Hillsborough CA 5 Bathroom Real Estate, Homes, Condos for Sale

5 Beds ⋅ 5 Baths ⋅ ML82057153 MLS

Nestled behind private gates on approximately one-half acre in coveted Hillsborough, 380 Robinwood Lane is a thoughtfully remodeled estate blending modern design with effortless resort-style living. Surrounded by mature trees, lush landscaping, expansive turf lawn areas, and beautifully manicured grounds, the home offers exceptional privacy and seamless indoor-outdoor living. Light-filled interiors feature vaulted ceilings, walls of glass, and an expansive great room designed for everyday living and entertaining. The state-of-the-art chef's kitchen is anchored by a striking Taj Mahal quartzite waterfall island, professional-grade appliances, extensive custom cabinetry, and abundant storage. The home offers four en suite bedrooms plus one additional bedroom, including a private primary retreat with multiple fitted closets, a heated stone bath, and tranquil backyard views. A tucked away lower level en suite provides added flexibility for guests and multigenerational living. The lower level also includes a media room and family room with direct access to the backyard retreat. Outside, enjoy a sparkling pool, outdoor kitchen, expansive turf lawn, architectural landscaping, and multiple spaces for relaxing and entertaining.

380 Robinwood LN, Hillsborough

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

$9,880,000

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

$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

$11,950,000

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

$3,500,000

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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$12,600,000

5 Beds ⋅ 5 Baths ⋅ ML82021202 MLS

HILLSBOROUGH'S MOST EXCITING NEW CONSTRUCTION! Brand New Designer Showcase Overlooking the Bay near Nueva School. Dream Team of design and craftsmanship: award-winning San Francisco designer Studio Michael Hilal infuses cutting-edge modern DNA with warmth, livability, and a symphony of handpicked accoutrements. Custom builder Nejasmich Developments delivers renowned detail and artistry to a sleek canvas by Sausalito architect Brooks McDonald. The INNOVATION begins with a one-story building envelope. This platform sets the stage for ceilings over 12 feet, and 360 DEGREES OF LUXURY, with dynamic flow to usable flat lands at both front & rear. SEAMLESS is a most fitting theme for this lifestyle. Minimize the boundaries of indoors & outdoors, seamless attention to clean lines & finishes harmonizes as organic ambiance. | European Luxe meets Eastern Minimalism| Showstopper Great Room | Bay-View Party Terrace off Dining Room | 4 beds, 3.5 baths, plus Office, + Family Den in main home | Deluxe ADU for sleeping quarters, kitchen/laundry | Pro quality Gym w/ morning bar, German Sauna, backlit mirrors | Decadent Wine Pantry | Premium millwork of white oak & walnut, curated designer lighting | 3 Steam Showers | Pewter-Flamed Limestone hardscape | Gated Entry | Fire Pit | Outdoor Grilling Hub

55 Del Monte DR, Hillsborough

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

Sold listing courtesy of Kristopher Mares from KWPEN

$8,000,000

5 Beds ⋅ 5 Baths ⋅ ML82020606 MLS

Experience the perfect blend of luxury, elegance & California living in this breathtaking Mediterranean estate. This residence offers unparalleled privacy & sweeping views of the San Francisco Bay & surrounding mountains. A long, gated driveway welcomes you setting the stage for the home's elegant interior. Step inside to a dramatic, light-filled foyer featuring a graceful winding staircase that leads into an expansive living room framed by floor-to-ceiling windows showcasing the spectacular views.The gourmet chef's kitchen is comes complete with a large center island, elegant stone countertops, & top-of-the-line Viking stainless steel appliances. A richly wood-paneled library/office & spacious formal living & dining areas add sophistication, while new double-pane windows enhance comfort & energy efficiency throughout the home.Upstairs a primary suite awaits, featuring a spa-inspired bath with a jetted soaking tub, alongside generously sized bedrooms offering comfort & privacy. The impeccably landscaped grounds create a true oasis, featuring a resort-style pool & spa, & private tennis court. Perfect for both relaxation & entertaining, this property offers an unmatched lifestyle in one of California's most coveted settings.

