Hillsborough CA Real Estate & Homes for Sale

Classic California Ranch Home with incredible bay views offers an ideal family retreat in a resort like setting. This beautiful estate is set upon nearly one full acre and commands unobstructed south-facing bay views. Amenities include 4 bedrooms and 3 full bathrooms on the main level, newly updated chef's kitchen with quartz counters, and formal dining and living room with wood-burning fireplace. Downstairs features a large family room with fireplace opening to an expansive rear deck, plus 5th bedroom and adjacent office/gym with full bath and separate entrance. Enjoy the backyard's private sanctuary which boasts a large grassy play space with play structure, an enormous deck for outdoor entertaining and rolling oak-studded grounds. Privacy and serene living at its best, all in walking distance to Vista Park and South School! *Note: tax records only show 4 bedrooms; buyers to verify permits and square footage.

5,680 SQUARE FEET of ultra-luxurious living space, completely rebuilt for current owners. Set atop a gentle .6 acre knoll in one of Hillsboroughs choicest locations, there is absolute privacy and serenity, with all main rooms opening onto garden terraces, spectacular vistas, and receiving natural light all day long. Within, are 4 en-suite bedrooms, including 2 master suites with reading/media retreats, large formal living and dining rooms, chefs kitchen and adjoining family and breakfast rooms, plus a sunlit gallery, office, den. Outdoors are childrens play areas, sweeping lawns and stone patios. Additional features include a new raised seam metal roof, state of the art electronics with Wifi, Sonas sound, full home security, plus energy efficient climate control with 3 separate heating and air conditioning Systems. Exquisite architectural features include numerous French doors, high ceilings, wainscotting and crown moldings, and white oak plank hardwood floors.

Breathtaking Bay views from S.F. to the S.M. Bridge to the East Bay hills & beyond. This glorious +/-3-acre custom estate was built by the original developer of the Tobin Clark Estate area as his personal residence and exudes elegant grandeur with a warm & welcoming atmosphere in an ideal floor plan. Tremendous room sizes & ceiling heights are evident throughout the +/-7,000s.f. of living space. The foyer with dramatic curved staircase introduces the living room with floor-to-ceiling windows that frame the remarkable views. An extra-wide hallway leads to the office, family room with step-down bar, kitchen with breakfast room, & secondary bedroom suites. The upstairs primary suite offers a fireplace, 2 full baths, 2 walk-in closets & a view-facing balcony. Amenities include a gated driveway with porte-cochere, 3-car garage, waterfall, huge windows, 4 fireplaces, multiple covered patios & an amazing rear yard with lush lawns, pool & full-size tennis court overlooking the incredible views

Outstanding opportunity to remodel this vintage 1970s traditional gem in upper Hillsborough. On the market for the first time with time-honored floor and wall coverings, light fixtures, and finishes throughout. One-level floor plan with lower 3-car garage, laundry, and bonus room for potential bedroom and bath. Every room is sizable, including living room with fireplace and paneled cathedral ceiling, formal dining room, and fully open kitchen and family room combination. 4 bedrooms and 2.5 baths include a primary suite that opens to the rear yard. Level rear yard and spacious patio. Enjoy today, renovate, or possibly build new - the choice is yours.

This French-inspired home truly has it all: 5 bedrooms, 4.5 bathrooms, separate office, spectacular views, loads of natural light, high ceilings and several flat grass areas for play. The oversized living room features French doors to the deck, custom crown molding,�walls of windows and a fireplace. The formal dining room is perfect for entertaining with a picture window and views. The large chef's kitchen opens onto the great room and out onto the Wisteria covered patio and flat grass area. Down the arched hallway is the primary bedroom retreat featuring a sitting area, French doors, en-suite bathroom, walk-in closet and separate office. Two additional large bedrooms feature ensuite bathrooms. The final two bedrooms share a Jack-and-Jill bathroom. The redwood deck stretches the length of the home offering views from sunrise to sunset. Located on a small cul-de-sac with just 3 other homes and a 3 car garage, this home really does have it all.

