Marine Drive was originally the crooked North Arm Trail. In the spring of 1863 the colonial government hired the McCleery brothers to improve and extend it from the population centre at New Westminster to the Mahli and Musqueam villages. They completed the three-month job in June, after which Fitzgerald and Samuel McCleery settled on the Southlands flats. Samuel McCleery's 1891 farmhouse at 2610 South West Marine survived until 1977.

Renamed River Road, the old North Arm Trail became Marine Drive at the dawn of the automobile age, in 1911, when Point Grey municipal council straightened and blacktopped it. Touted as "the greatest panoramic driveway on the coast," Marine Drive was envisaged as part of a scenic loop of Point Grey, with Granville Street, paved from 25th Avenue to Marpole in 1910, forming the north-south leg. One of the early settlers of Marine Drive, at 2250, was a man named W.O. Webster, the Vancouver distributor for Gray-Dort motorcars--the remoteness of the area demanded car ownership, which required money, which ensured exclusivity.

Maple Grove Park at Yew and Marine was dedicated initially as Bowser Park just before World War I, when houses began to appear in the blocks south of 49th Avenue. Point Grey council decided not to remove the enormous stumps left in the park from old logging operations, so that children could imagine the size of Vancouver's original forest.

The first Marine Drive residents purchased acreages and on them built substantial, self-contained estates, often with their own wells and electric dynamos. The earliest was "Southlands," built in 1910 for the wholesale grocer W.H. Malkin on property bounded by Balaclava, Blenheim, Marine and the Von Alvensleben property at 43rd Avenue (now Crofton House). The most remote estate was near the tip of Point Grey, built in 1912 by the lawyer E.P Davis and now known as Cecil Green Park.

The first houses on the "Millionaire's Row'' stretch of Marine between Marpole and Maple Grove Park were erected just west of Yew Street in about 1912-14 for the president and vice president of the Vancouver Lumber Company, John Tucker and his son-in-law Edward Knight. The Tuckers erected the stone-foundationed Arts & Crafts-style house at 2280 South West Marine, partially visible down a long, rhododendron-lined driveway. The Knights' house, at 2326, is a hipped-roof Tudor with very tall chimneys. Both houses are best viewed from the flats below, along Macdonald Street or from the McCleery golf course. Another pre-World War I house is 2194 South West Marine, a Maclure & Fox design for Herbert Barton.

The next set of houses date to the early 1920s. Their occupants were a "who's who" of Vancouver, including George Kidd, the general manager of B.C. Electric Railway, at 2136 (demolished), the Hastings Street clothier William Dick at 2000 (demolished), and Gordon Farrell, the long-time president of B.C. Telephone, in the twin-gabled house at 1890. Blythe Rogers, the eldest son of B.C. Sugar founder B.T. Rogers, built the stylish Tudor originally called "Knole" at the northwest corner of 57th and Marine in 1919, shortly before his death at the age of twenty-six. Down below Marine at 57th Avenue, the Marine Drive Golf Club laid out links on Samuel McCleery's old farm, and farther west at Blenheim Street, the Point Grey Golf Club took over the former Mole farm.

The two houses which established Marine Drive's reputation for a rather garish ostentation were financed by brewery and liquor money in the early 1930s. Harry Reifel's "Rio Vista," a Spanish Colonial Revival house at 2170 South West Marine, with a tessellated "Pompeiian" indoor pool and spectacular gardens, was the first; the larger "Casa Mia" at 1920 was erected for Harry's brother George, the namesake of the waterfowl sanctuary on Westham Island. Another son of B.T. Rogers, Philip, built the French provincial-style mansion at 2010 during what was known elsewhere as the Great Depression.

Subdivisions of the original properties along the Marine Drive bluff have reduced the estate-like quality of the area. On the flats below, reached by following Angus Drive down the hill to the riverbank, new houses occupy land that, until the 1980s, was home to blackberry thickets and some gardeners' cottages and greenhouses for the big homes above. The impression today, looking from the river's edge back towards Marine Drive, is of a row of very large houses set cheek-by-jowl along the ridge--impressive, but a far cry from the old days.