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200 Darrell RD, Hillsborough
$5,488,000
5 Beds ⋅ 5 Baths ⋅ ML82066167 MLS
Bay views and tucked behind mature landscaping on a private, tree-lined lot, this home offers a rare combination of classic elegance and resort-style outdoor living - all in one of the Peninsula's most coveted addresses. Inside, freshly painted, sun-filled principal rooms with newly refinished hardwood floors are designed for both everyday living and effortless entertaining: a gracious foyer opens to a formal Living Room with fireplace, an equally elegant Dining Room, and a Family Room anchored by its own fireplace and walk-out access to a private deck. The updated kitchen flows seamlessly into a sunny entertaining area. Upstairs, the primary suite is a true retreat, with a spa-inspired bath featuring a soaking tub and heated floors. Three additional bedrooms and an office complete the second floor. A lower-level room with wet bar and an additional bedroom offer flexible space for guests, media, or play. Outside, the grounds are spectacular - a sport court, batting cage, outdoor kitchen, fire pit, and sprawling lawn create an entertainer's paradise, all framed by newly refreshed landscaping. Perfectly located in Hillsborough, minutes to top-rated schools, downtown Burlingame, Highway 280, San Francisco and Silicon Valley, this is the Peninsula lifestyle at its finest.

200 Darrell RD, Hillsborough

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

501 El Cerrito AVE, Hillsborough
$8,314,900
5 Beds ⋅ 5 Baths ⋅ ML82064709 MLS
Set behind private gates in coveted Lower Hillsborough, this French-inspired estate blends timeless architecture with gracious spaces for everyday living and entertaining. A slate roof and architectural details introduce the home, while a grand entry with a sweeping curved staircase creates a memorable arrival. Elegant formal living and dining rooms are complemented by four fireplaces and an inviting library with custom built-in shelving. The kitchen features a Wolf range and opens to the spacious family room, creating a comfortable gathering place at the heart of the home. Soaring ceilings, Caribbean pine flooring, and travertine finishes add warmth and character throughout. The expansive primary suite offers a peaceful retreat with a soaking tub and appointed bath. Outside, landscaped grounds provide inviting spaces for relaxation and entertaining, with the gentle sounds of nearby San Mateo Creek creating a tranquil natural backdrop. Ideally located just minutes from the downtowns of Burlingame and San Mateo, with their dining, boutique shopping, and entertainment, the property offers easy access to excellent schools, major commute routes, San Francisco, and Silicon Valley. A rare opportunity to experience refined living in one of the Peninsula's most desirable neighborhoods.

501 El Cerrito AVE, Hillsborough

Listed by Ranya Kaileh Francis, 415-722-5115 from Sotheby's Intl Rlty
(If provided) CoList: Haifa Khoury from Sotheby's Intl Rlty

Sold listing courtesy of Jim Arbeed from CBR
40 Eugenia WAY, Hillsborough
$6,175,000
5 Beds ⋅ 5 Baths ⋅ ML82061953 MLS
Commanding a 0.721-acre promontory in Hillsboroughs coveted Skyfarm neighborhood, this exceptional five-bedroom, five-bathroom residence is defined by scale, privacy, and an intimate connection to the landscape. Framed by breathtaking, unobstructed canyon views, the property delivers a private resort experience right at home, complete with a crystal-clear pool set against sweeping natural vistas. Designed for both grand entertaining and effortless daily living, the generous floor plan features a custom wine room and a convenient elevator, offering exceptional comfort, privacy, and seamless indoor-outdoor flow. Exceptional storage and vehicle accommodation abound with an oversized 4-car garage, ideal for car enthusiasts, extra storage, or potential workshop space. Situated on premier grounds in one of Northern Californias most coveted enclaves, this residence seamlessly unites architectural scale, ultimate privacy, and an idyllic natural setting. Offering access to Hillsboroughs top-rated public schools, the home stands as a refined expression of contemporary California luxury where architecture, landscape, and everyday life harmoniously converge high above the canyon.