75 Eugenia WAY, Hillsborough

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

Sold listing courtesy of Cici Wang from CBR

$6,660,000

4 Beds ⋅ 5 Baths ⋅ ML82019925 MLS

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

380 Arden RD, Hillsborough

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

Sold listing courtesy of Kenny Zhang from VHVOG

$5,210,000

4 Beds ⋅ 5 Baths ⋅ ML82018061 MLS

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

940 Hayne RD, Hillsborough

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

Sold listing courtesy of Jeff Harber from APR

$7,486,250

5 Beds ⋅ 5 Baths ⋅ ML82016885 MLS

Main 3770, guesthouse 726, garage 405 = 4901. The picture of storybook charm is in this desirable lower Hillsborough, single level home. Main house is 4 bedrms, 4 baths, 2 offices, 1 spacious overlooking front gardens, & other attached to the primary ensuite. Newly built custom guest house. Guest house is 1 bed/1 bath. It includes a living rm w/fireplace, kitchen, & Nana doors opening to the backyard w/ a sunny bedrm, gorgeous bathrm, & relaxing sauna. The interiors of the main home include formal spaces w/an open family/great room. Formal living rm boasts a large gas fireplace & sliding French doors to the backyard. The chefs kitchen is open to the family rm & includes a separate wet bar, counter dining, & wine closet, all surrounded by handsome cabinetry. The lavish primary bedrm wing features a fireplace, an adjacent office, a custom bathrm w/oversized shower & heated floors, large walk-in closet, & sliding doors leading to the backyard. There are three additional bedrms, 1 is ensuite. The backyard is quintessential California living at its finest w/sparkling pool & spa, a built-in BBQ, dining & lounging areas, a fabulous firepit & seating area, cold plunge pool & incredible gardens. Blocks to downtown Burlingame & Broadway Aves, close to airports, SF, excellent schools

1715 Forest View AVE, Hillsborough

Listed by Valerie Soltau, 650-464-3896 from Parc Agency Corporation
(If provided) CoList: from

Sold listing courtesy of The Sharp Group from KWPEN

$6,530,000

5 Beds ⋅ 5 Baths ⋅ ML82010779 MLS

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

801 Eucalyptus AVE, Hillsborough

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

Sold listing courtesy of Vahid Firouzdor from COMPS

$11,000,000

5 Beds ⋅ 5 Baths ⋅ ML82010162 MLS

240 W Santa Inez AVE, Hillsborough

Listed by Daniel Buckley Chavez, 650-576-5708 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Daniel Buckley Chavez from CBR

$3,900,000

4 Beds ⋅ 5 Baths ⋅ ML82007421 MLS

Cape Cod Charm in Lower Hillsborough! An utterly spell bounding property that offers an amazing ambiance of natural beauty and architectural style. Enchanted creekside setting with lush grounds, spectacular color, peaked roofs, meandering pathways and white picket fences emerge simultaneously upon arrival. Circa 1936, meticulously maintained and exploding with character. Wide plank flooring, white paneled walls, wainscoting, bead board built-ins, touches of brick, charming nooks and stunning dormer windows throughout. An abundance of natural light with several French Doors leading to the rear veranda and the pristine grounds. Two primary en suites, one per floor. Separate office. Modern day upgrades include windows and doors, fresh paint, remodeled baths and impressive lighting. Attached garage and additional basement/workshop area. Acclaimed South Elementary, Crocker Middle and Aragon High School. Considering price, location, condition, and size, this special property represents the best of value that Hillsborough has to offer and poses as an ideal investment to enjoy all the convenience and amenities that peninsula living is famous for.

807 Crystal Springs RD, Hillsborough

Listed by Mike Bohnert, 650-504-2378 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Sam Kaykin from UMBRA

$13,750,000

6 Beds ⋅ 5 Baths ⋅ ML82004484 MLS

1.81 level acres in the most prime area of Lower Hillsborough. This is the only building site available in Hillsborough, Atherton or Woodside that will accommodate a true world class estate and everything that comes with it. Also sub-dividable into two .9 acre lots.

