The History of The Villages Florida
In 1959, the pastureland that now hosts The Villages, Florida, sold for about $150 an acre. Back then, Florida was largely thought of as coastal beaches—few looked toward the quiet, rolling land in the center of the state. But visionaries like Walt Disney and Chicago advertiser Harold Schwartz saw something others didn’t: opportunity. While Disney was acquiring land for theme parks, Schwartz was buying thousands of acres for future development. Today, a premier golf-front lot in The Villages might cost $100,000, while a commercial acre fetches $350,000. What happened in between tells the story of The Villages.
Over the following decades, more than 2,000 acres of untouched land would be transformed into homesites, roadways, lakes, recreation centers, golf courses, and town centers. The Villages now exceeds all but two incorporated cities in the counties it spans. Its residents, mostly retirees, have created a political bloc so influential that it regularly attracts attention from state and national leaders.
Despite its long backstory, nearly 90% of The Villages’ growth came in just the last decade—largely under the direction of Harold Schwartz’s family. In the 1950s and ’60s, Schwartz and his son Gary Morse ran a direct-mail advertising business in Chicago, selling land in warm climates like Florida, New Mexico, and the Caribbean to buyers across the U.S. and England.
At that time, Schwartz wasn’t thinking about retirement communities. He was managing radio stations with partner Teo Bichara (helping launch Wolfman Jack’s career), overseeing U.S. stations in Denver and Salt Lake City (with help from his other children, Richard and Kay), manufacturing cameras in Japan for Sears, and investing in real estate in Las Vegas and St. Louis.
Then regulations made mail-order land sales illegal by the late 1960s. In the 1970s, his business partner Al Tarrson decided to slow down and relocate to Fort Lauderdale. Taking inspiration from mobile home communities like Mid-Florida Lakes, Tarrson used unsold land to begin a new project called Orange Blossom Gardens—a modest mobile home park.
While Harold stayed in Chicago and Gary moved to Michigan to run a restaurant and nightclub, Tarrson began developing in Florida. But progress was slow. After ten years, Orange Blossom Gardens had fewer than 400 homes. In the early ’80s, Tarrson wanted out. Schwartz and Morse, however, saw potential.
Drawing inspiration from Del Webb’s successful Sun City in Arizona, Schwartz knew it wasn’t just affordability—it was lifestyle that drew retirees. Although Sun City’s Florida experiment had failed, Schwartz believed a retirement town in Central Florida could thrive. In 1983, he bought out Tarrson, with one condition: Gary had to move to Florida to manage the project directly.
On March 1, 1983, Gary Morse arrived in Lady Lake and began personally overseeing the community’s rebirth. His wife, Sharon, redesigned homes and community spaces to reflect a more appealing aesthetic. They infused pride and care into Orange Blossom Gardens, beginning what would become one of Florida’s most famous developments.
That April, Gary wagered a bet with his Michigan friend John Parker: they would sell 100 homes that year. At the time, only three had sold. Parker joined the effort by July, overseeing construction. They ended 1983 with 99 homes sold—one short of their goal. Still, Morse sent a memo to Harold saying they were short $100,000 for the September budget. Harold replied: “Keep selling—and build one for me.”
By 1985, The Villages had become Harold’s primary focus and permanent home. For his 75th birthday at Mission Inn, friends and family—including granddaughter Jennifer—came together. Jennifer soon joined the home sales team.
At that time, Orange Blossom Gardens lacked amenities. The closest full-service towns were eight miles away. 1985 brought major change: a nine-hole golf course, new pools, and tennis courts. Gary and Sharon’s son Mark left Michigan to open the community’s first commercial center, La Plaza Grande, attracting medical offices, a bank, and local shops. When investors didn’t step up, they launched businesses themselves—gas station, restaurant, convenience store, and more.
Between 1986 and 1987, new golf courses and recreational facilities opened, including the Silverlake Club. They also upgraded the quality of manufactured homes by designing and building their own. Inspired by manufacturing in Japan, they constructed a cutting-edge drywall production plant in Florida. Eventually, it transitioned to build roof trusses for site-built homes.
In 1988, they faced a big decision. Orange Blossom Gardens was outgrowing its land, and to grow further, they needed to cross U.S. Highway 27/441 into Sumter County. This required working with multiple counties and the state’s Development of Regional Impact (DRI) process. Harold Schwartz, nearing 80, decided they couldn’t stop halfway.
