Refine Search
Sort by
$4,760,000
3 Beds 4 Baths ML82005190 MLS
Tucked beneath a canopy of majestic redwoods, this stylish single-level home blends timeless design with effortless indoor-outdoor living, and sits on one of Hillsborough's most coveted streets in Lower South Hillsborough. Fully reimagined in 2017, the residence offers 3 bedrooms, 3.5 bathrooms, and 2,352 square feet of thoughtfully designed space on a nature-filled lot in one of Hillsboroughs most desirable locations. Every room connects seamlessly to the outdoorswhether its the serene backyard retreat off the primary suite or the barbecue-ready dining area just off the kitchen. The open-concept layout is anchored by a chic modern kitchen that flows into two inviting living areas, one with a cozy fireplace perfect for quiet evenings or casual entertaining. Moments from both Downtown Burlingame and Downtown San Mateo, this home offers the perfect balance of tranquility and convenience.

244 Roblar AVE, Hillsborough

Listed by The Laugesen Team, 650-465-5742 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of The Laugesen Team from KWPEN

$6,250,000
5 Beds 5 Baths ML82004231 MLS
Perfectly situated in the heart of South Hillsborough, 280 Uplands Drive offers a rare opportunity on an expansive, flat over half-acre lot surrounded by beautiful estates. Rebuilt and remodeled approximately 35 years ago, this 5-bedroom, 4.5-bath home spans nearly 5,000 square feet and features a generous floor plan, lush landscaping, and a swimming pool. While currently owner-occupied and not fully showcased, this property boasts exceptional bones and unlimited potential. Whether you are looking to remodel, expand, or create your dream estate, this prime location offers the perfect canvas to match your lifestyle. Very Easy to show anytime, call Mike at 650773 0266 for showing appointment. Don't miss this one!

280 Uplands DR, Hillsborough

Listed by Michael Haywood Jr., 650-773-0266 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Michael Haywood Jr. from EXPCA

$4,300,000
4 Beds 4 Baths ML81994975 MLS
Discover upscale living in this 3520 sq ft Hillsborough residence, featuring a beautifully updated kitchen with high-end Thermador appliances, eat-in area, wine bar, skylights, and formal dining room. The expansive, light-filled living room with vaulted ceilings elevates the home's elegant interiors. The first-floor primary suite has high ceilings and boasts a vast walk-in closet and a spa-like bath with luxurious tubs and showers. The lower level offers a bedroom suite, two additional bedrooms, a homework station, and a separate laundry room with wine storage. The extensive 38,332 sq ft lot includes an outdoor kitchen, fountain, fire pits, and a lush garden, perfect for hosting gatherings. Additional amenities like a kids' play area, putting green, bocce ball court, and basketball court cater to an active family lifestyle. This property combines luxury with functionality, making it an ideal choice for those seeking a sophisticated & comfortable living space. Enjoy the serenity of a well-appointed home nestled in a prestigious neighborhood, designed to cater to every need of a discerning homeowner and with 3 of the bedrooms being walk-in level, it's perfect for those seeking multi-generational comfort. Photos are for marketing purposes & seller has put back their own furnishings

20 Ridgeway RD, Hillsborough

Listed by Mark Palermo, 650-218-6400 from Compass
(If provided) CoList: Irina Luck from Compass

Sold listing courtesy of Ranya Kaileh Francis from SIR

$8,250,000
6 Beds 7 Baths ML81985068 MLS
Once in a very great while, a magical opportunity presents itself. Nestled in the Lakeview canyons, the Secret Garden Sanctuary is the special home you have been searching for. Built in 2008, and situated on a nearly flat one-half acre plus parcel, the almost 5,000 square foot English Tudor inspired home has been lovingly maintained and upgraded over the years by an artist and interior designer. Complementing the main residence is a charming 300-square-foot ADU cottage which mirrors the timeless elegance of the primary home. Wake up to birds chirping on the veranda off the primary suite as you remotely turn on the jets of the in-ground jetted pool. Enjoy a steam shower in the full slab natural stone shower, followed by a breakfast prepared in the chefs kitchen using fresh ingredients harvested from your own garden and eggs gathered from the chicken coop. Meditate over the soothing sound of the natural stone fountain. Wander through your garden to prepare for a focused day of work in the large and sunny office or relax into the evening in front of the hearth, contemplating the hand painted ceilings of the dining room after dinner with a glass of wine. This house is truly special, hidden in the hills, among a community of caring Hillsborough neighbors. Your sanctuary awaits.

