- Olde Springfield Towne
- Olmec Head
- Om Is Where the Heart Is
- Ominously Blank Graveyard
- On-the-Job Straining
- On Thin Ice
- On Thin Ice,
- On the Fritz
- Once Bitten, Twice Die
- Once In Royal Quimby's City
- Once Upon a City Dreary
- Once Upon a Time in Springfield
- Once You've Gone Organic
- One Girl Army
- One Last Presidential Prank
- One Night Stan's
- One Small Bounce For Man...
- One Tough Cookie
- One Track Mind
- One Week Wonder Films
- One Week Wonder Films (questline)
- Oops, I Did It Again
- Opal
- Open Air Stage
- Opera House
- Opera Krusty
- Operation Clogged Drain
- Orange House
- Orange Pride Hydrant
- Orange Tree
- Orb of Isis
- Orc Willie
- Order in the Castle,
- Ordnance Express
- Orfanato De Artie Ziff
- Origin
- Original Brown House
- Original Springfield Post Office
- Ornate Pier
- Ornate Pier Bench
- Ornate Pier Post
- Ornate Pier Railing
- Ornate Ruin Wall
- Orphan Alley
- Orphan Alley (quest chain)
- Orthodox Ambulance
- Orville
- Osaka Seafood Concern Squid
- Oscar's Obstacles Truck
- Oscar Wilde
- Other Springfield
- Otto
- Otto (quest chain)
- Out Cold
- Out With the Old
- Out of the Broom Closet
- Outdoor Feast Table
- Outdoor Half-Court
- Outdoor Opera Seats
- Outdoor Opera Stage
- Outdoor Opera Ticket Booth
- Outland Sign
- Outlandish Creations
- Outlands Factory
- Outlands Gate
- Outlands Maggie
- Outlands Simpsons House
- Outlands Water Tower
- Outlaw Snake
- Outrageous Balloons
- Over Spilled Yolk
- Over Under Beast
- Overgrown Ruins Bundle
- Overpass Diner
- Oyster Eating Table
- PaDubba the Dubsteppa
- PaZIFFic Princess
- Pacifiers
- Packing Heat
- Paddy Wagon
- Pagan Bonfire
- Pagan Cauldron
- Pagan Hall
- Pagan Winter Carnival Sign
- Pagans
- Pageant Stage
- Pagoda
- Pai Gow Yee Haw
- Pain Killer
- Pain in the Jass
- Painless Dentistry
- Painted Home (1)
- Painted Home (2)
- Painted Home (3)
- Painted Home (4)
- Painted Home (5)
- Painted Home (6)
- Painted Home (7)
- Painted Home (8)
- Painted Home (9)
- Painted Home (Pack 1)
- Painted Home (Pack 2)
- Painted Home (Pack 3)
- Painted Horse
- Pairs of Bowling Shoes
- Palm Springfield Resort
- Palm Tree 1
- Palm Tree 2
- Panic at the Silo
- Panini Press
- Panther Marge
- Papyrus
- Parachute Target
- Parade Roller
- Parade Roller Bundle
- Parade Roller Station
- Parade Train
- Parade Train Bundle
- Parade Train Station
- Paradox Reality
- Paramours of Christmas Past
- Parasite House
- Parcology
- Parental Guidance
- Parents' Island Gate
- Paris Hotel
- Paris Texan
- Park Engineer
- Park Ranger
- Park Visitor Bundle
- Parked Hover Car
- Parking Garage
- Parking Lot
- Parking Lot (disambiguation)
- Parking Lot Lot Lot
- Parking Meter
- Parks and Decapitation
- Part and Parcel Postal
- Parthenon
- Participation Ribbons
- Partner in Grime
- Party Elephant
- Party Hats
- Party Limo
- Party Woes
- Pass, Puff, Puff
- Pass, Puff, Puff Intro
- Pasta Bowls
- Pastel Picket Fence
- Patches and Poor Violet
- Patio Table
- Patriotic Box of Fireworks
- Patriotic Homer
- Patty
- Paul Bunyan
- Paul Flart
- Paula
- Paula's House
- Pave Paradise
- Pavement
- Pavilion Tent
- Peace, Love, D'oh!
- Peace, Love, and Quiet,
- Peace Marker Ray Gun
- Peace Was Never an Option
- Peaceful Groovy Feeling
- Peacock Lounge
- Peak Performance
- Peanut Cart
- Peek-At-Em Park
- Peek-At-Em Park (quest)
- Pelts
- Pennants
- Penny-Wiseguys Promotional
- Penny Fountain
- People Catcher Truck
- Peppermints
- Perfect Beer Truck
- Perfect Game Balloon
- Personal Intel
- Personal Liability
- Personal Liability Attorney
- Personalized Talking Astrolabe
- Pet Cemetery
- Pet Cemetery + Zombies
- Pet Costumes
- Pet Mutant Plant
- Pet Mutant Seedling
- Pet Snake
- Peta
- Peter D'Abbruzio
- Petroleus Rex
- Petting Zoo Awning
- Pharaoh's Sarcophagus
- Pharaoh Guard
- Pharaoh Skinner
- Pharaoh Tent
- Pharaoh Throne
- Pharmaceuticals
- Philip Hefflin
- Phineas Q. Butterfat's
- Phone-Henge Kiosk
- Phone Booth
- Phone Booth (old)
- Phones
- Phoning It In
- Physician, Heal Thyself
- Pickaxes
- Pickaxes (2018)
- Picket Fence
- Picnic Spot
- Picture on a Rembrandt
- Pictures of Paintings
- Pie-apult
- Pie Bomb
- Pie Man
- Pie Man Epic Statue
- Pie Wall
- Piece-of-crap Car
- Pier Section
- Pies and Explosives Pile
- Pies for Guns Booth
- Pig Balloon
- Pig of Paradise Pen
- Piggly's Super Smorg
- Pile of Presents
- Pile of Snow
- Pillow Talk
- Pimento Grove
- Pin Collector Lisa
- Pin Pal Apu
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