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Jim Smith's deals with a developer came as the Pinellas appraiser struggled financially.

Money was tight for Pinellas County Property Appraiser Jim Smith in 1994. A divorce had left him with no property, big debts and two children to support.

Then two real estate transactions brightened his future - thanks to a prominent developer.

Smith bought one of the last slices of vacant land in Tarpon Woods, a golf course community in northeastern Pinellas, for $15,000.

His down payment: $100.

The seller was a corporation headed by Lloyd Ferrentino, who developed Tarpon Woods in the 1970s. The corporation loaned Smith almost the entire purchase price.

Two months later, another corporation led by Ferrentino sold Smith a two-bedroom Tarpon Woods condominium. Again, the corporation held the mortgage while Smith put down $100.

Smith sold the condo a few years later for a modest profit. But he kept his 1.5 acres of land, hoping to build a secluded home amid foliage and deer.

"In the middle of all this populated county is a little mecca,'' he said last week. "I thought, 'God, I love it.' ''

But Smith never built his sylvan getaway. Last month he sold the land to Pinellas County for $225,000, almost four times its previous taxable value.

That deal now lies at the crux of a grand jury investigation.

Did the county overpay? Did Smith get special treatment? How much acreage is buildable?

Even Smith's own appraisers have varied their estimates.

Now, Pinellas officials are hiring lawyers and facing unwelcome questions.

It's a far cry from the optimism of 13 years ago, when Jim Smith stopped at a For Sale sign, turned his car off Tarpon Woods Boulevard and headed into the trees.

Remaining parcel

Tarpon Woods, with a slew of single-family homes and condos, emerged from a large tract of wetlands and woods east of Lake Tarpon.

Its southern boundary was largely built out by the early 1990s, except for an oddball 1.5-acre slice between Tarpon Woods Boulevard and a tonier subdivision to the south. Brooker Creek ran through the lot, making it prone to flooding.

The primary developer was Ferrentino, a Long Island native who had built and sold Pinellas homes since the 1950s. His projects included the Starkey Ranch and Bardmoor Country Club.

Sometimes, his work intersected with public policy.

In 1983, Pinellas County bought 1,500 acres of Tarpon Woods land for $7.6-million. An audit called the price excessive and faulted the county for relying on only one outside appraisal.

That year, Tarpon Woods and four other golf courses sued then-Property Appraiser Ron Schultz, claiming he had misapplied an assessment formula and hiked their tax bill by 400 percent. A judge agreed with the golf courses.

Now 79 and retired, Ferrentino declined to comment.

Bills pile up

In 1994, property appraiser Smith was struggling with the financial fallout of divorcing his second wife, court records show.

His young children lived with him half the time. He had to pay child support and alimony. She kept the home; he had to pay off $45,000 of joint debts. His only assets were his state retirement plan and a 1990 Nissan 300Z.

He tried to bolster his income with multilevel sales ventures, but they fizzled. One company he worked for was deemed a pyramid scheme and shut down by the state.

Smith went looking for property, he said last week, because his kids shared a bedroom in his Tarpon Woods rental condo and he wanted something better.

His gaze fell on a For Sale sign he had passed dozens of times. It was the old, leftover slice of Tarpon Woods land.

From the road, the land looks like a narrow band of trees. But behind the trees and over a drainage ditch, the lot widens.

Brooker Creek, cutting through the property, connects with conservation land on both the north and south. Inhabitants include deer, alligators and catfish.

Smith said he called real estate agent Jim Nobles, who told him a group of investors had installed the driveway and planned a stilt house on the property's southeastern edge.

County records confirm that such a site plan was approved in 1990. No building permit was issued, but the approval showed a homesite was possible.

Nobles said the investors would sell "for what they had into it,'' Smith said. "They were all going to go their way and be happy. It was a flat market.''

He paid $15,000.

Who these investors might have been is unclear. Earl Michaels, architect for the 1990 site plan, said he can't remember his clients' identities.

The land's legal owner was Tarpon Woods Golf and Tennis Club Inc. As president, Ferrentino deeded the lot to Smith, records show. The corporation also took back a $14,900 mortgage; Smith paid only $100 up front, plus $618.45 in closing costs.

