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Payne Stewart’s widow, Tracey, sells their Isleworth mansion for $7.12M

This 11,079-square-foot home on Chestnut Ridge Drive in Windermere’s exclusive Isleworth community just sold for $7.12 million.
This 11,079-square-foot home on Chestnut Ridge Drive in Windermere’s exclusive Isleworth community just sold for $7.12 million. (UNEEK Luxury Photography)

The dream house PGA legend Payne Stewart designed just before his death has a new owner.

The 11,079-square-foot home on Chestnut Ridge Drive in Windermere’s exclusive Isleworth community just sold for $7.12 million. Stewart’s wife, Tracey, completed the house in 2002 and raised the couple’s two children there and lived a private life.

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“[Payne Stewart] never even got the chance to live in it since it was completed after his passing, and this is the first time it was ever for sale,” said Ron Ziolkowski with Re/Max Prime Properties, who represented the buyers. Monica Lochmandy with Isleworth Realty represented the Stewart family trust.

Stewart and five others died on October 25, 1999, when the chartered jet they were on lost cabin pressure, incapacitating everyone on board. About four hours after it took off from Orlando on its way to Dallas, it crashed in a South Dakota field.

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Stewart was the winner of 11 PGA tour events including three majors, the last being just a few months before he died. On the final hole at the 1999 U.S. Open, he sank a dramatic 15-foot putt for a one-stroke victory.

A portrait based on this photo of Stewart cradling his 1999 U.S. Open championship trophy hung on display at the entrance to the private office.
A portrait based on this photo of Stewart cradling his 1999 U.S. Open championship trophy hung on display at the entrance to the private office. (CHRISTOPHER A. RECORD / Knight-Ridder Tribune)

On the course, he was known almost as much for his creative and colorful clothing as he was for his golf skills.

Tracey Stewart told Golf Digest she and Payne had just finished plans for the house on the day the plane crashed. She made a few changes to the design, but moved her family in the next year.

The interior is not nearly as colorful as the knickers, high socks, and driving hat Payne Stewart usually wore, but it is stylish with lots of wood and quality craftsmanship.

According to public records, the buyers are Jessica and Kurt O’Brien, who are moving from a house on the Butler Chain of Lakes to this one because it better fits their needs. Kurt O’Brien was the CEO of Simply Self Storage, which was acquired last December by Blackstone REIT for $1.2 billion.

“They were looking for something more private for their two young children who are aspiring to be professional wakeboarders,” Ziolkowski told GrowthSpotter. “They were focusing on wanting to have almost their own private lake for them to train on.”

Ziolkowski said the two have the skills and predicts they will be household names in the next decade.

This four-bedroom and five-bathroom home was perfect for them. It sits on more than two acres on Lake Bessie and has a dock, providing the perfect place for the kids to practice their craft.

Luxury brokerage Douglas Elliman is entering the Greater Orlando market and co-listing the 17,000-square-foot mansion with Isleworth Realty.

“[The buyers] saw this house, they liked it, and it spoke to them,” he said, adding others had already put in offers, but couldn’t seal the deal, so his clients were able to get the house.

The home has many unique features including a gift wrapping room and an office with a formal reception area and conference room overlooking the lake.

“The house has a massive garage underground and a movie theater. The rooms are oversized and everything is top of the line,” Ziolkowski explained, adding his clients will put their personality and personal touches into it. “They’ll make it even better.”

The indoor-outdoor pool area has a summer kitchen, fireplace, and waterslide.
The indoor-outdoor pool area has a summer kitchen, fireplace, and waterslide. (UNEEK Luxury Photography)

One part of the house that does not need much improving is the pool area, which is two stories with a fixed ceiling, but does feel enclosed.

“It is a very unique design and they pulled it off awesome. I felt like it was inside, but it had screens so it had the outdoor breeze. It is great for someone that doesn’t like to get sun, because it is shielded from the sun,” Ziolkowski said. “It was ingeniously designed and is a sight to behold when you’re there. It’s the signature piece of the home.”

Near the pool is an outdoor kitchen, fireplace, and waterslide. Between the pool and the lake is a putting green Payne Stewart never got to use.

“It was designed for a legend and he never got to live in it. It’s pretty tragic stuff,” Ziolkowski said “The family members that I met were just as nice as could be. I felt it tear at my heartstrings when I had to think about them packing to move from the home that they designed. It’s always the human element of this business and it varies from deal to deal. The people they handed off to couldn’t be a nicer family so it’s a win-win situation where everyone leaves happy.”

Have a tip about Central Florida development? Contact me at Newsroom@GrowthSpotter.com or (407) 420-6261. Follow GrowthSpotter on Facebook, Twitter and LinkedIn.

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