YOU SAID:

the man entered the room cold rusty flat he sat down

INTO JAPANESE

男は彼が座って部屋の冷たいさびたフラットに入った

BACK INTO ENGLISH

The man went into a cold rusty flat in the room where he sat

INTO JAPANESE

男は彼が座っていた部屋の冷たいさびたフラットに入った

BACK INTO ENGLISH

The man went into a cold rusty flat in the room where he was sitting

INTO JAPANESE

男は彼が座っていた部屋で冷たいさびたアパートに入った

BACK INTO ENGLISH

The man entered a cold rusty apartment in the room where he was sitting

INTO JAPANESE

男は彼が座っていた部屋に冷たいさびたアパートに入った

BACK INTO ENGLISH

The man entered a cold rusty apartment in the room where he was sitting