Essentially what I am asking is if there is some kind of correlation between a number such as √385 and it's factorization (which is 5,7,11).
Is it possible to use a number's (especially very large ones) square root to help in finding out it's prime factorization?
The relevant fact here is
So, if you search for prime factors of $n$ and haven't found one when you reach $\sqrt n$, then you know that $n$ is prime.
If you do find a prime factor $p$, then repeat the process with $n/p$ and so. (You can start at $p$ instead of at $2$.) This will find the prime factorization of $n$.
In your example, since $\sqrt{385} < 20$, you only need to try to factor $385$ with primes less than $20$. The first factor is $5$ and the quotient is $77$. The first factor of $77$ is $7$ and the quotient is $11$. Since $11$ is prime, you're done: $385 = 5 \cdot 7 \cdot 11$.