The owner of a run-down Honolulu estate once considered the largest private residence in America is seeking the city’s OK to restore and enhance the property as a family compound with three mansions and a private harbor.

Plans to renovate and enlarge the former Kaiser Estate in East Honolulu’s Portlock neighborhood are being considered by the Honolulu City Council. The plans first had to go through the initial steps of a regulatory environmental review, which the state Legislature imposed on exceptionally large home renovations or construction projects in 2012.

The estimated $16 million improvement plan for the 5.4-acre Portlock property is one of the first to fall under the heightened environmental review, which previously did not apply to single-family residences.

Evershine II LP, a company led by Hawaii-born entrepreneur Annie Chan, has been working on the renovation plan for more than a year.

It calls for building a new two-story residence with 20,000 square feet of living space, a guest wing, a cabana and a pool.

An existing 14,000-square-foot residence originally created mainly for boat storage also would be renovated, along with an adjacent staff house to which would be added a four-car garage and a pool.

Other pieces of the project include creating a third driveway onto the property, converting an electrical room into a wine cellar, maintaining a metal footbridge that provides public access over the mouth of the estate’s private harbor and repairing an existing sea wall, boat harbor walls and a shore-front saltwater pool.

Renovating the existing 12,350-square-foot main house on the property and adding a new four-car garage topped by a guest/staff house is also part of the plan up for City Council review, though this piece of the plan is nearly completed because it was permitted before the 2012 law was enacted.

Including driveway areas, the three-home mega-estate is to include parking for 57 cars.

EVERSHINE SAID the restored estate will be used by the extended Chan family.

“The three major residences are designed for the owner and the owner’s family,” Evershine said in an environmental assessment submitted to the state Office of Environmental Quality Control last year. “These renovations consist of exterior and interior upgrades and total rebuilding of those areas that have been left in an unsafe condition by the previous owners.”

Under the relatively new law, Evershine needs a special management area use permit, which puts special controls on development near shorelines. Single-family residences were previously excluded from SMAs, but that was changed by state lawmakers in 2012 to apply to homes with more than 7,500 square feet of living space.

The Chans’ residential SMA permit is believed to be the second one taken up, according to the Department of Planning and Permitting. More are expected, including one slated for an Aug. 3 hearing that pertains to a plan by Alexander & Baldwin Inc. to build three luxury duplex homes on a large waterfront lot at 4607 Kahala Ave.

TO COMPLY with the new regulatory review, Evershine applied to DPP for the permit and produced an environmental assessment last year. In April DPP held a public hearing at which a few neighboring residents expressed concerns, mainly about building height limits and trees blocking ocean views.

Kurt Mitchell, president and CEO of local design firm Kober Hanssen Mitchell Architects Inc., which represents the Chans, said at the meeting that they aren’t seeking to exceed height limits or other parameters of the city’s zoning code.

“We’ve stayed within everything that is allowed by residential zoning,” he said, according to a transcript.

One neighbor suggested that a Portlock community association has covenants that restrict use of a property to one home, but Mitchell said Kaiser, an industrial magnate who created Hawaii Kai, didn’t subject his own estate to the community association covenants.

Another issue was the seemingly long duration of the work and the construction noise that would accompany it.

“This has been going on for, what, three years?” Kay Brennan, a Portlock resident who lives across from the Chans’ property, asked during the hearing, according to a transcript. “How much longer is this going on? The drilling of the granite by the front gate goes on day and night. The back-up things go beep, beep, beep — 7 Sunday morning. Beep, beep, beep. This is going on and on.”

Mitchell responded that the SMA permit is partly to blame. “I mean, (the Chans are) as anxious as you are to get it over with,” he said. “You know, we did not expect that we would have to go through this until we found out in 2012 that we had to … go through a lengthy environmental process and then now through the SMA process.”

In May, DPP Director George Atta recommended approval of the permit to the City Council, which is now taking up the issue.

An initial hearing before the Council’s Zoning and Planning Committee took place May 19. But Councilman Trevor Ozawa, who represents the area, suggested that Evershine’s representative should have briefed Council members more fully prior to decision making.

AT A FOLLOW-UP hearing Wednesday, no one from the public testified, and the committee voted to advance the measure for a hearing before the full Council, which is likely to happen next month.

If the permit is granted, Evershine will breathe new life into the old Kaiser Estate, which has been in a state of decline for more than two decades.

Kaiser was a visionary industrialist whose businesses included development of highways, dams, cars, planes, health care insurer Kaiser Permanente, hotels and master-planned communities.

One of Kaiser’s communities was Hawaii Kai, which he began working on in the 1950s while semiretired. Nearby, on 7 acres of oceanfront land below Koko Head leased from Bishop Estate (now Kamehameha Schools), Kaiser built his own home in 1959 for $1 million. At the time the estate was regarded as the biggest privately owned oceanfront residential property in -Honolulu and the largest private residence in America.

After Kaiser died in 1967, the property was acquired by Monte and Alfred Goldman, renowned party-throwers and millionaire sons of an Oklahoma grocer who invented the shopping cart.

The estate changed hands again in 1988 when eccentric Japanese billionaire Genshiro Kawamoto bought it for $42.5 million, which at the time was described as the highest price paid for a private residence in America. What made Kawamoto’s purchase even more extraordinary was that the land still belonged to Bishop Estate.

Kawamoto talked about stately renovation plans but ended up giving the property back to Bishop Estate in 1994 after he bristled at the trust raising its land rent to $1 million a year. The trust also offered to sell the land to Kawamoto for $26 million, but he walked away instead.

After that, Bishop Estate struggled to sell the property during a depressed housing market.

CHAN AND her husband, Fred, set their sights on Kaiser’s former estate after earning a fortune in Silicon Valley’s semiconductor industry and deciding to make some real estate investments in Hawaii, where she was born and he attended college.

The couple bought a piece of the property — 2 acres containing the boathouse, harbor, a staff house and a greenhouse for $5 million in 1997 from Bishop Estate, which had divided the property into three “mini-estates” as a strategy to interest more buyers.

Three years later the Chans acquired an adjacent 3.5 acres containing the main house and pool for $9.6 million.

The third piece, which contained Kaiser’s old guesthouse on 2 acres, was sold to another buyer, who built a new mansion on the site that was resold in 2007 for $15.9 million.

Though the Chans made their initial fortune from the audio chip firm ESS Technology, which Fred Chan co-founded, they have also made big real estate deals, such as developing the Moana Pacific twin condominium towers in Kakaako and building a roughly 25,000-square-foot mansion in Silicon Valley that they sold for $100 million in 2011, two years after it was completed.

The Chans attempted to sell their Portlock property in 2008 for an eye-popping $80 million just as the real estate market went into a downturn.

Like Bishop Estate, the Chans also were willing to sell what they owned in pieces — 1.9 acres with the main house for $28 million, a 1.6-acre landscaped lot with tennis courts for $18 million, and 2 acres with the boathouse and harbor for $34 million.

Now the middle piece with the tennis area is slated for the new mansion.

If the permit is approved, Mitchell has estimated that construction would last about 18 months.