Hillsborough CA Real Estate & Homes for Sale

Welcome to your luxurious retreat overlooking the stunning vistas of the Bay. This newly constructed masterpiece exudes sophistication and tranquility at every turn. Step inside to discover a haven of comfort and elegance, with an expansive primary bedroom thoughtfully designed from an inviting layout to its high-end finishes to create an environment where you can relax while enjoying breathtaking views. Crafted with meticulous attention to detail, this home boasts top-of-the-line features, including a wine storage room, spa with steam and dry sauna, and a state-of-the-art home theater. The gourmet kitchen, equipped with premium appliances and ample counter space, is a culinary enthusiast's dream. Relax in the infinity edge pool and spa while soaking in the mesmerizing views, or entertain guests in the outdoor area. With cutting-edge smart technology along with solar-powered solutions, green construction, air sealed and purified air supply through filtration, this residence offers unparalleled luxury, comfort, and efficiency. Elevate your hosting experience to new heights with a fully equipped guest house offering a private retreat for visitors, ensuring comfort and privacy during their stay.

Nestled on a spacious 0.52-acre corner lot, this home boasts potential to remodel, expand or rebuild. Inside enjoy large rooms that are bright and airy with a fantastic layout, ideal for multi-generational living or growing families. The main level features a formal living room, dining room, eat-in kitchen, family room, and three bedrooms. The lower level offers a huge bonus room for entertaining and additional bedrooms all with direct access to the large yard and pool. The spacious front and backyard includes large lawns, mature trees, a pool, and tree house. Located in the Carolands, this home offers quick access to Highway 280, Downtown Burlingame, and top-rated schools. Dont miss this hidden gem ready for your personal touches.

Situated atop a gentle knoll in the heart of Hillsborough, this immaculate ranch-style residence exudes timeless elegance and modern comfort. Admire sweeping bay vistas through towering windows gracing the spacious living area. The expansive kitchen, adorned with sleek cabinetry and a seamless island, seamlessly flows into the family room, creating a central hub for gatherings. Retreat to the luxurious master suite, featuring lavish Porcelanosa amenities and a serene ambiance. Step outside to discover a newly landscaped backyard oasis, ideal for alfresco dining and relaxation, with direct access from the family room via a sliding glass door. Revel in privacy amidst lush fruit trees and secure iron gates enclosing the yard. Additionally, a versatile bonus room in the basement offers the perfect space for a gym, entertainment area, or secluded home office. With the added allure of a formal dining space, this residence beckons you to experience its splendor firsthand.

RARE HISTORIC GEM, UPDATED FOR A MODERN LIFESTYLE! 1.42+ ACRES OF ALL FLAT LAND IN PRIME LOWER HILLSBOROUGH. Here you'll find a regulation tennis court, sprawling grass lawns, park-like fields / playgrounds, a sparkling solar-heated swimming pool, manicured gardens, & MORE! You can experience the epitome of timeless character and modern luxury in this one-of-a-kind English Tudor-style mansion nestled in the coveted Brewer Subdivision/Upland neighborhood, one of Hillsborough's most sought after areas. Old world charm suited for modern conveniences! MANY UPDATED AREAS THROUGHOUT. The grand foyer welcomes with antique oak floors and intricate crown molding, leading to sunlit rooms and multiple fireplaces. A recently refreshed interior features a kitchen blending old-world charm with high-end stainless steel appliances and leaded glass windows. Upstairs, the luxurious master suite offers a private sitting room or office, complemented by individually designed bedrooms and updated bathrooms. Inside you'll find 6 EN-SUITE BEDROOMS, perfect for hosting friends & family. Enjoy the convenience of being near downtown San Mateo and Burlingame, countless top schools, and a tranquil cul-de-sac setting, epitomizing the BEST HILLSBOROUGH HAS TO OFFER! This is one you'll want to see in person.

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 baths, fully equipped media room, home gym & upstairs sunroom w/ solarium balcony access. The multi-level layout wraps around meticulously designed gardens, offering picturesque views throughout. The exterior features over half an acre of vast garden space. Enjoy the ivy-covered trellis, elevated terrace with heated saltwater pool & spa & rolling grass-covered yards. Garden pathways lead to a charming children's play area. Mature trees surround the property, ensuring complete seclusion and privacy. Located in the prestigious Lower Hillsborough area, this property sits on a private, quiet street w/ no through traffic. Excellent Hillsborough North schools are a significant draw for families, while the proximity to downtown Burlingame & San Mateo ensures you're never far from amenities. Quick connections to international airports, San Francisco, & Silicon Valley add to the convenience.

