Bentley Estate on Star Island

Bentley Estate on August 24, 1962Bentley Estate on August 24, 1962

By the early 1920s, Miami and Miami Beach began to experience a population explosion based on the promise of beautiful year-round weather and the opulence of the tropics. This promise appealed to the ‘nouveau rich’ of the Gilded Age, particularly those who built their wealth in northern cities where unpredictable, and oftentimes harsh, winters, were reality for nearly half the year. During what became to be known as the Building Boom decade, South Florida witnessed the formation of neighborhoods and islands that appealed to wealthy northerners who bought lots and built their opulent, second homes in these newly developed quarters.

Calvin Bentley was one of those Gilded Age industrialists who discovered the benefits of wintering in South Florida for the first time in 1922. After two years of renting during his first winter stay, he and his wife, Irma, purchased lot 27 on Star Island to establish their winter roots on the newly developed upscale island. Having made his fortune as president of several Michigan-based companies, and possessing a sizable share of General Motors’ stock, Calvin spared no expense when he commissioned the design and construction of 27 Star Island. This is the story of the Bentley Estate from its construction in 1924 to present day.

Owosso Manufacturing Company

Owosso Manufacturing Plant in 1889

Figure 1: Owosso Manufacturing Plant in 1889

Calvin P Bentley was the oldest son of Alvin M. Bentley, who was president of the Owosso Carriage Company in Owosso, Michigan, when Calvin was born in 1883. A year later, in 1884, Alvin went to work for D. Thompson & Company, a manufacturer of farm tools, as the manager. In the Fall of 1886, Alvin bought out Thompson and renamed the company to the Owosso Tool Company, where they specialized in the manufacturing of hay rakes, tool handles, and other farm tools.

As the company grew and expanded its product offering, the name evolved to the Owosso Manufacturing Company. By 1889, the company branched out into millwork, producing a line of windows and wooden screen doors, and by the early 1910s, the firm acquired the Continental Screen Door Company of Detroit, Michigan, to solidify its market share for their millwork product line.

It was during this expansion period that Alvin put his son Calvin in charge of the millwork business. Given that he had grown up around the company, Calvin learned the intricacies of how Alvin liked to conduct business from an early age. Although he was only recently appointed to lead one of the company’s most profitable divisions, it was when his father passed away suddenly on October 5, 1917, at a sanitorium in Monrovia, California, when he was thrust into a senior leadership role for the entire enterprise. To add to the family tragedy, Calvin also lost his brother, Alvin Bentley Junior, as a casualty of World War I less than a year after his father passed, which left him not only the head of the family business, but also as the patriarch of the family. Calvin was thirty-four years old when he assumed the role of president of the Owosso Manufacturing Company.

Under Calvin’s direction, the manufacturing company continued to grow and thrive financially. By 1924, the Owosso Manufacturing Company was shipping one million window screens, four hundred and fifty thousand screen doors, and one hundred and eighty thousand snow shovels. However, it was the ‘Humpty Dumpty’ brand egg carriers that was their biggest seller and ultimately set the reputation and legacy of the company.

While the growth and profits of the manufacturing entity provided the Bentley’s a very comfortable living, Alvin’s friendship and business relationship with William Crapo Durant provided the family a different level of wealth, which helped Calvin keep Owosso Manufacturing in business during the difficult Great Depression years.

General Motors Connection

Portrait of William C. Durant

Figure 2: Portrait of William C. Durant

Given his start in the manufacture of horse-drawn carriages, Alvin Bentley developed a friendship and working relationship with William C. Durant, one of the co-founders of General Motors and Chevrolet. Durant founded the Durant-Dort Carriage Company in Flint, Michigan, in 1890, and built the company to become the largest manufacturer of horse-drawn carriages. Although skeptical about the future of automobiles, Durant assumed control over the Buick Motor Company on November 1, 1904, and under his leadership, made Buick the number one selling automobile in America. During this turnaround and based on his connection with Durant, Alvin Bentley invested in Buick and became a significant shareholder of the company.

