A handful of decisions illuminate the operation of the statutory scheme and the boundary between legal and equitable interests.
Tulk v Moxhay (1848) established that a restrictive covenant can bind successors in title in equity. The plaintiff sold part of Leicester Square to the defendant's predecessor, who covenanted not to build upon it. The land was sold on; the defendant, a subsequent purchaser, sought to build. Lord Cottenham LC held that a purchaser with notice of a restrictive covenant takes subject to it: 'it is said that, the covenant being one which does not run with the land, this Court cannot enforce it; but the question is, not whether the covenant runs with the land, but whether a party shall be permitted to use the land in a manner inconsistent with the contract entered into by his vendor'. This equitable doctrine, later codified as a Class D(ii) land charge in unregistered land and protectable by notice in registered land, became the foundation of private planning control.
Walsh v Lonsdale (1882) established that an agreement for a lease, if specifically enforceable, creates an equitable lease as good as a legal lease 'in equity'. The plaintiff was granted a seven-year lease by parol (oral agreement) but no deed was executed. The defendant landlord sought to distrain for rent calculated on a different basis than the oral agreement stipulated. Jessel MR held that 'there is an agreement for a lease… and in equity a lease is as good as a lease… [The plaintiff] holds, therefore, under the same terms in equity as if a lease had been granted'. This principle underpins estate contracts generally: once a valid contract for the sale or lease of land exists, equity regards the purchaser or tenant as owner in equity, subject to completion.
City of London Building Society v Flegg (1988) clarified the scope of overreaching. Mr and Mrs Flegg contributed to the purchase of a house conveyed into the joint names of their daughter and son-in-law, thereby acquiring equitable interests under a resulting trust. When the daughter and son-in-law mortgaged the property, the Fleggs argued that their rights as persons in actual occupation bound the mortgagee. The House of Lords held that the interests were overreached under s 2(1) LPA 1925 because the mortgage advance was paid to two trustees; therefore the Fleggs' rights attached to the proceeds (notionally) and did not bind the land. Lord Oliver emphasised that overreaching is mechanical: if the statutory conditions are satisfied, it operates regardless of occupation or notice. Flegg is a cornerstone of conveyancing practice: it protects lenders and purchasers who comply with the statutory scheme, but has been criticised for subordinating occupiers' rights to commercial certainty.
Williams & Glyn's Bank Ltd v Boland (1981) (decided before Flegg) held that a wife's equitable interest under a resulting trust, coupled with actual occupation, constituted an overriding interest binding a mortgagee. Mrs Boland contributed to the purchase price but the legal estate was in her husband's sole name. He mortgaged the property without her knowledge. The House of Lords held that her interest was an 'overriding interest' under s 70(1)(g) Land Registration Act 1925 (now Sch 3 para 2 LRA 2002) and bound the bank. Lord Wilberforce rejected the argument that the wife's occupation was merely as shadow of her husband's: 'the house was purchased in part with her money and her right to occupy is in conjunction with the legal owner'. Boland revolutionised conveyancing practice, requiring lenders to make enquiries of all adult occupiers. The contrast between Boland (sole trustee: no overreaching, interest may bind) and Flegg (two trustees: overreaching, interest does not bind) is a staple of exam questions.
National Provincial Bank Ltd v Ainsworth (1965) delimited the category of proprietary interests. Mrs Ainsworth, deserted by her husband, claimed a 'deserted wife's equity' entitling her to remain in the matrimonial home. The House of Lords held that no such proprietary interest existed. Lord Wilberforce (delivering the leading speech) identified four characteristics of property rights: definable content, identifiable in third parties, capable of assumption by third parties, and having some degree of permanence. The deserted wife's right failed these tests. Ainsworth stands for the principle that not every right affecting land is proprietary; personal rights (including contractual licences, barring exceptional constructive trust cases) do not bind successors in title.
Street v Mountford (1985) established the test for distinguishing a lease (a legal or equitable estate) from a licence (a mere personal permission). Lord Templeman held that the substance of the arrangement governs: if the agreement confers exclusive possession for a term at a rent, it is a lease, regardless of the label the parties attach. This remains the leading authority on the lease/licence divide; its implication for the doctrine of estates is that you cannot contract out of proprietary status by drafting subterfuge.
These cases should be at your fingertips. Examiners expect you to cite them accurately by name, year, and principle, and to apply them to novel facts.