Concealed behind a hydrangea and rose-clad stucco wall on Wianno Head is a compound that’s so confident of its status that it makes itself one with its natural surroundings.

“This is one of the most magnificent properties in Osterville,” says landscape architect Dan K. Gordon, the founder and principal of the firm that bears his name. “It has water views on three sides; it’s wonderful to work on a site that has spaces with multiple water views.”

The fact that the property is so exposed created constraints and opportunity, adds Peter Stephens, project manager and principal at Dan Gordon Landscape Architects. “We had to come up with ways to preserve the views while mitigating the prevailing winds.”

At the owners’ request, the outdated Mediterranean-style stucco house was renovated and modernized by Daniel H. Reynolds Design Collaborative in a classic New England shingle style, setting the groundwork for landscaping by the Gordon team.

“It’s a landmark property,” Gordon says. “The owners really wanted to develop the character of the house, and the property, into a seaside shingle vernacular. To that end, the landscape improvements were transformational.”

Gordon and his team exploited the spectacular water views, overhauling the gardens on the 2.5-acre property to develop a design that incorporates spaces for maximum active enjoyment of the landscape.

The property, at the termination of a dead-end street, was pretty much a blank slate: A grassy back lawn opens to a vegetated dune that separates the maintained landscape from the seawall and ocean.

To protect the property from storm damage, the seawall was rebuilt and heightened, invasive vines were removed, and the dune was restored with native plantings. A deteriorating sunken garden at the rear of the house was removed and replaced with a pool and pool garden.

“There were mature trees growing throughout the property,” Stephens says. “We worked to preserve the trees and plantings, transplanting hundreds of shrubs–it was like re-arranging the furniture in a house.”

The edited plantings are bolstered by hundreds of new ones, creating layers of flowering shrubs and perennials, including hydrangeas, roses of Sharon and rhododendrons, ornamental grasses such as feather reed and fountain grass, and groundcovers, notably liriope.

The Gordon team reimagined the space as three hubs of activity: a firepit terrace, a pool terrace, and a dining terrace.

The redesign started with the driveway, whose looped parking court, deposited visitors at the guesthouse first before branching off to the main residence. The drive itself was redone, lined with cobblestones and filled with pea stone. Parking at the main house was screened by hedges and perennial plantings.

The drive’s layout was reworked, and an entry gate installed at the street. 

“The compound is very hidden from the street, and there’s a planted buffer between neighboring houses,” Stephens says. “If you didn’t know it was there, you would not see it, which makes it intriguing.”

The stucco guest house, which was re-roofed to match the revamped main residence and which has its own kitchen, parking court, terrace, outdoor shower and dock, is now appropriately set back from the main drive.

The separation is emphasized by a privet hedge and plantings of Oakleaf and Limelight hydrangeas and Hayscented ferns as well as a secondary drive. 

Next to the main parking court, Gordon’s team added a potting shed and vegetable garden for the family’s enjoyment. It’s enclosed with a cedar and wire fence that keeps rabbits out and creates a clean architectural edge to the parking court.

One of the key changes to the property was adding an infinity-edge pool at the rear of the house where the sunken garden had been. 

“It’s a central feature of the landscape,” Gordon says, adding that there was no existing pool. “It’s slightly elevated from the lawn space to create a seamless connection between the main family living space and the adjacent solarium. The elevated nature of the pool garden allows for shorter fences to be used for security around the pool while preserving the views.”

The new firepit terrace, with a cabana that has been rebuilt as a beach bar, also is at the back of the house. A custom pergola, complete with motorized screens at the bar, and glass fences at the dining terrace and pool help reduce wind in key areas.

The dining terrace, another family gathering spot, is off the kitchen. It has a built-in grill and custom cabinetry and supports a private chef and serving staff for the family’s frequent entertaining.   

“Our design is casual yet deliberate and transforms an outdated property into a refined family compound with modern amenities for contemporary living,” Stephens says. “We took what was there that was good and made it more usable. We developed spaces for people to enjoy outside.” 

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