17.py 512 Bytes
#!/usr/bin/python

S = [0,3,3,5,4,4,3,5,5,4,3,6,6,8,8,7,7,9,8,8]
D = [0,3,6,6,5,5,5,7,6,6]
H = 7
T = 8
 
total = 0
for i in range(1,1000):
    c = i % 10 # singles digit
    b = ((i % 100) - c) / 10 # tens digit
    a = ((i % 1000) - (b * 10) - c) / 100 # hundreds digit
 
    if a != 0:
        total += S[a] + H # "S[a] hundred
        if b != 0 or c != 0: total += 3 # "and"
    if b == 0 or b == 1: total += S[b * 10 + c]
    else: total += D[b] + S[c]
 
total += S[1] + T
 
print "Result is: " + str(total)