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$6,750,000
5 Beds ⋅ 6 Baths ⋅ ML82031249 MLS
An architectural statement of grand scale and enduring quality, this stately Skyfarm residence is nestled behind a mature landscape of majestic evergreens, offering privacy and a seamless connection to its natural grounds. Spanning 5,770± sq. ft. on an expansive 32,633+/- sq. ft. lot, the home is in pristine original condition and is poised for the next generation family to infuse with their own vision. The interior is defined by classic precision: refinished hardwood floors, raised wood paneling, crown molding, bay windows and Old World quality. A two-story foyer with chandelier leads to the grand living room, featuring a distinguished fireplace and backyard views, a formal dining room for refined venues, an eat-in kitchen, anchored by a center island, and an adjoining family room with a masonry fireplace and window wall blurring the boundary between indoors and the sprawling rear grounds. A spacious primary suite featuring generous wardrobe space and a scenic view headlines the upper level. Beyond the residence, irrigated grounds with sweeping lawns and patios create a private, park-like retreat. 1080 Macadamia Drive is a rare convergence of scale, land, and lifestyle.

1080 Macadamia DR, Hillsborough

Listed by Julie Baumann, 650-576-8889 from Compass
(If provided) CoList: from

Sold listing courtesy of Sandra Comaroto from APR
$7,300,000
5 Beds ⋅ 3 Baths ⋅ ML82029393 MLS

460 Barbara WAY, Hillsborough

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

Sold listing courtesy of Gina Haggarty from APR
$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
$12,300,000
4 Beds ⋅ 6 Baths ⋅ ML82029221 MLS

7 Windsor DR, Hillsborough

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

Sold listing courtesy of Rob Decontreras from KWPEN
$12,400,000
5 Beds ⋅ 7 Baths ⋅ ML82028559 MLS
Stunning Custom Built New Construction Home with Breathtaking Views. Formal Entry. Elegant Living Room with High Ceilings and Floor-to-Ceiling Windows. Chef's Eat-in Kitchen with Center Island with Sink, Pantry, and Ample Natural Light. 5 Spacious Bedrooms. 5 Beautifully Designed Full Bathrooms and 2 Half Bathrooms. Primary Suite Retreat Features Double Sinks, Standalone Tub, Stall Shower, and Walk-in Closet. Main Floor Bedroom Suite. Upper Level Features Separate Family Room with Bar and Half Bathroom. Exterior Features Includes Sparkling Pool, Outdoor Kitchen, and Floating Deck. Lovely Landscaped 1.33+/- Acre Lot with Breathtaking Views. Award Winning Hillsborough Schools

20 Pine CT, Hillsborough

Listed by Keri Nicholas, 650-533-7373 from Parc Agency Corporation
(If provided) CoList: from

Sold listing courtesy of Kalina Wasman from COMPS
$4,900,000
5 Beds ⋅ 4 Baths ⋅ ML82028079 MLS

1015 Woodland DR, Hillsborough

Listed by Stephanie Nash, 650-995-3820 from Compass
(If provided) CoList: from

Sold listing courtesy of Nicholas Delis from APR
$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
$5,860,000
5 Beds ⋅ 5 Baths ⋅ ML82026911 MLS
LOWER SOUTH CHALET: ARCHITECTURAL SIGNIFICANCE MEETS FAMILY WARMTH! Homes are simply not built with this high style anymore! A rarity to the market, this is an architecturally significant statement equally at home as a fine art gallery or warm and cozy family retreat. Sophistication cascades throughout truly ENORMOUS room sizes, while never compromising daily function and inviting indoor/outdoor character. In the heart of Lower South Hillsborough, we celebrate one of the San Francisco Peninsula's top luxury enclaves, a neighborhood ranking within the Top 10 on median sales price in the United States, decade after decade. Around the corner from $18,000,000 estates, less than a mile from Crystal Springs Uplands, just 1.4 mile from North Elementary, 1.7 mile to downtown Burlingame Ave Apple Store. The romance of the Chalet is the theme: rustic charm with contemporary features. Sequestered within noble trees, imbued with spirit of a special-occasion getaway, & arresting in design flair, this is your conversation piece. | 5 beds, 4.5 baths | Expanded & Updated by acclaimed architect John A. Matthews, AIA | Huge Master Suite | Side Party Terrace | Separate Pool Area | Mill Valley-style woodsy vibes w/easy ADU potential | 4-car attached garage + motor court for basketball & yard access

