56 Middlefield Rd Chester — Photo 1 of 39
Recent Drop: $24,900
$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.
Key facts
It was listed on December 10, 2025. The price has come down from an original $414,999 to $365,000 across 4 changes, most recently on July 12, 2026. The annual property taxes are $4,264 (2025 tax year). It sits on a 0.7-acre (30,492 sq ft) lot.
Market Value Analysis
Limited sample — based on 6 comparable properties.
* Analysis is based on 6 actively listed and recently sold comparable properties strictly within Chester, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Geography
Property History
$365,000
Was $389,900
Jul 13, 2026
MLS® 73461501
$389,900
Was $394,900
Jun 3, 2026
MLS® 73461501
$394,900
Was $404,900
Apr 9, 2026
MLS® 73461501
$404,900
Was $414,999
Mar 4, 2026
MLS® 73461501
$414,999
Dec 10, 2025
MLS® 73461501
Questions about this home
When was 56 Middlefield Rd, Chester listed?
56 Middlefield Rd, Chester was listed on December 10, 2025.
Has the price of 56 Middlefield Rd, Chester changed?
The price has come down from an original $414,999 to $365,000 across 4 changes, most recently on July 12, 2026.
What are the property taxes for 56 Middlefield Rd, Chester?
The annual property taxes for 56 Middlefield Rd, Chester are $4,264 (2025 tax year).
How big is the lot at 56 Middlefield Rd, Chester?
56 Middlefield Rd, Chester sits on a 0.7-acre (30,492 sq ft) lot.
What is the status of 56 Middlefield Rd, Chester?
56 Middlefield Rd, Chester is actively listed for sale.
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
358 housing units permitted in the last 12 months (+18% vs the prior 12 months) — 63 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
Listing Agent: Cynthia Gonzalez
Listing Office: Executive Real Estate, Inc.
MLS® Number: 73461501
