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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.

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

Listed by David Lillo, 408-621-5649 from DPL Real Estate
(If provided) CoList: from

$5,488,000

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.

5 Beds ⋅ 5 Baths ⋅ ML82066167 MLS

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

200 Darrell RD, Hillsborough

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

$13,999,000

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.

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

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

$8,250,000

A rare Lower Hillsborough opportunity awaits at 701 Chester Way, an extraordinary 40,083-square-foot property that has been held by the same family for 52 years. Originally built in 1917, this approximately 8,170-square-foot Mediterranean-style residence offers eight bedrooms, 6.5 baths, a four-car garage, swimming pool, and squash court. While the residence presents some deferred maintenance, its remarkable scale, expansive grounds, sought-after Lower Hillsborough location, and long private approach create an exceptional canvas for restoration, renovation, or a visionary redevelopment plan, subject to applicable approvals and buyer investigation.

8 Beds ⋅ 7 Baths ⋅ ML82065500 MLS

A rare Lower Hillsborough opportunity awaits at 701 Chester Way, an extraordinary 40,083-square-foot property that has been held by the same family for 52 years. Originally built in 1917, this approximately 8,170-square-foot Mediterranean-style residence offers eight bedrooms, 6.5 baths, a four-car garage, swimming pool, and squash court. While the residence presents some deferred maintenance, its remarkable scale, expansive grounds, sought-after Lower Hillsborough location, and long private approach create an exceptional canvas for restoration, renovation, or a visionary redevelopment plan, subject to applicable approvals and buyer investigation.

701 Chester WAY, Hillsborough

Listed by Jose Dos Ramos, 650-787-5568 from Berkshire Hathaway HomeServices Drysdale Propertie
(If provided) CoList: from

Sold listing courtesy of Cullinan Luxury from KWPEN

$8,314,900

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

5 Beds ⋅ 5 Baths ⋅ ML82064709 MLS

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

501 El Cerrito AVE, Hillsborough

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

Sold listing courtesy of Jim Arbeed from CBR

$4,750,000

Located in one of Hillsborough's desirable residential neighborhoods, this approximately 3,570-square-foot residence sits on a generous 18,344-square-foot lot. Offering an exceptional opportunity in an established Hillsborough setting, the property was sold off-market and entered into the MLS for comparable purposes only.

4 Beds ⋅ 3 Baths ⋅ ML82065236 MLS

Located in one of Hillsborough's desirable residential neighborhoods, this approximately 3,570-square-foot residence sits on a generous 18,344-square-foot lot. Offering an exceptional opportunity in an established Hillsborough setting, the property was sold off-market and entered into the MLS for comparable purposes only.

25 Annescourt PL, Hillsborough

Listed by Alexandra Gilmartin, 650-454-0575 from Gilmartin Group
(If provided) CoList: Maureen Gilmartin from Gilmartin Group

Sold listing courtesy of Stephan A. Marshall from SGP

$3,690,000

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.

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

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

$12,800,000

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

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

Listed by Jim Arbeed, (650) 430-7653 from Coldwell Banker Realty
(If provided) CoList: from

$12,500,000

5 Beds ⋅ 6 Baths ⋅ ML82064115 MLS

1545 Bellevue AVE, Hillsborough

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

Sold listing courtesy of Elizabeth Elliott Maulick from APR

$4,500,000

Set on approximately 0.62 acres in desirable Lower South Hillsborough, this inviting ranch-style residence offers an exceptional combination of privacy, space, convenience, and tremendous potential. The home features three bedrooms and two-and-a-half bathrooms, with beautiful hardwood floors, freshly painted interiors, and newly refinished flooring creating a bright and welcoming backdrop. A generously sized family room and separate dining room both open directly to the expansive backyard, providing wonderful indoor-outdoor flow and effortless access to the patio and lawn. The private grounds are a standout feature, offering a large outdoor patio, expansive grassy areas, and ample room to reimagine the property over time. The generous lot also provides potential for an ADU or additional improvements, subject to applicable approvals. A two-car garage plus additional carport provides excellent parking and storage. Ideally situated in Lower South Hillsborough, the property enjoys convenient access to South School, Crystal Springs Uplands School, downtown San Mateo, shopping, dining, and major commute routes.

