Llwyn-y-Maen was the stem seat of the Lloyd family who, in the sixteenth and seventeenth centuries, were a prominent north Shropshire family, with branches settled at neighbouring Llanforda (q.v.) and at Drenewydd near Whittington (see Brogyntyn, q.v.).

The Lloyds descended from Madoc ap Meredith, Prince of Powys (d. 1160), whose son, Einion Evell (1135–1196), was recorded living at Llwyn-y-Maen. Einion’s descendant, Ieuan Vychan, Constable of Knockin Castle (fl. c. 1250–1300) inherited both Llwyn-y-Maen and Llanforda which passed to the Lloyd family following the marriage of his daughter and heiress, Annesta, to Meurig Lloyd.

Meurig refused to submit to English Marcher law in the reign of Edward I and, when Officers of the Crown were sent to Dyffryn Clwyd, Meurig killed one of the judges together with other officers, who he then hanged on the oak trees in Uych Dulas. His lands were confiscated and he fled to the sanctuary at Halston (q.v.), placing himself under the protection of John FitzAlan, Lord of Oswestry. In Richard I’s reign, Meurig became a general in the army at the Seige of Acre in Asia in 1191, where he showed great valour in regaining the Emperor of Austria’s standard. As a consequence, he was given the right to use the Austrian double-headed eagle in his coat of arms.

Meurig and Annesta’s descendant, Robert Lloyd (d. 1508), married a daughter of John Edwards of Plas Newydd, Chirk, and it was he who divided Llwyn-y-Maen and Llanforda; the latter passing to his eldest son, John (d. 1579), and the former passing to the younger son, Captain Edward Lloyd. Edward was Constable of Oswestry Castle and Captain under Earl FitzAlan at the siege of Boulogne in 1544, and he married Elizabeth, daughter of Richard Stanney of Oswestry.

At the time of the Civil Wars, Llwyn-y-Maen was owned by Colonel Richard Lloyd, Royalist Governor of Oswestry Castle, and Richard Lloyd ‘of Lloyd-Armain, Esq.’ was compounded for £480. The property thereafter passed to his son Edward (d. 1687), a Captain in the Royal Army. Two generations of Richard Lloyds followed, and the latter’s son Edward Lloyd (1698–1764) of Llwyn-y-Maen served as Mayor of Oswestry in 1727.