There are about eight houses in the Hundred Acre Wood. Tigger originally lived with Kanga and Roo, but was sometime given his own in The Tigger Movie. There's Pooh's house, Piglet's House, Owl's House, Rabbit's House and Rabbit's garden, Gopher's House with a series of tunnels, Tigger's House, Eeyore's House, Kanga and Roo's House.
Pooh Sticks Bridge: a wooden or cobblestone bridge above the river where everyone engages in the game of Pooh Sticks.
The Enchanted Place: a very special almost sacred place where Pooh and Christopher Robin go to say goodbye as Christopher Robin must attend school at the end of The Many Adventures of Winnie The Pooh. In Pooh's Grand Adventure: The Search for Christopher Robin, it is replaced with a tree on a curved hilltop. It appears less special as other characters treat it like it was a normal tree.
Eeyore's Gloomy Place: where Eeyore's House is made of sticks. Most characters are seen hurrying past it and knocking it over (even Christopher Robin) it isn't shown explicitly until the 2011 film, Winnie the Pooh. When it was the place that Pooh discovers Eeyore's tail is missing, it appears dark with many overgrown plants and trees blocking sunlight.
Christopher Robin's house: Described as a "Green Door in a Tree", but in most media it appears in the Hundred Acre Wood. Many think it is the portal to the Hundred Acre Wood. In The New Adventures of Winnie the Pooh his house is on a street in America (Judging by his mailbox which has USPS on it) named Hundred Acre Road. In The Many Adventures of Winnie the Pooh and the 2011 Winnie the Pooh film, his yard is full of toys.
Gopher's Tunnels: a series of tunnels beneath the Hundred Acre Wood. In The Many Adventures of Winnie the Pooh, it is shown he is prone to falling into them. In the New Adventures of Winnie the Pooh, where they are prominently shown, they are simple mining tunnels supported by wooden beams.
Heffalump Hollow: is the home of the notorious Heffalumps. Originally, the area was forbidden to enter and bordered off from the rest of the woods by a fence. Eventually, Pooh and his friends made peace with the Heffalumps (thanks to Lumpy) and the location was no longer forbidden.
In the Kingdom Hearts series, the Hundred Acre Wood is called the 100 Acre Wood. It is simply a magic book containing the world that Merlin keeps with him. In most games (with the exception of Coded, 358/2 Days, and Dream Drop Distance) it is optional, but beneficial to visit the 100 Acre Wood. It is special in both Kingdom Hearts and Kingdom Hearts II as a world within a world. When Sora enters the book, he lands on a version of the flat map of the 100 Acre Wood. Classic locations such as Winnie the Pooh and Piglet's House are accessible, as well as the Muddy Path and Spooky Cave, making this world one of very few to show a change of day. Each location usually harbors a mini-game with prizes which help Sora, Donald, and Goofy on their journey, although Sora is the only one that goes into this world.
When Merlin drops the 100 Acre Wood book while walking home, Terra picks it up and returns it to him, who says he has never seen it before. He leaves it in his house for Terra, and later invites Ventus and Aqua in to read it when they pass by. After it is returned, the three main characters can read it to unlock their hidden powers, visualized as the Honeypot Board.
Cid first gives the book to Sora to give to Merlin, who tells Sora that there is a world within the book. He mentions that Sora needs to collect Torn Pages throughout the worlds until he finds and seals the 100 Acre Wood's Keyhole. When Sora first goes into the book, he meets Winnie the Pooh, who is the only one left in the book. Along the way, he finds and makes friends with each of the 100 Acre Wood's inhabitants, with whom he plays a Christopher Robin-like role.
