By Geoffrey Nelson (unabridged from Gentry Magazine October 2011)

Carolands, Skyfarm, Tobin Clark: the very names evoke Hillsborough’s legendary early estates. Once the land holdings and palatial domains of 19^th and early 20^th century Hillsborough, these areas today represent sought-after subdivisions with a diversity of topography, vistas, architecture, and commute ease. Breathtaking views above San Francisco Bay are a defining hallmark of Upper Hillsborough. Hillsborough’s most dramatic multi-county views are showcased from the elevations of neighborhoods such as Carolands, Skyfarm, and Tobin Clark. Often in unobstructed glory, Upper Hillsborough plateaus showcase vistas above the waters of the Bay, twinkling city lights, the San Francisco skyline, multiple bridges, Mt. Diablo, and beyond. Another distinguishing aspect of Upper Hillsborough locations is the sheer commute ease connecting directly onto Highway 280. Preceded by the recently restored Carolands gatehouse, Chateau Drive is a reliable artery linking 280 to the west, and downtown Burlingame to the East.  Travel times into San Francisco and Palo Alto are minimized via this 280 proximity. Upper Hillsborough neighborhoods such as Carolands, Skyfarm, and Woodgate Hills (along Summit Drive), embody this rare balance of “alpine scenic retreat” feeling with easy navigability and commute optimization. Prestige and real estate desirability are also in evidence, as the #1 MLS sales of year 2009 and 2011 were both in the Carolands area, each selling at over $10,000,000. This corridor also claims the rarity of many consecutive 2-acre parcels.

Centrally located West Elementary School on Carolands’ Barbara Way provides a sense of community synergy. This public school is consistently ranked at the very height of all Bay Area schools for both API results and parental support. At the time of this writing the Academic Performance Index was an impressive 987. Acclaimed Crocker Middle is easily accessed at the base of Chateau Drive. Nearby private schools include The Nueva School at the summit of Skyfarm, and Crystal Springs Uplands (6-12) in the Lower South neighborhood.

Historic presence, although typically more associated with Lower Hillsborough, is the backbone of Upper Hillsborough lore. The Carolands neighborhood is home to one of the most magnificent private residences ever built in the United States: the circa-1914 Carolands mansion (west facade pictured below), National Register of Historic Places # 75000478.  Originally conceived by Harriett Pullman Carolan, Pullman railcar heiress, this French Mansard Chateau of elite standards spans approx. 65,000 sq. ft.  It remains a private residence, now masterfully restored and complete with its own coffee table book and film documentary “Three Women and a Chateau.” Also of historic and architectural significance is the Tobin Clark Estate, first known as “House on Hill.” Wonderfully preserved and renovated in all its elegance, this circa-1931 mansion is a genuine handcrafted Cotswold Tudor by famed architect David Adler. “Skyfarm,” originally attributed to William H. Crocker circa 1890s, is now part of The Nueva School atop Skyline Boulevard. Lesser known, but intriguing in its own right, the Crocker Lake Open Space is tucked below streets such as Jacaranda and Skyfarm. Man-made Crocker Lake was first created to provide irrigation to William H. Crocker’s New Place estate gardens. It is now a hidden greenbelt ecosystem owned and protected by the Town of Hillsborough.

As with all Hillsborough neighborhoods, pleasant micro-distinctions emerge along every unique twist and turn of the rustic streetscape. The new Website HillsboroughBlog.com presents a wealth of this nuanced information, organized into the 10 areas of town. From the most lavish view terrace, to the most quaint garden gazebo, Upper Hillsborough endures as a treasured lifestyle across the generations.