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$6,995,000
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

$8,999,000
3 Beds ⋅ 4 Baths ⋅ ML82044812 MLS
RARE OPPORTUNITY! Hurry, properties of this caliber, on this size lot, in this location rarely come on the market! You can remodel a home, but you can never recreate this location, this cul-de-sac, or this extraordinary lot. One of Hillsboroughs most sought-after and prestigious streets. Tucked away at the end of a quiet cul-de-sac, this extraordinary estate sits on one of the largest lots in the neighborhood, an exceptionally rare offering that will not become available again for years. Walking distance to vibrant downtown Burlingame and some of California's best public schools. Whether you choose to enjoy this beautiful estate as it is or create your own dream luxury residence, this is truly a once-in-a-lifetime opportunity in an irreplaceable location. Enjoy unmatched privacy surrounded by magnificent mature trees and lush landscaping, creating your own peaceful retreat. DO NOT WAIT, SERIOUSLY!!!

2155 Geri LN, Hillsborough

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

$5,999,000
4 Beds ⋅ 4 Baths ⋅ ML82055379 MLS
Located in Lower South Hillsborough, this spacious 3,440 sq ft home offers four bedrooms, three full bathrooms and separate office. The living room and an additional area feature wood-burning fireplaces, adding warmth and charm to the space. The home includes a separate family room and multiple dining options, such as a breakfast room, dining area in the living room, and an eat-in kitchen, All with access to a large sun lit flat back yard. The property comes with a two-car garage and is situated within the Hillsborough City Elementary school district. This residence combines functional living spaces with key amenities in a desirable location.

336 Brentwood RD, Hillsborough

Listed by Max Lo, 650-307-8816 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
$11,800,000
6 Beds ⋅ 8 Baths ⋅ ML82054575 MLS
Situated in one of the best locations in Hillsborough, 280 Uplands Dr is a rare opportunity on a flat, private, over-half-acre corner lot, steps from Crystal Springs Uplands School & South Elementary. This estate offers 6 bedrooms, 6 full baths & 2 half baths, all en-suite, with attached ADU. A dedicated office with fireplace, home theater with theatrical lighting and built-in refreshment station, and an adjoining bonus room. Upstairs, a bedroom suite is joined by a multi-purpose room with fireplace, ideal as a gym, bar, or rec space. All mechanical systems replaced, including new roof and four separate HVAC systems for comfort and efficiency. All-new interior finishes and a chef's kitchen with premium appliances, including Sub-Zero. Private rear driveway with automatic gate. Outdoor spaces offer true California entertaining: brand-new pool and spa with automatic safety cover, outdoor kitchen, Trex decking, new hardscape and paver walkways. Ideally suited for social events, with ample parking and a layout that flows seamlessly from indoors to out.

280 Uplands DR, Hillsborough

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

$11,500,000
5 Beds ⋅ 7 Baths ⋅ ML82052749 MLS
Welcome to 433 El Centro, a newly remodeled luxury estate in Hillsborough. Situated on 0.41 acres, this exceptional property offers refined living designed for entertaining and everyday comfort. The home features 5 bedrooms (including the ADU), 5 full baths, 2 half baths, and a bonus room/den. The gourmet chef's kitchen boasts premium paneled appliances, a wine cooler, and opens to a spacious family room. Additional highlights include built-in speakers, a custom wet bar, dedicated media room, temperature-controlled wine cellar, and laundry rooms on both levels. The luxurious primary suite offers a private office, walk-in closet, and spa-inspired bath with heated floors, towel racks, soaking tub, and dual showers. All secondary bedrooms feature en-suite baths for added comfort and privacy. Designed for seamless indoor-outdoor living, the grounds showcase a pool, spa, fire pit, expansive lawn, outdoor TV, and covered BBQ pavilion with prep space, refrigerator, and ample seating. Conveniently located near top-rated Hillsborough schools, parks, Downtown Burlingame, and transportation, this turnkey estate presents a rare opportunity in one of the Peninsula's most sought-after communities.

433 El Centro RD, Hillsborough

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

$8,038,000
6 Beds ⋅ 4 Baths ⋅ ML82053844 MLS
Located in lower Hillsborough, this custom-made mid-century modern home blends timeless architecture with the effortless California lifestyle. Set behind mature landscaping and surrounded by exceptional privacy, this home is filled with natural light thanks to dramatic walls of glass that blur the line between indoors and out. Every main living space looks onto the backyard landscaping and private pool. The living room, dining room and family room all feature dramatic vaulted ceilings and fireplaces in each room. The flexible floor plan offers six bedrooms and four bathrooms, including a primary suite and various options for an office or work-out space. Rich hardwood floors extend throughout the home. This home captures everything people love about mid-century modern design: open spaces, incredible natural light, seamless indoor-outdoor living and an unmistakable sense of style. All this plus award-winning public schools and perfectly situated between Silicon Valley and San Francisco.