40 Eugenia WAY, Hillsborough

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

Sold listing courtesy of Jenn Gilson from MCGR
860 Longview RD, Hillsborough
$6,150,000
5 Beds ⋅ 5 Baths ⋅ ML82060425 MLS
Set against stunning Bay views, this Ranch style home blends timeless mid-century modern character with spacious, light filled living. Approximately 4,560 square feet of living space offers five bedrooms and four-and-a-half baths, with an inviting combination of formal and informal rooms. The main bedroom wing is thoughtfully arranged with a spacious primary suite, plus two additional bedrooms connected by a bathroom. A guest suite is conveniently located off the kitchen and laundry area, while the lower level -- with its own exterior access offers a potential fifth bedroom and full bath. The lower level provides even more flexibility, with an additional room perfect for an office, second family room or game room. Abundant natural light fills the home, while expansive windows capture the spectacular Bay outlook and create a strong connection to the private, mostly level grounds. The formal dining room and family room both have access to the backyard with a swimming pool and generous outdoor spaces. Architectural character, generous scale, versatile living spaces, privacy, and breathtaking views all paired with top-rated public schools. Perfect Mid-Peninsula location.

860 Longview RD, Hillsborough

Listed by The Dwyer Group, 650-759-1593 from Compass
(If provided) CoList: from

Sold listing courtesy of Heather Hansen from APR
2801 Easton DR, Hillsborough
$7,100,000
4 Beds ⋅ 5 Baths ⋅ ML82058766 MLS
Set in coveted lower North Hillsborough, 2801 Easton Drive offers timeless French Country character in a prime location just moments from downtown Brodaway Burlingame. This gracious home blends classic architectural appeal with an inviting sense of warmth and sophistication, creating an exceptional opportunity in one of the Peninsulas most desirable neighborhoods. Enjoy the convenience of being within walking distance of downtown Broadway Burlingames acclaimed shops, restaurants, cafés and everyday amenities, while nearby parks and neighborhood streets provide a peaceful residential setting. The property is located in the North Elementary, Crocker Middle Schools, and Burlingame High School attendance areas. A rare combination of distinctive style, sought-after location and exceptional walkability. 2801 Easton Drive embodies the best of Lower North Hillsborough living.

2801 Easton DR, Hillsborough

Listed by Max Lo, 650-307-8816 from Green Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jason Liu from FQLT
19 Farm LN, Hillsborough
$10,300,000
6 Beds ⋅ 5 Baths ⋅ ML82057038 MLS
Located in one of Hillsborough's most coveted neighborhoods, 19 Farm Lane is an exceptional residence set along tree-lined streets amid extraordinary privacy & beautifully manicured grounds. Flowering plants, mature landscaping, & a massive flat lot create an impressive sense of arrival, complemented by an expansive driveway & 3-car garage. Inside, large windows, high ceilings, skylights, & recessed lighting create an airy, light-filled atmosphere. The thoughtfully designed floor plan offers effortless everyday living & entertaining, with a well-equipped kitchen, formal dining room, & generous living spaces. The lower level features a spacious living room & family room, two en-suite bedrooms with walk-in closets, & an additional bedroom ideal for guests or extended living. Upstairs, the luxurious primary suite offers two walk-in closets & a spa-like bathroom. Outside, the expansive backyard is a private sanctuary surrounded by lush landscaping & centered around a sparkling pool. Just minutes by bike from Downtown Burlingame's shops & restaurants, the home also offers access to some of California's finest schools. With its exceptional setting, privacy, flat lot, pool, and versatile floor plan, 19 Farm Lane presents a rare opportunity to experience the best of Hillsborough living.

19 Farm LN, Hillsborough

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

Sold listing courtesy of Michele Oravec from APR
2245 Oakdale RD, Hillsborough
$7,600,000
5 Beds ⋅ 5 Baths ⋅ ML82054472 MLS
Nestled on a nearly 19,255 square foot lot in coveted Lower North Hillsborough, this inviting residence offers exceptional privacy and an effortless Peninsula lifestyle. Fresh, comfortable, and move-in ready, the home is designed for primarily single-level living with four bedrooms, an office, and four full baths on the main level. Nearly every room opens to the spectacular backyard, while walls of glass fill the home with natural light and create a seamless connection to the resort-inspired grounds. The backyard is the heart of the home. Enjoy sunny afternoons by the sparkling pool, entertain on expansive patios, or watch children play on the sprawling level lawn below, reminiscent of a private playing field. A separate lower level with its own entrance includes a bedroom, full bath, and spacious family roomideal for an au pair, extended family, guests, a home gym, or a private retreat. Lovingly maintained, including an updated heating system, this is a rare opportunity to own a timeless Hillsborough home where privacy, comfort, and exceptional indoor-outdoor living come together.