In Lower North Hillsborough, this modern French Chateau-style residence was extensively updated in 2015. The two-level home with elevator accommodates work from home and distance learning needs as well as for fitness, recreation and outdoor enjoyment with a large lawn for play, pool, spa, outdoor kitchen and dining deck. A dramatic two-story entry reveals espresso-colored oak floors, refined millwork, exquisite finishes, detailed tray ceilings and glass doors at every turn for seamless transitions to outdoor living spaces. Formal living and dining areas are complemented by casual spaces, including a chefs kitchen with professional grade appliances, family room, media room and library, all with easy outdoor access. Three of the 6 bedrooms are suites; two have luxe bathrooms, walk-in closets, and a fireplace or balcony. Located minutes from downtown Burlingame and San Mateo, top-rated Hillsborough schools and quick connections to international airports, San Francisco and Silicon Valley.

Spectacular Property nestled on a tranquil knoll, one of the most beautiful settings in Hillsborough. A sense of tranquility surrounds this extraordinary home that's on the market for the first time in over 60+ years. Built in 1924, showcasing supreme elegance and charm this architectural jewel is truly a treasure. Living Room, Formal Dining Room, Vista Galleria, Vintage Kitchen with Breakfast Room, Spacious Master Suite and 4 additional bedrooms all enjoy attached bathrooms. Enjoy relaxation and entertainment lifestyle on this secluded .75acre lot with circular driveway surrounded by lawn, gardens, patios, mature foliage, tennis court and towering trees with close proximity to commute routes to SFO, Silicon Valley and exceptional schools! If you are looking for a property with a touch of individuality and an abundance of potential --- this home is for you! Rare Find! Don't Miss!

Nestled on a hillside corner lot with spectacular views from every room, this contemporary masterpiece is just a mile from downtown San Mateo but worlds apart from everyday life. A gated, designer driveway reveals this amazing floor plan with 4beds+office, 5.5 baths, motorcourt and 3-car garage, decadent pool and spa, and multiple patios capturing West Coast Oak forest views from the .72 acre estate. The entry lounge with wet bar opens to a bamboo study and bath. Entertainers dream kitchen boasts 2 dishwashers, butlers pantry, newer high-end appliances, private patio, generous dining and open-concept living areas. Lower bedroom suite opens to living area, bar and the fabulous pool and spa. Custom upgrades include 3-level elevator, solar radiant heating/water, security system, designer finishes, Pella windows, heated master bath floors and towel rack, and low-water landscaping in gated exterior. Call for a tour!

Situated behind private gates on a lush 1.48-acre lot in lower North Hillsborough, this exceptional estate offers elegant architectural detail and an ideal floor plan spanning over 9,300s.f. The grand foyer with gorgeous stone floors opens to the lovely formal rooms and showcases two sweeping staircases, one that leads to the upstairs private quarters, and one leading to the downstairs recreational part of the home. A gourmet eat-in kitchen with large center island & walk-in pantry opens to the family room, while a 2nd family room is located on the lower level. Amenities include two dedicated offices, a gym, sauna, two laundry rooms, children's playroom with chalkboard wall, billiard room, wet bar with ice maker, dishwasher & refrigerator, and a 1,000-bottle wine cellar. Tranquil Grounds with verdant landscaping, majestic trees, sprawling level lawn, fire pit, play structure, bocce ball court, multiple balconies & entertaining patios are a few of the highlights of this outstanding home

Absolutely stunning at the end of the lane with sweeping canyon views. Magnificently reimagined in 2013 with designer quality at every turn, plaster-finish walls, & hardwood floors. Stunning formal living & dining rooms, each with elaborate ceilings & dazzling lighting. Showstopper kitchen with island seating & high-end appliances. Main-level primary suite, office/5th bedroom, plus second suite; 2 bedrooms and bath with steam shower on lower level. Large recreation/family room opens to a heated loggia with adjoining customized wine cave for hundreds of bottles plus case storage. Resort grounds with infinity edge solar pool, spa, 2 barbecue kitchens, fireplace, fire pit & synthetic lawn for amazing outdoor entertaining space. Solar electricity, Sonos sound inside and out & Tesla charger. Great Hillsborough schools. And walking distance to Vista Park!

