
Land with Home for Sale in Chester, Vermont
955 Smokeshire Rd, Chester, VT 05143
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.
Location
- Street address
- 955 Smokeshire Rd
- County
- Windsor County
- Zip code
- 05143
- School district
- Two Rivers Supervisory Union
- Elevation
- 971 feet
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
| Name | Type | District |
|---|---|---|
| Chester-Andover Elementary | Elementary | Two Rivers Supervisory Union |
| Green Mountain UHSD #35 | Middle | Two Rivers Supervisory Union |
| Green Mountain UHSD #35 | High | Two Rivers Supervisory Union |
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| July 1, 2026 | New listing | $750,000 | — | NNEREN |
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