Hillsborough, CA Homes for Sale with Pool

Step into a piece of history w/ this extraordinary Hillsborough property, originally the 5-stall carriage house for the infamous 16-acre Fagan Estate. Transformed in 1971, the carriage house is now a luxurious single-family residence, designed to cater to modern living, while beautifully preserving the historic charm. Spanning approximately 7,000 square feet, the home includes 7 bedrooms, 4.5

Emily Patterson KW Advisors

STUNNING RENOVATION!!! UNBELIEVABLE LANDSCAPE!!! PRIME LOCATION!!! This masterfully renovated 2004-built estate is set on a premier, tree-lined corner lot in one of Lower Hillsborough's most prestigious & secluded neighborhoods. Main House is 3,786 sf + a pool house with 308 sf, bringing the total to 4,094 sf of remodeled living spaces. Soaring ceilings and expansive resort-style grounds set the

Stanley Lo Green Banker Realty

A stunning bucolic estate within the exclusive Hillsborough hills perches at the end of a long, private cobblestone drive. This well-appointed home offers 4,240 sq ft of living space on 2.24 acres with views from virtually every room. Backyards large entertaining patio includes a pool/spa, BBQ area and lifesize Kung Fu Panda statue. Kitchens picture windows let natural light gleam off long

Gina Haggarty Compass

Casa Del Sol is a magnificent three-story estate of striking stature that embodies the pinnacle of luxury. Lower-central location, walkable to the park and Burlingame's trendy eateries. New 2023 Concrete Podium Construction. Artfully created landscaping providing seclusion and privacy. Step inside and experience the grandeur and grand-scale rooms. Unrivaled quality. Meticulous details.

Margaret Duffy Coldwell Banker Realty

Welcome to 20 Pine Court, where sleek modern design meets the warmth of everyday life. Tucked at the end of a quiet cul de sac in Hillsborough, this 5 bedroom, 5 full bath, 2 half bath home was designed by acclaimed architect Sean Bailey to invite both connection and calm. Picture your mornings here, light pouring through floor to ceiling glass, enjoying breakfast at the oversized kitchen island

Paul Zinchik Compass

Step into your modern farmhouse masterpiece in the coveted Carolands neighborhood of Hillsborough. Situated on a flat and spacious half-acre lot, this home has undergone a complete renovation and expansion, ensuring a modern and comfortable living experience. The main house offers 4 bedrooms and 4 bathrooms, with the added bonus of a brand new ADU that includes a 5th bedroom and additional bath.

Phil Chen Christie's International Real Estate Sereno

A modern sanctuary of luxurious California living, 655 Hayne Road is nestled in Hillsboroughs coveted Lower South neighborhood. Offered pre-completion with an estimated finish date of November, this gated estate sits on a sprawling, fully usable lot and blends sophisticated design with resort-style amenities. The open-concept main residence level embraces indoor-outdoor living and showcases

Shaun Walter Coldwell Banker Realty

BRAND NEW, COMPLETELY REBUILT MID-CENTURY SMART HOME (COMPLETED IN 2025) LOCATED IN PRIME LOWER HILLSBOROUGH, IN THE PRESTIGIOUS RYAN TRACT NEIGHBORHOOD! This split-level home boasts a sleek exterior, new interior with all the latest smart home technology, a lower level attached basement ADU (included in total square footage) with a full kitchen, bedroom, and bathroom. ABSOLUTELY NO EXPENSE WAS

Stanley Lo Green Banker Realty

RARE FIND! Don't miss this once-in-a-lifetime opportunity to live on one of Hillsborough's most prestigious streets. Nestled on a nearly 3/4-acre lot at the end of a peaceful cul-de-sac, this property offers the perfect blend of privacy and convenience. Just a 5-minute drive brings you to the vibrant shops and restaurants of Broadway or downtown Burlingame. Commuters will appreciate the quick

Stanley Lo Green Banker Realty

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

Experience the perfect blend of luxury, elegance & California living in this breathtaking Mediterranean estate. This residence offers unparalleled privacy & sweeping views of the San Francisco Bay & surrounding mountains. A long, gated driveway welcomes you setting the stage for the home's elegant interior. Step inside to a dramatic, light-filled foyer featuring a graceful winding staircase that