Mostly usable land! A rare find in a highly sought-after Hillsborough location. Situated on a 0.628 acre (27,360 SqFt*) corner lot. Located just minutes from Downtown Burlingame and highly rated schools. This private and secluded home features sprawling lawns, a pristine sparkling pool & spa, and high vaulted ceilings. Close to superior schools & Downtown Burlingame.

30 Searsville is a new modern estate organically constructed into the hillside and situated on 3.95 acres of nature with spectacular canyon views. This custom home combines understated elegance with 16ft ceilings to provide spacious comfort in the heart of the house, which includes the grand foyer, living, dining, and kitchen combo that floats seamlessly out to the multiple decks and views of the vistas. The 5BR 5.5BA home is spread out for adaptability and multigenerational families with enough space for a workout area, extra office or game room. The home includes high end Miele appliances and custom Pedini cabinetry throughout. This unique house takes advantage of its natural topography with private trails and potential pool and lawn sites. It allows for the perfect combination of space and seclusion with accessibility to San Mateo County's best schools, restaurants and transportation.

NEW EXTERIOR VIDEO & PHOTOS ADDED. Situated on a gated corner lot with nearly an acre of flat park-like land located in the Hillsborough Heights neighborhood of lower Hillsborough, this English Country Manor style home has been beautifully updated and remodeled including a newly added mudroom and sports court. A large terrace, a new sports court, and a gated auto court with plenty of parking for guests. This property has approved plans for a 499 SqFt clubhouse that will be situated between the back terrace and the sports court. The Town of Hillsborough has confirmed that a guest house (ADU) with a max size of 1,400 SqFt with a detached garage would also be allowed (Site Plan available). Just around a mile walk to Downtown San Mateo, about a 5-minute drive to Downtown Burlingame, close to many amenities, and access to highly rated schools, make this property a very desirable place to call home.

Classic Mediterranean villa in a quiet cul-de-sac. Entrance level has grandeur arch ceiling living room with meticulously built dome shape brick fireplace, large formal dining room for a big gathering, kitchen, breakfast nook, powder room, pivot swirl doors to 3 balcony and expansive deck overlooking hills, valley, bay and heated pool. Built 1979, living area 4,430 sq. ft. on top and mid level, plus 560 sq. ft. finished basement has an exquisite brick wine cellar, heated pool, a full bathroom with double shower heads, a kitchenette, a family room opens up to exterior sitting area for ultimate entertaining. Newer tile roof. Steam room in master bathroom shower. Separate furnaces and water heaters for master suite and the main house.

Majestically situated on a quiet cul-de-sac behind private gates and a long sweeping driveway, this outstanding architectural tour de force boasts exceptional style with breathtaking San Francisco and Bay views in nearly 12,000s.f. of luxurious living space. With massive walls of windows showcasing the vast, sweeping views from almost every room, the sun-drenched interior unfolds with a dramatic marble foyer that showcases the awe-inspiring views while overlooking the chic public rooms. An open floor plan with glass railings, incredible ceiling heights and grand-scale rooms characterize the grandeur of this magnificent home. The primary suite is truly stunning, both in size and design, and offers a dressing room with a 2-story closet and access to a huge, slate sun deck overlooking the Bay views. A dedicated office, gym, library, piano alcove, conversation pit with bar, and 4-car garage with custom cabinets are just a few of the amenities offered by this once-in-a-lifetime opportunity.

