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$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
$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
$4,300,000
5 Beds ⋅ 4 Baths ⋅ ML82036641 MLS
COMP PURPOSES ONLY

30 Inverness WAY, Hillsborough

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

Sold listing courtesy of The Patty Dwyer Group from APR
$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
$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
$70,000,000
6 Beds ⋅ 17 Baths ⋅ ML82024133 MLS
Set on more than 12 secluded acres, Villa de Verano is an ultra-exclusive Hillsborough estate inspired by the elegance of Lake Como. The gated compound offers exceptional privacy, symmetry and scale, with a tree-lined drive leading to a grand motor court & the main residence, guest quarters & sports pavilion. The 12,404 sqft main residence spans 3 levels serviced by an elevator & overlooks the pool, reflection pond & sweeping views of San Francisco Bay. The 4,612 sqft guest house & sports pavilion complement the estate. Interior amenities include a fitness center, theater, game room, spa, & saltwater aquarium. Custom furnishings & art create a unified aesthetic. The grounds include an amphitheater, event lawn, Asian garden with koi pond, swimming pool, reflection pond, open air pavilion, rose garden, redwood grove & English spiral mound. The Sports Pavilion includes a 2 story sports lounge with a viewing platform overlooking a sunken tennis court, pickleball court, volleyball court, badminton court, bocce ball court, horseshoe court, shuffleboard court & putting green. The estate also features an executive length golf course. Upon its completion, Villa de Verano received the CLCA annual Grand Sweepstakes Award for best residential estate completed in the state of California.

3000 Ralston AVE, Hillsborough

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

Sold listing courtesy of Jia Xu from TRNX
$5,725,000
4 Beds ⋅ 4 Baths ⋅ ML82033948 MLS
Beautifully reimagined single-level home in coveted Lower Hillsborough. This 4-bedroom, 3.5-bath residence offers a thoughtfully updated layout, anchored by a newly redone open kitchen and family room designed for modern living and effortless connection. The interiors feature all-new flooring, custom cabinetry, and a chefs kitchen appointed with Miele appliances, including an induction cooktop and built-in espresso machine. Expansive new windows and sliding doors fill the home with natural light, complemented by new recessed lighting throughout. Additional highlights include a refreshed fireplace, a stylish wet bar, and a brand-new garage door. Outside, the property has been enhanced with a new metal roof, freshly landscaped grounds, and a new concrete patio, ideal for entertaining or relaxing in the private backyard, with ample space to add a pool and ADU. Tucked away on a private street just minutes from top-rated schools, parks, and downtown conveniences, this turnkey residence is ready for its next chapter.

340 Arden 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
$9,540,000
6 Beds ⋅ 7 Baths ⋅ ML82032691 MLS
Almost fully rebuilt in 2022, this Santa Barbara-style Mediterranean in Hillsborough blends timeless architecture with modern systems and resort-style living. Interior design by JD Bartell creates a truly special & cohesive residence for daily living & entertaining. The home offers up to 6 bedrooms & 6.5 bathrooms with Venetian plaster throughout, custom white oak floors, seamless cabinetry & doors with a dramatic staircase. This home includes radiant heat and air conditioning with multiple zones, integrated security cameras, lighting & audio. The chef's kitchen features a huge custom book-matched island with top-of-the-line appliances, dual sinks, ample storage, plus a temperature-controlled wine cellar, open to the large family room. Extensive upgrades include 400-amp electrical service, new copper plumbing and wiring, dual internet, 19.5 kWh solar, a 22 kWh Generac backup generator, tankless water heaters, & whole-home water filtration. Resort-style grounds include fruit trees, drought-tolerant landscaping, smart irrigation, a resurfaced pebble pool with water features, travertine hardscape, circular paver driveway, iron gates, and an outdoor BBQ. A rare offering combining architectural character with a more transitional interior full of custom upgrades.