70 Joyce RD, Hillsborough

Listed by Bill McQuaid, 650-245-1605 from Compass
(If provided) CoList: The Cheung Group from Compass

Sold listing courtesy of Hira Bakhsh from SFLT01

$4,888,888
5 Beds 6 Baths ML81993303 MLS
REDUCED ALMOST $2M FROM ORIGINAL LITSING PRICE. HOUSE BUILT 2005 BY WELL KNOWN CONTRACTOR RON GALI FOR THE CURRENT OWNER. BEST DEAL! WON'T LAST! Nestled on a gated, OVER 1/2 ACRE flat corner lot in a private cul-de-sac. This Mediterranean-style estate combines timeless elegance w/ modern comfort. The beautifully paved brick driveway enhances its grandeur. Inside, the grand foyer, w/ a winding staircase & clerestory window, exudes sophistication and fills the space with natural light. Hardwood flooring, tray ceilings, & recessed lighting are found throughout. The formal living and dining rooms feature elegant touches like a fireplace, arched windows & doorways, and a tray ceiling with cove lighting. The great room includes a cozy family room with built-in cabinetry, a circular breakfast nook, and a chef's kitchen with ALL HIGH-END APPLIANCES, granite countertops, a center island, and a butler's pantry. The first floor also offers an office, a mudroom, & en-suite guestroom. Upstairs, the primary suite boasts a private balcony, spa-like bathroom, Bay Views, & walk-in closet. 3 additional en-suite bedrooms, one w/ a private balcony, & a study nook complete the second floor. Outside, a serene patio surrounded by trees offers a perfect space. Luxury, functionality, & timeless beauty.

1 Scott CT, Hillsborough

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

Sold listing courtesy of DonnaMarie Baldwin from APR

$6,600,000
5 Beds 6 Baths ML81983440 MLS
Contemporary located at the end of a private cul-de-sac. Soaring ceilings, walls of glass, and voluminous rooms. Exotic Balinese pool area with private bath and dressing area welcomes you to this exquisite home. Kitchen updates feature granite and quartz countertops, Viking 6-burner gas cooktop, Miele oven, unique steam oven, built-in Thermador refrigerator, 2 separate stainless steel sinks. Upgraded sliding doors and stone decking. Some rooms have electric shades to cover very large windows. All baths have Toto toilets. Nest thermostats on each level. Cathedral ceilings. Sound system recently upraded and installed throughout. Screen in media room is 160". Indoor laundry room features 2 sets of washers & dryers; Bosch & Maxima. 500 bottle wine cellar, built-in wet bar, 3-car garage.

840 Lombardi LN, Hillsborough

Listed by Patrice Carper, 408-421-9976 from Compass
(If provided) CoList: from

Sold listing courtesy of Stanley Lo from GRBA

$8,000,000
6 Beds 8 Baths ML81980486 MLS
This Hillsborough estate is a true masterpiece of contemporary design and craftsmanship. Nearly 5,700 sf of total living space. Spanning three levels, the home is filled with exquisite details and premium materials, with a bold use of glass that floods every corner with natural light. A magnificent great room, a gourmet kitchen, and an inviting family room provide ideal venues for both entertaining and daily life. Designed for seamless indoor/outdoor living, glass walls fully retract to reveal five-star grounds with an infinity pool, an outdoor kitchen, and patio space. Each bedroom is en suite, with the stunning primary suite boasting a fireplace and a private balcony, while the detached guest home provides an additional bedroom and bathroom. Conveniently close to downtown Burlingame, a prestigious country club, parks, SFO, and commute options. Additionally, families will appreciate access to top-rated public schools and nearby private institutions (buyer to verify eligibility).

1225 La Cumbre RD, Hillsborough

Listed by DeLeon Team, 650-543-8501 from Deleon Realty
(If provided) CoList: from

Sold listing courtesy of James Koh from COMP

$7,108,000
5 Beds 5 Baths ML81980363 MLS
Regally situated on a .59-acre lot with breathtaking Bay views, this stunning +/-5,000 sq. ft. residence offers 5 bedrooms and 4.5 baths, blending luxury and warmth in a seamless, sun-drenched floor plan. Highlights include an impressive living room with floor-to-ceiling windows that frame the incredible views and French doors that open to the exceptional rear grounds, a large formal dining room, chefs kitchen/family room ensemble with island and breakfast nook, and French doors that access a vast terrace and the amazing grounds. 3 bright bedrooms with 2 bathrooms plus 2 powder rooms complete one wing of the main level. Upstairs features a sizable primary bedroom retreat with wall-to-wall windows that capture spectacular views, built-in cabinets, fireplace, 2 walk-in closets, spa-like marble bath, and a laundry closet. The substantial 5th bedroom wing includes a great room, full bath, rear patio access, lower-level gym/office, and large wine room--the perfect place for guests or recreation. Outside, the majestic grounds offer elegant & lush landscaping, meandering pathways, incredible vistas, large patios, outdoor kitchen, firepit, sweeping level lawns, fountain, rose garden, and a putting green. Completing this showcase home is an attached 3-car garage and a large laundry room.