3 Beds ⋅ 3 Baths ⋅ ML82063576 MLS

Set on approximately 0.62 acres in desirable Lower South Hillsborough, this inviting ranch-style residence offers an exceptional combination of privacy, space, convenience, and tremendous potential. The home features three bedrooms and two-and-a-half bathrooms, with beautiful hardwood floors, freshly painted interiors, and newly refinished flooring creating a bright and welcoming backdrop. A generously sized family room and separate dining room both open directly to the expansive backyard, providing wonderful indoor-outdoor flow and effortless access to the patio and lawn. The private grounds are a standout feature, offering a large outdoor patio, expansive grassy areas, and ample room to reimagine the property over time. The generous lot also provides potential for an ADU or additional improvements, subject to applicable approvals. A two-car garage plus additional carport provides excellent parking and storage. Ideally situated in Lower South Hillsborough, the property enjoys convenient access to South School, Crystal Springs Uplands School, downtown San Mateo, shopping, dining, and major commute routes.

140 Rockridge RD, Hillsborough

Listed by Emma Elfving, 650-773-5115 from Compass
(If provided) CoList: from

Sold listing courtesy of Bijan Amini from QSTRE

$26,000,000

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.

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

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

$19,500,000

New construction in progress and will be completed in Mid 2027. This is An exceptional new estate in coveted Lower North Hillsborough.

5 Beds ⋅ 7 Baths ⋅ ML82062674 MLS

New construction in progress and will be completed in Mid 2027. This is An exceptional new estate in coveted Lower North Hillsborough.

2265 Ralston AVE, Hillsborough

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

$6,000,000

This gated Hillsborough estate commands one of the finest views in town. Sweeping San Francisco vistas from the living room, dining room, and kitchen even dishwashing becomes a moment to savor as city lights twinkle! The expansive main deck one of four throughout the home provides views stretching from San Francisco to San Mateo and beyond. The primary suite offers a walk-in dressing room and spa-like bathroom, joined by two additional en-suite bedrooms and a versatile bonus room, currently staged as a 4th bedroom with sitting area. A 2-car attached garage with private gated entry completes this rare offering where every day is a room with a view! All that, plus award-winning schools, close to San Francisco and Silicon Valley and minutes to 92, 101 and 280.

3 Beds ⋅ 4 Baths ⋅ ML82062299 MLS

This gated Hillsborough estate commands one of the finest views in town. Sweeping San Francisco vistas from the living room, dining room, and kitchen even dishwashing becomes a moment to savor as city lights twinkle! The expansive main deck one of four throughout the home provides views stretching from San Francisco to San Mateo and beyond. The primary suite offers a walk-in dressing room and spa-like bathroom, joined by two additional en-suite bedrooms and a versatile bonus room, currently staged as a 4th bedroom with sitting area. A 2-car attached garage with private gated entry completes this rare offering where every day is a room with a view! All that, plus award-winning schools, close to San Francisco and Silicon Valley and minutes to 92, 101 and 280.

100 Southdown CT, Hillsborough

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

Sold listing courtesy of Tammi Michael from APR

$39,000,000

*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.

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

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

$6,175,000

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

5 Beds ⋅ 5 Baths ⋅ ML82061953 MLS

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

40 Eugenia WAY, Hillsborough

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

Sold listing courtesy of Jenn Gilson from MCGR

$4,087,000

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.

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

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

$5,800,000

Set on a private, gated .86 acres of stunningly landscaped grounds, this exceptional contemporary residence was extensively remodeled to perfection in 2017. Floor-to-ceiling glass walls throughout fill the interior spaces with natural light and create a seamless connection to the serene outdoors. A gracious foyer leads to an elegant living and dining room ensemble wrapped in walls of glass, with a chic fireplace adding warmth and intimacy. The amazing chefs kitchen is anchored by a dramatic center island, ample cabinetry, and generous counter space. Huge sliding glass doors open to a large deck, creating an idyllic setting for morning coffee, dining, or relaxed entertaining. The primary suite features an expansive glass wall with sliding door, a romantic fireplace, huge walk-in closet, and remote-controlled blinds. Two additional bedrooms with dedicated bathrooms offer flexibility, with one beautifully arranged as an office with custom cabinetry and desks. Outside, majestic trees, meandering creek, incredible landscaping, expansive synthetic turf, and wrap-around decking create a truly magical park setting. Extending from El Cerrito to Rockridge Drive, this property offers a rare sanctuary where architecture, light, landscape, and contemporary luxury exist in effortless harmony.

3 Beds ⋅ 3 Baths ⋅ ML82061884 MLS

Set on a private, gated .86 acres of stunningly landscaped grounds, this exceptional contemporary residence was extensively remodeled to perfection in 2017. Floor-to-ceiling glass walls throughout fill the interior spaces with natural light and create a seamless connection to the serene outdoors. A gracious foyer leads to an elegant living and dining room ensemble wrapped in walls of glass, with a chic fireplace adding warmth and intimacy. The amazing chefs kitchen is anchored by a dramatic center island, ample cabinetry, and generous counter space. Huge sliding glass doors open to a large deck, creating an idyllic setting for morning coffee, dining, or relaxed entertaining. The primary suite features an expansive glass wall with sliding door, a romantic fireplace, huge walk-in closet, and remote-controlled blinds. Two additional bedrooms with dedicated bathrooms offer flexibility, with one beautifully arranged as an office with custom cabinetry and desks. Outside, majestic trees, meandering creek, incredible landscaping, expansive synthetic turf, and wrap-around decking create a truly magical park setting. Extending from El Cerrito to Rockridge Drive, this property offers a rare sanctuary where architecture, light, landscape, and contemporary luxury exist in effortless harmony.