In early 1908, Alvin convinced Durant to manufacture his Reliance heavy-duty trucks in Owosso by helping to secure a $30,000 municipal grant to help retrofit the old Owosso Carriage Company factory into a truck manufacturing plant. Durant agreed, put Alvin in charge of the operation, and Reliance began rolling trucks off the assembly line by the time General Motors was formed on September 16, 1908.

In 1909, General Motors, in effort to bring two different truck lines under the corporate umbrella, acquired Reliance Motor Trucks, making Alvin a significant shareholder of General Motors. Trucks continued to be assembled in the Owosso plant, now with the GM Truck label, until 1913 when General Motors closed the Owosso plant and consolidated all of their truck manufacturing to Pontiac, Michigan.

After Alvin passed away in 1917, Calvin inherited his father’s GM stock, and held onto it. Although many Owosso’s businesses failed during the Depression, Bentley’s large holdings of GM stock helped keep the Owosso Manufacturing Company afloat, allowing the company to remain profitable through the Second World War, when military contracts help reinvigorate the firm’s bottom line.

Palm Island Estate Constructed in 1924

Bentley Estate from Biscayne Bay

Figure 3: Bentley Estate from Biscayne Bay

During the height of success for the Owosso Manufacturing Company in the early 1920s, the Bentley’s began enjoying their wealth by wintering in South Florida beginning in the winter season of 1922. On June 11, 1924, the couple purchased a lot on Star Island and announced the construction of what became their permanent winter residence at 27 Star Island. Calvin hired Walter DeGarmo to design the residence, which was estimated to cost $50,000 at the time the building permit was filed.

The plans for the 18-room house included spacious hallways and living quarters, with ten of those rooms located on the first floor and the remaining eight located on the second level. The design also included four fireplaces throughout the residence, and a double-car garage attached to the main building.

The Miami tribune described the residence as follows:

“The Bentley home is a rather unique conception of the Spanish mode. The two wings of the home, connected on the waterfront side by a long living room, opening into a spacious patio, and the rear of the wings are connected with a balcony or covered runway, with antique wooden balustrade, making a second story connection. Both (wings) are finished in cream stucco with old tile roofing and bright blue trimmings.”

Having broken ground in June, the residence was completed rather quickly and ready for occupancy prior to the end of the year. The Bentleys returned from Owosso, Michigan, and moved into their new estate on December 27, 1924. While they split time between Michigan and Miami Beach, the Bentley’s owned and occupied the Star Island residence for more than five decades after constructing the home in 1924.

Calvin Bentley Investment in Community

Portrait of Calvin P. Bentley in 1962

Figure 4: Portrait of Calvin P. Bentley in 1962

The Star Island estate was more than just a winter retreat for the Bentleys. Calvin got involved in a number of civic organizations and business interests in the local community, and Irma was a very active participant in some of the most prominent garden clubs in South Florida.

One of the first investments Calvin made in the community was to purchase the lot (#28) adjacent to his property (#27), on Star Island for $28,500 on May 7, 1925. Regardless of one’s primary career, almost everyone with money was investing in South Florida real estate during the peak of the building boom, and Calvin was no different.

In May of 1929, Calvin was granted a permit to construct a store at 910 Lincoln Road for $15,000, although the actual cost of construction was later revealed as $20,000. The Antique Dome Shop, which sold antiques, jewelry, and old English silver, was the first business to lease this building when it opened in December, and remained a loyal tenant for many years. Today, the building, referred to as the Antique Dome building, still stands and is now leased by the AllSaints Apparel Shop.

In addition to his local investments, Calvin was also actively involved in several high profile social and civic organizations. He was a founding member and first chairman of the Surf Club when it opened in 1931, as well as a Vice President of Miami Beach’s Committee of 100.

