Gorgeous renovated Colonial offering exceptional flexibility, thoughtful design, and timeless charm. This beautifully updated property features a spacious main residence along with a stunning addition that includes a full in-law suite and a private studio above-ideal for guests, extended family, a home office, or potential rental income. Solar panels installed above the garage power efficient mini-split systems, and a Tesla Powerwall provides added energy independence and peace of mind. The main house offers four bedrooms, a fabulous chef's kitchen with quality finishes and generous workspace, and warm, inviting living areas filled with abundant natural light. Magnificent views of Mount Anthony and the sweeping five-acre meadow below can be enjoyed from the kitchen, dining room, living room, and screened porch-where wildlife is often part of the daily landscape. A new large enclosed porch further expands the living space, creating the perfect setting to relax or entertain year-round. Set on 17+ picturesque acres framed by classic stone walls, the property offers lovely views, open meadow, and wooded privacy with ample outdoor space to explore and enjoy. A three-car detached garage provides excellent space for vehicles, storage, or hobby use, while a workshop and spacious woodshed add exceptional functionality. Equestrian enthusiasts will appreciate the charming pony barn and paddock, completing this truly special setting. A rare opportunity to own a beautifully expanded home with multiple living options, sustainable features, and breathtaking views in a serene and private landscape.

Listing Tools

More Info

Tax Information

  • Tax Year2026

Parking

  • Parking Spaces3
  • GarageYes
  • Parking DescriptionAuto Open, Driveway, Garage, Parking Spaces 1 - 10, Detached

Rooms

  • Full Bath3

Basic Information

  • MLS Number5077720
  • MLS StatusActive
  • Virtual TourView Tour
  • StatusACT
  • Property TypeSingle Family
  • List Price$1,495,000
  • Listing Agent NameKelley McCarthy
  • Broker NameMahar McCarthy Real Estate

Location

  • Building Number557
  • StreetBennett Hill Road
  • TownShaftsbury
  • StateVT
  • Zip05262
  • CountyBennington
  • DistrictSouthwest Vermont
  • Elementary SchoolShaftsbury Elem. School
  • Junior HighMt. Anthony Union Middle Sch
  • High SchoolMt. Anthony Sr. UHSD 14
  • Flood Zone Y/NNo
  • Address557 Bennett Hill Road

Building

  • Year Built1963
  • Building ConstructionCedar Exterior, Clapboard Exterior, Shake Siding, Wood Siding
  • ConstructionExisting
  • Property StyleColonial
  • Bedrooms6
  • Bathroom6
  • Total Baths6
  • 3/4 Baths2
  • Half Bath1
  • Total Rooms13
  • Square Feet4,864
  • APX Unfin Below Grade1440
  • BasementBulkhead, Concrete, Concrete Floor, Unfinished, Exterior Access, Basement Stairs
  • FoundationConcrete, Concrete Slab

Property

  • Acreage17.83
  • Lot DescriptionCountry Setting, Field/Pasture, Landscaped, Level, Mountain View, Stream, View
  • AreaVT-Bennington
  • DrivewayCircular, Crushed Stone
  • RoadsPublic, Public Maintained Road
  • Road Frontage500

Interior

  • Interior FeaturesBar, Cathedral Ceiling, Ceiling Fan, Gas Fireplace, Wood Fireplace,2 Fireplaces, In-Law/Accessory Dwelling, In-Law Suite, Kitchen Island, Primary BR w/ BA, Natural Light, Soaking Tub, Vaulted Ceiling, Walk-in Closet, Wet Bar, Programmable Thermostat
  • Room 1 TypeKitchen
  • Room 1 Level1
  • Room 1 Dimensions19'3x12'9
  • FloorsCarpet, Hardwood, Tile, Wood
  • Room 2 TypeLiving/Dining
  • Room 2 Level1
  • Room 2 Dimensions19x13
  • Room 3 TypeLiving Room
  • Room 3 Level1
  • Room 3 Dimensions19'4x16
  • Room 4 TypeDining Room
  • Room 4 Level1
  • Room 4 Dimensions14'5x15'1
  • Room 5 TypeFamily Room
  • Room 5 Level1
  • Room 5 Dimensions15'9x11'5
  • Stories2
  • Room 6 TypePrimary BR Suite
  • Room 6 Level2
  • Room 6 Dimensions19x15'1
  • Room 7 TypeBedroom with Bath
  • Room 7 Level2
  • Room 7 Dimensions17x16
  • Room 8 TypeBedroom
  • Room 8 Level2
  • Room 8 Dimensions12'6x13'3
  • Room 9 TypeBedroom
  • Room 9 Level2
  • Room 9 Dimensions12'7x15
  • Room 10 TypeBedroom
  • Room 10 Level1
  • Room 10 Dimensions12x15
  • Room 11 TypeLiving Room
  • Room 11 Level1
  • Room 11 Dimensions23x12
  • Room 12 TypeKitchen
  • Room 12 Level1
  • Room 12 Dimensions7'10x9'6
  • Room 13 TypeStudio
  • Room 13 Level2
  • Room 13 Dimensions21x15
  • Room 14 TypeBathroom Full
  • Room 14 Level2
  • Room 15 TypeBathroom Full
  • Room 15 Level2
  • Room 16 TypeBathroom Three Quarter
  • Room 16 Level2
  • Room 17 TypeBathroom Full
  • Room 17 Level2
  • Room 18 TypeBathroom Three Quarter
  • Room 18 Level1
  • Room 19 TypeBathroom Half
  • Room 19 Level1

Exterior

  • Exterior FeaturesPartial Fence, Garden Space, Natural Shade, Outbuilding, Patio, Porch, Enclosed Porch, Screened Porch, Storage, Window Screens
  • Exterior ColorWhite
  • RoofMetal, Architectural Shingle, Standing Seam

Utilities

  • Heat SystemPropane, Baseboard, Multi Zone, Radiant, Mini Split, Boiler, Gas Fireplace
  • WaterDrilled Well
  • SewerSeptic
  • Electric200+ Amp Service, Circuit Breaker(s)
  • UtilitiesCable Available, Propane

Amenities

  • Accessibility Amenities1st Floor 1/2 Bathroom,1st Floor 3/4 Bathroom, Kitchen w/5 Ft. Diameter, Low Pile Carpet,1st Floor Laundry
  • AmenitiesCO Detector, Dehumidifier, Radon Mitigation, Smoke Detector, Hardwired Smoke Detector
  • PricePerSqFt307.36

Other

  • SeasonalNo
  • Page68-71
  • Date Listed02/27/2026
  • View Count3

Map Location

Listed by Kelley McCarthy of Mahar McCarthy Real Estate
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 March 14, 2026 9:52 PM EDT

 

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