Hillsborough CA Real Estate & Homes for Sale

Remodeled Eat-In Kitchen | Separate Casual and Formal Living Rooms | Expansive Dining Room | All Public Rooms Form a Wonderful Great Room | Five Bedrooms including a Gorgeous Primary En Suite | Five Bathrooms and One Powder Room | Multiple Skylights | Three Fireplaces | Wine Cellar | Media Room | Architectural Details Throughout | Fenced & Gated Yard | New Bamboo Composite Deck (550 sf+/-) | Verdant New and Mature Landscaping | Mature Perimeter Trees | Stunning & Sculptural Oak Trees | Expansive and Fitted Garage (750 sf+/-)

SHOWCASE HILLSBOROUGH HOME REMODELED FROM THE STUDS OUT IN 2022! Never lived in since the remodel! Be the first to reside in such an elevated living experience. This home offers up-to-date contemporary designs with the finest appointments available; perfect for the modern family. Wide-open modern floor plan w/ tons of natural light thanks to tall windows & 3 skylights. The great room is huge and blends the living room/kitchen seamlessly; the perfect hosting platform. White oak hardwood runs from edge to edge. Recessed lighting illuminates ever corner. The brand new gourmet chef's kitchen has all top-of-the-line appliances from Thermador, Bosch, Sub-Zero, & more! You'll also find a center island w/ a built in sink & integrated appliances + quartz countertops. Easily master your culinary skills. All the bedrooms are ensuite & comfortable. Bathrooms feature polished quartz, rainfall shower heads, double vanity, etc. 2 AC units, 2 Furnaces, & a wrap around backyard/garden. DON'T MISS OUT!

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.

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 92/280/101, Caltrain, Bart, & S.F. Airport.

Charming single level home on a secluded .74 acre lot with pool. 4 bedrooms, 3.5 baths, family room. Car collectors dream, 6 car garage. Lower South Hillsborough location very close to Crystal Springs School. Move in and update or remodel, new plans working on final approval from City.

2.5+ acres in the heart of Hillsborough! This architecturally magnificent gated estate is nestled at the end of long private driveway and is on the market for the first time in almost 50 years! Situated on secluded park-like grounds, this structure is a work of art featuring uninterrupted style and craftsmanship that blend an array of materials, unique finishes and unsurpassed woodwork throughout. Highlighting the integration of indoor and outdoor spaces, this house features a front courtyard, open loggia corridors, lofty timber-beamed ceilings, pool house and cabana, oversized pool, tennis court, al fresco dining patio, garden terraces, magical strolling paths and impeccable grounds.The main house is approx 6,310sf with 5 bed/5.5 baths; the two additional structures have a combined 1,000sf (approx) with 1bed/1bath. This Hillsborough home feels like you are away from it all even though it's just minutes from major freeways, Silicon Valley and San Francisco.

A gated herringbone brick entry and manicured garden present a picture-perfect introduction to this private setting. Inside, deep crown molding and mahogany hardwood flooring appoint light-filled, generously sized rooms. An expansive living room with fireplace flows across the entry foyer to the formal dining room. The charming breakfast nook opens one of several patios. Featuring brilliant natural light, the chefs kitchen blends beauty and functionality. Nearby, the family room with its built-in media cabinetry and hand-hewn cross beam ceiling, opens to the resort-style rear patio and grounds. A powder room and full bedroom suite complete this level. The distinctive staircase leads one upstairs to the grand primary suite with fireplace, spacious bath & dual walk-in closets. 3 additional bedrooms and 2 marble baths surround a central hallway. Amenities include Lutron lighting, lush and well lit landscaping, sunny pool, hot tub and fully equipped outdoor kitchen. Your private oasis!

RECENTLY REMODELED! Classic architecture & superb craftsmanship seamlessly work w/ the latest appointments & amenities. The sought-after neighborhood Hillsborough Oaks offers the perfect backdrop to this private home. The sophisticated interior is bright, airy & spacious, balanced by a modern open floorplan (perfect for hosting). Hardwood flooring flows throughout, framed by large windows & high ceilings. The MOSTLY BRAND NEW gourmet chefs kitchen is fitted w/ all the latest top-of-the-line appliances + a center island, marble counter-tops & more. Recessed lighting can be found throughout. Comfortable lodgings include a primary w/ a luxurious bath & huge walk-in closet, as well as a separate room & bathroom downstairs for guests. Downstairs area includes a rec room / home gym, entertainment room, guest suite, etc. The backyard is as immaculate as the inside & totally private w/ a verdant lush lawn, sparkling pool, 1br 1ba guest cottage w/ full kitchen, wrap around gardens & more!

