 If you liked
Kimagure Orange☆Road
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 ...then you might like
Maison Ikkoku
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These series are almost identical, as both are long, classic, old school romantic comedies with a slice of life mood.
Expect the average foolish male protagonist, the beautiful black-haired tsundere, the super annoying schoolgirl in love with the main guy, funny/silly/annoying supporting characters, love triangles, misunderstandings, a nice OST, and 80's style.
The main difference is that Maison Ikkoku's main characters are older than the Orange Road ones.
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Recommended by RenaPsychoKiller
This are good examples of a old school romantic anime, they are very similar and can give us the entertainment and the joy of a great romance
Both are early classics, lengthy romantic comedies in a harem-esque style featuring a male lead and a cast of women. Both will make you laugh and cry. KOR is only half the length of MI, but still weighs in at a respectable 48 episodes, and features the BEST ending of any anime I have watched. These two anime set the standard for romantic comedies, and precious few of what has come after ever matched that oh-so-high bar.
Both are 80s anime, with good soundtracks.
Both have fairly similar pacing and plot progression.
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Recommended by brokenbutwhole
Both series have a similar female main character: Kyoko Otonashi from Maison Ikkoku and Madoka Ayukawa from Kimagure Orange Road. They're both attractive and have similar personalities. They also have similar male main characters. So if you love one then you might also love the other.
Maison Ikkoku doesn't have any supernatural elements and it's not as episodic as Kimagure Orange Road but if you love a great romance series with an amazing soundtrack accompanying it (personally think KOR has the better OST) then I highly recommend watching the one you haven't watched already.
Both are oldschool rom coms about the typical bumbling awkward guy in a love triangle with a mysterious older woman and a more available/clingy younger woman. 'KOR' has mild fantasy elements in the form of some magic powers, but they don't dominate the show. They're mostly just there to get them out of corners they write themselves into.
Both are generic 1980s animés featuring love triangles,slowly developing relationship between a tsundere female lead character and an average struggling male protagonist and funny but helpful supporting characters. Both series have the some of the best OSTs and background music score in all of anime history. Unlike many animes both series have clear endings. Both series are influential, directly or indirectly inspired dozens of animes.
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Recommended by tysonfist764