Exclusive homes for sale in Hillsborough

LEGACY LANDS: WORLD CLASS POTENTIAL ON 1.07 ACRE, ALL USABLE!!! Ensconced amidst Hillsborough's finest mansions, this is a rare offering of epic possibilities. Not something you find every day, maybe only once in a decade! 500 Laurent is now proudly presented to the market commanding 46,783 sq. ft. of 100% usable lands in preferred Carolands. At the corner of Ralston, shouldering multi-acre estates, drenched in sun, and ready to develop an unlimited dream lifestyle. Existing circa-1948 home flows on one level around a private courtyard pool & Guest Unit. Beyond the pool, an unbelievable surprise awaits: raw untouched land extending all the way back, ready for new build, tennis court, or huge ADU. While you cultivate your plans, move in, or rent it out. Contemplate the chance of horizon views toward the Bay from your new conception. Sign up for West Elementary, Crocker Middle, or Burlingame High. Manifest your inspiration for a future remodel or new construction at these Legacy Lands.

Introducing an unparalleled residence situated exclusively on Greenbriar Way, within the coveted Lower Hillsborough area and a mere 15-minute stroll from the heart of San Mateo Downtown and adjacent to the highly ranked private school Crystal Springs Uplands School. Immerse yourself among the high-end Spanish tiles by Porcelanosa Adorn, meticulously crafted into the fireplace, bathrooms, kitchen countertops, and floors. Enjoy exceptional insulation courtesy of double pane windows, ensuring a tranquil and energy-efficient haven and high ceilings create an open and airy ambiance. Discover the future of smart living with the Google Smart Home System, seamlessly integrated with Nest devices like the Doorbell, Thermostat, Fire Alarms, and Yale Lock. Your security is paramount, underlined by an eight-camera HD security system with Honeywell Console Control, granting peace of mind. Effortlessly manage your environment through Lutron Wireless Smart Lighting Control, accessible remotely through user-friendly apps. Culinary enthusiasts will relish the pinnacle of kitchen appliances, featuring top-tier Miele offerings. Luxuriate in the bathrooms adorned with TOTO Washlet Toilets, boasting push-button flush and indulgent warm Bidet Seats.

2016-built contemporary masterpiece on a premier street in lower North Hillsborough. Sustainable design by architect Dan Phipps, built by Toboni Builders with solar power, radiant-heated concrete or oak floors, wiring for EV, and radiant deck heated salt water pool on just over one-half acre. Native landscaping, Corten steel walls, and Ipe wood exterior. Accent walls, cabinetry, and doors all in gorgeous walnut and ceilings up to 20 feet. Formal dining room plus tremendous great room with modern kitchen designed for home chef, private chef, and caterers. Primary suite, secondary suite, and office on main level + 2 beds and bath upstairs along with customized study center. Lower level rec room, bath & temp-controlled custom wine cellar. Outdoor oasis includes pool house with bath (potential ADU), BBQ kitchen, fireplace terrace, level lawn, pool & spa + vegetable garden & fruit trees. Excellent Hillsborough public and private schools.

Iconic Western White House. Replica of the Washington DC residence designed by famed architect Julia Morgan. Approximately 3 acres of lush land in Lower Hillsborough. Rebuilt in 1930 and completely refreshed throughout with new fixtures and appliances. Approximately 24,350 square feet of total living space on 4 luxurious levels with 11 bedrooms, 9 full bathrooms and 5 half-baths. Abundant sunlight and soaring ceilings throughout. Formal entry parlor, spacious East Room with fireplace, formal dining room, gourmet kitchen, butlers pantry, breakfast room, family room, Oval Office, recreation room and home cinema theater. Master bedroom suite with 2 bathrooms and 2 dressing rooms, 6 additional bedroom suites, 4 family bedrooms and 5 powder rooms. Lower-level staff quarters include a fitness room, wine cellar, living room, and laundry center. Stunning grounds with rose garden, exquisite trees, swimming pool and pavilion. Easy access to shopping, dining, golf clubs and commute routes.

Stylish home in lower South Hillsborough. Gracious entry with high ceilings and elegant staircase, grand living room with large arched window opening onto a delightful courtyard that leads out to a level lawn area. The central floor plan includes a formal dining room and charming light-filled breakfast room off the updated kitchen. The updated kitchen includes a Viking cooktop, Thermador double ovens, Subzero refrigerator and built in desk. A large family room opens out to the backyard patio area. The private upstairs features a spacious primary suite with enchanting balcony, dual walk in closets and remodeled bath The updated hall bathroom serves the 2 spacious and bright bedrooms. The functional 4th bedroom on the main floor with built in desk, cabinetry and murphy bed. The adjacent remodeled full bath is conveniently located to be used as a powder room. Beautifully landscaped gardens surround the property adding to the appeal of this exceptional home full of architectural details.

