Annapolis treasures its old buildings the way other cities love their sports teams. So residents watched with dread as a five-alarm fire tore through three late 19th-century buildings in the heart of Main Street -- not just at the thought of losing them, but at the possible fight over restoring or replacing them.

Friday night's fire was under control shortly before midnight, and all three buildings remained standing yesterday. But after fire inspectors and structural engineers spent the day assessing the damage, city officials condemned the center building, which houses Zachary's Jewelers, and ordered that its three-story white cinder-block facade be demolished this morning.

"The structural engineer looked at it and said that the facade is just very dangerous," city spokeswoman Jan Hardesty said. The other two buildings, she said, were declared salvageable.

Fire inspectors continued to look for the cause of the fire last night.

Harvey Blonder, who owns the building occupied by Zachary's as well as one of the other buildings and has a long-term lease on the third, said the damage could run into millions of dollars.

Blonder vowed to rebuild quickly.

"I've spoken to the mayor, and the city has a structural engineer on the way to look at it," said Blonder, who also owns two other Main Street businesses. "I think everybody wants to work together, and hopefully we can get it rebuilt right away."

But the city's love for historic architecture can also mean lengthy debate among city officials, historic preservationists and business owners. The site of two century-old downtown buildings that burned eight years ago remains an empty lot.

Of the buildings damaged Friday, Zachary's, at 122 Main St., appeared hardest hit. Windows on the first floor were shattered. From the street, the interior appeared blackened and strewed with charred debris.

The shop's owner, Steve Samaras, said none of his employees was injured when the blaze erupted at 7:51 p.m. Most of the merchandise, especially the high-end diamond pieces, was saved. "The inventory seems to be pretty much intact, thankfully," Samaras said.

As was true of most shops downtown, the store was open late for the post-Thanksgiving sales rush when the fire started.

The Candy Factory, at 118 Main, and Main Street Ice Cream, at 128 Main, also were significantly damaged. The three buildings, each three stories, are attached, making access difficult for firefighters.

A fourth building, A.L. Goodies General Store, at 112 Main, suffered smoke damage. Famous for its free fudge samples, it remained open yesterday selling Annapolis souvenirs and T-shirts as the smell of smoke permeated the air.

The last major fire on Main Street, on Dec. 9, 1997, destroyed two century-old buildings just blocks away from the site of Friday's blaze. The lot still sits vacant, with just a patch of grass and a wooden fence after long battles over the use of the property, including a dispute over whether a 99-year-old brick wall left standing after the fire should be preserved. A storm finally settled the matter, weakening the wall so much that it was deemed unsafe and torn down.

"I hope we've learned from the lessons of that fire eight years ago," said Gregory A. Stiverson, president of the Historic Annapolis Foundation, "and that we'll be able to work together to make sure that these three buildings are repaired as quickly as possible."

The historic district's status as a National Historic Landmark and the city's zoning codes complicate rebuilding projects. To do even seemingly minor repairs, building owners must submit their plans to the city's Historic Preservation Commission, which then holds a public hearing to review them, said William Schmickle, chairman of the seven-person commission. "Part of what we want is that historic fabrics should be preserved wherever possible. That's the bricks, the mortars and other building materials."

City department heads were meeting yesterday and were to meet again today to begin smoothing the way for reconstruction to begin, Mayor Ellen Moyer said.

"We want to move quickly to have this done," Moyer said. "We don't want a wall to hold us up for eight years."

The scene continued to draw large crowds yesterday, as the street in front of the buildings remained taped off and fire inspectors combed through the darkened interiors.

"It's horrible to see a part of your city go down like that," said Vicky Robertson, a longtime Annapolis resident. "These buildings have been here a long time."

None of the buildings had sprinkler systems in the upper floors, an issue that has concerned city officials for years with many of downtown's older buildings. Without such fire-protection measures, the upper stories are limited to storage use and cannot be occupied. The city passed a measure last year offering building owners low-interest loans to install sprinklers, but the application process is just beginning.

When downtown sidewalks were being re-bricked in the mid-1990s, several building owners turned down a chance to run additional underground piping up their structures for sprinkler connections, Moyer said.

"It was amazing that about one-third of the property owners did not take the option to run the pipes," she said. "Something like this is testament for the need so we don't see this kind of destruction."

Part of what makes Annapolis special is that it has largely been spared from many of the devastating fires that struck other East Coast cities, Stiverson said. But that's also what makes the loss of one building so difficult to bear.

"Most other towns, if you lose three buildings, you lose three buildings," he said. "In Annapolis, you have that context of 300 years of buildings that make the streetscape so varied, so when you lose a part of that, it's a particular loss."

The city has an inventory listing the building dates of most Annapolis structures, but those files were not available yesterday.

Main Street Ice Cream appeared to be the most historically significant, said City Administrator Robert D. Agee. Fire ripped through the sloped red-tin roof and gutted at least one of the window eaves angling out from the building, which dates perhaps to as early as the 1860s.

The Georgian structure used to be two buildings, said Howard Smith, 72, whose family has owned the building since 1905. His grandfather used to run a meat shop in it, he said. Smith said he expected plenty of hurdles but pledged to restore it.

"I'm sure Historic Annapolis will have a lot of say, and everything will have to be brought up to code," Smith said. "There's no doubt I'm starting a long, tangled road."

Capital City Colonials tour guide David Smith checks out Friday's fire damage on Main Street.The five-alarm fire in historic Annapolis began just before 8 p.m. Friday. A fire official said that a full block of Main Street was evacuated.Harvey Blonder, who owns two of the damaged buildings, said the damage could run into millions of dollars. But he added that he wants to rebuild quickly.