25 Longview CT, Hillsborough

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

Sold listing courtesy of Sisi Huang from KWPEN

$6,000,050
5 Beds 4 Baths ML81970557 MLS
Discover the epitome of California living in this serene mid-century style home, situated on a mostly level .85-acre lot in one of Hillsborough's most desirable streets. This single-level residence offers a seamless indoor-outdoor flow, accentuated by high ceilings and walls of glass. A spacious formal entry introduces this bright & airy home opening to the formal rooms and a conveniently located powder room. Enjoy gatherings in the dramatic living room, host formal dinners in the separate dining room or relax in the comfortable family room bordering an inner courtyard patio. Hardwood floors grace the common areas, complementing the remodeled eat-in kitchen equipped with a Thermador suite of appliances, including a 6-burner range with griddle. A sizable office featuring a fireplace and access to the backyard, a bright primary suite with a large walk-in closet and 3 spacious and sunny bedrooms emanate off this central hallway with 2 of the bedrooms joined by a shared large bathroom. The 5th bedroom suite is off the kitchen by the second entry. Step outside from multiple locations to the lush grounds featuring sunny gardens, mature fruit trees and a sparkling swimming pool. Additional amenities include gated entry, 2-car garage with EV charger, abundant separate storage areas.

745 Bromfield RD, Hillsborough

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

Sold listing courtesy of Geoffrey Nelson from CBR

$5,350,000
5 Beds 3 Baths ML81964204 MLS
THIS is HOME! Beautifully located, this extraordinary home showcases elegance and charm. A gorgeous architectural gem that shines for casual living and elegant entertaining. The quality of classic design is immediately evident in the handcrafted woodwork, high ceilings, and divided light windows, all graced with the finest details. Living areas flow in a welcoming configuration around the elegant entry leading to a richly detailed living room, gracious formal dining room and culinary eat-in kitchen with adjoining family room that naturally extends to the sensational yard. Mature landscaping frames the home on a lot measuring.72 acre with resort inspired tranquility, vast lawn areas, tennis court and fountain courtyard perfect for outdoor relaxation and entertaining. A coveted neighborhood, close to exceptional schools, shopping, dining, recreation, convenient commute routes to San Francisco, SFO and Silicon Valley makes this one-of-a-kind property a guaranteed wonderful home! County records show 3080 sq ft., Appraisals and Floor Plan Visuals show over 3500 sq ft

315 Arden RD, Hillsborough

Listed by The Patty Dwyer Group, 650.796.3039 from Compass
(If provided) CoList: from

Sold listing courtesy of Shaun Walter from CBR

$4,911,000
4 Beds 4 Baths ML81961341 MLS
Nestled in the serene neighborhood of Hillsborough, 575 Darrell Road is a testament to modern luxury living. This meticulously crafted residence boasts 2918 square feet of exquisite living space, featuring 4 bedrooms and 3.5 bathrooms, perfectly tailored to accommodate the needs of a discerning homeowner. Notably, this home underwent extensive remodeling in 2016, including a thoughtful addition to the square footage, ensuring it seamlessly blends contemporary amenities with timeless charm. Every detail, from the upgraded fixtures to the modern conveniences, reflects the utmost attention to quality and craftsmanship, but the allure of 575 Darrell Road extends beyond its interiors. Step outside into the meticulously manicured backyard, and you'll discover a true oasis designed for outdoor entertaining. From the spacious patio area perfect for al fresco dining to the lush green lawn ideal for children's play, every corner of this outdoor sanctuary lets you relax and unwind in style.