Donald Kung Remax Capital

Situated on a commanding half-acre lot, this inviting home offers over 4,400 sq. ft. of casual elegance in a picturesque setting. A dramatic foyer leads to the elegant living room with a grand fireplace, wall of windows, and access to a huge rear deck. The gracious dining room features oversized windows that frame amazing views of the outdoors. Nearby, the large family room with a fireplace,

Jim Arbeed Coldwell Banker Realty

Completely transformed with a sophisticated modern aesthetic, this Hillsborough home showcases sweeping and spectacular Bay and San Francisco skyline views. High end down to the studs remodel in 2013 with no expense spared. Located in the coveted Lakeview neighborhood on just over one-half acre, features a striking two-story facade and generous outdoor spaces designed for entertaining around a

Judy Citron Compass

LOWER HILLSBOROUGH'S PREMIER ESTATE! LUXURY, DESIGN, & PRIVACY! Rare listing, a once-in-a-lifetime property w/ one of the LARGEST LOTS in its area -- 1.286 ACRES OF TOTALLY FLAT LAND! European style Italian Villa, constructed to perfection resembling the work of "turn-of-the-century" architect George Howard. UPDATED & RENOVATED throughout the years. EXTENSIVE STREET SETBACK. Detached 5-car garage

Stanley Lo Green Banker Realty

CASA SERENA: HILLSBOROUGH'S BESPOKE HOMAGE TO SANTA BARBARA LUXE. Casa Serena dazzles with authentic quality and the romance of Riviera retreats, yet delivers its new owner a platform of thoroughly modern livability. The estate you see today was meticulously re-imagined, expanded, and re-built to the highest standards. Spanning 5,600 sq. ft., you are invited to marvel at the "composition within

Geoffrey Nelson Coldwell Banker Realty

Tucked at the end of a quiet cul-de-sac on approximately 2 private acres, The Koshland Estate is a once-in-a-lifetime offering in one of the Peninsulas most prestigious enclaves. Designed in 1961 by Frank Lloyd Wright disciple Howard Friedman for his father-in-law, Levi Strauss & Co. President and CEO Daniel Koshland, the home was constructed to exceptional commercial-grade standards, rarely seen

Pierre & Alex Buljan Compass

PRICE REDUCED, THE BEST DEAL JUST GOT BETTER!!! Nestled in the Hillsborough foothills, this exquisite estate embodies prestige & sophistication in one of Californias most coveted enclaves. Set on a generous lot, it offers exceptional privacy w/ only one neighbor & lush greenery for lots of privacy. Mediterranean-inspired design shines w/ arched doorways, sculpted balusters, & a grand foyer.

Stanley Lo Green Banker Realty

NEW LISTING AND RECENTLY REFRESHED!!! ONE OF HILLSBOROUGH'S FINEST PROPERTIES!!! Breathtaking views of the San Francisco bay & beyond. HUGE MOSTLY LEVEL LOT WITH OVER .5 ACRES. Exquisite Mediterranean designs with a red-tiled roof and circular paver driveway. A grand foyer welcomes you in with soaring ceilings. Throughout, you'll find hardwood flooring, carpeting, and recessed lighting. To the

Stanley Lo Green Banker Realty

Tucked along tree-lined Montero Avenue in Burlingames coveted Easton Addition, this beautifully updated and expanded home blends warmth, design, and function. With over 3,000 sq ft, 4 bedrooms, and 3.5 baths, it offers thoughtfully curated spaces for modern living. The heart of the home was reimagined in 2019 with an open flow between the kitchen, dining, and family rooms, all connected by white

LAURA BRYANT KW Advisors

Welcome to this bright top floor condominium residence offering a unique blend of comfort and charm. One bedroom + den has multiple skylights that bathe the living space in sunshine throughout the day. Adjacent to the living room, the den provides an ideal space for home office, reading nook, or guest area. Kitchen, while compact, is efficiently laid out with ample cabinetry, updated

Louie Kappen Coldwell Banker Realty

Welcome to Top of the Mounds, San Mateo's Premier luxury condominium community. This completely remodeled condominium with fantastic San Francisco Bay views is turn key and ready to move into. There's a large terrace off the living room for relaxing or barbecuing which takes advantage of the great bay views. Gorgeous hardwood floors thru-out the 2,076 square foot living space. The remodeled

Vince Cardinale Compass