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$11,500,000
6 Beds 7 Baths ML82055882 MLS
Extraordinary gardens and complete privacy create one of South Hillsborough's most exceptional residences. This circa 1931 Spanish Hacienda home presents a compelling blend of enduring architecture and recently completed updates. Surrounding this gated estate are approximately 2.55 acres of park-like grounds with a separate guest home, cabana, pool, spa and sports court. Signature details of the era remain beautifully intact, from vaulted ceilings, Gothic arched doorways, and all-wood beamed ceilings. Recent improvements introduce a fresh aesthetic, including a remodeled designer kitchen and service area, updated lighting, and refinished hardwood floors. The home balances impressive scale with comfortable livability through a collection of elegant formal rooms, a dedicated office, a tremendous kitchen and family room combination, and lower-level spaces for fitness and staff accommodations. The 5 bedrooms and 5.5 baths in the main residence are complemented by a detached one bedroom guest house plus a pool cabana, while the grounds unfold with meandering pathways, mature trees, and abundant privacy. Bay views from the primary suite add another dimension to this distinguished Hillsborough estate.

862 Chiltern RD, Hillsborough

Listed by Lori Buecheler, 650-387-2716 from Compass
(If provided) CoList: Olivia Maggi from Compass

$6,500,000
6 Beds 6 Baths ML82046653 MLS
Evoking the romance and timeless elegance of classic Spanish Colonial Revival architecture, this enchanting residence welcomes with a sun-drenched brick courtyard framed by lush gardens and climbing bougainvillea. Rich in character, the home showcases exposed wood beams, hand-laid terracotta tile, and artisan-inspired finishes that create a warm yet sophisticated ambiance throughout. Designed for effortless indoor-outdoor living, the expansive courtyard terrace offers multiple gathering spaces ideal for entertaining, quiet mornings, or alfresco dining beneath the canopy of mature landscaping. A sprawling lawn with a grand fountain frame the rear of the property. Charming balconies, arched passageways, and architectural detailing lend an old-world European feel while abundant natural light enhances the homes inviting atmosphere. Inside, the home boasts nearly 6,000 square feet of living space, including multiple separate living quarters perfect for large families, live-in help or guests. Exquisite woodwork and details are abundant throughout the household, with hand-carved fireplaces, curved leaded glass windows, and hand-painted murals. Private, serene, and full of architectural distinction, this is a rare offering that captures the beauty and craftsmanship of a bygone era.

420 El Arroyo RD, Hillsborough

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

Sold listing courtesy of Charles Griffith from MCGR

$70,000,000
6 Beds 17 Baths ML82024133 MLS
Set on more than 12 secluded acres, Villa de Verano is an ultra-exclusive Hillsborough estate inspired by the elegance of Lake Como. The gated compound offers exceptional privacy, symmetry and scale, with a tree-lined drive leading to a grand motor court & the main residence, guest quarters & sports pavilion. The 12,404 sqft main residence spans 3 levels serviced by an elevator & overlooks the pool, reflection pond & sweeping views of San Francisco Bay. The 4,612 sqft guest house & sports pavilion complement the estate. Interior amenities include a fitness center, theater, game room, spa, & saltwater aquarium. Custom furnishings & art create a unified aesthetic. The grounds include an amphitheater, event lawn, Asian garden with koi pond, swimming pool, reflection pond, open air pavilion, rose garden, redwood grove & English spiral mound. The Sports Pavilion includes a 2 story sports lounge with a viewing platform overlooking a sunken tennis court, pickleball court, volleyball court, badminton court, bocce ball court, horseshoe court, shuffleboard court & putting green. The estate also features an executive length golf course. Upon its completion, Villa de Verano received the CLCA annual Grand Sweepstakes Award for best residential estate completed in the state of California.

3000 Ralston AVE, Hillsborough

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

Sold listing courtesy of Jia Xu from TRNX

$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

$8,330,000
5 Beds 6 Baths ML82002467 MLS
In the Burlingame Country Club area, this stunning renovation combines chic sophistication with Spanish flair. Featuring 5 bedrooms and 5.5 baths across two levels, the home has espresso-hued hardwood and Saltillo tile floors complemented by updated lighting, 3 fireplaces with modern style. The floor plan features upstairs living areas and the primary suite opening to the resort-inspired rear grounds, along with two additional bedroom suites. Two bedrooms on the entrance level share a bath. Formal living and dining rooms give way to a remodeled kitchen and family room that includes a study center, and all baths are remodeled with designer touches. Fig-covered walls envelop the wraparound loggia leading to glorious rear grounds with solar-heated pool and spa, heated cabana with barbecue kitchen, fireplace, media, & full bath plus level lawn and built-in trampoline. Ideally positioned midway between Silicon Valley & SF, with minutes-away proximity to SFO and top-rated Hillsborough public & private schools. Open Homes Photography measured the home at 4,784SQFT, 5 BD & 5.5BA. Buyer is to verify and satisfy themselves with square footage, lot size, BD & BA count.

110 New Place RD, Hillsborough

Listed by Alicia Sanguinetti, 650-888-6432 from Compass
(If provided) CoList: Andrew Greenman from Compass

Sold listing courtesy of Alicia Sanguinetti from APR

$8,550,000
5 Beds 7 Baths ML81945061 MLS
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!

862 Chiltern RD, Hillsborough

Listed by Mark Johnson, 650-685-7648 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Lori Buecheler from APR

$3,980,000
4 Beds 3 Baths ML81943537 MLS
Stylish home in lower South Hillsborough. Gracious entry with high ceilings and elegant staircase, grand living room with large arched window opening onto a delightful courtyard that leads out to a level lawn area. The central floor plan includes a formal dining room and charming light-filled breakfast room off the updated kitchen. The updated kitchen includes a Viking cooktop, Thermador double ovens, Subzero refrigerator and built in desk. A large family room opens out to the backyard patio area. The private upstairs features a spacious primary suite with enchanting balcony, dual walk in closets and remodeled bath The updated hall bathroom serves the 2 spacious and bright bedrooms. The functional 4th bedroom on the main floor with built in desk, cabinetry and murphy bed. The adjacent remodeled full bath is conveniently located to be used as a powder room. Beautifully landscaped gardens surround the property adding to the appeal of this exceptional home full of architectural details.

322 Ascot RD, Hillsborough

Listed by Kim Gelman, 650-888-5537 from Compass
(If provided) CoList: from

Sold listing courtesy of Sophia Waldman from SIR

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