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106-108 Chestnut St, Southbridge MA 01550

Southbridge, MA 01550
$500,000
Est. $3,161/month
6
Beds
2.5
Baths
2,872
Sq Ft
$174
Price/Sq Ft
0.21
Acres
1925
Year Built
1
Garage Space
43
Days on Market
Active Listed May 27, 2026 • MLS# 73525499 Copied! • Updated Jun 3, 2026

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.

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Recently Sold Nearby

Property History

Property Timeline

🏠
Listed for Sale
May 28, 2026
$500,000
Original listing
Agent: Michelle Terry Team Office: eXp Realty

Tax History

Year Taxes Assessment
2025 $5,191 $354,100

Financial Details

Annual Property Tax
$5,191
Tax Year 2025
Assessed Value
$354,100

Facts & Features

1 Car Garage

Home Facts

Type Residential Income
Style Multi Family
Year Built 1925
Living Area 2,872 sq ft
Lot Size 0.21 acres
Bedrooms 6
Full Baths 2
Half Baths 1
Total Rooms 14

Investment Metrics

Units 3
Unit 1 Rent — · N
Unit 2 Rent — · N
Heating None
Cooling None
Flooring Hardwood
Appliances Range, Dishwasher, Microwave, Refrigerator
Fireplace None
Basement Full
Laundry None
Features Living Room, Dining Room, Kitchen
Construction Frame
Architecture None
Roof Shingle
Features None
Pool None
Spa None
Fencing None
Patio/Porch Porch
Garage Spaces 1
Has Garage Yes
Features Off Street, Paved
Total Spaces 5
Electric None
Water Public
Sewer Public Sewer
Gas None
Other None

Financial

Annual Tax $5,191
Assessed Value $354,100
Fee Includes None
Amenities None
Optional Fee Includes None
Seller Disclosures Seller Trying To Locate Letter Of Compliance For Both Units (see Https://leadsafehomes.mass.gov/leadsafehomes For Reference - 108 Chestnut St.)
Possession None
Accepted Financing None
Structure Type []
Sq Ft Source Public Record
Sq Ft Disclosures 2 unit has been modified over the years- been used as single. Third floor partially finished.
Documents None
County Worcester
Total market time (incl. prior listings) 7 days

Property Overview

Property Type
Multi Family
Listing Type
For Sale
Year Built
1925
Bedrooms
6
Full Bathrooms
2
Half Bathrooms
1
Living Area
2,872 sq ft
Total Rooms
14
Stories
3
Levels
3

Room Details

Other Floor

Bathroom1
Bedroom5
Bedroom4
Bedroom3
Dining Room
Kitchen
Bathroom2
Bedroom2
Living Room
Bathroom3
Master Bedroom
Office
Family Room
Master Bathroom

Interior Features

Flooring: Hardwood
Appliances: Range, Dishwasher, Microwave, Refrigerator
Interior Features: Living Room, Dining Room, Kitchen
Windows:
Basement: Full
Laundry:
Security:

Construction & Materials

Year Built: 1925
Structure Type:
Exterior Materials: Frame
Roof: Shingle
Foundation: Stone
Stories: 3

Heating, Cooling & Utilities

Heating:
Cooling:
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features:
Patio & Porch: Porch
Fencing:
Other Structures:
Lot Features: Other
Road Surface:

Parking & Garage

Garage Spaces: 1
Total Parking Spaces: 5
Parking Features: Off Street, Paved
School District
Southbridge School District local
F
School Safety 2024-25
6.0% Above Average
6.0% Suspensions 6.0% In-School
0.5% above state avg
E

Elementary Schools

3 schools
Eastford Road School
0.6 mi
397 students Moderate
Grades PK-01
D
Charlton Street School
0.8 mi | #782 of 824 | Score: 30.2
Improved 50 spots from last year
-28 below state avg
288 students Diverse
Rising School
Grades PK-05
Trinity Catholic Academy
0.9 mi
Grades PK-08
M

Middle Schools

1 school
C
Southbridge Middle School
1.4 mi | #282 of 352 | Score: 33.3
Improved 1 spots from last year
-24.9 below state avg
380 students Diverse
Grades 06-08
H

High Schools

2 schools
Southbridge Academy
0.7 mi
21 students Diverse
Grades 06-12
C-
Southbridge High School
1.4 mi | #310 of 346 | Score: 35.8
Improved 22 spots from last year
-22.5 below state avg
419 students Moderate
12 sports • 498 athletes
Early College Program Rising School College Ready Curriculum
Grades 09-12
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Monthly Payment Calculator

Monthly Payment
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Loan Amount
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After down payment
Total Interest
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Over life of loan
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Including down payment
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Down: $0
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $433
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Location

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Neighborhood

106-108 Chestnut St, Southbridge MA 01550

Southbridge, MA 01550

Listing Information

Listing Agent Michelle Terry Team
Listing Office eXp Realty LLC
Office Phone 888-854-7493
Agent MLS ID TM326908
Office MLS ID AN8940
Listing Data Updated Jun 3, 2026 1:00 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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