VT 05143

Lots Land For Sale

Heres a wonderful opportunity to build your dream home on 83 +/- acres on the well-regarded Howard Hill Road in Andover, VT! With a rolling topography, the property offers potential for gorgeous mountain views with some clearing. The westerly side of the parcel will make for an excellent private home site with a probable walk-out basement. The property features a large brook that runs down center of property and many trails throughout allowing for easy access to the bulk of the acreage. Recreational possibilities abound with the land appearing to be excellent hunting territory. The majority of the property is enrolled in the states Current Use tax reduction program with a future potential 10-acre building site along the westerly side of the property conveniently excluded from the program. The parcel is predominantly mature northern hardwoods with some softwoods stands in the lower elevations. Per the timber report, the property is due to be reexamined by a forester in 2022 and a cut may be available. With 2-acre zoning, there may be development potential, if appropriate septic is identified per state regulations. Power is located at the road along with phone & high speed fiber internet. Howard Hill Road is a year-round, town maintained & plowed road with many beautiful country homes. Tater Hill Country Club is one minute away & several world class ski resorts like Okemo, Bromley & Stratton are within a 30 min drive. Parcel has been formally surveyed & is well-marked.

$194,500Est. Payment
3 Beds | 1 Bath | 1,700 Sqft

780 Farrar Road, Chester, VT 05143

House For Sale

Unique, well-maintained, and private home off a charming gravel Vermont road. It is a custom cottage with a terrific deck overlooking a very special view. Home has been tended by an avid gardener, and many perennials, blueberries and fruit trees adorn the property. Time to get you hands into the earth! Very nice fields and a small wooded area have the start of a tree farm, and plenty of room for animals. There is also a grape arbor. Inside you will find a large and open kitchen/dining area, L-shaped living room with skylights, and three bedrooms and bath, all new sheet rock, doors and paint. The very dry poured concrete basement has a finished room, which could be a bedroom, wine or media room, and lots of additional storage. Part of the basement has a nice workbench and shelving, with egress to a new workshop/utility shed with loft, 16X12. There is also a washer/dryer in the basement. 30 minutes from Stratton, Bromley, Magic and Okemo Mountains, and an hour from Killington. Three golf courses are also nearby. There is also Cable (xfinity) and VTEL Fiber Optic fast internet service. Bring your imagination, and plan to do wonderful things with your new mountain home!

$200,000Est. Payment
146 Acres

269 Schmidt Road, Andover, VT 05143

Lots Land For Sale

Nestled in the rolling hills of Andover, Vermont is Three Waters Retreat a 146 +/- acre ideal recreational property with a state-issued wastewater permit for a 5-bedroom, year-round residential home! Perfect for an outdoorsman or a homesteader, the property offers a tranquil refuge from the daily rigors of life with beautiful mountain views, over 2,555 of river frontage along Williams River, mountain streams that feed into the river, and an abundance of wildlife signs throughout. Setback from a town-maintained and plowed Class III road, the property features an existing driveway, unfinished cabin with a sleeping loft, an installed septic system, and a partially dug hole for the foundation of the proposed 5-bedroom homesite. It is our understanding that the septic system was installed in accordance with the wastewater permit for the property and is not connected to the existing cabin. The closest utility pole is located nearby the driveway along Schmidt Road & is approx. 450 from the proposed homesite. VTel offers high speed internet, TV & telephone services to homes along the nearby E Hill Road. Completely surrounded by forest, the year-round recreational possibilities are seemingly endless both on & off the land from hiking & ATVing to cross country skiing & snowmobiling. Excellent proximity to White River Junction and Rutland. Okemo Mountain Resort & Lake Rescue nearby! The land conveys subject to ROWs. Property is enrolled in Current Use offering reduced taxes!