300 Glendale RD, Hillsborough

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

Sold listing courtesy of Disen Cai RE Group from KWPEN
$9,700,000
6 Beds ⋅ 4 Baths ⋅ ML82025915 MLS
An exceptional opportunity on one of Lower North Hillsboroughs most coveted streets. Set on a sun-filled, flat lot of over three-quarters of an acre, this property offers limitless potential for the discerning buyer seeking a rare, estate-caliber parcel. Brewer Drive is among Hillsboroughs most distinguished addressesrenowned for its timeless architecture, wide lots, and proximity to Downtown Burlingame, San Mateo, and top-rated Hillsborough schools. The existing 1920s residence spans approximately 4,000 square feet and showcases elegant period details, gracious proportions, and classic design elements throughout. A gated circular driveway provides a stately approach, while the grounds feature a sparkling pool, manicured rose gardens, a detached two-car garage, and additional storage structures. Whether restoring the existing home or reimagining the site for a new estate, this premier Brewer Drive location presents a truly rare offering in one of the Peninsulas most sought-after neighborhoods.

715 Brewer DR, Hillsborough

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

Sold listing courtesy of Jenn Gilson from MCGR
$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
$5,485,000
4 Beds ⋅ 4 Baths ⋅ ML82025814 MLS
Arrive through a grand circular driveway to this beautifully expanded and remodeled 4-bedroom + office, 3.5-bath residence set on a .41-acre flat lot in sought-after Lower South Hillsborough. Inside, classic elegance meets open modern living. The chefs kitchen flows seamlessly into the family, dining, and breakfast areas, overlooking the private backyard with lawn, patio, and mature gardens perfect for entertaining or quiet afternoons at home. The main level also features a formal living room, private office, guest suite with adjacent full bath, and a custom laundry room. Upstairs, the primary suite offers a spa-like retreat with a soaking tub, standing shower, dual sinks, and two additional sun-filled bedrooms sharing a remodeled bath. Located just moments from Burlingame Avenue and downtown San Mateo, and within top-rated South Elementary School and Crocker Middle School, this is timeless Hillsborough livingrefined, walkable, and effortlessly elegant.

310 Ranelagh RD, Hillsborough

Listed by Sternsmith Group, 650-678-5455 from Compass
(If provided) CoList: from

Sold listing courtesy of Sternsmith Group from APR
$4,579,000
6 Beds ⋅ 6 Baths ⋅ ML82025146 MLS
Fresh updates, incredible Bay and airport runway views, and impressive scale on more than one-half acre. Predominantly arranged on one level, the 6-bedroom, 5.5-bath floor plan has remarkable flexibility with options to accommodate offices, guest quarters, recreation, fitness, and more. Every room opens to the outdoors with 3 front terraces overlooking the Bay plus a tremendous newly built deck in clear redwood. Freshly painted inside, refinished hardwood floors, and new carpet in some rooms ready for immediate enjoyment and also an opportunity to further transform. Grand entertaining spaces include a vast living room, formal dining room, kitchen designed for a true chef with both gas and electric cooktops plus wok burner, and a tremendous family room. Peaceful non-through street just minutes from top Hillsborough schools including West and Crocker, hiking trails, and Highway 280 to San Francisco and Silicon Valley.

30 Live Oak LN, Hillsborough

Listed by Sandra Comaroto, 650-714-1359 from Compass
(If provided) CoList: from

Sold listing courtesy of Judy Zhu from CBR
$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
$6,850,000
6 Beds ⋅ 7 Baths ⋅ ML82024643 MLS
Set amid the rolling hills of Hillsborough, 1535 Lakeview Drive is a distinguished estate that pairs timeless elegance with modern comfort. Tucked behind a gated driveway, the home sits regally surrounded by mature trees and manicured landscaping that evoke a sense of privacy. This 6-bedroom, 6.5-bath residence spans approximately 6,690 square feet on a nearly one-acre lot, offering generous space for both everyday living and entertaining. Inside, airy living areas are framed by large windows that connect the indoors to the surrounding greenery. The homes thoughtful floor plan features multiple gathering spaces, including formal living and dining rooms, a spacious family room, and a chefs kitchen designed for connection and ease. Each bedroom suite is its own retreat, while the primary suite offers serene garden views and spa-inspired amenities. Outdoors, the lush grounds invite year-round enjoyment with terraced patios, winding pathways, room to add a pool and ideal for entertaining. 1535 Lakeview Drive embodies the best of Hillsborough living, refined, private, and effortlessly grand

