258 Chester Hill Road

Active Under ContractVirtual Tour

Contract Out

$734,000

3 beds5 baths4,285 sqft$171/sqft

258 Chester Hill Rd, Grafton, VT 05146

Est: $4,740/moGet pre-approved

Single FamilyProperty Type

3.5 acresLot Size

1952Year Built

$171/sq ftPrice per sq ft

3 carsParking Spaces

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.

47 days on Market

Listed by: Betsy Wadsworth • Four Seasons Sotheby's Int'l Realty
Listed by: Mike Masters • Four Seasons Sotheby's Int'l Realty

Last updated: 08/13/2026 10:47 PM • Source: New England Real Estate Network, MLS#: 5097081

Location

Homepage
VT
Windham County
Grafton
05146
258 Chester Hill Rd

Listing Courtesy of Four Seasons Sotheby's Int'l Realty

Add your commute

Virtual Tour

Payment Calculator

Get preapproved with Rocket Mortgage¹

$4,740 per month

30 year fixed, 6.55% Interest

Principal and Interest

$3,731

Property Taxes

$1,009

HOA Dues

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Property Information for 258 Chester Hill Road

Property Details

Taxes: $12,108 / year
MLS Type: Residential / Single Family
County: Windham County
Zoning: Village

Building Information

Stories: 2
Year Built: 1952
Lot Size: 3.50 AC / 152,460 SF

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: 2026

Taxes TBD: No

Parking

Garage: Yes
Garage Capacity: 3.00

Driveway: Paved

Virtual Tour

Property Panorama Virtual Tour: https://tour.primemls.com/258-Chester-Rd-Road-Grafton-VT-05146/unbranded

Property

Lot Information

Lot Features: Country Setting, Landscaped, Level, Open, Sloping, Wooded, Near Shopping, Rural
Lot Size Acres: 3.5

Road Frontage Length: 366.0
Water Body Access: No
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

Property Condition: 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: Fiber Optic Internet, High Speed Intrnt at Site

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: Exterior Access, Full, Interior 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

Date	Event & Source	Price	Appreciation
Aug 13, 2026	Active Under Contract New England Real Estate Network #5097081		—
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	—

Date	Event & Source	Price
08/13/2026	Active Under Contract New England Real Estate Network #5097081	—
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 Record2025$9,315 ($776 / month)

Home Facts

Beds3Baths3.5Total Finished SqFt4,285 SqFtAbove Grade Finished SqFt4,285 SqFtStories2Lot Size152,460 SqFtStyleSingle Family ResidenceYear Built1952Year Renovated1952CountyWINDHAMAPN(079) 008083

Schools near 258 Chester Hill Road

This home is within Windham Northeast Union Elementary School District #95.


Rating	School	Type	Grades	Distance
NR	Grafton Elementary School	Public - Serves this home	PK to 8	0.4 mi
5/10	Bellows Falls Uhsd #27	Public - Serves this home	9 to 12	9.0 mi


Rating	School	Distance
NR	Grafton Elementary School PublicPK to 8 Serves this home	0.4 mi
5/10	Bellows Falls Uhsd #27 Public9 to 12 Serves this home	9.0 mi

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.

Similar Homes

Explore Nearby Homes

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.

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 08/29/2026 03:25 PM

Know your buying power with a preapproval and custom rate in minutes

Explore Nearby Homes

Homes in Nearby Grafton Neighborhoods

Homes in Nearby Grafton Cities

Homes in Nearby Grafton Zip Codes