Browse All Luxury Style Properties for Sale

4 Beds ⋅ 4 Baths ⋅ ML82046360 MLS

This stunning Chateau-style residence is gracefully situated on coveted Chateau Drive in the prestigious Carolands area of Hillsborough. Set on approximately .77 acres of gated grounds with Bay views, a circular driveway, and lush mature landscaping, this private estate is offered for the first time since its original construction. Spanning over 4,200 square feet, the home reflects timeless architecture, grand proportions, and light-filled interiors. A gracious entry opens to an expansive living room anchored by a marble fireplace, an adjoining library, and dramatic arched windows framing serene views. The elegant dining room with coffered ceilings and intricate hardwood floors is ideal for entertaining, while multiple covered verandas create seamless indoor-outdoor living. The home offers 4 bedrooms and 3.5 bathrooms, including a lower-level retreat with closet, fireplace, and patio access, well suited for guests, a private office, or extended living. Featuring a spacious family room, dry sauna, 3 fireplaces, dual laundry areas, and a 3-car garage w/ additional driveway parking. Mostly level grounds enhanced with fruit trees offer potential for a pool or ADU, creating a private estate-like setting. A rare offering in a premier sought after location.

555 Chateau DR, Hillsborough

Listed by Tim Allen Alevizos, 650-255-7635 from Remax Capital
(If provided) CoList: from

Sold listing courtesy of Shuo Xiang from XLB

$7,100,000

5 Beds ⋅ 4 Baths ⋅ ML82033175 MLS

EPIC HOMAGE TO CRAFTSMANSHIP AND LIFE IN THE SUN...One of Hillsborough's Most Elite Custom Remodels, steeped in the Magic of Montecito and Palm Beach. Every inch meticulously curated of high-end caliber inside and out. Ultimate privacy heightens soaring views above canyon, ridgelines, and sun-blessed luminosity. 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 of Santa Barbara. Wolf, Sub-Zero, Miele, exquisite custom cabinetry, & more. Indoor/Outdoor celebration as a personal resort with saltwater PebbleSheen pool, 3 waterfalls & raised spa. Flat grassy yards, barbecue cove, secret Napa garden of fruit orchard & irrigated veggie beds. The beauty of the floorplan includes 4 bedrooms on the main level, plus private lower level for 5th bedroom, huge media room & 2nd kitchen. This level is the perfect in-law apartment, teen hangout, or poolside media lounge. And shhhh, don't forget the world-class temp-controlled wine cellar as your own speakeasy! Prestige cul-de-sac location within minutes of Nueva & West Schools, & easy Hwy 280 connection to VC realm of Silicon Valley, plus AI, private equity, & biotech of South San Francisco and Financial District.

25 Searsville CT, Hillsborough

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

Sold listing courtesy of Chris Iverson from DP

$5,750,000

6 Beds ⋅ 7 Baths ⋅ ML82033179 MLS

A Hillsborough masterpiece: grand, expansive, & full of timeless Neoclassical charm with modern-traditional elegance, offering resort-style living in the coveted Skyfarm neighborhood. This prestigious estate welcomes you w/ a stately four-column façade, grand double doors, & dramatic foyer. Sun-filled formal living & dining rooms set the tone for entertaining, while the gourmet chefs kitchen features granite countertops, custom cabinetry, high-end appliances, & pass-through bar seating w/ direct backyard access. The family room impresses w/ exposed beam ceilings, wood-paneled walls, a wet bar, & floor-to-ceiling brick fireplace. Boasting 6 bedrooms, multiple en-suites, 2+ bonus rooms, abundant storage, & a lounge area w/ sink by the four-car garage, this home offers flexibility for family, guests, & work-from-home living. The primary suite includes a private balcony overlooking the backyard, pool, & tennis court, ready for resort living. Outdoor amenities include BBQ/lounge areas, mature trees, & a full-size tennis court, perfect for entertaining. Close to Downtown Burlingame, HWY 101, San Francisco, & Silicon Valley, this rare estate delivers prestige, privacy, & extraordinary living in one of Hillsboroughs most desirable neighborhoods.

