145 South Main Street

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Active
$340,000
3 beds2 baths3,608 sqft$94/sqft
145 S Main St, Chester, VT 05143
Est: $2,408/moGet pre-approved
Multi FamilyProperty Type
0.8 acresLot Size
1880Year Built
$94/sq ftPrice per sq ft

Description

Exceptional mixed-use opportunity with strong visibility on South Main Street in downtown Chester. This versatile property features two residentialapartments—a 2-bedroom, 1-bath unit and a 1-bedroom, 1-bath unit—alongside two commercial spaces, creating a diverse and stable income stream. A large barn addstremendous upside with the potential for additional units or expanded uses, subject to local approvals. Positioned in the heart of one of Southern Vermont’s mostcharming villages, the property benefits...Exceptional mixed-use opportunity with strong visibility on South Main Street in downtown Chester. This versatile property features two residentialapartments—a 2-bedroom, 1-bath unit and a 1-bedroom, 1-bath unit—alongside two commercial spaces, creating a diverse and stable income stream. A large barn addstremendous upside with the potential for additional units or expanded uses, subject to local approvals. Positioned in the heart of one of Southern Vermont’s mostcharming villages, the property benefits from excellent exposure and convenient access to Chester’s vibrant downtown, local shops, restaurants, and year-round events. Ample parking provides added convenience for residents, customers, and tenants alike. Whether you're looking to expand your portfolio, establish a business presence, orcapitalize on future development potential, this well-located property offers the ideal blend of cash flow, visibility, and long-term opportunity. 3D Virtual Tour availableupon request.
12 days on Market
  • Listed by: The Nancy Jenkins Team • Nancy Jenkins Real Estate
Last updated: 09/02/2026 02:21 PM • Source: New England Real Estate Network, MLS#: 5107814

Location

Listing Courtesy of Nancy Jenkins Real Estate
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$2,408 per month

30 year fixed, 6.71% Interest

Principal and Interest

$1,757

Property Taxes

$651

HOA Dues

$0

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Property Information for 145 South Main Street

Property Details
  • Taxes: $7,812 / year
  • MLS Type: Multi Family
  • County: Windsor County
  • Zoning: Residential/Commercial
Building Information
  • Stories: 2
  • Residences: 5
  • Year Built: 1880
  • Lot Size: 0.80 AC / 34,848 SF
Summary
Location and General Information
  • City: Chester
  • County: VT-Windsor
  • Latitude: 43.261796495559793
  • Longitude: -72.592647457672115
  • Road Frontage: TBD
  • Seasonal: No
  • State: VT
  • Street Designation: Street
  • Zip Code: 05143
Taxes and HOA Information
  • SPAN Number: 144-045-11660
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: No
  • Driveway: Paved
Property
Lot Information
  • Lot Features: In Town
  • Lot Size Acres: 0.8
  • Total Finished Area: 3608.0
  • Above Grade Finished Area: 3608.0
  • Above Grade Finished Area Source: Assessor
  • Above Grade Unfinished Area: 0.0
  • Below Grade Finished Area: 0.0
  • Below Grade Unfinished Area: 1096.0
  • BelowGradeUnfinishedAreaSource: Assessor
  • Lot Size Square Feet: 34848.0
  • Total Area: 4704.0
Property and Assessments
  • Property Class: Multi-Family
  • Property Condition: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: No
  • Year Built: 1880
Utilities
  • Fuel Company: Irving Energy
  • Electric: Circuit Breaker(s)
  • Sewer: Public
  • Water Source: Public
  • Utilities: Cable Available
  • Internet: High Speed Intrnt Avail
Interior and Exterior Features
Exterior Features
  • Construction Materials: Wood Frame
  • Roof: Shingle
Interior Features
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Unfinished
  • Heating: Propane, Oil, Baseboard, Hot Air
  • Cooling: None
  • Total Stories: 2.5
Multi Family
Income & Expenses Information
  • Gross Income: $54,540.00
  • Net Income: $30,730.00
  • Operating Expense Incl: Insurance, Maintenance, Snow Removal, Water/Sewer
  • Operating Expense: $23,810
Multi-Family Information
  • Total Units: 5
  • Total 1 BR Units: 4
  • Total 2 BR Units: 1
  • Total 3+ BR Units: 0
Unit Information
Unit 1
  • Unit 1 Baths: 1
  • Unit 1 Bedrooms: 2
  • Unit 1 Lease Term: Annual
  • Unit 1 Rental Amt Freq: Monthly
  • Unit 1 Status: Leased
  • Unit 1 Rental Amount: $1,400.00
Unit 2
  • Unit 2 Lease Term: Annual
  • Unit 2 Status: Leased
  • Unit 2 Rental Amt Freq: Monthly
  • Unit 2 Rental Amount: $880.00
Unit 3
  • Unit 3 Lease Term: Annual
  • Unit 3 Baths: 1
  • Unit 3 Rental Amt Freq: Monthly
  • Unit 3 Status: Leased
  • Unit 3 Bedrooms: 1
  • Unit 3 Rental Amount: $1,200.00
Unit 4
  • Unit 4 Lease Term: Annual
  • Unit 4 Rental Amt Freq: Monthly
  • Unit 4 Status: Leased
  • Unit 4 Rental Amount: $875.00
Unit 5
  • Unit 5 Rental Agreement: Yes
  • Unit 5 Rental Amt Freq: Monthly
  • Unit 5 Status: Leased
  • Unit 5 Lease Term: Annual
  • Unit 5 Rental Amount: $180.00

Property History for 145 South Main Street

DateEvent & SourcePriceAppreciation
Sep 2, 2026

Listed (Active)

New England Real Estate Network #5107814

$340,000—
Nov 10, 2020

Sold (Public Record)

Public Record #682602315

$240,000—
DateEvent & SourcePrice
09/02/2026

Listed (Active)

New England Real Estate Network #5107814

$340,000
11/10/2020

Sold (Public Record)

Public Record #682602315

$240,000

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

Public Records for 145 South Main Street

Taxable ValueLand$33,000Additions$235,100Total$268,100
Tax Record2025$5,004 ($417 / month)
Home Facts
Baths2.5Total Finished SqFt3,608 SqFtAbove Grade Finished SqFt3,608 SqFtUnfinished Basement SqFt1,096 SqFtLot Size34,848 SqFtStyleMiscellaneous CommercialYear Built1880Year Renovated1880CountyWINDSORAPN(045) 605142

Schools near 145 South 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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More information about 145 South Main Street, Chester, VT 05143

145 South Main Street is a multi-family home for sale in Chester, VT 05143. This property was listed for sale on September 2, 2026 by Nancy Jenkins Real Estate, it's currently listed at $340,000. It has been on the market for a total of 12 days and was last sold on November 10, 2020. This listing's school district is Green Mountain Unified School District. Nearby schools include Chester-Andover Usd #29 and Green Mountain Uhsd #35. 145 South Main Street is a 3-bed, 2-bath, 3,608 sqft multi-family home built in 1880.

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 Nancy Jenkins Real Estate

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 09/14/2026 06:19 PM