Artists often measure out their lives not with coffee spoons but with quite everyday happenings, some of which are beyond their control and some of which are conscious.

Victoria Crowe's life has been like that. Not long after moving in 1968 to Scotland from London, where she was born on VE Day, she and her husband took a lease on Monksview at Kittleyhowe, a mile east of Carlops on the northern fringes of the Borders.

With the Pentland Hills, where Robert Louis Stevenson loved to tramp, on her doorstep, and neighbours distant and self-contained, Crowe began to paint what she saw when she looked out of her window and when she wandered across a landscape that may be lacking in drama but, especially in winter, offers what's tantamount to a blank canvas. Pewter-coloured skies; fields suffocated by snow; bare, leafless trees poking like skeletons out of the bone-hard earth; solitary figures going about their business: it was a scene primeval in its emptiness, timeless yet capturing a moment when elsewhere the world was in turmoil and the Swinging Sixties were beginning to lose their momentum.

One of Crowe's many paintings from her time at Kittleyhowe is simply called Snowbound Cottages. It reminds one of Andrew Wyeth's paintings of Kuerner Farm, a place that did not seem immediately picturesque but which demanded an emotional, abstract response from the artist. Something similar is going on in Snowbound Cottages, where the snow barely covers the stubbled fields and the trees are having trouble staying upright and the sky looks angry and ominous and ready to release its load, like a bomber over Dresden.

It was at Kittleyhowe that Crowe was introduced to Jenny Armstrong, who was then in her sixties. Living alone, she was, as Duncan Macmillan notes, the daughter and grand- daughter of shepherds, and had at one time run 2000 sheep on the Pentlands – which, in a pre-mechanised era, was a challenging job. When Crowe met her, Armstrong still tended a small flock and kept a few hens. The two women became friends and the shepherdess soon featured in the artist's paintings.

"Jenny Armstrong's life was a little like that of a medieval saint or hermit," writes Macmillan. "For her, however, this was simply practical and not a sacrifice made in the name of the doubtful rewards of religion, though she went to the kirk..." In a series of paintings, Crowe insinuated Armstrong into the land, as if she were a natural element. Later, when Armstrong had lost both legs and could no longer get out and about, Crowe turned her attention to the interior of her cottage, placing the now housebound shepherdess amongst the clutter of ordinary household objects, as she had once put her among hills and trees and fields.

Kittleyhowe, however, is just one amongst several fecund episodes in Crowe's career. Her early work, as Macmillan acknowledges, was in part influenced by her Catholic upbringing, and religion and spirituality has been a recurring theme. For a spell she was interested in Russian iconography and when she was just 20 painted a remarkable self-portrait in which she is depicted alongside a head of Christ by Andrei Rublev. Later, following her paintings of Jenny Armstrong, she received a number of commissions for more formal portraits, including ones of Winifred Rushforth, the first person to practise psychoanalysis in Scotland; RD Laing, the unconventional psychotherapist; and poet Kathleen Raine.

Intriguing though they are, and very beautiful (a word frequently – and not unreasonably – associated with Crowe), they are eclipsed by one of her son Ben. Called Heroes and Villains, after the song by The Beach Boys, it shows Ben, who died of cancer while at university in Aberdeen, in the kind of short-sleeved shirt you might wear on a surfing holiday. He is staring distantly into the room, his expression impassive, his pose statuesque, classical. Behind him lie various objects, including a toy soldier in a kilt and busby, a postcard with the infant Christ and a lamb. Framed in the window is an aeroplane out of which half a dozen parachutists have jumped, recreating, says Macmillan, an exercise that actually took place in the Pentlands during the first Gulf War. All of life is contained in this picture – its randomness, innocence, uncertainty, eccentricity, vibrancy, history and irony. We are alone yet not alone, islands unto ourselves, independent beings but also part of a past that is full of baggage, full of conflicting and contrasting memories, assailed by the inexplicable.

Such is the power of Crowe's work. A belated visitor to Italy in general and Venice, where she has a studio, in particular, her later paintings contain echoes of Uccello, Piero della Francesca, Raphael and Bellini. More recently, she has drifted away from portraiture and back towards landscape, with two quite stunning paintings, Blue Snow and Fiery Trees and The Shortest Day. Both are reproduced in this overdue book, which is the best alternative to owning the real thing.

Duncan Macmillan

Antique Collectors' Club, £35

Victoria Crowe