2245 Oakdale RD, Hillsborough

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

Sold listing courtesy of Sandra Comaroto from APR
1850 Brookvale RD, Hillsborough
$10,500,000
5 Beds ⋅ 5 Baths ⋅ ML82053151 MLS
Gracefully tucked behind private gates in Lower Hillsborough's premier location, this exceptional contemporary residence offers a rare blend of privacy, sophistication, and effortless indoor-outdoor living. Directly across from the lush fairways of Burlingame Country Club, the home enjoys expansive green views, a majestic redwood grove, and a serene connection to nature. Designed for both relaxed everyday living and elegant entertaining, the residence features five bedrooms, four-and-one-half bathrooms, and light-filled living spaces. Expansive glass doors create a seamless connection to the landscaped grounds, where mature gardens, multiple outdoor entertaining areas, and a sparkling pool create a resort-like retreat. The thoughtfully designed single-level floor plan includes formal and informal living spaces, a spacious family room, and a well-appointed chef's kitchen, all designed for comfort and seamless living. Located moments from Burlingame Avenue, top-rated Hillsborough schools, San Francisco International Airport, and Silicon Valley, this exceptional residence offers an extraordinary Peninsula lifestyle.

1850 Brookvale RD, Hillsborough

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

Sold listing courtesy of Raziel A. Ungar from APR
1050 Merner RD, Hillsborough
$3,250,000
4 Beds ⋅ 5 Baths ⋅ ML82048490 MLS
Tucked along a private paved brick lane just off coveted Crystal Springs Road, 1050 Merner is a serene retreat surrounded by mature trees and lush landscaping. Offering 4 bedrooms main plus a 1-bedroom ADU, the home is filled with natural light and features recessed lighting throughout, creating a warm and inviting atmosphere. Designed for both comfortable living and effortless entertaining, the outdoor spaces are equally impressive. The expansive wood patio provides the perfect setting for al fresco dining and gatherings beneath the trees, while stairs lead down to a secondary yard complete with a playground and sandbox, creating endless opportunities for recreation and relaxation. Inside, the spacious primary suite offers a relaxing escape with a walk-in closet and beautifully appointed en-suite bath. The versatile ADU and separate studio/office provide exceptional flexibility for guests, a gym, creative workspace, or au pair quarters. A two-car garage offers ample storage and convenient parking. Ideally located with easy access to Alameda de las Pulgas, Highways 92 and 280, and just minutes from both downtown San Mateo and downtown Burlingame, this property combines privacy, functionality, and convenience in one exceptional offering.

1050 Merner RD, 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
1955 Parkside AVE, Hillsborough
$7,825,000
4 Beds ⋅ 5 Baths ⋅ ML82046534 MLS
For the first time in over half a century, this remarkable family estate is opening its doors to a new chapter. Built in 1967 and held by the same family ever since, this is more than just a homeit is a rare opportunity to acquire a residence of incredible character and complete seclusion. The expansive floor plan is thoughtfully designed for both grand entertaining and intimate daily life, featuring four generous bedrooms along with three full and two half baths. Among its many refined living spaces is a sophisticated library, offering the perfect sanctuary for a home office or quiet reflection. Every room is bathed in natural light, creating a seamless connection between the interior and the breathtaking grounds outside. Set within a lush, private envelope, the property is defined by stunning curated gardens that create a verdant oasis. These meticulously maintained outdoor spaces provide a level of privacy that is increasingly rare, ensuring a serene retreat. Meticulously cared for and brimming with potential, this is a once-in-a-generation opportunity to acquire this remarkable estate and steward its beautiful legacy into a new era.

1955 Parkside AVE, Hillsborough

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

Sold listing courtesy of Jenny MacLeod from APR
260 Robin RD, Hillsborough
$5,795,000
4 Beds ⋅ 5 Baths ⋅ ML82037384 MLS
Occupying a premier setting in one of Hillsboroughs most prestigious enclaves, 260 Robin Road showcases exceptional craftsmanship and timeless design. This completely rebuilt estate offers over 3,800 square feet of refined living space, blending modern luxury with effortless livability. Designed for todays discerning buyer, the home features four luxurious bedroom suites and five beautifully appointed bathrooms, each finished with thoughtful attention to detail. Expansive living spaces and walls of glass frame breathtaking Bay views while filling the home with natural light and creating a seamless connection between indoor and outdoor living. The open kitchen and family room serve as the heart of the home, designed for both everyday comfort and elegant entertaining. Set on a rare two-acre lot, the property offers an extraordinary sense of privacy and scale. A flat, fenced yard provides exceptional usable space for recreation, entertaining, or future amenities. With its elevated setting, stunning views, and beautifully rebuilt interiors, 260 Robin Road represents a rare opportunity to own a truly special Hillsborough estate.

