It looks as if the DEAN family had quite a few records in early Maryland, especially on the Eastern Shore.

MD Calendar of Wills (I didn't copy every reference. Counties began keeping their own records in 1777.)

Wm. DEANE, Kent Co., pr. 30 Aug. 1695. To son Wm., (then) aged 7, at 18, "Middle Branch," & "Deanes Relief" on Lankford's Bay. To daus. Eliza & Jane at 16, "Deanes Adventure." To dau. Tabitha, "The Forest" on Gunpowder R. at head of Salt Peter Creek. To wf. Sarah, exx. Wit. Michael MILLER, Robt. PARK, Stephen WHETSON.

William DEANE, Cox Creek near Hungar R., Dorchester Co. [DO], pr. 13 Mar. 1699. To dau. Eliza. JOHNSON. To wf. Eliza during widowhood. To sons Wm., Richard, John, & Henry. Exs. Wm. TUBMAN & Jon. MEREDITH. Wit. Jno. & Wm. MEREDITH & Michael TODD.

John BARKER, Talbot Co., pr. 19 Apr. 1709. To grandson John ABBOTT & James DEANE...Wit. John DEANES.

Robt. BRUMMALL, DO, pr. 13 Feb. 1709. Wit. Chas. DEANE.

Wm. BATEMAN, Kent, pr. 9 Apr. 1716. Wit. Antho. DANES.

Wm. EDWIN, Kent, made 34? Oct. 1716. Wit. Wm. DEANE.

Thos. HACKETT, Sr., blacksmith, DO, pr. 12 Nov. 1716. Wit. Chas. DEANE.

Michael DEAN, DO, pr. 17 Nov. 1721. All to wf. Eliz., exx. Wit. Wm. SPENCER, Mary HOLLINS, Richard WEBSTER.

Elizabeth DAVIS, Kent, pr. 29 Je. 1723. To husband Henry DAVIS, ex., for life, residue of 200 acres "Dean's Adventure," bequeathed to testator and her sister Jane by their father William DEANE [w. pr. 1695]. Also "Addition," taken up by Michael MILLER & made over by late husband Wm. ROBERTS. At death of husband Henry DAVIS, to son Wm. ROBERTS. Wit. Wm. & Ann DICAS, Ja. CALDER.

Eliz. WILLIAMS, Kent, pr. 17 Mar. 1724/5. Wit. Wm. DEANE.

John DAVIS, Kent, pr. 30 Apr. 1726. To wf. Eliza. & minor sons Edward & John. Wit. Wm. & Katherine DEANE.

Eliz. KEECH, St. Mary's Co., pr. 24 Nov. 1730. Wit. Ann DAINE.

John FOSTER, DO, pr. 22 Mar. 1726. To daus. Rebecca, Sarah, Pheby, Susannah DAWSON, Mary FOOKS, & Ann DEANE. Wf. Mary & son Thomas, coexs. To be bu. Friends Graveyard, Transquaking. Wit. Wm. MURRAY & Thos. & Bartholomew ENNALS.

James DEEN, Somerset Co. [SO], pr. 23 Oct. 1744. To {wife?} Mary, being with child, exx. To unborn child, "Deen's Venture." To bro. Charles, "Gladstone's Industry." Wit. John BEADLEY, Saml. BADLEY, Thos. HUFFINTON.

Henry DEAN, DO, blacksmith, pr. 13 Mar. 1746. To son John, ex., "Broad Ridge," & pt/o "Peaknull" & "Dean's Prevention." To son Henry, pt/o "Peaknull," & pt/o "Little Brittain." To son Thomas, "Rainy Point." To dau. Mary TARGINSON. To wf. Elizabeth. Wit. Wm. ROBINSON, John BROHOM, Jas. BRIGHT.

Wm. ROBINSON, DO, pr. 10 July 1749. Wit. Henry DEENE.

Capwell KING, SO, pr. 17 Oct. 1749. To Jno. DEAN, cattle...

Eliz. SPENCER, Dorset Co., pr. 9 Apr. 1750. To son Wm. DEAN, for life, pl. where he lives, pt/o "Turners Adventer," then to his son Wm. To son Mathew DEAN, ex., pl. where I live. Wit. Thos. & Andrew GRAY & Francis HENRY.

Rebecca HOWARD, DO, pr. 10 Je. 1760. Wit. Wm. DEAN, Jr.

Henry LAKE, DO, pr. 7 July 1760. Wit. Wm. DEAN, Jr.

