Hillsborough, CA Homes for Sale with Pool

A masterful expression of California Farmhouse architecture, 1950 Ralston Avenue is a newly completed estate on a level 0.51-acre lot in Hillsborough's prestigious Country Club Manor. Walking distance to the town's top-tier schools and vibrant Downtown Burlingame, it perfectly blends prestige with ultimate convenience. Combining natural beauty with timeless sophistication, the residence showcases

Gina Haggarty Compass

Sweeping Bay and San Mateo Bridge views define this expansive Hillsborough residence, cherished by the same owners for more than 40 years. Recently refreshed and updated, the home features newly painted interiors, hardwood floors and a dramatic great room with walls of glass overlooking the pool and expansive deckan exceptional setting for everyday living and entertaining. Designed with

Samia Morgan eXp Realty of Northern California, Inc.

*BRAND NEW ADU UNDER CONSTRUCTION, STARTED FEB 2026 W/ FRAMING ALREADY COMPLETED* THIS TROPHY HOME IS A ONE-OF-A-KIND MODERNIZED SMART-HOME MANSION! THE IMPOSSIBLE WAS DONE W/ THESE MULTI-MILLION DOLLAR RENOVATIONS! This magnificent estate perfectly integrates timeless architecture with a modern interior, with all top-of-the-line amenities. An estate fit for royalty! Interior with 100s of

Stanley Lo Green Banker Realty

Set on more than 12 secluded acres, Villa de Verano is an ultra-exclusive Hillsborough estate inspired by the elegance of Lake Como. The gated compound offers exceptional privacy, symmetry and scale, with a tree-lined drive leading to a grand motor court & the main residence, guest quarters & sports pavilion. The 12,404 sqft main residence spans 3 levels serviced by an elevator & overlooks the

Jenn Gilson Golden Gate Sotheby's International Realty

Sitting on a commanding 2.5 acres atop a Hillsborough promontory with panoramic views, this bespoke estate reflects the vision of MAK Studios authority in modern design. Defined by a sculptural stone, glass and wood facade and a dramatic 22-foot high entry that frames the horizon, this home has 8BR's and options for 2 offices. The culinary program is exceptional: a statement kitchen appointed

Phil Chen Christie's International Real Estate Sereno

*NO SHOWINGS UNTIL AUGUST 2026* Set behind private gates on a 0.645-acre parcel in Hillsborough's prestigious neighborhood, this 9,035 sq ft estate offers sweeping San Francisco Bay views & exceptional scale. A grand double-door entry opens to a dramatic foyer with a stained-glass dome skylight, leading to an expansive main level defined by floor-to-ceiling glass and abundant natural light.

Stanley Lo Green Banker Realty

SELLER ALREADY PURCHASED AND WOULD LIKE TO REVIEW ALL OFFERS! *MILLION DOLLAR REDUCTION!!!* HILLSBOROUGH'S BEST IN CLASS, THIS IS LUXURY! MUST SEE!!! A BREATHTAKING TROPHY ESTATE BLENDING TIMELESS ELEGANCE WITH RESORT-STYLE LIVING. This architectural masterpiece offers an extraordinary layout designed for both grand entertaining & intimate daily life. Sweeping driveway & motor court lead to 2

Stanley Lo Green Banker Realty

Secluded in the exclusive Country Club Manor neighborhood of Hillsborough, this fully furnished modernist masterpiece, a three story wonder of glass that floats with the forest. Designed by acclaimed, award-winning architect Leonard Ng, this iconic 11,141 sq. ft. retreat is a meditation on minimalism, an extension from the trees that questions where nature ends & home begins. Clear heart cedar

Gina Haggarty Compass

Built in 2011, this exceptional gated residence blends timeless architecture with modern luxury just minutes from Downtown Burlingame and close to acclaimed Hillsborough North Elementary and Crocker Middle School. Designer finishes throughout include Calacatta marble countertops, custom honed limestone fireplaces, hand-painted strié wall finishes, polished nickel Rohl fixtures, oil-rubbed bronze

Max Lo Green Banker Realty

Sprawling Privacy Meets Elegant Living Hillsborough Welcome to your private estate, a secluded sanctuary tailored for multi-generational family living & spectacular entertaining. Tucked behind a gated driveway on a premier 2-acre lot, this single-family residence offers a blend of luxury, space, & serenity in one of Hillsboroughs most coveted enclaves. Built in 1974, the home spans a generous

Gina Haggarty Compass

Gracefully tucked behind private gates in Lower Hillsborough's premier location, this exceptional contemporary residence offers a rare blend of privacy, sophistication, and effortless indoor-outdoor living. Directly across from the lush fairways of Burlingame Country Club, the home enjoys expansive green views, a majestic redwood grove, and a serene connection to nature. Designed for both relaxed

Phil Chen Christie's International Real Estate Sereno

Situated on a private side street, this grand estate sits on a majestic 2-acres with jaw-dropping panoramic bay views, some of the best in all of Hillsborough. Exquisite architectural detailing and finishes throughout, including inlaid parquet walnut floors, hand carved fireplaces, and walls of glass framing iconic bay views and landscaping. The main level includes a stunning office, billiard

Pierre & Alex Buljan Compass

Discover the Top of the Mounds, San Mateo's most coveted luxury condominium community. This gorgeous residence offers 2036 sq ft of spacious living with sweeping panoramic Bay and Peninsula views from nearly every room. The generous 2 BR/2BA floor plan features lovely carpet and tile, a beautiful chef's kitchen with ample cabinets and granite countertops, plus spa-like bathrooms. Enjoy the

Janet Russell David Lyng Real Estate