3466 Highway 103

Chester, VT 05143

$399,000
Price
2
Beds
2,751 Sq. Ft.
$145 / Sq. Ft.
2,751
Sq. Ft.
$145
per Sq. Ft.
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Under ContractVirtual Tour
Under ContractVirtual Tour

Description

Set on .76 acres in the peaceful Chester VT countryside, this former schoolhouse offers timeless farmhouse charm, rich history, and a setting that feels both private and inviting. Framed by classic stone walls, a pond site, and a gently wooded backdrop, the home sits just off a main road, providing easy access to town while maintaining a quiet, pastoral atmosphere. Originally serving the community as a schoolhouse until the early 1960s, the property was thoughtfully converted into a residence that...Set on .76 acres in the peaceful Chester VT countryside, this former schoolhouse offers timeless farmhouse charm, rich history, and a setting that feels both private and inviting. Framed by classic stone walls, a pond site, and a gently wooded backdrop, the home sits just off a main road, providing easy access to town while maintaining a quiet, pastoral atmosphere. Originally serving the community as a schoolhouse until the early 1960s, the property was thoughtfully converted into a residence that honors its roots while offering comfortable modern living. The original schoolroom now anchors the home as a warm, open living space filled with natural light, where hardwood floors and tall windows create an airy yet cozy environment ideal for everyday living and gathering. The farmhouse-style kitchen flows seamlessly into the living area and features butcher block countertops, a professional-grade gas convection range with double ovens, and a breakfast bar with a charming pass-through window, perfect for casual meals and entertaining. A spiral staircase adds rustic character and leads to the upper level, offering a spacious bedroom or studio and flexible use for guests, creative space, or a private retreat. The primary suite serves as a peaceful sanctuary with vaulted ceilings, custom built-in shelving, a private full bath, and a cozy wood stove. Doors open to a rear deck overlooking the private yard and surrounding countryside. Additional features include a generous first-floor laundry area, enclosed sun porch, outdoor patio, a private hot tub with a heated walkway for truly maintenance-free winter access (no shoveling, ever!) and an attached two-car garage currently used as a game room, easily adapted back to garage space or reimagined as a workshop, studio, or home office. With commercial zoning, just 10 minutes from Okemo Mountain Resort, and a history as a successful Airbnb, this rare property offers character, flexibility, income potential, and true country charm.
  1. Listed by Betsy Adamovich • Real Broker LLC

Property Details for 3466 Highway 103

Zoning
Residential Commercial
LISTING UPDATED: 02/16/2026 03:45 PM

Property Details for 3466 Highway 103

StatusUnder Contract
MLS #5074728
Days on Market25
Taxes$5,909 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1874
Lot Size0.76 AC / 33,105 SF
CountyWindsor County
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Location

Listing Courtesy of Real Broker LLC
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Building Information for 3466 Highway 103

Stories1Year Built1874Building Size-Lot Size0.76 AC / 33,105 SF

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$2,502 per month

30 year fixed, 6.46% Interest

Principal and Interest

$2,009

Property Taxes

$492

HOA Dues

$0

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Property Information for 3466 Highway 103

Summary
Location and General Information
  • City: Chester
  • County: VT-Windsor
  • Latitude: 43.325426000000000
  • Longitude: -72.607392186508207
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Zip Code: 05143
Taxes and HOA Information
  • SPAN Number: 144-045-11230
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Paved
Property
Lot Information
  • Lot Features: Country Setting, Level, Pond
  • Lot Size Acres: 0.76
  • Road Frontage Length: 230.0
  • Water Body Access: No
  • Total Finished Area: 2751.0
  • Above Grade Finished Area: 2751.0
  • Above Grade Finished Area Source: Estimated
  • Above Grade Unfinished Area: 0.0
  • AboveGradeUnfinishedAreaSource: Estimated
  • Below Grade Finished Area: 0.0
  • Below Grade Unfinished Area: 810.0
  • BelowGradeUnfinishedAreaSource: Public Records
  • Lot Size Square Feet: 33106.0
  • Total Area: 3561.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Suitable Use: Commercial, Mixed Use, Residential
  • Surveyed: Unknown
  • Year Built: 1874
  • School District: Two Rivers Supervisory Union
  • High School: Green Mountain UHSD #35
  • Middle/Jr School: Green Mountain UHSD #35
  • Elementary School: Chester-Andover Elementary
Utilities
  • Electric Company: Green Mountain Power
  • Cable Company: Xfinity
  • Fuel Company: Bart Energy, Suburban Pro
  • Electric: Circuit Breaker(s)
  • Sewer: Private, Septic
  • Water Source: Drilled Well, Private
  • Utilities: Cable Available, Propane, Telephone Available
  • Internet: Fiber Optic Internt Avail
  • Water Company: N/A
Interior and Exterior Features
Exterior Features
  • Construction Materials: Wood Frame, Clapboard Exterior
  • Roof: Metal, Slate
Interior Features
  • Appliances: Gas Cooktop, Dryer, Freezer, Microwave, Refrigerator, Washer, Gas Stove
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Gravel, Sump Pump, Unfinished, Interior Access
  • Rooms: Level 1: Level 1: Bedroom, Level 1: Full Bathroom, Level 1: Dining Room, Level 1: Kitchen, Level 1: Living Room, Level 1: Other, Level 1: Sunroom
  • Rooms: Level 2: Level 2: Bedroom, Level 2: Primary Bedroom, Level 2: Primary Bdm Ste
  • Flooring: Carpet, Hardwood, Laminate, Vinyl
  • Heating: Propane, Oil, Baseboard, Hot Air, Hot Water
  • Cooling: None
  • Total Stories: 1.5
  • Rooms Total: 6
  • Bathrooms Full: 2
  • Bathrooms Half: 0
  • Bathrooms One Quarter: 0
  • Bathrooms Three Quarter: 0
  • Bedrooms Total: 2
  • Bathrooms Total: 2
Room Information
Room 1
  • Room Dimensions: 20.5x16.7
  • Room Level: 1
  • Room Type: Living Room
Room 2
  • Room Dimensions: 29.9x10.5
  • Room Level: 1
  • Room Type: Dining Room
Room 3
  • Room Dimensions: 8.11x14.3
  • Room Level: 1
  • Room Type: Kitchen
Room 4
  • Room Dimensions: 17.10x9.6
  • Room Level: 1
  • Room Type: Bedroom
Room 5
  • Room Dimensions: 8.8x8.8
  • Room Level: 1
  • Room Type: Bathroom Full
Room 6
  • Room Dimensions: 23.10x7.5
  • Room Level: 1
  • Room Type: Sunroom
Room 7
  • Room Dimensions: 23.10x24
  • Room Level: 1
  • Room Type: Other
Room 8
  • Room Dimensions: 17.7x9.10
  • Room Level: 2
  • Room Type: Primary BR Suite
Room 9
  • Room Dimensions: 23.10x24
  • Room Level: 2
  • Room Type: Primary Bedroom
Room 10
  • Room Dimensions: 29.9x18.11
  • Room Level: 2
  • Room Type: Bedroom

