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$39,888,000
8 Beds ⋅ 13 Baths ⋅ ML82036796 MLS
Sitting on a commanding 2.5 acres atop a Hillsborough promontory with panoramic views, this bespoke estate reflects the vision of MAK Studios authority in modern design. Defined by a sculptural stone, glass and wood facade and a dramatic 22-foot high entry that frames the horizon, this home has 8BR's and options for 2 offices. The culinary program is exceptional: a statement kitchen appointed with Gaggenau appliances and supported by a fully equipped staff dirty kitchen for seamless entertaining at scale. The primary suite is conceived as a five-star retreat, enveloped in full slab marble with a steam shower and integrated smart amenities. Leisure and lifestyle spaces rival those of a private club multiple grand lounges, a state-of-the-art theater, executive office, fitness studio, bar, golf simulator, and a 1,620-bottle wine cellar. Advanced Crestron automation orchestrates lighting, climate, window treatments, and security, while radiant heat, owned solar, tankless systems, and a standby generator ensure efficiency and resilience. Resort-level grounds unfold with a 50-foot pool and spa, fire-lit terraces, manicured lawn, putting green, expansive motor court, and dual two-car garages a rare convergence of design, scale, and setting in Hillsborough.

455 Pinehill RD, Hillsborough

Listed by Phil Chen, 415-271-1920 from Christie's International Real Estate Sereno
(If provided) CoList: from

$9,280,000
5 Beds ⋅ 5 Baths ⋅ ML82036409 MLS
Welcome home to your modern farmhouse in the coveted Carolands neighborhood of Hillsborough. Situated on a flat and usable .52-acre lot, this home was rebuilt and expanded in 2021 from the foundation up, ensuring a turnkey and comfortable living experience. The main house boasts 4 bedrooms and 4 bathrooms, plus a 1-bedroom, 1-bath ADU. 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 to your outdoor oasis that includes a new pool/spa, BBQ, bocce ball, expansive lawn, and fruit trees. There is also a large side yard perfect for basketball, extra cars, or even a boat. This property combines rare single-level living with modern features, great natural light on a flat, usable lot, and a neighborhood that invites walks and bike rides.

588 Craig RD, Hillsborough

Listed by Phil Chen, 415-271-1920 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Amy Xiao from KWCU
$5,725,000
4 Beds ⋅ 4 Baths ⋅ ML82033948 MLS
Beautifully reimagined single-level home in coveted Lower Hillsborough. This 4-bedroom, 3.5-bath residence offers a thoughtfully updated layout, anchored by a newly redone open kitchen and family room designed for modern living and effortless connection. The interiors feature all-new flooring, custom cabinetry, and a chefs kitchen appointed with Miele appliances, including an induction cooktop and built-in espresso machine. Expansive new windows and sliding doors fill the home with natural light, complemented by new recessed lighting throughout. Additional highlights include a refreshed fireplace, a stylish wet bar, and a brand-new garage door. Outside, the property has been enhanced with a new metal roof, freshly landscaped grounds, and a new concrete patio, ideal for entertaining or relaxing in the private backyard, with ample space to add a pool and ADU. Tucked away on a private street just minutes from top-rated schools, parks, and downtown conveniences, this turnkey residence is ready for its next chapter.

340 Arden RD, Hillsborough

Listed by Phil Chen, 415-271-1920 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Phil Chen from SGP
$12,500,000
8 Beds ⋅ 8 Baths ⋅ ML82032610 MLS
Striking modern estate offering the perfect blend of luxury, scale, and design. This full scale renovation showcases soaring ceilings, dramatic floor-to-ceiling windows, and seamless indoor-outdoor living. The spacious floor plan features grand formal and casual living areas, a sleek chefs kitchen, and walls of glass opening to expansive terraces with serene tree-lined views. Luxury amenities include a private home theatre, gym, tasting room and wine cellar, elevator, and a resort-style backyard with pool house and built-in BBQ. The sparkling pool with water features, multiple lounge areas, and expansive patio create the ultimate setting for entertaining and relaxation.

1215 La Cumbre, Hillsborough

Listed by Jenn Gilson, 650-642-6957 from Golden Gate Sotheby's International Realty
(If provided) CoList: Kia Amini from Compass

Sold listing courtesy of Jenny MacLeod from APR
$10,200,000
8 Beds ⋅ 7 Baths ⋅ ML82032410 MLS
Welcome to 45 Calaveras Court, a brand-new modern masterpiece nestled in the Hillsborough hills. Located at the end of a private cul-de-sac on a sizable 4-acre lot, this stunning residence offers approximately 7,000 square feet of elegantly designed living space. Enjoy unobstructed canyon views from every window, providing a breathtaking backdrop to your everyday life. Step inside to discover soaring ceilings that create an open and inviting atmosphere, complemented by an abundance of natural light that fills every corner. The expansive first floor features a massive entertainment deck, perfect for hosting gatherings or simply relaxing amidst nature. With a total of 8 bedrooms, including master suites on each level, this exceptional home is perfect for large families or multi-generation living.

