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$7,198,000
4 Beds ⋅ 5 Baths ⋅ ML82032401 MLS
Reimagined in 2023, this Carolands estate balances architectural character with modern ease. Light-filled interiors include a wood-paneled library and formal rooms elevated by custom millwork, statement lighting, and book-matched marble. At the heart of the home, the chefs kitchen features a Wolf rangetop, wine fridge, and an expansive social island. This culinary hub flows into a stunning great room, where French doors open to manicured grounds. The home offers four spacious en-suite bedrooms, including a primary suite with garden views, a custom walk-in closet, and a marble spa bath. Outside, the resort-style grounds feature a classic kidney-shaped pool, vibrant gardens, and an expansive lawn. Perfectly positioned near West Elementary and Highway 280, this property offers quiet luxury in the Peninsulas most coveted enclave.

530 Barbara WAY, Hillsborough

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

Sold listing courtesy of The Patty Dwyer Group from APR
$4,423,560
4 Beds ⋅ 4 Baths ⋅ ML82032273 MLS
Hillsborough opportunity on expansive 21,789+/- SF mostly flat lot. Classic 2-story SFR offers 2,890+/- SF, 4BD, 3.5BA incl 2 en-suites + 1 BD on main level ideal for guests, office or multi-gen living. Vaulted entry, formal living rm w/wood-burning FP, sep family rm w/2nd wood-burning FP & wet bar w/sink. Spacious eat-in kitchen w/abundant natural light, lg pantry & views of backyard & pool. Formal dining rm overlooks yard & mature trees. South-facing rear exposure provides all-day sun. Private backyard w/functioning in-ground pool serviced weekly. Upstairs primary suite w/updated wood flrs & balcony overlooking backyard; addl BD w/private balcony facing street. 3-car garage w/high-end custom wood garage doors. Comp shingle roof. Fresh interior paint, deep cleaned, ext power washed. Property needs loving care & thoughtful updatesrare chance to customize in prime Lakeview location where updated homes command significantly higher values. Excellent Hillsborough public schools. Minutes to Burlingame Ave, Hwy 280/92, top Peninsula amenities. Exceptional upside, setting & scale.

100 Rizal DR, Hillsborough

Listed by James S. Shin, 650-410-8668 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Craig Ackerman from COMP12
$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
$6,000,000
4 Beds ⋅ 4 Baths ⋅ ML82027930 MLS
Sophisticated and beautifully updated, 130 Stonehedge Road offers elegant single-level living in one of Hillsboroughs most desirable enclaves. A formal entry leads to a sun-filled living room with expansive picture windows framing views of the lush grounds. The stunning chefs kitchen features premium appliances, a generous island, and custom cabinetry, connecting seamlessly to the casual living room and the formal dining room for effortless daily living and entertaining. A wide hallway leads to four well-placed bedrooms, including a serene primary suite with a spacious walk-in closet and a spa-inspired bathroom with dual vanities, soaking tub, and separate shower. Additional bedrooms enjoy excellent natural light and access to beautifully finished bathrooms. A versatile bonus room offers ideal space for an office, gym, or studio, complemented by a well-equipped laundry room and a three-car garage. The backyard evokes a private retreat with a large entertaining deck overlooking an expansive level lawn bordered by mature trees and fresh landscaping perfect for gatherings, play, and relaxation. Located just minutes from Burlingame, top-rated public and private schools, local country clubs, and convenient commuter routes to San Francisco and Silicon Valley.

130 Stonehedge RD, Hillsborough

Listed by The Sharp Group, 650-766-5333 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of The Patty Dwyer Group from APR
$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
$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
$4,195,000
4 Beds ⋅ 4 Baths ⋅ ML82023761 MLS
This turn-key, single-level ranch-style residence offers a functional layout with a spacious floor plan that flows seamlessly for both everyday living and effortless entertaining. The expansive grounds are designed for relaxation and recreation, featuring a sparkling pool with a dedicated pool bathhouse, a fire pit with built-in seating, generous yard with great lawn space framed by mature landscaping. A three-car garage provides ample parking and storage. While move-in ready today, the property also presents an exciting opportunity to update or reimagine, creating your dream Hillsborough retreat.

