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Q: What words have four or more spellings that sound alike?

A: Starting with each phoneme:

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 <sw>: I, a, aah, o, of, ugh (6)
 a: air/ayre, are, Ayr, e'er, ere, err, eyre, heir (8)
 <a_>: a, ae, ay, aye, eh (5)
 <a">: ar/r, are, or, our (4)
 <a.>: apercu, apercus (2)
 a<u.>: hour, our (2)
 b: braes, braise, brays, braze, breys (5)
 ch: Chile, chili, chilly (3)
 d: daos, dauws, dhows/dows, dows, dowse, taos (6)
 e: air/ayre, are, Ayr, e'er, ere, err, eyre, heir (8)
 <e_>: ease, es, he's (3)
 f: fain, fane, feign, foehn; faize, faze, feaze, phase (4)
 g: gild, gilled, guild (3)
 h: hays, hayes, haze, hes/hehs, heighs, heys (6)
 hw: wheel, wheal (2)
 i: improvisatore, improvisatori, improvisatory (3)
 <i_>: ai, ay, aye/ay, eye, I, i (6)
 j: gest, geste, jessed, jest, just (5)
 k: caught, cot, cote, cotte, kat/khat/qat/quat/cat, Kot; crews, cruise, crus, cruse, krewes, Krus (6)
 <k_>: challa, hallah (2)
 l: lais, lase, lays, laze, leas/leys, leis (6)
 m: mhorr/mohr, moire, moor, mor, more (5)
 n: nae, nay, ne, nee, neigh (5)
 <ng>:
 <o_>: eau, eaux, haut, O, o, oh, owe (7)
 <o.>:
 <o.>i: Euler, oiler (2)
 p: peak, peek, peke, pic, pique (5)
 r: raise, rase, rays, raze, reis, rees, rehs, res (8)
 s: cees/ces/cs, psis, seas, sees, seize, sis, szis; scissel, scissile, Sicel, sisal, sisel, sissle, syssal (7)
 sh: chou, shoe, shoo, shu (4)
 t: tai, taille, Thai, tie, tye, Tyigh (6)
 th: threw, thro, through (3)
 <th>: their, they're, there, thir (4)
 <u">: ooh, ow, phew, whew, who (5)
 <u.>: oops, whoops, woops (3)
 v: vane, vain, vein (3)
 w: weal, weel, we'll, wheal, wheel (5)
 y: ewe, phew, u, yew, you (5)
 z: czar, tsar, tzar (3)
 zh: giro, gyro (2)
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               *
Unless noted otherwise, all words occur in Webster's Third New International
Dictionary, Merriam-Webster, Springfield, MA, 1961.
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