The 100 Acre Wood appears in Sora's second set of World Cards, and can be accessed on the seventh, eighth, ninth, or tenth floor of Castle Oblivion. When Sora enters the world, he finds Pooh all alone, and decides to go down the path with the teddy bear in order to find his lost friends. Upon going down the path, Sora and Pooh find Rabbit picking up cabbages, and get Owl's attention by having Pooh float high in the air with a bundle of balloons, brought back to the ground by Owl. Sora and Pooh find Roo in a hole after Pooh falls into it, and find Eeyore later down the path, whose tail is knocked down from a tree that Pooh, being chased by bees, runs in to. Tigger's attention is captured when Pooh is taught by Sora to bounce on tree stumps in a similar to formation to Tigger. Shortly afterwards, Sora and Pooh are bombarded by Rabbit's cabbages, which come rolling down the hill. Sora knocks the cabbages into a stack with the Keyblade, which causes Rabbit to appear. Rabbit explains that he tried rolling the cabbages down the path, since someone had broken the cart he had planned to use to bring them down. Coincidentally, it was Sora and Pooh who broke this cart. Sora and Pooh soon afterwards arrive at the end of the path, with all of Pooh's friends found. The two say their parting words, and Sora leaves to continue climbing to the top of Castle Oblivion.
When Merlin moves to Hollow Bastion, he takes the book with him. When Sora returns, he excitedly enters the book to check up on his friends. While he is greeting Pooh, he is suddenly ejected from the book as the Heartless try to steal it. During the battle to recover the book, it is damaged. Upon return, Sora finds Pooh with severe amnesia, unable to remember him and all of his other friends. Sora then goes out to find Torn Pages which slowly restore Pooh's memory of his friends while continuing his quest to find Riku and King Mickey. Shortly after fully repairing the book, Sora admits that he has to leave again, but reassures Pooh that they will always be in each other's hearts. Once all five Torn Pages have been located, the book's cover is changed to a picture of Sora and Winnie the Pooh sitting on Starry Hill together.
The hill at night from the Hundred Acre Wood in a background from the opening intro/closing credits of every season and episode plus the pilot, Pooh Oughta Be In Pictures and Sing a Song with Pooh Bear (and Piglet Too).
The hill at sunset from the Hundred Acre Wood in a background from the closing credits of Season 1 of every episode only.
The Hundred Acre Wood was inspired by Ashdown Forest in Sussex, England.
In the original Milne books, the Hundred Acre Wood was merely a section of the unnamed forest and was where Owl lived. It was inspired by Five Hundred Acre Wood in Ashdown.
The wood's weather in Christopher Robin seems to be somewhat symbolic, as it was shown with fog after Christopher choose his work over his family, while it got worse when he yelled at Pooh, but when he began to slowly act like when he was a child, it was shown clowdy instead of foggy, and when Christopher admits to Pooh that he has lost his way in life, it was shown more sunny and in later scenes, it is completly sunny. In simple words, the wood's weather symbolises Chistopher Robin's character devolpment.
In most Kingdom Hearts games (with the exception of Coded and 358/2 Days), visiting the Hundred Acre Wood is optional but beneficial if you wish to complete the journals.
In Kingdom Hearts: Birth by Sleep, Terra, Ventus and Aqua don't visit the Hundred Acre Wood, but if they choose to look at the book, an extra board for the Command Board game is available. Pooh and Tigger are the opponents should the player choose to play in the game.
The Hundred Acre Wood is the scene in the first Kingdom Hearts bonus comic.
In Kingdom Hearts II, there are several references to other Winnie the Pooh films. If the player returns to Piglet's House after completing the level's mini game storywise and talks to Gopher, Gopher will mention Piglet's bravery when rescuing Pooh from the log in Piglet's Big Movie. If the player returns to Kanga's House after completing the level's mini game storywise and talks to Roo, Roo will mention Tigger teaching him the Whoop-de-Dooper Bouncefrom The Tigger Movie. Also, the many boxes around Kanga's House are those seen in Piglet's Big Movie. If the player returns after completing the Hundred Acre Wood, and speaks to Roo, Roo will mention meeting a new friend, referring to Lumpy from Pooh's Heffalump Movie.