Contributing Writer

Cari Oleskewicz

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Cari Oleskewicz writes about Florida communities and news for 55places.com. She has created content for dozens of other online and print publications including ConsumerAffairs, The Washington Post, USA Today, PocketSense.com, and The Nest. In the last seven years, Cari has been invited to contribute blogs and articles for real estate and property management companies across the country, and has delivered presentations on the importance of content and web copy in building a real estate business.

Before launching her writing career, Cari was a communications and editorial strategist for a digital advertising agency in Tampa and managed the communications department of a nonprofit organization serving people with disabilities in Maryland. She has also taught middle school and writes poetry. Cari graduated from Marist College in Poughkeepsie, New York in 1994, with a BA in Communications/Journalism. She currently lives in Tampa, travels frequently, and recently helped her father find the perfect 55+ community to call home.

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388 Articles by Cari Oleskewicz

  • The Best Small Towns for Singles to Retire in Florida

    by Cari Oleskewicz on May 5th, 2021

    At 55places.com, we looked at over 29,000 areas designated by the most recent census data, focusing specifically on major areas with a population under 20,000. We then broke down each area by how many single or unmarried people made up the total population. Here are the 10 best small towns for singles to retire in Florida.


  • Homes and Amenities Revealed for Latitude Margaritaville Watersound

    by Cari Oleskewicz on April 30th, 2021

    Minto Communities in partnership with Margaritaville Holdings and The St. Joe Company recently announced the amenities and floor plans for this 55+ community in Northwest Florida. The news has only increased the interest and enthusiasm for this new construction, Jimmy Buffett-inspired community.


  • Tampa 55+ Communities Without Golf Courses

    by Cari Oleskewicz on April 27th, 2021

    Active adults looking for Florida retirement communities without golf courses have numerous options around Tampa, Clearwater, and St. Petersburg. The one you choose will depend on the amenities you desire, whether it's a waterfront location or a state-of-the-art fitness center.

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  • Where to Retire on Florida's Gulf Coast

    by Cari Oleskewicz on April 26th, 2021

    For outstanding beaches, ample golf, and all the boating, fishing, and nature that comes with coastal living, consider the Gulf Coast. Florida's west side has everything from shopping to professional sports and excellent restaurants. It also has a selection of desirable active lifestyle communities.

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  • Popular Florida 55+ Communities Without Golf Courses

    by Cari Oleskewicz on April 23rd, 2021

    Active adult communities don't have to be built around golf courses. If you're not someone who is interested in golf, or even if you're interested in golf but you don't want to live on a course, you have options. Take a look at these popular Florida communities without golf courses.

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