Dreamy Retreat

If you know where to look, many properties in Westport are found down the tiny lanes that veer off its back roads; some are not just wooded lots, but surprising oases of beauty and delight. Often, these hidden gems function as natural retreats for those who maintain homes in city and country, offering respite from a more hectic business and social schedule elsewhere.

One such property, the most private on the site of an old estate, caught the attention of Robert and Laurie La Penta, who had been looking for such a jewel to no avail. “We probably looked at a hundred houses before we saw this one,” remembers Robert.

“I told the real estate agent not to bother showing it to my husband,” adds Laurie, who notes that the house as it was then had neither charm nor an ideal layout.  The home’s façade was overgrown, crowded out by shrubs that added nothing to its presence. In the opinion of a couple who spend much of their time in the milieu of thoroughbred racehorses, it did not look like a winner.

Nonetheless, something prompted Robert to stop by and take a walk around. He noted the old quarry pond at the back of the house and the peacefulness of the setting. Something clicked.

The house needed more than a little tweaking, and the landscape needed complete transformation, but once the La Pentas decided to acquire it, a renaissance began. Enlisting the help of Glen Gate Company, a landscape design, installation and maintenance business based in nearby Wilton, the couple put their instincts for the property’s potential in the hands of its team to complete the vision that they had.

“We take a collaborative approach to a project,” notes Glen Gate Managing Partner Jordy Scott, who assembled a group of designers from his firm’s hundred-plus employees to reclaim what the La Pentas imagined would be a perfect retreat away from their city life.

“The landscape had not been touched since the house was built,” notes Brandon Jones, Glen Gate’s principal designer. After clearing the overgrowth around the home’s perimeter, the team reworked the approach, and completely rethought the back of the property.

“There was nothing there,” says Robert, as Laurie nods toward the back windows of the house, which flood the interior spaces with light and provide views of the landscape from every window. Since the property includes wetlands and contains a large portion of a pond within its boundaries, the redesign had to be carefully crafted to gain approval from town regulators and neighbors, and the landscape company worked through that process—about a year—to allow for the transition.

Then it was time for construction. In addition to a sunken outdoor kitchen to complement the renovated home’s large back patio, the pool emerged as a free-form structure rather than a conventional rectangle—one of Laurie’s inspirations. It offers walk-in entry, a whirlpool and a waterfall, all surrounded by large boulders and designed to look as much like a natural water feature as the pond, which is just steps away.

In the front of the house, a paved courtyard, where guests can park and admire the reworked façade, replaces the original driveway. Instead of a straight shot to the garage bays, a sinuous drive from the front gate provides a sense of arrival; the courtyard is bordered by beautiful walls topped with a classically patterned, custom-designed wood fence.

As the hardscape was installed, evergreens were trucked in; thirty-five-foot specimens were lifted by crane and planted in a natural, staggered pattern along the property perimeter, rather than in a straight line.

Says Jones, “The tall white pines were what you might call ‘quilted together’; they give privacy where it’s needed, and there are open spaces for good views where screening is not required.”

Creative Designer Debra Woodhouse set to work on the planting of flowers and shrubs. A process of adding, subtracting and moving plants around the landscape continues, with adjustments made in every season. Property Manager Cheryl Russ tends to the planting and transplanting and keeps everything in top condition.  

In mid-winter, the bones of the landscape reveal pattern and texture that pleases the eye, even with the neutral palette of February or March. In spring, the fruit of so much effort and care begins to reveal itself. A flowering dogwood by the pond, and other specimen trees around the property start the spring show. As the season warms, thousands of daffodils push out their blossoms along the driveway. And in high season, the garden beds become a spectrum of color, with something new blooming almost daily.

What has finally emerged is a private sanctuary. As the project moves nearly a decade out from its inception, the owners’ affection for its many appealing features solidifies their relationship with their surroundings. Laurie talks about how much they love the opportunity to feel connected to the natural world outside their door.

“When we installed the pool and decks, we had a sound system wired in so that we would be able to listen to music outside.  Sometimes when he’s sitting by the pool, I’ll ask Robert if he’d like to listen to something, but he almost never wants the sound system; he prefers to sit back and enjoy the voices of the birds and the breeze blowing in the trees. It is perfect as it is.”

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