The incident unfolded at about 11:40 p.m. in the 700 block of NW 120th Street, in the Broadview neighborhood near Carkeek Park.
Police say two men wearing dark-colored ski masks forced their way into the home through a back door as the homeowner and a 51-year-old woman were in bed sleeping, said Jeff Kappel of the Seattle police.
One of the robbers confronted the homeowner, pointing a gun at him and demanding money. The homeowner fought with the man, but during the struggle the homeowner fell down and was kicked by the suspect.
The robbers stole the man's Rolex watch and a diamond ring, then grabbed the girlfriend's purse, ran out the front door of the house and fled the scene on foot.
Officers responded to the scene and searched the area with a police dog, but the suspects could not be found.
During the search, the police dog found some items about a block away from the victim's home that are believed to have come from the girlfriend's purse, Kappel said.
The suspects remain at large. They are described as black males in their 20s who were wearing dark ski masks. One suspect was wearing a white T-shirt and blue jeans, and was armed with a black handgun. The other man was wearing a dark jacket and blue jeans.
Medics checked out the homeowner and determined he did not need medical treatment.
Kappel said the same homeowner was the victim of a home-invasion robbery in February 2013.
The investigation continues. Anyone with information or who may know the identities or whereabouts of the suspects is asked to call 911 or the Seattle Police Robbery Unit at 206-684-5535. Anonymous tips are welcome.