In 1883 David embarked upon a new career as a grocer (a trade that one of his brothers had earlier carried out in the village) and he married Isabella Horne in December 1884. By the 1891 census they were at 'Brae Grocer's Shop and House' (likely on Hillhead Street) and had started a family. During the 1890s, the family's lives changed significantly, as Lundin Mill itself went through dramatic growth.
The grocery seems to have prospered (see advert from 1893 below featured in the St Andrews Citizen and also from 1896 from the Fife Free Press) and the family moved into a large house named "The Mount" at the east end of Woodlands Road. The choice of house name is interesting, as it seems it may have been named after the well-know "Sir David Lindsay of The Mount". This namesake was a herald and poet who lived between around 1490 and 1555, whose family home was The Mount outside Cupar.
"...Lindsay had been a mason to trade, but through an unfortunate accident had been compelled to seek some other means of livelihood. Thirteen years ago he had started an unlicensed grocer's shop, which he had conducted to the best of his ability. Lundin LInks was fast growing into a fashionable and popular summer resort, and would soon be one of the best resorts on the east coast. The present premises were inadequate for the increasing trade, and Mr Lindsay thought it a good opportunity to ask for a license for new premises. A Post Office had been opened this month, and all the trains now stop at the station, while many of the houses on Mr Gilmour's feus were being remodelled, and in some cases reconstructed."
The application was supported by a petition signed by 110 owners or tenants from Lundin Mill and another signed by 58 regular visitors to the village. The license was granted. The new licensed premises in the developing resort did well and the advert from 1903 in the Dundee Evening Telegraph (below) speaks of "high-class provisions" and a "list of furnished houses and apartments". Lindsay was present at the opening of the new Lundin Links Hotel in 1900 and presumably became well-connected in the area. His elder brother Andrew was a school headmaster in Cowdenbeath and was close friends (and golfing partners) with another grocer William Bethune - both being born around the same time in Lundin Mill.
David Lindsay diversified his business interests and, around the turn of the century, began a boot and shoe shop (see above advert), in which one of his daughters worked. He owned multiple shops and houses in the village by 1905 (including Hillcrest and Nellfield behind St Helen on Hillhead Street). David died on 5 July 1914 from a heart attack while still running the grocer shop. He was found dead in the water closet at his home, St Helen. He was only 59 but he had lived through an eventful life, beginning when Lundin Mill was a quiet village of weavers and ending after it had transformed into the fashionable resort of Lundin Links. Incidentally, only 5 days later, on 10 July 1914, another Lundin Links shopkeeper passed away - James Gulland the tailor and clothier. Mrs Isabella Lindsay outlived her husband by 25 years, passing away in 1939.