210 Uplands DR, Hillsborough

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

Sold listing courtesy of Jim Arbeed from CBR

$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

$6,800,000

5 Beds ⋅ 5 Baths ⋅ ML82002437 MLS

DESIGN FOR LIVING: THE PERFECT MEETING OF SUN, CELEBRATION, AND SAVOIR FAIRE! Remodeled designer quality unfolds across multiple destinations, with minimal boundary between indoor and outdoor living. 5 bedrooms, 3 full baths, 2 half baths, plus large Office (or gym), and enormous recreation room of 21 x 26 feet. Majority of the home flows on one level, including four bedrooms all together highlighted by a decadent expanded Primary Suite with 3 closets & marble bath. Tucked-away 5th bedroom suite also on main level perfect for guest or au pair. Myriad luxury details including a Craft Cocktail Bar, Wolf, Sub-Zero, high ceilings, integrated audio, outdoor kitchen, solar panels, Tesla power walls & more! Prestigious Jacaranda Circle backs up to Crocker Open Space, in the spirit of Woodside or Tahoe! Only 0.6 mile to Crocker Middle, 1.1 mile to Nueva School, 1.2 mile to West School, 1.9 mile to Apple Store on Downtown Burlingame Ave. The Primary Suite deserves its own paragraph. Expanded and remodeled, indulgent retreat with 3 customized closets plus built-in chest of drawers * Primary bedroom ceilings peak at nearly 12 feet. * Calistoga vibes opening out to pool and greenbelt vista. *Lighted Sport Court *Huge 3-car garage *Tons of western sunlight across pool and entire back of home*

748 Jacaranda CIR, Hillsborough

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

Sold listing courtesy of Serena Conti from APR

$5,450,000

4 Beds ⋅ 5 Baths ⋅ ML81999777 MLS

Custom built in 2002 this beautiful 4,760 sq ft home located in the desirable city of Hillsborough features 4 spacious bedrooms and 4 full bathrooms and powder room. The well-appointed kitchen is perfect for aspiring chefs and entertainers alike, offering ample space for culinary creations. The home boasts a formal dining room for hosting elegant dinners and a separate family room for more casual gatherings. Additional amenities include central forced air heating to ensure comfort throughout the year. The upper floor hosts a convenient laundry area, adding to the home's practical layout. The property features a combination of flooring materials, enhancing both aesthetic appeal and functionality. The home is situated within the Hillsborough City Elementary School District, making it a suitable choice for families. With a generous minimum lot size of 23,052 sq ft and a spacious three-car garage, this property offers ample space for both living and storage needs.

2813 Easton DR, Hillsborough

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

Sold listing courtesy of Max Lo from GRBA

$3,950,000

5 Beds ⋅ 5 Baths ⋅ ML81996987 MLS

ESCAPE TO SERENITY: PRIVATE AND QUIET LOCATION! LARGE USABLE YARD! AMAZING SCHOOLS! A must-see breathtaking Hillsborough Park home! Top rated public schools: South Elementary School and Crocker Middle School/ Close to Downtown San Mateo shops and restaurants / Located at the end of a private cul-de-sac / 18 ft vaulted ceilings in the grand living room / Bright natural light / Primary suite + 2 en suite bedrooms within close proximity / Two additional en-suite quarters for guests, home office, au-pair, etc. / Whole-home WiFi connectivity and updated server offers seamless access for work, streaming and smart home features / Entertainers dream / Backyard oasis set on over an acre of land includes pavilion and huge plateau play area, dining/bbq courtyard, detached studio with outdoor sitting area and hot tub terrace / Minutes from downtown San Mateo with shops, restaurants, grocery, CalTrain as well as Crystal Springs Reservoir Trail, Bay Trail and easy access to Hwy 280 and SFO Airport / An opportunity to be within close proximity of the city but also escape to serenity / This is one you don't want to miss!

1021 Merner RD, Hillsborough

Listed by Kathryn Gerhardt, 650-773-3595 from Gilmartin Group
(If provided) CoList: from

Sold listing courtesy of Kathryn Gerhardt from GILM

$4,400,000

5 Beds ⋅ 5 Baths ⋅ ML81996926 MLS

Verdant retreat of 1.4 acres in the heart of prime Hillsborough. This sophisticated home has views of trees from nearly every room. A voluminous foyer with a focal picture window looking onto lush foliage introduces the bright open interior with soaring ceilings, spacious, elegant formal rooms, 3 bedroom suites with walk in closets (2 are primary suites), & a kitchen updated with center island, all new appliances (Thermador range, Bosch refrigerator + dishwasher & wine cooler) opens to a big eat in kitchen and sizable family room. An office or library off the main hallway can be closed off or open to extend the living room and a perfectly situated powder room serves the common areas. Other remarkable features include: 3 car garage, AC, Generator, laundry room, huge primary bathrooms & closets, loads of storage & a backyard large enough & private enough to feel like you are in your own forest. Create your own hiking trail & enjoy nature or develop the land - so many possibilities!

