106-108 Chestnut St, Southbridge MA 01550
Southbridge, MA 01550
$500,000
$489,900
Est. $3,110/month
Track this home for price, status, and open-house alerts.
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.
View in the App
Save this property, schedule tours instantly, and get alerts when the price drops
Scan with phone
Public Records & Permits
Log in to view assessor & tax records, ownership history, and recent building permits for this property.
BMN Estimate
Get the number an algorithm can't give you
A free agent CMA factors in condition, upgrades, and the street — the things comps alone can't see.
Recently Sold Nearby
Property History
Market Insights
1
Price Changes
2%
Price Range
Property Timeline
Status: Active under contract
Jul 27, 2026
Active → Active Under Contract
Pending Sale
Jul 25, 2026
Offer accepted, sale pending
Price Reduced
Jul 23, 2026
$489,900
$10,100
(-2.02%)
From $500,000 to $489,900 (-2.0%)
Listed for Sale
May 28, 2026
$500,000
Original listing
Agent: Michelle Terry Team
Office: eXp Realty
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/27/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 07/25/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 07/23/2026 | ↓ Price Reduced | $489,900 | $10,100 | - | From $500,000 to $489,900 (-2.0%) |
| 05/28/2026 | 🏠 Listed for Sale | $500,000 | - | - | Original listing |
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
Stories
3
Bedrooms
6
Full Baths
2
Half Baths
1
Total Rooms
14
Investment Metrics
Units
3
Unit 1 Rent
— · N
Unit 2 Rent
— · N
Interior
Heating
None
Cooling
None
Flooring
Hardwood
Appliances
Range, Dishwasher, Microwave, Refrigerator
Fireplace
None
Basement
Full
Laundry
None
Features
Living Room, Dining Room, Kitchen
Exterior
Construction
Frame
Architecture
None
Roof
Shingle
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
Porch
Parking
Garage Spaces
1
Has Garage
Yes
Features
Off Street, Paved
Total Spaces
5
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$5,191
Assessed Value
$354,100
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Certified Treated, Unknown
Seller Disclosures
Seller Trying To Locate Letter Of Compliance For Both Units (see Https://leadsafehomes.mass.gov/leadsafehomes For Reference - 108 Chestnut St.)
Additional Details
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)
75 days
Property Overview
Property Type
Multi Family
Listing Type
Sale Pending
Year Built
1925
Bedrooms
6
Full Bathrooms
2
Half Bathrooms
1
Living Area
2,872 sq ft
Total Rooms
14
Stories
3
Levels
3
Floor Layout
Interactive room guide
Floor Layout
Finished Area
0 sq ft above grade
Display Options
Outdoor Areas
Patio & porchPorch
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
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
Nearby Schools
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
Elementary Schools
5 schools
Trinity Catholic Academy
0.9 mi
Grades PK-08
Viewpoint Christian Academy
2.0 mi
Grades K-12
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
C-
West Street School
1.4 mi
|
#724 of 824
|
Score: 34.0
Improved 18 spots from last year
-24.2 below state avg
323 students
Moderate
Grades 01-05
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
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
Learn about these ratings
Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
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
$0/mo
Cost $0/mo
Payment Over Time
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
Loading map...
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
Aug 23, 2026 10:35 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
Contact Us
Ask about this property — free, no obligation.
Similar Homes for Sale
Comparable Properties
Customize Comparable Search
Finding comparable properties...
Loading market insights for Southbridge.