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 2 bay, 2 level barn offers 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.

Listing Tools

More Info

Tax Information

  • Tax Year2026

Parking

  • Parking Spaces2
  • GarageYes
  • Parking DescriptionDirect Entry, Heated Garage, Driveway, Garage, Off Street, On-Site, Unpaved, Barn, Attached

Rooms

  • Full Bath1

Basic Information

  • MLS Number5097722
  • MLS StatusActive
  • StatusACT
  • Property TypeSingle Family
  • List Price$750,000
  • Listing Agent NameKatherine Burns
  • Broker NameWilliam Raveis Real Estate Vermont Properties

Location

  • Building Number955
  • StreetSmokeshire Road
  • TownChester
  • StateVT
  • Zip05143
  • CountyWindsor
  • DistrictTwo Rivers Supervisory Union
  • Elementary SchoolChester-Andover Elementary
  • Junior HighGreen Mountain UHSD #35
  • High SchoolGreen Mountain UHSD #35
  • Flood Zone Y/NNo
  • Address955 Smokeshire Road

Building

  • Year Built2003
  • Building ConstructionWood Frame, Cedar Exterior
  • ConstructionExisting
  • Property StyleChalet, Contemporary, Multi-Level
  • Bedrooms3
  • Bathroom2
  • Total Baths2
  • 3/4 Baths1
  • Total Rooms9
  • Square Feet1,695
  • APX Unfin Below Grade1287
  • BasementConcrete, Concrete Floor, Full, Insulated, Interior Access, Interior Stairs, Storage Space, Unfinished
  • FoundationConcrete

Property

  • Acreage6.03
  • Lot DescriptionCountry Setting, Landscaped, Level, Open, River, River Frontage, Ski Area, Timber, Trail/Near Trail, Wooded, Near Golf Course, Near Shopping, Near Skiing, Near Snowmobile Trails, Near School(s)
  • AreaVT-Windsor
  • DrivewayDirt
  • RoadsDirt, Public, Public Maintained Road, Unpaved
  • Road Frontage610

Interior

  • Interior FeaturesBlinds, Cathedral Ceiling, Ceiling Fan, Dining Area, Wood Fireplace,1 Fireplace, Kitchen Island, Kitchen/Dining, Kitchen/Living, Living/Dining, Primary BR w/ BA, Natural Light, Skylight, Soaking Tub, Vaulted Ceiling, Walk-in Closet, Wood Stove Hook-up, Wood Stove Insert
  • Room 1 TypeLiving Room
  • Room 1 Level1
  • Room 1 Dimensions18'11 x 21'6
  • FloorsCarpet, Hardwood, Slate/Stone, Tile
  • Room 2 TypeKitchen
  • Room 2 Level1
  • Room 2 Dimensions9'8 x 13'3
  • Room 3 TypeDining Room
  • Room 3 Level1
  • Room 3 Dimensions9'3 x 13'3
  • Room 4 TypePrimary Bedroom
  • Room 4 Level1
  • Room 4 Dimensions16'10 x 15'6
  • Room 5 TypeBathroom Full
  • Room 5 Level1
  • Room 5 Dimensions10'2 x 10'
  • Stories1.5
  • Room 6 TypeBedroom
  • Room 6 Level1
  • Room 6 Dimensions13'8 x 10'2
  • Room 7 TypeBedroom
  • Room 7 Level1
  • Room 7 Dimensions13'8 x 9'10
  • Room 8 TypeBathroom Three Quarter
  • Room 8 Level1
  • Room 8 Dimensions9'10 x 8'6
  • Room 9 TypeLoft
  • Room 9 Level2
  • Room 9 Dimensions18'11 x 15'1

Exterior

  • Exterior FeaturesBarn, Deck, Hot Tub, Natural Shade, Porch, Screened Porch, Storage
  • RoofShingle

Utilities

  • Heat SystemOil, Baseboard, Hot Water, Multi Zone, Wood Stove
  • WaterDrilled Well
  • Sewer1000 Gallon, Leach Field, Septic
  • ElectricCircuit Breaker(s)
  • UtilitiesUnderground Utilities

Amenities

  • AmenitiesCO Detector, Smoke Detector, Wood Stove
  • PetsYes
  • PricePerSqFt442.48

Water Body

  • Water Body NameWilliams River
  • Water Body TypeRiver
  • Water AccessOwned
  • Water ViewYes

Other

  • SeasonalNo
  • Page120-121
  • Date Listed07/01/2026
  • View Count1

Map Location

Listed by Katherine Burns of William Raveis Real Estate Vermont Properties (Off: 802-228-8877)
Broker Reciprocity 

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated July 2, 2026 7:53 AM UTC

 

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