2950 Churchill DR, Hillsborough

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

Sold listing courtesy of Ramez Tabri from ALNC
$7,100,000
5 Beds ⋅ 4 Baths ⋅ ML82033175 MLS
EPIC HOMAGE TO CRAFTSMANSHIP AND LIFE IN THE SUN...One of Hillsborough's Most Elite Custom Remodels, steeped in the Magic of Montecito and Palm Beach. Every inch meticulously curated of high-end caliber inside and out. Ultimate privacy heightens soaring views above canyon, ridgelines, and sun-blessed luminosity. Top flight luxury designer elements of Venetian plaster walls, vaulted ceilings of 14-15 feet, European tilework, mahogany doors, and made-to-order light fixtures by Steven Handelman of Santa Barbara. Wolf, Sub-Zero, Miele, exquisite custom cabinetry, & more. Indoor/Outdoor celebration as a personal resort with saltwater PebbleSheen pool, 3 waterfalls & raised spa. Flat grassy yards, barbecue cove, secret Napa garden of fruit orchard & irrigated veggie beds. The beauty of the floorplan includes 4 bedrooms on the main level, plus private lower level for 5th bedroom, huge media room & 2nd kitchen. This level is the perfect in-law apartment, teen hangout, or poolside media lounge. And shhhh, don't forget the world-class temp-controlled wine cellar as your own speakeasy! Prestige cul-de-sac location within minutes of Nueva & West Schools, & easy Hwy 280 connection to VC realm of Silicon Valley, plus AI, private equity, & biotech of South San Francisco and Financial District.

25 Searsville CT, Hillsborough

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

Sold listing courtesy of Chris Iverson from DP
$5,750,000
6 Beds ⋅ 7 Baths ⋅ ML82033179 MLS
A Hillsborough masterpiece: grand, expansive, & full of timeless Neoclassical charm with modern-traditional elegance, offering resort-style living in the coveted Skyfarm neighborhood. This prestigious estate welcomes you w/ a stately four-column façade, grand double doors, & dramatic foyer. Sun-filled formal living & dining rooms set the tone for entertaining, while the gourmet chefs kitchen features granite countertops, custom cabinetry, high-end appliances, & pass-through bar seating w/ direct backyard access. The family room impresses w/ exposed beam ceilings, wood-paneled walls, a wet bar, & floor-to-ceiling brick fireplace. Boasting 6 bedrooms, multiple en-suites, 2+ bonus rooms, abundant storage, & a lounge area w/ sink by the four-car garage, this home offers flexibility for family, guests, & work-from-home living. The primary suite includes a private balcony overlooking the backyard, pool, & tennis court, ready for resort living. Outdoor amenities include BBQ/lounge areas, mature trees, & a full-size tennis court, perfect for entertaining. Close to Downtown Burlingame, HWY 101, San Francisco, & Silicon Valley, this rare estate delivers prestige, privacy, & extraordinary living in one of Hillsboroughs most desirable neighborhoods.

746 Jacaranda CIR, Hillsborough

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

Sold listing courtesy of Stanley Lo from GRBA
$12,500,000
8 Beds ⋅ 8 Baths ⋅ ML82032610 MLS
Striking modern estate offering the perfect blend of luxury, scale, and design. This full scale renovation showcases soaring ceilings, dramatic floor-to-ceiling windows, and seamless indoor-outdoor living. The spacious floor plan features grand formal and casual living areas, a sleek chefs kitchen, and walls of glass opening to expansive terraces with serene tree-lined views. Luxury amenities include a private home theatre, gym, tasting room and wine cellar, elevator, and a resort-style backyard with pool house and built-in BBQ. The sparkling pool with water features, multiple lounge areas, and expansive patio create the ultimate setting for entertaining and relaxation.

1215 La Cumbre, Hillsborough

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

Sold listing courtesy of Jenny MacLeod from APR
$9,800,000
7 Beds ⋅ 8 Baths ⋅ ML82032512 MLS
Set behind private gates on a 0.645-acre parcel in Hillsborough's prestigious neighborhood, this 9,035 sq ft estate offers sweeping San Francisco Bay views & exceptional scale. A grand double-door entry opens to a dramatic foyer with a stained-glass dome skylight, leading to an expansive main level defined by floor-to-ceiling glass and abundant natural light. Custom coved & vaulted tray ceilings with architectural pillars enhance the living room, formal dining room, and family room, all unified by rich hardwood floors. Refined details include stained glass accents, skylights, crown molding, wainscoting, recessed lighting, and a multi-room audio system. The formal living and dining rooms feature fireplaces, with roof deck access ideal for entertaining. The family room includes a custom wet bar with wine cooler and built-ins. The chef's kitchen offers granite counters, center island, pantry, high-end appliances, and breakfast nook. The main level includes a paneled office, powder rooms, laundry, garage access, and a spacious primary suite. The lower level offers six additional bedrooms, staff quarters, wine cellars, a second kitchen, and access to a glass-enclosed indoor pool with spa. Expansive patios, synthetic lawn, walking paths, and motor court.