Soon newly remodeled with a beautiful palette of materials, modern updated kitchen, baths & floors. Natural light with gourmet modern kitchen, high-end appliances, large breakfast area with French doors to the backyard. Featuring 4 bedrooms, 3 baths, 3,172 Sq Ft. Spanning a generous 31,799 Sq Ft lot. Desirable private large lot. Discover an unparalleled opportunity in Hillsborough, one of Silicon Valley's most prestigious neighborhoods. Potential option to build an ADU with a separate entrance from View Haven Road. Centrally located, in a highly sought-after area known for its distinguished schools. Highly rated West Hillsborough Elementary School K-5 is just .6 miles away. A rare gem in Hillsborough.

Regally positioned on 2.6 acres with stunning views of the San Francisco Bay, this palatial residence evokes the Olde English countryside. Built in 1930 and home to just a few families, the Tudor mansion has been masterfully restored and expanded. It boasts nearly 15,000 square feet of seamless living space, featuring an 8-bedroom main residence and a 3-bedroom guest wing with a great room, full kitchen, and laundry room. The home's heritage shines through with leaded glass windows, random plank hardwood floors, and an elaborately detailed relief plaster ceiling in the grand living room. Modern amenities include air conditioning, an elevator, backup generator, whole home audio system, programmable lighting, a fitness center, a theatre, and a chefs kitchen open to a spacious family room. The resort-inspired rear grounds feature a stunning pool with 185-foot waterslide and spa, sweeping lawns, and a lighted tennis court with two viewing pavilions. Designed for indoor/outdoor living, the grounds include a catering kitchen, pool cabana, and outdoor barbecue kitchen. Manicured gardens invite strolling and lingering, offering captivating views. Grounded in history yet perfectly suited for todays lifestyle, this grand residence is perfect for creating memories for generations to come.

LOWER HILLSBOROUGH'S PREMIER ESTATE! Rare listing, a once-in-a-lifetime property w/ one of the LARGEST LOTS in its neighborhood -- 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. There's a Detached 5-car garage with a 1br/1ba ADU and private executive office / conference room. Details outside include a regulation tennis court, 2 separate spas, in-ground Pebble-Tec pool surrounded by flowering plants, A HUGE LAWN, multiple patios, a terrazzo terrace, vast motor court, statues by legendary sculptor Gaston Rognier, pristine landscaping by renowned designer Thomas Church, multiple gardens / flower beds, AND SO MUCH MORE! Additionally, the electrical, plumbing, heating, air conditioning, roofing, irrigation, and exterior lighting have all been upgraded. Inside you'll find a large formal living room & dining rooms, a chef's kitchen, elliptical staircase w/ 40ft high entry, many 13ft high ceilings, butler's pantry, garden room, music room, a whole house 22kW generator, smart electronic lighting, elevator, roof deck w/ stunning views, multiple retreat en-suites, AND MORE! This you have to see to believe!

This architectural masterpiece with 4-bedroom, 5.5-bath transports you into an oasis with serene canyon and pool views. Abundant living and dining spaces are adorned with European solid oak floors, Italian lighting, radiant heating, and soaring floor to ceiling windows for a plethora of natural light. Delight in a chef's kitchen featuring Sub-Zero, Wolf, and Bosch appliances alongside dual sinks, walk-in pantry, coffee/bar station, and a 17-foot island perfect for culinary creativity. Luxuriate in the master suite with Bay views from the private patio or unwind in the bathroom with double vanity sinks and a freestanding tub overlooking lush greenery outside. With additional two bedroom suites, two offices, and a guest room with a patio overlooking the pool, this home was built to delight family and guests. Enter the outdoor paradise through enormous glass sliding doors and you'll be greeted by a covered patio with heaters, skylights, BBQ station, pool, gym, full bath, and firepit. The home also boasts solar panels, Tesla Powerwall and charger, and more for year-round enjoyment.

ATTRACTIVE SELLER FINANCING AVAILABLE TO QUALIFIED BUYER. Spectacular Custom Contemporary 6 bed/6.5 bath in highly coveted lower Hillsborough. Filled with natural light & clean line finishes, this spectacular property is set in a well-manicured verdant tree-lined large corner lot. Stunning architectural features of stately columns, soaring ceilings, and artful use of natural stones of marble, granite & sandstone set the tone for this sophisticated showcase of a home. The design and layout of this home epitomize California living at its finest. The open-flowing floor plan and strategically placed bedrooms, office areas and entertaining areas allow for an effortless combination of family living & entertaining. Boasts indoor/outdoor access to an extensive covered gazebo overlooking the fabulous level yard featuring a sophisticated pool and full workout room The chefs kitchen features a large center island, custom cabinetry, smooth granite counters, large stainless professional range, and flows into an inviting family/great room. The primary suite features a spa-like bath and large walk-in closets. Additional features of this fantastic home include electric gates leading to semi-circular drive and 4 car garage, expansive home office with custom built shelving and 2 media/ game rooms.

