557 Bennett Hill Road

Active Under Contract
Active Under Contract
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Contract Out
$1,450,000
6 beds4,864 sqft
557 Bennett Hill Rd, Shaftsbury, VT 05262
Est: $9,340/moGet pre-approved
Single FamilyProperty Type
17.83 acresLot Size
1963Year Built
$298/sq ftPrice per sq ft
3 carsParking Spaces

Description

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...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.
172 days on Market
  • Listed by: Kelley McCarthy • Mahar McCarthy Real Estate
Last updated: 08/24/2026 05:27 PM • Source: New England Real Estate Network, MLS#: 5077720

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$9,340 per month

30 year fixed, 7.03% Interest

Principal and Interest

$7,741

Property Taxes

$1,599

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Property Information for 557 Bennett Hill Road

Property Details
  • Taxes: $19,189 / year
  • MLS Type: Residential / Single Family
  • County: Bennington County
  • Zoning: RR
Building Information
  • Stories: 2
  • Year Built: 1963
  • Lot Size: 17.83 AC / 776,674 SF
Summary
Location and General Information
  • City: Shaftsbury
  • County: VT-Bennington
  • Latitude: 42.970157000001002
  • Longitude: -73.237844999999993
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05262
Taxes and HOA Information
  • SPAN Number: 573-180-11760
  • Tax Year: 2026
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 3.00
  • Driveway: Circular, Crushed Stone
Property
Lot Information
  • Lot Features: Country Setting, Field/Pasture, Landscaped, Level, Mountain View, View
  • Lot Size Acres: 17.83
  • Road Frontage Length: 500.0
  • Water Body Access: No
  • Total Finished Area: 4864.0
  • Above Grade Finished Area: 4864.0
  • Above Grade Finished Area Source: Assessor
  • Above Grade Unfinished Area: 0.0
  • Below Grade Finished Area: 0.0
  • Below Grade Unfinished Area: 1440.0
  • BelowGradeUnfinishedAreaSource: Assessor
  • Lot Size Square Feet: 776675.0
  • Total Area: 6304.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Property Condition: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Resort: No
  • Surveyed: Unknown
  • Year Built: 1963
  • School District: Southwest Vermont
  • High School: Mt. Anthony Sr. UHSD 14
  • Middle/Jr School: Mt. Anthony Union Middle Sch
  • Elementary School: Shaftsbury Elem. School
Utilities
  • Fuel Company: Suburban propane
  • Electric: 200+ Amp Service, Circuit Breaker(s)
  • Sewer: Septic
  • Water Source: Drilled Well
  • Utilities: Cable Available, Propane
  • Internet: Fiber Optic Internt Avail
Interior and Exterior Features
Exterior Features
  • Color: White
  • Construction Materials: Cedar Exterior, Clapboard Exterior, Shake Siding, Wood Siding
  • Roof: Architectural Shingle, Metal, Standing Seam
Interior Features
  • Appliances: Dishwasher, Dryer, Range Hood, Microwave, Wall Oven, Gas Range, Refrigerator, Washer, On Demand Water Heater, Owned Water Heater, Wine Cooler
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Bulkhead, Concrete, Concrete Floor, Unfinished, Exterior Access, Basement Stairs
  • Rooms: Level 1: Level 1: Bedroom, Level 1: 1/2 Bathroom, Level 1: 3/4 Bathroom, Level 1: Dining Room, Level 1: Family Room, Level 1: Kitchen, Level 1: Living/Dining, Level 1: Living Room
  • Rooms: Level 2: Level 2: Bedroom, Level 2: Full Bathroom, Level 2: 3/4 Bathroom, Level 2: Primary Bdm Ste, Level 2: Studio
  • Flooring: Carpet, Hardwood, Tile, Wood
  • Heating: Propane, Baseboard, Multi Zone, Radiant, Mini Split, Boiler, Gas Fireplace
  • Cooling: Mini Split
  • Total Stories: 2
  • Rooms Total: 13
  • Bathrooms Full: 3
  • Bathrooms Half: 1
  • Bathrooms One Quarter: 0
  • Bathrooms Three Quarter: 2
  • Bedrooms Total: 6
  • Bathrooms Total: 6
Room Information
Room 1
  • Room Dimensions: 19'3x12'9
  • Room Level: 1
  • Room Type: Kitchen
Room 2
  • Room Dimensions: 19x13
  • Room Level: 1
  • Room Type: Living/Dining
Room 3
  • Room Dimensions: 19'4x16
  • Room Level: 1
  • Room Type: Living Room
Room 4
  • Room Dimensions: 14'5x15'1
  • Room Level: 1
  • Room Type: Dining Room
Room 5
  • Room Dimensions: 15'9x11'5
  • Room Level: 1
  • Room Type: Family Room
Room 6
  • Room Dimensions: 19x15'1
  • Room Level: 2
  • Room Type: Primary BR Suite
Room 7
  • Room Dimensions: 17x16
  • Room Level: 2
  • Room Type: Bedroom with Bath
Room 8
  • Room Dimensions: 12'6x13'3
  • Room Level: 2
  • Room Type: Bedroom
Room 9
  • Room Dimensions: 12'7x15
  • Room Level: 2
  • Room Type: Bedroom
Room 10
  • Room Dimensions: 12x15
  • Room Level: 1
  • Room Type: Bedroom
Room 11
  • Room Dimensions: 23x12
  • Room Level: 1
  • Room Type: Living Room
Room 12
  • Room Dimensions: 7'10x9'6
  • Room Level: 1
  • Room Type: Kitchen
Room 13
  • Room Dimensions: 21x15
  • Room Level: 2
  • Room Type: Studio
Room 14
  • Room Level: 2
  • Room Type: Bathroom Full
Room 15
  • Room Level: 2
  • Room Type: Bathroom Full
Room 16
  • Room Level: 2
  • Room Type: Bathroom Three Quarter
Room 17
  • Room Level: 2
  • Room Type: Bathroom Full
Room 18
  • Room Level: 1
  • Room Type: Bathroom Three Quarter
Room 19
  • Room Level: 1
  • Room Type: Bathroom Half

