You can add cay, Deegheea-
Smythe
Fanshaw-ffolkes (Sir Reginald)
In my case, no. “Err” and “air” are the same in casual speech. “Bade” and “bed” are nothing alike.
Thanks for the reply - Do you pronounce the vowel of “Err” and “Air” closer to that of “bed” or “bade”?
Like neither of them, though I suppose it’s marginally less different from “bade”.
Also:
*Jack Soo = actor in sitcom Barney Miller
Also, the formal name of the waterway at Sault Ste Marie is “Soo Locks”
*Ndamukong Suh = Football player, Detroit Lions
*sous = plural of sou, french coin
I’ve come up with:
air
ere
are (as in metric base unit of area)
heir
err
I thought I had 6, but can’t recall the other one. . .
(Jane) Eyre
Éire has two syllables. Plus, the ‘r’ is voiced, even in non-Rhotic dialects, but it is voiced differently from the ‘r’ in all the other words listed. Plus, it’s not an English word, so can only be included if you allow multilingual lists.
Since
Cents
Scents
Sense
Qi and chi (often spelled ch’i) are just two different spelling of the same word. Qi is the Pinyan spelling and ch’i is Wade-Giles. And the pronunciation should be different than the other words. A ch-sound rather than /k/.
However, you could add cay to the others.
I thought it would be easy to do in Chinese, as the language has relatively few valid syllables, and homophones are the norm.
But adding the following constaints: (same tone as well as homophone, must work as standalone word not merely a component of compound words, different character not just different meaning for same character, commonly-used modern word), I only get 6 for shi fourth tone
是 - To be (verb)
事 - Matter, affair (noun)
试 - Try (verb)
市 - Market (noun, usually shichang but can use shi on its own)
室 - Room (noun)
示 - To show (verb, usually part of compound words, but can be on its own)
A few more, following your constraints more or less:
势 - power/influence
释 - explain
誓 - oath
氏 - clan/surname
逝 - pass away
柿 - persimmon
Made it to page 2, did you? 
I tried for about a week. I managed to get that someone fell off a roof and died. Felt like nothing more was needed.
You forgot boor; a discourteous person, as in boorish.
I suggest bore, boar, boor, and maybe Boer. The others are pronounced the same because they’re spelled the same. Also, the bore of a weapon doesn’t have to do with caliber; it’s either the interior of the barrel, or wrongly associated with a method of measuring the size of the interior of the barrel which depends on how many lead balls of that particular size make up 1 pound. I’ve heard a 10 gauge called (erroneously) a 10 bore. Caliber is merely the measurement of the diameter of the bore expressed in hundredths or thousandths of an inch. Even that is suspect though, since .380acp, .357mag, .38spcl, and 9mm (roughly 4 “caliber” per mil) all have the same diameter. A lot of time caliber can be confusing since the bore itself is rarely the only thing measured. Instead, the outside of the bullet or the inside of the cartridge case are sometimes measured, leading to wildly divergent measurements for the same object. A perfect of example of this is the Medusa M47 revolver, which is really nifty if you haven’t seen one before and like that sort of thing. 25 different types of ammo out of 1 pistol.
Boor is not a homophone of bore or boar; it is pronounced with a long o while bore and boar have a short o. Boer has several variant pronunciations and can match either of the others (plus be pronounced somewhat differently).
Since this thread was last active, I did manage to find an example of the same spelling, with four different etymologies: Mole. It’s a small burrowing mammal, or a skin blemish, or a quantity of 6.02*10^23 of something, or a Mexican sauce. Though I think the last of those is pronounced differently.
Just like other examples it comes down to dialect. In casual speech I’d pronounce boor the same as bore and boar. I would pronounce Boer differently, however.
Also:
A massive structure, especially of stone, set up in the water, as for a breakwater or a pier. / An anchorage or harbor protected by such a structure.
First recorded in 1540–50, mole is from the Latin word mōlēs mass, dam, mole
A fleshy mass in the uterus formed by a hemorrhagic dead ovum.
Latin mola, special use of mola millstone.