Hillsborough CA Real Estate & Homes for Sale

Tucked in one of South Hillsborough's most coveted enclaves, this private gated estate blends timeless design with fresh, modern updates across an expansive floor plan. A grand motor court and curated landscaping with mature trees and hundreds of new plantings set an impressive tone on arrival. Inside, the heart of the home features an architectural chef's kitchen and great room with soaring ceilings and walls of glass that open to the outdoors. Formal living and dining rooms create an elegant setting for entertaining, while a stunning office with floor-to-ceiling windows provides the perfect workspace. Five luxurious en-suite bedrooms and seven-and-a-half beautifully designed bathrooms with spa-like amenities like a soaking tub and a steam shower. Additional highlights include four fireplaces inside the home, dual laundry rooms, a versatile media room and gym, and modern upgrades such as new electrical systems, EV charging, and dual HVAC. Outside, the resort-style grounds offer a pool, jacuzzi and cabana, water features, an outdoor kitchen, and an outdoor patio fireplace. Located close to top schools, downtown Burlingame, and easy commuter routes, this exceptional property delivers both everyday comfort and extraordinary style.

Sophisticated and beautifully updated, 130 Stonehedge Road offers elegant single-level living in one of Hillsboroughs most desirable enclaves. A formal entry leads to a sun-filled living room with expansive picture windows framing views of the lush grounds. The stunning chefs kitchen features premium appliances, a generous island, and custom cabinetry, connecting seamlessly to the casual living room and the formal dining room for effortless daily living and entertaining. A wide hallway leads to four well-placed bedrooms, including a serene primary suite with a spacious walk-in closet and a spa-inspired bathroom with dual vanities, soaking tub, and separate shower. Additional bedrooms enjoy excellent natural light and access to beautifully finished bathrooms. A versatile bonus room offers ideal space for an office, gym, or studio, complemented by a well-equipped laundry room and a three-car garage. The backyard evokes a private retreat with a large entertaining deck overlooking an expansive level lawn bordered by mature trees and fresh landscaping perfect for gatherings, play, and relaxation. Located just minutes from Burlingame, top-rated public and private schools, local country clubs, and convenient commuter routes to San Francisco and Silicon Valley.

*NOT AVAILABLE TO SHOW YET - TENANTS IN PROCESS OF MOVING - WILL BE ABLE TO SHOW SOON* THIS TROPHY HOME IS A ONE-OF-A-KIND MODERNIZED SMART-HOME MANSION! THE IMPOSSIBLE WAS DONE W/ THESE MULTI-MILLION DOLLAR RENOVATIONS! This magnificent estate perfectly integrates timeless architecture with a modern interior, with all top-of-the-line amenities. An estate fit for royalty! Interior with 100s of recessed smart lighting, smart thermostats with multi-zone air conditioning, motorized hunter Douglas, & Sonos speakers throughout; all controlled via smart phone. BRAND NEW & MODERNIZED KITCHEN & 8.5 NEW BATHROOMS. Features include 8 new HVACs, majestic stained-glass windows, artisan stone grand fireplaces, high ceilings, elegant living room, multiple en-suites, maids quarters with a full kitchen, separate entrances, all windows w/ an extra layer of glass, guest parking for 30+, etc. *JUST INSTALLED A NEW POWERFUL GENERATOR FOR THE ENTIRE HOUSE! NO NEED TO WORRY ABOUT PG&E & ANY POWER OUTAGE. PLUS 2 NEW 50 AMPS PLUG READY FOR YOUR ELECTRICAL CHARGER*. Plus enjoy the ability to be able to walk to downtown and get access to some of Northern California's best schools. THIS IS THE BEST OF THE BEST!

Perched in the prestigious Lakeview neighborhood of Hillsborough, this gated residence blends refined living with breathtaking design and panoramic views. A spacious motor court and two-car garage welcome you to a home of distinction. Step into the elegant foyer, where classic columns frame a soaring open-concept living area. Vaulted ceilings with exposed beams and floor-to-ceiling windows flood the space with natural light and showcase sweeping vistas. The expansive living room features a dramatic stone fireplace and flows into a chefs kitchen with high-end stainless steel appliances, tray ceiling, and a generous breakfast barperfect for everyday living and entertaining. This four-bedroom home includes a luxurious primary suite with a private sitting area and spa-inspired bath, complete with soaking tub, frameless glass shower, and double vanity. Located in the serene Lakeview area near top-rated schools, boutique shopping, and dining, with easy access to Hwy 280, 101, SF, Silicon Valley, and SFO. The land has potential for subdivision, subject to city approval.

