7 Critical Steps to Retire on Sanibel Island

It’s no secret that for many of our visitors, it’s their dream to retire on Sanibel Island (and Captiva too). With beautiful natural beaches, unique wildlife, warm weather, and a small-town community vibe – our islands are the perfect place to relax and enjoy not working!

To help get you where you want to be, we’ve listed 7 Steps to Retiring on Sanibel and Captiva Islands.

Steps to Retire on Sanibel Island:

Step #1. Visit Our Islands!

OK,  this sounds like a no-brainer, but you’ll never get a real feeling for a community from the Internet. Many of the people we work with are deciding between Sanibel, Captiva and some other beach town. We know Florida really well and are happy to share our thoughts on different communities, but the best advice I can give is to spend time in each location, at different times of year. 

Susan loves to tell people to go hang out at local grocery stores to get a ‘feel’ for the community. Make sure you understand the weather (some beach towns in Florida can get cold in the winter!). Also, you should try and predict what future development will take place. I’ve watched parts of Florida go from sleepy town to suburban sprawl seemingly overnight.

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Step #2. Chat with a Real Estate Professional

Even if you haven’t totally decided on the area you’d like to retire, it’s helpful to speak with a real estate agent early in your decision making. You may be able to eliminate or focus in on certain communities quickly and not waste time looking at properties that are not located where you will end up buying. Narrow your search, then learn about local market conditions and cost of homes in that area. More focus allows you to be more informed and ready to take smart action when the time is right for you.

Step #3. Drive or Bike Around Town

When deciding where to retire on Sanibel Island, you first need to consider which part of the island you prefer. While our islands aren’t huge, each area offers a slightly different experience than another.

For instance, the east end of Sanibel Island is more quiet and less congested than mid-island areas along Periwinkle Way, where many of the island shops and restaurants are located. There are similar differences when comparing the busy north end of Captiva Island, where there are restaurants and the South Seas Resort, with the calmer mid-island residences and rental homes. 

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Step #4. Decide Home or Condo

The decision to retire on Sanibel Island requires some thought as to whether you’d like a single family home, 1/2 duplex, or condo unit. To help, you should start by asking yourself:

  • Will I be moving and living here full-time, or will this be a second home?
  • Is rental income important? Will we use this primarily as a vacation rental home?
  • Will we use it for our own family vacations instead, choosing not to rent it out during season?

All of these factors play a part in deciding whether a home or condo is the best fit for you.

House Hunters: Click here to view all gulf front homes for sale on Sanibel Island.

Condo Seekers: Click here to view all gulf front condos for sale on Sanibel Island.

Step #5. Pin-Point the Style of Home

After debating home vs. condo, there’s still another round of questions to consider.

If searching for a house, you should ask yourself:

  • Do you want an elevated home or a ground level ranch?
  • Do you want to be walking distance to the beach, or is “biking-distance” okay?
  • Are you looking for a golf course community, or a neighborhood without an HOA?

If searching for a condo, you should ask yourself:

  • Do you prefer a large complex with multiple buildings and amenities?
  • Or, do you prefer a smaller condo with fewer units and less turnover during season?
  • What are the rental restrictions for the complexes you are considering?

I know, it’s a lot to consider. Your real estate agent can help you work through these and a number of other questions to consider when planning to retire on Sanibel Island.

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Step #6. Watch the Market

By this stage in your home search, you should be receiving email updates on homes that come on the market and meet your criteria. If not, you should ask your real estate agent send you properties that meet the goals and requirements you discussed in Step 5. Stay up-to-date with the market, checking the stats of what’s sold and what’s come on the market each week, so that you have a good feel for the current market situation.

Step #7. Visit Homes

As you get closer to the time you want to buy, I usually say a year to six months, you should start viewing homes with your agent. Walking through a few properties helps you to get a feel for the condition of the homes you’ve been viewing online, and also further narrow down the playing field of homes you’re considering.

Finally – You’ll stumble upon “The One,” and even if it takes a little warming up to, you’ll be confident and ready to move forward with an offer, knowing you have taken the proper steps leading up to your big decision.

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Jim McCallion About Jim McCallion

Meet the "Marketing Megaphone" and Webmaster behind McCallion & McCallion. After selling his software company, Jim, Susan and kids moved to Sanibel in 2008. With his tech experience, he and Susan bring a fresh approach to island real estate.