Luxury and Comfort. This Hillsborough gem offers Spectacular Panoramic Bay & Canyon Views from nearly every room! As you enter the house, you will be greeted by a Grand living and dining area featuring a spacious open floor plan, soaring high ceilings, elegant skylights, expansive windows, & glass doors that showcase the breathtaking views that this house offers. The adjacent chefs kitchen is a masterpiece, boasting ample cabinetry, a center island with a built-in sink, a breakfast bar, a second dining area, and a cozy family room w/ a fireplace. After a long day, retreat to one of the several comfortable & relaxing bedrooms. The master suite offers a serene escape w/ picturesque views & a harmonious primary bath with soaking tub. The rear exterior extends the length of the living spaces, providing a versatile and inviting outdoor area for leisure and entertainment. Enjoy a large back deck, patio, and BBQ area, perfect for relaxing and soaking in the breathtaking views from the privacy of your backyard. With its exquisite design, spacious interiors, and a backyard oasis featuring every amenity you could desire, this home offers a lifestyle of comfort and opulence. This house is only less than a 10-minute drive from Downtown Burlingames array of popular shops, restaurants.

Nestled on over 2 acres of meticulously tended gardens, 2275 Summit Dr epitomizes refined elegance & timeless charm. This shingled Craftsman residence blends original architectural integrity w/ contemporary luxury. Entering through the Palladian door, the grand foyer w/ rich old-growth redwood paneling sets the opulent tone throughout. The living room, featuring a cathedral ceiling w/ rustic beams & a wood-burning fireplace, offers sun-drenched windows with garden views. The adjacent dining room, wrapped in redwood paneling, is perfect for elegant gatherings. The kitchen features custom cabinetry, butcher block countertops, & a vintage OKeefe & Merritt gas range. The family room's Carrara marble fireplace adds to the home's charm. Upstairs, the master suite boasts a sky-lit sitting room & marble fireplace, providing a tranquil retreat. Additional bedrooms offer ample space for family & guests. The gardens feature over 100 species of flora, pathways, a pool / spa, a vegetable garden, & sprawling lawns. A 1br/1ba (405SF) cottage & AN UPDATED 3br/2ba (1,680SF) gatehouse offer luxurious accommodations. Located in north Hillsborough, this residence offers tranquility & easy access to shopping, dining, and more. 8,785 SF INCLUDES Cottage & Gatehouse. MUST SEE IN PERSON to experience!

THE BEST DEAL YOU'LL FIND IN LOWER-MIDDLE HILLSBOROUGH! The bright, flowing indoor floor plan has been tastefully updated and is COMPLETELY 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. Out back you'll find a brand new semi-circler lawn area. To the side of the property, a vast grass field perfect for events and children. Inside, you'll find a well-appointed updated kitchen, a bright & spacious living room, family room, multiple en-suite bedrooms, spa-like bathrooms, a craftsman office / library, & more. Heading back outside, you'll find several balconies with views of the surrounding woods, as well as a patio area just off the living room. With this location, you're close to Downtown Burlingame as well as several prestigious public & private schools.

Discover upscale living in this 3520 sq ft Hillsborough residence, featuring a beautifully updated kitchen with high-end Thermador appliances, eat-in area, wine bar, skylights, and formal dining room. The expansive, light-filled living room with vaulted ceilings elevates the home's elegant interiors. The first-floor primary suite has high ceilings and boasts a vast walk-in closet and a spa-like bath with luxurious tubs and showers. The lower level offers a bedroom suite, two additional bedrooms, a homework station, and a separate laundry room with wine storage. The extensive 38,332 sq ft lot includes an outdoor kitchen, fountain, fire pits, and a lush garden, perfect for hosting gatherings. Additional amenities like a kids' play area, putting green, bocce ball court, and basketball court cater to an active family lifestyle. This property combines luxury with functionality, making it an ideal choice for those seeking a sophisticated yet comfortable living space. Enjoy the serenity of a well-appointed home nestled in a prestigious neighborhood, designed to cater to every need of a discerning homeowner and with 3 of the bedrooms being walk-in level, it's perfect for those seeking multi-generational comfort. An exceptional opportunity to own a family haven in Hillsborough awaits.