elcome home to 837 Chiltern Road. An Entertainers paradise with captivating views, oversized rooms and finishes befitting a custom hillside paradise in Hillsborough. Nestled on an approximate half acre hillside lot, this custom abode has low maintenance landscaping and several patio spaces for entertaining and gazing. Main level features gorgeous and timeless hardwood flooring, a formal living room with soaring tray ceiling, formal dining room with views, large kitchen with Island, and one of the multiple primary bedrooms. Upper level features an oversized primary bedroom with a private balcony and amazing views. The suite features a separate sitting room, two walk-in closets and two full bathrooms. Two additional oversized Jack and Jill bedrooms also share 2 full bathrooms. The lower level features 2 garages, a possible 3rd primary bedroom or 2nd family room as well as 2 wine storage areas.

This home is located in a quiet cul-de-sac surrounded by pretty canyon views. It has great scale and offers 5 bedrooms, 4.5 bathrooms. Main level consists of elegant public rooms, eat in kitchen with family room, 1 bedroom plus a large primary suite with office/closet. Lower level offers another spacious primary suite, bedroom, bathroom and an additional bedroom/game room with wet bar and fireplace. Kitchen and family room have direct access to outdoor deck, garden and swimming pool. This special home has great bones. 1st time on the market in decades. Fantastic value and potential!

This 1920's Spanish single-level home is truly magical and unique in Hillsborough! Tucked away on a mostly flat and landscaped 1.3 acre lot in the sought-after Hillsborough Oaks neighborhood, the house features an arched entry, wood-beamed ceilings and stylish character. Highlights include a living room with cathedral ceilings, custom fireplace and windows on three sides. The great room combines an updated kitchen, walk-in pantry and family room with access to the private and spectacular deck. In the bedroom wing of the home, the primary bedroom has 3 walls of windows, ensuite bathroom and walk-in closet. Take a step outside to the true oasis of a backyard including a large pool, sprawling lawns (with a well to help with the lush landscaping), patios, decks and mature landscaping. All this, and Hillsborough's famed public schools and minutes to 280 and 101.

GREAT OPPORTUNITY FOR THIS TROPHY ESTATE***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.

Welcome to this truly extraordinary modern hilltop mansion where you will feel like you are living in the sky. Brand new state-of-the-art construction perched high on top of 2.19 acres with unobstructed views as far as the eye can see, there's nothing like it in all of Northern California today. 26-ft high curved ceilings & rounded walls with floor-to-ceiling windows showcase 180-degree bay & canyon views giving residents a light airy feel of relaxation while showcasing the home's grandeur. A gorgeous limestone terrace where the horizon is on full display hosts a curved pool with dancing water feature, spa, built-in Kalamazoo bbq station, outdoor shower, & access to a fully separate, equally luxurious 2-bedroom, 2 bath guest house. Features of the main residence include: 4 bedrooms with en suite baths & jacuzzi tubs, Office, theater, game room, gym, steam room, sauna, elevator, Crestron home automation, gated entry, fingerprint access, 360 bottle wine cellar, 5 fireplaces, multiple balconies, Leicht cabinetry, Gaggenau appliances, Sub Zero refrigerators, Cambria countertops & showers, Thassos Premium Marble & European Oak floors, solar panels, 2 EV charging stations, central vacuum, Italian imported doors, windows, closets & garage door, copper roof, 4-car garage & much more!

SITUATED ON A 1.1 ACRE FLAT PARCEL, THIS 7600+/- SF HOME IS LOCATED ON ONE OF HILLSBOROUGH'S MOST COVETED STREETS. EVERYWHERE YOU LOOK, THE DESIGN CELEBRATES IMPRESSIVE ARCHITECTURAL INTEGRITY, WHILE ESTABLISHING AN INDOOR/OUTDOOR DYNAMIC RARELY FOUND IN TODAY'S REAL ESTATE MARKET. THE MAIN HOUSE OFFERS 5 BEDROOMS, 6 BATHROOMS, A BEAUTIFULLY APPOINTED LIVING AND DINING ROOM WITH PERIOD DETAILS, SEPARATE OFFICE WITH WET BAR AND FIREPLACE, LARGE SPACIOUS KITCHEN, ADJACENT FAMILY ROOM WHICH OPENS TO THE SUNNY YARD AND POOL, A LARGE GUEST SUITE IS ALSO LOCATED ON THE MAIN LEVEL. THE UPPER LEVEL OFFERS A LARGE PRIMARY SUITE WITH SITTING ROOM, AND WELL-APPOINTED PRIMARY BATHROOM, PLUS (2) ADDITIONAL BEDROOMS WITH JACK AND JILL BATHROOM. ON THE LOWER LEVEL YOU WILL FIND AN AU PAIR SUITE, WINE CELLAR, AND LARGE ATTACHED GARAGE. THE SPACIOUS YARD INCLUDES A SEPARATE POOL HOUSE WITH SAUNA, KITCHEN AND FULL BATHROOM. IN ADDITION, THERE IS AN ADJACENT 2+ CAR GARAGE PLUS PLENTY OF SPACE FOR A GYM.