A stunning forested retreat of the highest caliber nestled in an exclusive Hillsborough neighborhood in walking distance to Burlingame Country Club. Enveloped by redwoods and on 1.8+ acres, the homes massive back porch and front entertaining patio with pool both take advantage of the wooded surroundings. Generous living spaces boast pristine hardwood floors, vaulted ceilings & large picture windows with views. French doors throughout devise a tremendous indoor/outdoor experience. Whip up a feast in the luxurious eat-in Chefs Kitchen with Wolf range and 48 Sub-Zero, dining in the adjoining dining room with elegant coffered ceiling & wainscoting. Retire to the gracious study with a wall of built-in oak shelves and fireplace or to the expansive Primary Suite with double walk-in closets, soaking tub and fireplace. Downstairs, a fitness room, laundry & au pair unit access the backyards many winding paths. 3-car garage is at the end of the gated drive. Be captivated by this secluded gem.

THE MODERN VANGUARD: Elite New Construction Re-Defines Scenic Luxury. Dazzling with design innovations, this modern marvel evokes the glamour of the Hollywood Hills, where luxe retreats embrace nature. Award-winning architect Leonard Ng harnesses his Harvard and MIT background into a bold statement over 7,700 ft. of brand new ingenuity. Bay-View North Hillsborough promontory comes to life amidst a composition of stone, glass, & wood. Walls of glass, huge open volume, interplays of light & geometry. Minimalism soothes & soars, as clean lines reach upward & outward. 2-Story Living Room a work of art with 20 ft. ceilings, vertex angles frame Bay & Mt. Diablo. *2-Story Lobby of 22 ft. glass ceiling, floating staircase, & mezzanine. *50 ft. wide Tour de Force Kitchen/Fam Great Room of 11.5 ft. ceilings opens to Infinity Pool *Channeling Hollywoods Bird Streets, a masterpiece of 5 or 6 beds, 7.5 baths, plus flex for Gym, Office or Au Pair, along with Home Theater, Wine Cellar, & 3-Car.

1305 Tartan Trail showcases a wonderful opportunity to get in to Hillsborough! Lovingly maintained throughout the years and ready for a new vision. Most of the living space is on the main level which includes the living room, dining room, kitchen, family room, 3 beds and 2 baths. Downstairs you will find the 4th bedroom, office, 3rd bathroom, laundry and entrance to and from the attached 2 car garage. The .51 acre lot boasts multiple layers ready for you to explore with a level grass area off of the dining room perfect for playtime, an expansive deck accessed from the family room, lots of beautiful trees and greenery, freshly planted flower garden and a lower patio from the 4th bedroom. Rounding out this wonderful opportunity is the location with great local schools, easy access to 280 and being near shopping at Crystal Springs Plaza all while surrounded by nature providing a feeling of serenity.

First time on the market, updated custom built 2890 sq ft ranch style home on a 26,898 sq ft lot. Three large bedrooms, two full bathrooms and two half bathrooms. Formal living room and dining room. Family room with views to the beautiful yard with pool. Large Kitchen with breakfast nook. Laundry/storage room next to the kitchen. Three car garage with two outdoor parking spaces. Large, mature landscaped yard with Pool and small pool house. Private yard/sitting area off of master suite. The excellent floorplan invites casual living or formal entertaining. Easy access to highway 280.

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.

Perfectly positioned in a premier location, this residence exudes chic sophistication and modern refinement. Elegantly wrapped in privacy and boasting approximately 5,840 square feet of luxury living, this one-of-a-kind spectacular home combines architectural integrity and quality materials. Designed by internationally acclaimed architect Farro Essalat, this exceptional residence, is built with uncompromising quality and meticulous craftsmanship. Elegant gathering spaces make this home an entertainers dream, with most rooms opening to the beautiful surrounding outdoors. Outside, the resort-like grounds feature an entry courtyard, pool and spa, sweeping wrap-around terrace, pool house with kitchen and full bath, a drought-friendly expansive level lawn, and an attached 4-car garage. Plus, it's just moments to downtown conveniences and minutes to SFO and commute routes to all of the Bay Area and Silicon Valley.

