Things to consider when investing in Orlando
Member since 2024 · 16 posts · 7 votes
Things to consider when investing in Orlando
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Shawn McCormickPro Member
Realtor · Central Florida-Orlando · Member since 2014 · 1k+ posts · 894 votes@Daniel Gugliotti sounds like you understand the market and risks enough to evaluate some properties. Curious why you would want condos? You did mention STR, is that what you are looking to do, if so your best bet is in the Kissimmee/Davenport area and stay within a resort community. There are quite a few that are zoned specificially for short term (i.e. Windsor Hills, Storey Lake and other that have condos).
The HOA fees are going to eat into profits weather long or short term, but with short term, the guests get resort amenities and generally cable/internet/trash is also included, so at least you get some benefits.
If you want long term, you'll have to make sure the condo is warrantable and the complex has the right mixture of investor to owners. Depending on the demographic you are looking for would help determine what part of town to look in. Downtown and surrounding neighborhoods will get you younger professionals working the hospitals/office buildings, Out by UCF-students, near Disney-roommates sharing a condo. Out by the airport will be a different mix of everything.
As far as multi family, we don't have much worth looking at here. It is typically overpriced, older, usually need many updates/reparirs and many times not even a true multi (garage conversions etc). They are scattered and the good ones don't come on market very often so you have to really watch for them.
Happy to dive a little deeper if you have specific questions. Reach out anytime.
Best of luck.
10 Replies
- 1yShawn McCormickPro MemberRealtor · Central Florida-Orlando · Member since 2014 · 1k+ posts · 894 votes
@Daniel Gugliotti sounds like you understand the market and risks enough to evaluate some properties. Curious why you would want condos? You did mention STR, is that what you are looking to do, if so your best bet is in the Kissimmee/Davenport area and stay within a resort community. There are quite a few that are zoned specificially for short term (i.e. Windsor Hills, Storey Lake and other that have condos).
The HOA fees are going to eat into profits weather long or short term, but with short term, the guests get resort amenities and generally cable/internet/trash is also included, so at least you get some benefits.
If you want long term, you'll have to make sure the condo is warrantable and the complex has the right mixture of investor to owners. Depending on the demographic you are looking for would help determine what part of town to look in. Downtown and surrounding neighborhoods will get you younger professionals working the hospitals/office buildings, Out by UCF-students, near Disney-roommates sharing a condo. Out by the airport will be a different mix of everything.
As far as multi family, we don't have much worth looking at here. It is typically overpriced, older, usually need many updates/reparirs and many times not even a true multi (garage conversions etc). They are scattered and the good ones don't come on market very often so you have to really watch for them.
Happy to dive a little deeper if you have specific questions. Reach out anytime.
Best of luck.
- Member since 2024 · 16 posts · 7 votes1y
Thanks, @Shawn McCormick!
To answer your question, STR is the better money play to mitigate some of the risk HOA costs present. My preference is LTR, but that seems unattainable in many areas.
It’s good intel of verifying the condo is warrantable and finding the right mix of investors to owners. What’s the best way to determine that - good old fashioned owner lookup? Or is there a more efficient way to verify that?Thanks again Shawn!
- Member since 2024 · 8 posts · 3 votes1y
Hi Daniel, Im happy to help. I work for a property management company and do flips on the side. I wouldn't recommend short term because the inventory is so high in Orlando in general and Spring is generally the high season. I would definitely recommend long term. If you're interested in condos with low HOA in a great location, I'd recommend around N Orange Ave close to Ivanhoe area. The best areas from both an appreciation and rental standpoint are around Mills50, because that's where you'll find the best restaurants.
- Member since 2024 · 16 posts · 7 votes1y
Thanks, Patrick! This is super helpful!
