About this home
Rich in architectural character and timeless appeal, this spacious two-family residence offers a rare combination of historic charm, generous living space, and versatility. Maintained within the same ownership for decades, the property reflects years of history and offers an opportunity to preserve its original character while introducing modern updates. Beautiful wide-plank pine flooring and traditional details add warmth and distinction throughout. The first unit features multiple bedrooms, a full bath, and additional upper-level space with two rooms and a half bath. The second unit offers two bedrooms, an exceptionally spacious living room, a generously sized kitchen with pantry, and a full bath. Additional features include a substantial, well-maintained basement, attic designated for storage only, a garage, off-street parking, a manageable yard, and an inviting porch. While the property would benefit from updating, its spacious layout, distinctive craftsmanship, and two-unit configuration present a variety of possibilities, including owner occupancy, rental income, or multigenerational use. A property with a meaningful past and exceptional potential for its next chapter.
Listing last checked: Listing updated:
Listed by Mandy Fontanez · Coldwell Banker Realty - Worcester · MLS #73590382
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Details at a glance
Interior5 property facts
- Rooms
- 14
- Heating
- Natural Gas
- Cooling
- None
- Flooring
- Wood, Tile, Laminate, Hardwood
- Basement
- Yes · Full
Building6 property facts
- Style
- Multi Family
- Year built
- 1925
- Garage
- 1
- Parking
- 6
- Foundation
- Stone
- Roof
- Shingle
Land & utilities5 property facts
- Lot size
- 0.21 acres
- Water
- Public
- Sewer
- Public Sewer
- Pool
- Not reported
- Zoning
- R2
Financial2 property facts
- Annual taxes
- $5,481
- Assessment year
- 2026
Location
Estimated monthly cost
Explore costs at the $459,000 asking price. Adjust the assumptions to your situation.
Known monthly costs$2,778 / monthAdjust
- Principal & interest
- $2,321
- Property tax
- $457
- Insurance
- Not entered
- HOA
- Not entered
Listing annual taxes: $5,481. 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.
More property insights
Automated value estimate $458,287
Estimated range $444,120–$472,453.
Automated estimates are not appraisals or guarantees of market value.
Request a professional market analysisPhoto-based condition insights
Overall presentation: average
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About 106 Chestnut St
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