820 Eucalyptus AVE, Hillsborough

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

Sold listing courtesy of Stanley Lo from GRBA
$11,350,000
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

$3,750,000
4 Beds ⋅ 4 Baths ⋅ ML82051481 MLS
Don't Miss the latest updates. Located in a community renowned for exceptional schools, this is a compelling Hillsborough opportunity. Offered at the lowest price per sq. ft. in Hillsborough, it delivers outstanding value in the community & across the Peninsula. Sweeping Bay & San Mateo Bridge views define this home. It features newly painted interiors, hardwood floors & a dramatic great room w/walls of glass overlooking the pool, expansive deck & panoramic viewsan exceptional setting for everyday living & entertaining. Designed for multigenerational living , w/ADU potential, the home offers 2 kitchens, 2 laundry rooms, separate exterior access & living & work-from-home spaces. Main level includes 2 primary suites, powder rm & view kitchen w/stone countertops, generous island, eating area & fireplace. Nearby office offers potential for a 5th BR or primary suite expansion. Lower level includes 2 BRs, full BA, 2nd kit/dining area & flexible bonus room ideal as a 2nd office or craft room. Direct patio, pool & outdoor access makes this level ideal for extended family, guests, caregivers or independent living. Wine cellar, workshop, 2-car garage, oversized driveway & generous storage complete this rare offering w/exceptional views, impressive scale, versatility & unmatched value.

1407 Carlton RD, Hillsborough

Listed by Samia Morgan, 650-678-3633 from eXp Realty of Northern California, Inc.
(If provided) CoList: from

$6,998,000
4 Beds ⋅ 4 Baths ⋅ ML82048818 MLS
Sprawling Privacy Meets Elegant Living Hillsborough Welcome to your private estate, a secluded sanctuary tailored for multi-generational family living & spectacular entertaining. Tucked behind a gated driveway on a premier 2-acre lot, this single-family residence offers a blend of luxury, space, & serenity in one of Hillsboroughs most coveted enclaves. Built in 1974, the home spans a generous 3,230 sq. ft. of living space, beautifully designed to celebrate a seamless indoor-outdoor lifestyle amidst lush landscapes. Step inside to discover a bright, expansive floor plan featuring 4 bedrooms, 3 full bathrooms, and 1 half bathroom. Every room offers room to breathe and space to thrive, with large windows inviting natural light and framing views of the verdant, tree-lined grounds. The crown jewel of this estate is its backyard resort. The sprawling, ultra-private acreage features a sparkling pool and outdoor entertaining spaces, creating an idyllic backdrop for weekend barbecues, sophisticated cocktail parties, or quiet mornings listening to the birds.Here, graceful living meets absolute peace of mind. You are minutes from top-rated schools and world-class dining, yet worlds away from the hustle and bustle. Embrace the pinnacle of Hillsborough luxury. Your private sanctuary awaits.

220 Robin RD, Hillsborough

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

$5,750,000
3 Beds ⋅ 2 Baths ⋅ ML82048610 MLS
Charming single-level home set on an expansive approx. 0.69 acre lot in one of Hillsboroughs most desirable neighborhoods. Privately tucked behind lush landscaping and a gated entrance, this 3-bedroom, 2-bathroom residence offers timeless character, beautiful well-maintained oak hardwood floors, and a inviting layout designed for everyday living and entertaining. The open living and dining areas feature a cozy gas fireplace and picturesque corner windows overlooking the manicured grounds and gardens. The remodeled chefs kitchen is equipped with premium Thermador stainless steel appliances including a 36-inch gas range and refrigerator, beverage fridge, Bosch dishwasher, and sunny breakfast nook. Additional highlights include Marvin windows, updated lighting, Nest thermostat, laundry room, and 2-car garage with EV charger. The outdoor spaces are exceptional with expansive lawns, mature landscaping, spacious entertaining patio, gas fire pit, built-in basketball hoop, in-ground trampoline, and swing set. Ideally located with convenient access to downtown Burlingame, boutique shopping, restaurants, parks, top-rated schools, Highways 280 & 101, and San Francisco International Airport. A rare opportunity to enjoy exceptional indoor-outdoor living in a premier Hillsborough location.

