- Red Board
- Red Diary
- Red Pyramid/The Nurses
- Red Shoe
- Red Siren
- Red Square
- Regards
- Reminisces
- Remnant
- Remodeling
- Rendell Street
- Renewal Card
- Replacement Bulb
- Repression and Coercion
- Resort Area
- Resting Comfortably
- Resting Comfortably - Nasty Remix
- Result
- Return to Silent Hill
- Reverend Stone
- Revolver
- Ribbons
- Richard Braintree
- Richard Grady
- Richard Grosse
- Rick Albert
- Ricky
- Riding Crop
- Rifle
- Rika Muranaka
- Ring of Contract
- Ring of Fire
- Riot News
- Rising Sun
- Ritual of the Holy Assumption
- Riverside Drive
- Riverside Motel
- Robbie Doll
- Robbie the Rabbit
- Robbie the Rabbit Pin
- Robert Belgrade
- Robert Tower
- Roberto Campanella
- Rock
- Rock Drill
- Roger Avary
- Roller Coaster Key
- Romper
- Roof Key
- Room 301 Key
- Room 302
- Room 302 of the Past
- Room 306 Key
- Room 500 Key
- Room 502 Key
- Room of Angel
- Rope
- Rose Da Silva
- Rose Heights Cemetery
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