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275 Darrell RD, Hillsborough
$3,898,000
4 Beds ⋅ 3 Baths ⋅ ML82066995 MLS
Welcome to a rare opportunity to attain a large and private lot on a quiet cul-de-sac in the prestigious Carolands neighborhood in Hillsborough. Cherish stunning San Francisco Bay views. Picturesque views of the bay from each of the front-facing windows in the home. Open kitchen with built-in double oven, 4-burner gas cooktop and bay windows overlooking the backyard. Formal dining room with lovely backyard views. Separate family room with bay views. Desirable single-story layout. Wonderful primary suite with ensuite bathroom and walk-in closet. Large and private backyard with inviting dining patio, lawn and rose bushes. Nestled on a quiet and walkable cul-de-sac with great privacy and tranquility. Convenient accessibility to exceptional schools, Highway 280 and amenities such as Crystal Springs Golf Course and Downtown Burlingame. Fantastic commute location between Silicon Valley and San Francisco. Award-winning schools: Burlingame High, Crocker Middle and West Hillsborough Elementary.

275 Darrell RD, Hillsborough

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

200 Darrell RD, Hillsborough

2170 Edgecourt DR, Hillsborough
$13,999,000
5 Beds ⋅ 6 Baths ⋅ ML82065828 MLS
MODERN LUXURY, EFFORTLESS CALIFORNIA LIVING Quintessential indoor/outdoor living on a quiet cul-de-sac in lower North Hillsborough.  This custom built modern home at 2170 Edgecourt Drive offers approximately 5,155 square feet of thoughtfully designed living space, with five ensuite bedrooms and five-and-a-half baths. Designed by locally renowned architect Randy Grainge of TRG, the home features an open floor plan along with a dedicated office, a gym, a secondary family room, wet bar with 80-bottle wine refrigerator, complete with designer fixtures and furnishings throughout. Soaring ceilings and walls of glass fill the interiors with natural light and frame backyard views. The outdoor kitchen and pool, built in 2025, create an inviting setting for entertaining and relaxed California living. The home is within walking distance of sought-after North Elementary and Crocker Middle schools. Downtown Burlingame, Highways 101 and 280, and Nueva and Crystal Springs Uplands schools are just minutes away and you are equi-distant from Palo Alto or San Francisco for work or play.

2170 Edgecourt DR, Hillsborough

453 Remillard DR, Hillsborough
$3,690,000
4 Beds ⋅ 3 Baths ⋅ ML82064837 MLS
Recently remodeled throughout, 453 Remillard Drive offers modern living in Hillsborough's desirable Carolands neighborhood. Hardwood floors, recessed lighting and an open floor plan welcome you into a bright great room connecting the living and dining areas with an updated kitchen featuring granite countertops, ample cabinetry, new stainless steel appliances and a breakfast bar. A powder room near the foyer adds convenience. On one side of the home, the upper-level primary suite features high ceilings, a fireplace, private balcony, walk-in closet and an en-suite bath with a double-sink vanity and glass-enclosed shower and tub area. Two bedrooms on the lower level of this same side share a bath; one opens to a deck. Laundry is also on this level. On the opposite side, an upper-level guest suite offers high ceilings, a walk-in closet and private bath, while a spacious family room with high ceilings occupies the lower level on that same side. Multiple decks and generous grounds invite outdoor dining, relaxing and entertaining. Less than a mile from I-280, with West Hillsborough Elementary and Preschool nearby, the home is also a short drive from Sawyer Camp Trail and the scenic Lower Crystal Springs Reservoir. Thoughtfully updated spaces offer comfort style and room to unwind daily.

453 Remillard DR, Hillsborough

910 La Senda RD, Hillsborough
$12,800,000
5 Beds ⋅ 6 Baths ⋅ ML82064121 MLS
Set on a private +/-.81-acre lot with sweeping canyon views, this brand-new contemporary masterpiece offers over 5,600s.f. of sunlit living space. Designed for sophisticated living and entertaining, the home blends dramatic architecture, refined finishes, and seamless indoor/outdoor spaces. Five generously sized bedroom suites, a half bath, and office/study are thoughtfully positioned throughout. The formal living room features a dramatic fireplace and expansive glass walls that frame the spectacular scenery. An elegant dining room provides an exceptional setting for both casual dinners and grand-scale entertaining. At the heart of the home, the chef's kitchen features Miele appliances, custom cabinetry, and center island. The massive adjoining family room also opens directly to a vast, covered entertaining deck overlooking breathtaking views, creating an ideal setting for gatherings. The lower level offers a private suite with a spa-like bath, sauna, media/recreation room, wine displays, wet bar, and rear yard access. The stunning grounds feature level lawns, vanishing-edge fountain, & multiple viewing terraces. A gated driveway, A/C, radiant heat, & EV outlet complete this offering. An exceptional combination of privacy, luxury, architectural distinction, and breathtaking views

