I’ve been going to Venice, Florida since I was a toddler. My mom’s college roommate was from there, and we’d spend most of our spring breaks driving to Florida in our station wagon.
Then, when my parents retired, they started wintering in Venice, Florida— first renting in this charming complex of “villa” units tucked alongside a golf course (without the club dues and all the baggage that comes with that), and then they purchased the unit when the owner decided to sell.
I’m always “looking”
I’m an admitted real estate junkie. I will pull the car over, to open the Zillow app and investigate what the housing stock is going for in a particular neighborhood. Or stay up late looking at “Zillow porn”. So naturally, the more time I spent in Venice, and the older I got, I started to appreciate how a place in Florida might make sense. Even if there were things I didn’t (and don’t) love about Florida.
But, soon the good started to out weigh the bad.
Pros & Cons
The units are “villas,” which means they feel more like single-family homes than traditional condo units — real walls, real separation, real breathing room. The homeowner’s association is exceptionally well-run, which anyone who has dealt with a poorly run HOA knows is not something to take for granted. The location is genuinely special: Venice is a small, walkable town with a palm tree-lined downtown full of great shops and restaurants. It feels like “old Florida”, before every coastal town became an outlet mall and a traffic jam.
This community is within just a few miles of multiple beaches, with minimal traffic to get there. And, for being so close to water our community sits just outside the hurricane flood zone. That last point matters more than most people initially realize, and we’ll come back to it.
This was, in our view, a gem of a community in a gem of a town. The question was just whether the timing was right for us.
Right Unit, Right Time
I was visiting my dad in Venice, when on Zillow I noticed that a 3 bedroom, 2 bath end-unit villa on the golf course was on the market. It had a gorgeous, huge tree right outside that really caught my attention. I thought about it and talked to Elizabeth,who truth-be-told, was never a Florida lover. Initially, she was not that in-favor of it, but the more I explained and showed her the pictures, she gave me the go-ahead to see it.
Planning for Our Next Chapter
Elizabeth and I are in one of those interesting in-between chapters, which I wrote about here. She stepped away from teaching last year. I’ve been consulting and love all the flexibility that affords. We still have young-adult children in the mix, so “empty nesters” is not a label that applies to us yet — not by a long shot. But we’ve started having conversations that a lot of people our age are starting to have: Where do we actually want to spend our time? What does the next version of our life look like?
We know we want to travel — and not just the quick-hit, five-nights-and-out kind. Being able to spend a couple of weeks somewhere and actually get to know it is our goal. In the summers, we want to spend real time in Michigan, between our place in Union Pier and on the lake in Traverse City. We want flexibility and options.
What we hadn’t fully mapped out was the winters. And once we started thinking about it honestly, the answer kept pointing south.
Stress Testing this Decision
Here’s where I want to be real about the thinking, because we didn’t just fall in love with a place and write a check. We ran it through a filter.
Manage Expenses
We were able to pull money out of savings to not have a mortgage. That changes the risk profile of any real estate purchase significantly. There’s no mortgage hanging over it, no monthly nut that must be covered no matter what. The carrying costs are manageable, and we’re not leveraged in a way that would hurt us if the market softened. And, the plan was to rent it, see below.
Rent it for “The Season”
When I went down a month later for the inspection, word had gotten around that we had bought the unit. A couple contacted me and wanted to see if for next “season”—January, February and March. We agreed on a price and as soon as we closed, I sent them a lease. Those three months alone will cover all our out-of-pocket expenses for the year. Essentially, the property pays for itself in the short term while we figure out exactly how we want to use it long term. That’s not an accident — Venice has a strong seasonal rental market, and we knew going in that we could generate income from it when we weren’t there.
Healthcare Will Be Important
Having spent a lot of time down there with both my aging parents, I am fully appreciative of being located near a good healthcare system. And, my parents have always gotten great care within the Sarasota Memorial Health system right there in Venice. As we think about an eventual home-base after we’re finished traveling, that is a major plus.
Dated Interior for the Win!
The community was built in 1986, is very solid and this unit has original everything. For some buyers, that’s a red flag. For us, it’s a blank canvas. This unit is a bit dated, but CLEAN. So, when the time comes to update the kitchen, redo the bathrooms, or put our own stamp on the space, we won’t have to feel guilty about pulling out someone else’s recent renovation. We can make it exactly what we want it to be, without the guilt of replacing something that has been recently updated, but not to our taste.
And, until that time, it’s good to go as it.
Outside the Flood Zone
Florida real estate has gotten complicated for a reason: flood insurance costs have skyrocketed, and some areas have become genuinely difficult to insure. Being just outside the flood zone isn’t a minor detail. It’s a material factor in both the cost to own, the long-term value of the property and peace-of-mind if a hurricane hits and you’re not there.
Taking No Chances with the Windows
The one investment we made immediately was installing hurricane-proof windows. My dad had recently installed them and it made a huge difference. Yes, it’s a significant upfront cost. But the original windows were fragile and thin — and the peace of mind that comes with knowing a storm isn’t going to blow one in and cause catastrophic interior damage is worth every dollar. One bad event through an old window can cost far more than the windows themselves. We’re treating it as a non-negotiable part of making this place truly ours.
What We Really Bought was Optionality
When you add it all up, what we’ve bought isn’t just a condo in Florida. It’s optionality. It’s a place that covers its own costs, in a town we genuinely love, in a community with a track record of being well-managed, in a location that sidesteps some of the biggest risks associated with Florida real estate right now.
This gives us a home base for the winters we haven’t fully planned yet. It gives us a gathering place for family. In the short term, it gives us a rental asset and an appreciating piece of real estate in the long term — in a market where demand for exactly this kind of property isn’t going away.
And it gives me something I didn’t expect: the feeling of completing a circle. From spring break trips as a kid to winter visits with my kids to us now owning a piece of it — Venice has been part of my story for a long time.
And, I can’t wait to start decorating it …thinking Bahama’s-meets-Palm-Beach-style. But first, we need to get it ready for the renters. Stay tuned.
WETSU! WETSU!
XO JT
