During the coldest months of the year, daydreaming about where you’re going to spend the summer can do wonders for your mood. Architecture buffs who pine for a dreamy modernist retreat with pretty water views in one of the charming towns or villages at the eastern end of Long Island now have Shelter Island’s Osofsky House as an option.

Designed by the architect Norman Jaffe in 1971, the dynamic stone and glass home sits on 1.7 acres with 175 feet of frontage on Gardiners Bay. The residence was expanded in 1981 by Jaffe himself, a rarity for the architect, and additionally modernized in recent years, with updates taking care to preserve the original design while bringing the property up to today’s living standards.

At the center of the home is an expansive living area, where a stone fireplace provides warmth and full-height walls of glass frame the water views just outside. The newly overhauled ground-level chef’s kitchen includes a small dining area for casual meals, but if you’re entertaining guests, the formal dining room is found upstairs, where a chic wet bar sits at the top of the landing. Nearby is a movie theater and a couple of home offices.

The bulk of the six en suite bedrooms and 10 bathrooms (eight full baths and two powder rooms) are found on the main level, some clustered in a separate wing with a central lounge. The serene primary suite takes up the entire upper floor, where there’s a private terrace for the homeowners’ use. A lower-level gym completes the indoor offerings.

The house wraps around a stone-paved courtyard and an extra-deep heated gunite pool that is heated for maximum enjoyment. Summer parties are made easy at the outdoor dining pavilion, which includes its own kitchen and fireplace. This area is topped off by a pergola for a little shade when the sun is high. A tennis court (with pickleball lines) sits farther out on the property, next to manicured gardens planted with wildflowers and the like. 

The Osofsky House is available for $18 million with Nick Brown and Lidia Murphy at Sotheby’s International Realty, East Hampton Brokerage, making it the most expensive home currently for sale on Shelter Island. 

It’s not every day that a Jaffe pad pops up for the taking. A 1970s mansion in Long Island’s tony Old Westbury neighborhood was on the market a couple years ago at $13.5 million, and a Bridgehampton home was listed last year at $22 million, while the Bliss House in Southampton is in pending sale with a $22 million asking price.

Click here to see all the photos of the Osofsky House.