1535 Lakeview DR, Hillsborough

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

Sold listing courtesy of Mary Bee from CBR
$7,495,000
5 Beds ⋅ 5 Baths ⋅ ML82023917 MLS
Situated on a serene cul-de-sac, this stunning, fully renovated modern farmhouse offers resort-style living on a mostly level +/-0.52-acre lot. With +/-4,200 s.f. of bright open space, the 5BR/4.5BA Napa Valley-style home features soaring ceilings, wide-plank hardwood floors, and walls of windows that flood the interior with light. A striking glass front door opens to the living room with dramatic fireplace and verdant views. The elegant dining room includes a sleek, temperature-controlled wine display, while the chef's kitchen with top-tier appliances, large island, and breakfast nook flows into the expansive great room with access to the backyard. The private bedroom wing offers 4 sizeable bedrooms, one with an ensuite bath, a separate hall bath, powder room, laundry, and the lavish primary suite with custom walk-in closet and spa-inspired bath with soaking tub & oversized shower. Additional spaces include an attached ADU with kitchenette, full bath which opens to the pool patio, and loft, plus a versatile lower-level bonus room ideal as an office or gym, and 3-car garage. Resort-like grounds boast mature olive trees, stunning landscaping, sprawling patio, level lawn, outdoor kitchen, and new pool with spa. A rare opportunity to own a virtually new home in a remarkable setting.

35 Bel Aire CT, Hillsborough

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

Sold listing courtesy of Vikrant Goel from SFLT01
$14,980,000
7 Beds ⋅ 8 Baths ⋅ ML82012140 MLS
SELLER ALREADY PURCHASED AND WOULD LIKE TO REVIEW ALL OFFERS! *MILLION DOLLAR REDUCTION!!!* HILLSBOROUGH'S BEST IN CLASS, THIS IS LUXURY! MUST SEE!!! 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 additional ensuite bedrooms & attic storage offer comfort & flexibility. The lower level is a true entertainers dream featuring a cinema-quality home theater, game room & kitchenette.

1600 Marlborough RD, Hillsborough

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

$6,780,000
7 Beds ⋅ 6 Baths ⋅ ML82023191 MLS
Vista Southdown: Private Sanctuary, Panoramic Views Main Residence: 6 Bedrooms & 4 Bathrooms | Luxury Dual Story Casita ADU: 1 Bedroom & 2 Bathroom | 5,065 +/- SQ FT | Chefs Kitchen: Thermador Appliances with Dual Wine Fridges & Stone Countertops | Outdoor Paradise: Resort-Style Pool & Spa, BBQ & Sport Court | Bay Views & Lush Grounds: Breathtaking Bay Panoramas, Curated Landscaping and Refined Outdoor Lighting | Primary Ensuite with Large Soaking Tub and Stall Shower | Modern Flooring | Centralized Heating and A/C | Discreetly Protected: Advanced Surveillance Ensuring Comfort and Privacy Nestled among the redwoods with sweeping views of San Francisco and the San Mateo Bridge, 1221 Southdown Road is a modern Hillsborough estate that balances timeless design with contemporary living. Reimagined by designer Ashley Canty, this residence is a statement of style, comfort, and California luxury. The grounds mirror the elegance of the interiors, featuring a sparkling pool and spa, covered loggia, landscaped play areas, turf field, and private terraces for relaxation or recreation. Natural palettes & refined finishes root the home in its hillside setting, with stone, wood, and glass framing the beauty of the landscape. California living at its finest.

1221 Southdown, Hillsborough

Listed by Cullinan Luxury, 650-773-2321 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Stanley Lo from GRBA
$7,300,000
5 Beds ⋅ 7 Baths ⋅ ML82022917 MLS
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.

