423 Main St

Chester, VT 05143

$425,000
Last Sold Price
6
Beds
3,217 Sq. Ft.
$132 / Sq. Ft.
3,217
Sq. Ft.
$132
per Sq. Ft.
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Closed 12/18/25Virtual Tour
Closed 12/18/25Virtual Tour

Description

Absolutely stunning architecture located just steps from the village green and across the road from the historic Congregational Church. This property has five apartments. The kitchen appliances are included in each and there is a shared washer and dryer available for tenant use. Each of the five units has its own 100-amp electric panel box. The heat is a central, oil fired boiler providing baseboard heat with separate thermostats in each unit. Hot water is a central water heater. The building is...Absolutely stunning architecture located just steps from the village green and across the road from the historic Congregational Church. This property has five apartments. The kitchen appliances are included in each and there is a shared washer and dryer available for tenant use. Each of the five units has its own 100-amp electric panel box. The heat is a central, oil fired boiler providing baseboard heat with separate thermostats in each unit. Hot water is a central water heater. The building is handsome with its wrap around porch and columns. There once was a commercial unit in the bottom right side of the house and the individual door and unique windows are still in place. Many historic features are still intact such as hand split lathe, woodwork, flooring, cupboards, hardware and more, but there are some new windows and other updates. There is a very large barn that perhaps has the potential for four additional apartments or storage. Large yard for play or gardens. Ample parking. Easy walk to school, shops, restaurants, and the town recreation area. Bring your ideas....investment rentals, create condos, develop the barn, or what? Easy to show. 24-hour notice needed for one apartment; the others are ready to show.
  1. Listed by Betty McEnaney • Diamond Realty

Sold By Barrett and Valley Associates Inc.

Property Details for 423 Main Street

Zoning
Village Center
LISTING CLOSED: 12/18/2025 12:00 AM

Property Details for 423 Main Street

StatusClosed
MLS #5034061
Days on Market213
Taxes$9,315 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeMulti Family
MLS TypeMulti Family
Year Built1850
Lot Size0.57 AC / 24,829 SF
CountyWindsor County
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Location

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Building Information for 423 Main Street

Stories2Residences5Year Built1850Building Size-Lot Size0.57 AC / 24,829 SF

Payment Calculator

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$2,936 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,160

Property Taxes

$776

HOA Dues

$0

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Property Information for 423 Main Street

