Windsor Hills Disney World cash flow expectations

[Jon Greves]

I'm looking for my first STR to purchase in Florida. I live in WI. I've discovered Windsor Hills near Disney World as a good starting point for myself.

I have 25% to put down on $600-$700K home (4-6 Bedroom).  I'd like to be able to handle the bookings, pricing and pre-booking questions myself.   I would need cleaning, pool maintenance, general maintenance services as they arise.

Can STRs in this area still cash flow under these general scenario with these prices, interest rates, saturated market? What could be a general cash on cash return for someone that was heavily involved in the success of the STR?

Thank you for any info you can provide

[Travis Main]

Hey Jon, 

I'm not familiar with Windsor Hills, but I know that Reunion is another STR community. I have a lot of clients who own in that community and are doing well with their STRs.

The one thing that you might want to check with Windsor Hills, do they make you use their services to manage the property or can you self manage. 

[Alice Horn]

Quote from @Jon Greves:

I'm looking for my first STR to purchase in Florida. I live in WI. I've discovered Windsor Hills near Disney World as a good starting point for myself.

I have 25% to put down on $600-$700K home (4-6 Bedroom).  I'd like to be able to handle the bookings, pricing and pre-booking questions myself.   I would need cleaning, pool maintenance, general maintenance services as they arise.

Can STRs in this area still cash flow under these general scenario with these prices, interest rates, saturated market? What could be a general cash on cash return for someone that was heavily involved in the success of the STR?

Thank you for any info you can provide

 Hi @Jon Greves - We're boutique property managers with about 50 STR's scattered throughout the Disney market, including Windsor Hills. Windsor Hills is an excellent starting point, as it has great name recognition with tourists and is one of the closest communities to Disney. The community also has great amenities (free waterpark, etc) which sets it apart from the other communities near Disney. I am happy to pull a report on revenue and occupancy for a typical WH home, and help you analyze the investment potential. You may also want to compare the numbers with other nearby properties, i.e. Emerald Island; or newer communities further West (Solara, Windsor at Westside, Windsor Island, etc.)

By the way, Windsor Hills does not require you to use onsite management - they are flexible regarding the management structure for the property.

Just let me know how I can help!

[Ryan Moyer]

People beat around the bush a lot and won't give it to you straight.

The simple answer is no.  You are not going to cash flow unless you are extremely good at off-platform marketing.  And probably not anywhere close to it.

The area is saturated and expenses are high. Insurance and taxes are both high, on top of your high rate, your mortgage will be large. The HOA is not cheap. And general expenses are extremely high in this area compared to most markets. You've got builder grade houses full of rambuncious kids with tired parents. Things get dinged up. The roof leaks. The fridge stops cooling. The spa breaks constantly from overuse.

Maintenance and expenses are just high here relative to most markets.  We own in multiple markets and our expenses here are easily triple to quadruple what they are in some other markets.  It's just part of the territory.

Bookings-wise a 4-6 bedroom home is not large here.  It's on the smaller end of average.  You're competing with tens of thousands of homes in that size range, and most of them have the resorts etc.  The location at Windsor is your major advantage, but it's a large neighborhood (so still lots of competition in that bucket), and to really take advantage of that you have to be good at off-platform marketing because the majority of Airbnb guests are searching thinking that all of the resort neighborhoods are similarly close to Disney, as they're not savvy enough to know that the others are on I-4 and take much longer in real-time.

The days of being able to buy a random turn key STR in a crowded market and throw it on Airbnb and cash flow are long over. Higher rates, increased home prices, higher expenses, and extreme saturation have changed that. And of course it was always going to be temporary as people rushed in to grab it once the secret got out. That is true in most STR markets, but especially here where you're competing with tens of thousands of rentals fighting price wars.

Disney is a great market if you want a place near Disney primarily for vacation use and want some renters to supplement your mortgage.  It's also a great market if your goals are more old-school long term real estate because it's probably one of the safest markets (there is near zero regulation risk in communities like Windsor and near zero chance of tourism moving out of the area like some other trendy markets going around right now that people will forget about in 10 years).

But if you're a cash-flow focused investor and that's primarily what you care about, you're better off looking elsewhere (and really it's as much about the deal as the market these days) unless you're willing to spend $100k+ on theming.  And even in the latter scenario, that's still a very crowded market nowadays.

I manage in the area and the number of people that come in with completely disporportionate expectations to reality is staggering when they can so easily spend 5 minutes looking on Airbnb and see thousands of available properties on Airbnb that are WAY better than the one they're buying that are listed for sub $200/nt and still not booked.  Realtors are feeling the squeeze after getting a taste of the good life coming out of covid when everyone was buying everything because everything would cash flow, and desperate to hang on to that life there are a lot of buyers being misled into bad investments, if actual cash flow is a primary goal of their investment.

[Shawn McCormick]

@Jon Greves although Windsor Hills is one of my top 5 communities when factoring in all aspects of what other communities nearby offer, the homes are older (2004-2006) and compete with mostly 2015-2024 homes with more modern amenities, finishes and just cleaner overall. You'll have to factor in the age of the roof, mechanicals, furniture, appliances and deferred maintenance and the pool likely needs to be refinished too. 

All that being said, Windsor Hills does have a pretty loyal following, heavily from UK clientele that have been going there for many years. So if the house is head and shoulders above the rest and you can reach potential guests outside of the big platforms, you can still do okay. You should be able to do much better than a long term rental income, but the amount of work and time to put into a STR is much more than most consider.

There are a lot of motivated sellers in our market, so if you intend on purchasing here, make sure to research and don't pull the trigger on just any home. I'm happy to talk thru this in more detail if you like, reach out anytime.

Best of luck!