When my clients first reached out from Tampa about relocating to Sarasota for work, they had a strategic plan: buy a condo, live in it for a year or two, then keep it as a rental property while upgrading to a larger home. Three months and one pivotal rental experience later, they closed on a 3,400 square foot home in Southbay Yacht and Racquet Club—completely abandoning their original investment strategy for something that better suited their lifestyle.
The Plan That Changed Everything
Their initial approach made sense on paper. Purchase a waterfront condo, establish themselves in Sarasota, build equity, and eventually transition to a larger home while maintaining the condo as rental income. It was practical, financially savvy, and perfectly logical.
Then reality intervened.
The Rental That Revealed the Truth
One of the smartest decisions my clients made was renting in an area they thought would be ideal. This trial run proved more valuable than any amount of property tours could have been. After just a few weeks in their rental, the limitations of condo living became crystal clear. The space constraints, community restrictions, and lack of flexibility felt suffocating rather than convenient.
More importantly, they realized something fundamental: they weren't ready to downsize from their 3,000 square foot Tampa home. The investment strategy was sound, but it didn't align with how they actually wanted to live.
Understanding Sarasota's Diversity
Coming from Tampa, my clients had to learn Sarasota from scratch. Each weekend brought discoveries about neighborhoods they'd never heard of and lifestyle options they hadn't considered. The diversity of communities—from downtown urban condos to golf course neighborhoods to waterfront resort communities—was both exciting and overwhelming.
One new consideration? Flood zones.
Coming from an area where this wasn't a factor, they learned that certain flood zones come with higher insurance costs. We discussed the implications so they could make informed decisions, particularly when looking at waterfront properties.
Priorities That Evolved
Over three months, their must-haves shifted significantly. What started as a search for an investment-worthy condo evolved into finding a home in an excellent school district that could accommodate their actual space needs and lifestyle preferences.
We toured numerous waterfront condos that would have made solid rental properties, but the question kept arising: did they really want to live with those constraints for even a year or two? The rental experience had answered that question definitively.
Why Southbay Became Home
Located in the highly-rated Sarasota County school district, Southbay Yacht and Racquet Club checked boxes they didn't even know they had when they started their search.
The deciding factor? The marina and waterfront amenities. The private marina with boat slips available for rent, yacht club, and stunning water access provided the resort-style living they craved. Combined with tennis and pickleball courts, a heated pool, clubhouse, and vibrant social scene, Southbay offered a lifestyle that no investment condo could match.
They found a spacious home that gave them over 3,400 square feet—even more than their Tampa house. The investment strategy was abandoned, but they gained something more valuable: a home that truly fit their lives.
Lessons for Future Relocators
My clients' journey offers valuable insights for anyone relocating to Sarasota:
Take time to really know the area. Sarasota features dozens of distinct neighborhoods, each offering different lifestyles. Where you choose to live significantly impacts your daily experience.
Test before you commit. Renting first can reveal truths about what you actually want versus what sounds good on paper.
Be flexible with your plan. The best financial strategy means nothing if you're unhappy with where you live.
Don't rush the process. Three months might seem long, but taking time to explore prevents costly mistakes.
Consider all costs. From HOA fees to flood insurance, understanding the total cost of ownership helps avoid surprises.
The Unexpected Ending
Now settled into Southbay with their unexpected 3,400 square feet, my clients have embraced everything their community offers. The marina has become their weekend retreat, they're active in community events, and their commute is shorter than it was in Tampa.
Their original investment plan may have been abandoned, but they found something better: a home and lifestyle they love from day one, rather than settling for something practical while waiting for their "real" home.
Considering a move to Sarasota? Sometimes the best plan is remaining open to changing your plan. The time you invest in understanding our diverse communities—and yourself—will lead you to the right home.
Ready to explore Sarasota's waterfront communities? Contact The Pope Team to start your journey home.
Check out this article next