Summary
Location and General Information
  • City: Chester
  • County: VT-Windsor
  • Directions: From from the center of the village, travel west on Main Street. The house will be on your left directly opposite the Congregational Church.
  • Latitude: 43.265455499316445
  • Longitude: -72.602734017196653
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Street
  • Zip Code: 05142
Taxes and HOA Information
  • SPAN Number: 144-045-10915
  • Tax Year: 25
  • Tax Year Notes: 2025-26
  • Taxes TBD: No
Parking
  • Garage: No
  • Driveway: Gravel
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Property
Lot Information
  • Lot Features: Landscaped, Level, Open, Sidewalks, Walking Trails, In Town, Near Paths, Near Shopping, Near Public Transportatn, Near School(s)
  • Lot Size Acres: 0.57
  • Road Frontage Length: 70.0
  • Total Finished Area: 3217.0
  • Above Grade Finished Area: 3217.0
  • Above Grade Finished Area Source: Public Records
  • Above Grade Unfinished Area: 375.0
  • AboveGradeUnfinishedAreaSource: Estimated
  • Below Grade Finished Area: 0.0
  • Below Grade Finished Area Source: Public Records
  • Below Grade Unfinished Area: 1485.0
  • BelowGradeUnfinishedAreaSource: Public Records
  • Lot Size Square Feet: 24829.0
  • Total Area: 5077.0
Property and Assessments
  • Current Use: No
  • Property Class: Multi-Family
  • Construction Status: Existing
  • Easements: Yes
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Yes
  • Year Built: 1850
  • 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 Mtn Power
  • Electric: 100 Amp Service, Circuit Breaker(s)
  • Sewer: Public
  • Water Source: Public
  • Utilities: Cable Available, Phone, Telephone Available, Underground Oil Tank
  • Total Gas Meters: 0
  • Total Electric Meters: 5
  • Separate Utilities: Varies
  • Internet: Fiber Optic Internet
Interior and Exterior Features
Exterior Features
  • Color: White
  • Construction Materials: Post and Beam, Clapboard Exterior, Wood Siding
  • Roof: Shingle
  • Total Ranges: 5
Interior Features
  • Appliances: Electric Water Heater, Owned Water Heater
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Dirt Floor, Exterior Access, Exterior Stairs, Full, Interior Access, Interior Stairs, Unfinished
  • Total Full Baths: 5
  • Flooring: Carpet, Combination, Hardwood, Laminate, Softwood, Vinyl, Vinyl Plank
  • Heating: Oil, Baseboard, Multi Zone
  • Cooling: None
  • Total Refrigerators: 5
  • Total Rooms Above Ground: 16
  • Total Stories: 2.5
  • Total Water Heaters: 1
Multi Family
Multi-Family Information
  • Total Units: 5
  • Total 1 BR Units: 4
  • Total 2 BR Units: 1
  • Total 3+ BR Units: 0
  • Total Heat Units: 1
Unit Information
Unit 1
  • Unit 1 Baths: 1
  • Unit 1 Bedrooms: 1
  • Unit 1 Level Number: 1
  • Unit 1 Status: Owner Occupied
  • Unit 1 Rooms: 3
  • Unit 1 Info: Appliances Included, CO Detector, Oil Heat, Heat Included, Hot Water, Microwave, Electric Range, Refrigerator, Smoke Detector, Window Treatments
Unit 2
  • Unit 2 Baths: 1
  • Unit 2 Rooms: 4
  • Unit 2 Status: Vacant
  • Unit 2 Level Number: 1
  • Unit 2 Bedrooms: 2
  • Unit 2 Info: Appliances Included, CO Detector, Electric, Oil Heat, Heat Included, Porch, Electric Range, Refrigerator, Smoke Detector, Window Treatments
Unit 3
  • Unit 3 Baths: 1
  • Unit 3 Rooms: 3
  • Unit 3 Level Number: 2
  • Unit 3 Status: Month to Month
  • Unit 3 Bedrooms: 1
  • Unit 3 Info: Appliances Included, CO Detector, Oil Heat, Heat Included, Electric Range, Refrigerator, Smoke Detector, Window Treatments
Unit 4
  • Unit 4 Level Number: 2
  • Unit 4 Rooms: 3
  • Unit 4 Baths: 1
  • Unit 4 Bedrooms: 1
  • Unit 4 Status: Vacant
  • Unit 4 Info: Appliances Included, CO Detector, Electric, Oil Heat, Heat Included, Electric Range, Refrigerator, Smoke Detector, Window Treatments
Unit 5
  • Unit 5 Level Number: 3
  • Unit 5 Status: Vacant
  • Unit 5 Baths: 1
  • Unit 5 Bedrooms: 1
  • Unit 5 Rooms: 3
  • Unit 5 Info: Appliances Included, CO Detector, Electric, Oil Heat, Heat Included, Electric Range, Refrigerator, Smoke Detector, Window Treatments
Rental
Rent Information
  • Total Leases: 0

Property History for 423 Main Street

DateEvent & SourcePriceAppreciation
Dec 18, 2025

Sold

New England Real Estate Network #5034061

$425,000—
Dec 18, 2025

Pending

New England Real Estate Network #5034061

—
Dec 17, 2025

Sold (Public Record)

Public Record #1923991897

$425,000—
DateEvent & SourcePrice
12/18/2025

Sold

New England Real Estate Network #5034061

$425,000
12/18/2025

Pending

New England Real Estate Network #5034061

—
12/17/2025

Sold (Public Record)

Public Record #1923991897

$425,000

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

Public Records for 423 Main Street

Taxable ValueLand$30,700Additions$289,000Total$319,700
Tax Record2024$8,868 ($739 / month)
Home Facts
Baths4Total Finished SqFt3,217 SqFtAbove Grade Finished SqFt3,217 SqFtStories2Lot Size24,829 SqFtStyleMulti-Family Res (5+ Units)Year Built1850CountyWINDSORAPN(045) 575050

Schools near 423 Main Street

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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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
407 Main Street, Chester, VT 05143
–
5
4
2,047
10,890
397 Main Street, Chester, VT 05143
–
–
–
–
193,406
463 Main Street, Chester, VT 05143
$270,000
5
1,821
10,890
442 Main Street, Chester, VT 05143
$149,000
4
2,264
21,780
14 Church Street, Chester, VT 05143
$290,000
6
4,700
32,670

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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 Diamond 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 08/03/2026 08:17 PM