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
3 Family - 3 Units Up/Down at 36 Winter Street, Southbridge MA 01550, Southbridge, photo 3 of 13
3 Family - 3 Units Up/Down at 36 Winter Street, Southbridge MA 01550, Southbridge, photo 4 of 13
3 Family - 3 Units Up/Down at 36 Winter Street, Southbridge MA 01550, Southbridge, photo 5 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, Saturday August 29 or Sunday August 30. Will updateThursday.

Property details

MLS #
73568094
Property type
3 Family - 3 Units Up/Down
Subdivision
N/A
Status
Active
Days on market
2
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 · public school directory data (NCES)

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

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 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.