Verdant retreat of 1.4 acres in the heart of prime Hillsborough. This sophisticated home has views of trees from nearly every room. A voluminous foyer with a focal picture window looking onto lush foliage introduces the bright open interior with soaring ceilings, spacious, elegant formal rooms, 3 bedroom suites with walk in closets (2 are primary suites), & a kitchen updated with center island, all new appliances (Thermador range, Bosch refrigerator + dishwasher & wine cooler) opens to a big eat in kitchen and sizable family room. An office or library off the main hallway can be closed off or open to extend the living room and a perfectly situated powder room serves the common areas. Other remarkable features include: 3 car garage, AC, Generator, laundry room, huge primary bathrooms & closets, loads of storage & a backyard large enough & private enough to feel like you are in your own forest. Create your own hiking trail & enjoy nature or develop the land - so many possibilities!

Introducing 585 Remillard Drive, Hillsborough, CA: a synthesis of luxury and refined Californian living. Spanning 4,214 sq ft, the main home invites with 4 bedrooms, 3.5 baths, and a spectacular chefs kitchen, embodying an aura of opulent design and functionality. An attached guest house provides 2 additional bedrooms, 1.5 baths, and a full secondary kitchen, with French doors revealing a bridge to lavish outdoor living. On a 22,000 sq ft lot, the backyard unfolds a mesmerizing oasis: exotic palm trees, impeccable landscaping, a cutting-edge pool and hot tub, and elite outdoor entertaining amenities. A resplendent offering where every detail narrates a story of luxury.

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 hall, and the Morocco Room lounge. Upstairs, the large master suite enjoys equally stunning views of the bay, in addition to a luxury spa bath and formal sitting room. A separate in-law suite and wine cellar with tasting room are located on the lower level of the residence. Equally impressive are the surrounding grounds, fully landscaped with grand-scale trees, expanses of manicured lawn, and an elevated terrace overlooking the views and swimming pool. All of this just minutes from shopping, dining, golfing, parks, and top rated Hillsborough schools. (Square Footage Per County Records: 8,629)

HUGE PRICE REDUCTION!!!!!!! SERIOUSLY, ONLY $975 PER SQFT+/-!!!! SELLER WANTS TO SELL, BRING IN ALL OFFERS!!! You're not going to want to miss out! The bright, flowing indoor floor plan has been tastefully updated and is move-in ready. The home carries the dual-pedigree of San Francisco design pioneers architect Gardner Dailey and famed landscape architect Thomas Church. The indoor living areas naturally extend through French doors from the spacious main hall into a landscape of ambling paths under mature oaks, welcoming rose gardens, and shaded lawns. The circular terraces and circular Emerald pool are signature Church design elements as featured in Architectural Forum magazine and two Thomas Church books.

Elegance abounds in this original William Wurster design that was expanded and restored to perfection by renowned local architect Farro Essalat. Tucked away on approximately .73 acres of outstanding, verdant grounds, 989 Hayne Road is a rare gem that is to be cherished for generations to come. Every feature of this five bedroom, five and one-half bath home offers the highest level of design, impeccable attention to detail, and masterful craftsmanship. The welcoming foyer with beautiful curved staircase is a fitting prelude to the grandly-proportioned interior spaces, which include a library, billiard room, huge family room and mud room. The delightful flow of this exceptional home extends to the incredibly manicured grounds, offering beautiful planter beds, tranquil garden pathways, a rose garden, fire pit, superb outdoor kitchen, and spa with beautiful views. This magnificent estate presents a unique opportunity for the discerning owner seeking that special, one-of-a-kind property.

Spacious & elegant, this Hillsborough beauty showcases luxury interior design complimented by gorgeous outdoor living. The grove of heritage olive trees beckons as you enter the spectacular courtyard with its rose garden, calming fountain & private patio. Anchoring the home is the remodeled kitchen with Carrara marble counters, custom cabinetry, stainless steel appliances, Wolf range & artisan tile. The living & family rooms are each warmed by a brick fire place. Step inside the fabulous butler pantry & attractive mudroom conveniently situated next to the large 3 car garage. Outside, a magical oasis awaits with the expansive backyard featuring fresh landscaping, new lawn, a pool, spa, & sport court with separate patio areas on the oversized .64 acre lot. This stunning Hillsborough home is close by downtown San Mateo & Burlingame with a variety of popular outdoor cafes, restaurants & shopping. Excellent schools and easy access to highways, Caltrain, Bart, & S.F. Airport.

