Multi Family at 106 Chestnut St, Southbridge MA 01550
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42 photos

$459,000

106 Chestnut St, Southbridge MA 01550
Southbridge, MA 01550
Listed by Mandy Fontanez
Bedrooms
6
Bathrooms
2.5
Living area
2,872 sqft
Year built
1925

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.

Property details

MLS
MLS Property Information Network
MLS #
73590382
Property type
Multi Family
Subdivision
N/A
Status
Active
Days on market
5
On market date
October 14, 2026
Stories
3
Total bathrooms
2.5
Garage spaces
1
Parking spaces
6
Lot size
0.21 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Eastford Road
0.63 mi away · Grades -1-1
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
319
Student:teacher ratio
12.8:1
District
Southbridge
Middle
Southbridge Middle School
1.39 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
407
Student:teacher ratio
12.0:1
District
Southbridge
High
Southbridge Academy
0.72 mi away · Grades 6-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
42
Student:teacher ratio
3.5:1
District
Southbridge

Walkability

Blended score for Southbridge's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

50
Somewhat walkable
out of 100
EPA National Walkability Index
6.0 / 20 -- Below average walkable
Google Places amenity density
80 / 100
Restaurants & cafes20
Grocery stores1
Parks4
Schools6
Transit stops6
Pharmacies1

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$2,914/mo
$91,800 down
$367,200 loan
Principal & interest$2,382
Property tax (est.)$383
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 2 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.