625 W Santa Inez AVE, Hillsborough

Listed by Vivian Shao, 650-307-7311 from Green Banker Realty
(If provided) CoList: Chi-hwa Shao from Green Banker Realty

Sold listing courtesy of Jim Arbeed from CBR
$5,900,000
5 Beds ⋅ 5 Baths ⋅ ML82022735 MLS
THE RULES OF REAL ESTATE ATTRACTION: LOCATION, LIVABILITY, MOVE RIGHT IN! The great lifestyles always seem to have a universal appeal and purity of function. Here, in the heart of Lower North Hillsborough estate country, we find a smooth single-story design, totally renovated, ready to purvey the universal luxury of the Peninsula. How rare art thou? Let me count the ways...this single-story design is surely scarce at any price point: no stairs to worry about, all remodeled condition, and a 5-bedroom, 4.5 bath floorplan opening out to flat private garden. These picturesque environs, dappled by vintage oaks & timeless mansions, are within a 30 minute stroll of downtown Burlingame Avenue. | Dramatic Lobby of 12 ft +\- ceilings | Living and Dining Rooms are elegant statements with 10 ft. 4 inch ceilings & bay windows | Grand size open rooms treated with hardwood floors, crisp white moldings, designer palette | Large updated chef's kitchen open with bistro nook | Huge Family Room Opens to Flat Yard | Separate Bedroom Suite ideal for Office or In-Law|Au Pair with private entry | Immense Master Suite with 2 walk-in closets & marble bathroom + soothing green garden view | Immaculate condition and perfect Floorplan | Walk to Burlingame Ave | Top Schools | #1 Neighborhood amongst mansions

515 N San Raymundo RD, Hillsborough

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

Sold listing courtesy of Raziel A. Ungar from APR
$12,000,000
5 Beds ⋅ 7 Baths ⋅ ML82010473 MLS
Rare, once-in-a-lifetime luxury estate in the prestigious Ryan Tract of Lower Hillsborough. Set on a flat 42,304 sq ft gated lot, this property offers 5 beds, 6.5 baths, solar, regulation tennis court, large pool + separate spa, lush gardens, expansive lawns, multiple patios, putting green, outdoor BBQ, long private driveway, motor court, and 3-car garage. The main residence features an elevator; all bedrooms en-suite; chefs kitchen with butlers pantry; family room; living room; formal dining room; multiple office/workshop spaces; and more. Additional structures include a pool house and a full guest house attached to the garage. Total advertised living space of 7,950 sq ft includes the main house, 945 sq ft 2-bed/2-bath guest house with full kitchen and living/dining area, and a 685 sq ft pool house with living space, kitchenette, laundry, full bath, and sauna. Walking distance to Downtown Burlingame and access to top-rated California schools. A true blend of elegance, scale, and resort-style living.

818 Irwin DR, Hillsborough

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

Sold listing courtesy of Stanley Lo from GRBA
$4,780,000
5 Beds ⋅ 6 Baths ⋅ ML82022295 MLS
Exceptional private and gated estate on a rare 25,990 sq ft corner lot in Hillsboroughs most prestigious enclave. Elevated and secluded with lush landscaping, soaring trees, and a grand presence. Two luxurious primary bedroom suites on the main level feature spa-style baths with Jacuzzi tubs, glass showers, dual vanities, large walk-in closets, wet bars in the 2 masters bedroom and 1 in the family room, offering the ultimate in comfort and convenience. Ideal for multi-generational living or hosting in style. Dramatic foyer with high ceiling, sweeping staircase, elegant column accents, formal living and dining rooms, and a sun-filled family room with a built-in wet bar, perfect for entertaining. The gourmet kitchen boasts granite counters, high-end appliances, an island with a second sink, and a cozy breakfast nook. Upstairs offers an additional primary suite, a spacious loft, and a private balcony. Resort-inspired amenities include a rooftop lounge, private courtyard, sports court, detached three-car garage, and a gated driveway. A rare opportunity for luxury, privacy, and seamless indoor-outdoor living.

