Ocala, Florida

By  Mike Miller  Updated May 11, 2022

On Top of the World Things To Do, Lodging, Dining, & Real Estate At End Of Article

On Top of the World in Ocala, Florida is a large master planned 55+ retirement community located on State Road 200 about 11 miles west of downtown Ocala.

It is about 28 miles north of its closest lifestyle competitor, The Villages Florida.

On Top of the World Communities Entrance SignOn Top of the World Communities Entrance Sign

Residents and other locals refer to the community as OTOW.

On Top of the World is in an ongoing process of being developed by On Top of the World Communities, LLC.  It is the second Florida development with this name.

On Top Of The World in Clearwater broke ground in 1960 and by the 1990s was completed and has since become a popular west coast Florida retirement community.


On Top of the World Communities, LLC was founded in 1947 by the late Sidney Colen, who began his career in development and construction in Pinellas County. 

He built dozens of condominiums and residential subdivisions, and also created the Town of Kenneth City in the St. Petersburg area and the first On Top of the World in Clearwater.

Kenneth City was actually named for his son, Kenneth Colen, in 1957 when he was 6 years old.

In 1975 he extended his operations to Marion County by buying the Circle Square Ranch, a historic working cattle ranch west of Ocala.

Kenneth Colen, was involved in the family business during most of its existence, and in 1981 became head of the organization. 

Sidney Colen passed away at age 90 in 2009 in Clearwater, Florida and his son Kenneth still runs the organization.


The Circle Square Ranch was a 12,900 acre cattle ranch established by James Norris in the 1940s and owned by the Norris Cattle Company.  

Circle Square RanchCircle Square Ranch

Sidney Colen purchased the ranch in 1975 and began to put together a development like almost no other in the United States.

He decided early on to develop his new community while carefully preserving much of the natural land and working operations of the ranch.

Equestrian Statue at On Top of the WorldEquestrian Statue at On Top of the World

A large portion of the original ranch remains in operation although surrounded by the neighborhoods and homes of On Top of the World.


The Circle Square Ranch is still in operation with 1,200 cattle grazing on 9,000 acres. 

The long time manager is E.L. Strickland, who was named Rancher of the Year by the Florida Cattlemen's Association.

E. L. Strickland and FriendE. L. Strickland and Friend
Courtesy of Environmental Stewardship Award

Many of the residents of On Top of the World are fond of "their cows" and are proud to be part of this working operation.

The ranch also has abundant wildlife such as burrowing owls and gopher tortoises, and other endangered or threatened Florida animals who have a happy home here among the cows and people.


The Circle Square Ranch Master Association, Inc. is a homeowners association composed of the individual neighborhood associations in the community as well as the developer, On Top of the World Communities, LLC.

On Top of the World Cottage Series HomeOn Top of the World Cottage Series Home
Architectural Rendering from On Top of the World Communities, LLC

There are 15 neighborhoods in several gated communities in On Top of the World, each with a different ambience and catering to different interests and lifestyles.  These are:

  • On Top of the World Central
  • Candler Hills
  • Indigo East
  • Windsor
  • Avalon
  • Providence
  • Williamsburg
  • Friendship Colony
  • Friendship Park
  • Friendship Village
  • Crescent Ridge
  • Americana Village
  • Crescent Green
  • Renaissance Park
  • Longleaf Ridge
  • Stone Creek
  • Weybourne Landing

In some of the communities you do not actually own your lot;  you instead have a 99 year land lease.  In others you have fee simple ownership of the property.

There are three golf courses in On Top of the World:

  • Candler Hills Golf Course, semi-private
  • The Links Golf Course, private
  • The Tortoise and the Hare Golf Course, private
Lodge at Candler HillsLodge at Candler Hills

The community is laid out with miles of trails and numerous recreational facilities such as:

  • Fitness Centers
  • Tennis Courts
  • Bocce Ball Courts
  • Community Centers
  • Dog Parks
  • Golf Shops
  • Horseshoe Pits
  • Hobby Buildings
  • Pickleball Courts
  • Picnic Pavilions
  • Radio Control Flying
  • Driving Ranges

Many OTOW residents have golf carts and are able to visit almost everything in the community without ever cranking up their car.

Circle Square Commons

Circle Square Commons is on the northern side of On Top of the World and is home to Master the Possibilities and its classrooms as well as other offices involved in managing the community.

The large Circle Square Cultural Center is a theater style auditorium that seats 830.  It is the venue for many musical events and plays.

Circle Square Cultural CenterCircle Square Cultural Center

Tribute concerts are a popular attraction among the active senior population of On Top of the World.  You may see tribute concerts by lookalikes for Elvis, Kiss, Van Halen, and many more.

The square is open not just to OTOW residents, but locals.  They have frequent dances, markets, art and craft shows, and more.

The map above is from On Top of the World Communities, LLC.  If you click on the image of the map you will be taken to a PDF map than can be zoomed in and out for a closer look at the community layout.

There is a large shopping center anchored by a Publix at one of the main entrances to On Top of the World.  The center has a nice collection of restaurants and shops popular with the locals.


Sidney Colen realized that most retirees have spent their lives doing something they were good at.  He thought it was a shame they just retired and stopped working.

He wanted them to be able to share their knowledge with younger people, stay engaged, and be mentors to others.

Having traveled all over the state for many years, I have never seen anything to match the Master the Possibilities program at On Top of the World.

It is a not for profit adult learning and instruction organization funded by On Top of the World Communities.

It provides top notch instruction to residents of OTOW and others.

Click on the cover of see a PDF catalog of their recent course offerings.  

You can learn all about cameras, painting, language, legal, economics, creative writing, local and national politics, history...the list is endless.

They offer as many as 900 classes each semester attended by more than 25,000 students. 

I have first hand experience as a "teacher" in some cases and as a "student" in others.  Both were very rewarding to me.


Development of a new community within On Top of the World began in 2020.  Its name is Calesa Township, and will eventually have 5,000 homes on about 1,500 acres.

Unlike the other 55+ communities in On Top of the World, Calesa Township will have families of all ages.

It will have a tuition free K-8 charter school, and will be home to the new Florida Aquatics and Training aquatic center with indoor and outdoor pools.


Sholom Park is located near the north side of On Top of the World at 7110 SW 80th Avenue.  It was inspired by Sidney and Ina Colen, developers of On Top of the World.

Sholom Park Water FountainSholom Park Water Fountain

The Colens wanted to create a quiet park which people could visit to enjoy some natural peace and quiet in a busy world.

It is a private park the opened in 2004 that focuses on native Florida plants that need little maintenance. 

The native vegetation is punctuated by many flowers, perennials, annuals, and meadows, and woods.  There are paved walkways that provide an easy way to explore the park.

The park is also a popular wedding venue and quiet space for other community activities.


Our Facebook page has more than 123,638 followers who love off the beaten path Florida: towns, tourist attractions, maps, lodging, food, festivals, scenic road trips, day trips, history, culture, nostalgia, and more.  We post articles every day.  Please check it out and if you like it, we would appreciate a "like" from you.