I Spent the Day at On Top of The World — Here's What I Learned

Quick Take: On Top of The World is a massive 43-year-old golf-cart-friendly community in Ocala with 10,000 homes give or take. Prices range from $159,900 resales to $449,500+ new builds. The unique leasehold deed model means no yard work ever. With $524/month HOA covering exterior maintenance and three golf courses, it's ideal for active retirees who want amenities without upkeep.

📞 Ready to tour On Top of The World? Call us at 407.970.0958 or email hello@explore55plus.com

Quick Facts

First Impressions of On Top of The World

Full disclosure: this is actually my second visit to On Top of The World. We filmed here a few weeks ago and... let's just say we didn't get permission first. Got a little flak for that one.

But the community reached out, we cleared the air, and this time I'm walking through with Kelly, a sales specialist who sells the new construction homes. Much better experience with an actual tour guide.

The first thing that hits you about On Top of The World is the scale. This isn't some new community trying to establish itself - it's 43 years old with multiple neighborhoods, each with its own personality. When Kelly spread out the community map, I could see the different sections: Candler Hills, Balfour, Waybourne Landing, Indigo East, Longleaf Ridge.

What I Saw Walking Through On Top of The World

Kelly started by showing me the map and pointing out where they're actively building. "Waybourne Landing is now built out completely," she told me. "So is Indigo East. The only place inside On Top of The World Central, other than Candler Hills that they're building is over here in Longleaf Ridge."

But here's what impressed me: they're not done expanding. They're adding a fourth golf course - an executive 9-hole in Waybourne Landing. And they're building a brand new fitness center in Candler Hills that should open first quarter of next year.

"This one here is going to be a little different," Kelly explained about the new fitness center. "We'll have spin classes, cycle classes, which we don't have behind the gates right now within the community."

The existing fitness center at the Arbors already has state-of-the-art equipment with independent upper body machines. Kelly mentioned she worked there and appreciated that the equipment is designed so you can address muscle imbalances. That level of detail matters when you're in your 60s and 70s.

The Golf Cart Lifestyle is Real Here

I've toured a lot of golf cart communities, but On Top of The World takes it seriously. Kelly walked me through their whole cart path system on the map.

"We are a great golf cart community," she said. "And what I mean by that is that we use golf carts for transportation. We're probably about 15% of our community population that are golfers."

That stat surprised me. Most people assume golf cart = golfer, but here it's just how you get around. Kelly explained that many families become "a one car and a golf cart family because no one gets abandoned."

Three shopping plazas are accessible by golf cart, and Kelly kept calling them "all the staples of life." She wasn't exaggerating. We drove by the plazas and I saw:

• Post office
• Hardware store
• Big Lots (Caitlin, who was also on the tour, was very excited about this)
• Publix in one plaza
• Walmart Neighborhood Market in another
• Hair and nail salons
• Medical offices (dental, eyes, ears, health clinics)
• Starbucks

And here's the kicker: "We're getting Home Depot just outside the gate," Kelly told me. "Very soon. So you can go to Home Depot on your golf cart soon."

There's even a service road that keeps you off Highway 200 but lets you access all the plazas. Golf cart parking at every plaza. They've also got Fifth Third Bank that just opened, and an HCA emergency room and hospital going in.

On Top of The World Amenities: Pool, Clubhouse & More

The amenities here are layered. Kelly mentioned they have three championship golf courses, with that fourth executive course coming. We drove past Candler Hills golf course, which just reopened after being closed for renovation in May.

"We closed it down in May, built it off, redid everything, redid the greens," Kelly explained. "The grasses was the big deal for the change. It's 21 years old, so it was due for that."

She added something I appreciated: "That's one thing about On Top of The World, we keep everything pristine, maintained. And everything that's done in On Top of The World, we have employees for that."

The fitness facilities are organized by intensity level. The Ranch (an off-site facility you can join) has the highest intensity classes including cycling and something Kelly called "bikini body" workouts. The Arbors has more moderate options.

The cultural center books legitimate acts. Kelly rattled off: "We've had Willie Nelson, Kevin Costner, Sheena Easton, Air Supply. ABBA's coming back." Plus tribute bands for Eagles, Journey, and Foreigner.

There's a central square where they have live entertainment Thursday, Friday, and Saturday nights. Farmers market every Thursday. People bring food and drinks and dance.

The Lifelong Learning Center Surprised Me

In the Gateway of Services building (which also has medical offices, dental, and financial planners), there's a lifelong learning center. Kelly described hundreds of classes across two semesters.

"Anything from cooking to pottery to health and wellness, history classes, language, how do I work my iPhone," she said.

That iPhone class detail made me smile. That's practical education for the demographic. They also offer dance classes and have specific programs for things like Parkinson's and cognitive training.

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Understanding the Leasehold Deed Model

This is where On Top of The World gets interesting - and potentially confusing. About 65% of the community operates on what they call a "leasehold deed."

Kelly gave me the full explanation: "In this area where we maintain it, it's a leasehold deed. You have the same ownership here in this area as you would in the owner-maintained area. You can sell the home, lease it, will it, transfer the deed. You pay property taxes and you pay homeowner's insurance."

The difference? There's a 100-year lease on the property, but you have full rights to that property for those 100 years, including mineral rights.

"In our experience, if you were to leave that home to someone, they typically will sell," Kelly noted. "So generations, you probably have three or four generations that could inherit that home."

Here's the trade-off: in the leasehold areas, On Top of The World handles ALL exterior maintenance. Your yard, landscaping, exterior painting, roof - all covered.

