Have you logged into the pi with this IP address before? Make sure you have the right IP address of the Pi.
Have you accessed any of the ssh config files recently? I've done this and made a typo rendering the configuration useless.
To find the ip address in four ways. With a keyboard plugged into the pi, press F4 and use the CLI to type in ifconfig you'll want to use the inet address of either the wlan0 or eth0 interface.
There is a menu option in emulationstation that will give the ip address most of the time.
And with windows you could type arp -a to check the arp cache for the address it will be one of the dynamic addresses of the associated interface.
Of course you want to make sure that it is connected, with ethernet you will know. With a router I guess you could log in to the router and check the ip address there.
You should start with ssh, when you get the right address I'll help with winscp.