The front door of an 8,165-square-foot home with seven bedrooms and seven-and-one-half baths at 5816 Winland Hills Drive. Photo courtesy of Coldwell Banker Global Luxury

The front door of an 8,165-square-foot home with seven bedrooms and seven-and-one-half baths at 5816 Winland Hills Drive. Photo courtesy of Coldwell Banker Global Luxury

— On the southwestern edge of Rancho Santa Fe, tucked in between the communities of Del Rayo Estates, Del Mar Country Club and Montecito is Winland Hills. It’s an exclusive community off San Dieguito Road with just a handful of grand, gated estates — among the largest in all of San Diego County. Winland Hills Drive is easy to miss from San Dieguito Road and has the feel of a private, paved country road. It’s no more than a third of a mile long with no other connecting arteries, so it’s used only by the residents who live along it.

Gloria Shepard and Kathy Lysaught, realtors with Coldwell Banker Global Luxury, have the listing on a home at 5816 Winland Hills Drive on the northern edge of the enclave. The estate is on a fully fenced 3.11-acre lot obscured from the street by mature landscaping. Off of Winland Hills Drive, a circular paved entry leads to an electronic gate with an intercom. Once inside, the long, sweeping driveway curves gently up a hill to an elevation of about 100 feet above sea level to reveal an 8,165-square-foot home with a four-car garage. The sprawling estate overlooks the mountains to the north, the evening sunsets to the west, as well the 229-acre thoroughbred training center sold by weight loss entrepreneur Jenny Craig to Bill Gates in 2014.

The sale of the training center to Gates ensures that the area will likely remain an equestrian facility and not subject to future housing development, an important detail not just to Craig during her quest to sell the property (October 2014 San Diego Union Tribune story by Diane Bell and Jonathan Horn) but also to the surrounding community.

The home is priced in a value range from $4.749 million to $5.249 million.

“The views are phenomenal,” Shepard said. “You overlook Bill Gates’ new stables, you get to see all the work that’s going on there and you get the sunset sky, it’s just beautiful.”

Shepard said unlike most of the homes in Rancho Santa Fe that are not near daily conveniences, Winland Hills is “what we call coastal close, you’re still in Rancho Santa Fe, but you’re close in.”

It’s what some might consider the “sweet spot” for a Rancho Santa Fe address. Del Rayo Village is nearby and home to the weekly Rancho Santa Fe Farmers Market that takes place every Sunday. Shepard said this quaint shopping center, has several amenities, among them a post office, gas station, pizzeria, bicycle shop and ice cream store. Within walking distance from Del Rayo Village is another small shopping center, Fairbanks Ranch Village Plaza with other amenities, including medical offices. Interstate 5 is about six miles away where the Flower Hill Promenade and the Del Mar Center are on Via De La Valle, and the world-famous Del Mar beach is just a couple of miles from there.

“The home was built in 2002 and has six en suite bedrooms in the main house and a detached casita with its own private entrance and patio,” Shepard said. “Four of the bedrooms are upstairs in the main house with the master suite and guest suite downstairs — the one-bedroom casita is off of the pool.”

Shepard said the floorplan is perfectly designed for multigenerational living, “you can have both parents inside and out of the house.”

The home has been recently refreshed with new paint and other enhancements.

“It’s one of those houses that’s really special and unique,” Shepard said. “The grounds are so manicured, perfectly shaped — anywhere you look, you feel like you’re in a park or a villa.”


The foyer and formal living room. Photo courtesy of Coldwell Banker Global Luxury

The grounds are stunning, indeed. A boulder-lined babbling brook with Japanese style bridges is an enchanting touch; elsewhere a long wooden stairway leads down to the half-court basketball/pickle ball area. Nearby is a large grassy area for the kids and dogs to run free on the completely fenced acreage.

The pool and spa area has connected indoor/outdoor areas where you can watch television or barbecue with all the items necessary for outdoor cooking and living.

Shepard said everyone can gather in the courtyard between the casita and the main home. If parents or older children are living with you, the focal point is the outdoors.


The pool and spa area at dusk with hot air balloons. Photo courtesy of Coldwell Banker Global Luxury

You’re just in your own world, yet you’re accessible to everything,” Shepard said. “It’s a one of a kind beautiful home.”

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