746 Jacaranda CIR, Hillsborough

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: from

Sold listing courtesy of Stanley Lo from GRBA

$9,800,000

7 Beds ⋅ 8 Baths ⋅ ML82032512 MLS

Set behind private gates on a 0.645-acre parcel in Hillsborough's prestigious neighborhood, this 9,035 sq ft estate offers sweeping San Francisco Bay views & exceptional scale. A grand double-door entry opens to a dramatic foyer with a stained-glass dome skylight, leading to an expansive main level defined by floor-to-ceiling glass and abundant natural light. Custom coved & vaulted tray ceilings with architectural pillars enhance the living room, formal dining room, and family room, all unified by rich hardwood floors. Refined details include stained glass accents, skylights, crown molding, wainscoting, recessed lighting, and a multi-room audio system. The formal living and dining rooms feature fireplaces, with roof deck access ideal for entertaining. The family room includes a custom wet bar with wine cooler and built-ins. The chef's kitchen offers granite counters, center island, pantry, high-end appliances, and breakfast nook. The main level includes a paneled office, powder rooms, laundry, garage access, and a spacious primary suite. The lower level offers six additional bedrooms, staff quarters, wine cellars, a second kitchen, and access to a glass-enclosed indoor pool with spa. Expansive patios, synthetic lawn, walking paths, and motor court.

2930 Privet DR, Hillsborough

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: from

$11,000,000

5 Beds ⋅ 6 Baths ⋅ ML82014791 MLS

Experience timeless luxury at this grand Mediterranean estate, ~7,700 sqft total living space set on ~1.5 acres in the prestigious Tobin Clark area of Hillsborough. Showcasing panoramic views of the Bay and Peninsula. This exceptional property offers an unparalleled lifestyle of elegance, comfort, and privacy. The main residence features ~6,500 square feet of living space, including 5 ensuite bedrooms, each w/ access to a private terrace. A sweeping staircase, custom chandeliers, and soaring ceilings create a dramatic welcome, while the formal living and dining rooms, gourmet kitchen, & wine room provide elegant spaces for entertaining. The primary suite is a private retreat with a sitting area, custom walk-in closet, and spa-like bath. A separate 2 bed 2 bath guest house (~1,200 Sqft) includes its own kitchen, living area w/ fireplace, & private balcony and private garage, perfect for extended stays or multigenerational living. Outdoor amenities include an infinity-edge pool and spa, full-size tennis court, putting green, and multiple entertaining patios surrounded by mature landscaping. Located just minutes from top-rated Hillsborough schools, downtown Burlingame, SFO, and Silicon Valley, this is a rare opportunity to own one of Hillsborough's most iconic view properties.

171 Tobin Clark DR, Hillsborough

Listed by Wen Guo RE Group, 650-817-5000 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Chris Hylton from APR

$7,318,000

5 Beds ⋅ 6 Baths ⋅ ML82025896 MLS

THE BEST OF THE BEST IN HILLSBOROUGH. Award-Winning architectural design meets timeless farmhouse elegance. Previously featured in Modern Luxury Silicon Valley Magazine, this home was meticulously remodeled & redesigned in 2017 by both an award-winning designer & architect. A stunning blend of modern farmhouse designs and contemporary elements, this exceptional estate is crafted for stylish living and effortless entertaining. Eco-minded design and sustainable elements create a healthy, harmonious environment throughout. The expansive indoor-outdoor layout offers formal and informal living and dining areas, a grand kitchen with a Taj Mahal quartzite island that seats 12, plus 5 bedrooms, 5.5 spa-inspired bathrooms, a loft, office, and soaring vaulted beam ceilings. Enjoy multiple en-suites, sliding barn doors, large windows / glass doors, and a seamless kitchen/family room retreat. The resort-style grounds include a terraced garden, lush lawn, outdoor kitchen, fire-pit lounge, hot tub with natural rock waterfall, pool, sport court, & a spacious outdoor gym / pool house with full bath. Approved plans for an 800 sq. ft. ADU add even more opportunity. Moments to top-rated schools including Nueva, Crystal Springs Uplands, and other acclaimed schools. TOO MUCH TO LIST HERE.

