Inside a Quintessential Cape Cod Escape

July 15, 2025

On the breezy shores of Nantucket Sound, this new Osterville residence and guesthouse carry on the timeless characteristics of Cape Cod, paying homage to the beloved Shingle style while imparting creative contemporary sensibilities.

In many circles of thought, the homes of Cape Cod epitomize the classic American architectural aesthetic. Adopted by notable architectural firms of the 19th century, Shingle style gained popularity through commissions for seaside cottages in prestigious locations along the East Coast. Unlike the 17th-century Cape Cod homes, residences designed in this relatively newer fashion are known for their intriguing asymmetry, expansive floor plans, eye-catching rooflines, prominent porches, rounded towers, bay windows, and—naturally—an abundant use of shingles. The style became so quickly beloved that it spread beyond the shores of the United States to become one of the most readily recognizable in the world.

Osterville, Massachusetts | Gene Orloff, Sotheby’s International Realty – Osterville Brokerage

On a grassy perch above the sand and waters of Nantucket Sound, this new residence in Osterville—constructed in 2020—carries on the timeless characteristics of this coveted coastal style. The esteemed firm PSD paid appropriate homage to the beloved vernacular while imparting creative contemporary sensibilities, beginning with the eye-catching lines of the prevailing gambrel roof, which here are artfully smoothed into a graceful variation resembling an ogee arch. The 6,830-square-foot interiors are a vision in warm woods, crisp clean whites, mesmerizing shades of blue that echo the sea and sky, and abundant glass that admits magnificent natural light and focuses the eye on the captivating surroundings.

Among the alluring public spaces on the main level are a formal living room with a fireplace, a dramatic coved ceiling, and a postcard-worthy vista; a sitting alcove with a wet bar, cozy window seats, and built-in bookshelves; and a bay-windowed formal dining room with French doors opening to an ocean-facing terrace. A butler’s pantry segues to a sophisticated kitchen with an island, marble countertops and backsplashes, superior-caliber appliances, and a breakfast room ringed with windows. Beyond is a cheerful family room with a pitched ceiling, a fireplace bordered by boating-themed tiles, a wall of built-ins, and a wall of sunny windows.

Both a discreet elevator and a gracefully winding and curving staircase ascend to the upper level and the generous private quarters. The primary bedroom has an airy, lofty feel thanks to a soaring pitched ceiling and a bank of windows providing a dreamy ocean view. The en suite bath features a roomy shower partially enclosed in glass, ample fixtures and fittings in bright brass, and a wall of glass that begins to blur the boundary between indoors and out. Completing the suite are a light-filled walk-in closet and an office. The second bedroom also boasts soaring ceilings and plentiful windows, while a versatile space atop a classic turret can serve as a virtual crow’s nest, an ideal spot for watching boats and birds sail by or stargazing at night.

Short- or long-term visitors will appreciate the style and privacy of the freestanding guesthouse. Mirroring the main residence aesthetically, it provides a spacious, inviting living and dining room with a fireplace and a kitchenette; two tranquil bedrooms; and its own deck facing the ocean. Between the homes and the estate’s private beach are a sun-washed terrace and an impossibly green lawn. Every necessity—and in truth, many desires—have been ensured at this true, quintessential beach house, which, one could argue, represents both the literal and the figurative architecture of Cape Cod living.