423 Main Street

Closed 12/18/25Virtual Tour

Sold

Last Sold Price

$425,000

6 beds5 baths3,217 sqft$132/sqft

423 Main St, Chester, VT 05143

Multi FamilyProperty Type

0.57 acresLot Size

1850Year Built

$132/sq ftPrice per sq ft

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.

Sold By Barrett and Valley Associates Inc.

Listed by: Betty McEnaney • Diamond Realty

Listing closed: 12/18/2025 12:00 AM • Source: New England Real Estate Network, MLS#: 5034061

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$2,936 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,160

Property Taxes

$776

HOA Dues

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Property Information for 423 Main Street

Property Details

Taxes: $9,315 / year
MLS Type: Multi Family
County: Windsor County
Zoning: Village Center

Building Information

Stories: 2
Residences: 5
Year Built: 1850
Lot Size: 0.57 AC / 24,829 SF

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

Virtual Tour

Property Panorama Virtual Tour: https://tour.neren.com/423-Main-Street-Chester-VT-05142/unbranded

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

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

Date	Event & Source	Price	Appreciation
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	—
Oct 29, 2025	Active Under Contract New England Real Estate Network #5034061		—
May 29, 2025	Price Change New England Real Estate Network #5034061	$575,000	—
Mar 30, 2025	Listed (Active) New England Real Estate Network #5034061	$605,000	—

Date	Event & Source	Price
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
10/29/2025	Active Under Contract New England Real Estate Network #5034061	—
05/29/2025	Price Change New England Real Estate Network #5034061	$575,000
03/30/2025	Listed (Active) New England Real Estate Network #5034061	$605,000

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 Record2025$5,967 ($497 / month)

Home Facts

Baths4Total Finished SqFt3,217 SqFtAbove Grade Finished SqFt3,217 SqFtUnfinished Basement SqFt1,485 SqFtStories2Lot Size24,829 SqFtStyleMulti-Family Res (5+ Units)Year Built1850Year Renovated1850CountyWINDSORAPN(045) 575050

Schools near 423 Main Street

This home is within Green Mountain Unified School District.


Rating	School	Type	Grades	Distance
6/10	Chester-Andover Usd #29	Public - Serves this home	PK to 6	0.4 mi
7/10	Green Mountain Uhsd #35	Public - Serves this home	7 to 12	1.4 mi


Rating	School	Distance
6/10	Chester-Andover Usd #29 PublicPK to 6 Serves this home	0.4 mi
7/10	Green Mountain Uhsd #35 Public7 to 12 Serves this home	1.4 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.

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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 09/01/2026 05:25 PM

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