45 Calaveras CT, Hillsborough

Listed by Pierre & Alex Buljan, 650-400-1188 from Compass
(If provided) CoList: from

Sold listing courtesy of Greg Browman from 7A895
$7,780,000
5 Beds ⋅ 7 Baths ⋅ ML82027382 MLS
Built in 2021, this showstopping modern estate captures the essence of California living. Soaring ceilings and walls of glass open completely to reveal breathtaking hillside and Bay views, blurring the line between indoors and out. The designer kitchen stuns with custom rift-oak cabinetry, marble island, and top-tier appliances. An entertainers dream, the outdoor terrace features a built-in BBQ, spa, fire pit, and endless views. Smart home technology, solar power, and a premier Hillsborough location complete this rare modern masterpiece.

60 Glengarry WAY, Hillsborough

Listed by Victoria Yang Surles, 415-818-3603 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jennifer Griessel from CCPCR1
$10,750,000
8 Beds ⋅ 10 Baths ⋅ ML82021334 MLS
BRAND NEW ECO-FRIENDLY MODERN HOME WITH PANORAMIC BAY VIEWS. DESIGNED FOR ENTERTAINING, THIS 7160SF HOME FEATURES 8 BEDROOMS, 8 FULL AND 2 HALF BATHS, SEPARATE ADU WITH 2 BEDROOMS AND SEPARATE PARKING, OPEN CONCEPT DESIGN WITH NUMEROUS LUXURY FEATURES INCLUDING, 4K MOVIE THEATRE, GAME ROOM, SAUNA, GLASS ENCLOSED WINE CELLAR, AND LARGE INFINITY POOL AND SPA. THE CHEF'S KITCHEN SHOWCASES MIELE APPLIANCES, CLEAF WHITE OAK CABINETS, TAJ MAHAL HONED COUNTERTOPS, AND SEPARATE BUTLER'S PANTRY. THE EXPANSIVE PRIMARY SUITE HAS A COZY FIREPLACE, EXPANSIVE VIEWS, VIEWING PATIO, LARGE WALK-IN CLOSET AND HIS/HERS WATER CLOSETS. ENHANCED BUILT-IN TECHNOLOGY INCLUDES AN UBIQUITI WIFI SYSTEM, SECURITY CAMERAS, ELEVATOR, WHOLE HOUSE AIR AND MOISTURE FILTRATION SYSTEM, SOLAR PANELS AND LUTRON LIGHTING. DESIGNED BY SAFAEI DESIGN GROUP, THIS HILLSBOROUGH ESTATE IS DESIGNED FOR ENTERTAINMENT AND RELAXATION!

1221 Kenilworth RD, Hillsborough

Listed by Nick Corcoleotes, 650-207-2758 from Coldwell Banker Realty
(If provided) CoList: Sara Masoudnia from Bast Properties, Inc.

Sold listing courtesy of Jane Konovalova from JETS
$12,600,000
5 Beds ⋅ 5 Baths ⋅ ML82021202 MLS
HILLSBOROUGH'S MOST EXCITING NEW CONSTRUCTION! Brand New Designer Showcase Overlooking the Bay near Nueva School. Dream Team of design and craftsmanship: award-winning San Francisco designer Studio Michael Hilal infuses cutting-edge modern DNA with warmth, livability, and a symphony of handpicked accoutrements. Custom builder Nejasmich Developments delivers renowned detail and artistry to a sleek canvas by Sausalito architect Brooks McDonald. The INNOVATION begins with a one-story building envelope. This platform sets the stage for ceilings over 12 feet, and 360 DEGREES OF LUXURY, with dynamic flow to usable flat lands at both front & rear. SEAMLESS is a most fitting theme for this lifestyle. Minimize the boundaries of indoors & outdoors, seamless attention to clean lines & finishes harmonizes as organic ambiance. | European Luxe meets Eastern Minimalism| Showstopper Great Room | Bay-View Party Terrace off Dining Room | 4 beds, 3.5 baths, plus Office, + Family Den in main home | Deluxe ADU for sleeping quarters, kitchen/laundry | Pro quality Gym w/ morning bar, German Sauna, backlit mirrors | Decadent Wine Pantry | Premium millwork of white oak & walnut, curated designer lighting | 3 Steam Showers | Pewter-Flamed Limestone hardscape | Gated Entry | Fire Pit | Outdoor Grilling Hub

55 Del Monte DR, Hillsborough

Listed by Geoffrey Nelson, 650-455-3735 from Coldwell Banker Realty
(If provided) CoList: Mike Bohnert from Coldwell Banker Realty