575 Darrell RD, Hillsborough

Listed by The Laugesen Team, (650) 642-5399 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of The Laugesen Team from KWPEN

$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

$11,500,000
6 Beds 8 Baths ML81956058 MLS
RARE PRIVATE SHOWCASE IN LOWER HILLSBOROUGH! TURN-KEY INTERIOR WITH SOME MODERN UPDATES THROUGHOUT! HUGE 1 FLAT ACRE LOT* WITH A LARGE GRASSY FIELD, sparkling pool, fire pits, garden walkways, and several patio areas; perfect for the whole family as well as hosting loved ones. Prestigious Ryan Tract neighborhood w/ an abundance of lush GREENERY for LOTS OF PRIVACY. FIRST TIME ON THE MARKET! Ideal open floor plan which features high ceilings, 2 high end chef's kitchens w/ top-of-the-line appliances, oversized living room, additional family room, custom built office/study, wine cellar, fitness room, mudroom, AND SO MUCH MORE! Stylish hallways, a grand staircase, and 2 majestic large white columns give a sense of grandeur & opulence. Extra large balconies wrap around the exterior overlooking the park-like yard. Multiple extravagant en-suite rooms & spa-like bathrooms make this home feel like a resort. Be able to walk to Downtown Burlingame and enjoy access to some of the best schools Northern California has to offer. DON'T WAIT!

1904 Forest View AVE, Hillsborough

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

Sold listing courtesy of Kim Gelman from CBR

$6,668,000
5 Beds 7 Baths ML81955202 MLS
Lush Italian Villa sits on .68 acre lot in the heart of Hillsborough. This five bedroom, six and a half bath home is the perfect blend of masterful craftsmanship and modern amenities. The main level includes a formal living room, dining room, large family room and chefs kitchen with adjoining butlers pantry. With 4 sets of French doors opening from the main floor living spaces to the backyard, this home boasts the ultimate indoor/outdoor lifestyle. Rounding out the main floor are two bedrooms and two and a half baths, complete with a timeless moody wood-paneled office. Upper floor features three bedroom suites, including the sumptuous double door primary suite with a private sun soaked balcony. Lower Level includes a multi-use rec room, walk-in wine storage with over 1200 bottle capacity, full bathroom, ample storage spaces and an oversized balcony overlooking the landscape. The multi-level yard is the perfect blend of mature landscaping and hardscape, with a four-hole putting green and an abundance of varietal fruit and flowering trees. Additional highlights include tray and coffered ceilings, two fireplaces, and a 3 car garage (EV ready) with spacious built-ins. A true oasis tucked into the hills.

1285 La Cumbre RD, 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 The Patty Dwyer Group from APR

$4,600,000
4 Beds 4 Baths ML81954511 MLS
Nestled within the prestigious Sky Farm area of Hillsborough, this remarkable uniquely situated residence on the corner of a serene cul-de-sac, offers both tranquility and easy access to highway for easy commute to both San Francisco and Silicon Valley. It boasts unobstructed panoramic views of the Bay from all three ensuite bedrooms, living room, dining room and the front garden and patio for al fresco lounging to enjoy this magnificent setting!! This home features: Beautifully remodeled chef's kitchen with amazing custom cabinets featuring beveled glass. Family room and breakfast nook extend to a spacious patio for outdoor lounging and dining, overlooking the recently upgraded pool and beautifully landscaped terraced backyard. Attached au pair suite/office, adjacent to kitchen, garage and laundry closet, has a separate entrance and a full bathroom. The property also boasts a substantial 675 sq ft +/- three-car garage. Additional secure parking within the property accessed through an automatic gate. Conveniently located in close proximity to award-winning Hillsborough schools and the sought-after Nueva School. This property seamlessly combines accessibility with the serenity of its surroundings, making it a true gem in the Bay Area.

10 Silk Tree PL, Hillsborough

Listed by Parnian Kaboli, 650-224-5943 from Compass
(If provided) CoList: from

Sold listing courtesy of The Patty Dwyer Group from APR

$6,300,000
5 Beds 6 Baths ML81952078 MLS
Elegance abounds in this original William Wurster design that was expanded and restored to perfection by renowned local architect Farro Essalat. Tucked away on approximately .73 acres of outstanding verdant grounds, 989 Hayne Road is a rare gem that is to be cherished for generations to come. Every feature of this five bedroom, five and one-half bath home offers the highest level of design, impeccable attention to detail, and masterful craftsmanship. The welcoming foyer with beautiful curved staircase is a fitting prelude to the grandly-proportioned interior spaces, which include a library, billiard room, huge family room and mud room. The delightful flow of this exceptional home extends to the incredibly-manicured grounds, offering beautiful planter beds, tranquil garden pathways, a rose garden, fire pit, superb outdoor kitchen, and spa with Bay views. This magnificent estate presents a unique opportunity for the discerning owner seeking that special, one-of-a-kind property.

