Hillsborough CA Real Estate & Homes for Sale

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.

ARCHITECTURAL MASTERWORK OF EUROPEAN GRANDEUR...Handcrafted in 1928 and since masterfully expanded and remodeled, this Bay-View Mansion evokes the legendary estates of Beverly Hills. Spanning 8,670 sq. feet of pure quality and character, this is a statement for all centuries. The home takes its place on a storybook street of minimal traffic, shouldered by other picture-perfect estates, only 1.4 miles to downtown Burlingame Avenue and just 1.1 miles to North Elementary. Two influential movements of the 1920s were Tudor Revival and Storybook Style. This home artistically synthesizes both genres into one grand entertaining platform. *Ceilings soar to 25 feet. *Monumental lobby foyer of herringbone floors & spiral staircase that towers to 22 feet. *Custom Library + Separate Office *In-Law Apartment *Pro Wine Cellar *Architectural Significance Throughout *Loft Level for Gym/Playroom *Bay-View Primary Suite of 18 ft. ceilings *Epic Rooftop Deck with Heroic Bay Views to SF *Prime Estate Loc

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.

Step into "Chteau de Vue," your sanctuary of unrivaled luxury and panoramic vistas, nestled atop Hillsboroughs prestigious enclave. This 8,265 sq ft architectural masterpiece offers an extraordinary blend of 7 opulent bedrooms, 6 spa-like bathrooms, and a finely crafted executive office. Revel in the grandeur of your own Roman Empire-inspired family room connected seamlessly to a top-of-the-line chefs kitchen. The sumptuous primary suite stands as a realm unto itself, boasting a lavish en-suite and a private balcony with breathtaking views from the Bay Bridge to San Francisco, the Peninsula, and Oakland. Beyond the interiors lie two impeccably designed outdoor kitchens, one for tranquil mornings overlooking panoramic vistas and another perfectly suited for grand entertaining. Athletic amenities abound with a private tennis court and professionally equipped wellness gym. An additional 650 dwelling unit offers versatile possibilities for guests. Centrally located to everything.

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.

One of Hillsborough's premiere newer estates, this 2017-built residence combines elements of an exquisite French Chateau with a fresh contemporary design. Chic finishes meld seamlessly with elegant transitional elements in grand-scale indoor/outdoor spaces to create the epitome of contemporary living- all tied together by a colossal 3-level high central atrium with a floating staircase on a scale rarely seen in any of the world's most exclusive private residences. Set high on the lush Riviera-style hills in the heart of one of the most desirable residential enclaves in the San Francisco Bay Area, this serene oasis enjoys beautiful grounds, a sports court & putting green, as well as resort-like amenities including a gym with sauna, billiards room, wine cellar & media room. Sweeping views over the rolling hills, with the Bay providing a shimmering backdrop to the lights of Silicon Valley & the S.F. Skyline, are magically framed by the lush greenery surrounding this magnificent residence.

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.

Introducing a luxurious and contemporary masterpiece situated in the prestigious Hillsborough California. Located at 1175 San Raymundo.This stunning new construction, completed in 2023, offers a grand living experience with its generous proportions and high-end finishes. Spanning over 5200 square feet, this expansive residence boasts six exquisitely designed bedrooms, providing ample space for relaxation and privacy. The seamless integration of indoor-outdoor living is a defining feature of this home. Step onto the decks or multiple terraces, thoughtfully designed for entertainment and enjoyment, where you can savor breathtaking views of the surrounding natural beauty. These open-air spaces provide an idyllic setting for hosting gatherings, enjoying sunsets, or simply unwinding in the fresh air. No expense has been spared in crafting this modern gem. The interior spaces are adorned with top-of-the-line materials and high-quality finishes, creating an atmosphere of sophistication and elegance. The floor plan is intelligently designed, incorporating open-concept living areas that flow harmoniously, allowing for a seamless lifestyle.

Introducing a masterpiece of luxury living at 3 Mountain Wood Lane! This exquisite gated estate redefines elegance, spanning across a landscape with captivating gardens, 2 outdoor dining spaces, fire pit, infinity pool and complete privacy. Step into the heart of culinary artistry with a chef's kitchen featuring a Thermador range, stainless steel appliances, and an oversized island for both preparation and casual dining. Enjoy the seamless flow from the kitchen to the great room with a massive stone fireplace and access to the outdoors. The main level is complete with a magnificent wood-paneled office and ensuite bedroom. Upstairs features 4 additional en-suite bedrooms including an oversized primary suite with separate office and laundry. Indulge in the epitome of outdoor living with an outdoor kitchen, a heated al fresco dining area, swimming pool and more! 3 Mountain Wood Lane is not just a home but rather a lifestyle statement.

Mid Century House of Wonders! Full of possibilities and absolutely irreproducible assets, this Hillsborough classic offers an incredible 1.07 ACRE, 100% USABLE LOT! 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 nearly level land in preferred Carolands. At the corner of Ralston, shouldering multi-acre eight-figure estates, and drenched in sun!. Walls of glass inside a luminous interior reveal a hidden courtyard pool terrace & Guest Unit. Beyond the pool, an unbelievable surprise awaits: raw untouched land extending all the way back, ready for expansion of the existing home, new construction, tennis court, and future huge ADU. 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, expansion, or new construction at these Legacy Lands.

