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Orlando didn't have much of a skyline until the 1980s, when a building boom spawned the city's first real skyscrapers. Photo by Buzzy Movshow.

Our Town

Downtown Orlando, Windermere, Winter Garden and Winter Park

DOWNTOWN ORLANDO

Scarcely a week passes without another major condominium project-many boosted by controversial tax incentives-being announced for once-sleepy downtown Orlando. And as quickly as announcements are made, buyers swoop in and plunk down deposits.

In fact, more than 30 projects are either planned, under construction or recently finished. About 7,000 condominium units are on the way, along with six buildings encompassing 1.1 million square feet of office space.

And on the fringes of downtown, huge expansions at Florida Hospital and Orlando Regional Medical Center are under way while Florida A&M University's law school and a new federal courthouse have just been completed.

Remarkably, this rush of interest comes after years of apathy about downtown and its prospects as a desirable place to live, work and play. Just ask attorney William J. Sheaffer, who in the mid-1980s remodeled an old house on Central Boulevard and converted it to an office for his criminal law practice.

"We did it because it was close to the courthouse," says Sheaffer. "Beyond that, downtown didn't hold a whole lot of appeal. Not a lot to do, nowhere to go."

"It was like a ghost town down here back then," adds Carol Sheaffer, who manages her husband's practice. "There wasn't much going on even during business hours. And after that, forget about it."

Fast-forward to 2006, and it's a very different scene on Central Boulevard.

Just east of the Sheaffers' office, at the bustling mixed-use complex known as Thornton Park Central, the day begins when gourmet-trendy Central City Market opens for breakfast.

Next door, Shari Sushi Lounge attracts a glittery lunch and evening crowd while the spacious Urban Think! Bookstore offers in-the-know readers a gallery/bistro hangout.

And at the corner, trendy Hue remains one of the hottest dining spots in town, especially during its monthly "Disco Brunches," when the restaurant's self-serve Bloody Mary bar draws long lines and the retro sounds of Donna Summer fill the street.

And all that barely covers just one neighborhood in Orlando's dynamic downtown corridor.

In addition to all the new shops and markets, and an ever-changing firmament of nightclubs and restaurants, the city's central core has become one of the liveliest real estate markets in the region, attracting not only youngish, single career seekers who like to congregate where the action is, but also middle-aged professional couples who appreciate the convenience of a daily routine that doesn't depend on the vagaries of Central Florida traffic.

Of course, there are residential options downtown aside from new condominiums.

The charming old neighborhoods ringing the city have been gentrifying since the late 1980s. While Thornton Park is perhaps the highest-profile example, property values are also soaring in the city's other designated historic districts, including Lake Eola Heights, Lake Lawsona, Lake Cherokee and Lake Copeland.

As builders build and buyers buy, Mayor Buddy Dyer and others are looking for ways to boost downtown arts and entertainment options while enhancing pedestrian-friendly transportation systems and attracting a greater variety of businesses.

Everyone agrees that a downtown performing arts center, which Dyer has made a priority, would be a wonderful addition. But almost no one agrees on how such a project, which would cost at least $150 million, would be financed.

Still, Dyer has promised that ground will be broken by the end of his term, in 2008, and a committee of community movers and shakers is working to develop a plan.

Renovating or replacing the TD Waterhouse Centre, home to the NBA's Orlando Magic, is also on Dyer's to-do list, as is an overhaul of the Citrus Bowl, currently home to the University of Central Florida Golden Knights and two annual bowl match-ups.

But the so-called "O-rena" would cost $70 million to renovate, while a new facility would cost perhaps four times that much. And the Citrus Bowl upgrade, which would cost at least $150 million, has become an iffy proposition since UCF officials finalized plans to start building an on-campus stadium this year.

Despite these hurdles, the foundation for enormous change downtown is already in place, says Downtown Development Board executive director Frank Billingsley.

"There's a trend across America of more and more people moving into downtowns, and we have a very desirable and pleasant downtown infrastructure in place," says Billingsley, who points to the city's brick streets, urban lakes and architectural variety.

"Our downtown is a neighborhood where you can feel very connected to friends, family and community. It's a much richer experience, living in an urban environment where you can feel connected to the pulse of the community."

WINDERMERE

Nestled among the spring-fed Butler Chain of Lakes, the cozy Town of Windermere, population 2,300, has emerged as the region's new-money address of choice.

