When Oaks Bayside, the first of The Oaks Club’s subdivisions, was developed in the early 1980s, it was touted as an elite luxury community of million-dollar homes that offered seclusion, privacy and the caché of being unique and special. Located in Osprey just north of Historic Spanish Point, it had the benefit of being one of the most picturesque spots on Florida’s west coast.
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The Oaks took its name from the winter home of Chicago socialite Bertha Potter Palmer, who came to the area in 1910 and purchased thousands of acres for cattle ranching, citrus groves and real estate development. She converted a two-story hunting lodge on Little Sarasota Bay into a 31-room mansion for herself and called it “The Oaks.” The house is no longer exists; only the reflecting pool remains.
Of the four neighborhoods that comprise the current Oaks Club, The Oaks Bayside perhaps best reflects Bertha Palmer’s lavish tastes and eye for beauty. First developed by South Carolina builder Rodney Propps (subsequent developers included the Arvida Corporation and local businessman Piero Rivolta), it combined idyllic surroundings with memorable architecture.
The 135 estate homes all back onto either one of three scenic lakes, a large nature preserve or the bay. Sumptuous foliage throughout features tall palms and majestic oaks bedecked with Spanish moss.
Wildlife abounds, including egrets, osprey, eagles, rabbits, red foxes and bobcats.
Noted Tampa architect Bo MacEwen — MacEwen Drive on the golf-course side of The Oaks is named after him — modeled his designs on one of his earlier projects, John’s Island in Vero Beach.
“He was a very classically oriented architect,” says Sarasota architect Clifford Scholz, then a partner in MacEwen’s firm. “The idea was to create something that Sarasota didn’t have at the time.”
When Scholz arrived to manage the development, the area was so overgrown that he had to use a car with four-wheel drive to explore it.
“It took us 20 minutes to get to the water from U.S. 41,” he recalls.
At the spot of Bertha Palmer’s original residence, “the reflecting pool was facing in a direction the engineers didn’t want, so we turned it 90 degrees and rebuilt it,” Scholz says.
After designing the bayside entrance gates, they built homes for the initial investors along with some spec houses. They also constructed an administration building and a magnificent, 40,000-square foot clubhouse on the east side of the Tamiami Trail.
The Georgian architectural style harks back to 18th-century England and pre-revolutionary America. “It has classical Greek proportions but with Florida flair, connecting the indoors and outdoors,” Scholz explains.
As a result, many of the homes in The Oaks Bayside evoke the look and opulence of Southern plantations or European chateaus. The 6,263-square-foot mansion (with 968-square-foot guest house) at 95 Osprey Point Drive is one example. It is exquisitely detailed throughout, from custom millwork on walls, ceilings and floors to hand-carved wooden doors and marble and stone finishes. The owners bought the lot next door and added a three-car garage and guest apartment with full kitchen upstairs. An outdoor terrace and an upper deck overlooking one of the lakes both run the full length of the house.
“It’s a big home begging for a family with kids,” says Michael Moulton, the listing agent with Michel Saunders & Co. He also mentions that the asking price was just reduced to $2.2 million.
Moulton likes The Oaks Bayside for its beauty and style. “You drive in and you feel like you’re in such a classy neighborhood,” he says. “The yards are perfectly maintained, and the houses look immaculate.”
Most of the homes are primary residences, even if the owners go elsewhere for the summer. But the makeup of the community has changed since its early days. “There are now 300 kids living in The Oaks, not just older retirees,” Moulton says.
A big part of the community’s appeal comes from the two championship golf courses and the clubhouse. Every owner in The Oaks Club is required to have at least a social membership. The cost is $40,000.
At the same time, nearby amenities include restaurants, shopping and movie theaters at the Westfield Sarasota Square Mall, the Potter Park YMCA and Pine View School for the Gifted.
“The town has grown to The Oaks since the ’80s and ’90s, when it seemed off the beaten track,” says Moulton.
Considering its history and unique splendor, The Oaks Bayside is surprisingly affordable. The 15 real estate transactions during the past year ran the gamut from $471,419 to $2.8 million.
Currently, 23 listings are active with three pending, ranging in price from $433,300 to $3.9 million.
“It is a beautiful place to be,” says Moulton.