1531 Wedgewood DR, Hillsborough

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

Sold listing courtesy of Alex Buljan from APR
$4,800,000
5 Beds ⋅ 7 Baths ⋅ ML82022191 MLS
For the very first time in its storied history, this 1936 family estate is being offered to the public. This classic English Tudor is a landmark in its own right, a home that gracefully bridges Hillsborough's past and present. Set on nearly an acre of level land with views of the Bay and San Francisco skyline, the residence embodies timeless elegance. Its centerpiece is a remarkable floating spiral staircase anchored only at the bottom and top. With a large open kitchen connecting to the family room, plus 5 bedrooms and 5 full bathrooms (2 half baths), the estate is ready and waiting for its next owner (some photos are virtually staged)! There is a bedroom, library and full bathroom on the main level. The primary bedroom and 3 add'l bedrooms are upstairs. Outdoors, the gardens carry the signature of renowned landscape architect Thomas Church, whose designs shaped much of California's most beautiful private estates with broad lawns, graceful plantings and private spaces. Built by the Wisnoms, one of the founding families of San Mateo, The National Bank of San Mateo and cousins of Wisnoms Hardware family. This offering represents a rare opportunity: to own a piece of Hillsborough history and to become the next steward of a home designed with both legacy and livability at its core.

923 Hayne RD, Hillsborough

Listed by The Patty Dwyer Group, 650-703-1183 from Compass
(If provided) CoList: from

Sold listing courtesy of Serena Conti from APR
$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
$8,600,000
6 Beds ⋅ 7 Baths ⋅ ML82021146 MLS
ICONIC 1920'S DUTCH COLONIAL-STYLE HOME LOCATED ON ONE OF HILLSBOROUGH'S MOST COVETED STREETS. THIS ELEGANT HOME HAS BEEN THOUGHTFULLY REMODELED WITH TOP-OF-THE-LINE MATERIALS AND FINISHES. THIS 6800+SF ESTATE OFFERS 6 BEDROOMS 5 FULL AND 2 HALF BATHS, AN AU PAIR SUITE, AND A SPACIOUS LAYOUT. ABUNDANT NATURAL LIGHT CAPTIVATES THE INVITING AMBIANCE SHOWCASING THE AMAZING DETAIL THROUGHOUT THE PROPERTY. THE FORMAL DINING ROOM FEATURES ELEGANT FLORAL WALLPAPER AND WAINSCOATING. THE FAMILY ROOM, MEDIA ROOM AND GYM PROVIDE AMPLE SPACE FOR ENTERTAINMENT AND RELAXATION. OUTSIDE YOU WILL FIND A BUILT-IN BBQ, FIREPIT, AND SPORTS COURT, PERFECT FOR OUTDOOR ACTIVITES AND FAMILY FUN! THE SPACIOUS FLOORPLAN FEATURES 5 BEDROOMS UPSTAIRS, WITH A GENERIOUS SIZED PRIMARY SUITE. THIS HOME ALSO OFFERS A PRIVATE OFFICE WITH 1/2 BATH. THIS HOME IS CONVENIENTLY LOCATED WITHIN A SHORT DISTANCE TO BURLINGAME AVE AND TOP RATED NORTH ELEMENTARY AND CROCKER MIDDLE SCHOOL.

720 Brewer DR, Hillsborough

Listed by Nick Corcoleotes, 650-207-2758 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Phil Chen from SGP
$6,807,000
4 Beds ⋅ 4 Baths ⋅ ML82020625 MLS
Luxury meets modern design in this stunning +/-4,485s.f. custom home by renowned Mak Studio Architects of San Francisco. Situated on a +/-0.50-acre lot with S.F. Bay views, this 4BR/3.5BA home was designed with impeccable attention to detail and is a sanctuary of modern elegance and tranquility. The open concept layout features soaring ceilings, rich hardwood floors, & dramatic floor-to-ceiling windows throughout. The living room with custom cabinets & sleek fireplace flows seamlessly to an expansive terrace covered by a motorized pergola and features a fire pit & outdoor kitchen - ideal for indoor/outdoor entertainment. The chic dining room with wall-to-wall windows showcases the lush scenery, while the chef's kitchen dazzles with top-tier appliances, island & butler's pantry, and opens to the expansive great room with amazing views. A private office with built-in desks offers the perfect work-from-home space. The lower level features 4 bedrooms, including a Zen-inspired primary suite with a wall of windows, fireplace, custom closets & spa-like bath. A large wine room & media room with rear yard access complete this level. The verdant, private grounds boast a huge level lawn, meandering pathways & multiple fruit & citrus trees. Truly a one-of-a-kind retreat in turnkey condition.