With Lake Butler on the west, Lake Down on the east and Lake Bessie on the southeast, Windermere is a verdant peninsula where 317 of 837 homes are on the water. Winderemere-or at least the area surrounding it-is also home to some of Central Florida's most upscale new communities.

But although they advertise Windermere addresses, most of these ritzy developments aren't technically in Windermere, much to the chagrin of some locals who object to the alleged misappropriation of the town's proud name.

In fact, Windermere itself is just 689 acres, and consists largely of a laid-back retail district with a few mom-and-pop stores and a scattering of older homes lining sandy streets. Those streets remain unpaved, to discourage traffic and prevent runoff from damaging the Butler Chain, which consists of eight pristine lakes connected by a canal system.

The lakes attracted one of Windermere's first investors, Joseph Hill Scott, an English clergyman who in 1885 bought 150 acres. Scott's son, Stanley, homesteaded the property and supposedly named it after Lake Windermere in England.

The railroad connected Windermere and Kissimmee in 1889, but freezes in 1894 and 1895 destroyed the town's citrus industry. Little changed until 1910, when a pair of Ohio investors named D.H. Johnson and J. Calvin Palmer bought all the land they could piece together and formed the Windermere Improvement Company for the purpose of developing it.

The pair promoted "Beautiful Lakes of Pure Spring Water" and aimed their marketing at moneyed Northerners.

Although few who live here want to see the town change significantly, Windermere city officials are making concessions to the growth surrounding it. The town recently completed a $2.5 million public works project-the largest in its history-to revamp the downtown area, bricking three blocks of Main and Frontage streets, expanding parking lots, replacing stop signs with roundabouts and generally upgrading its appearance.

And developer Kevin Azzouz, who in 2003 purchased much of the property in the business district, has talked about creating a town center, much to the consternation of residents who like downtown's unpretentious combination of shabby and chic.

WINTER GARDEN

It was 1857 when Becky Roper Stafford's great-great-grandfather first glimpsed Lake Apopka. W.C. Roper was riding through the backwoods of west Orlando" target="_blank">Orange County on horseback, seeking a place to build a home for his family waiting back in Merriwether County, Ga.

Roper bought 600 acres along the shore, between present-day Winter Garden and Oakland, and returned a year later with his wife and 10 children. The ambitious settler operated a sawmill, a gristmill, a sugar mill and a cotton gin. Later he built a tannery for making shoes, and served as Orlando" target="_blank">Orange County's superintendent of schools from 1873 to 1877.

Fast-forward to the 1920s, when Roper's son Frank planted the area's first orange trees, marking the humble beginnings of an industry that would sustain and define Winter Garden, which had been incorporated in 1903, for the next six decades.

Winter Garden remained an idyllic small town throughout World War II and into the 1950s and 1960s. Far removed from Orlando, which was about to be reshaped by the advent of Disney World, the city remained self-sufficient and unpretentious.

"Winter Garden was the quintessential vibrant small town," says Stafford. "We had the distinction of being the only town with two train depots, because it was such a busy shipping community with fresh fruit going all over the world."

Fast-forward again to the 1980s, when devastating freezes destroyed thousands of acres of citrus. Roper Growers Cooperative, Heller Brothers and Louis Dreyfus Citrus eventually recovered. But as growers regrouped or retreated, once-bustling downtown Winter Garden became a virtual ghost town.

Concurrently developers began buying up decimated groves for new homes, creating new subdivisions seemingly overnight. But most of the residential growth, and the retail growth that followed, was outside the city, which made Winter Garden proper even more of an anachronism.

Then came a brilliant project called Rails to Trails, through which abandoned rail beds across the country were converted into hiking and biking trails.

The popular West Orange Trail passed directly through Winter Garden, thus converting the all-but-forgotten city into an oasis for thousands of ready-to-spend strollers. In fact, city officials estimate that the trail is responsible for generating about 50,000 downtown visitors per month.

And most are charmed by what they see. In 2001 the tired downtown district underwent a facelift. Brick streets were restored, old buildings were remodeled, and Centennial Fountain, saluting the city's citrus-growing heritage, was constructed.

Today locals and outlanders gather at Choctaw Willie's in the reopened Edgewater Hotel for barbecue, collard greens and sweet tea. Across the street, Moon Cricket Café serves eclectic cuisine and an array of micro-brewed beers. Winter Garden Pizza Factory is all about pasta, fresh pies and family fun.