A rare opportunity. Located in the coveted lower-Hillsborough Ryan Tract Neighbourhood. 1735 Crockett Lane is an ideal home for entertaining! The home is located on a quiet cul-de-sac. The common area includes a family room, breakfast nook, formal dining room, and formal living room area. This one story 4-bedroom 3 bath home is expansive and private. Plenty of storage space. Located on a private lot with a generally flat backyard on a desirable cul-de-sac street. High ranked school district. North School, Crocker Middle School, and Burlingame High School. Located near Downtown Burlingame with plenty of stores and restaurants. There are an additional bedroom and bathroom located on the opposite side of the common area. Over the years this has been used as a bedroom or office, but it is ideal for a possible au-pair suite or in law suite. Possibility to expand home to 4500 SqFt and add an additional dwelling unit (ADU). Buyer to verify all information prior to close of escrow and removal of all contingencies.

ONE OF HILLSBOROUGH'S BEST DEALS, SERIOUSLY! Set on an oversized lot of nearly 1 acre, this single-story home was recently remodeled with sleek contemporary designs and modern amenities. The open layout seamlessly connects the living room and high-end chefs kitchen, ideal for entertaining. Enjoy spa-like bathrooms, a luxurious master suite, a versatile bonus room downstairs, recessed lighting, tasteful flooring, coffered ceilings, and stone fireplaces as striking centerpieces. An integrated Sonos sound system complements the expansive indoor-outdoor flow, with a huge flat backyard offering bay views and endless potential for expansion, an ADU, or additional deck space well beyond the back fence. Complete with a 3-car garage, access to top-rated schools, and easy commuting via Highway 280, all just minutes from downtown Burlingame. This home offers it all, YOU HAVE TO SEE IT TO EXPERIENCE JUST HOW GREAT IT IS!

A BREATHTAKING TROPHY ESTATE BLENDING TIMELESS ELEGANCE WITH RESORT-STYLE LIVING. This architectural masterpiece offers an extraordinary layout designed for both grand entertaining & intimate daily life. Sweeping driveway & motor court lead to 2 garages with car lifts ideal for collectors. The outdoor retreat features an infinity-edge pool, spa, expansive pool deck w/ designer pergola, full outdoor kitchen & BBQ, tennis court, guest house, bocce court, rose garden & a dedicated childrens play area. Inside, a dramatic foyer opens to soaring ceilings, a formal living room bathed in natural light, a grand dining room, chefs kitchen w/ breakfast nook & spacious family room. A luxe billiard room w/ wine bar, elegant sitting room, private office & guest suite complete the main level. Upstairs, the primary suite stuns w/ romantic fireplace, spa-inspired bath & oversized walk-in closet. 3 addl ensuite bedrooms & attic storage offer comfort & flexibility. The lower level is a true entertainers dream featuring a cinema-quality home theater, game room & kitchenette. This residence delivers unmatched elegance, scale & lifestyle in one of the Bay Areas most prestigious settings.

This beautifully designed 5-bedroom, 5 full and 2 half-bath home blends timeless sophistication with modern comfort in one of Hillsboroughs most sought-after neighborhoods. A grand two-story foyer welcomes you in, leading to formal living and dining rooms perfect for entertaining. A private guest suite on the main level adds flexibility, while a butlers pantry hallway and separate walk-in pantry provide smart, functional storage. The expansive great room unites the family area, breakfast nook, and chefs kitchen, opening through folding glass doors to a spacious deck with a tranquil fountain and outdoor fireplaceideal for indoor-outdoor living. Downstairs, a media room with wet bar, temperature-controlled wine cellar, full bath, and additional bedroom offer space to relax and unwind. Upstairs, the luxurious primary suite features a sitting area, two walk-in closets, and a sunlit balcony. Two additional en-suite bedrooms and a handsome wood-paneled office complete the home. Premium finishes include motorized Hunter Douglas blinds and outdoor privacy screens and a full Savant Smart Home System for effortless control of lighting, climate, media, and music.

