3 Family - 3 Units Up/Down at 36 Winter Street, Southbridge MA 01550, Southbridge
3 Family - 3 Units Up/Down at 36 Winter Street, Southbridge MA 01550, Southbridge, photo 2 of 13
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3 Family - 3 Units Up/Down at 36 Winter Street, Southbridge MA 01550, Southbridge, photo 4 of 13
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13 photos

$649,999

36 Winter Street, Southbridge MA 01550
Southbridge, MA 01550
Listed by Skerdi Senko
Bedrooms
9
Bathrooms
3
Living area
4,134 sqft
Year built
1900

About this home

Rare opportunity to own a substantially renovated 3-family in Southbridge with strong in-place income and excellent rental potential. The property offers 4,134+ SF with 3 units, each featuring 3 bedrooms and 1 full bath, for a total of 9 bedrooms and 3 full baths, plus a detached 3-car garage. Recent improvements include a new roof, siding, windows, refinished/new flooring, updated electrical service with 200-amp wiring, circuit breakers, and panels, furnaces, water heaters, updated plumbing, lead paint remediation, and enclosed rear porches. Unit 1 features an in-unit washer and dryer, while Units 2 and 3 have their own washers and dryers in the basement. Conveniently located near Route 20, I-84, and I-90, with easy access to downtown Southbridge, shopping, restaurants, schools, parks, medical facilities, and public transportation. With spacious units, valuable off-street parking, and extensive recent updates, this property offers an attractive opportunity for investors seeking cash flow and portfolio growth or an owner-occupant looking to house hack while building equity. Open house will be this weekend, Sunday August 30 between 12:00pm-2:00pm.

Property details

MLS #
73568094
Property type
3 Family - 3 Units Up/Down
Subdivision
N/A
Status
Active
Days on market
36
On market date
August 25, 2026
Stories
3
Total bathrooms
3
Garage spaces
3
Parking spaces
6
Lot size
0.19 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 (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
West Street
0.25 mi away · Grades 1-5
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
312
Student:teacher ratio
10.8:1
District
Southbridge
Middle
Southbridge Middle School
2.07 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
0.32 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).

80
Highly walkable
out of 100
EPA National Walkability Index
14.0 / 20 -- Above average walkable
Google Places amenity density
95 / 100
Restaurants & cafes20
Grocery stores3
Parks6
Schools9
Transit stops16
Pharmacies4

Mortgage calculator

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Est. monthly payment
$4,064/mo
$130,000 down
$519,999 loan
Principal & interest$3,373
Property tax (est.)$542
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 26 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.