1306 Marlborough RD, Hillsborough

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

Sold listing courtesy of Jenn Gilson from MCGR
$5,900,000
4 Beds ⋅ 4 Baths ⋅ ML82048225 MLS
Set on a half-acre, this beautifully appointed home embodies refined California living, introduced by lush landscaping and a striking column-framed entrance. Inside, nearly 3,500 square feet unfold with dramatic architectural design, where soaring ceilings, exposed beams, and expansive glass create a light-filled, open feel. Hardwood and tile floors span thoughtfully designed spaces, including a stunning living room with a floor-to-ceiling brick fireplace, a dining room with a two-way fireplace, a gourmet kitchen with Gaggenau appliances, and a spacious family room. Four bedrooms, many en suite, include a luxurious primary with a jetted tub and steam shower. The backyard offers a resort-like escape with a pool, lawn, patio, and putting green, all in a private setting near parks, downtown San Mateo, downtown Burlingame, and top schools.

34 Roberts WAY, Hillsborough

Listed by DeLeon Team, 650-300-0888 from Deleon Realty
(If provided) CoList: from

Sold listing courtesy of Eric Chu from SGP
$11,800,000
6 Beds ⋅ 6 Baths ⋅ ML82047705 MLS
Located in desirable lower South Hillsborough, 255 Brentwood offers modern design, vaulted ceilings, exceptional natural light throughout, and seamless indoor-outdoor living. A striking front entry opens to a bright, welcoming foyer, leading into thoughtfully designed living spaces filled with natural light. The open kitchen and dining area serves as the heart of the homeperfect for both everyday living and entertainingfeaturing Miele appliances, two dishwashers, a pantry, and seamless flow to a built-in bar with wine fridge. The main level includes a casual living room, two en-suite bedrooms, and a stunning formal living room wrapped in glass doors and windows with direct access to the backyard. A private elevator connects all levels, offering ease and convenience throughout the home. The lower level offers added flexibility with a bedroom, mudroom, and wine room. Upstairs, the private primary suite features its own balcony, creating a peaceful retreat, while two additional en-suite bedrooms with generous closets complete the level. Outdoor spaces are designed for true California living, featuring a sport court, putting green, outdoor kitchen, sound system, curated lighting, four fireplaces, and beautifully landscaped grounds with a blend of turf and grass.

255 Brentwood RD, Hillsborough

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

Sold listing courtesy of Phil Chen from SGP
$5,600,000
6 Beds ⋅ 8 Baths ⋅ ML82046550 MLS
A rare and irreplaceable work of art. Designed by renowned architect James H. Mitchell in the dramatic Art Deco/Art Moderne tradition, this is one of the Peninsula's most architecturally significant residences. Bold, streamlined geometry and masterful craftsmanship define every elevation of this striking 5,050± sq ft estate, while expansive wraparound decks and architecturally designed terraces off the living room and office invite the outside in, capturing sweeping panoramic views of the Bay, hills, and valley from every room in the home. Situated on a lush 0.71± acre lot, the scale is magnificent and the soul is irreplaceable. A home of genuine artistic pedigree in the heart of Hillsborough's most coveted corridor, near top-ranked schools and effortless Peninsula commuting. Architecture this significant does not come to market twice.

1325 Marlborough RD, Hillsborough

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

Sold listing courtesy of Yvonne Yang from APR
$6,500,000
6 Beds ⋅ 6 Baths ⋅ ML82046653 MLS
Evoking the romance and timeless elegance of classic Spanish Colonial Revival architecture, this enchanting residence welcomes with a sun-drenched brick courtyard framed by lush gardens and climbing bougainvillea. Rich in character, the home showcases exposed wood beams, hand-laid terracotta tile, and artisan-inspired finishes that create a warm yet sophisticated ambiance throughout. Designed for effortless indoor-outdoor living, the expansive courtyard terrace offers multiple gathering spaces ideal for entertaining, quiet mornings, or alfresco dining beneath the canopy of mature landscaping. A sprawling lawn with a grand fountain frame the rear of the property. Charming balconies, arched passageways, and architectural detailing lend an old-world European feel while abundant natural light enhances the homes inviting atmosphere. Inside, the home boasts nearly 6,000 square feet of living space, including multiple separate living quarters perfect for large families, live-in help or guests. Exquisite woodwork and details are abundant throughout the household, with hand-carved fireplaces, curved leaded glass windows, and hand-painted murals. Private, serene, and full of architectural distinction, this is a rare offering that captures the beauty and craftsmanship of a bygone era.

