Before /win/ closes down again, I also want to share an even less intuitive feature of English: homographs that are pronounced differently based on word class.
For example, verbs in English regularly take the -ed ending for their past tense and participle conjugations, but there are also several words where an identical ending was historically used to create adjectives. For whatever reason the latter remain fully enunciated while the former has been simplified, and due to even more historical happenstance there now exist several words that are written the same but pronounced differently depending on what role it is fulfilling:
Cursed = cursid, or curs't
Blessed = blessid, or bless't
Other pairs are learned, crooked, but it seems winged, supposed, and peaked have been neutralized. Something weird's going on with alleged, it seems that one's actually a new development by analogy. Then there's the similar naked, ragged, rugged, wicked, jagged, legged which I'm not confident in grouping here, and the cases of beloved and sacred where the original verb is obsolete and only the adjective remains. This still overlaps with common participles being used as adjectives, like bored from bore, which has a regular pronunciation.
Then there's <-ate>, which can be either /eɪt/ or /ət/. The verbs it's present in always have a long vowel, while with adjectives and nouns it's a tossup, no way to tell as far as I know. Richard Eaton, some 80 years old historian I just learned of, says Persianate with a schwa, while Latinate I've seen listed mainly with FACE even though you'd expect them to sound the same given how similar they are. (A younger speaker does use FACE for both.) It's possible /eɪt/ is becoming more common over time and as the spelling that makes sense, and which regularly applies to all chemicals bearing it.
Here some pairs you can find are graduate, incarnate, duplicate, correlate, (in)discriminate, elaborate, laminate, deliberate, federate, initiate, intermediate, moderate, and syndicate. Apostate appears to be pronounced both ways, maybe, but I don't know if that's tied to word class. I'm sure there are more though.
The most interesting one are those that are actually derived from each other. English has a method to derive nounds and adjectives from verbs, which consist of moving stress towards the start of the word. Take this set of original verbs: disCOUNT, inSULT, and imPORT, whose stress-derived nouns are DIScount, INsult, and IMport. In fact, the shifted DIScount is an adjective, too. It's called a SUPRAFIX 'cause it's suprasegmental i.e. it's not a specific phoneme but rather something that goes on top, though due to anglo phonetics shifting stress does cause the phonemes to change but the stress being moved comes first and that's what matters!
It's the most populous group, and productive too it would seem, here's a list of them:
https://en.wikipedia.org/wiki/Initial-stress-derived_noun#ListOh, and for some reason "mouth" the verb isn't written as <mouthe> even thought it's /maʊð/, like loathe, bathe, lathe, seethe, lithe, writhe, etc., so that one's another weird homograph. Might have to do with /aʊð/ being an exceedingly rare sequence.
On the flipside, you have a peculiar ending that's pronounced the same but written differently: -tre/-ter, and -bre/ber. I'm not sure what the fuck happened here exactly, looks like something to do with the unstressed /r/ there dangling at the end being deleted off the map or some shit, which in rhotic dialects resulted in a schwar /ɚ/ that sounds exactly the same as <-er>, also /ɚ/. It must've merged or something, both ways of writing it were common across the Pacific before dictionaries fixed them in place. You can see it respelled in entre->enter, but retained in entry, entrance. Also compare tiger with tigris, monster with monstruous, and member with membrane. Anyways, there's centre/center from centrum, fibre/fiber from fibra, and sombre/somber from... sombre, sub-umbra.
Others are spelled with <-er> across all orthographies, like the first group of comparisons above, or chapter, fever, September, October. Inversely, ogre. The respelling was spared in <-cre> because <-cer> would make it sound like /sə/ rather than /kə/, as in acre, massacre, and mediocre. This may all stem from French bullshit, their final <-e> is mute and if you look at words ending in /-tʁ/ like mètre, théâtre, litre, lettre, the loaning languages add vowels where they feel like it, if at all. Seems like a huge chunk of <-re> endings come straight from frogs, whereas original <-er> in root words like anger and water, or any suffixing of comparatives, agents, and the like, are of Germanic origin.