image description — Holmesdale, the summer home of Oliver Wendell Holmes Sr., is on the market for $2.8 million.

Friday Front Porch Feature: The Holmesdale Estate

By Breanna SteeleiBerkshires Staff
05:15PM / Friday, October 30, 2026Print Story | Email Story

PITTSFIELD, Mass. — Are you looking for an extraordinary cottage with a famous past? Then this might be the house for you.

Our Friday Front Porch is a weekly feature spotlighting attractive homes for sale in Berkshire County. This week, we are showcasing 497 Holmes Road.

This home was built in 1847 and has eight bedrooms and 5 1/2 baths. The home is 6,761 square feet with a little over 15 acres. This was the summer residence of renowned physician, poet and author Oliver Wendell Holmes Sr.

The almost two-century old home features original hardwood floors, intricate millwork, and a chef's kitchen. It even includes a billiards room, wine cellar, historic provisions cave, and third-floor staff quarters.

The home's grounds include a heated saltwater pool, a private tennis court, reflecting pond, meditation pergola, screened gazebo, and a guest cottage, along with access to the Housatonic River.

It is on the market for $2.8 million; the listing is with Brenda Durant at Kempf-Vanderburgh Realty Consultants, Inc.

You can find out more about this house on its listing here.

*Front Porch Feature brings you an exclusive to some of the houses listed on our real estate page every week. Here we take a bit of a deeper dive into a certain house for sale and ask questions so you don't have to.

Tags: front porch, historic structure, Real Estate,

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Second Streets Second Chances Awarded $85K for Workforce Re-Entry Program

By Brittany Polito03:00PM / Monday, September 28, 2026

PITTSFIELD, Mass. — A local program for formerly incarcerated citizens seeking a technical career received $85,000 from the state.

On Thursday, the Healey-Driscoll administration announced $2.25 million in Re-entry Workforce Development Demonstration Program grants to 12 organizations that will provide job training, career support, and employment opportunities to 445 formerly incarcerated individuals returning to their communities.

Second Street Second Chances was allocated $84,712 to partner with the Berkshire County Sheriff's Office to offer a training program to 12 returning citizens with a focus on the advanced manufacturing and engineering industry.

The funds will be used to put 12 returning citizens through a training program with a focus on the advanced manufacturing and engineering industry. Successful program graduates will be placed in manufacturing and welding roles at Onyx Specialty Papers and Hi-Tech Mold and Tool.

The program was one of 12 awardees, a majority on the eastern side of the state; Greenfield also saw funding.

"When people return to their communities, they should have a real opportunity to get a good job, support their families and build a stable future," said Gov. Maura Healey in a press release.

"These grants connect people with the training and experience they need to succeed and with employers that are ready to hire."

Lieutenant Governor Kim Driscoll said successful reentry means making sure people have the tools and opportunities to move forward, and these programs bring together community organizations, public safety partners, and employers to connect people directly with training and jobs.

Launched in 2022, Second Street Second Chances' mission is to provide a central point of access for medical and mental health, housing, job training, legal services, and more for a successful reentry into the community.

Early this year, the nonprofit saw an $89,000 grant from the program. Executive Director Lindsay Cornwell at the time said this funding allowed 2nd Street to expand its mission of supporting returning citizens in Berkshire County through meaningful workforce opportunities and a pathway toward sustainable employment.

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