Sold listing courtesy of Kristopher Mares from KWPEN
$4,760,000
3 Beds ⋅ 4 Baths ⋅ ML82005190 MLS
Tucked beneath a canopy of majestic redwoods, this stylish single-level home blends timeless design with effortless indoor-outdoor living, and sits on one of Hillsborough's most coveted streets in Lower South Hillsborough. Fully reimagined in 2017, the residence offers 3 bedrooms, 3.5 bathrooms, and 2,352 square feet of thoughtfully designed space on a nature-filled lot in one of Hillsboroughs most desirable locations. Every room connects seamlessly to the outdoorswhether its the serene backyard retreat off the primary suite or the barbecue-ready dining area just off the kitchen. The open-concept layout is anchored by a chic modern kitchen that flows into two inviting living areas, one with a cozy fireplace perfect for quiet evenings or casual entertaining. Moments from both Downtown Burlingame and Downtown San Mateo, this home offers the perfect balance of tranquility and convenience.

244 Roblar AVE, Hillsborough

Listed by The Laugesen Team, 650-465-5742 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of The Laugesen Team from KWPEN
$8,650,000
7 Beds ⋅ 9 Baths ⋅ ML81993380 MLS
Perched atop a serene cul-de-sac in Hillsborough, this architecturally striking modern estate offers breathtaking, unobstructed views of the SF Bay. Built in 2020, this 7 bedroom and 9 baths home blends cutting-edge parametric design with luxurious functionality, creating a seamless flow between indoor and outdoor living. The main residence features 5 beds, 4 full baths, and 2 half baths, thoughtfully designed with high-end finishes and an open-concept layout that maximizes natural light and panoramic vistas. Floor-to-ceiling windows, sleek contemporary lines, and premium materials define the sophisticated ambiance. A separate ADU with its own private entrance adds versatility, offering 2 bedrooms, 2.5 baths, and a stylish, self-contained living space ideal for guests, extended family, or rental income. Nestled in a private and tranquil court, yet just minutes from downtown San Mateo and Burlingame, this home offers the perfect balance of seclusion and convenience. Enjoy an easy commute to major highways, and access to top-rated Hillsborough schools, making this an exceptional opportunity for those seeking both luxury and lifestyle. Approved plans available for a raised infinity edge pool and 500sqft gym. A rare find in one of the Bay Areas most prestigious communities.

30 Melrose Court, Hillsborough

Listed by Vahid Firouzdor, 650-727-4554 from Compass
(If provided) CoList: from

Sold listing courtesy of Jane Konovalova from JETS
$7,100,000
6 Beds ⋅ 7 Baths ⋅ ML81950505 MLS
Discover unparalleled value in this meticulously crafted luxury new construction at 1175 San Raymundo in Hillsborough, California. Completed in 2023, this remarkable residence offers a grand living experience with expansive proportions and top-tier finishes, spanning over 5200 square feet. Thoughtfully designed for modern living, it features two family rooms, a spacious open living-dining area with a chef's kitchen, six bedrooms, seven bathrooms, and an additional flex room, striking the perfect balance of relaxation and privacy. Bifolding windows throughout enhance the seamless indoor-outdoor integration, defining the home's character. Complemented by thoughtfully designed decks and terraces, these spaces cater to entertainment and breathtaking views, providing an idyllic setting for gatherings or unwinding in the fresh air. This modern gem prioritizes quality, boasting top-tier materials and impeccable finishes, creating an ambiance of sophistication. The intelligently designed floor plan seamlessly connects open-concept living areas for a lifestyle of ease and comfort. Visit us to see this home for yourself, it won't last!

1175 San Raymundo RD, Hillsborough

Listed by Paul Zinchik, 415-297-1300 from Compass
(If provided) CoList: Eugene Zinchik from Compass

Sold listing courtesy of Shaun Walter from CBR
$3,685,000
4 Beds ⋅ 3 Baths ⋅ ML81937974 MLS
From the iconic low-pitched roof, the fabulous orange front doors, to the marvelous use of wood and stone accents, each detail in 1485 Southdown Road pays homage to the design sensibilities of the 1950s while elevating the classic Mid-Century Modern style. Embracing open concept living, the large gathering rooms encourage entertaining and connection. Invite friends to watch the shadows dance on the walls throughout the day as the sunlight floods the home. As the sun sets, enjoy the transformation into a cozy retreat where the windows become frames for the moon and stars high in the night sky. Then retreat to one of four dreamy and spacious bedrooms. Built with meticulous craftsmanship, this home stands as a testament to durability, quality, and authenticity while offering so many opportunities to expand the livability. Whatever your heart demands, there is room to make it happen. Situated on over half an acre, expansion and recreation possibilities abound + 6 car garage.

1485 Southdown RD, Hillsborough

Listed by Greg Damelio, 650-245-8700 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Jennifer Gilson from MCGR

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