260 Robin RD, Hillsborough

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

Sold listing courtesy of Stanley Lo from GRBA
20 Denham CT, Hillsborough
$12,500,000
5 Beds ⋅ 5 Baths ⋅ ML82045292 MLS

20 Denham CT, Hillsborough

Listed by Max Lo, 650-307-8816 from Green Banker Realty
(If provided) CoList: from

Sold listing courtesy of Max Lo from GRBA
300 Uplands DR, Hillsborough
$7,172,500
5 Beds ⋅ 5 Baths ⋅ ML82044375 MLS
Located in prime Lower South Hillsborough, this beautifully updated home sits on approximately 0.42 acres of flat, private, and meticulously landscaped grounds designed for effortless indoor-outdoor living. The front yard features manicured turf and a putting green, while the backyard offers a resort-like setting with a pool, built-in BBQ, outdoor TV, and multiple entertaining areas. Light-filled interiors showcase a seamless flow with a spacious kitchen/family room combination and formal living and dining rooms, all oriented toward the backyard. A rare highlight is the presence of two primary suites, providing exceptional flexibility. The upstairs primary retreat features dual closets, a private deck overlooking the pool, a spa-like bath with soaking tub, dual sinks, and high ceilings, plus an attached office with built-ins. A nursery is conveniently located adjacent to this suite. A second primary suite is located on the main level and overlooking the backyard. Alongside, is 2 additional bedroom suites, offering comfort and privacy for family and guests. Ideally located, mere blocks from Crystal Springs Uplands School, South Elementary, The Episcopal Day School, and just minutes to downtown San Mateo.

300 Uplands DR, Hillsborough

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

Sold listing courtesy of Max Lo from GRBA
1510 Kingswood DR, Hillsborough
$5,900,000
4 Beds ⋅ 5 Baths ⋅ ML82043528 MLS
A MUST SEE, BEST OF THE BEST! Set on a flat, park-like half-acre lot, this beautifully renovated and expanded single-story home blends timeless elegance with modern functionality. A circular paver driveway leads to a covered front porch while also extending to a spacious motor court, providing access to a side-entry three-car garage with 2 Tesla EV chargers. Inside, hardwood floors and recessed lighting enhance a thoughtfully designed layout. A formal living room with a dual-sided fireplace--shared with the family room--flows into the formal dining area. The updated chef's kitchen features quartz countertops, a large island, stainless-steel appliances, abundant cabinetry, and a breakfast nook with a nearby powder room. French doors in the family room open to an expansive patio for seamless indoor-outdoor living. The private wing offers four bedrooms and four updated baths, including a luxurious primary suite with backyard access, dual walk-in closets, & a spa-like bath with soaking tub and glass shower. Grounds include turf lawns, a studio with kitchenette and powder room, a deck, and a pickleball court beneath a sport surface. Solar panels and a Tesla Powerwall add efficiency. 1510 Kingswood Dr represents the very best of Hillsborough living. Don't miss this turnkey masterpiece.

1510 Kingswood DR, Hillsborough

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

Sold listing courtesy of DeLeon Team from DLRPA
755 Bromfield RD, Hillsborough
$6,700,000
4 Beds ⋅ 5 Baths ⋅ ML82043371 MLS
Elegant transitional Colonial in sought-after lower Hillsborough, set on a private, tree-lined lot. Light-filled interiors with garden views throughout. Kitchen with Carrera marble and Thermador appliances flows into gracious, defined living and dining spaces. La Cantina folding doors open to a resort-style backyard with built-in BBQ, firepit, and multiple entertaining areas. Renovated in 2020 with French oak floors, all new Marvin windows, and updated finishes throughout. Four bedrooms upstairs, including two spacious primary suites. Private, serene setting just moments from North School, Crocker Middle School, and Burlingame Avenues shops and dining

755 Bromfield RD, Hillsborough

Listed by Max Lo, 650-307-8816 from Green Banker Realty
(If provided) CoList: from

Sold listing courtesy of The Sharp Group from KWPEN
10 Salmark CT, Hillsborough
$5,500,000
5 Beds ⋅ 5 Baths ⋅ ML82042651 MLS
Privately set on a serene cul-de-sac, this gated estate is a refined expression of scale, light, and California indoor-outdoor living. A circular drive introduces a grand entry and sweeping staircase, with soaring ceilings elevating the formal living and dining spaces. At the heart of the home, a crisp white chefs kitchen flows effortlessly into the family room and out to curated gardens and expansive decks, mature trees, and a grassy play space, designed for effortless entertaining. Each of the 4 upstairs bedrooms opens to a balcony, while the primary suite unfolds as a true retreat complete with wraparound canyon views, a dressing area, and a spa-inspired bath. Don't miss this rare offering defined by privacy, elegance, and award-winning Hillsborough schools.

