[9][10] Harold Schwartz, a Michigan businessman, began selling land tracts via mail order in The Villages area in the 1960s.

[11][12] Stuck with considerable portions of Florida land, in the early 1970s, Schwartz and Tarrson began the development of a mobile home park, Orange Blossom Gardens, in the northwestern corner of Lake County.

Morse noted that the thriving retirement communities (such as Del Webb's Sun City developments) offered numerous well-maintained amenities to the residents.

Schwartz began to buy large tracts of land in nearby Sumter and Marion counties for future expansion.

[citation needed] In 2013, the IRS ruled that $426 million in bonds were not tax-free since the bureaucracy running The Villages could not be considered a real government.

In the spring of 2017, The Villages announced a planned acquisition of 2,600 acres north and south of County Road 470 along the east side of Florida's Turnpike for future development.

[20] In January 2024, RCLCO Real Estate Advisors named The Villages the top-selling planned community for the eleventh consecutive year, with 3,029 new homes sold in 2023, a decrease of 23 percent over 2022.

[21] A declaration of restrictions has been created for each neighborhood, which regulates the design and operational aspects, such as landscaping, repairs and maintenance, placement of satellite dishes, hedges, etc.

The committee, which consists of Villages residents, reviews and approves alterations and modifications to the properties and homes built by the developer.

[38] According to the data from the Consumer Financial Protection Bureau, women purchased 468 homes while men bought 406; this means approved mortgages for women as a percentage of approved mortgages for men was 115%, making The Villages the highest rate of the 400 metropolitan areas in the United States.

The main business areas are the 500,000-square-foot town centers that feature a mixture of retailers, restaurants, entertainment, and service providers.

One historian wrote, "The Villages' faux history gives a patina of stability and continuity to a highly volatile region and stage of life.

[63] Activities available include bocce, horseshoe, and shuffleboard courts, swimming, billiards, tennis, pickleball, theatrical and musical productions, and fitness.

[68] Just before the 2016 United States Senate election in Florida, Rubio stopped off at the temporary Republican Headquarters established at Lake Sumter Landing in The Villages.

[81] In October 2004, George W. Bush became the first president to visit The Villages with a rally in the new Lake Sumter Landing Market Square with approximately 20,000 supporters.

[82] A White House official announced that President Trump would be visiting the Sharon L. Morse Performing Arts Center on August 6, 2019, to speak about Medicare at an invitation-only event.

[83] Due to the separate mass shootings in El Paso, Texas, and in Dayton, Ohio, Trump postponed the visit.

[85] From there, Trump traveled via motorcade to the Sharon L. Morse Performing Arts Center where he delivered an hour-long speech about expanding Medicare eligibility to an invitation-only audience of roughly 1,000 supporters.

At the close of the event, Trump signed an executive order to expand private insurance options for seniors under Medicare.

[88][89] On October 10, 2020, Vice President Mike Pence spoke before a crowd of approximately 1,100 supporters in Brownwood Paddock Square.

Topics covered by Pence included support for veterans, the economy and job creation, the administration's response to the COVID-19 pandemic, and NASA funding.

[90] On October 23, 2020, Trump visited The Villages, appearing with Governor Ron DeSantis and former Florida attorney general Pam Bondi.

[95] In the fall of 2017, The Villages launched The Enrichment Academy with more than 140 fee-based, lifelong learning, noncredit courses on topics such as scuba diving, literature, philosophy and psychology, culinary arts, technology, foreign language, photography, and more.

The Chitty Chatty Bridge, crossing Florida State Road 44 near Rohan Recreation Center and Lake Deaton Plaza, opened to traffic in October 2020.

[105] The Villages developers operate a trolley-style bus tour of the community from the sales and information center at The Market Square in Lake Sumter Landing.

In early 2018, The Villages was chosen for a pilot program offering autonomous taxis in the area of Lake Sumter Landing.

The technology-rich Ford Fusion Hybrid and Chrysler Pacifica minivan taxis will be operated by Voyage Auto, a startup company from San Jose, California.

[107] The effort to present a "fanciful past" for The Villages through fictionalized plaques and building details demonstrates "the role that history plays in retirement migration.

"[50][111] Critics have negatively compared this presentation to the approach of Disney theme parks, claiming that the plaques generally do not address ethnic minorities or conflict.

[52] Amanda Brian argued in her book, "The Villages' 'history' whitewashes Florida's past and celebrates a straightforward tale of economic growth.