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 boasts 5 bedrooms and 4 bathrooms, with the added bonus of a brand new ADU that includes the 6th BR and another bath. Inside, discover 16-foot ceilings, stunning wood floors, abundant natural light, and premium upgrades. The chef's kitchen features Thermador appliances and an 11-foot island, with La Cantina doors for seamless indoor-outdoor flow. Additionally, your outdoor oasis awaits with ample space for a potential pool, while the bocce ball court adds a touch of recreation. The additional 763sf ADU is versatile, perfect for guests or a home office. This property combines modern living, luxury, and space in the sought-after Carolands neighborhood. Welcome home!

Every once in a while, a true opportunity presents itself...This Mediterranean masterpiece, feat. rare & spectacular Bridge to Bridge Views, the San Francisco Skyline, Bay Bridge, East Bay Hills, San Francisco Bay, San Mateo Bridge and more at your fingertips! Offering a pristine parcel of land, situated close to downtown, schools, parks, transportation. Here are just some of the attributes to contemplate...Lower Level: Grand Formal entry w/ high ceilings & marble floors, Commanding Living Room w/ Bay Views, full bar & fireplace, Informal Family Room with fireplace, Bay Views and convenient access to the back yard, Spacious Dining room with immediate proximity to the Kitchen, Gourmet Kitchen featuring top quality appliances, natural stone countertops, heated flooring, eat-in area & back yard access, 2 Ground floor suites each w/ spacious bedrooms, hardwood floors & updated bathrooms, Full Laundry facility conveniently located off the Kitchen area. Upper Level: 3 more spacious bedrooms, Expansive Primary Bedroom Suite feat. commanding Bay Views, vaulted ceilings, fireplace, office respite, updated primary bathroom. Outside: Sublime Back yard feat. swimming pool, spa, built-in BBQ/kitchenette, putting green, lawn & entertaining patio, outdoor fireplace & mouth dropping Bay Views!

Over 1.1 Acres of flat Lower North Hillsborough Property. Possible sub-division into (2) separate parcels, call Nick for details. This stately traditional-style 6,000+/-square foot home is located in Prestigious Fagan Estates. This stunning five bedroom, four and two half bath estate features an expansive living and dining room with grand picture windows and an abundance of natural light, a large family room and a contemporary kitchen. In addition, enjoy a wood-paneled library, a separate office and an amazing indoor/outdoor glass-enclosed pavilion that overlooks a nearly half-acre Japanese garden. There is room for all with an expansive first-floor primary suite with a sitting area and plenty of closet space. Four additional bedrooms complete this home. The rear Japanese Garden was designed by Renowned Landscape Architect Katsuo Saito. Enjoy over 20 heritage trees including Cut Leaf Maples and Black and Red Pine Trees. An iconic 10,000-bottle wine cellar, temperature controlled at 48 degrees and humidity controlled at 70%.

This exquisite three-story villa is nestled on nearly two acres of stunning gardens that capture the essence of Italy. The villa features interiors of unmatched quality with materials sourced globally, including fine woodwork, sleek lighting, and premium natural stone that exemplify modern sophistication. The grand entrance welcomes you with high ceilings and an office adorned with coffered ceilings. The master bathroom showcases a remarkable old-world charm. The state-of-the-art kitchen is equipped with a large island, and the lower level boasts a wine cellar, a full bar, and spaces for entertainment and media. Balconies, patios, and terraces offer views of a resort-like backdrop. The home is equipped with radiant heating, Sonos sound system, and a video security system. An outdoor kitchen with a dining bar, three fireplaces, and a saltwater spa enhance the luxurious outdoor living. Secluded by the orchard, there is a one-bedroom, self-contained guest house with an eat-in kitchen. This estate offers vast space, privacy, and opulence, making it a rare gem on the market.

This modern masterpiece, built in 2018 embraces mid-century aesthetics and design principles in Lower Hillsborough on a secluded half-acre. Designed by Nancy Sheinholtz Associates, the home is surrounded by redwoods and features a modern facade of stainless steel and stone. Inside, polished concrete floors and glass walls underscore the modern vibe. The layout promotes indoor/outdoor living with retractable glass doors connecting the spacious great room to the outdoor pool area. The kitchen is a modern culinary space with top-tier appliances. There are 5 bedrooms, each with its own bath, plus an office. Main-level bedroom suite, upstairs primary suite and two additional suites, plus a private upstairs multi-room suite near an outside entrance offers flexibility for remote work needs or extended family/guest quarters. Outdoor entertainment is a breeze with a large pool, fire pit, and barbecue kitchen. Midway between San Francisco & Silicon Valley. Excellent public and private schools.

