- beds
- 3
- baths
- 2
- sq ft
- 3,608
- Built
- 1880
145 South Main Street
Chester, VT 05143
Residential Income · Active · MLS #5107814
Listing Courtesy of Nancy Jenkins Real Estate | The Nancy Jenkins Team
The home
About this home
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.
Property information
Details at a glance
Interior3 property facts
- Rooms
- 1
- Heating
- Baseboard, Forced Air, Propane, Oil
- Cooling
- None
Building4 property facts
- Style
- Multi Family
- Year built
- 1880
- Foundation
- Other
- Roof
- Shingle
Land & utilities4 property facts
- Lot size
- 0.8 acres
- Water
- Public
- Sewer
- Public Sewer
- Zoning
- Residential/Commercial
Financial2 property facts
- Annual taxes
- $7,812
- Assessment year
- 2025
Plan your purchase
Estimated monthly cost
Explore costs at the $340,000 asking price. Adjust the assumptions to your situation.
Known monthly costs$2,370 / monthAdjust
- Principal & interest
- $1,719
- Property tax
- $651
- Insurance
- Not entered
- HOA
- Not entered
Listing annual taxes: $7,812. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.
Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.
The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.
Listing history
Price and status timeline
- New
$340,000 · Jun 30, 2026
Compare with confidence
Price & market context
See how this home compares with active listings in Chester.
| Metric | This home | Local listings |
|---|---|---|
| List price | $340,000 | $340,000Near the local benchmark |
| Price / sq ft | $94 | $12525% below local |
| Days on market | 0 | 138100% below local |
Active city listing statistics from PrimeMLS as of September 11, 2026. Asking prices are not completed-sale values.
Keep exploring
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Common questions
About 145 South Main Street
Can I request a private showing?
Request a tour of 145 South Main Street and a Bean Group agent will help coordinate an available time with the listing side.
Can you help me evaluate this property?
Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
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