HILLSBOROUGH ARCHITECTURAL OPUS...ITALIAN FARMHOUSE SUPREME AT RARE LUXURY ENCLAVE. From the Stonebridge cul-de-sac of just 14 epic estates, Modern Luxury meets Old World lyricism. A statement of architectural perfection. Designed by acclaimed Hillsborough architect John Stewart and custom built in 2010 to the highest standards. Like-new luxury, spanning 6,790 sq. ft. of living across three distinct levels with 6 beds, 6.5 baths, plus CEO's Office. Signature details cascade with reclaimed roof tiles, arcades and verandas, all enhancing enormous rooms, views above the Bay, and a Mediterranean garden dynamic. Lower level functions as its own ADU apartment, with kitchen, living room, bedroom, and patio, or use it as your connoisseur's "cave" for billiard room and wine cellar. 3-car garage, Central AC, built-in outdoor BBQ, flat lawn for future pool site, plus terraced patios and gardens.

***JUST IN - An 800+/- SF ADU is in the process of building (target completion in 3 months) *** A rare opportunity to own a one-of-a-kind compound that has been "gutted to the studs" and meticulously rebuilt from the ground up and crafted to provide a quality of living impossible to recreate. Situated in a large corner gated lot on one of the best streets in Hillsborough walking distance to schools and Downtown Burlingame. Unique cedar fencing, a new deluxe elevator from garage to main level, smart home, every hardware & fixture is innovative & deluxe | 2 DaVinci Fireplaces with backlit translucent stone wall cladding | state of the art kitchen with top-of-the-line sinless-steel appliances | accordion-style fully opening patio doors, and much more. The approx. 5,700+/- SF total floor area includes 4,000+/- SF of living space, 900+/- SF garage area, and 800 +/-SF ADU. A potential 1,100+/- SF can be added to the 2nd floor for more bedrooms, subject to town of Hillsborough's approval.

Hillsborough NEW CONSTRUCTION | Living Space: 5,109 sqft and Lot Size: 21,000 sqft | Stunning attention to detail | Landscaping and a grand entryway invites you into the large entertainment room and open interior | Enjoy indoor-outdoor living w/La Cantina sliders | The living and dining rooms are centered around a feature fireplace | European white oak hardwood floors | Kitchen has Miele and Liebherr appliances, sweeping countertops, and high-end fixtures | Office w/built-in cabinetry and views over the front yard | Five bedrooms featuring master walk-in closets, five full baths, and two half baths throughout | Distributed audio system | LED lighting | Network system | Three-zone heating/cooling | Jeld-Wen windows | Two-car garage w/guest parking | Storage | EV charging plug | Outdoor BBQ Area | Outdoor Fire Pit Area| Come indulge in this one-of-a-kind residence while its still available!

FOR THE MOST DISCERNING OWNER, THIS LUXURIOUS ESTATE, REMODELED IN 1996 BY A PRINCIPAL ARCHITECT OF FRANK LLOYD WRIGHT'S COMPANY OFFERS CONTEMPORARY LIVING WITH 6 BEDROOM SUITES AND 7 BATHS PLUS 2 HALF BATHS, A LARGE KITCHEN THAT ANY GOURMAND WOULD APPROVE OF! OTHER APPEALING AMENITIES INCLUDE A HUGE LIVING ROOM AND DINING ROOM, GAME ROOM, MEDIA ROOM, WINE CELLAR, AND THE HOME FEATURES A UNIQUE INDOOR POOL. LOCATED IN THE CAROLANDS AREA, THIS ESTATE HAS IT ALL!

Truly a must-see home! 25 Bridle Way is an amazing example of the Tudor Style that architect David Adler prided his work on. This sprawling home that is steeped in history, includes 7 bedrooms and 6 1/2 bathrooms. The homes Incredible formal living room would be appropriate for Gala Events and is reminiscent of great rooms in large-scale mansions in the English Country. The home originally served as one of three carriage houses to Celia Tobin Clark's "House on Hill". A noted horse person, she insisted that the stables and carriage house be completed first, prior to the beginning of the construction of the hand built historic, House on the Hill. It is being offered for sale for the first time in multiple decades and has been in the same family for 40+ years. This is an amazing opportunity to call a piece of history home.