10 Salmark CT, Hillsborough

Listed by Hope Pilch, 650-619-4732 from HP Properties
(If provided) CoList: from

Sold listing courtesy of Jingya Ji from CBR
1162 Barroilhet DR, Hillsborough
$6,000,000
4 Beds ⋅ 5 Baths ⋅ ML82042279 MLS

1162 Barroilhet DR, Hillsborough

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

Sold listing courtesy of The Laugesen Team from KWPEN
1340 View Haven RD, Hillsborough
$4,750,000
5 Beds ⋅ 5 Baths ⋅ ML82041555 MLS
Commanding sweeping views of San Francisco, the Bay Bridge, and a glittering skyline, 1340 View Haven is a contemporary Hillsborough retreat designed to showcase its extraordinary vantage point. A private tree lined setting, the home unfolds through a dramatic double-height foyer with a glass-encased staircase and suspended artistic wine display. The house unfolds to expansive, light-filled living areas framed by walls of glass blurring the line between indoors and out. A sleek, European-style kitchen is anchored by a sculptural quartz island and premium appliancesseamlessly flows into dining and family areas, all opening to view terraces designed for elevated entertaining. The house has five bedrooms with a stunning primary bedroom retreat with panoramic outlooks, private balcony, fireplace, and spa-like bath. Outside, a view-facing pool and spa, fire pit, and heated terraces create a space for year round enjoyment. Recent structural enhancements include retrofitting to the deck, foundation, and retaining walls, reinforcing both integrity and longevity.

1340 View Haven RD, Hillsborough

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

Sold listing courtesy of Candace Stadelmann from APR
730 Hillsborough BLVD, Hillsborough
$8,000,000
5 Beds ⋅ 5 Baths ⋅ ML82036808 MLS
Situated in Lower North Hillsborough, this gated property encompasses approximately 30,348 square feet flat lot and represents a rare estate-caliber parcel for the discerning buyer. Mature landscaping, privacy, and abundant sun exposure define the setting, just moments from downtown San Mateo, Burlingame Avenues shopping and dining, and top-rated Hillsborough schools. The expansive grounds feature broad lawn areas, a sparkling pool and cabana, detached guest house, greenhouse, two-car garage, enclosed carport, and circular drive, creating a substantial footprint across the site. The existing residence, including a 1997 addition, is approximately 5,533 square feet, offers generous scale and presents an opportunity for significant renovation, reconfiguration, or potential redevelopment. See floor plans for details. Large, flat lot of this size are increasingly scarce in Lower North Hillsborough, providing the opportunity to create a customized estate in one of the Peninsulas most desirable neighborhoods with enduring long-term value.

730 Hillsborough BLVD, Hillsborough

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

Sold listing courtesy of Alex Hawkins from CRNAN
2323 Summit DR, Hillsborough
$5,628,000
5 Beds ⋅ 5 Baths ⋅ ML82036647 MLS
Classic elegance and timeless character define this exceptional three-level Mission Spanishstyle estate set on approximately 0.48 acres in sought-after Lower North Hillsborough. Rich in architectural charm, the home welcomes you with a grand entry hall and sweeping staircase leading to expansive living spaces designed for both refined entertaining and comfortable everyday living. The impressive living room features a dramatic high beamed ceiling and fireplace, while the living and formal dining rooms open to a covered porch capturing filtered Bay views. The formal dining room accommodates large gatherings and flows seamlessly into a gourmet eat-in kitchen with island and top-of-the-line appliances. A main-level bedroom and full bath offer flexibility for guests or extended family. Upstairs are three spacious bedrooms and beautifully updated baths providing peaceful private quarters. The lower level includes a large family room with fireplace and access to a secluded patio, plus an additional bedroom, bath, and versatile bonus space ideal for a gym, office, or game room. Mature landscaping, fruit trees, and multiple seating areas create a serene outdoor retreat. A rare opportunity to enjoy privacy, space, and classic Hillsborough elegance.