420 El Arroyo RD, Hillsborough

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

Sold listing courtesy of Charles Griffith from MCGR
$5,350,000
3 Beds ⋅ 2 Baths ⋅ ML82046633 MLS
Extremely rare opportunity available to build your dream home on this flat, over-half an acre south facing lot with perimeter foliage and surrounded by estate homes. No trees obstructing the buildable area, Outstanding location surrounded by estate home in lower South Hillsborough, just minutes to Burlingame, top-rated public and private schools and local country clubs. Enjoy the convenience of being located near the San Francisco Airport and Silicon Valley. First time available in 50 +- years.

135 Stonehedge RD, Hillsborough

Listed by Judy Citron, 650-400-8424 from Compass
(If provided) CoList: Talia Citron from Compass

Sold listing courtesy of Geoffrey Nelson from CBR
$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
$6,380,000
4 Beds ⋅ 3 Baths ⋅ ML82043385 MLS
Guest House with full bath, laundry and kitchen on property.

2105 Forest View AVE, Hillsborough

Listed by Emily Smith Silvestri, 650-346-1361 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Christina Ng from APR
$10,750,000
7 Beds ⋅ 6 Baths ⋅ ML82044447 MLS
Modern Sanctuary in Lower South Hillsborough. Welcome to 655 Hayne Road, a newly completed modern residence offering privacy and refined California living in one of Hillsboroughs most desirable neighborhoods. Set behind a gated entrance on a mostly flat, usable parcel, the property is thoughtfully designed for seamless indoor-outdoor living. The main residence flows primarily across a single level, with an open-concept layout that connects effortlessly to the grounds and frames serene treetop views. Positioned just off the main living areas, the attached ADU offers a natural extension of the home, well suited for entertaining, guests, or extended stays. With easy access to the pool and outdoor kitchen, it lives as a cabana-style retreat, enhancing the indoor-outdoor lifestyle. A separate lower-level space offers flexibility for a home theater, gym, or game room. The grounds are carefully composed to create a true sense of escape, blending manicured landscaping, open turf areas, and a natural backdrop. Ideally located just moments from South School and with convenient access to Burlingame, San Mateo, and major commute routes. A rare offering that pairs modern design with usable land in a sought-after Hillsborough setting, ideal for refined indoor-outdoor living.

655 Hayne RD, Hillsborough

Listed by Shaun Walter, 650-727-4888 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Shaun Walter from CBR
$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
$6,400,000
6 Beds ⋅ 6 Baths ⋅ ML82042894 MLS
Step into ultimate luxury with this spacious 6 BD, 5.5 BA home spanning +/- 4,746 SQFT on over 1/2 an acre of beautifully landscaped grounds. Perfect for entertaining and serene living, this home blends a versatile floorplan with thoughtful updates, including a significant 2017-2018 remodel and expansion. The main level is a showstopper, featuring a chef's kitchen with top-tier appliances, an oversized island, and seamless flow to the formal living & dining spaces. Sunlight pours through a wall of windows, framing views of the sparkling pool and lush gardens. This level also offers a private wing with two BDs, a shared BA and an ensuite BD with high ceilings, plus an additional BD, full BA, powder room, laundry room, and interior garage access. Upstairs, two ensuite retreats await, including the primary suite with a spa-like BA, a walk-in closet that dazzles and a 2nd W/D. The lower level living area opens to a tranquil patio & expansive lawn, ideal for outdoor entertaining or quiet mornings. High ceilings, hardwood floors, skylights, fruit trees and modern comforts like A/C, lots of storage and a spacious driveway complete the home. Located in a top-tier school district with easy access to 280 and 92, this home offers the perfect balance of convenience, elegance, and lifestyle.

520 Darrell RD, Hillsborough

Listed by Becky Geller, 415-225-8172 from Compass
(If provided) CoList: from

Sold listing courtesy of Ryan LeDoux from APR
$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
$4,800,000
4 Beds ⋅ 3 Baths ⋅ ML82042683 MLS
Experience the privacy and tranquility of an estate setting, where serene surroundings are complemented by views of San Francisco and the East Bay. A formal entry welcomes you into expansive living and family rooms filled with natural light, highlighted by soaring ceilings and skylights throughout. The well-appointed floor plan features four bedrooms and three baths, including a spacious primary suite with its own private balconyperfect for enjoying the stunning views. The bright kitchen offers a charming breakfast area, ideal for casual dining and everyday living. Outdoors, a grand patio and pool provide an exceptional setting for entertaining or relaxing in complete privacy. Thoughtfully curated landscaping and mature plantings create a lush, picturesque environment, enhancing the homes sense of retreat. Located within the highly regarded Hillsborough school district, this property offers a rare blend of elegance, comfort, and convenience.

