Over 75 Years
Longer than most retirement communities have existed
About On Top of the World
Built by a Family. For Yours.
On Top of the World Communities has been family owned and operated since 1947, longer than most retirement communities have existed. This is the story of how it came to be, and why it's still unlike anything else in Florida.
See how it started
A Track Record You Can Trust
The proof is in the details
75 years. 50,000 homes. Ranked the most popular active-adult community in Florida. Some things speak for themselves.
50,000 Homes Built
For residents who chose to spend their best years here
Ranked #1
The Most Popular Active Adult Communities by 55places.
Two Generations. One Vision.
A family legacy
Sidney Colen founded On Top of the World in 1947 with a belief that retirement should be the beginning of the best chapter of your life. His son, Kenneth Colen, grew up by his side, learning every part of the business from the ground up. Kenneth has led On Top of the World as President since 1981, carrying his father's vision forward for over four decades.
Explore how we build
In His Words
Our mission
“This Company has always stood for quality, value, moral obligation and sustainable development practices. We have never undertaken the development of anything or any community unless we believed there would be a redeeming value. Money has never been the motivation or the purpose of our existence. We have always believed keenly that service and human values are greater than mere development. We affect the lives of people and we affect their lives for good.“
— Sydney Colen, Founder, On Top of the World
The history of On Top of the World
75+ Years of Milestones
From a single community in Clearwater to 13,000 acres in Ocala, this is how On Top of the World grew into becoming Florida's most celebrated 55+ active adult community.
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On Top of the World is Founded
Sidney Colen founded On Top of the World Communities in Clearwater, Florida with a simple belief that retirement should be the beginning of the best chapter of your life, not the end of anything. The first community proved the concept worked.
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Circle Square Ranch Purchased
Sidney Colen purchased 13,000 acres of working cattle ranch land in Ocala, Florida, known as Circle Square Ranch. What started as open Florida ranchland would become the future home of On Top of the World, one of the state’s most celebrated active adult communities.
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Kenneth Colen Becomes President
Kenneth Colen grew up in the business, literally by his father’s side. He has led On Top of the World Communities as President since 1981, bringing over 40 years of dedicated leadership to a company his father built from nothing.
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Development Begins in Ocala
Construction begins on what will become one of Florida’s largest and most celebrated 55+ communities. Three neighborhoods, three golf courses, and 175+ clubs would follow.
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Environmental Stewardship Award
Circle Square Ranch was recognized for outstanding environmental practices. 418 acres of conservation land protected, reflecting the family’s long-term commitment to the land they’ve called home for decades.
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Community of the Year
Recognized by 55Places.com as Community of the Year two consecutive years and ranked among America’s 50 Best Master-Planned Communities, a distinction earned by the people who live here as much as the people who built it.
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Still Building. Still Family Owned.
Three neighborhoods, 13,000 acres, 175+ clubs, and three championship golf courses, all guided by the same family that started it all. On Top of the World remains completely debt-free and privately owned, answerable only to its residents.
Still considering your options? We’re here to help you find the right fit.
Three days, two nights, a private guest home, and the opportunity to experience all that our community has to offer. All for just $99 per couple. Experience the lifestyle firsthand and see if On Top of the World feels like home.
