Can I deduct property tax from a retirement community that I live in?

It depends.  Did you pay the property tax yourself?  Then, Yes.

Enter Property/Real Estate Taxes:

1. Open your return (if not already open)
2. Enter "property taxes" in the Search box.
3. Click on "jump to property taxes" link.
4. Enter your information.

Or are you referring to Continuing Care Retirement Community (CCRC) Entrance fees?

"You can include in medical expenses a part of a life-care fee or “founder's fee” you pay either monthly or as a lump sum under an agreement with a retirement home. The part of the payment you include is the amount properly allocable to medical care. The agreement must require that you pay a specific fee as a condition for the home's promise to provide lifetime care that includes medical care. You can use a statement from the retirement home to prove the amount properly allocable to medical care. The statement must be based either on the home's prior experience or on information from a comparable home."

Medical and Dental Expenses IRS Pub. 502 - Page 10

To deduct medical, dental, or vision costs on your federal return, you have to itemize your deductions instead of taking the Standard Deduction. 

If you itemize, you can deduct medical expenses that exceed 7.5% of your adjusted gross income (AGI)

Enter Medical Expenses:

1. Open your return (if not already open)
2. Enter "medical expenses" in the Search box.
3. Click on "jump to medical expenses" link.
4. Enter your information.