Proprietor-owned shops, like JR's Attic, Downtown Herb Shoppe and Every Little Girl's Dream, are thriving. But you'll still find a wonderfully cluttered hardware store that sells farming supplies, serving as a reminder that this town's quaintness isn't contrived.

And locals proudly note that Winter Garden features two historical museums open seven days a week. There's the Central Florida Railroad Museum and the Heritage Museum, both housed in restored depots. History buffs may also stroll around the city and view such landmarks as the 1860s-era Beulah Baptist Church.

And redevelopment is on a roll: Stafford is hard at work with the Winter Garden Heritage Foundation to renovate the historic Garden Theater on Plant Street, which will become a 300-seat performing arts center.

While the old downtown is re-emerging as a force to be reckoned with, several miles south a 1.15-million-square-foot open-air mall called Winter Garden Village at Fowler Groves is set to open next July.

There are more than 40 new home communities currently under way within Winter Garden's corporate limits. And the city plans to annex a large tract of mostly undeveloped land from its western boundary south of Florida's Turnpike to the Orlando" target="_blank">Lake County line. The tract contains 1,300 developable acres that could eventually contain 3,600 homes.

To the south of downtown, along C.R. 535 and S.R. 545, communities totaling 25,000 homes are expected to be built where citrus groves once flourished.

The biggest of the new developments is Horizon West, a 38,000-acre master-planned community that has been in the planning stages for a decade. At buildout, its two villages-Bridgewater and Lakeside-will contain nearly 18,000 homes.

The first neighborhood is Independence, located in the Bridgewater village and developed by Transeastern Properties. The 1,342-acre project will encompass 2,415 homes, a 5,300-square-foot clubhouse, two town centers, three schools, two lakes and 600 acres of parks and preservation areas.

Horizon West developers and builders, worried that a lack of schools and roads could slow the project, have proposed two novel plans to keep things rolling.

First, a homebuilding consortium has offered to lend Orlando" target="_blank">Orange County Public Schools $32 million to build a middle school two years ahead of schedule-and to pay $2.9 million in fees and interest until the loans can be paid off.

Second, Grosse Pointe Development Company is paying close to $6 million to develop a connector road to link Fiquette Road to the Horizon West Town Center and C.R. 545.

Further opening up the area to development will be an extension of S.R. 429, which eventually will stretch from Apopka to I-4 just west of Walt Disney World.

WINTER PARK

Once a haven for artists, writers and some of the most influential families in the country, Winter Park was promoted in the late 1800s as a refuge for "the cultured and wealthy." Those early boosters would almost certainly be pleased to see how it all turned out.

Today, the city is home to 70 parks and nearly as many oak trees (20,000) as residents (24,090). Its eight square miles encompass lovely old homes, an upscale shopping district, a prestigious liberal arts college, a plethora of galleries and museums and street signs that admonish motorists to "drive with extraordinary care."

The heart of Winter Park is Park Avenue, stretching 10 blocks and boasting more than 100 shops, from upscale national retailers to one-of-a-kind boutiques. The Avenue, as locals call it, is a European-inspired thoroughfare featuring hidden courtyards, sidewalk cafés and charming Central Park facing the storefronts.

In addition, the downtown shopping district has begun to spread west on New England Avenue as developer Dan Bellows builds posh apartments and retail stores in previously blighted areas.

On the south end of Park Avenue is the Charles Hosmer Morse Museum of American Art, showcasing the world's largest collection of Tiffany glass. Each Christmas a set of priceless, holiday-themed Tiffany windows are moved to Central Park, where they're displayed as part of the city's seasonal festivities.

Several blocks farther west is Winter Park Village, a red-hot retail and entertainment center on U.S. 17-92. New condominiums are available in the Village, which attracts a generally younger crowd than Park Avenue and has emerged as one of Central Florida's most popular see-and-be-seen destinations.

Year-round the city is alive with festivals and special events, from the Sidewalk Art Festival, drawing more than 250,000 guests each spring, to the Exotic Car Show and assorted celebrations in Central Park.

On the shores of Lake Virginia, beautiful Rollins College, the oldest institution of higher education in Florida and one of the top-rated private liberal arts colleges in the country, is home to the Cornell Fine Arts Museum and the internationally renowned Bach Festival Choir.

Incongruous as it may sound, Winter Park also hosts a Saturday morning Farmers' Market, where visitors can buy everything from fresh produce to houseplants and crafts.

