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6 Beds
3 Baths
2,872 sqft

$459,000

106 Chestnut St, Southbridge MA, 01550

Price per sqft$159.82
Built in1925
Property size2,872 sqft
Property typeMulti-family

Overview

Active

Listed Oct 14, 2026

Updated 8h ago

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.

$3,054/mo

Est. mortgage payment based on a $459,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
73590382
Available since
October 14, 2026

Interior Features

Bedrooms
6
Bathrooms
3
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.21 Acres

Other Property Details

Taxes
$5,481
Tax Frequency
Annually
Garage
Yes

 

Courtesy of Mandy Fontanez

Based on information from DASH - Coldwell Banker (CB) as of 10/17/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. The display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent. 

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Data last updated 1:08 PM UTC, 10/17/2026

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