Hillsborough CA Real Estate & Homes for Sale

Indulge in the panoramic views of this stunning 3BD+den/3.5BA retreat in the sought-after Skyfarm neighborhood of Hillsborough! Step into the bright and airy living room, with vaulted ceiling and cozy fireplace, creating a captivating focal point for gatherings and relaxation. The adjacent formal dining room sets the stage for entertaining, while the eat-in kitchen provides the ideal space for culinary creativity. The seamless layout integrates indoor/outdoor living, with direct access from the living, dining, kitchen and primary suite to the expansive deck, offering breathtaking panoramic views of the bay and canyon. The bonus flex-use space of the office/den provides a tranquil retreat and a space for productivity. Downstairs, two additional bedrooms, two bathrooms, and a spacious family room all with sweeping views await, offering flexibility and privacy. Outside, the property features two gathering garden areas, two large decks, and a concrete patio, perfect for outdoor enjoyment and play. This remarkable home is complete with a three-car garage, two separate heating zones and dual-paned windows framing the picturesque views. Conveniently located near top schools and easy access to 280, this home perfectly blends luxury and practicality. Welcome home!

Discover unparalleled value in this exquisitely crafted luxury new construction, offering the epitome of sophistication at an exceptional price point. Introducing a luxurious and contemporary masterpiece in prestigious Hillsborough, California, located at 1175 San Raymundo. Completed in 2023, this stunning new construction offers a grand living experience with generous proportions and high-end finishes. With over 5200 square feet, the expansive residence features six exquisitely designed bedrooms for relaxation and privacy. The seamless integration of indoor-outdoor living is a defining feature, with decks and terraces designed for entertainment and enjoying breathtaking views. These open-air spaces create an ideal setting for gatherings, enjoying sunsets, or simply unwinding in the fresh air. Crafted with no expense spared, the modern gem boasts top-of-the-line materials and high-quality finishes, creating an atmosphere of sophistication and elegance. The intelligently designed floor plan incorporates open-concept living areas that flow harmoniously for a seamless lifestyle.

This beautiful Tudor styled home is situated on a .57 acre lot, a 4BR/2.5BA home offers an attractive, functional floor plan. Perfect for entertaining, the kitchen and family room open to a large patio and backyard with an attractive view of the swimming pool and garden areas. The family room and fireplace sit adjacent to portion of the living room that can function as an office or additional living room space. A grand formal living room with a fireplace. The upper level features 4 generously-sized bedrooms, including a large master bedroom with a view. Outside, the grounds boast private, level grounds with access to a heated pool with spa, and a cabana with two changing rooms and a full bath. Conveniently located near downtown Burlingame and San Mateo, top-rated Hillsborough schools, and major commute routes.

Art + Nature in Perfect Harmony. Completion Summer of 2026. Secluded in exclusive Hillsborough, this modernist masterpiece, a three story wonder of glass that floats with the forest. Designed by acclaimed, award-winning architect Leonard Ng, the plans for this iconic 11,875 sq. ft. retreat are a meditation on minimalism, an extension from the trees that questions where nature ends & home begins. Clear heart red cedar siding opens to vast windows, soaring lines and engaging angles that lean into natural light & wide views. 7 en suite bedrooms, 9 bathrooms, a great room, wine cellar, fitness studio, wet & dry saunas, plus detached 800 sq. ft. guest house provide for exquisite living. A shimmering pool, phenomenal indoor-outdoor entertaining and meandering paths of curated native plants elevate life. Coveted location for top-performing schools, community & an ideal commute between San Francisco and Silicon Valley. See the world in a new light.

Explore mid-century modern luxury with this one-level, 3-bedroom plus office (or 4th bedroom), in this modern ranch home in prime Lower North Hillsborough. The open modern house plan features high ceilings, clean lines, hardwood floors, Fleetwood doors and windows that seamlessly blend indoor and outdoor spaces, with a stunning 40-foot floor to ceiling glass door expanding the living area to the resort style backyard with pool, and lush exotic tropical and desert landscaping. At night, the vast landscape lighting transforms the property into a breathtaking evening oasis. The gourmet kitchen showcases Sub-Zero/Wolf appliances, pristine, calcutta marble countertops, sleek white cabinets, and a large spacious island for gatherings. This large flat half-acre sunny lot offers expansion or ADU potential. Conveniently located near Burlingame downtown, Burlingame Country Club, and North and Crocker School, this property offers beauty, tranquility and or entertaining all in one place.

TREASURED LOWER HILLSBOROUGH ESTATE!!! A RARE GEM w/ A HUGE DOUBLE LOT & OVER 1.1 ACRES OF FLAT USABLE LAND! Host w/ confidence thanks to spacious living quarters & a separate 2BR/BA GUEST HOUSE. Sweeping lawns w/ lush grass. Pristine landscaping combined w/ 3 separate patio areas. Sparkling pool & spa + a Cabana. The exterior facade incorporates European elements such as Roman columns. Electronic gate w/ 3 entrances + lots of greenery for privacy & security. The perfect floorplan, a masterpiece of design & functionality. There's hardwood flooring, classic wainscoting, distinct chandeliers, regal fireplaces, crown molding, stained glass windows, recessed lighting, & more. Tall side windows light up the floorplan. Oversized living room & family room. The kitchen is a culinary haven w/ high-end appliances. Multiple ensuite bedrooms + a luxurious primary. Prestigious neighborhood w/ access to sought-after schools. ADRB approved plans for a brand new modern house (available upon request).

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.