Although the city was essentially built out decades ago, several infill projects offer new homes in older neighborhoods. The largest new single-family home development is Windsong, carved from heavily forested lakefront property once owned by the estate of philanthropists Hugh McKean and his wife, Jeanette Genius McKean.

The property adjacent to Windsong, where Glenridge Middle School once stood, is being incorporated into the development despite the objections of residents who had hoped the city-owned land could become a park. Forty homes are planned for the 16-acre site.

Still, high-end condos account for most new residential construction in Winter Park. More than 500 apartments, condos and hotel rooms are either under construction or moving through the approval process. Naturally, some of those projects are causing controversy.

Approval of the four-story Carlisle on the northwest corner of Central Park was the catalyst that mobilized residents who opposed such projects as being at odds with the city's village-style ambiance. But business owners and younger residents have also spoken out, mostly in favor of new development.

To see Winter Park as it should be seen, shell out five bucks and take a guided tour along the Winter Park Chain of Lakes. Scenic Boat Tours, headquartered at Dinky Dock near Rollins College, has been cruising these canals since 1938, offering regular folks a chance to peek into the back yards of the rich and occasionally famous.


DOWNTOWN'S BOOM

Following is a list of major projects either planned, under way or recently completed in downtown Orlando.

Camden Orange Court: Four-story apartment complex with office and retail space at the 600 block of North Orange Avenue. Construction is scheduled soon.

Capital Plaza III: Condominium and office complex with hotel, retail, and restaurant, southeast corner of Rosalind and Pine Street. Not yet started.

Corinthian Place: Five-story condominium complex with office and retail space, southwest corner of Washington Street and Division Avenue. Not yet started.

Dynetech Center: 30-story apartment complex with office and retail space, corner of Magnolia Avenue and Washington Street. Dynetech Corp. will have its international headquarters in the building. Construction soon.

Eola & Church: Twin 12-story buildings with apartments, office and retail space. Starts second quarter of 2006.

Eola South: Four-story condominium project, southeast corner of South Eola Drive and Central Boulevard. Recently completed.

55 West: 32-story condominium and retail center with Church Street Market entertainment complex on Church Street, between Orange and Garland Avenues.

North Orange: 35-story condominium complex with a six-story professional office building and retail space at 759 N. Orange Ave. Not yet started.

Orlando City Place: Six phased buildings ranging from five stories to two 40-story towers including residential and hotel condominiums, retail, office and restaurant space at 304 W. Colonial. Not yet started.

Orlando Palace Towers: 34-story apartment complex and 37-story condo complex with retail and restaurants, east of Radisson Hotel between North Orange Avenue and South Ivanhoe Boulevard. Starts first quarter of 2006.

Osceola Brownstones: Three-story, 26-unit townhouse development at 310 S. Osceola Ave. Recently completed.

Paramount on Lake Eola: 16-story condo complex with Publix grocery store, and office space, 400 block of East Central Boulevard. Starts first quarter of 2006.

Premier Trade Plaza: 13- and 17-story office complex, 27-story condominium complex with retail space and a movie theater, 101 S. Orange Ave. Under construction.

Presidential Tower: 41-story condominium complex with retail on the first floor, between Garland, Gertrude, Jefferson, and Washington streets. Starts first quarter of 2006.

Ridgely Manor: 39-story condo complex with office and retail space, southwest intersection of Livingston and Rosalind, Magnolia and Palmetto. Not yet started.

Star Tower: 18-story condo complex with office and retail space, 421 E. Jackson. Under construction.

The Ivanhoe: Twin 37-story apartment towers with retail, southeast corner of Orange Avenue and Marks Street. Not yet started.

The Jackson: Nine-story condo complex, 521 E. Jackson. Under construction.

The Monarch: 23-story condo complex with retail, 300 E. South St. Starts second quarter of 2006.

The Sanctuary: 18-story condo complex with office and retail space, 100 S. Eola Drive. Under construction.

The Vue at Lake Eola: 35-story condo and retail complex, 426 E. Central Blvd. Under construction.

Thornton Commons: 16- and 20-story condo complex with retail at Church, Mariposa, Eola and Osceola Drive. Starts third quarter 2006.

305 S. Eola Dr.: Twin 12-story apartment complex on two corners of Church Street and Eola Drive. Under construction.

Tradition Towers: Twin 37-story towers with condos, office and retail space, 150 E. Central Blvd. Connecting "sky bridge" will house University Club. Starts first quarter of 2006.

217 N. Eola: 15-story condo complex. Under construction.