- Real Estate Agent · Tampa Florida · Member since 2013 · 630 posts · 303 votes1y
@Shawn McCormick
Most Orlando neighborhoods actually promote STR. They framed it inviting to fault owners from acquiring additional wealth. Some investors find it unfair that there are "said" investors better at discovering and utilizing resources to their advantage.Start with identifying the "Primary Subject" property. Then, diligently cross reference it with all available "Vacation Sites" (search using the subject property address) The owners/ Hosts info will pull up in a general search of what's close. Research each listing from all platforms and you will see trends, Discriptions, Inticing or family friendly Waze to attract attention to the property. Only appropriate and pertinent info will attract the upper echelon of respected guests to visit your STR. Less is more. Simple, classy, retro & even vintage decor is bring in the big moola. Even if I had the bank roll to bling out a spot, I would never waste it on the important things your guests will make everlasting memories with. HOA is irrelevant in these cases. Once you put some effort into finding out the Minutes and By-Laws from the association, you throw that HOA out the window knowing that your thought out investments profits outweighs the HOA by 50% Ya'lls ROI can't be beaten any more. That HOA gets long forgotten. There are multiple similar names and areas, so please use caution when comparing vacancy rates, nightly rate trends and sleeping capacity. Does the listing show that it's business, vacation destinations nearby and has room for a family of 4 to be accommodated for? Oh, and don't forget the 5th, their dog. Not only do you need to know St. names and subdivisions which gross more revenue, and for Pete's sake, the condo complex will allow you to utilize their resort style pool and quant lounging area with multiple TVs and the liquors a flowing. It's all about a vibe. Does the STR make you feel at home? Does it have the take your shoes off and rest a while enjoying the fancy rolls of TP you never splurge on at home? No matter, where, when or how a STR is made, it should always be the place everyone wants to call home after traveling 1000 miles which is never too far if you really enjoy the ambiance, amenities, unwarranted surprises and mindful upgrades your STR holds. To top it off a family friendly excursion to Universal while making lifelong memories. Will I always give the best advice, maybe, no. I will keep it real and be glad to answer anyone needing additional resources when I have my a chance to share the wealth with like minded and passionate individuals like myself.
- Investor · Member since 2024 · 83 posts · 58 votes1y
Hi Daniel, great question and welcome to exploring the Florida market!
You're absolutely right that Orlando can pose some challenges with condos: high HOA fees, insurance hikes, and limited short-term rental (STR) flexibility. These factors can definitely eat into cash flow.
If you're leaning toward condos, I'd recommend looking closely at HOA financials and bylaws, not just the fees. Some HOAs are better managed than others, and a healthy reserve fund can signal less risk of special assessments.
That said, if you're open to it, small multifamily properties (2–4 units) may offer better long-term upside and more flexibility. Even in Orlando, there are pockets where multifamily makes sense and STR or mid-term rentals (like traveling nurses or corporate stays) are allowed or easier to manage.
Another strategy some investors use is targeting "condo-like" townhomes without large HOAs or deed restrictions, they often offer similar affordability without the downsides.
Ultimately, Orlando still has great demand drivers (tourism, population growth, job market), so it’s all about aligning the property type and area with your investment goals.
Happy to dive deeper if you have specific properties or zip codes you’re considering! We personally invest in Orlando / Central FL, nearing 10 properties here.
- Flipper/Rehabber · Bloomfield CT · Member since 2020 · 1k+ posts · 409 votes1y
Another Connecticut person here looking at duplex's in Orlando. Targeting Clermont and Daytona Beach areas
- 1yTyler GibsonBusiness MemberReal Estate Agent · Orlando, FL · Member since 2017 · 1k+ posts · 2k+ votes
Quote from @James McGovern:
Another Connecticut person here looking at duplex's in Orlando. Targeting Clermont and Daytona Beach areas
You won't find too many duplexes in the Clermont area. You will find more in Daytona Beach. If you're not familiar with the areas. Make sure you find somebody who is that can help guide you.
- Flipper/Rehabber · Bloomfield CT · Member since 2020 · 1k+ posts · 409 votes1y
@Tyler Gibson I have family in the area that is scouting for ne
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