989 Hayne RD, Hillsborough

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

Sold listing courtesy of Jim Arbeed from CBR

$5,838,800
4 Beds 5 Baths ML81945870 MLS
Escape to this stunning 4BD/4.5BA cul-de-sac retreat in the sought-after Carolands neighborhood of Hillsborough! Custom-built by the owners in 2007, this idyllic home offers 4 en suites, office, and hobby room. Surrounded by a natural park-like setting by landscape architect Michael Callan, admire lush gardens, fruit trees and the meditative sound of the fountain. Culinary delights await in the kitchen with BlueStar gas cooktop and Sub-Zero refrigerator. The formal living and dining rooms are perfect for elegant dinner parties, while the surround sound sets the ambiance for entertainment. Retreat to the spacious primary bedroom to unwind in the spa-like bathroom with jetted tub and steam room shower. This remarkable home includes 3-zone HVAC, Hunter Douglas shades, Anderson dual-paned windows, and slate roofing with copper gutters. With top schools & proximity to 280, this home offers the perfect blend of luxury and convenience. Experience this storybook estate firsthand. Welcome home!

625 Barbara WAY, Hillsborough

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

Sold listing courtesy of Laura Lee from APR

$4,500,000
3 Beds 3 Baths ML81941240 MLS
Situated in an idyllic setting on a private & gated .54-acre lot, this sprawling single-level home merges timeless elegance with modern amenities in over 2,800s.f. of living space. Offering 3 bedrooms & 2.5 baths, the graceful interior unfolds with a grand marble foyer that opens to the stunning living room with cathedral ceiling, huge floor-to-ceiling windows that frame the incredible rear grounds, and the adjoining dining room with fireplace and built-in display case. The chefs kitchen, with high-end appliances, center island with prep sink, and breakfast nook, opens to the family room with fireplace, wet bar, and direct access to the amazing yard. 3 sizeable bedrooms, including the primary suite with spa-like bath, are situated in a private wing, while the public rooms, half bath, mud room and 2-car attached garage comprise the other wing. The expansive grounds with level lawns, lush landscaping, pool, and huge, covered entertaining patio, offer the best of indoor/outdoor living.

860 Hayne RD, Hillsborough

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

Sold listing courtesy of Pierre Buljan from APR

$11,750,000
5 Beds 9 Baths ML81934280 MLS
Regally set on 2.8 glorious acres on iconic Robin Road, this custom built estate has a total 10,400 Square feet of luxurious living area. This home is like NEW. Seldom used by owners. Industrial quality construction top to bottom. Priced millions below replacement cost. Inside are 5 bedroom suites including a huge primary suite with 2 bathrooms, and 2 walk-in closets. Additional rooms include a baronial scaled foyer, grand living and dining rooms, separate music room, family room, media room, professional kitchen and breakfast room, all opening onto limestone terraces, the manicured grounds and gardens, sunny pool and tennis court, plus the original Redwood Grove from the Carolands estate. Reached through a Porte Cachere, is a 4 car garage and massive motor court.. Built for the owners as the Ultimate dream home, no expense was spared, no detail overlooked in creating this amazing home that, by any definition, is world class. To view this home is an experience one will never forget.

195 Robin RD, Hillsborough

Listed by Edward Stephens, 650-208-1301 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jim Arbeed from CBR

$11,680,000
5 Beds 6 Baths ML81926309 MLS
This opulent estate in the Carolands area spans 2 acres. The grand foyer leads you to a light-filled formal living room complete with high ceilings and a fireplace. The gourmet kitchen will help you prepare for hosting luncheons and dinners in the elegant banquet room. Afterwards, you could proceed to the salon to unwind with cocktails and games. Move between floors in your very own elevator, use the wine cellar to store your collection, and set up to work remotely in the library. Relax during the afternoon or evening in one of the many spacious bedroom suites. The backyard includes a playground area and 1 bedroom guest house with lanai to live it up during the warmer seasons. Matured gardens make for delightful outdoor lounging or entertaining - enjoy the pool & spa or organize a tennis match with friends. Parking is plentiful with a 4 car garage and the expansive driveway prominently features a stately fountain.

3300 Ralston AVE, Hillsborough

Listed by Mary Bee, 650-343-9999 from RE/MAX Star Properties
(If provided) CoList: from

Sold listing courtesy of Mary Bee from RMXSP

board logoThe 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.


Copyright 2026 MLSListings Inc. All rights reserved