Looking to buy a property in St Augustine

Member since 2025 · 1 post · 2 votes

Me and my wife live in the central Florida area. We are very interested in buying a small place in St. Augustine and we've never done anything like this before. We do own our own single family home and both work full time jobs. We'd like to get something we can AirBnB for vacationers most of the year. I listen to the podcast and read a lot of the forums here and just wanted to touch base with someone who's been in our shoes and get some support in this endeavor. Thank you!

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J CastroBusiness Member
Lender · Florida · Member since 2025 · 673 posts · 240 votes
1y
Hey @Brad Braunstein welcome to BP!
Buying an investment property in St. Augustine, Florida can be a worthwhile investment, but it depends on individual circumstances and priorities. Based on current information, St. Augustine, can be a promising location for real estate investment, especially considering its blend of historical charm, attractive amenities, and growing popularity.
The influx of tourists (over 2 million annually) creates a robust short-term rental market, while the expanding economy and increasing population contribute to strong demand for long-term rentals as well. Well-located vacation rentals can generate significant cash flow.
With that said, the success in real estate investing depends heavily on understanding the specific dynamics of the local market, including neighborhoods, development trends, and regulations. This is particularly crucial in areas like St. Augustine where there's a strong tourism component and specific zoning laws for vacation rentals.
It's crucial to carefully research into specific neighborhoods, market trends, and potential risks, particularly related to property taxes and insurance, is recommended. Consulting with a local investor friendly real estate expert can be invaluable in navigating zoning laws, identifying promising investment opportunities, and understanding the nuances of the market.
Best of Luck!
JCREIG Capital Funding
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Arman AhmedPro Member
Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 911 votes
1y
@Brad Braunstein
Brad, that’s awesome—congrats on taking the first step. St. Augustine is definitely a strong short-term rental market, but like any tourist-driven spot, the big things to watch are seasonality, management costs, and regulations. A lot of first-timers hedge risk by buying a place that also pencils out as a long-term rental if rules ever shift.

Since you’re new to STRs, it might also help to compare what cash flow looks like in out-of-state markets too—especially some Midwest cities. Tourism is great for appreciation, but Midwest markets often give more steady year-round returns and affordability, which is why a lot of investors balance both.

Are you planning to self-manage or lean on a local property manager? That usually ends up being the biggest factor in how smooth the first deal goes.

[email protected]614-418-6081
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Joseph Bui
Lender · Nationwide · Member since 2023 · 362 posts · 237 votes
1y
Hi Brad, buying an investment property is always scary at first. I've been helping investors finance their rentals in Florida and I think the numbers can work out really well. Let me know if you have any questions about financing or investing. I'm a mortgage broker but also an investor with 8 doors across memphis and detroit.
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Chris MuryBusiness Member
Realtor · St. Augustine, FL · Member since 2017 · 182 posts · 100 votes
1y
Quote from @Brad Braunstein:

Me and my wife live in the central Florida area. We are very interested in buying a small place in St. Augustine and we've never done anything like this before. We do own our own single family home and both work full time jobs. We'd like to get something we can AirBnB for vacationers most of the year. I listen to the podcast and read a lot of the forums here and just wanted to touch base with someone who's been in our shoes and get some support in this endeavor. Thank you!

Welcome to BP! I'm obviously very biased but love the Saint Augustine market for Airbnb/STR!
Chris Mury- Realtor543 Reviews
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Andrew SteffensBusiness Member
Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
1y
Im out of Tampa but I have a great referral for you, Ill DM you.
[email protected]813-563-0877
Vacation Rentals of Florida53 Reviews
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David NilesBusiness Member
Property Manager · DeLand FL · Member since 2012 · 860 posts · 243 votes
1y
Hey Brad, welcome to BP. My wife and I are also in central Florida but can help with searches, vendor info etc. We just had a client looking in St Augustine recently but as a primary residence. Drop me a pm if you want to talk, set a search or whatever we can help with.
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Krista Hoff
Real Estate Agent · St. Augustine, FL · Member since 2023 · 7 posts · 1 vote
1y
Hi Brad, I'm a local resident & STR focused Realtor in St. Augustine. You mentioned being interested in a smaller home. I have one listed that is a smaller 3/2 on the outskirts of downtown that is grossing $54k annual. It's priced at $340k, and it is possible to find smaller properties in that price range. I'd be happy to help you explore the opportunities in our beautiful city.
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