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Land with Home for Sale in Chester, Vermont

955 Smokeshire Rd, Chester, VT 05143

$750,000
6 acres
Active sale
ago
Est $4,774/mo

Tucked away on a quiet country road in one of Chester's most coveted areas, this striking contemporary home offers the ultimate Vermont lifestyle-just miles from the Okemo Mountain base lodge. Embraced by nature and thoughtful landscape, the property seamlessly connects refined indoor living with the natural beauty of its private riverfront, complete with your own summer swimming hole. Inside, the main level centers around a commanding, floor-to-ceiling fieldstone wood-burning fireplace, beautifully complemented by rich hardwood floors and a bespoke custom kitchen. Designed for privacy, the primary suite features a spa-like ensuite bath, while two additional guest bedrooms and a 3/4 bath provide plenty of space for family or weekend visitors. Intelligently designed for flexible living, the upper-level loft serves as an inspiring home office or studio, while the bright, walk-out lower level offers incredible potential for a game room, home gym, or ski lounge. Transition effortlessly outdoors to the oversized front deck for morning coffee, or unwind in the expansive screened porch out back listening to the sound of the river. The detached, insulated, oversized, 2-bay, 2-level barn has full electrical service, electric garage doors, and a workshop with extra storage space. There is a greenhouse perfect for gardening. With direct access to nearby VAST trails for winter recreation, this is a true four-season retreat. Visit the Okemo real estate today. Taxes are based on current town assessment.

1,695
Sq feet
3
Beds
1
Full bath
1
3/4 bath
2003
Built

Location

Street address
955 Smokeshire Rd
Zip code
05143
School district
Two Rivers Supervisory Union
Elevation
971 feet
Coordinates
43.3455, -72.6393

Directions

From Ludlow, follow Route 103 south. Turn right onto Smokeshire Road. The house is on the left side. No sign.

Property details

Acreage
6.03 acres
Zoning
Residential
MLS #
NNEREN 5097722
Posted

Property taxes

2026
$11,303

Details and features

Listing

Type
Residential

Lot

Waterfront
Yes
Features
Country Setting, Landscaped, Level, Near Golf Course, Near School(s), Near Shopping, Near Skiing, Near Snowmobile Trails, Open, River, River Frontage, Ski Area, Timber, Trail/Near Trail, Wooded

Exterior

Parking
Driveway, Garage, Off Street, Paved or Surfaced
Pool
Deck, Porch
Structures
Storage
Features
Barn, Hot Tub, Natural Shade, Screened Porch

Structure

Style
Contemporary
Stories
2
Water
Well
Heating
Baseboard, Ductless, Hot Water, Oil, Wood, Wood Stove
Cooling
Multi Units, Zoned
Materials
Cedar Exterior, Wood Frame
Roof
Shingle

Interior

Room Count
9
Rooms
Basement, Bathroom x 2, Bedroom x 3, Dining Room
Flooring
Carpet, Hardwood, Slate, Tile
Appliances
Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Washer
Features
1 Fireplace, 1st Floor Laundry, Blinds, Cathedral Ceiling, Ceiling Fan, Dining Area, Kitchen Island, Kitchen/Dining, Kitchen/Living, Living/Dining, Natural Light, Primary BRW/BA, Skylight, Soaking Tub, Vaulted Ceiling, Walk-In Closet, Wood Fireplace

Nearby schools

NameTypeDistrict
Chester-Andover ElementaryElementaryTwo Rivers Supervisory Union
Green Mountain UHSD #35MiddleTwo Rivers Supervisory Union
Green Mountain UHSD #35HighTwo Rivers Supervisory Union

Listing history

DateEventPriceChangeSource
July 1, 2026New listing$750,000NNEREN
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This 6.03-acre property is located at 955 Smokeshire Rd in Chester, VT 05143. The property is available for sale, priced at $750,000. It has a 1,695 square foot 3-bedroom, 2-bath house built in 2003.

Listed by William Raveis Real Estate Vermont Properties, (802) 228-8877

Checked 2 hours agoUpdated Source

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Katherine Burns
Katherine Burns
William Raveis Real Estate Vermont Properties
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