1485 Oak Rim DR, Hillsborough

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: from

Sold listing courtesy of Mitch Wong from APR

$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

$6,800,000

5 Beds ⋅ 5 Baths ⋅ ML82002437 MLS

DESIGN FOR LIVING: THE PERFECT MEETING OF SUN, CELEBRATION, AND SAVOIR FAIRE! Remodeled designer quality unfolds across multiple destinations, with minimal boundary between indoor and outdoor living. 5 bedrooms, 3 full baths, 2 half baths, plus large Office (or gym), and enormous recreation room of 21 x 26 feet. Majority of the home flows on one level, including four bedrooms all together highlighted by a decadent expanded Primary Suite with 3 closets & marble bath. Tucked-away 5th bedroom suite also on main level perfect for guest or au pair. Myriad luxury details including a Craft Cocktail Bar, Wolf, Sub-Zero, high ceilings, integrated audio, outdoor kitchen, solar panels, Tesla power walls & more! Prestigious Jacaranda Circle backs up to Crocker Open Space, in the spirit of Woodside or Tahoe! Only 0.6 mile to Crocker Middle, 1.1 mile to Nueva School, 1.2 mile to West School, 1.9 mile to Apple Store on Downtown Burlingame Ave. The Primary Suite deserves its own paragraph. Expanded and remodeled, indulgent retreat with 3 customized closets plus built-in chest of drawers * Primary bedroom ceilings peak at nearly 12 feet. * Calistoga vibes opening out to pool and greenbelt vista. *Lighted Sport Court *Huge 3-car garage *Tons of western sunlight across pool and entire back of home*

748 Jacaranda CIR, Hillsborough

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

Sold listing courtesy of Serena Conti from APR

$5,700,000

6 Beds ⋅ 7 Baths ⋅ ML81941975 MLS

ONE OF HILLSBOROUGH'S MOST IMPRESSIVE BAY-VIEW MANSIONS! Walk to Burlingame! 10 minutes to SFO! You won't believe the architectural quality and drama! Soaring Bay Views for this renovated classic, assigned to North Elementary and within walking distance of Downtown Burlingame Avenue! 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.*Plans available by TRG Architects for Deluxe Carport to match the style of the home

446 El Arroyo RD, Hillsborough

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

Sold listing courtesy of RECIP from RCIP

$5,650,000

4 Beds ⋅ 5 Baths ⋅ ML81935027 MLS

ARCHITECTURAL HAUTE COUTURE: LOWER HILLSBOROUGH CLASSIC, RE-IMAGINED!!! A Secret Office fit for James Bond?! A Primary Walk-In Closet the size of your first New York apartment?! Welcome to a world of character and quality! Built in 1930, this English Country estate bridges the best of storybook chic with a fully remodeled lifestyle of modern luxury. Walk directly from kitchen to yard with no stairs! The energy soars "of the moment" with re-imagined renovations. White marble finishes, appliances by Wolf and Sub-Zero, & expert custom cabinetry cascade throughout 4,125 sq. ft. of destinations. *4 beds, 4.5 baths, plus Office and Lower Level Media Room. *3 En Suites with remodeled bathrooms together *Additional Loft Level for playroom/4th bed with bath *Lower Level Media Room or Gym adjoins Mud Room* Total Privacy in Rear Yard * Updated Marvin windows and doors* Chelmsford Road is a rarely available location within 1.2 miles of downtown Burlingame and 0.7 mile to South Elementary!

540 Chelmsford RD, Hillsborough

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

Sold listing courtesy of Geoffrey Nelson from CBR

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The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than Real Estate Company are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Hillsborough Luxury Style Real Estate & Homes