Shelter Island's $33,000,000 Fixer Upper

SELLER: Chris Knight
LOCATION: Shorewood Road and Apple Orchard Lane, Shelter Island, New York
PRICE: $33,000,000
SIZE: 8 acres, 8,500 square feet, 13 bedrooms, 5 bathrooms
DESCRIPTION: (reduced from the listing agent's website) Possibly the most sought after piece of property in the Hamptons area is located on the bluffs of Ward's Point and commands unmatched 270 degree panoramic views...The estate is situation on 8 pristine acres with more than 1,000 feet of shoreline. On the bluff sits a Victorian Manor house built in 1873. The lawn trails off to a waterside honeymoon cottage. The property also has a turn of the century water tower.

YOUR MAMAS NOTES: Your Mama is on the move and since we're out on the East End of Long Island today we thought we'd bring the children some crazy East End real estate pornography. Technically this house is an aging and fading porn star with a storied past and sagging boobs, but it's nothing some good cosmetic surgery and a skin peel can't fix.

This property, known as Shorewood Manor, was recently snapped up in a private sale by a Shelter Island local by the name of Chris Knight, who clearly knew a good thing when it kicked him in the teeth. The estate was sold by former New York governor Hugh Carey, who purchased the shabby but genteel property in 1997 for $5,000,000. After Carey purchased the old lady, he talked a big talk around the island about all the grandiose plans he had for the estate. But Your Mama is here to tell you that the man didn't touch a stick or nail on that property. He did have a caretaker who kept the lawns mowed and house from falling down, but otherwise it sat lonely, forlorn, and unfortunately, neglected.

How do we know this? Because Your Mama has been to this property. Many times. More on that later.

Last year there were rumblings Carey was interested in selling off some of his Shelter Island holdings including this large parcel on the Southern tip of the island. According to Forbes, and the eventual buyer Chris Knight, Carey never intended for the property to hit the open market. So it was squietly shopped around to high end brokers in on the East End. There were no takers until local boy Chris swooped in and paid an astounding $10,000,000 for the bedraggled and nearly dilapidated property, which by the way, is for all intents and purposes, uninhabitable.

How do we know? Because Your Mama has been inside this house and we have seen the kitchen and bathrooms. You wouldn't open a can of tuna in that kitchen and you certainly wouldn't strip down to take a shower.

After closing on the property, nervy Chris Knight turned around, and just two short weeks later put the property back on the market for $33,000,000. Honestly Your Mama is not sure if this is greed, real estate savvy, or a large dose of both that we're looking at here. Either way, we suspect Mister Knight will be sitting on a huge of wad cash when he gets this white elephant sold. It may take awhile before some enormously rich person is willing to cough up more than $30,000,000 for a house that needs several millions in renovations and grounds that will require one or two more.

Now let Your Mama speak a few words about our own experiences on this property. Back in the mid and late 1990s Your Mama and a few pals, whom we'll call Mommy and The Chicken, used to ride our bicycles around Shelter Island. Of course this is back when Your Mama could pump one of those two wheeled death machines. Anyhoo, one sunny summer day we came across this clearly abandoned property.

So trespassing we went. No babies, we are NOT encouraging anybody to trespass. Ever. But we were young, dumb, and very curious. The first time we crossed onto the property we we tramped around what was once a large terraced garden at the eastern end of the property. In the large photo above that is the large rectangular area on the right hand side of the photo. These gardens must have once been beautiful, but not, they are just terraced areas of lawn with a few rank and uncared for ponds.

The second time we broke the law and walked on to this property we made our way to the waterside honeymoon cottage with it's sweet little deck that hangs over the lapping waters of the Peconic Bay. The cottage was filled with junk, rotting patio furniture and gardening tools.

The next time we came to the property we were bold enough to walk up the bluff and right onto the porch of the house. We peeked in windows and saw the place was completely empty. So around the back of the house we went and what did The Chicken find? That's right, an unlocked door.

So like the budding criminals we were, we walked right into the house and began to wander around. Through the kitchen, which was commodious, but ridiculously outdated. Through the dining room and into the front hall with it's staircase to the second floor. There are two parlors at the front of this house, each with a fireplace. The larger of the two and the Southern most room of the house was long and narrow with evenly spaced floor to ceiling windows. In between the windows were mirrors. Yes, children, mirrors. Very Glammy.

On the second floor, a half dozen or so bedrooms are clustered around the front stair hall, and towards the back, a long series of small rooms are laid out much like a sleeping car on a cross-country train. The sun began to set, and because we didn't have flashlights, we decided to leave the house. We sat out on the bluff and watched the sun dip down over the water and children it was spectacular. This is truly one of the finer locations on Shelter Island where you can sit and watch the sun both rise and set over the water.

The next time we "visited" the property things got a little dicey. As we roamed the upper floors we found a ladder like staircase that led up into the lookout tower, a small open air landing with 360 degree views. A truly extraordinary spot. So Mommy and I sat down and proceeded to partake in an illegal substance (yes, children, Your Mama has been there and done that) while The Chicken continued to roam around the house.

Next thing we know, we heard voices. Unfamiliar voices. Mommy and I peeked over the roof and saw a couple of people we did not know walking towards the house. Our hearts started to race and we were convinced in our substance induced paranoia that we were about to be hauled off to jail.

The strangers actually came into the house and we heard them wandering around, opening and closing doors. The Chicken, in her infinite wisdom and trespassing experience, hid in a small, dark closet while Mommy and I sat on the door in the floor of the lookout tower in the hopes the other trespassers would not try to come up into the tower.

Finally they left and we quietly and quickly removed ourselves from the property. Your Mama wishes we could say that was the last time we visited the property, but it was not. Over the years Your Mama has trespassed on that property more times than we can count.

And we are here to tell you the property, the house, the cottage, the water tower, all of it, is truly magnificent and has a very special aura about it. We know that sounds hokey, but it's true. We sincerely hope someone will buy this property and maintain and preserve its simple elegance and not tear it down to build another Mcmansion. This house is surely one of the last of it's kind anywhere on the East End and it would be a shame to see it go the way of the bulldozer.

Sources: Forbes, Prudential Douglas Elliman