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Del Mar, CA
Del Mar Racetrack, whose grandstand famously carries the phrase "where the surf meets the turf," was co-founded in 1937 by a group of investors that included Bing Crosby, who reportedly greeted the track's first-ever patron in person at the gate on opening day — a founding story the track and the small coastal city surrounding it have leaned into as a defining piece of local identity ever since. The city's beaches and bluffs, combined with a genuinely small-town village character along Camino Del Mar, have made Del Mar one of the more consistently desirable and expensive small coastal communities in San Diego County, despite a year-round population of under 4,500 residents. The Del Mar Fairgrounds, adjacent to the racetrack, hosts the San Diego County Fair every summer along with the annual horse racing meet, giving the small city a level of seasonal visitor traffic and regional event significance well beyond what its modest size would otherwise suggest. Del Mar's combination of a historically significant horse racing venue with genuine Hollywood-era founding history, dramatic coastal bluffs, and a walkable small-town village center has made it one of the most distinctive and consistently expensive small coastal cities anywhere in San Diego County.
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Rancho Santa Fe, CA
Rancho Santa Fe was originally developed in the 1920s by the Santa Fe Railway as a eucalyptus tree farm intended to supply railroad ties, a plan abandoned once the wood proved unsuitable for that purpose — the railway then pivoted to developing the land as an upscale residential community instead, hiring architect Lilian Rice to design its Spanish Colonial Revival village center. That founding architectural vision has been strictly preserved through decades of continued design-review regulation, and the resulting village core, along with the surrounding large equestrian-zoned properties, has made Rancho Santa Fe one of the most consistently wealthy and lowest-density unincorporated communities in the entire state of California. The community's oversized residential lots, many several acres or larger, support an active equestrian culture, with numerous private horse properties and riding trails woven throughout the area's covenant-protected land, a scale of property size increasingly rare anywhere else within San Diego County's borders. Rancho Santa Fe's combination of a preserved 1920s Spanish Colonial Revival village design, some of the largest and most tightly protected residential lots anywhere in coastal California, and an active equestrian culture has made it one of the wealthiest and most exclusive unincorporated communities in the entire United States.
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