$649,000Est. Payment
2 Beds | -- Baths | 7,610 Sqft

92 Vt Rte 11 West Route, Chester, VT 05143

House For Sale

Built and operated as a successful retail/eat-in bakery/cafe for 20 years, this fascinating structure on 3.5+/- level acres offers possibility for use as a full time residence with a home business, or, with further modification, a unique and spectacular full time home. The amazing cathedral like structure was built in 1997 on an old homestead and attached to the barn which dates back to 1850s. The entire interior is connected and finished as one seamless space. There is a 4-flu chimney which could be made into a beautiful stone fireplace. The open floor plan could be redesigned for living space. The possibilities are endless. 4 bathroom spaces are in place with two half baths to code for public use and two more bath areas with a walk-in tiled shower. A home business such as a dance studio, music space, or any form of retail business would work very well with flexible options as to where the business entrance would be. Walking distance to town, adjoins town rec area. Delayed showings until Aug. 3.

$489,000Est. Payment
3 Beds | 3 Baths | 4,196 Sqft

591 Remington Road, Chester, VT 05143

House For Sale

Don't miss this country gem tucked away in a quiet subdivision on the outskirts of Chester! The expansive wrap-around covered porch adds charm and added outside floor space to the home. The open, eat-in kitchen is ideal for preparing meals while enjoying family and friends. Custom wood-paneledcathedral ceilings offer impressive spacial quality to the common room, while the floor to ceiling brick fireplace offers a both focus and function. The dining room shares the same grand space. A stately master suite includes a large soaking tub, shower stall, expansive walk-in closet, and two access points to the wrap around porch and rear deck. Additionally, a laundry room, a half bath and ample screened porch enhance the main level. A lovely balcony highlight the upper level overlooking the first floor common area. It also provides ready access to two bedrooms, a stunning library, a sewing/craft room, and a full bath. The finished walkout basement was once home to a family business adding extra walkout living space. It currently enjoys a conference and office areas with multiple phone linesin place. High speed fiber optic internet offers a "work from home" option. A second adjacent lot is included with the sale! This property is private, spacious, and only a short distance to I-91, as well as Chester Village conveniences.

$369,000Est. Payment
1 Bed | 1 Bath | 1,584 Sqft

60 Colburn Road, Chester, VT 05143

House For Sale

Have you ever dreamed of operating your own farm in a picturesque Vermont town? Take advantage of this rare opportunity to expand on this spacious stone structure, situated on 102 acres, surrounded by open fields, woodlands, and the Williams River. Recovering from a fire in 2012, the interior has been reconstructed and ready for you to craft it into the home you've always desired! Enjoy the variety of agriculture embedded on the land, including 13+/- acres of crop fields + orchards! Pick from the organic blueberry farm and host many delicious meals featuring lots of flavor from your garlic + herb gardens! Find serenity in your established perennial gardens, or skip rocks along the trout pond with friends and family. Nature is no stranger to this residence as the land features a large 30x70 chicken coop and honey bees to pollinate the gardens! Adventurer at heart? This amazing location is only minutes away from the Okemo Mountain Resort and offers private access to the V.A.S.T. snowmobile trail! Bordering 30+ acres of preserved habitat, you will love the ease of country living in this historic 2-story home. Schedule your showing, today!

$289,000Est. Payment
3 Beds | -- Baths | 1,440 Sqft

2187 North Hill Road, Andover, VT 05143

House For Sale

This Vermont Saltbox in Andover offers the perfect opportunity to own a slice of paradise at an affordable price. There are gorgeous flourishing gardens and a custom brick patio that overlooks the backyard. Walk along the trails in the woods or sip coffee on the front porch and observe the old stone wall that sits quietly in front of you. Sun seeps into the living room, dining room and kitchen through the large windows. There are three bedrooms and two bathrooms on a manageable and magical two acres. What makes this spot so unique? It's a newer home, circa 1986 and was made to look antique. There is a large heated garage, exposed wood beam ceilings, radiant floors and has fiber optic WiFi access. The house also features a quintessential and inviting mudroom as you first walk into the home. Just a short distance to the VAST trails. See why this should make your list of must-sees. Less than 15 minutes to Ludlow and Okemo Mountain.