5 Drayton RD, Hillsborough

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

Sold listing courtesy of Victor Lo from SRAI
$8,000,000
5 Beds ⋅ 5 Baths ⋅ ML82020606 MLS
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.

75 Eugenia WAY, Hillsborough

Listed by Donald Kung, 650-219-8700 from Remax Capital
(If provided) CoList: from

Sold listing courtesy of Cici Wang from CBR
$6,660,000
4 Beds ⋅ 5 Baths ⋅ ML82019925 MLS
REDUCED OVER $1 MILLION, SELLER HAS PURCHASED ANOTHER HOME SO THIS PROPERTY HAS BEEN REDUCED FOR A QUICK SALE! THE BEST VALUE FOR A SINGLE STORY PROPERTY IN LOWER HILLSBOROUGH. BUILT IN 2004 WITH STUNNING RENOVATIONS! TURN-KEY & MOVE-IN READY! EVERYTHING YOU COULD WANT: Prime location, modern top-of-the-line updates & remodels, newly designed landscaping, oversized corner-lot, solar panels, high ceilings, smart home features, sports court, huge sparkling pool, vast lawn & backyard for kids to play, outdoor kitchen, pool house with kitchenette & bathroom, outdoor spa, dual-sided fireplace, rich hardwood floors, gorgeous chefs kitchen with all high-end built-in stainless steel appliances, an oversized island, kitchen-family combo (perfect for entertaining), large bedrooms, 3-car garage, EV car charging, & SO SO MUCH MORE! On top of all that, you'll get a home that is ideally located just minutes from top-rated schools, downtown Burlingame, and major Silicon Valley commuter routes; this home offers a rare combination of luxury, privacy, and convenience. IT DOESN'T GET BETTER THAN THIS, PRICED TO SELL SO DON'T WAIT!!!

380 Arden RD, Hillsborough

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

Sold listing courtesy of Kenny Zhang from VHVOG
$5,325,000
4 Beds ⋅ 4 Baths ⋅ ML81990249 MLS
A stunning bucolic estate within the exclusive Hillsborough hills perches at the end of a long, private cobblestone drive. This well-appointed home offers 4,240 sq ft of living space on 2.24 acres with views from virtually every room. Backyards large entertaining patio includes a pool/spa, BBQ area and lifesize Kung Fu Panda statue. Kitchens picture windows let natural light gleam off long granite counters and Viking stove. Sizable vaulted family room adjoins for casual dining. A door off the kitchen leads to dining and living rooms, both with coffered ceilings and wainscotting. Primary Suite impresses with marble-appointed bath, while 2 guest beds have ample closets and share a marbled hall bath that offers much space. Lower level offers a spacious media room, home gym and ensuite bedroom. Mud room off the 3-car garage offers laundry, storage and full bath with sauna. Tremendous grounds and ideal floor-plan in a prized neighborhood make this Hillsborough property a must-see.

2530 Skyfarm DR, Hillsborough

Listed by Gina Haggarty, 650-207-5192 from Compass
(If provided) CoList: from

Sold listing courtesy of Phil Chen from SGP
$5,210,000
4 Beds ⋅ 5 Baths ⋅ ML82018061 MLS
First time on the market ... ever! Mid-century vibes, SF views & a pool in Hillsborough. What is most striking when you walk in are the walls of glass that capture sweeping views of San Francisco and bathe the home in natural light. The main level flows easily between the living room, dining room, and great room/kitchen, opening to terraces perfect for entertaining and dining. The kitchen features a custom-made copper range hood, large island and new oven/stove. There's also a separate catering kitchen plus an office. The primary bedroom has two sitting areas, ensuite bathroom and walk-in closet. There's 3 more bedrooms downstairs plus a family room. The focal point of the tropical-inspired yard is a spectacular palm tree that sways beside a swimming pool and spa surrounded by lawn and privacy. Don't miss the secret wine-room and various pathways, gardens and surprises throughout the property! Hillsborough is also an ideal place to live situated between San Francisco and Silicon Valley with top-rated public and private schools.

940 Hayne RD, Hillsborough

Listed by The Patty Dwyer Group, 650-931-2036 from Compass
(If provided) CoList: from

Sold listing courtesy of Jeff Harber from APR

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