105 Stonepine RD, Hillsborough

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

Sold listing courtesy of Zivi He from CBR

$5,200,000

6 Beds ⋅ 5 Baths ⋅ ML81996728 MLS

This stunning home captures the elegance and prestige of Hillsborough, nestled in the sought-after Tobin Clark Estates neighborhood. Set on a spacious lot at the entrance of a quiet cul-de-sac, it offers a prime location just minutes from Laurelwood Shopping Center, Crystal Springs Village, and the vibrant Downtown San Mateo scene. Top-rated schools, including the College of San Mateo, are nearby, with easy access to Highway 92, 101, 280, & the San Mateo Bridge. Inside, high ceilings, recessed lighting, and tall windows create an open, airy ambiance. The lower level features a seamless flow between the living room, family room, and chefs kitchen, perfect for everyday living & entertaining. The kitchen is equipped with brands such as Thermador, KitchenAid, and Marvel appliances, as well as featuring a pantry, sleek countertops, and a wine fridge. The home boasts comfortable, light-filled bedrooms, including a retreat-like primary suite. The bathrooms are pristine, offering style and functionality. Additional highlights include a 3-car garage and an indoor laundry area. Outside, a sparkling pool, hot tub, and spacious lawn provide the perfect setting for outdoor living. This home blends luxury, comfort, and convenience - a gem like this doesn't come around often, don't wait!

1285 Tournament DR, Hillsborough

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

Sold listing courtesy of Max Lo from GRBA

$5,150,000

6 Beds ⋅ 5 Baths ⋅ ML81989632 MLS

This beautifully updated Hillsborough estate offers luxury and panoramic Bay views. Full lenth windows cover the whole side including living room, dinning room, kitchen, and family room captures the stunning scenery. The formal dining room and gourmet kitchen, featuring top-tier appliances, custom cabinetry, and granite countertops, flow into a family room with sliding doors to an upper deck overlooking the Bay. The home has two en-suite bedrooms, both with double sinks and a shower over the tub. The grand primary suite includes a walk-in closet, double vanity, stall shower, jet tub, and a private balcony. Two additional bedrooms and a luxury hallway bathroom with a double vanity and shower over tub complete the upper level. The lower level features two more bedrooms, a spacious office, a gym, and an in-house laundry. Recent upgrades include an updated deck, new hardwood floors, replaced ceiling lights, fresh paint, solar panels with two Tesla batteries gives the house uninterupted full power, and a commercial-grade AC system. All bathrooms have smart toilets. Outside, a childrens play yard and two driveways offer ample parking. Located in a top-rated school district and walking distance to Nueva School, with easy access to Highway 280. Luxury, convenience, and stunning views.

2625 Skyfarm DR, Hillsborough

Listed by Xiaozhu Kang, 650-683-6888 from Coldwell Banker Realty
(If provided) CoList: Amy Wang from Coldwell Banker Realty

Sold listing courtesy of Yvonne Yang from APR

$5,290,000

5 Beds ⋅ 5 Baths ⋅ ML81985474 MLS

Completely transformed within the last five years, this beautifully remodeled Carolands home offers sophisticated elegance and modern luxury on over one-half acre. The entire property is oriented toward the transformed rear grounds with a vast stone terrace, soccer-worthy lawn, and a separately fenced recently added pool and spa. The fully level outdoor space also includes a barbecue kitchen, lounge, and fireplace, perfect for entertaining in privacy. The main home is predominantly on one level with an entire wall of glass and French doors that connect the public rooms with the bedroom wing, all opening to the rear grounds. There are 4 bedrooms and 3.5 baths including the primary suite and 2 bedrooms with a shared bath on the main level. The lower level features a large recreation room, kitchenette, bath, and a fourth bedroom with outside entrance, making this area also suitable for extended family living quarters. Plus detached guest quarters, currently customized for remote work, feature a large desk, built-in cabinetry, integrated Murphy bed and custom closets by California Closets, and a large bath with pool access. Located near top-rated public and private Hillsborough schools, this home combines luxury, flexibility, and indoor/outdoor convenience.