Located on a private cul de sac sits this contemporary Cape Cod style home located on a resort-like .89 acres. A grand marble foyer leads to a formal living room and large executive office all with 11+ft high ceilings. Above a few steps sits a spacious formal dining room, a large kitchen fully equipped with ample counter space and double fridges. Off the kitchen is a large family room and entertainment bar that opens to your private outdoor oasis equipped with a basketball hoop, pool/spa and regulation sized tennis court. This home boasts an endless list of amenities that includes multiple private balconies, bay views, a 3 car garage, sauna/steam, 2nd family room upstairs, attached in-law with full kitchen, updated security and lighting. Located a short proximity to world class public and private schools, transportation and shops, you wont find a more complete home.

This elegant Georgian style home offers an impressive pedigree. The grace of this home has been enjoyed by some of the most influential families past, present, and now future. This magnificent residence offers flexibility for 8 bedrooms and 6.5 baths in the main house with Aupair quarters and a full bath. The home features fine details and craftsmanship, plus a light-filled floor plan. The home is the definition of comfort and elegance. The grounds provide an additional dimension with an enormous patio that has two large white pergolas that run the width of the home. From here you are surrounded by gorgeous gardens, groves of redwoods, and a sparkling pool and level lawn. The grounds offer room for a tennis court or guest house. The possibilities are endless. Tucked behind private gates, this impressive estate offers you a rare retreat, just minutes from the amenities the Peninsula has to offer.

If you are looking for the best of the best, this is a once-in-a-lifetime opportunity for you to enjoy your life! After years of renovations, 1868 Floribunda Avenue is ready for you to view! The lot is almost 5x bigger than standard lots, all usable! Renovated to the highest quality, situated in one of the best locations in Hillsborough! Nearly 20,000 square feet throughout 6 buildings. New custom-built water well. Three private gates - resident driveway, guest driveway, and pedestrian walkway. No expense was spared for this property to reach the ultimate heights in a smart & secure dream home! You have to see it, to believe it! Qualified buyers only; qualifications requested in order to be screened before showings.

This charming 5,800 sq ft main home sits on a private and picturesque 1.75 acre lot with breathtaking views. A grand foyer introduces two levels of living offering a flexible floor plan that is perfect for today's needs. The home features 6 bedrooms and 6 plus baths including 2 master suites, family room, office, wine room and 3 car garage. Exterior amenities include a pool house with adjoining bath, pool and spa, putting green, treehouse, and a vineyard grafted from the Sonoma Valley. Saunter through the sequestered gardens of this stunning estate as you sip your own Pinot Noir.

A Stunning Example of Architectural Perfection | This Newly Rebuilt Home is Sure to Take Your Breath Away | Unobstructed Bay and Canyon Views | Main House 6 BD and 5.5 BA | Studio Guest House | Miele Appliances | Waterfall Marble Kitchen Island | 378 Bottle Temperature Controlled Wine Display | Grand Entry | High Ceilings | Open Floor Plan | Italian Poliform Cabinetry | European White Oak Hardwood Floors | Exquisite Marble and Stone Throughout | Distributed Audio System | Prewired Surveillance System | Network System for Entire House | 3 Car Garage | EV Charging Plug | 4 Zoned Heating and Cooling System | LED Lighting Throughout | Office with Builtins | Movie Room with Surround Sound System | Western Windows | La Cantina Sliders | Luxurious Indoor/Outdoor Living | 2,000+ SF of Decking | Large Backyard with Grass | Room for a Pool | Views from Every Window | Treat Yourself to an Elevated Lifestyle Most Can Only Dream Of | This Home Has Everything For The Most Discerning Buyers