2323 Summit DR, Hillsborough

Listed by Disen Cai RE Group, 650-622-2156 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Kristin Lum from SGP
747 Bromfield RD, Hillsborough
$9,000,000
4 Beds ⋅ 5 Baths ⋅ ML82036538 MLS
Lower Hillsborough Mid-Century Modern Masterpiece. Walls of glass, soaring ceilings, and resort-caliber grounds define this iconic single-level estate set on a mostly level .716-acre (31,192± sf) lot along one of Hillsboroughs most coveted streets. The 4,670± sf residence showcases a gallery-style entry leading to dramatic living and dining rooms with limestone and granite fireplaces, expansive scale, and seamless indoor-outdoor flow through tall framed glass doors. A perfectly positioned powder room off the main entry offers convenient outdoor access. The stylish chefs kitchen features sleek cabinetry, Wolf 6-burner range with double ovens and grill, 48 Sub-Zero refrigerator, Miele wall oven and microwave, two Bosch dishwashers, and an oversized island with prep sink. An adjacent family room with built-in desks opens to an Ipe deck. The luxurious primary suite opens to the pool, with a spa-inspired bath and heated floors. Three additional ensuite bedrooms provide privacy and comfort. A newly constructed 1,095± sf ADU (2022) with separate address includes full kitchen, living areas, AC, and heated floors. Lush grounds offer pool, spa, pool house with Nano doors, fire pit with built in seating, outdoor kitchen with Lynx appliances, lawn area, solar, EV- outlet, mud/laundry room.

747 Bromfield RD, Hillsborough

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

Sold listing courtesy of RECIP from RCIP
588 Craig RD, Hillsborough
$9,280,000
5 Beds ⋅ 5 Baths ⋅ ML82036409 MLS
Welcome home to your modern farmhouse in the coveted Carolands neighborhood of Hillsborough. Situated on a flat and usable .52-acre lot, this home was rebuilt and expanded in 2021 from the foundation up, ensuring a turnkey and comfortable living experience. The main house boasts 4 bedrooms and 4 bathrooms, plus a 1-bedroom, 1-bath ADU. Inside, discover 16-foot ceilings, stunning wood floors, abundant natural light, and premium upgrades. The chef's kitchen features Thermador appliances and an 11-foot island, with La Cantina doors for seamless indoor-outdoor flow to your outdoor oasis that includes a new pool/spa, BBQ, bocce ball, expansive lawn, and fruit trees. There is also a large side yard perfect for basketball, extra cars, or even a boat. This property combines rare single-level living with modern features, great natural light on a flat, usable lot, and a neighborhood that invites walks and bike rides.

588 Craig RD, Hillsborough

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

Sold listing courtesy of Amy Xiao from KWCU
530 Barbara WAY, Hillsborough
$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
300 Glendale RD, Hillsborough
$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
35 Bel Aire CT, Hillsborough
$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
515 N San Raymundo RD, Hillsborough
$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
530 Darrell RD, Hillsborough
$3,900,000
5 Beds ⋅ 5 Baths ⋅ ML82022122 MLS
Situated in the prestigious Carolands, 530 Darrell Rd combines timeless character with modern convenience. With easy access to I-280, it offers equal commute times to San Francisco and Silicon Valley, lies within a top-rated school district, and is just 2.5 miles from Downtown Burlingame. Double wooden entry doors with custom leaded glass (sold separately) open to a bright living room with stone fireplace, wood-paneled ceiling, recessed lighting, and wall of glass to the covered lanai. The dining room, framed by Japanese-inspired sliding doors, is lit by skylights that reflect off hardwood floors. The eat-in kitchen has a breakfast nook, pantry, butler's pass-through, granite island with sink and bar, built-ins including dual ovens, cooktop with hood, paneled refrigerator, and a rare cooking fireplace. Off the kitchen are an en-suite guest room with outdoor access, maid's room, and garage. A bedroom/office and powder room complement the foyer, while the opposite wing hosts 3 bedrooms and 2 baths, including the primary suite with high ceilings, fireplace, patio, and spa-like bath. Outdoors enjoy a lanai with pond, fountains, waterfall, sparkling pool, patios, lawn, mature trees, outdoor powder, paver driveway, 2-car garage, and shed.

530 Darrell RD, Hillsborough

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

Sold listing courtesy of Chuan-heng Lin from BQG
55 Del Monte DR, Hillsborough
$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
75 Eugenia WAY, Hillsborough
$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
380 Arden RD, Hillsborough
$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

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