965 Parrott DR, Hillsborough

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

Sold listing courtesy of Mary Jo McCarthy from DP
$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
$6,500,000
4 Beds ⋅ 4 Baths ⋅ ML82040481 MLS
Tucked at the end of a private cul-de-sac, 720 Endfield Way offers a rare blend of privacy, scale, and panoramic Bay views. This meticulously maintained all ensuite 4-bedroom, 4-bath residence is filled with natural light. Expansive windows frame stunning vistas from Oakland to the San Mateo Bridge viewed from almost every room. Offering 3779 square feet of generous living spaces for refined entertainment and everyday living, including a family room with wet bar and large primary suite with fireplace, sitting area and walk-in closets. Hardwood floors, updated kitchen with quartz countertops and high end appliances. Cultivated gardens, pool, jacuzzi and dedicated raised vegetable beds are situated on the .75 acre lot. A sprawling view deck provides the perfect setting for sunset dinners, morning coffee, and effortless indoor-outdoor living. Rarely does a home combine such privacy, breathtaking views, and lifestyle appeal in one exceptional setting. Located moments from top-rated schools, Burlingame Avenue, and major commute routes, this is an extraordinary opportunity to experience elevated Peninsula living.

720 Endfield WAY, Hillsborough

Listed by Runa Magowan, 415-412-4480 from Coldwell Banker Realty
(If provided) CoList: Amy Conn from Coldwell Banker Realty

Sold listing courtesy of Serena Conti from APR
$4,550,000
4 Beds ⋅ 3 Baths ⋅ ML82037477 MLS
Tucked away, this graceful single-level home exudes timeless charm and quiet sophistication. Sunlight streams through the windows, highlighting elegant hardwood floors and a thoughtfully designed layout that blends comfort with effortless entertaining. A long paver driveway welcomes guests, while 2 fireplaces provide warmth and a sense of home. The kitchen features double ovens and ample space for cooking and gathering. A separate laundry room with access to the backyard adds practical convenience. Step into the serene primary suite with angled ceilings, built ins, and two true walk in closets, complemented by a junior suite and two additional bedrooms. The primary bath features double sinks, a soaking tub, and a walk-in shower, while 2 additional bathrooms serve the home with ease. Outdoors, the property becomes a private sanctuary with mature trees frame a solar-heated pool. A detached garden or art house with skylight and sink provides a charming space for creativity or reflection, while an adjoining wine room offers the ideal setting for storage and tastings. With nearly 2,800 square feet of living space on a half-acre lot, this Hillsborough home offers a rare combination of elegance, privacy, and enduring appeal in one of the Peninsulas most prestigious communities.

915 Link RD, Hillsborough

Listed by Julie Flouty, 650-504-6900 from Compass
(If provided) CoList: from

Sold listing courtesy of Max Lo from GRBA
$14,500,000
5 Beds ⋅ 8 Baths ⋅ ML82037507 MLS
A beautifully reimagined estate on one of South Hillsborough's most coveted streets. Set behind a private gate and an expansive driveway, this exceptional property pairs timeless architecture with a sophisticated modern remodel. Elegant formal spaces flow effortlessly outdoors, creating a home designed for entertaining. The living room opens to the terrace and gardens, while the dining room, anchored by a sculptural designer fixture, invites memorable alfresco dinners. At the heart of the home, the architectural kitchen and great room showcase a dramatic 14-foot Cristallo island, Viking and Sub-Zero appliances, custom cabinetry, and exposed beam ceilings, all illuminated by striking designer lighting. Five en-suite bedrooms and eight spa-inspired baths are complemented by a media room, gym, two laundry rooms, and five fireplaces throughout. The resort-style grounds offer a pool, jacuzzi, cabana, outdoor kitchen, and multiple terraces, surrounded by mature trees and beautifully layered landscaping. With a solar composite slate roof, EV-charging, new electrical systems, and a new multi-zone HVAC, the home pairs luxury with thoughtful modern infrastructure. Minutes to top Hillsborough schools, Burlingame Avenue, and Burlingame Country Club, this is Hillsborough living at its finest.

729 Chiltern RD, Hillsborough

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

Sold listing courtesy of Austin Herman from APR
$7,106,000
3 Beds ⋅ 4 Baths ⋅ ML82037147 MLS

3 Sherwood CT, Hillsborough

Listed by Chad Krakow, 650-222-7090 from Krakow Company
(If provided) CoList: from

Sold listing courtesy of The Sharp Group from KWPEN
$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

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