910 La Senda RD, Hillsborough

950 Macadamia DR, Hillsborough
$26,000,000
6 Beds ⋅ 10 Baths ⋅ ML82063278 MLS
Modern luxury meets sweeping San Francisco Bay views at 950 Macadamia. Designed by TRG Architects and built in 2021, this estate sits on 1.25 acres in Hillsboroughs sought-after Skyfarm neighborhood, offering approximately 10,888 square feet across three levels, with 6 bedrooms, 8 full baths, and 2 half baths. Clean architectural lines, custom European finishes, and expansive walls of glass fill the home with natural light and capture views throughout. The open living spaces center around a chefs kitchen with Miele appliances, while expansive glass doors open to spacious terraces for seamless indoor-outdoor living. An infinity-edge pool and spa, outdoor kitchen, fireplace, and beautifully landscaped grounds create a private resort setting for entertaining or relaxing at home. The lower level features a home theater, game room with bar, gym, steam room, and sauna. A private guest suite with a full kitchen and separate entrance offers added comfort and flexibility. An office, wine cellar, elevator, six-car garage, solar panels, and smart home automation complete the home. With its striking design, expansive views, and exceptional amenities, 950 Macadamia brings together the best of modern Hillsborough living.

950 Macadamia DR, Hillsborough

85 Fagan DR, Hillsborough
$39,000,000
9 Beds ⋅ 7 Baths ⋅ ML82062082 MLS
*NEW PRICE INCLUDES 85 FAGAN & ADJACENT EMPTY LOT 90 FAGAN (.902 ACRES) FOR THE ULTIMATE PRIVATE RETREAT* GRANDEUR. MODERN LUXURY. OVER 3 ACRES + NEW ADU + EXTENSIVELY MODERNIZED, A rare Hillsborough estate where irreplaceable old-world craftsmanship meets today's technology and comfort. Extensively modernized with a new kitchen, updated baths, new heating and air conditioning, generator, and sophisticated smart-home systems. Hundreds of LED lights, gates, climate, security and other home functions can be controlled remotely.**The craftsmanship of yesterday beautifully preserved. The technology and comfort of today already done** DON'T LET THE AGE FOOL YOU. THIS IS A HISTORIC MASTERPIECE REIMAGINED FOR MODERN LIVING.

85 Fagan DR, Hillsborough

30 Bluebell LN, Hillsborough
$4,087,000
4 Beds ⋅ 4 Baths ⋅ ML82053624 MLS
Perched in the prestigious Lakeview neighborhood of Hillsborough, this gated residence blends refined living with breathtaking design and panoramic views. A spacious motor court and two-car garage welcome you to a home of distinction. Step into the elegant foyer, where classic columns frame a soaring open-concept living area. Vaulted ceilings with exposed beams and floor-to-ceiling windows flood the space with natural light and showcase sweeping vistas. The expansive living room features a dramatic stone fireplace and flows into a chefs kitchen with high-end stainless steel appliances, tray ceiling, and a generous breakfast barperfect for everyday living and entertaining. This four-bedroom home includes a luxurious primary suite with a private sitting area and spa-inspired bath, complete with soaking tub, frameless glass shower, and double vanity. Located in the serene Lakeview area near top-rated schools, boutique shopping, and dining, with easy access to Hwy 280, 101, SF, Silicon Valley, and SFO. The land has potential for subdivision, subject to city approval.

30 Bluebell LN, Hillsborough

150 New Place RD, Hillsborough
$48,888,000
10 Beds ⋅ 10 Baths ⋅ ML82059451 MLS
A landmark Hillsborough estate of extraordinary scale, privacy, and unparalleled distinction, nestled within the exclusive New Place Road enclave, historically associated with the Gilded Age-era William H. Crocker estate. Arrival begins at the historic William H. Crocker gate posts marking the entrance to New Place Road, winding through the fairways of Burlingame Country Club. 150 New Place Road is an exceptional compound offering refined California living. Private resort-caliber grounds offer gathering areas for relaxation and elegant entertaining in complete privacy. A private detached guest house, panoramic San Francisco Bay views, swimming pool, private tennis and pickleball court, and comprehensive whole-home systems. Sophisticated interior living spaces, generous bedroom suites, theatre room and indoor sauna provide exceptional comfort and recreation. Walls of glass and expansive terraces frame breathtaking San Francisco Bay views and invite seamless indoor-outdoor living. Ideally positioned near San Francisco, Silicon Valley, SFO, and the Peninsula's renowned schools and amenities. Offered at $48,888,000, 150 New Place is an exceptionally rare Hillsborough trophy estate- a landmark private compound where privacy, scale, setting, and a sense of history converge

