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Bean Group
Offered at $459,000Active
beds
6
baths
3
sq ft
2,872
Built
1925

106 Chestnut St

Southbridge, MA 01550

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.

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Photo-based condition insights

Overall presentation: average

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About 106 Chestnut St

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Request a tour of 106 Chestnut St 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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