Property History for 557 Bennett Hill Road

DateEvent & SourcePriceAppreciation
Aug 18, 2026

Active Under Contract

New England Real Estate Network #5077720

—
Feb 27, 2026

Listed (Active)

New England Real Estate Network #5077720

$1,495,000—
Jul 1, 2022

Sold (Public Record)

Public Record #1493697789

$1,100,000

+3.9% / yr

DateEvent & SourcePrice
08/18/2026

Active Under Contract

New England Real Estate Network #5077720

—
02/27/2026

Listed (Active)

New England Real Estate Network #5077720

$1,495,000
07/01/2022

Sold (Public Record)

Public Record #1493697789

$1,100,000

+3.9% / yr

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 557 Bennett Hill Road

Taxable ValueLand$172,800Additions$466,900Total$639,700
Tax Record2025$8,771 ($731 / month)
Home Facts
Beds6Baths5.5Total Finished SqFt4,864 SqFtAbove Grade Finished SqFt4,864 SqFtUnfinished Basement SqFt120 SqFtStories2Lot Size776,675 SqFtStyleSingle Family ResidenceYear Built1963Year Renovated1963CountyBENNINGTONAPN(180)082062

Schools near 557 Bennett Hill Road

This home is within Mount Anthony Union High School District #14.
Rating
School
Type
Grades
Distance
Shaftsbury Elementary School
Public - PK to 6
Mt. Anthony Union Middle School
Public - 6 to 8
Mt. Anthony Senior Uhsd #14
Public - 9 to 12
Molly Stark School
Public - PK to 5
Rating
School
Distance
Shaftsbury Elementary School
PublicPK to 6

Mt. Anthony Union Middle School
Public6 to 8

Mt. Anthony Senior Uhsd #14
Public9 to 12

Molly Stark School
PublicPK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Listing Courtesy of Mahar McCarthy Real Estate

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 10/02/2026 07:34 AM