258 Chester Hill Rd

Grafton, VT 05146

$734,000
Price
3
Beds
4,285 Sq. Ft.
$171 / Sq. Ft.
4,285
Sq. Ft.
$171
per Sq. Ft.
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Description

Set on a beautifully landscaped parcel just minutes from the heart of historic Grafton, this meticulously maintained residence offers timeless New England charm, exceptional craftsmanship, and inviting spaces. Surrounded by mature trees, perennial gardens, and lush lawns, the property provides a peaceful setting with the perfect balance of privacy and convenience. Inside, warm hardwood floors, abundant natural light, and classic architectural details create a welcoming atmosphere. The spacious living...Set on a beautifully landscaped parcel just minutes from the heart of historic Grafton, this meticulously maintained residence offers timeless New England charm, exceptional craftsmanship, and inviting spaces. Surrounded by mature trees, perennial gardens, and lush lawns, the property provides a peaceful setting with the perfect balance of privacy and convenience. Inside, warm hardwood floors, abundant natural light, and classic architectural details create a welcoming atmosphere. The spacious living room is anchored by a wood-burning fireplace, creating a warm and inviting gathering space for family and friends. Just beyond, the library/den offers a quiet retreat to unwind with a favorite book in front of the home's second wood-burning fireplace, making it one of the home's most inviting spaces. The kitchen blends timeless character with everyday functionality. Rich cabinetry, generous workspace and a spacious walk-in pantry that provides abundant storage along with additional prep space ideal for entertaining. The screened porch offers a peaceful place to enjoy morning coffee, summer dinners, or a quiet afternoon while overlooking the beautifully landscaped grounds. Protected from the elements yet open to the fresh Vermont air, it becomes a favorite gathering place throughout the warmer months. Each bedroom features its own private en-suite bath, providing exceptional comfort and privacy for family and guests. The primary suite serves as a relaxing retreat with hardwood floors, abundant natural light, and a well-appointed bath. Outside, perennial gardens frame the home with colorful blooms throughout the growing season, complementing the stone walkways and classic Vermont landscaping. An attached two-car garage provides convenience and additional storage. Located just minutes from the charming village of Grafton, you'll enjoy one of Vermont's most treasured communities.
  1. Listed by Betsy Wadsworth • Four Seasons Sotheby's Int'l Realty

Property Details for 258 Chester Hill Road

Zoning
Village
LISTING UPDATED: 06/27/2026 03:04 PM

Property Details for 258 Chester Hill Road

StatusActive
MLS #5097081
Days on Market1
Taxes$14,784 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1952
Lot Size3.50 AC / 152,460 SF
CountyWindham County
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Location

Listing Courtesy of Four Seasons Sotheby's Int'l Realty
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Building Information for 258 Chester Hill Road

Stories2Year Built1952Building Size-Lot Size3.50 AC / 152,460 SF

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$4,890 per month

30 year fixed, 6.36% Interest

Principal and Interest

$3,658

Property Taxes

$1,232

HOA Dues

$0

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Property Information for 258 Chester Hill Road

