Pleasanton, California

The Most Desperate Town in the West

Looklyloo Score: 89

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Young Professionals/Empty Nesters/Retirees

Pleasanton is not a hub for young professionals but if you need to live here for a short commute then make sure you live Downtown. It’s the spot for restaurants, pubs/craft breweries, cafes and everything else you can find to do here. It’s also where the bulk of the apartment/condo buildings are going up. Plenty of one and two-bedroom options with gyms and pools to stay fit and cool throughout the year. Downtown parks like Lions Wayside and Delucchi offer courts for play and run and plenty of sports leagues including: basketball, softball, tennis and even Bocce!

There are also small older homes in the downtown area for young families, couples and empty nesters/retirees who crave a downtown lifestyle but in a quieter city.

Vintage Hills


Vintage Hills is a lovely neighborhood, just east of Downtown, perfect for younger families looking for kid-friendly blocks and midsize, more affordable homes than the country-club neighborhoods of Ruby Hill or Castlewood. One of the nicest features of the neighborhood are the pretty hills and trees that keep things cool and give residents beautiful views of the area. You get the excellent schools of Pleasanton and a better value than some of the other neighborhoods, particularly if you like the easy access to the downtown social life.

Ruby Hill


Ruby Hill is a luxury neighborhood with beautiful, relatively newer homes, many of which surround the Jack-Nicklaus-designed Ruby Hill Golf Club. In addition to the highest-end homes, and the nicest golf club in the city, you also get perks like community center that includes a fitness center, swimming pool and tennis courts. Pair this lifestyle with parks/trails for outdoor play and some of the best public schools in the area and you can see why families pay the price for homes in Ruby Hill.