2930 Privet DR, Hillsborough

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

$10,200,000
8 Beds ⋅ 7 Baths ⋅ ML82032410 MLS
Welcome to 45 Calaveras Court, a brand-new modern masterpiece nestled in the Hillsborough hills. Located at the end of a private cul-de-sac on a sizable 4-acre lot, this stunning residence offers approximately 7,000 square feet of elegantly designed living space. Enjoy unobstructed canyon views from every window, providing a breathtaking backdrop to your everyday life. Step inside to discover soaring ceilings that create an open and inviting atmosphere, complemented by an abundance of natural light that fills every corner. The expansive first floor features a massive entertainment deck, perfect for hosting gatherings or simply relaxing amidst nature. With a total of 8 bedrooms, including master suites on each level, this exceptional home is perfect for large families or multi-generation living.

45 Calaveras CT, Hillsborough

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

Sold listing courtesy of Greg Browman from 7A895
$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
$4,500,000
3 Beds ⋅ 3 Baths ⋅ ML82032145 MLS

571 Craig RD, Hillsborough

Listed by Debbie Elowson, 650-867-2217 from Compass
(If provided) CoList: from

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

1080 Macadamia DR, Hillsborough

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

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

460 Barbara WAY, Hillsborough

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

Sold listing courtesy of Gina Haggarty from APR
$11,000,000
5 Beds ⋅ 6 Baths ⋅ ML82014791 MLS
Experience timeless luxury at this grand Mediterranean estate, ~7,700 sqft total living space set on ~1.5 acres in the prestigious Tobin Clark area of Hillsborough. Showcasing panoramic views of the Bay and Peninsula. This exceptional property offers an unparalleled lifestyle of elegance, comfort, and privacy. The main residence features ~6,500 square feet of living space, including 5 ensuite bedrooms, each w/ access to a private terrace. A sweeping staircase, custom chandeliers, and soaring ceilings create a dramatic welcome, while the formal living and dining rooms, gourmet kitchen, & wine room provide elegant spaces for entertaining. The primary suite is a private retreat with a sitting area, custom walk-in closet, and spa-like bath. A separate 2 bed 2 bath guest house (~1,200 Sqft) includes its own kitchen, living area w/ fireplace, & private balcony and private garage, perfect for extended stays or multigenerational living. Outdoor amenities include an infinity-edge pool and spa, full-size tennis court, putting green, and multiple entertaining patios surrounded by mature landscaping. Located just minutes from top-rated Hillsborough schools, downtown Burlingame, SFO, and Silicon Valley, this is a rare opportunity to own one of Hillsborough's most iconic view properties.

171 Tobin Clark DR, Hillsborough

Listed by Wen Guo RE Group, 650-817-5000 from KW Advisors
(If provided) CoList: from

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

7 Windsor DR, Hillsborough

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

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

20 Pine CT, Hillsborough

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

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

1015 Woodland DR, Hillsborough

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

Sold listing courtesy of Nicholas Delis from APR
$7,780,000
5 Beds ⋅ 7 Baths ⋅ ML82027382 MLS
Built in 2021, this showstopping modern estate captures the essence of California living. Soaring ceilings and walls of glass open completely to reveal breathtaking hillside and Bay views, blurring the line between indoors and out. The designer kitchen stuns with custom rift-oak cabinetry, marble island, and top-tier appliances. An entertainers dream, the outdoor terrace features a built-in BBQ, spa, fire pit, and endless views. Smart home technology, solar power, and a premier Hillsborough location complete this rare modern masterpiece.