Experience the perfect blend of luxury, elegance & California living in this breathtaking Mediterranean estate. This residence offers unparalleled privacy & sweeping views of the San Francisco Bay & surrounding mountains. A long, gated driveway welcomes you setting the stage for the home's elegant interior. Step inside to a dramatic, light-filled foyer featuring a graceful winding staircase that leads into an expansive living room framed by floor-to-ceiling windows showcasing the spectacular views.The gourmet chef's kitchen is comes complete with a large center island, elegant stone countertops, & top-of-the-line Viking stainless steel appliances. A richly wood-paneled library/office & spacious formal living & dining areas add sophistication, while new double-pane windows enhance comfort & energy efficiency throughout the home.Upstairs a primary suite awaits, featuring a spa-inspired bath with a jetted soaking tub, alongside generously sized bedrooms offering comfort & privacy. The impeccably landscaped grounds create a true oasis, featuring a resort-style pool & spa, & private tennis court. Perfect for both relaxation & entertaining, this property offers an unmatched lifestyle in one of California's most coveted settings.

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 offers 4 bedrooms and 4 bathrooms, with the added bonus of a brand new ADU that includes a 5th bedroom and additional bath. Inside, discover 16-foot ceilings, stunning wood floors, abundant natural light, and premium upgrades throughout. The chef's kitchen features Thermador appliances and an 11-foot island, with La Cantina doors creating seamless indoor-outdoor flow. Outside, your private oasis awaitswith a beautiful pool, bocce ball court, and plenty of room to relax or entertain. The 775 sq ft ADU is versatile and perfect for guests, a home office, or extended family. This property perfectly blends modern living, luxury, and space in the sought-after Carolands neighborhood. Welcome home!

LOWER HILLSBOROUGH'S PREMIER ESTATE! LUXURY, DESIGN, & PRIVACY! Rare listing, a once-in-a-lifetime property w/ one of the LARGEST LOTS in its area -- 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. Detached 5-car garage with a 1br/1ba ADU and private executive office / conference room. Amenities 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, retrofitting, & exterior lighting have all been upgraded modernizing this estate. 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, butlers pantry, garden room, music room, whole house 22kW generator, smart electronic lighting, elevator, roof deck, multiple en-suites, & MORE! Too much to list here!

Set on a generous and private 0.69-acre lot with breathtaking views, this lovely updated 4-bedroom, 2.5-bath home offers the perfect blend of modern comfort and timeless elegance. Designed for today's lifestyle, it features light-filled interior spaces and a seamless flow ideal for entertaining. Highlights include chic flooring, tray ceilings, recessed lighting, and expansive picture windows framing the lush, natural surroundings. The open-concept dining area, complete with a fireplace, is accented by French doors that open to a sizable patio and level lawn, perfect for indoor-outdoor living. The chef's kitchen boasts a center island and top-of-the-line appliances, flowing effortlessly into a spacious great room with direct access to a large deck showcasing spectacular views. 3 bedrooms and 2.5 baths are conveniently located on the main level, including a luxurious primary suite with a large walk-in closet and a spa-inspired bath. A 4th bedroom is located on the lower level, offering flexibility for guests, a home office, or additional living space. A long, sweeping driveway bordered by manicured boxwood hedges, vibrant rose bushes, and elegant Japanese maples leads to a 2-car garage with additional storage, completing the appeal of this exceptional, turnkey property.

A symphony of modern architecture and refined design, 855 Darrell Road is a one-of-a-kind contemporary estate where form meets function in the most breathtaking way. Crafted by Kelland Architects and built by Thorenfeldt Construction, every inch of this 7,370-square-foot residence pulses with innovation, artistry, and intention. From the moment you step inside, youre greeted by soaring ceilings, curated finishes, and dramatic Bay views framed by walls of glass. Five luxurious en suite bedrooms are tucked across three stunning levelseach an immersive experience in elevated living. The kitchen, a true showpiece, features custom walnut cabinetry, bold tile by Moses Hacmon, and a suite of chef-worthy appliances. Outside, a glass-railed deck and covered entertaining patio offer seamless indoor-outdoor flow, while the spa-inspired lower level, yoga studio, and smart-home systems redefine what it means to live well. Discover a modern marvel designed to captivate, inspire, and endure.

