Top Five Estates We'd Be Very Classy In

It’s fun to pretend what life would be like in an extravagant estate. Would we settle in quickly?—“Garcon, chop chop!” Or would it take time to adjust to the new lavish lifestyle?—“Garcon, when you have a moment, would you be so kind as to fan us with palm fronds?” We decided to spotlight a few local mansions, both past and present, and imagine what our oh-so-classy lives would be like inside them.

Would you look at all that land?! Wooldon Manor once spanned an incredible 14 acres in Southampton Village. We’d probably play a mean (and, ultimately, maddening) game of hide and seek. Because we’re sophisticated like that. The property does, in fact, have a history of far more cultivated personalities who lived there, including members of the Woolworth family and Edmund Lynch, a founding partner of Merrill Lynch. It has since been sold and subdivided into lots that are still large enough to suit our extravagant dreams.

Meet the venerable Bouwerie mansion on Meadow Lane in Southampton. This three-and-a-half story villa was built in 1930 by a doctor and his wife. Rumor has it that the inspiration for the home came from a villa the couple saw while on their honeymoon in the south of France. If it hadn’t been demolished last year, we’d pretend we were on a Mediterranean vacation/drama train with lots of wine and our closest frenemies, a la Bravo’s “Housewives.” Rest assured, there would be no shortage of drunken finger wagging!

Farther east in Water Mill rests this palatial estate, with lawns that stretch out to Mecox Bay. Known as the Villa Maria, this once 14.6-acre property first belonged to the Dominican Sisters, who used it as a school, convent and spiritual center starting around 1930. In 2005, the one and only Vincent Camuto, the founder of Nine West, and interior designer Louise Camuto, purchased the property. The land has been subdivided and the villa is back on the market. Honoring the history of these former residents, we’d probably just host a wholesome yoga retreat donned in high end workout gear. Don’t worry, we’d leave those see-through yoga pants at home. Nobody needs to see that.

On an ultra-private peninsula in Wainscott, this world-class 25-acre estate has sweeping water views. Overlooking Georgica Pond, the property known as Burnt Point is awash in luxury amenities, from the waterside pool with adjoining spa, to the tennis court and dock. There are not one but TWO elevators, a beamed library, a professional screening room and a wine cellar. There’s not much else to do on this property but sit and be gone with the wind fabulous. (Yes, sadly, that IS another “Housewives” reference.)

We’re going to end on a castle. Because, castle. Standing proud at 16,000 square feet is this famous estate in Water Mill. Belonging to “Sir” Ivan Wilzig, this castle is replete with amenities, think billiard and game rooms, a gym, tennis and volleyball courts and a swimming pool with a dragon goddess sculpture. There’s also an eight-car garage and a dungeon filled with stuffed bunnies. You heard us. The king of this castle is known for his overindulgent parties, and, frankly, if we lived there, so would we. Come on, what else are you supposed to do in a modern day castle if not be debaucherous?