In addition, Calvin was appointed to the board of directors for the First National Bank of Miami Beach in August of 1962. Bentley remained active in social and civic organizations in South Florida from his arrival in the 1920s until his death 1962. During his nearly forty years as a winter resident in South Florida, he became a leader and pillar of the community. He had an imprint and left a legacy during his time on Star Island.

Garden Club Showplace

Entrance to Bentley Estate on October 26, 1936

Figure 5: Entrance to Bentley Estate on October 26, 1936

As involved as Calvin was with civic and commercial organizations, Irma Bentley was just as involved with some of the most prominent garden clubs in South Florida. Her passion was cultivating her garden and advancing the objectives of garden clubs. She attended meetings, worked with Charles Torrey Simpson, and became an active member of the Little River, Riverside and Holleman Park garden clubs. Through the years, the Bentley’s hosted social events for fundraising and board of director elections at their Star Island residence.

Irma’s interest in gardens was not limited to her involvement with local clubs, but also to her own property. The Bentley residence became a ‘garden showplace’ and was one of three gardens shown to officials of the United States Parks and Forestry department when they met in Miami in 1950. The property contained one of the largest collections of tropical trees and blooming shrubs. The landscaping complemented the numerous pools, which featured cascading waterfalls and little foot bridges accented by the beautiful flowering plants and exotic saplings such as velvet, star and rose apple trees. The property also featured an oriental tea house and a specimen rock garden.

Casa Di Paolo in 1976

Casa Di Paolo in 2011

Figure 6: Casa Di Paolo in 2011

When Irma Bentley died on February 28, 1976, the residence would have a new owner for the first time in fifty-two years. Henry Paul purchased the residence for $250,000 as part of Irma Bentley’s estate sale and gave the home the name ‘Casa Di Paolo’, presumably a moniker based on his last name. The Paul family continued to maintain the landscaping as it was referred to as a “mini-Vizcaya” featuring two-acres of manicured lawns, tropical gardens, and hand-carved Italian sculptures in an ad placed in August of 1991.

Gloria Paul sold the home to Jannette Varela, president of Florida Equipment and Parts, a construction equipment leasing company, for $5.9 million in April of 1999. While the estate was Varela’s primary residence, she did occasionally lease the residence to celebrities for special short-term events. The home was the venue for a high-profile wedding in 2000, a four-day weekend rental to a hip-hop artist in 2004, and even a celebrity Super Bowl party in 2007.

One of the rental arrangements led to a high-profile dispute with the musician Ja Rule, a popular hip hop artist who rented the home for $16,000 for four days over the Memorial Day weekend in 2001. The rental led to a lawsuit where Varela claimed breach of contract given the condition that he left the property. The artist threw a party for over 600 people, and even recorded an episode of MTV Cribs where he claimed the home was his in the video. Despite receiving a $30,000 security deposit from the artist, the total damages far exceeded the total rental income plus deposit. Varela included MTV in their highly publicized lawsuit because the television network continued to air the Ja Rule MTV Crib’s episode despite being told that the home was not owned by the artist.

Several years later, Varela leased her home to a promoter called Ten Club, who planned to host three days of parties for Super Bowl weekend in February of 2007. The Thursday night kickoff party was scheduled to be hosted by Nick Lachey and Vanessa Minnillo, followed by a pool party on Friday evening, and the crescendo soiree on Saturday night featuring Paris Hilton, Hillary Duff, Mark Wahlberg, Ryan Seacrest, and DJ Nick Canon.

Given complaints filed by Varela’s neighbors, the City of Miami Beach stepped in and shut down the weekend of parties before they got started citing an ordinance that prohibited commercial use of private homes. There were one thousand ticket holders who paid $1,000 each for admittance to the weekend bash without a party to attend and plenty of questions for the Ten Club promoters.

A few years after the Super Bowl party debacle, Jeannette Varela sold the estate in August of 2011 for $10.75 million to John Jansheski, founder of Dentek Oral Care, under the corporate entity of Starboard Florida IV, LLC. While Varela may have had her issues with renting the home, she had to be pleased that she nearly doubled her money during her ten-year investment of Casa Di Paolo.