$759,000Est. Payment
4 Beds | 4 Baths | 4,700 Sqft

7050 Popple Dungeon Road, Windham, VT 05143

House For Sale

Experience all Vermont has to offer from this classic Timberpeg home. The Great Room, timbered and vaulted, invites all to gather around the soaringstone fireplace, large open dining area and expanded gourmet kitchen. A screened in porch and lovely deck overlook the golf course. This four bedroom, three and a half-bath home can easily accommodate family and friends. First floor Master Bedroom with en suite bath. Two guest bedrooms on the second floor with office area. The spacious walkout Lower level features an entertainment center, family room and second master with en suite. Designed to accommodate recreational equipment the large over sized 2 car garage opens onto a mud room complete with laundry. Skiing is just a short drive to Stratton, Okemo or Magic Mountains. Bordering the Tater Hill Golf Course. Music and Drama at the famed Weston Playhouse. Come take a look at this spectacular Vermont home!

$209,000Est. Payment
4 Beds | 1 Bath | 1,632 Sqft

125 Whitmore Brook Road, Chester, VT 05143

House For Sale

Tucked away on a quiet town road between Ludlow and Chester is this 4 bedroom home with lots of natural light, wood floors and open beams. Large open floor plan downstairs with a big updated kitchen, dining area and large living room with a stone hearth and gas burning stove. Enjoy the 2 +/- acres with an ample yard, matured landscaping & wooded trails. Poured slab for a garage. Would make a great ski house only 6 miles to Jackson Gore/ Okemo, Ludlow and all the amenities it has to offer.

$235,000Est. Payment
3 Beds | 1 Bath | 1,889 Sqft

2155 Vt Route 11 East Route, Chester, VT 05143

House For Sale

Dreaming of having your own business space and live on-premises? This charming 1830's brick home with fully restored barn, might be just the right property! The home was carefully renovated with keeping all the original character in mind. Welcome yourself through the main entry to find an interior brick wall in the open concept kitchen and dining area. This room is warmed with beautiful softwood floors and plenty of natural light from the large picture windows on both south and north side of the home. The living area is equipped with a soapstone wood stove and will surely provide ample heat. An office, 3/4 bath, and first floor master complete the main living level. Two spacious bedrooms on the second story are bright and perfect for extra guest space if needed. The barn is what will really pique your interest having been fully renovated structurally and cosmetically. This was once home to a bustling antique shop and offered great exposure being on Route 11, nestled between Chester and Springfield. Let your imagination soar with all the possibilities this unique property has to offer!

$94,500Est. Payment
13.34 Acres

00 Hill Top Road, Andover, VT 05143

Lots Land For Sale

Beautiful 13.34 acre parcel with views and privacy in Andover! State approved septic for four bedroom home with a one bedroom apartment over the garage. Cleared access to the house site with electricity at the lot. Gently rolling and sloping land with old fruit trees and VAST trail access. Close to Okemo, Stratton, Magic and Bromley ski areas. Golf, kayaking and cross country skiing nearby. A short drive to Ludlow, Chester and Weston.

$10,000
$199,000Est. Payment
2 Beds | -- Baths | 2,196 Sqft

3466 Rte 103 North Highway, Chester, VT 05143

House For Sale

Looking for the next stewards of this unique 2 bedroom, 2 bath Chester Schoolhouse/home on .76 acres+/-. A schoolhouse until the early 1960's, the property was then creatively modified for residential living and has been owned and cared for by a writer and a photographer. Accessed off a major road, the property also fronts along a quiet country lane and features a pond site, stone walls and beautiful country setting. The original schoolroom is spacious as a main living area and features the original blackboard, maps, large schoolroom windows, high ceiling, soapstone wood stove and original maple flooring. The updated kitchen has a professional style gas/convection stove with double ovens and breakfast bar pass-through and will bring out your inner chef! A spiral staircase leads to a spacious second floor bedroom/studio with interesting exposed structural beams. The expansive Master bedroom/living space features a vaulted ceiling, built-in shelving, private full bath, wood stove and rear deck/balcony overlooking the private yard and country setting beyond. Other features include a large, convenient first floor laundry area, enclosed sun porch, patio and attached 2-car garage. This unique historic property would even work well as an Air B&B, or home business with commercial zoning. Truly one of a kind! Close to skiing and centrally located to shopping and recreation.

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