Etymology
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regard (n.)

mid-14c., "a consideration; a judgment," from Old French regard, regart, from regarder "take notice of," from re-, here perhaps an intensive prefix, + garder "look, heed," from a Germanic language (see guard (n.)).

Meanings "a look, appearance; respect, esteem, favor, kindly feeling which springs from a consideration of estimable qualities" all are recorded late 14c. Phrase in regard to is from mid-15c. (Chaucer uses at regard of).

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regard (v.)

mid-14c., regarden, "consider" (that something is so or a certain way), from Old French regarder "to look at, take notice of," from re-, here perhaps an intensive prefix, + garder "look, heed," from a Germanic language (see guard (n.)).

Sense of "consider of importance or interest" is from 1510s. Meaning "look upon, observe" is from 1520s, as is that of "observe a certain respect toward." From 1610s as "look upon" (with a certain feeling), "have or show a certain feeling for." Related: Regarded; regarding.

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self-regard (n.)

"consideration for oneself," 1590s, from self- + regard (n.).

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regards (n.)

as a closing in letters, "respects, good wishes," by 1775, from regard (n.) in the sense of "esteem, affection" (late 14c.).

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disregard (v.)

"treat as unworthy of regard or notice," 1640s, from dis- + regard. Related: Disregarded; disregarding. As a noun, "failure to regard or notice," from 1660s. Related: Disregardful.

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regardless (adj.)

1590s, "indifferent, not heeding or looking," from regard (n.) + -less. As elliptical for "regardless of consequences, expenses, etc.," from 1872. Regardful is attested from 1580s. Related: Regardlessly; regardlessness.

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reward (n.)

mid-14c., "what one deserves, just desserts," from Anglo-French and Old North French reward, rouwart, back-formation from rewarder (see reward (v.)).

The meaning "return or payment for service, hardship, etc.," also "something given in recognition of merit, virtue, etc., a prize" is from late 14c. Also from late 14c. sometimes "punishment, recompense for evil-doing." The sense of "sum of money in exchange for capture of a criminal or fugitive or for return of a lost item" is from 1590s.

A doublet of regard (n.), reward also was used in Middle English in the senses now given to that word: "a regarding, heeding, notice, observation," also "respect, esteem."

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reward (v.)

c. 1300, rewarden, "to grant, bestow;" early 14c. "to give as prize or compensation," from Anglo-French and Old North French rewarder "to regard, reward" (Old French regarder) "take notice of, regard, watch over." This is from re-, here perhaps an intensive prefix (see re-), + warder "look, heed, watch," from Frankish or some other Germanic language, from Proto-Germanic *wardon "to guard" (from PIE root *wer- (3) "perceive, watch out for").

Originally any form of requital, good or bad, for service or evil-doing. A doublet of regard (v.), reward was used 14c.-15c. in the senses now given to that word: "look at; care about; consider." Related: Rewarded; rewarding.

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*wer- (3)

Proto-Indo-European root meaning "perceive, watch out for."

It forms all or part of: Arcturus; avant-garde; award; aware; beware; Edward; ephor; garderobe; guard; hardware; irreverence; lord; panorama; pylorus; rearward; regard; revere; reverence; reverend; reward; software; steward; vanguard; ward; warden; warder; wardrobe; ware (n.) "manufactured goods, goods for sale;" ware (v.) "to take heed of, beware;" warehouse; wary.

It is the hypothetical source of/evidence for its existence is provided by: Latin vereri "to observe with awe, revere, respect, fear;" Greek ouros "a guard, watchman," horan "to see;" Hittite werite- "to see;" Old English weard "a guarding, protection; watchman, sentry, keeper."

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re- 

word-forming element meaning "back, back from, back to the original place;" also "again, anew, once more," also conveying the notion of "undoing" or "backward," etc. (see sense evolution below), c. 1200, from Old French re- and directly from Latin re- an inseparable prefix meaning "again; back; anew, against."

Watkins (2000) describes this as a "Latin combining form conceivably from Indo-European *wret-, metathetical variant of *wert- "to turn." De Vaan says the "only acceptable etymology" for it is a 2004 explanation which reconstructs a root in PIE *ure "back."

In earliest Latin the prefix became red- before vowels and h-, a form preserved in redact, redeem, redolent, redundant, redintegrate, and, in disguise, render (v.). In some English words from French and Italian re- appears as ra- and the  following consonant is often doubled (see rally (v.1)).

The many meanings in the notion of "back" give re- its broad sense-range: "a turning back; opposition; restoration to a former state; "transition to an opposite state." From the extended senses in "again," re- becomes "repetition of an action," and in this sense it is extremely common as a formative element in English, applicable to any verb. OED writes that it is "impossible to attempt a complete record of all the forms resulting from its use," and adds that "The number of these is practically infinite ...."   

Often merely intensive, and in many of the older borrowings from French and Latin the precise sense of re- is forgotten, lost in secondary senses, or weakened beyond recognition, so that it has no apparent semantic content (receive, recommend, recover, reduce, recreate, refer, religion, remain, request, require). There seem to have been more such words in Middle English than after, e.g. recomfort (v.) "to comfort, console; encourage;" recourse (n.) "a process, way, course." Recover in Middle English also could mean "obtain, win" (happiness, a kingdom, etc.) with no notion of getting something back, also "gain the upper hand, overcome; arrive at;" also consider the legal sense of recovery as "obtain (property) by judgment or legal proceedings." 

And, due to sound changes and accent shifts, re- sometimes entirely loses its identity as a prefix (rebel, relic, remnant, restive, rest (n.2) "remainder," rally (v.1) "bring together"). In a few words it is reduced to r-, as in ransom (a doublet of redemption), rampart, etc.

It was used from Middle English in forming words from Germanic as well as Latin elements (rebuild, refill, reset, rewrite), and was used so even in Old French (regret, regard, reward, etc.).

Prefixed to a word beginning with e, re- is separated by a hyphen, as re-establish, re-estate, re-edify, etc. ; or else the second e has a dieresis over it: as, reëstablish, reëmbark, etc. The hyphen is also sometimes used to bring out emphatically the sense of repetition or iteration : as, sung and re-sung. The dieresis is not used over other vowels than e when re is prefixed : thus, reinforce, reunite, reabolish. [Century Dictionary, 1895]
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