When you have more money than you know what to do with, you make some odd choices, especially with real estate. Just take a look inside the most expensive mansion for sale in Dutchess County, NY.

The $28 million, 12,600 square-foot compound nicknamed Canoe Hill House has been on the market since October 2023. While the home, guest house, and surrounding vineyards (complete with a tasting room and wine production facility) are impressive, some of the most stand-out features don't appear until you walk through the front doors.

Canoe Hill House is the most expensive home for sale in Dutchess County, NY> It also has some of the most interesting design choices of any home in the Hudson Valley
Canoe Hill House is the most expensive home for sale in Dutchess County, NY> It also has some of the most interesting design choices of any home in the Hudson Valley (Zillow)
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Unusual Design Choices Inside Dutchess County's Most Expensive Home

They say that there's no accounting for taste, but maybe when you're rich enough to literally transport a 1700s-era house and have it rebuilt on this sprawling Millbrook, NY property, the rules go out the window.

Just take a look at the hidden "tartan house" behind a secret door inside the main home (below).

The "tartan room" inside Canoe Hill House is the first sign that owners cared more about their personal tastes than broad design appeal
The "tartan house" inside Canoe Hill House is the first sign that owners cared more about their personal tastes than broad design appeal (Zillow)
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Plaid-on-Plaid Inside Millbrook, NY Mansion

This bar and game room is just the beginning of the design adventure. Plaid on the floors, plaid on the walls, and plaid on the curtains should give any potential buyer the feeling that the previous owners did whatever made them happy, without much consideration for future owners. Then there's the living room...

There's always eyes on you in Canoe Hill House, the most expensive home for sale in Dutchess County, NY
There's always eyes on you in Canoe Hill House, the most expensive home for sale in Dutchess County, NY (Zillow)
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Wait Until You See the Dining Room...

Several main rooms, including the large living room and patio dining area, have the theme of "big heads". Whether it's the giant bison mount or the oversized portrait on the opposite wall, nearly any seat in the house will be under someone's gaze. The highlight, however, is waiting in the dining room.

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In a collision course that can only be described as pop-art-meets-the-Fortune-500, each chair in Canoe Hill House's formal dining room has what looks like a hand-painted portrait of some of the most famous faces in the world. From Abraham Lincoln to Frida Kahlo, there's not a bad seat in the house.

Take a look at the chairs (and the rest of the wild property) below.

The Most Expensive Home in Dutchess County, NY is Canoe Hill House

Canoe Hill house in Millbrook, NY has its own gym, movie theater, putting green, and winery

Gallery Credit: Byron Anderson, Daniel Kessler/Compass Greater NY

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