1430 Lakeview DR, Hillsborough

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

Sold listing courtesy of Jenn Gilson from MCGR
$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

$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
$5,650,000
4 Beds ⋅ 4 Baths ⋅ ML82022637 MLS
Situated on a serene and mostly level 0.53-acre lush landscaped lot in desirable Lower South Hillsborough, this exceptional one-level California Ranch-style home offers 4 bedrooms, 3.5 baths, and 3,170 sq ft of functional and spacious living areas. The thoughtful floor plan features a sizeable entry with two coat closets, an expansive light-filled living room with a dramatic floor-to-ceiling stone fireplace, a separate dining room and open kitchen/family room. The remodeled kitchen includes a center island, granite counters, and quality appliances - Thermador ovens, a 5-burner Wolf range, Miele dishwasher, and Sub-Zero refrigerator - opening to a spacious family room flowing to the backyard. The bright primary suite includes a generous bathroom, two walk-in closets and built-in storage. Additional features include warm hardwood floors, recessed lights, a large powder room with two closets, separate laundry room and a 3-car garage. Garden views from nearly every room highlight the verdant landscaping and private yard with a sparkling pool. Ideally located close to top-rated schools, downtown Burlingame and San Mateo, and commuter routes. With its exceptional layout, lush surroundings, and prime location, this property exemplifies the best of California living - all on one level.

135 Rockridge RD, Hillsborough

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

Sold listing courtesy of Maria Scott from CBR
$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
$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
$9,350,000
5 Beds ⋅ 6 Baths ⋅ ML82012753 MLS
Welcome to Villa De Pinehill an exceptional Mediterranean masterpiece nestled on nearly two acres of enchanting, Italian-inspired gardens. Spanning three stories, this estate is a harmonious blend of timeless elegance and modern sophistication. Inside, exquisite craftsmanship is on full display with custom woodwork, premium natural stone, and globally sourced materials that infuse each space with old-world charm and refined luxury. A grand entrance sets the tone for the expansive interiors, featuring soaring ceilings, generously scaled rooms, and a chefs kitchen with a large island that flows seamlessly to the outdoor lawn and detached guest house. The lower level is designed for entertaining, complete with a wine room, full bar, and flexible bonus space. Multiple balconies and terraces overlook the gated, resort-like grounds. Additional amenities include radiant heating, a security system, an outdoor kitchen, three fireplaces, and a hot tub. A private one-bedroom guest house, with its own eat-in kitchen offers an ideal retreat for guests all set within a coveted enclave of equally stunning estates. Main house 7710sqft + guest house 640 sqft

414 Pinehill 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
$5,050,000
5 Beds ⋅ 6 Baths ⋅ ML82016683 MLS
Welcome to 2855 Churchill Drive, a serene retreat in the prestigious Hillsborough community. This elegant 4,340 sqft home offers 5 spacious bedrooms and 5.5 bathrooms, blending timeless design with modern comfort. Inside, hardwood floors, recessed lighting, and statement chandeliers create a warm, refined atmosphere. The chefs kitchen boasts a large center island, breakfast nook, and top-tier appliances ideal for everyday meals or entertaining. Natural light pours through dual-pane windows, enhancing the open layout and cozy fireplace. Host in the formal dining room, work from the home office, or unwind in the media/recreation room. The primary suite features a spa-like ensuite with soaking tub, separate shower, and dual vanities. All bedrooms include generous space and walk-in closets. Outside, enjoy a private backyard oasis perfect for relaxing or gathering with friends. Additional perks include central heating and a full laundry room with washer and dryer. Experience luxury, comfort, and California living at its finest.

