View All Hillsborough CA Home Listings - With Guest House

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

$8,000,000

5 Beds ⋅ 5 Baths ⋅ ML82036808 MLS

Situated in Lower North Hillsborough, this gated property encompasses approximately 30,348 square feet flat lot and represents a rare estate-caliber parcel for the discerning buyer. Mature landscaping, privacy, and abundant sun exposure define the setting, just moments from downtown San Mateo, Burlingame Avenues shopping and dining, and top-rated Hillsborough schools. The expansive grounds feature broad lawn areas, a sparkling pool and cabana, detached guest house, greenhouse, two-car garage, enclosed carport, and circular drive, creating a substantial footprint across the site. The existing residence, including a 1997 addition, is approximately 5,533 square feet, offers generous scale and presents an opportunity for significant renovation, reconfiguration, or potential redevelopment. See floor plans for details. Large, flat lot of this size are increasingly scarce in Lower North Hillsborough, providing the opportunity to create a customized estate in one of the Peninsulas most desirable neighborhoods with enduring long-term value.

730 Hillsborough BLVD, Hillsborough

Listed by Alex Hawkins, 408-348-5013 from Cronan Real Estate Services, Inc.
(If provided) CoList: from

Sold listing courtesy of Alex Hawkins from CRNAN

$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

$7,500,000

5 Beds ⋅ 7 Baths ⋅ ML82025050 MLS

Regally set on a private +/-0.71-acre lot with sweeping San Francisco Bay views, this +/-7,435s.f. residence offers luxury, privacy, and an exceptional floor plan. The impressive two-story foyer sets the tone for the elegant formal living and dining rooms, complemented by a rich wood-paneled library. The expansive chef's kitchen features a large island, butlers pantry, and sizable breakfast room, and opens to an enormous family room with built-in bookcases, full bar, and direct access to the stunning rear yard. The main level also offers a game room, guest suite with marble bath, laundry room, powder room, and a wide rear staircase. Upstairs are three spacious en-suite secondary bedrooms, plus a versatile bonus room ideal as a 2nd office, nursery, or gym; and the huge primary suite with Bay views, a fireplace with sitting area, private balcony, spa-like bath with steam shower, and dual custom walk-in closets. The beautifully landscaped grounds offer sweeping patios, level lawns, a pool with spa, play/garden area, and an impressive pool house with kitchenette and full bath. A gated driveway leads to a 3-car garage and motor court. With awe-inspiring views, complete privacy, and resort-style amenities, this grand estate offers an unparalleled lifestyle in an extraordinary setting.

1111 Tournament DR, Hillsborough

Listed by Jim Arbeed, 650-558-4248 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jim Arbeed from CBR

$5,700,000

6 Beds ⋅ 7 Baths ⋅ ML82001959 MLS

35 Brooke CT, Hillsborough

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

Sold listing courtesy of Max Lo from GRBA

$5,150,000

5 Beds ⋅ 5 Baths ⋅ ML81979487 MLS

Spacious and bright, with a fantastic layout and a wonderfully flat yard, the Oak Rim Retreat is the Hillsborough home you have been waiting for. With a ground-floor bedroom suite, sparkling chefs kitchen, four bedrooms upstairs, including a large primary suite with big closets and an oversized soaking tub, and two additional bedrooms and full bath in the separate pool house, this home has space for everybody. The stately facade welcomes you home, and the intelligent floor plan weaves practicality with comfort. And when entertaining, equally impressive - the soaring ceilings of the double-height foyer open up nicely to the living room, which features a modern central fireplace and stylish wet bar. Indoor/outdoor entertaining is easy, with sliding doors in the center of the home that open up from the kitchen to the beautiful backyard, which features a pool, rose planters, plenty of patio space and a large grass play area. The breakfast nook, powder room, family room, formal dining room, and a large three-car garage complete the home. This is it! Welcome home.

1475 Oak Rim DR, Hillsborough

Listed by Laura Lee, 650-455-5326 from Compass
(If provided) CoList: William Cheung from Compass

Sold listing courtesy of Samantha Huang from BHGJF

$14,750,000

6 Beds ⋅ 10 Baths ⋅ ML81959666 MLS

Modern elegance meets unrivaled luxury. This modern luxury masterpiece epitomizes elegance and sophistication situated on a sprawling two acre lot, this estate includes a guest house boasting opulence at every turn with a pool overlooking views that are unmatched. Marvel at the grandeur of 26-foot ceilings and european oak floors as you enter connecting to the gourmet kitchen, adorned with cambria countertops and top-of-the-line gaggenau appliances beckoning culinary excellence. Entertain effortlessly in the game room, indoor/outdoor bar, and gym while indulging in relaxation in the sauna or luxurious jacuzzi tubs. The exterior of this estate adorns european garage doors, italian windows, and a stunning limestone terrace connecting to stunning bay area views. Experience modern luxury living at its finest in this extraordinary residence.

165 Woodridge RD, Hillsborough

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

Sold listing courtesy of Josh Burns from STHB

$8,800,000

8 Beds ⋅ 8 Baths ⋅ ML81946411 MLS

TREASURED LOWER HILLSBOROUGH ESTATE!!! A RARE GEM w/ A HUGE DOUBLE LOT & OVER 1.1 ACRES OF FLAT USABLE LAND! Host w/ confidence thanks to spacious living quarters & a separate 2BR/BA GUEST HOUSE. Sweeping lawns w/ lush grass. Pristine landscaping combined w/ 3 separate patio areas. Sparkling pool & spa + a Cabana. The exterior facade incorporates European elements such as Roman columns. Electronic gate w/ 3 entrances + lots of greenery for privacy & security. The perfect floorplan, a masterpiece of design & functionality. There's hardwood flooring, classic wainscoting, distinct chandeliers, regal fireplaces, crown molding, stained glass windows, recessed lighting, & more. Tall side windows light up the floorplan. Oversized living room & family room. The kitchen is a culinary haven w/ high-end appliances. Multiple ensuite bedrooms + a luxurious primary. Prestigious neighborhood w/ access to sought-after schools. ADRB approved plans for a brand new modern house (available upon request).

420 Roblar AVE, Hillsborough

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

Sold listing courtesy of Stanley Lo from GRBA

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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.