Residence Preserved and Moved in 2014

Casa Di Paolo Being Moved on December 10, 2014

Figure 7: Casa Di Paolo Being Moved on December 10, 2014

According to an article in the Miami Herald on December 7, 2014, John Jansheski listed 27 Star Island for sale after purchasing it, but changed his mind and decided to redevelop the property to construct his own home. Understanding the implications of requesting a demolition permit for an historic residence, Jansheski decided to move the original Bentley mansion from the center to the front of the property, and to construct a new, modern structure to merge with the historic home as a combination of two architectural eras. The combined structure would extend from where the historic home was moved, at the front of the property, to the waterfront, encompassing a large portion of the lot.

To prepare for the relocation of the Casa Di Paolo, the project team hired by Jansheski had to demolish later additions to the home including a free-standing garage and a residential wing added after 1925. Next, the remaining structure was lifted with a hydraulic jack, stabilized underneath with support beams, rotated ninety degrees, and then placed onto a truck and carefully moved from its original location to the front of the property (closer to the street). This took place on December 10, 2014.

The movement of the home and design of the new residence was provided by South African firm Stefan Antoni Olmesdahl Truen Architects. After the move was completed, Jansheski constructed a 20,000 square-foot modern residence behind the historic home which extends to the water front. Both old and new were seamlessly cobbled together on the original property of the historic home.

As Jansheski explained in an interview with CBS in 2014 when Casa Di Paolo was being moved, being able to join the best of architecture from 1924 with the best of modern architecture in 2022 provides an amazing marriage of eras (paraphrased). Given the complexities of any historic preservation effort, the merger of modern and classic architecture may provide a path to historic preservation when a property owner’s and a city’s preservation goals are at a crossroad.

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  • CBS4: “Historic Star Island Home Moved”
  • Website: Mitchell-Bentley Corporation
  • Owosso Times: “Alvin Bentley Obituary”, October 5, 1917.
  • Miami News: “$50,000 Home Permit Issued”, June 11, 1924.
  • Miami News: “Bentley Family Move In”, December 27, 1924.
  • Miami Tribune: “New Residences on Star Island”, January 7, 1925.
  • Miami Herald: “Permit Issued for $15,000 Store”, May 15, 1929.
  • Miami Herald: “Officers Installed at C.P. Bentley Home”, May 17, 1933.
  • Miami Herald: “Shown Second Time”, February 24, 1950.
  • Miami Herald: “Provided at Local & National Levels”, August 14, 1962.
  • Miami Herald: “Calvin P. Bentley Dies; A Founder of Surf Club”, September 11, 1964.
  • Miami Herald: “Mrs. Irma P. Bentley, Obit”, February 28, 1976.
  • Miami Herald: “Who Wants to Marry a Multimillionaire”, May 25, 2000.
  • Miami Herald: “Star Island Resident Says Rapper Abused Rented Home”, August 27, 2004.
  • Miami Herald: “Uninvited Guests Shut Down High-Priced Party”, February 3, 2007.
  • Miami Herald: “On posh Star Island, Moving a House, Not Razing It”, December 7, 2014.


  • Cover: Bentley Residence on August 24, 1962. Courtesy of Casey Piket.
  •  Figure 1: Owosso Manufacturing Plant in 1889. Courtesy of Shiawassee History website.
  • Figure 2: Portrait of William C. Durant. Courtesy of Wikipedia.
  • Figure 3: Bentley Estate from Biscayne Bay. Courtesy of Casey Piket.
  • Figure 4: Portrait of Calvin P. Bentley in 1962. Courtesy of Miami Herald.
  • Figure 5: Entrance to Bentley Estate on October 26, 1936. Courtesy of Miami-Dade Public Library, Romer Collection.
  • Figure 6: Casa Di Paolo in 2011. Courtesy of Zillow.
  • Figure 7: Casa Di Paolo Being Moved on December 10, 2014. Courtesy of Miami Herald.