RARE FIND! Don't miss this once-in-a-lifetime opportunity to live on one of Hillsborough's most prestigious streets. Nestled on a nearly 3/4-acre lot at the end of a peaceful cul-de-sac, this property offers the perfect blend of privacy and convenience. Just a 5-minute drive brings you to the vibrant shops and restaurants of Broadway or downtown Burlingame. Commuters will appreciate the quick access to the 101 Freeway, less than 2 miles away, making it easy to reach both San Francisco and Silicon Valley. For frequent flyers, San Francisco International Airport is only 15 minutes away. This gated estate provides access to top-rated schools and features a long driveway leading to a spacious motor court. The grounds include a sparkling pool, spa, and a charming pool house--ideal for relaxing or entertaining.

Nestled in Hillsborough's prestigious Ryan Tract, this exceptional residence blends privacy, convenience, & charm. Just minutes from Downtown Burlingame & Broadway, it offers easy access to Highway 101 and top-rated schools. A welcoming front porch leads into a bright & airy interior w/ hardwood floors, recessed LED lighting, and expansive windows. The elegant dining room features a bow window & connects to the updated eat-in kitchen w/ granite countertops, a glass tile backsplash, high-end appliances, & a breakfast nook. The living room centers around a striking fireplace flanked by French doors & a picture window. A refined study offers built-in shelving, a fireplace, a wet bar, & backyard access. The primary suite includes custom built-ins, fireplace, French doors to a private deck, & a spa-like bath with a jetted tub, a walk-in shower w/ a functioning steam bath unit, & a walk-in closet. Upstairs, a versatile art studio opens to a private balcony. 2 additional en-suite bedrooms & a powder room complete the home. The beautifully landscaped backyard features a large patio w/ a fireplace, a lush garden, & an expansive lawn. A paver motor court & discreet garage enhance curb appeal. 680 Fairway Circle is a rare opportunity in one of Hillsborough's most sought-after neighborhoods.

GREAT NEW PRICE! PREMIUM QUALITY THAT COULDN'T BE REPRODUCED AT THIS NUMBER! Casa Serena dazzles with authentic quality and the romance of Riviera retreats, yet delivers its new owner a platform of thoroughly modern livability. The estate you see today was meticulously re-imagined, expanded, and re-built to the highest standards. Spanning 5,600 sq. ft., you are invited to marvel at the "composition within the composition." Top flight luxury designer elements of Venetian plaster walls, vaulted ceilings of 14-15 feet, European tilework, mahogany doors, and made to order light fixtures by Steven Handelman. Wolf, SubZero, Miele. With unabashed inspiration from the great homes of Southern California, where the Spanish Colonial Revival celebrates its indoor/outdoor joie de vivre, this estate lavishes in sun from south and east. More than a house, this is an experience, a lifestyle, a feeling. Like a timeless book or a classic wine, this is an experience to become immersed within. *4 beds, 4 baths, plus incredible lower level apartment of 1500 feet with kitchen, recreation room, gym (or possible 5th bedroom) pro wine cellar, and mud room *World class detail *Resort caliber pool, spa, flat lawn, orchard *Spectacular Primary Suite View Terrace *Huge 3-car * Arch Digest throughout! *

Situated on a private side street, this grand estate sits on a majestic 2-acres with jaw-dropping panoramic bay views, some of the best in all of Hillsborough. Exquisite architectural detailing and finishes throughout, including inlaid parquet walnut floors, hand carved fireplaces, and walls of glass framing iconic bay views and landscaping. The main level includes a stunning office, billiard hall, and the "Morocco Room" lounge. Upstairs, the large master suite enjoys equally stunning views of the bay, in addition to a luxury spa bath and formal sitting room. A separate in-law suite and wine cellar with tasting room are located on the lower level of the residence. Equally impressive are the surrounding grounds, fully landscaped with grand-scale trees, expanses of manicured lawn, and an elevated terrace overlooking the views and swimming pool. All of this just minutes from shopping, dining, golfing, parks, and top rated Hillsborough schools. (Square Footage Per County Records: 8,629)