56 Middlefield Rd, Chester MA 01011
Chester, MA 01011
$414,999
$365,000
Est. $2,401/month
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About this home
The price has improved! Don't miss out. Discover this charming and spacious two-family home nestled in the heart of Chester. Recently refreshed with new flooring throughout and thoughtful cosmetic updates, this well-maintained property is ready for its next owner. Each unit offers 3 comfortably sized bedrooms, 1.5 bathrooms, a large living room, dining area, kitchen, first-floor laundry, and a bonus room that can be used as an office, playroom, or additional storage. The property sits on a generous lot—close to 1 acre—with a large front yard and expansive backyard that accommodates parking for approximately 6 additional vehicles. Ideal for anyone seeking a tranquil setting with strong rental income potential or a reliable investment opportunity. A barn with a 2-car garage and upstairs loft adds even more versatility and is being sold as is. The home also includes a new septic system, offering added peace of mind.
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Recently Sold Nearby
Property History
Market Insights
4
Price Changes
12%
Price Range
Property Timeline
Price Reduced
Jul 13, 2026
$365,000
$24,900
(-6.39%)
From $389,900 to $365,000 (-6.4%)
Price Reduced
Jun 3, 2026
$389,900
$5,000
(-1.27%)
From $394,900 to $389,900 (-1.3%)
Price Reduced
Apr 9, 2026
$394,900
$10,000
(-2.47%)
From $404,900 to $394,900 (-2.5%)
Price Reduced
Mar 4, 2026
$404,900
$10,099
(-2.43%)
From $414,999 to $404,900 (-2.4%)
Listed for Sale
Dec 11, 2025
$414,999
Original listing
Office: Executive Real Estate, Inc.
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/13/2026 | ↓ Price Reduced | $365,000 | $24,900 | - | From $389,900 to $365,000 (-6.4%) |
| 06/03/2026 | ↓ Price Reduced | $389,900 | $5,000 | - | From $394,900 to $389,900 (-1.3%) |
| 04/09/2026 | ↓ Price Reduced | $394,900 | $10,000 | - | From $404,900 to $394,900 (-2.5%) |
| 03/04/2026 | ↓ Price Reduced | $404,900 | $10,099 | - | From $414,999 to $404,900 (-2.4%) |
| 12/11/2025 | 🏠 Listed for Sale | $414,999 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $4,264 | $236,100 |
Financial Details
Annual Property Tax
$4,264
Tax Year 2025
Assessed Value
$236,100
Facts & Features
2 Car Garage
Home Facts
Type
Residential Income
Style
Multi Family
Year Built
1900
Living Area
2,832 sq ft
Lot Size
0.70 acres
Bedrooms
5
Full Baths
2
Half Baths
2
Total Rooms
12
Investment Metrics
Units
2
Unit 1 Rent
$2,200/mo · N
Unit 2 Rent
$2,200/mo · Y
Total Monthly Rent
$4,400/mo
Gross Income
$52,800
Net Operating Income
$52,800
Cap Rate
14.47%
Interior
Heating
None
Cooling
None
Flooring
None
Appliances
None
Fireplace
None
Basement
Full
Laundry
None
Features
None
Exterior
Construction
None
Architecture
None
Roof
None
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Garage Spaces
2
Has Garage
Yes
Features
None
Total Spaces
12
Utilities
Electric
None
Water
Public
Sewer
Private Sewer
Gas
None
Other
None
Financial
Annual Tax
$4,264
Assessed Value
$236,100
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Hampden
Total market time (incl. prior listings)
213 days
Property Overview
Property Type
Multi Family
Listing Type
For Sale
Year Built
1900
Bedrooms
5
Full Bathrooms
2
Half Bathrooms
2
Living Area
2,832 sq ft
Total Rooms
12
Stories
4
Levels
4
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,832 sq ft above grade
Display Options
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:
Appliances:
Interior Features:
Windows:
Basement:
Full
Laundry:
Security:
Construction & Materials
Year Built:
1900
Structure Type:
Exterior Materials:
Roof:
Foundation:
Stone
Stories:
4
Heating, Cooling & Utilities
Heating:
Cooling:
Hot Water:
Oil
Water Source:
Public
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Cleared, Gentle Sloping, Level
Road Surface:
Parking & Garage
Garage Spaces:
2
Total Parking Spaces:
12
Parking Features:
Nearby Schools
School District
Gateway School District local
Where Graduates Go
Class of 2021
61%
attend college
41%
4-Year
20%
2-Year
11%
Out of State
0%
Working
School Safety
2024-25
4.2%
Above Average
4.2%
Suspensions
3.3%
In-School
1.3% below state avg
Elementary Schools
1 school
B-
Chester Elementary School
1.1 mi
|
#498 of 824
|
Score: 44.7
Dropped 463 spots from last year
-13.5 below state avg
114 students
Less Diverse
Grades PK-05
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
$355
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
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Neighborhood
56 Middlefield Rd, Chester MA 01011
Chester, MA 01011
Listing Information
Listing Agent
Cynthia Gonzalez
Listing Office
Executive Real Estate, Inc.
Office Phone
413-596-2212
Agent MLS ID
CN240337
Office MLS ID
AC1693
Listing Data Updated
Jul 16, 2026 3:05 AM 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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