A quarter of a century after purchasing the house where legend has it that Oscar Hammerstein II penned lyrics for The Sound of Music, Brenda Isaac has put Hammerstein Highland House up for sale. The price tag for the six-bedroom, seven-bathroom property that sits on 17 acres of land in St James is US$1.65 million ($256.4 million).

Isaac’s first encounter with the property was as a guest. She had rented it to host a staff retreat when she was in the incentive travel business. Then she got the opportunity to own it.

“I sold my business at an early age and the broker who had rented the house to me sent me a message saying, ‘I know how much you love the Highland House and it’s on the market.’ Having been in the hospitality industry I figured I could do well by having a luxury rental villa — that’s what I’ve done with the Highland House for the past 25 years,” she told the Jamaica Observer.

She had help from loyal staff, including her now 73-year-old butler Karl Powell who has been with the property since he was 18, working with Dorothy Hammerstein. But it has still taken a toll on Isaac.

“I’m now 73 years old. I want to retire for real because having that house is like running a small boutique hotel. It’s a full-time job, 24/7. It doesn’t take that much of my time but I always have to be on call. I’m ready to slow down. That’s why I am putting the house on the market,” she said.

Isaac has fond memories of the property which, over the years, has welcomed a number of celebrities. Among them Academy award-winning actress Meryl Streep; British-American comedienne Tracey Ullman; American funk and soul group, the Commodores; along with owner of the Atlanta Falcons and co-founder of Home Depot, Arthur Blank.

However, Highland House had celebrities under its stately roofs long before Isaac bought it. It was built in the 1940s for English actress Gladys Cooper. Hammerstein and his wife Dorothy were the second owners, and they would retreat to the property when they needed a break from life in fast-paced New York. They would sometimes have well known names from the world of entertainment stop by for a visit.

When Hammerstein died his wife sold the property to his accountant, George Teichner. Isaac bought it from Teichner in 1999 and a year later she did extensive renovation of the property, however she preserved the essence of its romantic history. Over the years, she said, she has kept Hammerstein House in “good shape”.

Its six bedrooms each have an en suite bathroom and sitting area, and all the modern-day amenities one would expect in a vacation home can be found there.

“It’s been well-maintained because it is a guest villa — that requires constant maintenance, and upkeep, and freshening up, and keeping it going. When a guest comes there to stay you can’t have leaky pipes, or faucets that don’t work, or bathrooms that aren’t adequate. It’s in very, very good operating condition. It’s got a roof that’s less than five years old,” said the sprightly American.

Isaac wants whoever owns it next to treat it as lovingly as she did.

“I always thought the Hammerstein family might want to buy the house just because of the history. And I’ll tell you another idea that I have: I’ve always thought that one of the Marley boys, specifically Damian, would want that house because it would make the perfect recording studio,” she said, her voice going up an octave at the thought. “The whole bottom level could be a recording studio, and he could have his organic garden.”

Isaac knows just how fertile the land is because, for many years, she used seven acres to grow organic vegetables as part of her One Love Learning Foundation. She provided internships for students of Knockalva Agricultural School in Hanover, and they sold the produce to Round Hill Hotel.

“For seven years I ended up having this wonderful organisation that was providing jobs for youth. All of those proceeds from the sales were going back into hiring and training the interns to grow organically,” said Isaac.

The students also had an opportunity to interact with their peers in other branches of the foundation in the US and South Africa.

“Probably the most fruitful thing that came of my stay in the Highland House, or in Jamaica, was the success of the One Love Learning Foundation. But when COVID hit it brought an end to everything. The whole country was closed down for a while, and when an organic garden dies you have to start from ground zero to build it back. That’s about the time I decided I was going to dissolve and sell,” Isaac explained.

The area where the garden used to be is fully irrigated.

“We have rainwater harvesting off of the roof of my house, with a pump and pipes that go down to the garden to water the organic garden. We’ve got a big water tank where we catch rainwater. I even have a little tree house down there, where I housed my students, with an outdoor shower and a toilet facility,” said Isaac.

Also on the property is a three-bedroom, two-bathroom, self-contained apartment that was once used as staff quarters. There is also a yoga pavilion that Isaac used when she hosted wellness retreats. Competing with all the recollections she has of her guests are even fonder memories of the times she spent with her daughter and grandchildren on the property, nestled in the tranquil community called Content.

“I have wonderful neighbours and long relationships. There’s only about six houses up there in Content. We’re all very close so I’ve got a real sense of community in that area. You drive down a long driveway to get to the house and it’s very private,” said Isaac.

She will miss Highland House.

“The views from this house are breathtaking. It’s got good bones and, cosmetically, it’s an extraordinary house,” she said wistfully.