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For Sale

106 Chestnut St, Southbridge MA 01550

Southbridge, MA 01550

$459K
6 BD · 3 BA · 2,872 sf · 0.21 ac · Built 1925
The residence

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.

At a glance
Property type
Multi Family
Status
Active
Year built
1925
Lot size
0.21 acres
Living area
2,872 sf
MLS#
ac239b3e5366de29d967d3ca51a5ec97
Beds · Baths
6 · 3
Location

Southbridge, MA.

Southbridge, Massachusetts, is a market our advisors follow closely — its streets, housing stock and setting each shape what a residence here is worth and how it lives day to day. We are glad to walk you through the locale in detail, and how this particular address sits within it.

Estimated Monthly Payment+
$2K/mo
Approximate · principal & interest only
Display Currency
$459K

Indicative conversion — settlement always in USD.

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Listing courtesy of Coldwell Banker Realty - Worcester · MLSPIN

MLS Property Information Network.The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

Listings updated Oct 18, 2026

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