145 South Main Street Chester, VT $ 385,000
145 South Main Street
$ 385,000
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145 South Main Street

Chester, VT, 05143
$ 385,000
Bedrooms-- Baths-- Sq 3,608

Monthly Estimate*

$ 2,431

Listed by The Nancy Jenkins Team, Nancy Jenkins Real Estate, kelsey@nancyjenkins.com
145 South Main Street, Chester, VT 05143 - Image 1
145 South Main Street, Chester, VT 05143 - Image 2
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145 South Main Street, Chester, VT 05143 - Image 9
145 South Main Street, Chester, VT 05143 - Image 10

Commercial Property for sale in Chester, VT

for $385,000. This 3,608 square foot building was built in 1880 on a lot size of 0.8.

Exceptional mixed-use opportunity with strong visibility on South Main Street in downtown Chester. Offered at an attractive 8% cap rate, this versatile property features two residential apartments—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 adds tremendous upside with the potential for additional units or expanded uses, subject to local approvals. Positioned in the heart of one of Southern Vermont’s most charming 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, or capitalize on future development potential, this well-located property offers the ideal blend of cash flow, visibility, and long-term opportunity. 3D Virtual Tour available upon request.

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Commercial Active

Price

$ 385,000

Property Type

Commercial

Taxes

$ 0

Style

Business,Multi-Family,Office,Retail

Lot Size

0.8

Year Built

1880

Town/City

Chester

County/Region

Windsor

MLS | Web ID

5097411

Features
Interior
Basement Description Unfinished
Basement Yes
Total Number of Units 5
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General
Road Frontage TBD
Sewer Public
Heating Baseboard Hot Air Propane Oil
Utilities Cable Available
Roof Slate
Zoning Commercial
Year Built 1880
Electric Circuit Breaker(s)
Business Type Business Multi-Family Office Retail
Net Income 30610
Tax Year 2025
Gross Income 54420
Status Detail 0
Covenants Unknown
Construction Materials Wood Frame
City Chester
DOM 0
Price Per Sq Ft Total AG 106.71
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Exterior
Lot Features In Town
Lot Size Area 0.8
Water Source Public
Parking Features Off Street
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* Excluded Features
List By
The Nancy Jenkins Team

Listing Agent

Nancy Jenkins Real Estate

Broker

kelsey@nancyjenkins.com

Email

Affordability Calculator

$2,431
Per Month
100%
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0%
Monthly Principal & Interest
$2,431
Monthly Property Taxes
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Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
451920 Elementary School
452237 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
6/30/2026$385,000 Listed Price

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145 South Main Street, Chester, VT, 05143 is a Commercial Property for sale at $385,000 with 3,608 sqft and a lot size of 0.8. 145 South Main Street was built in 1880. The property's zip code is 05143 which is in Chester, VT