Kelly said about 80% of people love the idea. "They don't ever want to do landscaping again." That's me too, honestly.

On Top of The World Prices: What Can You Get?

Pricing here varies dramatically based on what you're buying - resale versus new construction, and which neighborhood.

Kelly mentioned one resale that's only five years old, priced just over the new home price, but the owners put $30,000 in landscaping alone. "So that tells you there's so many upgrades in this home," she said.

New construction inventory homes (which can be anywhere from breaking ground to nearly complete) have "impeccable" pricing according to Kelly. "Ridiculously cheap," were her exact words.

They sold one that was just coming out of the ground where buyers were able to make color selections and even swap out appliances. "Usually builders will not make a change once you sign a contract, that's it. Or there's a hefty charge," Kelly explained. Not here.

Move-in ready homes can close in 2-3 weeks if you have cash, or 4-5 months if the home is still being completed.

One interesting tidbit: On Top of The World requires 20% down. But they're launching a new community called Melody Preserve (little to no amenities, lower price point) where they're planning to drop that requirement.

On Top of The World HOA Fees Explained

The $524 HOA fee applies to the leasehold/maintained areas. In these sections, you literally don't touch the exterior of your home. They handle everything.

Owner-maintained areas have lower HOA fees but you're responsible for your own yard work, exterior painting, roof, etc. It's a fee-simple ownership model in those sections.

Kelly emphasized that exterior homeowner's insurance is included in the maintained areas, which saves money. She also mentioned there are no hidden fees - everything is spelled out upfront.

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The Inventory Home Shift

Kelly shared something interesting about the market shift over the past year.

"Last year this time we didn't have inventory homes available," she said. "We had a handful of them, but not because they were flying off the shelves. We just, to-be-builds was where we were at."

What changed? People couldn't sell their existing homes as quickly. "The shift was people weren't able to sell their homes right away, and when they started recognizing that, they didn't want to wait for a home because they sat with their house on the market for so long that when they did sell, they wanted to move into something right away."

So now they're stocked with inventory homes, and they're priced competitively with resales.

Location & What's Nearby

On Top of The World sits in Ocala, right off State Road 200. The location is genuinely convenient.

Within golf cart range: three shopping plazas, medical facilities, banks, restaurants, Starbucks, ice cream shops, hardware stores, and soon Home Depot.

By car: Lowe's and Aldi are just down the road. Fire and rescue is one block away. An HCA emergency room and hospital are under construction nearby. Extended stay hotel going in too.

The World Equestrian Center is about 15 minutes away. Orlando is about 90 minutes. The community is mature with established trees and landscaping - you can tell this isn't a brand new development.

📞 Ready to See Homes in On Top of The World?

We work with agents who specialize in this specific community. Call us at 407.970.0958 and we'll connect you with someone who can show you what's currently on the market.

Is On Top of The World Right for You?

Ideal for: People who want a fully established community with every amenity imaginable but zero desire to maintain a yard. If you like the idea of golf cart living, regular entertainment, fitness classes, and educational opportunities, this is your spot. The leasehold model is perfect if you truly never want to think about exterior maintenance again.

Look elsewhere if: You're a serious golfer who wants to be on the course daily (only 15% of residents golf). You want a smaller, intimate community - this place is massive. You prefer fee-simple ownership everywhere and want control over your landscaping. You're looking for brand new construction exclusively - much of the community is established and resale-focused now.

Watch My Full On Top of The World Tour

Want to see everything I saw? Here's my complete video walkthrough:

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Frequently Asked Questions About On Top of The World

What are the HOA fees at On Top of The World?

HOA fees are $524/month in the maintained (leasehold) areas, which cover exterior maintenance, landscaping, lawn care, exterior painting, roof maintenance, exterior homeowner's insurance, trash, and amenity access. Owner-maintained areas have lower fees but you handle your own exterior maintenance.

What is the age requirement for On Top of The World?

At least one resident must be 55 or older. This is a true 55+ community with a no children policy for permanent residents.

Does On Top of The World have a golf course?

Yes, On Top of The World has three championship golf courses (one just renovated) and is adding a fourth executive 9-hole course in Waybourne Landing. Interestingly, only about 15% of residents are active golfers - most people use golf carts for transportation around the community.

How does On Top of The World compare to The Villages?

On Top of The World is significantly smaller and more intimate than The Villages. It's 43 years old versus The Villages still expanding. OTOW has about 2,000 homes across multiple neighborhoods, while The Villages has 100,000+ residents. OTOW focuses on maintained living with leasehold deeds in many areas. Price points are comparable but OTOW tends to be slightly more affordable for similar square footage.

Is On Top of The World a good place to retire?

If you want an active, amenity-rich lifestyle without maintenance responsibilities, yes. The community offers three golf courses, multiple fitness centers, cultural center entertainment (major acts like Willie Nelson), lifelong learning classes, and a strong golf cart culture. The leasehold model where 80% of residents love never doing yard work is perfect for people who want truly hands-off living. The maturity of the community (43 years old) means established landscaping and proven property management.

Ready to Take the Next Step?

Whether you're just starting to explore or ready to schedule a tour, we're here to help:

• 📞 Call: 407.970.0958
• 📧 Email: hello@explore55plus.com
• 📋 Get Matched: Fill out our quick form

Final Thoughts

On Top of The World isn't trying to be the newest, flashiest community in Florida. It's 43 years old and established - and that's actually its strength. The trees are mature, the amenities are proven, and the maintenance model works for thousands of residents who never want to touch a lawn mower again. If that sounds like your retirement, it's worth a serious look.