60 Glengarry WAY, Hillsborough

Listed by Victoria Yang Surles, 415-818-3603 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jennifer Griessel from CCPCR1
$5,300,000
3 Beds ⋅ 4 Baths ⋅ ML82026991 MLS
A Modern Transformation with Sweeping Bay Views! Beautifully remodeled for modern living, this Lower Hillsborough home showcases an open-concept design with wide expanses of glass that frame views across the San Francisco Bay and out to the Bay Bridge and East Bay hills. Natural light fills every room, two gas fireplaces add warmth, and wood-like tile floors unify the open living areas. Expansive formal rooms are complemented by a designer kitchen and family room combination, creating an ideal layout for entertaining and everyday comfort. Rounding out the main level are three spacious bedrooms, including a primary suite that takes full advantage of the views, plus there is a flexible-use lower level with large bonus room and adjoining bath. Outside, an expansive view deck with cable-strung railings and terraced lawns extend the living space, providing ample room for entertaining and play. With its modern transformation, dazzling views, and sought-after Lower Hillsborough setting, this home presents the perfect place to live midway between San Francisco and Silicon Valley.

442 El Arroyo RD, Hillsborough

Listed by Mark Johnson, 650-685-7648 from Coldwell Banker Realty
(If provided) CoList: from

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

300 Glendale RD, Hillsborough

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

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

715 Brewer DR, Hillsborough

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

Sold listing courtesy of Jenn Gilson from MCGR
$7,318,000
5 Beds ⋅ 6 Baths ⋅ ML82025896 MLS
THE BEST OF THE BEST IN HILLSBOROUGH. Award-Winning architectural design meets timeless farmhouse elegance. Previously featured in Modern Luxury Silicon Valley Magazine, this home was meticulously remodeled & redesigned in 2017 by both an award-winning designer & architect. A stunning blend of modern farmhouse designs and contemporary elements, this exceptional estate is crafted for stylish living and effortless entertaining. Eco-minded design and sustainable elements create a healthy, harmonious environment throughout. The expansive indoor-outdoor layout offers formal and informal living and dining areas, a grand kitchen with a Taj Mahal quartzite island that seats 12, plus 5 bedrooms, 5.5 spa-inspired bathrooms, a loft, office, and soaring vaulted beam ceilings. Enjoy multiple en-suites, sliding barn doors, large windows / glass doors, and a seamless kitchen/family room retreat. The resort-style grounds include a terraced garden, lush lawn, outdoor kitchen, fire-pit lounge, hot tub with natural rock waterfall, pool, sport court, & a spacious outdoor gym / pool house with full bath. Approved plans for an 800 sq. ft. ADU add even more opportunity. Moments to top-rated schools including Nueva, Crystal Springs Uplands, and other acclaimed schools. TOO MUCH TO LIST HERE.

1485 Oak Rim DR, Hillsborough

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

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

310 Ranelagh RD, Hillsborough

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

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

30 Live Oak LN, Hillsborough

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

Sold listing courtesy of Judy Zhu from CBR
$6,000,000
4 Beds ⋅ 3 Baths ⋅ ML82025145 MLS
A rare opportunity. Located in the coveted lower-Hillsborough Ryan Tract Neighbourhood. 1735 Crockett Lane is an ideal home for entertaining! The home is located on a quiet cul-de-sac. The common area includes a family room, breakfast nook, formal dining room, and formal living room area. This one story 4-bedroom 3 bath home is expansive and private. Plenty of storage space. Located on a private lot with a generally flat backyard on a desirable cul-de-sac street. High ranked school district. North School, Crocker Middle School, and Burlingame High School. Located near Downtown Burlingame with plenty of stores and restaurants. There are an additional bedroom and bathroom located on the opposite side of the common area. Over the years this has been used as a bedroom or office, but it is ideal for a possible au-pair suite or in law suite. Possibility to expand home to 4500 SqFt and add an additional dwelling unit (ADU). Buyer to verify all information prior to close of escrow and removal of all contingencies.

1735 Crockett LN, Hillsborough

Listed by John Pang, 650-699-2838 from Realty One Group Extreme
(If provided) CoList: from

Sold listing courtesy of John Pang from VHVOG
$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

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