ONE OF THE BEST VIEWS IN ALL OF HILLSBOROUGH! UNPARALLELED PANORAMIC BAY VIEWS from nearly every part of the house. 270 DEGREE+ UNOBSTRUCTED VIEWS! Experience breathtaking sunrises & sunsets right from the backyard. Embrace the good life w/ this one-of-a-kind showcase home. Contemporary design culminates w/ modern conveniences in a fantastic open floor plan; this is the pinnacle of luxury living! The home itself sits on an expansive 1.3 acre lot at the end of a private cul-de-sac. The sophisticated foyer sets the tone for the entire residence. Inside you'll find high ceilings, crown molding, recessed lightings, skylights, hardwood flooring, a semi-spiral staircase, central ac, a movie room, office, wine cellar, family room, wet bar, multiple en-suite bedrooms, high-end appliances, big living room, and more. The chef's kitchen is a masterpiece of design & functionality. There's a separate au-pair / in-law unit w/ its own access. There's a huge flat backyard overlooking everything!

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!

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.

Nestled in the heart of Hillsborough, this centrally located haven offers seamless access to the Peninsula job market. Updated open Chef's kitchen adorned with top-notch appliances. The home boasts spacious bedrooms, including two ensuite bathrooms and a convenient jack and jill bedroom layout. Additional features include ample attic storage, a roomy pantry, bedroom air conditioning for year-round comfort, new carpeting, and a sprinkler system for peace of mind. Set upon a generous 0.45-acre lot enveloped by mature trees, the backyard becomes an idyllic playground and an ideal space for entertaining with the built in bbq grill and spa. Nearby Burlingame, Millbrae, and San Mateo provide a diverse array of dining and services. Meanwhile, the peaceful neighborhood invites you to explore scenic walks and hiking trails. Exceptional schools, including the nearby Nueva School, ensure your educational needs are met. Experience the epitome of comfort and convenience in this Hillsborough gem.

YOUR ULTIMATE HILLSBOROUGH DEAL!!! MOVE-IN READY SHOWCASE! HUGE 2+ ACRE LOT, tucked away in a private setting! Ideal SINGLE-STORY floor plan w/ a bonus room @ lower lvl. Expansive flat backyard offers the perfect canvas to expand, add an ADU, or start from scratch. Catch a glimpse of the sea w/ partial Bay views. This property benefits from Hillsborough's top-rated schools, picturesque tree-lined streets, & close proximity to downtown. Tons of space for the entire family w/ 5 comfortable bedrooms & 3 bathrooms. The primary suite features a luxurious bath & access to the balcony. The living room has recessed lighting, a nearby dining area, & glass doors leading outside. The well-equipped kitchen is packed full of high-end stainless steel appliances. There's an extra-wide deck nestled under the trees. The bonus room can serve as a home gym, rec room, family room, etc. So don't miss out on the opportunity to call this home; a place where comfort, style, & a world of possibilities collide!

Longing for endless views and architectural drama? Look no further! This custom-built home ticks all the boxes, wood trusses and beamed ceiling, open floor-plan embraced by serene vistas, gourmet chef's kitchen, and more! Situated on a cul-de-sac, this unique property offers room for entertaining and privacy from the street. View-filled deck spans the width of the home. Host in-person or virtual meetings in the media room. Gather your crew for brainstorming or team building...there's room for all. Expansive primary suite with a built-in office area is only limited by your imagination. Secondary suite line with tatami mats can help you find your zen.

PHENOMENAL NEW PRICE!!! Say yes to $750 per sq ft for a classic Bay-View mansion assigned to North Elementary and within walking distance of Downtown Burlingame Avenue! And did I mention nice pool and INCREDIBLE BAY VIEW?! Best of both worlds with authentic Gatsby character, yet this house was painstakingly restored in the early 2000s to bespoke heights. Storybook street of minimal traffic, shouldered by other picture-perfect mansions, only 1.4 miles to downtown Burlingame & just 1.1 miles to North School. *Grand entertaining platform of architectural significance on 4 levels. *Ceilings soar to 25 feet. *Monumental lobby of herringbone floors & spiral staircase that towers to 22 feet. *Esquire Library + Separate Office *In-Law Apartment *2,000 bottle Pro Wine Cellar *Loft Level for Gym/Playroom *Bay-View Primary Suite of 18 ft. ceilings *Wow-Factor Rooftop Deck with Epic Bay Views to SF *Private motor court. Many curated pieces of artisan-carved furniture were designed for the house.

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.

HILLSBOROUGH'S ULTIMATE BUILDING SITE! EXPAND, BUILD NEW, or RENT & HOLD! Full of possibilities and absolutely irreproducible assets, this Mid Century Courtyard Estate offers an incredible 1.07 ACRE, 100% USABLE LOT! Not something you find every day, maybe only once in a decade! Capture 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 pool courtyard & 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.

This home offers outstanding value in a serene private setting on more than three-quarters of an acre. Located at the end of a sought-after street in the coveted Skyfarm area, there are captivating canyon views plus some San Francisco Bay views from the upper level. The home is classic and traditional spanning two levels and offers wonderful possibilities for updating. Spacious formal rooms are complemented by an open-design kitchen and family room with sliding glass door to a large deck. There are 3 bedrooms upstairs, including the primary suite. With an excellent location, beautiful surroundings, and an opportunity to create your dream home in desirable Skyfarm, this home also benefits from being minutes to hiking trails and commuter routes, as well as highly regarded public and private schools, including West Elementary and Crocker Middle.

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.

Price reduced by $200K. 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!

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.

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.