I had the same error and google brought me to this question, so here is what I did, hoping that it helps others in a similar situation.
This is applicable for OS X.
Check in the Terminal which version of OpenSSL I had:
$ python3 -c "import ssl; print(ssl.OPENSSL_VERSION)"
>> OpenSSL 0.9.8zh 14 Jan 2016
As my version of OpenSSL was too old, the accepted answer did not work.
So I had to update OpenSSL. To do this, I updated Python to the latest version (from version 3.5 to version 3.6) with Homebrew, following some of the steps suggested here:
$ brew update
$ brew install openssl
$ brew install python3
Then I was having problems with the PATH and the version of python being used, so I just created a new virtualenv
making sure that the newest version of python was taken:
$ virtualenv webapp --python=python3.6
Issue solved.