3990 Ralston AVE, Hillsborough

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

Sold listing courtesy of Jim Arbeed from CBR

$6,250,000

4 Beds ⋅ 5 Baths ⋅ ML81982369 MLS

2130 Redington RD, Hillsborough

Listed by Jeff Harber, 650-740-2418 from Compass
(If provided) CoList: Ellen Mazzoni from Compass

Sold listing courtesy of Emma Elfving from APR

$7,000,000

5 Beds ⋅ 5 Baths ⋅ ML81966930 MLS

Stunning Designer Showcase Home just steps away from Hillsborough's Vista Park. This Modern Colonial was completely remodeled and reimagined in 2014 and featured in Gentry Magazine and Hillsborough's Kitchen Tour. Offering the perfect blend of contemporary high-end designer finishes with 1930's period details, this gorgeous estate is truly exceptional. An extraordinary indoor-outdoor open floor plan with formal and informal living and dining spaces is ideal for both large entertaining as well as a private family retreat. Features 5 generous bedrooms, 4.5 spa-inspired bathrooms, formal living and dining rooms, and an oversized kitchen with coffee bar and wine storage. The rear gardens rival a boutique hotel with bluestone pathways, lush lawns, sculptured topiaries, potted palms, outdoor kitchen, lounge areas, a raised fire-pit and a sparkling swimming pool. Approved plans for an 800 s.f. ADU on an unused area of the lot! Walking distance to Vista Park and zoned for North Hillsborough Elementary.

1048 Whitwell RD, Hillsborough

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

Sold listing courtesy of Sophia Waldman from SIR

$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

$5,150,000

5 Beds ⋅ 5 Baths ⋅ ML81979487 MLS

Spacious and bright, with a fantastic layout and a wonderfully flat yard, the Oak Rim Retreat is the Hillsborough home you have been waiting for. With a ground-floor bedroom suite, sparkling chefs kitchen, four bedrooms upstairs, including a large primary suite with big closets and an oversized soaking tub, and two additional bedrooms and full bath in the separate pool house, this home has space for everybody. The stately facade welcomes you home, and the intelligent floor plan weaves practicality with comfort. And when entertaining, equally impressive - the soaring ceilings of the double-height foyer open up nicely to the living room, which features a modern central fireplace and stylish wet bar. Indoor/outdoor entertaining is easy, with sliding doors in the center of the home that open up from the kitchen to the beautiful backyard, which features a pool, rose planters, plenty of patio space and a large grass play area. The breakfast nook, powder room, family room, formal dining room, and a large three-car garage complete the home. This is it! Welcome home.

1475 Oak Rim DR, Hillsborough

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

Sold listing courtesy of Samantha Huang from BHGJF

$8,500,000

5 Beds ⋅ 5 Baths ⋅ ML81978302 MLS

Discover a masterpiece of luxury living in Hillsborough's most prestigious neighborhood, boasting breathtaking San Francisco Bay Area views. Set on over 1 acre, this exquisite home features an open floor plan, a chef's kitchen, and a luxurious primary suite, offering an unparalleled living experience. Step outside to your private pool and gazebo, where you can soak in the captivating vistas that define the essence of Bay Area living. Note: County records show 4 Bedrooms, 5585 SF. 5861 Sf is based on floor plan measurements provided by Bhupesh Patel. Sellers plans show 5th bedroom. Buyer to investigate to satisfy themselves.