Summary
Location and General Information
  • City: Grafton
  • County: VT-Windham
  • Directions: From Chester Village, take Chester Road and follow for 6.9 miles. Driveway on your left.
  • Latitude: 43.174683000001004
  • Longitude: -72.603853000000001
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05146
Taxes and HOA Information
  • SPAN Number: 249-079-10539
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 3.00
  • Driveway: Paved
Property
Lot Information
  • Lot Features: Country Setting, Landscaped, Level, Open, Sloping, Stream, Wooded, Near Shopping, Rural
  • Lot Size Acres: 3.5
  • Road Frontage Length: 366.0
  • Total Finished Area: 4285.0
  • Above Grade Finished Area: 4285.0
  • Above Grade Finished Area Source: Public Records
  • Above Grade Unfinished Area: 0.0
  • AboveGradeUnfinishedAreaSource: Public Records
  • Below Grade Finished Area: 0.0
  • Below Grade Finished Area Source: Public Records
  • Below Grade Unfinished Area: 1800.0
  • BelowGradeUnfinishedAreaSource: Public Records
  • Lot Size Square Feet: 152460.0
  • Total Area: 6085.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 1952
  • School District: Athens/Grafton School District
  • Elementary School: Grafton Elementary School
Utilities
  • Electric: 200+ Amp Service, Generator
  • Sewer: 1000 Gallon, Conventional Leach Field
  • Water Source: Drilled Well
  • Utilities: Propane, Telephone at Site
  • Internet: High Speed Intrnt at Site, Fiber Optic Internet
Interior and Exterior Features
Exterior Features
  • Color: Grey
  • Construction Materials: Wood Frame, Shake Siding
  • Roof: Asphalt Shingle
Interior Features
  • Appliances: Down Draft Cooktop, Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Oil Water Heater, Wine Cooler
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Full, Interior Access, Exterior Access
  • Rooms: Level 1: Level 1: 1/2 Bathroom, Level 1: Dining Room, Level 1: Foyer, Level 1: Kitchen, Level 1: Library, Level 1: Living Room, Level 1: Mudroom, Level 1: Office/Study, Level 1: Sunroom
  • Rooms: Level 2: Level 2: Primary Bdm Ste
  • Flooring: Ceramic Tile, Hardwood, Wood
  • Heating: Oil, Baseboard, Hot Water
  • Cooling: Central AC
  • Total Stories: 2
  • Rooms Total: 13
  • Bathrooms Full: 2
  • Bathrooms Half: 2
  • Bathrooms One Quarter: 0
  • Bathrooms Three Quarter: 1
  • Bedrooms Total: 3
  • Bathrooms Total: 5
Room Information
Room 1
  • Room Level: 1
  • Room Type: Foyer
Room 2
  • Room Level: 1
  • Room Type: Living Room
Room 3
  • Room Level: 1
  • Room Type: Sunroom
Room 4
  • Room Level: 1
  • Room Type: Library
Room 5
  • Room Level: 1
  • Room Type: Dining Room
Room 6
  • Room Level: 1
  • Room Type: Kitchen
Room 7
  • Room Level: 1
  • Room Type: Mudroom
Room 8
  • Room Level: 1
  • Room Type: Bathroom Half
Room 9
  • Room Level: 1
  • Room Type: Office/Study
Room 10
  • Room Level: 2
  • Room Type: Bedroom with Bath
Room 11
  • Room Level: 2
  • Room Type: Primary BR Suite
Room 12
  • Room Level: 2
  • Room Type: Bedroom with Bath

Property History for 258 Chester Hill Road

DateEvent & SourcePriceAppreciation
Jun 27, 2026

Listed (Active)

New England Real Estate Network #5097081

$734,000—
May 25, 2021

Listed (Active)

New England Real Estate Network #4863008

$825,000—
DateEvent & SourcePrice
06/27/2026

Listed (Active)

New England Real Estate Network #5097081

$734,000
05/25/2021

Listed (Active)

New England Real Estate Network #4863008

$825,000

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

Public Records for 258 Chester Hill Road

Taxable ValueLand$101,100Additions$511,800Total$612,900
Tax Record2019$14,033 ($1,169 / month)
Home Facts
Beds3Baths3.5Total Finished SqFt4,285 SqFtAbove Grade Finished SqFt4,285 SqFtStories2Lot Size152,460 SqFtStyleSingle Family ResidenceYear Built1952CountyWINDHAMAPN(079) 008083Fireplace TypeHas Fireplace

Schools near 258 Chester Hill Road

This home is within Windham Northeast Union Elementary School District #95.
Rating
School
Type
Grades
Distance
Grafton Elementary School
Public - PK to 8
Bellows Falls Uhsd #27
Public - 9 to 12
Rating
School
Distance
Grafton Elementary School
PublicPK to 8

Bellows Falls Uhsd #27
Public9 to 12

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 258 Chester Hill Road, Grafton, VT 05146

258 Chester Hill Road is a single family home for sale in Grafton, VT 05146. This listing's school districts are Bellows Falls Union High School District #27, Windham Northeast Union Elementary School District #95. Nearby schools include Grafton Elementary School and Bellows Falls Uhsd #27. 258 Chester Hill Road is a 3-bed, 5-bath, 4,285 sqft single family home built in 1952.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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 Four Seasons Sotheby's Int'l Realty

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 06/28/2026 01:38 AM