Active
273 Days on market
56 Middlefield Rd Chester — Photo 1 of 39

56 Middlefield Rd Chester — Photo 1 of 39

Recent Drop: $49,999

$414,999
$365,000

$365,000

56 Middlefield Rd, Chester, MA 01011

Chester, MA 01011

Beds

5

Baths

3

SqFt

2,832

Style

Multi Family

Built

1900

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.

Market Value Analysis

This Property
Size (SqFt) →Price →

Limited sample — based on 5 comparable properties.

This Property$129/sqft
Local Avg (Chester)$149/sqft
13% BelowMarket Average

* Analysis is based on 5 actively listed and recently sold comparable properties strictly within Chester, MA.

Property Details

Financials

Original Price$414,999
Annual Taxes$4,264

Parking

Garage2
Off-Street12

Interior Specifications

Total Rooms12
FireplacesNone
Flooring--
BasementFull

Climate & Utilities

Heating--
Cooling--
WaterPublic
SewerPrivate Sewer

Building & Exterior

Construction--
Roof--
FoundationStone
ZoningR

Property & Lot

Acres0.7
SqFt Lot30,492
Lot FeaturesCleared, Gentle Sloping, Level

Geography

Property History

Price Drop
$365,000

Was $389,900

Jul 13, 2026

MLS® 73461501

Price Drop
$389,900

Was $394,900

Jun 3, 2026

MLS® 73461501

Price Drop
$394,900

Was $404,900

Apr 9, 2026

MLS® 73461501

Price Drop
$404,900

Was $414,999

Mar 4, 2026

MLS® 73461501

Listed
$414,999

Dec 10, 2025

MLS® 73461501

Population

1,175

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$89K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

19.3%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Hampden County

359 housing units permitted in the last 12 months (+20% vs the prior 12 months) — 74 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

Listing Provided By

Listing Agent: Cynthia Gonzalez

Listing Office: Executive Real Estate, Inc.

MLS® Number: 73461501

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