Well, lets see.
The NASA Deep Space Network (DSN) uses 70 meter antennas. They are still receiving signals from the 3.66 meter antenna on the Voyager 2 spacecraft.
Voyager 2 spacecraft is 133AU away. (1AU is the mean distance between the Earth and the Sun)
That's about 93,000,000 miles for an AU, times 133 (you get to do the math

)
The data rate from Voyager is 160 bits per second.
Now since dish antenna gain is proportional to area, lets see how antenna size affects things.
Using area = π x R
2
π x 35
2 = 3847 square meters. (DSN antennas)
π x 500
2 = 785,000 square meters (your antenna)
So your antenna will be 204 times as sensitive as the DSN antenna.
Now if you multiply the antenna gain by the bit rate ratio (not necessarily real accurate)
you get 204 x 160 = 32640. Multiply that by the answer you got for Voyagers current distance, above, and you get a lower limit for how far you could communicate with a 1Km antenna talking with a 3.66 meter antenna.
Trip time from Sun to Earth at 186,268 miles per second is 8.32 minutes.
8.32 x 133 = 18.4 hours for a signal sent from Voyager 2 to reach Earth.
Now another question arises:
Multiply that 18.4hrs by the 32640 found above, and you get 600,576 hours for a one-way message.
Divide that by 365.25 days in a year and you get 1644 years for a spacecraft transmission to reach Earth.
I think it will be a while before we have power sources that can last that long (and that is assuming the space craft was
traveling at the speed of light, not likely!)
Fun Idea though, (gave me something to do this evening)
Cheers,
Tom