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.

Modern elegance meets unrivaled luxury. This modern luxury masterpiece epitomizes elegance and sophistication situated on a sprawling two acre lot, this estate includes a guest house boasting opulence at every turn with a pool overlooking views that are unmatched. Marvel at the grandeur of 26-foot ceilings and european oak floors as you enter connecting to the gourmet kitchen, adorned with cambria countertops and top-of-the-line gaggenau appliances beckoning culinary excellence. Entertain effortlessly in the game room, indoor/outdoor bar, and gym while indulging in relaxation in the sauna or luxurious jacuzzi tubs. The exterior of this estate adorns european garage doors, italian windows, and a stunning limestone terrace connecting to stunning bay area views. Experience modern luxury living at its finest in this extraordinary residence.

Over 1.8 absolutely level acres, one of only a few parcels of it's size in all of Hillsborough. The merging of two .9 acre lots, the parcel totals over 1.8 acres and can easily be subdivided into 2 lots. Located in the most coveted location in lower Hillsborough, 210 Uplands sits across from some of Hillsborough's most beautiful estates. A once in a lifetime opportunity. When gone there will be no others.

ONE OF HILLSBOROUGH'S FINEST PROPERTIES!!! Breathtaking views of the San Francisco bay & beyond. HUGE MOSTLY LEVEL LOT WITH OVER .5 ACRES. Exquisite Mediterranean design complemented by 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 left of the foyer, a refined living room with a tasteful fireplace. On the right, a great room that integrates both the kitchen & dining area and family room; ideal for hosting guests. The high-end, modern chef's kitchen is a culinary haven, equipped with all top-of-the-line stainless steel appliances, a large center island with quartz countertops, a wine cooler, and more! There's multiple spacious en-suites including a luxurious primary with a spa like bathroom. Step outside to one of several balconies with stunning views of the San Francisco Bay. Rounding out the list of amenities is the backyard with a sparkling pool and expansive lawn. Also, you'll find several patio sections and a BBQ area. There's so much to say about this home. For those seeking a residence that encompasses luxury and practicality, this is it. You'll also get access to prestigious schools and the convenience of Highway 280.

Indulge in the epitome of luxurious living with this newly renovated Hillsborough estate, offering breathtaking views of the San Francisco Bay. Custom-built in 2000 and recently transformed into a transitional modern design, this residence offers natural light throughout and boasts 6 generously sized bedrooms and 6 1/2 baths. Enter through a formal foyer with a sweeping stairway, setting the tone for the elegance within. Two primary suites with expansive views, provide a serene escape. Pamper yourself in the primary suite's steam shower, offering a spa-like retreat within the comforts of home. The open kitchen-family room floor plan is a showcase, featuring top-of-the-line brand new appliances, custom cabinetry, perfect for both daily living and entertaining. An office with a cozy fireplace adds warmth and charm, while an elevator ensures convenience across multiple levels. The property includes a 3-car garage, a gated and private driveway that provides retreat-like ambiance. Experience California elegance and luxury at its finest, conveniently nestled between SF and Silicon Valley. Enjoy the advantage of top-rated schools, as well as proximity to a myriad of restaurants and shops. Additional bedroom (permitted) added during remodel.

This opulent mansion stands as a veritable icon in Lower South Hillsborough, meticulously crafted as a homage to the White House by the esteemed architect Julia Morgan. Spanning over 24,000 square feet across four levels, it has been thoughtfully rejuvenated with the finest fixtures and state-of-the-art appliances. With its Neoclassical Georgian architecture, the home greets you with majestic columns and an impeccably laid driveway, the facade exuding grandeur. Inside, an abundance of windows and soaring ceilings invite the warmth of California's sun, bathing each room in natural light. Timeless accents such as intricate crown molding, resplendent wood floors, and dazzling chandeliers seamlessly marry with contemporary elements and sleek lines, epitomizing sophistication. Ascend to the primary bedroom, where a regal fireplace, a tranquil sitting area, and an opulent ensuite bathroom await, adorned with dual sinks, a sumptuous soaking tub, and a separate shower. A sanctuary for productivity, the home office boasts two-toned wood paneling and an imposing desk. Nestled upon nearly three acres of verdant grounds, the Bay Area's 'Western White House' is a testament to refined living and illustrious entertaining.