“Beautiful and classic, exactly what Beacon Hill embodies,” is how the listing describes an impeccably preserved Federal-style home in Boston’s Beacon Hill neighborhood that’s just hit the market for $10.75 million.

The 1827-constructed property at 28 Chestnut Street was built by a “housewright” (what we now call an architect) named Jesse Shaw, who was reportedly a relative of Colonel Robert Gould Shaw, the Union army officer who led the first all-Black regiment in the Civil War, the 54th Massachusetts Infantry.

The Shaw family was known in Boston as a prominent abolitionist family, and one of the listing’s features makes testament to this fact: a bunker, accessed through the property’s full basement, that was a stop on the Underground Railroad.

The five-bedroom, six-bathroom home includes a two-car garage nestled beside a private deck, all just a few blocks from Boston Common and the Boston Public Garden. An eat-in kitchen, family room and formal dining room all sit on the first-floor level of the home. Meanwhile, the home’s upper floors contain the home office, a master retreat, the additional four bedrooms, a home gym, living areas, a music room, and a sizable library with original detailing.

Although fireplaces are scattered throughout the house, the listing description notes that one in the home’s master bedroom will be especially welcome “for those chilly New England winters.”

In addition to its storied past as a stop on the Underground Railroad, the property also has a more carefree side to its history: the home’s first-floor living room was initially designed as a speakeasy, complete with an entrance out onto bustling Chestnut Street.

“Steps [away] from Charles Street with boutiques, restaurants and the Esplanade and a quick jaunt to Boston Common/Gardens and the ability to enjoy all Beacon Hill has to offer,” the listing description reads.

The property is represented by Beth Dickerson of Gibson Sotheby’s International Realty.

Update: An earlier version of this article stated that the listing agent was a member of TTR Sotheby’s International Realty, but she is an agent with Gibson Sotheby’s International Realty.

Email Lillian Dickerson

Show Comments Hide Comments


Sign up for Inman’s Morning Headlines
What you need to know to start your day with all the latest industry developments
By submitting your email address, you agree to receive marketing emails from Inman.
Thank you for subscribing to Morning Headlines.
Back to top
Only 3 days left to register for Inman Connect Las Vegas before prices go up! Don't miss the premier event for real estate pros.Register Now ×
Limited Time Offer: Get 1 year of Inman Select for $199SUBSCRIBE×
Log in
If you created your account with Google or Facebook
Don't have an account?
Forgot your password?
No Problem

Simply enter the email address you used to create your account and click "Reset Password". You will receive additional instructions via email.

Forgot your username? If so please contact customer support at (510) 658-9252

Password Reset Confirmation

Password Reset Instructions have been sent to

Subscribe to The Weekender
Get the week's leading headlines delivered straight to your inbox.
Top headlines from around the real estate industry. Breaking news as it happens.
15 stories covering tech, special reports, video and opinion.
Unique features from hacker profiles to portal watch and video interviews.
Unique features from hacker profiles to portal watch and video interviews.
It looks like you’re already a Select Member!
To subscribe to exclusive newsletters, visit your email preferences in the account settings.
Up-to-the-minute news and interviews in your inbox, ticket discounts for Inman events and more
1-Step CheckoutPay with a credit card
By continuing, you agree to Inman’s Terms of Use and Privacy Policy.

You will be charged . Your subscription will automatically renew for on . For more details on our payment terms and how to cancel, click here.

Interested in a group subscription?
Finish setting up your subscription