His monthly payment: $105.

Smith said he doesn't recall Ferrentino playing any role in the deal - just Nobles, the real estate agent.

Nobles, who sold many Tarpon Woods properties, is Ferrentino's brother-in-law. Nobles said he couldn't remember the Smith deal: "I wasn't that involved.''

Two months later, Smith purchased a 1,304-square-foot condo from Tarpon Woods Development Inc., with Ferrentino as president.

The price was $47,500. Again, Smith put only $100 down. Smith says he doesn't remember Ferrentino being part of the condo deal, just Nobles.

Nobles said he was not the agent when Smith bought the condo, but agreed he was the agent when Smith resold it 29 months later for $55,000.

Did Smith ever worry about the appearance of buying land from a developer under such terms?

Not for a minute, he said. The real estate market was flat. The owners couldn't find other buyers. The land would be expensive to develop and difficult to resell.

Though Ferrentino was once prominent in Pinellas real estate, "he was retired, he was unloading things,'' Smith said. "All Lloyd did was play cards and golf.''

Low ground, big dream

Smith's dream home in the woods would be 3,100 square feet with a two-story deck. Concrete "step-footers'' would raise the house to the same level as neighboring houses in a gated community, 100 or so feet to the south.

Those lots, at least 6 to 8 feet higher than Smith's, sold for about $100,000 in the early 1990s, a few years before Smith bought his for $15,000.

Pinellas County approved a site plan for Smith in 1997. Because of water issues, the footprint was big enough for only one house.

"They wouldn't let me touch anything else,'' Smith said.

By then he had started seeing Circuit Judge Catherine Harlan, whom he married in 1997. She wanted no part of Tarpon Woods.

"She said, 'If you think I'm driving 45 minutes back and forth to work, you are crazy,' '' Smith said.

He never took out a building permit and his authorization expired. But he didn't sell. He and Harlan might still build after they retired, he said.

County steps in

In 2004, Smith and Harlan separated.

By then, storms had left debris in Brooker Creek. County crews entered Smith's land without permission to clean up and dig a trench for drainage.

Trees were removed. Whether storms or county workers were to blame is open to debate. Regardless, condos to the east became visible.

Early this year, Smith complained that the work "devastated'' the site. He demanded that the county make good.

Smith said he would have been happy if the county had planted trees. Instead, it commissioned an independent appraisal, fast-tracked the sale and bought the land on June 29 for $225,000.

An uproar ensued when the St. Petersburg Times noted that in 2006, Smith's office had pegged the taxable value at $59,400.

Had the country grossly overpaid Smith? Did his office cut him a tax break? Or was there some other explanation?

A key issue is how much of the land is buildable.

Through 1993, the property appraiser's office designated the entire parcel as "submerged land'' with a taxable value of $1,100 to $1,200.

Then, in 1994, the year Smith bought it, his office determined that 0.47 acres was vacant land, not submerged. The following year that figure dropped to 0.23 acres.

Smith and his chief appraiser, Ron Anderson, said they have no idea why those designations changed.

"I don't get involved in that process,'' Smith said. Several employees have a role, he said. "There is not going to be any game playing.''

This spring, as county officials considered buying the property, they hired an independent appraiser who valued it at $250,000. That was based on 1.03 acres of uplands - an off-the-cuff estimate by a county environmental consultant. That consultant recommended a wetlands survey, but the county declined.

The independent appraiser calculated that the land was worth $5.60 a square foot, based on comparable sales. Had that appraisal calculated the uplands at 0.23 acres - as Smith's office did - then the independent appraisal would have come in at $56,105.

Both the 1990 and 1997 site plans approved by the county restricted construction to about a quarter of an acre.

Still, Smith says there's no real contradiction. His office's $59,400 assessment was valid, he said. But $225,000 was a bargain for county officials, given potential legal bills had he sued.

But what public official wants to sue and sock taxpayers with damages and legal bills?

Not the property appraiser, Smith acknowledged last week.

"I didn't want to do that.''

Times researchers Mary Mellstrom and Carolyn Edds contributed to this report. Jonathan Abel can be reached at (727) 445-4157 or at Stephen Nohlgren can be reached at (727) 893-8442 or at