2855 Churchill DR, Hillsborough

Listed by Curtis Lim, 650-678-6805 from Compass
(If provided) CoList: from

Sold listing courtesy of DeLeon Team from DLRPA
$4,820,000
6 Beds ⋅ 6 Baths ⋅ ML82012939 MLS
COMP PURPOSES ONLY

2905 Privet 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
$4,180,000
4 Beds ⋅ 3 Baths ⋅ ML82011873 MLS
ONE OF HILLSBOROUGH'S BEST DEALS!!! Nestled in the prestigious Tobin Clark Estates, this home blends privacy, timeless architecture, and classic elegance. Surrounded by pristine landscaping and gently rolling hills, it's located in one of the Peninsulas most desirable neighborhoods. The home itself is seated on almost 1/2 acre of flat land. A long motor court driveway with elegant concrete pavers leads to the entrance, framed by mature trees and clean white trim. Inside, expansive living spaces are filled with natural light thanks to tall windows and glass doors. Here you'll also find high vaulted ceilings and recessed lighting. The living and family rooms each open to the backyard, and the floor plan of the family room flows seamlessly into a bright breakfast nook and a well-equipped kitchen. A formal dining room offers space for hosting. Bedrooms are comfortable, with a spacious primary suite featuring a spa-like bath and large closet. Outside, enjoy a sparkling pool and spa, patio, lawn, and a charming guest/pool house with a full bedroom & bathroom (not include in total bed/bath count). Additional highlights include a 3-car garage and indoor laundry/mudroom. Conveniently close to top-rated schools, and just minutes from downtown San Mateo and Burlingame. THIS HOME HAS IT ALL!

937 Parrott DR, Hillsborough

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

Sold listing courtesy of The Patty Dwyer Group from APR
$6,530,000
5 Beds ⋅ 5 Baths ⋅ ML82010779 MLS
NEW PRICE!! Nestled on .66 acres in Lower North Hillsborough, this stunning home is located near North Hillsborough School. The 2-story foyer leads to a spacious LR w/ fireplace insert, recessed lighting, built-in speakers, & large windows framing tranquil views of lush greenery. The formal DR offers picturesque views of patio & pool. The oversized eat-in kitchen boasts granite countertops, & custom wooden cabinetry. It comes equipped w/high-end appliances, including 2 dishwashers, Viking refrigerator, 6-burner range, & double ovens. The breakfast area opens rear patio, enhancing the kitchen's flow. The spacious family rm has soaring ceilings, 2 skylights, built-in speakers, fireplace, & bar w/ wine fridge, sink, & an add'l refrigerator. A powder room is situated off the entry. Also on main level is office or 5th BR, w/its own full bath. Upstairs, a generously sized primary BR suite features luxurious walk-in closet, fireplace, & access to private balcony. The attached bathroom has skylight, double-headed shower, & double sinks. 3 add'l BRs, 2 more bathrooms, & a laundry rm complete the 2nd level. Add'l features include a 3-car garage w/built-ins, 2 furnaces, & 2 AC units. The rear patio & yard offer a serene oasis, w/ pool, 2 spas, & outdoor kitchen w/BBQ area.

801 Eucalyptus AVE, Hillsborough

Listed by Austin Herman, 650-773-8652 from Compass
(If provided) CoList: Susan Herman from Compass

Sold listing courtesy of Vahid Firouzdor from COMPS
$5,125,000
4 Beds ⋅ 4 Baths ⋅ ML82010031 MLS
Located in lower Skyfarm, this beautifully updated classic ranch is introduced by a circular motor court and refreshed landscaping on approx. 0.63 acres. Timeless details include parquet and hardwood floors, crown moldings, and wainscot paneling, with freshly painted interiors and new lighting. The living room impresses with a coffered ceiling, marble fireplace, and French doors to the pool and serene canyon-view grounds. A formal dining room, gourmet kitchen with granite slab countertops and high-end appliances, and adjacent family room provide ideal spaces for everyday living. A dedicated office/library offers dual access to the living room and primary suite. The flexible floor plan includes 4 bedrooms and 3.5 baths, with the primary suite and two bedrooms in one wing and a separate guest/au pair bedroom and bath near the kitchen and garage. Outdoor living is enhanced by large decks, dark-bottom pool, and play areas all with canyon views. Excellent Hillsborough schools, including North Elementary and Crocker Middle School.