Situated in premier lower North Hillsborough, this sprawling single-level, ranch-style home sits on a level .47-acre lot in a truly idyllic setting. The elegantly understated residence of over 2,700s.f. features 3 bedrooms, 2.5 baths, expansive formal rooms with oversized picture-frame windows that overlook the amazing grounds, a chef's kitchen with center island & breakfast room, and an adjoining family room with sliding glass doors that opens to the stunning rear yard. 3 sizeable bedrooms, including the primary suite with dressing area with makeup vanity, and spa-like bathroom are located on one side of the home, while the opposite side comprises a powder bath and huge laundry/mud room. The expansive grounds with level lawns, lush and mature landscaping, pool with spa, and huge entertaining patio with pergola, offer the best of indoor/outdoor living. An attached 3-car garage, top-rated schools, and close proximity to Burlingame Avenue add to the appeal of this exceptional property.

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!

HOME AS CANVAS" ICONIC MODERN ESTATE IS A RESIDENTIAL WORK OF ART. At the very heart of Lower South Hillsborough, discover one of the Town's most dramatic architectural homes. *Very Attractive Seller financing may be available to qualified buyer.* An iconic modern estate of towering ceilings, grand entertaining realms, & flat lot of .78 Acre, all awaiting your interpretation of the modern genre. Imagine your own palette & connoisseur's interior design. 6 beds, 6.5 baths, Office, Gym, Screening Room, Recreation Room, Indoor/Outdoor Loggia, 4-Car Garage + carport. Just steps to South School, these are special lands of historic importance, near the Hillsborough Racquet Club, subdivided by the Homs Family in the late 70s/early 80s. *Bespoke architecture that designers dream of: 10 ft. Ceilings on main level, volume & light, indoor/outdoor flow with a flat lot * 2-story Grand Salon with ceilings over 23 feet.* Creative potential, imagine a new ADU on 100% Usable gated grounds!

Extensively remodeled with absolute designer sophistication, this is luxury living with classic California elegance. Nearly every inch has been reimagined with chic designer flair and a reconfigured floor plan that works perfectly for todays lifestyle. The entire home is bright and flowing with wraparound walls of glass and towering sky-lit ceilings. Living and dining areas are open, yet well-defined, and the all-new kitchen is a five-star masterpiece. High-end finishes, hardware, and fixtures with hand-made cabinetry and solid white oak floors. There are 4 bedrooms and 4.5 baths, including a sumptuous multi-room primary suite on the top level. Behind the scenes is all-new plumbing and electrical, 4-zone heating and air conditioning. Outside, the wraparound grounds include a sun-swept pool and spa, and a fire pit terrace. All of this, plus an incredible location in sought-after Lower Hillsborough with easy airport access as well as acclaimed schools.

Sprawling Ranch style home on over a half acre level lot offers abundant indoor and outdoor living space. This home has not been on the market in over 30 years and offers you the perfect opportunity to reimagine all this home has to offer. This home has been lovingly maintained and features a large formal living room, a spacious formal dining room, a very large family room as well as a large media room. The eat in kitchen overlooks the front yard that has a circular driveway. All 3 bedrooms are a generous size, including the primary suite that boasts a large bath with a dual vanity and stall shower. The expansive level yard features a swimming pool with a built in spa and a large level lawn area perfect for entertaining or play. There's also a side yard that has some mature fruit trees and is a blank slate to created your own vegetable or flower garden. This home also has a laundry room, oversized linen closet, a 2 car garage and is conveniently located close to major commute routes

The bright, flowing indoor floorplan 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.

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.

Welcome to a stunning custom home nestled in the Lakeview community of beautiful Hillsborough. Completely rebuilt, this homes unique design with exquisite materials and features will captivate you. Step inside to be greeted with soaring ceilings, arched doorways, and enchanting chandeliers. Chefs kitchen features gorgeous quartz counters, a 9 island, professional Viking stainless appliances, including an 8-burner gas range & built-in cappuccino maker. Home includes large office; 5 bedrooms including 3 en-suites for primary, guest and au pair on lower level, and family room with exterior entrance. Details include beautiful walnut floors, tray ceilings with large molding, 8 doors, custom casement windows. Accordion doors open to an entertainers paradise: including built-in fireplace, oversized outdoor kitchen, custom wine cellar, jacuzzi & pool all overlooking a 5-pin putting green & lush landscape. Simply put: an exceptional custom home offering unique design for luxurious living.

Mediterranean home on extensive, gated corner lot. Freshly painted interior and new engineered hardwood flooring throughout. The kitchen features high-end stainless-steel appliances brand new oven, stove, & dishwasher. Separate outdoor deck and patio areas for entertaining. Property includes dedicated office, recreation room, fitness center, and customized wine cellar. Highly desired location in-between San Francisco and Silicon Valley.