The Estate at High Head

High Head is where history meets horizon.

High Head is a luxury oceanfront estate in Brooklin, Maine, offering a unique blend of natural beauty, tranquility, and comfort. Tucked away down a .75-mile long driveway, this private sanctuary spans 30 acres of forest and 1,700 feet of waterfront along Eggemoggin Reach, including a deepwater dock. This summer haven blends modern comforts with the timeless charm of coastal Maine. Built in 1937, this historic family estate transferred to new owners in 2024, who stewarded the property through a thoughtful restoration and modernization. With their care and attention to detail, High Head has retained its historic charm while also offering modern comforts and conveniences.

Cirrus, the 1930 Herreshoff yacht Bemis bought in 1935, has returned to High Head.

High Head Tower

The main sitting room in the tower overlooks Eggemoggin Reach- one of the most iconic views in all of Maine.

Zoom in on bald eagles and ospreys while they nest on neighboring islands.

The deck at High Head Tower

Climb the spiral staircase to the take advantage of the best view in Maine.

Watch the classic sailboats go by from the a bird’s eye view atop High Head Tower.

See all the way to the Atlantic Ocean from High Head Tower’s main sitting area.

Time moves differently here.

Everything worth seeing on the Reach will come to you eventually — you need only wait.

A view that hits you as soon as enter the door...

Sailboats drift past on a blue that changes hour by hour.

A storied property with a stunning restoration...

every beam, board, and stone tells a story.

The new chapter just happens to include exceptional linens and a proper bar cart.

The result is something neither old nor new — something better.

Character this deep can't be designed. It can only be earned — and then, if you're lucky, carefully stewarded.

High Head has been both.

Generations of Maine summers are baked into these walls.

The craftspeople who restored this place understood that. They worked around the memories, not over them.

This is what happens when expert hands meet a property worth saving.

The bones were always exceptional. Now the rest of the house has caught up.

Some restorations preserve a building. This one preserved a feeling —

of woodsmoke and salt air and summer mornings that ask nothing more of you than to be present.

Iconic doesn't just happen. It's chosen, again and again, by the people who care for a place.

High Head has been lucky in its caretakers.

The first decision of the day is the best one you'll make.

Everything you need is right here.

Easy to be in. Hard to leave.

The difference between a rental and a retreat is in what's already been thought of.

High Head Tower Bathroom One

All full bathrooms in the Tower are en suite.

High Head Tower Bathroom Two

All full bathrooms in the Tower are en suite.

High Head Tower Bathroom Three

All full bathrooms in the Tower are en suite.

The Tower's primary bedroom, Nuthatch, has two king beds.

Nuthatch is divided into two separate rooms- each with a king-sized bed. One room juts out into the trees and is a traditional “Maine sleeping porch” outfitted with sliding windows and shades for sleeping in the nighttime breezes and oceanic sounds.

The Chickadee bedroom

Chickadee is a bedroom in the Tower with a king-sized bed, sleeps two.

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Particulars:

3 residences
10 bedrooms*
7.5 bathrooms
Sleeps 22 people
Deepwater dock
4 moorings
Ample recreational gear- kayaks, canoes, etc.
Wifi access
Sports court- tennis, pickleball, and basketball
Outdoor areas with fire pits
Parking
Multiples private common areas on site: garden, playground, and porches

Location Features:

158 High Head Dr, Brooklin, United States

Located directly overlooking the water on Eggemoggin Reach in coastal Maine. The Reach runs along the Blue Hill Peninsula between Deer Isle and the mainland eventually connecting to Jericho Bay off of the Atlantic Ocean.

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Amenities

BBQ gas, Blender, Baby high chair, Coffee machine, Cooking utensils, Dishwasher, Grill, Kitchen stove, Microwave, Oven, Refrigerator, Spices, Toaster, Vacuum cleaner
Air conditioning, Central heating, Fireplace, General heating
Beach front, Near ocean, Ocean view, Rural, Village, Waterfront
Wireless Broadband Internet wireless, Telephone

*one bedroom is an open air, screened-in bedroom that faces the water and night-time breezes

Parking, Private garden, Private playground, Private porch, Private tennis court
Beach chairs, Boat, Canoe, Kayaks, Ping pong table, Sailboat, TV satellite
Bathroom and laundry, Bed linen, Blow dryer, Clothes dryer, Essentials, Iron and ironing board, Shower, Towel set, Bathtub, Washbasin, Washing machine
Carbon monoxide detector, Fire extinguisher, First aid kit, Smoke detector

“I wasn’t prepared for how incredible High Head is- the setting, the privacy, the extraordinary charm- it all comes together to make a bucket list experience. It was unforgettable.”

– Former Guest

Get In Touch

If you're interested in staying at High Head or partnering with us for an event or collaboration, please give fill out the contact form. We’ll be in touch soon.

The Estate at High Head

High Head is where history meets horizon.

Particulars:

Location Features:

BOOK NOW

Amenities

Kitchen & Dining

Heating & Cooling*

Location Features

Wifi & Office

Parking & facilities

Entertainment

Bathroom & Laundry

Home Safety

“I wasn’t prepared for how incredible High Head is- the setting, the privacy, the extraordinary charm- it all comes together to make a bucket list experience. It was unforgettable.”

Get In Touch