Great opportunity! The residence overlooks a deep canyon containing Crystal Springs Road, next to San Mateo Creek, with peeks of San Francisco and the Bay in the distance. It is located in the Tobin Clark Estate neighborhood. Salmark Court is a small cul-de-sac with a total of four residences. The properties all flaunt modern, upscale looks as befits upscale properties in Hillsborough.The residence has a large living room, an elegant dining room, both displaying gorgeous chandeliers and intricate tile flooring. Straight ahead is a hallway leading to the kitchen on the right and bedrooms on the left. The family room sports a huge fireplace. There is an enormous banquet room with views of the canyon and the Bay. Master suite with hydro jet tubs and 4 more bedrooms; bathrooms are decorated with Italian tile - one has a steam shower. 2 fireplaces, 3 car garage s/s. There are both central forced-air and hydroponic heating systems. Swimming pool and spa. Needs TLC.

Over 1.8 acres, every square foot totally level, A perfect rectangle, Subdividable into 2 lots. One of only a few parcels of this size and quality in all of Hillsborough. Located in the most desirable location of lower Hillsborough among of some of Hillsborough's most beautiful estates. The perfect building site. When gone there will be no others.

This stunning 6 bed, 3.5 bath home is nestled in Hillsborough Park w/ lush landscaping, offering a rare opportunity to reside in a private & serene environment. Boasting approx. 6,161 sqft., this abode strikes a balance between grandeur & warmth. The interior features wood-beamed ceilings, skylights, large format windows, & wood decks providing breathtaking views of the surrounding hills. The main level features a family room (converted from garage), a chefs kitchen leading out to an open dec, formal dining, living room, & primary suite with a private deck. The lower levels features additional 5 beds, 2 baths, 2nd family room, deck area, media room, office, recreational room/gym, theater room, and storage areas. The manicured grounds are adorned with a diverse array of beautiful plants and pathways featuring a serene park like setting. This remarkable home provides an ideal combination of luxurious living, natural beauty, and a peaceful ambiance.

Extraordinary Hillsborough Estate in a Private Setting! Seemlessly blending the architectural splendor of a 1930's Spanish Hacienda with contemporary updates and resort-like amenities (pool, tennis court, cabana, and guest house), this cherished Hillsborough estate is perfectly situated on a gated lot of approximately 2.55 acres. The main residence exudes period charm with Gothic arches, groin-vaulted ceilings, and intricate tile and ironwork. The allure continues with nearly every room graced by a towering all-wood beamed ceiling and with access to the grounds or to a balcony. A soft neutral palatte creates a canvas ready for any personal style. Designed with lavish entertaining in mind, there are grand formal rooms, a spacious gourmet kitchen with top-tier appliances, an expansive family room, and a lower-level recreation room - each providing an ideal setting for gatherings of any scale. 5 bedrooms, each with its own bath, including a lavish primary suite. Lush gardens & setting!

A truly RARE LISTING that embodies opulence and exclusivity at its finest! IT DOESN'T GET BETTER THAN THIS SHOWCASE HILLSBOROUGH ESTATE! This once-in-a-lifetime property presents the perfect opportunity to live a life of luxury & sophistication, one you deserve! Tucked away at the end of a cul-de-sac in one of Hillsborough's most prestigious neighborhoods, seated on an over 1 acre lot. Commanding panoramic Bay views inside & out; from Downtown SF to the San Mateo Bridge. You get a front row seat to the true beauty of our world! The exterior is a testament to refined aesthetics & meticulous craftsmanship, embraced by meticulous landscaping & gardens + a glistening pool! The interior beacons w/ an air of elegance. Specially curated design elements include crown molding, bay windows, lighted tray ceilings, recessed lighting, & more! 6 rooms can serve as en-suite bedrooms. Two huge walk-in closet & multiple spa-like bathrooms. The kitchen is a culinary haven with all high-end appliances.

On the market for the first time since it was built 40 years ago, this home offers a wonderful opportunity for remodeling into your dream home or possibly building new. Situated at the end of a sought-after street in the coveted Skyfarm area, the home presents captivating canyon views plus some San Francisco Bay views from the upper level. Classic and traditional with vintage appeal, the home has two levels with spacious formal rooms and an open-design kitchen and family room. Upstairs, there are 3 bedrooms, including the primary suite. With an excellent location, beautiful surroundings, and an opportunity to create your dream home in desirable Skyfarm, this home is minutes from hiking trails and commuter routes, as well as highly regarded public and private schools.