Louis CK’s Former Historic Shelter Island Retreat Sells Over Ask

A Shelter Island waterfront estate, once a Presidential retreat where Theodore Roosevelt and fcWilliam McKinley stayed, and most recently owned by comedian Louis CK, has sold after several years on the market, for over ask.

Primrose Cottage, as the 1901 Tudor-style residence at 9-7 Westmoreland Drive is known, sold for $4.35 million, more than $50,000 above its current list price.

Carl Gambino and Marco Maida of The Gambino Group at Compass represented the sellers. There is no word on who the buyers are.

The home was the site of the 1905 informal debut of Peter Pan and baseball legend Babe Ruth stayed there as a guest of then-Congressman James Roe, who had purchased one of the biggest tracts of land on the area of the island called Westmoreland.

Over the last 10 years, Louis CK meticulously restored and modernized the house after purchasing it for $2.44 million in 2014.

The preservation effort included blending original millwork and plastic, along with historic fireplaces — six to be exact — with contemporary amenities and today’s comforts, such as central air conditioning, upgraded heating and energy-efficient insulation.

Among the upgrades is a chef’s kitchen, reimagined with top-of-the-line appliances and finishes and a newly added butler’s pantry to make entertaining a breeze.

The six-bedroom, four-and-a-half-bath home offers nearly 5,000 square feet of space.

Sitting on 2.2 acres, the house is complemented by a new 20-by-50-foot heated gunite pool and a hot tub, surrounded by a classic brick patio.

The deepwater dock on West Neck Creek offers enough room for multiple boats and easy access to the pristine Shelter Island waters.

Louis CK listed the house in September of 2024 for $7.95 million, and relisted it for $4.3 million in August of 2025. A pending sale was listed by the end of August.

The deal closed on October 31, 2025.

Check out more photos below.

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