They turned their old offices into recreation centers and built the “Pink Palace,” a striking new facility across the highway. This move ushered in major developments: the community’s first bowling alley, supermarket, shopping center, and site-built homes. Most importantly, this was when the name “The Villages” was officially adopted.
Harold stressed that a real town needs neighborhoods—offering choices for various budgets and housing preferences. New areas like Village Del Mar, El Cortez, and Mira Mesa launched across the highway. Older areas were renamed to fit the concept: Orange Blossom Gardens, Silver Lake, and Country Club Hills became part of The Villages of Lady Lake.
The early 1990s brought an explosion of activity. The Chula Vista Course opened with a new restaurant and recreation complex. The Villages’ first local bank was created. The La Hacienda Hotel welcomed guests, and the 18-hole Hacienda Hills Championship Course was completed in just six months. Golf legend Chi Chi Rodriguez helped open the course in 1991.
Richard Schwartz left broadcasting to run the new golf facility. Around the same time, Gary and Sharon’s daughter Tracy and her husband Don moved from Michigan to manage shopping centers. Publix joined the growing list of businesses in the area.
Although Harold said he’d slow down by age 80, he didn’t. On his 80th birthday, Gary surprised him with a jet full of friends and family, flying to Cancun for a party with old business partner Teo Bichara.
To fulfill environmental requirements under DRI, The Villages launched a Wildlife Habitat and Agricultural Division, led by Paul McDowell—Gary’s childhood friend. The operation balanced nature preserves with active farmland, and today maintains one of Florida’s top Holstein herds alongside habitat for protected species like gopher tortoises and kestrels.
In 1993, new recreational and retail additions accelerated the dream. The second executive golf course opened. Sunbelt Utilities was purchased and converted to a public utility, allowing better service for Lady Lake and beyond. A sports pool complex and fast food outlets followed.
Still, the community was split by the highway. Golf carts couldn’t legally cross, so the family built a $1 million overpass. Dedicated to State Rep. Everett Kelly, it symbolized the unification of The Villages.
Governance was complex. Some Villagers lived in unincorporated Lake County, others within Lady Lake. A 1984 referendum to consolidate failed. Later attempts also failed, as residents were wary of higher taxes. As growth pushed into Sumter County, even more political coordination was needed, but no consensus emerged for creating a single municipality.
Despite divided governance, The Villages thrived. Still, something was missing: a downtown. Schwartz declared, “You can’t have a town without a downtown.” Clermont had one. So did Tavares and Mount Dora. The Villages, now larger than all three, did not.
In 1994, the Schwartz family began designing an old-fashioned town square. They hired designers who had worked on Universal Studios to make it feel authentic. Schwartz donated $1 million for the plaza. That spring, it opened with a grand celebration, complete with a bronze statue of Harold himself.
An entire city block of vintage-style commercial buildings was constructed. Offices moved into these structures. The old admin buildings were repurposed as the La Hacienda Recreation Center. A church was planned in collaboration with Rev. Steve Raulerson.
By the early 1990s, the first Winn-Dixie opened, and The Villages boasted 3 golf courses, 4 restaurants, and just over 8,000 residents. This period marked a key point in local development history. You can explore more on our historical photos, read about early restaurants in The Villages, or learn how the golf courses evolved through resident discussions and archives. From that foundation, the expansion accelerated dramatically. Today, The Villages spans more than 89 square miles across Lake, Marion, and Sumter counties, with a population exceeding 153,000.
The community now includes over 750 miles of private roads, 711 holes of golf, 2,700 social clubs, 109 recreation centers, 108 swimming pools, 15 softball fields, polo fields, 235 pickleball courts, and more than 105,000 golf carts. There are now 118 individual “Villages” neighborhoods—and counting.
Economically, The Villages is a powerhouse. Over $300 million is spent annually at its restaurants and retail centers. The average household income exceeds $73,000, with a median home value of $346,900. Over 75% of residents live in The Villages full-time, and around half pay cash for their homes. The community also hosts the largest population of veterans outside a military base.
With over 6 million square feet of commercial space, The Villages supports 100+ restaurants, regional shopping centers, health providers, and major brands such as Target, Walmart, Sprouts, and Fresh Market. A new Costco has also broken ground. Entertainment options include a performing arts center with over 1,000 seats, several movie theaters, and miles of golf cart-accessible paths.
And the growth isn’t slowing. The Villages is now widely recognized as the largest and most successful retirement community in the world—a thriving example of how vision, leadership, and lifestyle can shape an enduring legacy in Central Florida.
