San Mateo
San Mateo stands out with its long history and wide spectrum of neighborhoods. San Mateo is perhaps the most traditional of mid-Peninsula cities. Downtown is one of the few in this area with an established, pre-war feel, and it's larger than most. San Mateo's many pre-World War II neighborhoods have a broad range of styles and prices, and often have aged gracefully. There’s plenty of post-war construction too, from inexpensive tracts to comfortable hillside ranchers, with contemporary as well as conventional architecture. You can even live on the water.
Top end:
San Mateo Park: San Mateo Park, one of the San Francisco Bay Region's most beautiful residential communities, is located on the San Francisco Peninsula, approximately 20 miles south of San Francisco and adjacent to the towns of Burlingame to the north and Hillsborough to the west and south. "The Park," as San Mateo Park is affectionately called by residents, is now a virtual arboretum of native and exotic plants and trees and filled with a treasure trove of period houses of all sizes and descriptions -- turn of the century Queen Annes and Mission revivals, early 20th century craftsman bungalows, plus English Tudors, French Normandies, Colonials and Mediterraneans from the '20s and '30s. Included among these are several landmark homes by such noted architects as George Howard, Jr., Bernard Maybeck and Julia Morgan. Over the years, many of these landmark homes have been splendidly restored to their original glory. San Mateo Park now has a friendly neighborhood feeling with its somewhat whimsical homes and luxuriant vegetation, a relaxed informality. San Mateo Park is a neighborhood where residents still take evening strolls and where children ride their bicycles along the quiet streets. It is this neighborhood feeling, along with the exuberance of its architecture and landscaping, that gives San Mateo Park its unique character and makes San Mateo Park so desirable.
Baywood: Just south of San Mateo Park and perhaps a step down, but still the sort of neighborhood that says you’ve arrived. In fact, I think Baywood is one of the most consistent and consistently appealing neighborhoods on the Peninsula. Built from about 1930 to 1951, homes are large and classic, with manicured yards set on broad, curving streets. The neighborhood has an impressive number of variations on the popular Revival styles including Spanish, Tudor, Colonial, Monterey, Moorish and Norman, and a few that defy classification, as well as plenty of prosperous-looking ranchers. Lots are slightly larger than average, usually from 6000 to 8000 sq.ft., with some quarter acres. Homes are typically close to 2000 sq.ft., often well into the 2000s and occasionally over 3000 sq.ft. Graced with a district of extremely attractive apartment buildings, many of them in the Revival styles common to pre-WWII architecture, near El Camino. Just south of Baywood's apartment and commercial district is a different and less-upscale but still very appealing neighborhood, Parrott Park, post-WWII and more tract-like but with plenty of charm—and entirely flat, unlike Baywood. Both Parrott Park and much of Baywood are within walking distance of San Mateo's fine downtown. The local elementary school, Baywood, is one of the most sought-after in San Mateo.
Aragon: Located between Hobart and Notre Dame, Aragon is a living catalogue of picture-perfect pre-war middle-class homes. Flaws are few and far between, with tree-lined streets and old-fashioned streetlights adding the finishing touches. Even the apartment buildings just off El Camino are handsome and well-maintained, with minimal impact on their immediate area. That’s unusual for San Mateo, and this plus Aragon’s remarkable architectural unity suggests a carefully planned neighborhood. That architecture, while appealing, was something of a throwback even when new. The area was built primarily in the late 1930s, when the typical home was evolving into the stripped-down, sober rancher (like Bohannon’s Hillsdale tract), yet Aragon’s dominant theme is the romanticism of the 1920s and early 1930s. Even Aragon’s Spanish street names are more in keeping with an earlier era that romanticized California’s Mexican heritage.