Property History for 3466 Highway 103

DateEvent & SourcePriceAppreciation
Feb 16, 2026

Active Under Contract

New England Real Estate Network #5074728

—
Jan 22, 2026

Listed (Active)

New England Real Estate Network #5074728

$399,000—
Oct 27, 2020

Sold (Public Record)

Public Record #681404906

$195,000—
Oct 23, 2020

Sold

New England Real Estate Network #4808612

$195,000—
Oct 20, 2020

Pending

New England Real Estate Network #4808612

—
Jun 1, 2020

Price Change

New England Real Estate Network #4808612

$209,000—
Jun 1, 2020

Listed (Active)

New England Real Estate Network #4808612

$199,000—
Apr 15, 2014

Expired

New England Real Estate Network #4237303

—
May 13, 2013

Listed (Active)

New England Real Estate Network #4237303

$199,000—
May 1, 2013

Expired

New England Real Estate Network #4194783

—
Oct 25, 2012

Listed (Active)

New England Real Estate Network #4194783

$229,000—
Mar 31, 2012

Expired

New England Real Estate Network #4057631

—
Apr 20, 2011

Listed (Active)

New England Real Estate Network #4057631

$229,000—
Sep 10, 2001

Sold

New England Real Estate Network #3006161

$132,000—
Jul 1, 2001

Pending

New England Real Estate Network #3006161

—
Jan 22, 2001

Listed (Active)

New England Real Estate Network #3006161

$135,000—
DateEvent & SourcePrice
02/16/2026

Active Under Contract

New England Real Estate Network #5074728

—
01/22/2026

Listed (Active)

New England Real Estate Network #5074728

$399,000
10/27/2020

Sold (Public Record)

Public Record #681404906

$195,000
10/23/2020

Sold

New England Real Estate Network #4808612

$195,000
10/20/2020

Pending

New England Real Estate Network #4808612

—
06/01/2020

Price Change

New England Real Estate Network #4808612

$209,000
06/01/2020

Listed (Active)

New England Real Estate Network #4808612

$199,000
04/15/2014

Expired

New England Real Estate Network #4237303

—
05/13/2013

Listed (Active)

New England Real Estate Network #4237303

$199,000
05/01/2013

Expired

New England Real Estate Network #4194783

—
10/25/2012

Listed (Active)

New England Real Estate Network #4194783

$229,000
03/31/2012

Expired

New England Real Estate Network #4057631

—
04/20/2011

Listed (Active)

New England Real Estate Network #4057631

$229,000
09/10/2001

Sold

New England Real Estate Network #3006161

$132,000
07/01/2001

Pending

New England Real Estate Network #3006161

—
01/22/2001

Listed (Active)

New England Real Estate Network #3006161

$135,000

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

Public Records for 3466 Highway 103

Taxable ValueLand$26,100Additions$176,700Total$202,800
Tax Record2024$5,626 ($469 / month)
Home Facts
Beds2Baths2Total Finished SqFt1,652 SqFtAbove Grade Finished SqFt1,652 SqFtStories2Lot Size33,106 SqFtStyleSingle Family ResidenceYear Built1874CountyWINDSORAPN(045) 505009

Schools near 3466 Highway 103

This home is within Green Mountain Unified School District.
Rating
School
Type
Grades
Distance
Chester-Andover Usd #29
Public - PK to 6
Green Mountain Uhsd #35
Public - 7 to 12
Rating
School
Distance
Chester-Andover Usd #29
PublicPK to 6

Green Mountain Uhsd #35
Public7 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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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 Real Broker LLC

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 04/18/2026 07:08 PM