Elizabeth DEENE, DO, spinster {?}, pr. 2 May 1763. To son John. To grandch. Geo., Mary, & Eliz. FERGUSON. Residue to son Thomas, ex. Wit. Matthew KEENE & Benj. KEENE, Sr. & Jr.

David MELVILL, DO, pr. 20 Sep. 1762. Wit. John DEAN, Jr.

Charles DEAN, SO, pr. 11 Sep. 1764. All to wf. Sarah for life. Then to son Charles, dwelling pl. with 100 acres, but if he dsp, to son Noble. To son James, land on the uppermost side of Walters Road, but if he dsp., to his other bros., except five acres to John BADBY. To Abraham DEAN. To son Levie, 70 a. adj. Ephraim DEAN's 100 acres to be divided between his bros. {?} Wit. Levin LUNGS, John HUFFINGTON, Wm. BADBY. Widow made election.

William DEAN / DEEN, DO, 18 Feb. 1760, 29 Mar. & 2 Apr. 1764. To wf. Sarah, exx., & ch. Wm., Henry, & Rachel DEAN, Eliz. CANNON, Mary GRAHAM, & Rebecca ROSS. To granddaus. Delilah & Sarah DEAN. Tracts "Northampton" "Dean's Choice," & "Andrew's Fortune." Wit. Robt. SCOTT, Wm. ROSS, Summers ADDAMS.

Lewis GRIFFITH, DO, pr. 6 May 1765...Wit. Wm. DEAN, Jr., John GOOTEE, Jr., Wm. EAGER, Jr., Richard LANE.

Elizabeth GRIFFITH, DO, pr. 9 Mar. 1770...Wit. Henry LAKE, Richard DEAN.

John SAFFORD, DO, 12 Aug. 1772...Wit. Wm. DEAN, John WINGATE, John SCOTT.

William DEAN, DO, pr. 15 July 1774. To eldest son James, coex., & second son __, all land after death of wife Elizabeth, coexx. To daus. Mary WOODLAND, Rhode DEAN, & Sarah MOORE. Wit. Robt. SCOTT, Benj. TODD, Wm. LANGRAL. Widow made election, & James renounced executorship.

George BOOZ, DO, pr. 28 Mar. 1777...To Godson George DEAN, "Previlidge," "Brambles Hope," "Coles Regulation," & land west of Harrisses Gut. Wit. Wm. DEAN, Wm. GEOTEE, Andrew GOOTEE.

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WATCH OUT! Here comes speculation. It looks as if the James DEEN who had died by 1744 in Somerset Co., listing an unborn child and a brother Charles could have been a brother of Charles DEAN whose will was pr. 1764, naming a son James DEAN and also several others named DEAN.

I wonder if Elizabeth SPENCER, will pr. 1750, naming sons Mathew & Wm. DEAN, might have been the widow of Michael DEAN, will pr. 1721, since a witness to Michael's will was Wm. SPENCER. The son Wm. DEAN & grandson Wm. DEAN might have been the ones whose wills were pr. 1764 & 1774.
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There are a few references to James DEAN in the online files of the MD Archives:

26 Apr. & 16 May 1799, James & wf. Mary DEAN to James SMITH, pt/o "Townsends Situation" [SO now WI, L:449-450].

1803, #155. Abraham TAYLOR & Isaac KENNEY vs. James DEAN, SO, Deans Outlet to Jones Lot. Plat also shows Kenneyington. 1:28:02:046.

Chancery #1350, 24 July 1819. Gilbert, Eliza, Joseph, & Walter DAVIS, George & Catherine GEBHART, Sarah RADCLIFFE & James DEAN vs. George & Denton DAVIS, Grace, Catherine, & Noll CANNON, James, Mary, Joseph, Eliz., Wm., Joshua, Thomas, & Upton RADCLIFFE, Barney, Catherine, Thomas, & Joshua DEAN, & Alexander & Sarah HARVEY. Estate of Joseph RADCLIFFE, Rights of Man. Accession 17,898-1350 MSA S512-2-1406.

#11385,2 Dec. 1841. Wm. W. TWILLEY vs. Whittington, James, Wm., Mary, Cassandra, Wm., Thomas, & Sophia DEAN, Edward & Susan WILLING, Leonard & Eliza BOOZE, Ephraim & Eliz. MARVEL, James D., Wm. D., John D., Leah D., Levin, Slater, Julia A., Mary, Sally, Louisa, & Thomas TWILLEY, DO, estate of Charles DEAN, "Gootees Neck." Accession #17,898-11385, MSA S512-14-11210.

Do any of the names appear with James DEAN of Kentucky?