There are 14 houses on Round Hill Road in Greenwich, CT on the market right now. Just like Lake Avenue and North Street, houses on Round Hill Road range in price from the extremely inexpensive and affordable (sarcasm) $2.795m to the fantastic $42.9m Helmsley estate. This street has something for everyone. Kidding aside, Round Hill Road offers some of the best real estate in the northeast. Being one of my favorite streets to drive, it is not a quiet suburban road, but more of a central artery stretching from northern Greenwich into town (meeting with Lake avenue).