160 New Place RD, Hillsborough

Listed by Susan Herman, 650-400-4383 from Compass
(If provided) CoList: Austin Herman from Compass

Sold listing courtesy of Vahid Firouzdor from COMPS

$4,100,000

5 Beds ⋅ 5 Baths ⋅ ML81974052 MLS

795 Tournament DR, Hillsborough

Listed by David Scanlon, 650-743-9592 from Compass
(If provided) CoList: from

Sold listing courtesy of Emma Elfving from APR

$4,400,000

4 Beds ⋅ 5 Baths ⋅ ML81973500 MLS

Nestled on a spacious 0.52-acre corner lot, this home boasts potential to remodel, expand or rebuild. Inside enjoy large rooms that are bright and airy with a fantastic layout, ideal for multi-generational living or growing families. The main level features a formal living room, dining room, eat-in kitchen, family room, and three bedrooms. The lower level offers a huge bonus room for entertaining and additional bedrooms all with direct access to the large yard and pool. The spacious front and backyard includes large lawns, mature trees, a pool, and tree house. Located in the Carolands, this home offers quick access to Highway 280, Downtown Burlingame, and top-rated schools. Dont miss this hidden gem ready for your personal touches.

785 Pullman RD, Hillsborough

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

Sold listing courtesy of Phil Chen from SGP

$5,500,000

4 Beds ⋅ 5 Baths ⋅ ML81973388 MLS

PRIME LOWER HILLSBOROUGH ESTATE WITH 1.2-ACRES OF MOSTLY USABLE LAND. This is THE BEST DEAL you will find in Lower Hillsborough right now! This RARE property presents a unique opportunity for development, to make it your own. This location is surrounded by scores of other multi-million-dollar mansions just down the street; this home is nestled in one of Hillsborough's most prestigious neighborhoods. You can move into the existing home, and while you live there you can design and expand to create your dream space! ENDLESS POTENTIAL. Don't settle for less than the best, and don't think of any other property until you've seen this one! Plans and surveys are available.

2055 Forest View AVE, Hillsborough

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

Sold listing courtesy of Stanley Lo from GRBA

$7,380,000

5 Beds ⋅ 5 Baths ⋅ ML81971666 MLS

Situated on a prime lot in the Carolands, this beautiful home is as stunning as it is practical. Featuring dual primary suites, a vaulted-ceiling family room that opens up to the sunny yard, fantastic skylit open kitchen, and a spectacular layout (mostly on one level!) that seamlessly unites formal living areas with practical and easy family spaces, this home is built to make the elegant Hillsborough lifestyle a breeze. The formal living room, dining room, and office are superbly finished, with wainscoting, crown moldings, and beautifully stained wooden bookshelves, with the primary bedroom with walk-in steam shower completing the formal wing of the house. Coming to the heart of the home, the family room and kitchen integrate nicely as a natural place to host casual or formal gatherings, flowing easily in and out of the beautifully landscaped backyard. And when it is time for bed, the wonderful floor plan really shines, with the three kids rooms and shared bath centered around a secondary family play room, close to one of the primary suites and above the guest or au-pair suite downstairs. Ample storage and a large 3-car garage finish out the ground floor. This is really the Hillsborough home of your dreams!

500 Pullman RD, Hillsborough

Listed by William Cheung, 650-759-8779 from Compass
(If provided) CoList: Chi-Raie Cheung from Compass

Sold listing courtesy of Anthony Galli from CBR

$4,750,000

5 Beds ⋅ 5 Baths ⋅ ML81959090 MLS

Luxury and Comfort. This Hillsborough gem offers Spectacular Panoramic Bay & Canyon Views from nearly every room! As you enter the house, you will be greeted by a Grand living and dining area featuring a spacious open floor plan, soaring high ceilings, elegant skylights, expansive windows, & glass doors that showcase the breathtaking views that this house offers. The adjacent chefs kitchen is a masterpiece, boasting ample cabinetry, a center island with a built-in sink, a breakfast bar, a second dining area, and a cozy family room w/ a fireplace. After a long day, retreat to one of the several comfortable & relaxing bedrooms. The master suite offers a serene escape w/ picturesque views & a harmonious primary bath with soaking tub. The rear exterior extends the length of the living spaces, providing a versatile and inviting outdoor area for leisure and entertainment. Enjoy a large back deck, patio, and BBQ area, perfect for relaxing and soaking in the breathtaking views from the privacy of your backyard. With its exquisite design, spacious interiors, and a backyard oasis featuring every amenity you could desire, this home offers a lifestyle of comfort and opulence. This house is only less than a 10-minute drive from Downtown Burlingames array of popular shops, restaurants.

1305 Southdown RD, Hillsborough

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

Sold listing courtesy of Stanley Lo from GRBA

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