150 New Place RD, Hillsborough

68 Eugenia Way, Hillsborough
$5,300,000
ML82056669 MLS
Land + Fully Approved Shovel-Ready Plans Included in the Price. An extraordinary opportunity to build a landmark luxury estate in Hillsborough's prestigious Skyfarm neighborhood. Set on a private 28,648± sf (0.66± acre) parcel, the offering includes plans for an approximately 7,916 sf contemporary residence with 5 bedrooms, 6 full baths, and 1 half bath (per approved plans: gross floor area across three levels totals 8,600 sf [2,609+4,000+1,991], less the 824 sf garage, plus +140 sf of stairs = 7,916 sf ). Designed by AIA award-winning architect Leonard Ng (LNAI Architecture). Designed by an award-winning architect, the design blends timeless elegance with modern sophistication; expansive glass walls, soaring ceilings, and seamless indoor-outdoor living create a light-filled retreat that embraces the natural landscape. Dramatic terraces and an infinity-edge pool and spa appear to float above the hillside for a true resort-inspired setting. The plan includes grand living and entertaining spaces, a temperature-controlled wine room, home theater, and luxurious primary suite. Plans have completed ADRB Formal Review with the Town of Hillsborough, streamlining the path to permit and construction to build a one-of-a-kind estate in one of the Peninsula's most prestigious neighborhoods.

68 Eugenia Way, Hillsborough

2155 Geri LN, Hillsborough
$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

433 El Centro RD, Hillsborough
$11,000,000
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

90 Fagan DR, Hillsborough
$8,990,000
ML82034335 MLS
A RARE ONCE-IN-A-LIFETIME LOT RARELY SEEN IN THIS NEIGHBORHOOD! BUILD YOUR DREAM HOME! PRIME LOWER HILLSBOROUGH LOCATION WITH .90 ACRES OF MOSTLY USABLE LAND! NEWLY RENOVATED POWERFUL WATER WELL!!!! SAVE ON YOUR WATER BILLS WHEN WATERING YOUR GARDENS! YOU WILL NOT FIND A BETTER CHOICE THAN THIS CURRENTLY IN HILLSBOROUGH, AND THINGS THIS GOOD ONLY POP UP ONCE IN A BLUE MOON!!! Located at the end of an exclusive cul-de-sac in the prestigious historic Fagan Estates subdivision. This lot features A WIDE SPRAWLING GREEN LAWN with almost an acre of pristine land! Encompassed by an abundance of mature trees offering total privacy. Only .5 miles walking distance to bustling Downtown Burlingame. The lot offers the perfect canvas to get everything you've dreamed about with only your imagination being the limit. ONCE-IN-A-LIFETIME OPPORTUNITY, RARE LISTING, AND MORE! (Images of houses are digitally altered renderings used solely to illustrate potential use of the space. No plans have been prepared, submitted, or approved by the City of Hillsborough, and no consultants or experts have been engaged to evaluate feasibility. There is no house on the lot)

90 Fagan DR, Hillsborough

2930 Privet DR, Hillsborough
$9,800,000
7 Beds ⋅ 8 Baths ⋅ ML82032512 MLS
Set behind private gates on a 0.645-acre parcel in Hillsborough's prestigious neighborhood, this 9,035 sq ft estate offers sweeping San Francisco Bay views & exceptional scale. A grand double-door entry opens to a dramatic foyer with a stained-glass dome skylight, leading to an expansive main level defined by floor-to-ceiling glass and abundant natural light. Custom coved & vaulted tray ceilings with architectural pillars enhance the living room, formal dining room, and family room, all unified by rich hardwood floors. Refined details include stained glass accents, skylights, crown molding, wainscoting, recessed lighting, and a multi-room audio system. The formal living and dining rooms feature fireplaces, with roof deck access ideal for entertaining. The family room includes a custom wet bar with wine cooler and built-ins. The chef's kitchen offers granite counters, center island, pantry, high-end appliances, and breakfast nook. The main level includes a paneled office, powder rooms, laundry, garage access, and a spacious primary suite. The lower level offers six additional bedrooms, staff quarters, wine cellars, a second kitchen, and access to a glass-enclosed indoor pool with spa. Expansive patios, synthetic lawn, walking paths, and motor court.

2930 Privet DR, Hillsborough

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