Hillsborough Oaks Etc. Real Estate

Welcome to Hillsborough Oaks, a serene and picturesque neighborhood nestled in the heart of Hillsborough, California. Known for its lush landscapes and stunning estates, this exclusive community offers an unparalleled quality of life that attracts families and professionals alike.

Hillsborough Oaks boasts tree-lined streets and expansive lots, creating a tranquil atmosphere that feels miles away from the hustle and bustle of city life, yet is conveniently located just minutes from downtown San Mateo and the vibrant Bay Area. The neighborhood is characterized by its elegant homes, each uniquely designed, reflecting the architectural charm that Hillsborough is renowned for.

Residents here enjoy a strong sense of community, with friendly neighbors and a commitment to maintaining the beauty and integrity of the area. Hillsborough Oaks is served by top-rated public and private schools, making it an ideal choice for families looking for an exceptional educational environment. The nearby parks and recreational facilities provide ample opportunities for outdoor activities, from leisurely strolls to more adventurous pursuits.

For those who appreciate the finer things in life, Hillsborough Oaks is in close proximity to upscale shopping, gourmet dining, and cultural attractions. The neighborhood’s convenient access to major highways and public transportation makes commuting a breeze, allowing residents to enjoy the best of both suburban tranquility and urban convenience.

In Hillsborough Oaks, you’ll find not just a home, but a lifestyle defined by elegance, community, and natural beauty. Come discover the charm of this remarkable neighborhood and experience the warmth of Hillsborough living.

Newest Listings in Hillsborough Oaks Etc.

$28,995,000

11 Beds ⋅ 15 Baths ⋅ ML82038870 MLS

A secluded trophy estate in the heart of highly coveted Lower North Hillsborough, this extraordinary 2.4+ acre property offers rare scale and privacy on one of the towns largest parcels. Originally designed by acclaimed architects John Bakewell Jr. and Ernest Weihe, the French Chateau-inspired residence was once home to Hollywood icon Bing Crosby and is rich with storied provenance, including connections to the legendary Seabiscuit and curated antique details from the Hearst Collection. Thoughtfully updated by the current owner, the home spans four levels and features 11 bedrooms, 10 full baths, and 5 half baths, blending grand architectural presence with a warm, livable layout. Designed for both intimate daily living and elegant entertaining, the floor plan includes multiple salons, a formal dining room, a wood-paneled library, a private office, and a distinct guest wing. The park-like grounds showcase sweeping lawns, a resort-style pool with fountains, and expansive open space, creating a serene and majestic setting. With its remarkable history, refined craftsmanship, and exceptional acreage, this is a truly irreplaceable legacy estate an unparalleled opportunity to own a landmark property from California's Golden Era.

1200 Armsby DR, Hillsborough

Listed by Jenn Gilson, 650-642-6957 from Golden Gate Sotheby's International Realty
(If provided) CoList: Pierre & Alex Buljan from Compass

$14,000,000

ML82050246 MLS

25 Fagan DR, Hillsborough

Listed by Pierre & Alex Buljan, 650-400-1188 from Compass
(If provided) CoList: from

$8,990,000

ML82034335 MLS

A RARE ONCE-IN-A-LIFETIME LOT RARELY SEEN IN THIS NEIGHBORHOOD! BUILD YOUR DREAM HOME! PRIME LOWER HILLSBOROUGH LOCATION WITH .90 ACRES OF MOSTLY USABLE LAND! NEWLY RENOVATED POWERFUL WATER WELL!!!! SAVE ON YOUR WATER BILLS WHEN WATERING YOUR GARDENS! YOU WILL NOT FIND A BETTER CHOICE THAN THIS CURRENTLY IN HILLSBOROUGH, AND THINGS THIS GOOD ONLY POP UP ONCE IN A BLUE MOON!!! Located at the end of an exclusive cul-de-sac in the prestigious historic Fagan Estates subdivision. This lot features A WIDE SPRAWLING GREEN LAWN with almost an acre of pristine land! Encompassed by an abundance of mature trees offering total privacy. Only .5 miles walking distance to bustling Downtown Burlingame. The lot offers the perfect canvas to get everything you've dreamed about with only your imagination being the limit. ONCE-IN-A-LIFETIME OPPORTUNITY, RARE LISTING, AND MORE! (Images of houses are digitally altered renderings used solely to illustrate potential use of the space. No plans have been prepared, submitted, or approved by the City of Hillsborough, and no consultants or experts have been engaged to evaluate feasibility. There is no house on the lot)

90 Fagan DR, Hillsborough

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: from

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The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than RE/MAX CAPITAL are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.