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.

Regally set on 2.8 glorious acres on iconic Robin Road, this custom built estate has a total 10,400 Square feet of luxurious living area. This home is like NEW. Seldom used by owners. Industrial quality construction top to bottom. Priced millions below replacement cost. Inside are 5 bedroom suites including a huge primary suite with 2 bathrooms, and 2 walk-in closets. Additional rooms include a baronial scaled foyer, grand living and dining rooms, separate music room, family room, media room, professional kitchen and breakfast room, all opening onto limestone terraces, the manicured grounds and gardens, sunny pool and tennis court, plus the original Redwood Grove from the Carolands estate. Reached through a Porte Cachere, is a 4 car garage and massive motor court.. Built for the owners as the Ultimate dream home, no expense was spared, no detail overlooked in creating this amazing home that, by any definition, is world class. To view this home is an experience one will never forget.

$550,000 PRICE REDUCTION! 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 MEDITERREANEAN DESIGN CELEBRATES IMPRESSIVE ARCHITECTURAL DETAIL RARELY FOUND IN HILLSBOROUGH. 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.

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.

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.

Impeccable home located in prestigious Hillsborough. This gated property includes a living room/dining room combination with fireplace, laundry in kitchen, 1-car garage & dishwasher. The home will be in move-in condition, vacant and ready for occupancy on Sept. 1, 2023.

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!

FIRST SHOWING IS ON JUNE 27TH. This well-maintained 2-story home with 4 bedrooms, 3.5 baths, seated on an expansive 87,120 sqft* lot. All the main rooms are situated upstairs, providing privacy and breathtaking views. As you enter, the left side offers a living room with high vaulted ceilings, a fireplace, and a sliding door leading to a balcony showcasing spectacular views. On the right side, an elegant half bath, wet bar, & formal dining room await. The updated kitchen boasts high ceilings, granite countertops & backsplash, an island, and stainless steel appliances. Adjacent to the kitchen, a family room with a sliding glass door opens to a balcony overlooking the inviting swimming pool. Downstairs are the 4 bedrooms, each w/ backyard access, including a master bedroom w/ a gorgeous master bath & walk-in closet. The laundry is conveniently located in the hallway. The backyard is a haven for outdoor entertainment, featuring a large pool, pool house, tennis court, & expansive garden.

Newly renovated Hillsborough estate with views of the SF Bay. Custom built in 2000 and recently renovated from top to bottom in a transitional modern style featuring 6 generously sized bedrooms and 6 1/2 baths. Two primary suites with expansive views, steam shower in primary suite, formal entry with sweeping stairway adjacent to the living room and dining room, open kitchen-family room floor plan with top of the line brand new appliances, custom cabinetry, study or office with a cozy fireplace, elevator, bonus room to be used as a home theater or exercise/entertainment room, 3 car garage, and an abundance of natural light throughout the thoughtfully reimagined home. Gated and private driveway that offers a retreat from the street. California elegance and luxury conveniently situated between San Francisco and Silicon Valley with top rated schools, and an abundance of restaurants and shops nearby.

Magnificent Mediterranean Estate with 6 bedrooms, 6 bathrooms, plus an additional two half bathrooms/Soaring ceilings with custom skylights provide an abundance of natural lighting over the dramatic entry that features grand columns and graceful staircases with custom ironwork and a cascading water wall feature/Spacious Primary bedroom with high coffered ceiling, bold crown molding, fireplace, a separate walk-in closets and spacious main bathroom that features a large shower with dual heads and a separate tub/Sizable office/study with cozy fireplace and built-in bookshelves that are blessed with an abundance of natural lighting from multiple sides/The resort-style backyards is perfect for entertaining and relaxing. Dramatic views of San Francisco Bay and beyond can be enjoyed from the spacious terraces and patio that surround the huge refreshing pool and jacuzzi. Other feathers include a sports court, water fountains, fireplace, and fire pit. A spacious gated driveway and 3-car garage.

This classic contemporary home enhances the owner's daily routine: four large bedrooms, a beautiful bathroom, formal foyer, living room, and dining room provide residents with peace and quiet. Beautiful hardwood and tile flooring throughout the home. The kitchen has a great room concept with a dining area and adjoining family room. The appliances are also equipped to good specifications. A central vacuum system and convenient hallway laundry make indoor care easy, and the 3-car garage has custom built-in cabinets for all your storage needs. The property is ideal for family and friends gatherings indoors and out. Gently sloping grounds with fruit trees, terraces, and evergreens complete the image of this tranquil setting. Hillsborough schools are just a short distance away and shopping and highway access are convenient.

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.

PRIME LOWER HILLSBOROUGH LOT WITH .90 ACRES OF 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!!! 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 to BUILD YOUR DREAM HOME! 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!

Welcome 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.

Live at this luxurious home that provides you exciting amenities in a prestigious neighborhood of Hillsborough. Large flat usable land, Park-like garden, sparkling swimming pool, tennis court and more!