Most of Cupertino’s contemporary properties were developed around 1960. The area between Stevens Creek Boulevard, Miller Avenue, Bollinger Road, and Lawrence Expressway contains 224 Eichler homes, built during the 1950s. Two of the newest parts of Cupertino are among its oldest housing tracts. Monta Vista and Rancho Rinconada were developed outside of the city’s boundaries in the 1950s and before. Rancho Rinconada was annexed in 1999 and the last part of Monta Vista was annexed in 2004. The neighborhood of Seven Springs is at the southwestern tip of Cupertino and was developed in the late 1980s. The newest and most northwestern neighborhood, Oak Valley, borders Rancho San Antonio Park and was developed around the turn of the millennium.
Cupertino is known for its high housing prices as the majority of residential properties are multimillion-dollar homes as of the priciest housing market peak of 2022, with the entry-point into a single-family home at around 2 million dollars in the Cupertino HS area, and the entry point at around 2.6 million dollars in the Monta Vista HS area. Many smaller homes start from the high $2 millions, mid-size homes start from the mid $3 millions, and larger executive homes start from mid $4 millions and can go up to as much as $7 million, as of the 2022 peak. However, townhouses and condos with similar square footage are relatively less expensive, owing mainly to negligible lot sizes and the many common walls and areas. Over the course of thirteen and a half years since the last late 2008 housing market crash, overall real estate prices have more than tripled.