557 Bennett Hill Rd

Shaftsbury, VT 05262

$1,495,000
Price
6
Beds
4,864 Sq. Ft.
$307 / Sq. Ft.
4,864
Sq. Ft.
$307
per Sq. Ft.
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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.
  1. Listed by Kelley McCarthy • Mahar McCarthy Real Estate

Property Details for 557 Bennett Hill Road

Zoning
RR
LISTING UPDATED: 02/27/2026 06:34 PM

Property Details for 557 Bennett Hill Road

StatusActive
MLS #5077720
Days on Market26
Taxes$12,610 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1963
Lot Size17.83 AC / 776,674 SF
CountyBennington County
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Location

Listing Courtesy of Mahar McCarthy Real Estate
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Building Information for 557 Bennett Hill Road

Stories2Year Built1963Building Size-Lot Size17.83 AC / 776,674 SF

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$8,306 per month

30 year fixed, 6.11% Interest

Principal and Interest

$7,255

Property Taxes

$1,051

HOA Dues

$0

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Property Information for 557 Bennett Hill Road

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, Stream, View
  • Lot Size Acres: 17.83
  • Road Frontage Length: 500.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Resort: No
  • Surveyed: Unknown
  • Year Built: 1963
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: Metal, Architectural Shingle, 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
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
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

Jul 8, 2016

Expired

New England Real Estate Network #3060254

—
Nov 19, 2012

Expired

New England Real Estate Network #4165496

—
Jun 13, 2012

Listed (Active)

New England Real Estate Network #4165496

$745,000—
May 23, 2012

Expired

New England Real Estate Network #4065251

—
May 23, 2011

Listed (Active)

New England Real Estate Network #4065251

$950,000—
Sep 12, 2008

Listed (Active)

New England Real Estate Network #3060254

$1,095,000—
Jun 18, 2008

Expired

New England Real Estate Network #3042418

—
Jun 18, 2007

Listed (Active)

New England Real Estate Network #3042418

$1,300,000—
Jan 15, 2005

Expired

New England Real Estate Network #3082924

—
Aug 2, 2004

Sold (Public Record)

Public Record #547329087

$550,000—
Aug 2, 2004

Sold (Public Record)

Public Record #547329086

$45,000—
Jul 23, 2004

Sold

New England Real Estate Network #3093003

$595,000—
May 31, 2004

Pending

New England Real Estate Network #3093003

—
Feb 7, 2004

Listed (Active)

New England Real Estate Network #3093003

$525,000—
Feb 8, 2003

Listed (Active)

New England Real Estate Network #3082924

$650,000—
DateEvent & SourcePrice
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

07/08/2016

Expired

New England Real Estate Network #3060254

—
11/19/2012

Expired

New England Real Estate Network #4165496

—
06/13/2012

Listed (Active)

New England Real Estate Network #4165496

$745,000
05/23/2012

Expired

New England Real Estate Network #4065251

—
05/23/2011

Listed (Active)

New England Real Estate Network #4065251

$950,000
09/12/2008

Listed (Active)

New England Real Estate Network #3060254

$1,095,000
06/18/2008

Expired

New England Real Estate Network #3042418

—
06/18/2007

Listed (Active)

New England Real Estate Network #3042418

$1,300,000
01/15/2005

Expired

New England Real Estate Network #3082924

—
08/02/2004

Sold (Public Record)

Public Record #547329087

$550,000
08/02/2004

Sold (Public Record)

Public Record #547329086

$45,000
07/23/2004

Sold

New England Real Estate Network #3093003

$595,000
05/31/2004

Pending

New England Real Estate Network #3093003

—
02/07/2004

Listed (Active)

New England Real Estate Network #3093003

$525,000
02/08/2003

Listed (Active)

New England Real Estate Network #3082924

$650,000

For completeness, Compass 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
Home Facts
Beds6Total Finished SqFt4,864 SqFtAbove Grade Finished SqFt4,864 SqFtStories2Lot Size776,675 SqFtStyleSingle Family ResidenceYear Built1963CountyBENNINGTONAPN(180)082062Fireplace TypeHas Fireplace

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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More information about 557 Bennett Hill Road, Shaftsbury, VT 05262

557 Bennett Hill Road is a single family home for sale in Shaftsbury, VT 05262. This property was listed for sale on February 27, 2026 by Mahar McCarthy Real Estate, it's currently listed at $1,495,000. It has been on the market for a total of 26 days and was last sold on July 1, 2022. This listing's school districts are Southwest Vermont Union Elementary School District #87, Mount Anthony Union High School District #14. Nearby schools include Shaftsbury Elementary School, Mt. Anthony Union Middle School and Mt. Anthony Senior Uhsd #14. 557 Bennett Hill Road is a 6-bed, 6-bath, 4,864 sqft single family home built in 1963.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

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 03/25/2026 08:58 PM