Ocala, Florida

By  Mike Miller  Updated November 20, 2023

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+ active adult 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 actively being developed by Colen Built Development, 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 Kenneth 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 was the late E.L. Strickland, who was named Rancher of the Year by the Florida Cattlemen's Association, and earned the ranch the Environmental Stewardship award.

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, 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, Colen Built Development, 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
  • 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
  • Billiard Hall
  • Archery Field
  • Softball Field
  • Community Centers with Pools
  • Dog Parks
  • Golf Shops
  • Horseshoe Pits
  • Hobby Buildings
  • Pickleball Courts
  • Picnic Pavilions
  • R/C Flying Field, R/C Car Track, And Drone Course
  • 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 Lifelong Learning Center and its classrooms as well as other businesses.

The large Circle Square Cultural Center is a theater style auditorium that seats 930.  It is an ideal setting for concerts, galas, plays, and conventions.

The Cultural Center has brought in premier entertainers including Willie Nelson, Kansas, Air Supply, and Kevin Costner & Modern West.

Circle Square Cultural CenterCircle Square Cultural Center

Tribute concerts are also 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 Circle Square Commons is open not just to OTOW residents, but the general public as well.  They have weekly live entertainment, markets, art and craft shows, and more.

The map above is On Top of the World Communities.  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 started by the Colen Family Trust Foundation, providing top notch instruction to residents of OTOW and the general public.

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.


The developer of On Top of the World, Colen Built Development, took their expertise of master planned 55+ communities and created an all-ages single family master planned community.

Then new community, maned Calesa Township, is located just north of On Top of the World and began in 2020.  Its name is Calesa Township. It will eventually have 5,000 homes on about 1,500 acres.

It has a tuition free K-8 public charter school recently opened in 2022, and is home to the new Florida Aquatics Swimming and Training aquatic center, FAST, 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.


Appleton Museum of Art, 4333 E Silver Springs Blvd, Ocala, FL 34470, (352) 291-4455. One of the best cultural spots in Ocala, the Museum of Art showcases both modern and classic pieces across several different areas of the art world. Populated by a mix of European, American, Asian, African, and contemporary art, it's a place where visitors can spend hours lost in thought and admiration. The architectural excellence of the building itself enhances the overall experience, promising a rich and heartening visit.

Silver Springs State Park, 5656 E Silver Springs Blvd, Ocala FL 34470, (352) 261-5840. This is where nature truly shines in Ocala. Beyond the iconic glass-bottom boat tours that reveal underwater wildlife in the crystal-clear springs, the park has beautiful hiking trails and picnic spots. A great place to explore, you'll enjoy reconnecting with Florida's authentic flora and fauna.

Ocala National Forest, 40929 State Road 19, Ocala, FL 34470, (352) 669-3153. If the state park isn't enough, you have an entire national forest waiting for exploration just outside the city. Ocala National Forest offers abundant wildlife sightings, pristine springs for swimming, and hundreds of miles of walking and biking trails. It's a perfect getaway for those who love the outdoors.

Don Garlits Museum of Drag Racing, 13700 SW 16th AVE, Ocala, FL 34473, (352) 245-8661. A trip to this museum is an excellent way to spend an afternoon. Whether you're a petrolhead or just interested in the history of drag racing, there's plenty to admire among the 300+ race cars on display.

Gypsy Gold Horse Farm, 12501 SW 8th Ave, Ocala, FL 34473, (352) 307-3777. You can't visit Ocala, the 'Horse Capital of the World', without seeing some thoroughbred horses. And what better way to do so than to tour the Gypsy Gold Horse Farm? Here, you'll see stunningly beautiful and unique Gypsy Vanner breed horses, first originated by the Gypsies of Great Britain.

Brick City Adventure Park, 1211 SE 22nd Rd, Ocala, FL 34471, (352) 671-8560. There's a 'something for everyone' type of environment at Brick City Adventure Park. Disc golf, walking trails, picnic pavilions, fishing, and so many other exciting things await you. And you wouldn't want to miss out on their equestrian events, which are both fascinating and thrilling.

Market Street at Heath Brook, 4414 SW College Rd #952, Ocala, FL 34474, (352) 237-6871. Experience shopping and dining in a lively setting. This shopping area houses an array of retail stores alongside a mixture of delightful restaurants. Whether you're looking for a unique gift or a delectable meal, you're sure to find it here.

Ocala Civic Theatre, 4337 E Silver Springs Blvd, Ocala, FL 34470, (352) 236-2274. Experience insightful, entertaining performances at the Ocala Civic Theatre. Known for well-crafted plays and musicals, the theatre contributes significantly to Ocala's cultural scene.

Ocala Downtown Square, historic downtown, Ocala, FL 34470. Spend time exploring Ocala Downtown Square, an epitome of Ocala's cultural heritage. Enjoy its array of quaint shops, savory restaurants, and historical sites. It's certainly worth a stop to enjoy the local flavor of this city at a designated National Register Historic District.

Ocala Ghost Walks & Historical Tours, 56 SE 1st Avenue, Ocala, FL 34471, (352) 690-7933. For a bit of the extraordinary, embark on the Ocala Ghost Walks. Discover fascinating stories of spirits and strange happenings across this historic city. It's definitely a distinctive experience, not for the faint-hearted.


Our Facebook page has more than 130,000 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.