Hilltop Castle

211 South Main Street · Cohasset, Massachusetts

A castle restored. A story continued.

Discover
The Castle on the Hill

A Tudor castle on ten
acres of history

On ten acres of land that has been farmed, inherited, consolidated, and built upon for nearly two hundred years, a Tudor castle sits at the top of a long private drive in Cohasset, Massachusetts. It is not visible from the street. You have to know it’s there.

Built during the 1920s in the tradition of the grand estates that wealthy Bostonians erected along the South Shore, the castle features a great hall, marble floors, a slate roof, eight fireplaces, and stone walls that merge the building with its hilltop landscape. The town has known it simply as “the Castle” for as long as anyone can remember. The hill it sits on is called Castle Hill.

After years without a steward, the castle is being brought back. A new family is undertaking a full restoration—preserving the original architecture while preparing the estate for a second life as a destination for guests, gatherings, and experiences on one of the most storied properties on the South Shore.

Hilltop Castle, front facade — stone construction with turrets, dormers, and slate roof
c. 1920s
Year Built
10.71
Acres
~8,000
Square Feet
8
Fireplaces

“The past was never erased—
it was layered over.”

Nearly Two Centuries

The story of the land

The property at 211 South Main Street is not a conventional house on a conventional lot. It is the surviving core of a historic landscape—a hilltop that has been farmed, inherited, consolidated into a private estate, crossed by a railroad, registered with the Massachusetts Land Court, subdivided around, and built upon for close to two hundred years.

Pre-1835
The Homestead
The Lothrop and Pratt families work the land as shared pasture, orchard, and homestead. A communal water source—later known as the Spanish Well—serves the community. Ownership is family-based, not parcel-based.
1830s – 1866
The Pratt Farmstead
The Pratt family controls the property as a multi-party farmstead. Deeds show transfers among heirs, undivided interests, and shared occupation. The paths and well rights of daily life will later harden into permanent legal easements.
1866
The Estate
Morgan B. Stetson consolidates multiple farm parcels into a single private estate, marking the transition from working farm to gentleman’s property. The internal circulation—paths, carriage roads, water infrastructure—remains in place.
1870s
The Railroad
A railroad corridor crosses the property. The deed reserves crossing rights for the remaining land, forever—a single clause that forces the property to stay connected through every future change.
c. 1920 – 1930
The Castle Rises
A Tudor Revival castle is built on the hilltop: stone construction, slate roof, great hall with marble floors, eight fireplaces, and a library with an overlooking balcony. A three-car garage with loft completes the estate.
1925
The Subdivision
A formal plan creates modern surrounding lots—but maps routes that already existed. Houses are built around the estate, not the estate carved into houses. The castle parcel remains large.
Present
The Restoration
A new family begins the work of bringing the castle back. Structural assessment, material preservation, and thoughtful adaptation for a second life—as a destination for guests, gatherings, and experiences.
Read the Full History →
The Great Hall — marble floors, exposed timber ceiling, iron chandeliers, and a roaring fireplace

The Great Hall

Marble floors reflect the light of iron chandeliers. Exposed timber beams rise to a cathedral ceiling. A fireplace wide enough to stand in anchors the room. Above, a library balcony with turned balusters overlooks it all.

The Setting

Cohasset, Massachusetts

Twenty miles southeast of Boston, where rocky granite shores meet the Atlantic, Cohasset has been a New England landmark since Captain John Smith landed here in 1614. Its name derives from the Massachusett word Conahasset—“long rocky place.”

By the late 1800s, as the town’s fishing industry gave way to summer leisure, wealthy Bostonians discovered Cohasset’s cool ocean breezes and dramatic coastline. They built the grand estates that still define its landscape—Tudor mansions, colonial revivals, and shingle-style cottages along the coast and on the town’s hills. The castle at 211 South Main was part of this tradition.

Today Cohasset is a charming coastal town with a colonial-era village common, a working harbor, independent shops, and an MBTA commuter rail station connecting it directly to Boston. It is a place that has always known how to balance history with daily life.

Coming Soon

A castle for gathering

Hilltop Castle is being restored to welcome guests for the first time. As the renovation progresses, we will announce specific offerings. Here is what we’re planning:

Private Stays

A castle all to yourself, on ten acres, twenty miles from Boston.

Intimate Ceremonies

Wedding ceremonies and cocktail hours on stone patios, with the hilltop as your backdrop.

Photography Sessions

Engagement, wedding, and portrait photography in a setting unlike anything on the South Shore.

Gaming Retreats

Private weekends for tabletop gaming groups. If you’ve ever wanted to play D&D in an actual castle—this is the place.

Corporate Retreats

Small-group offsites in a setting that guarantees nobody checks their phone.

Stay Connected

Follow the restoration

Be the first to know when Hilltop Castle opens its doors. We’ll share restoration updates, historical discoveries, and event announcements—no more than once a month.