Multi Family at 106-108 Chestnut St, Southbridge MA 01550
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37 photos

$500,000

106-108 Chestnut St, Southbridge MA 01550
Southbridge, MA 01550
Listed by Michelle Terry Team
Bedrooms
6
Bathrooms
2.5
Living area
2,872 sqft
Year built
1925

About this home

Massive 3-unit property previously utilized as a single-family home offering exceptional flexibility for owner-occupants, investors, or multi-generational living! This character-filled property features gorgeous hardwood floors, high ceilings, oversized rooms, beautiful French doors, and formal living and dining areas throughout. Partially finished 3rd floor offers additional expansion potential for living space, home office, playroom, or storage. Town water and sewer. Detached 1-car garage, off-street parking, and situated on a quiet dead-end street in a convenient commuter location close to area hospitals, shopping, restaurants, and major routes. Endless possibilities in this spacious and unique property! Close to the senior center and Morris State Park.

Property details

MLS
MLS Property Information Network
MLS #
73525499
Property type
Multi Family
Subdivision
N/A
Status
Active
Days on market
147
On market date
May 27, 2026
Stories
3
Total bathrooms
2.5
Garage spaces
1
Parking spaces
5
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

Market position

How this listing compares to current activity in Southbridge, from live MLS data.

On the market 147 days -- 51 more days than Southbridge's current average of 96 days.
For reference, the median list price across 142 active listings in Southbridge right now is $394,500.

Mortgage calculator

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

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Adjust tax / insurance estimates
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Est. monthly payment
$3,161/mo
$100,000 down
$400,000 loan
Principal & interest$2,594
Property tax (est.)$417
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 3, 2026.

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.