Inside Connecticut’s Hay Island

March 18, 2025

With its main residence, guesthouse, outdoor living spaces, infinity-edge pool, two beaches and a dock, private Hay Island near Darien meets all the requirements for a consummate sanctuary.

When pondering the notion of a coastal New England estate, several aspects come immediately to mind: timeless architecture—ideally Colonial or Shingle in style or inspiration—plentiful postcard-worthy views, interiors combining charm and a dedication to a classic aesthetic, terraces and balconies, a swimming pool, and perhaps a sandy beach with a dock lapped by waves—all surrounded by expanses of verdant lawn and towering trees that have endured for decades or longer.

Darien, Connecticut | Leslie McElwreath, Sotheby’s International Realty – Greenwich Brokerage

This seaside sanctuary on Hay Island—minutes from Darien, Connecticut—checks all the boxes with its wooded acreage, multiple outdoor living spaces, an infinity-edge pool and spa, and two beaches—a sheltered dock—ideal for swimming, sunbathing, fishing, kayaking, or boating. While the 8,684-square-foot main residence was constructed in 2010, it honors the architectural traditions of its Colonial-style forebears, suffused as it is with an Old World elegance, that natural glow particular to coastal locales, and sweeping southeasterly views across greenery to the shoreline, the Long Island Sound, and the historic Greens Ledge Lighthouse.

Spanning 18.15 acres, the island is a rare gem that has been owned by the same family for more than a century. Internationally lauded architect Austin Patterson Disston conceived the home to mirror the magnificence of its setting, ultimately creating a six-bedroom haven accented by eye-catching millwork, handsome columns and arches, refined finishes, and six warming fireplaces. A brick-paved veranda spans its entire rear length, providing perfect perches for basking in sea breezes, sunshine, and enviable outlooks.

Spaces for effortless day-to-day living and entertaining abound indoors. The formal living and dining rooms feature walls of windows directing the eye toward the inimitable vista. The cook’s kitchen is accompanied by a butler’s pantry, an office, and a solarium-like breakfast room with a fireplace that opens to a stone terrace with a built-in grill. Nearby is a light-filled family room accessing a delightful screened-in porch. Completing the main level are an august wood-paneled library with custom bookshelves, window seats, a wet bar, a fireplace, and doors to the veranda; a peaceful guest suite with a marble bath; a mudroom with a full bath; a workshop; and a three-car garage with a playroom and fitness room on its upper level.

On the second level, the primary suite comprises a bedroom giving way to a balcony designed for appreciating sunrises over the water and a luxurious marble bath with a soaking tub and a pair of dressing rooms. The two guest suites on this floor also enjoy picturesque vistas. Crowning the residence is a level that includes two quiet bedrooms and baths along with an office that—fittingly for these environs—recalls a ship captain’s quarters with its deep-set windows and high, expansive views.

From a certain vantage, the waters of the infinity-edge pool seem to flow uninterruptedly into the surrounding sea. Accompanying it are a sun-washed stone terrace and a pool house with a kitchenette and a bath. Any sophisticated getaway—and certainly a private island—requires space for visitors. The charming two-bedroom guesthouse offers a kitchen and breakfast area, an office, a family room with a fireplace, and a terrace overlooking Ziegler’s Cove. Beyond, tall trees provide cool shade, and paths meander to the garden, the “great lawn,” a spring-fed pond, and secluded spots with undisturbed views. High above the sound at the end of a gated causeway, this quintessential coastal New England property is a rare opportunity, a consummate sanctuary and an island of one’s own.