2295 Skyfarm DR, Hillsborough

Listed by Raziel A. Ungar, 650-720-5483 from Compass
(If provided) CoList: from

Sold listing courtesy of Mike Bohnert from CBR
$3,500,000
4 Beds ⋅ 4 Baths ⋅ ML82009068 MLS
Opportunity awaits at 2845 Churchill Drive in Hillsboroughs prestigious Skyfarm neighborhood. This stately Tudor-style home sits on a large, private lot at the end of a quiet cul-de-sac and offers endless potential to create your dream residence. With 4 bedrooms and 3.5 baths, the home features a generous layout with formal living and dining rooms, a family room, and a spacious kitchen ready for reimagining. The expansive backyard includes a pool, spa, and mature landscaping an ideal canvas for personalized outdoor living. Whether you're looking to restore its original charm or redesign with a modern vision, this is a rare chance to put your personal touch on a timeless Hillsborough property. Prime location near top-rated schools and just minutes to downtown Burlingame.

2845 Churchill DR, Hillsborough

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

Sold listing courtesy of Emma Elfving from APR
$4,500,000
4 Beds ⋅ 4 Baths ⋅ ML82008449 MLS
Experience the Ultimate in Hillsborough Luxury Living! This Mediterranean-inspired estate in the prestigious Carolands neighborhood offers unparalleled privacy, elegance, and modern amenities. Step inside to discover a grand foyer, vaulted ceilings, and expansive windows that bathe the home in natural light. The gourmet kitchen, featuring a Viking range, a center island, and custom cabinetry, flowing seamlessly into the family room with a stunning stone fireplace. French doors lead to an outdoor oasis with a sparkling pool, spa, heated cabana/pool house, and an outdoor kitchen perfect for entertaining. The outdoor pool cabana features a bathroom. The luxurious primary suite offers vaulted ceilings, a custom walk-in closet, and a spa-like bath with dual rain showers. This home also features lots of custom cabinetry throughout, a new drainage system, and beautifully landscaped grounds. Too many details to list here. Located just minutes from bustling Downtown San Mateo and offering easy access to Highway 280, this estate blends Mediterranean charm with modern upgrades, creating a one-of-a-kind retreat.

1260 Hayne RD, Hillsborough

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

Sold listing courtesy of Nona Ehyaei from COMPS
$8,000,000
5 Beds ⋅ 6 Baths ⋅ ML82007876 MLS
Located in Hillsboroughs coveted Carolands neighborhood, this exceptional 5BD/5.5BA home has been meticulously renovated and expanded to exemplify modern luxury living. Situated on a generous half-acre lot, the property offers a private retreat with a swimming pool and spillover spa. Enjoy seamless indoor-outdoor living with an open floor plan, soaring ceilings, skylights, and La Cantina doors. The chefs kitchen features high-end Miele appliances, including a built-in coffee machine and walk-in pantry. The primary suite boasts a walk-in closet and a spa-inspired bathroom with an oversized vanity, curbless walk-in shower, and soaking tub. The versatile lower level includes a family room with a second kitchen, perfect for entertaining alongside a dedicated exercise room with an infrared sauna to promote wellness. A separate poolside shed provides an ideal space for a home office, and the custom theater offers an immersive viewing experience with lounge seating and surround sound. Additional upgrades encompass smart home technology w/ Ubiquiti cameras, and pre-wiring for WiFi access points. The professionally landscaped backyard features artificial turf, grass, sand play area, and a tranquil water feature. A spacious 3-car garage completes this exceptional and turnkey property.

510 Darrell RD, Hillsborough

Listed by Mike Danao, 650-274-8890 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Jenn Gilson from MCGR
$5,275,000
4 Beds ⋅ 4 Baths ⋅ ML82002925 MLS
This single-level, 4-bedroom, 3-bathroom home offers 3,020 sq. ft. of comfortable living space on a 23,053 sq. ft. lot, featuring a spacious kitchen, formal dining room, versatile living areas, a 3-car garage, and access to the Hillsborough City Elementary School District.

20 Cedar CT, Hillsborough

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

Sold listing courtesy of Jenn Gilson from MCGR

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