For sale

$414,999

56 Middlefield Rd, Chester, MA 01011

5beds

2,832sqft

Est.:

Multi Family

Built in 1900

-- sqft lot

$409,000 Zestimate^®

$147/sqft

$-- HOA

What's special

First-floor laundryExpansive backyardDining areaBonus roomLarge front yardThoughtful cosmetic updates

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.

34 days

462

19

Tour with a local agent

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 5
Bathrooms: 4
Full bathrooms: 2
1/2 bathrooms: 2

Features

Basement: Full
Has fireplace: No

Interior area

Total structure area: 2,832
Total interior livable area: 2,832 sqft
Finished area above ground: 2,832

Property

Parking

Total spaces: 12
Parking features: Garage
Garage spaces: 2
Uncovered spaces: 10

Lot

Size: 0.7 Acres
Features: Cleared, Gentle Sloping, Level

Details

Parcel number: M:201.0 B:0000 P:0041.0,3971671
Zoning: R

Construction

Type & style

Home type: MultiFamily
Property subtype: Multi Family

Materials

Foundation: Stone

Condition

Year built: 1900

Utilities & green energy

Sewer: Private Sewer
Water: Public

Community & HOA

Location

Region: Chester

Financial & listing details

Price per square foot: $147/sqft
Tax assessed value: $236,100
Annual tax amount: $4,264
Date on market: 1/22/2026
Total actual rent: 4400

Estimated market value

$409,000

$389,000 - $429,000

$1,916/mo

Price history

Date	Event	Price
12/11/2025	Listed for sale	$414,999$147/sqft
Source: MLS PIN #73461501 Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$4,264 +5.2%	$236,100 -0.5%
2024	$4,055 +3.5%	$237,400 +8%
2023	$3,919 +6.6%	$219,800 +14.7%
2022	$3,675 +25.1%	$191,600 +35%
2021	$2,937	$141,900
2020	$2,937 +0.8%	$141,900 +2.3%
2019	$2,913 +5.4%	$138,700 -2.6%
2018	$2,763 -4.5%	$142,400
2017	$2,894 +0.8%	$142,400
2016	$2,871 +1.3%	$142,400 -3.1%
2015	$2,835 -7.6%	$146,900
2014	$3,067 +3%	$146,900
2013	$2,979 +3.8%	$146,900 -2.9%
2012	$2,869 +0.7%	$151,300 -1%
2011	$2,848 +1.5%	$152,800 -8.8%
2010	$2,806 +2.5%	$167,600
2009	$2,737 +5.4%	$167,600 +6.1%
2008	$2,596 +7.6%	$158,000 +9%
2007	$2,413 +4.7%	$145,000 +9.5%
2006	$2,304 +18.9%	$132,400 +28.2%
2005	$1,938 -7.8%	$103,300
2004	$2,101 +7.4%	$103,300 +0.5%
2003	$1,957 +18.6%	$102,800 +1.8%
2001	$1,650	$101,000