739 El Cerrito AVE, Hillsborough

Listed by Jim Arbeed, 650-558-4248 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Cortney Laugesen from KWPEN

$4,168,000

Owned since new, offered for the first time since 1976, this exceptional home represents a rare opportunity more than five decades in the making. Set behind a gated driveway amid beautifully landscaped grounds, distinguished by its single-level design & connection to the outdoors. The thoughtfully designed floor plan features 4 bedrooms & 2.5 bathrooms, elegant living & dining rooms, a light-filled family room w/vaulted ceiling, kitchen with breakfast nook, & a spacious primary suite. A defining feature is the dramatic sunroom extending across the rear of the home. Accessible from the family room, breakfast area, & primary suite, walls & ceiling of glass overlook the swimming pool, deck, mature trees, & surrounding greenery. Beautifully established grounds feature sweeping lawns, mature landscaping, a swimming pool, recreation court, expansive deck, three-car garage, & generous parking - an inviting setting for relaxation and entertaining. A separate lower-level bonus area with a bedroom, bathroom, & living room provides flexibility for guests, a home office, or recreation. With its privacy, single-level living, indoor-outdoor connection, & impressive grounds, this distinctive home offers a rare opportunity to enjoy Hillsborough living & envision its possibilities for the future.

4 Beds ⋅ 3 Baths ⋅ ML82061870 MLS

Owned since new, offered for the first time since 1976, this exceptional home represents a rare opportunity more than five decades in the making. Set behind a gated driveway amid beautifully landscaped grounds, distinguished by its single-level design & connection to the outdoors. The thoughtfully designed floor plan features 4 bedrooms & 2.5 bathrooms, elegant living & dining rooms, a light-filled family room w/vaulted ceiling, kitchen with breakfast nook, & a spacious primary suite. A defining feature is the dramatic sunroom extending across the rear of the home. Accessible from the family room, breakfast area, & primary suite, walls & ceiling of glass overlook the swimming pool, deck, mature trees, & surrounding greenery. Beautifully established grounds feature sweeping lawns, mature landscaping, a swimming pool, recreation court, expansive deck, three-car garage, & generous parking - an inviting setting for relaxation and entertaining. A separate lower-level bonus area with a bedroom, bathroom, & living room provides flexibility for guests, a home office, or recreation. With its privacy, single-level living, indoor-outdoor connection, & impressive grounds, this distinctive home offers a rare opportunity to enjoy Hillsborough living & envision its possibilities for the future.

1345 Lakeview DR, Hillsborough

Listed by Henry Chu, 650-918-8118 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Jennie Lok from RBT

$6,150,000

HILLSBOROUGH'S TOP LOCATION! This rare and exceptional Mid-Century Modern architectural gem, designed in 1958 by acclaimed architect Charles Bolton White, is tucked away on one of Lower South Hillsboroughs most private and sought-after cul-de-sacs, with just three homes on the court. Set on a mostly level, sun-filled half acre, this graceful 6-bedroom, 4-bath residence is surrounded by Japanese-inspired gardens, graceful maples, mature oaks and towering redwoods, creating a serene, park-like setting. Designed for architecture and nature to exist in perfect harmony, the home features soaring ceilings, walls of windows opening to the rear gardens, warm redwood walls, a spacious family room and generously sized bedrooms. The private primary suite enjoys beautiful pool and garden views and an ensuite bath. Outdoors, a sparkling pool, expansive entertaining patios and generous level play areas capture quintessential indoor-outdoor California living. A separate fruit-tree meadow offers added privacy and an ideal setting for a future ADU. Meticulously maintained and beautifully preserved, this extraordinary Hillsborough residence is ready for its next chapter.

6 Beds ⋅ 4 Baths ⋅ ML82061801 MLS

HILLSBOROUGH'S TOP LOCATION! This rare and exceptional Mid-Century Modern architectural gem, designed in 1958 by acclaimed architect Charles Bolton White, is tucked away on one of Lower South Hillsboroughs most private and sought-after cul-de-sacs, with just three homes on the court. Set on a mostly level, sun-filled half acre, this graceful 6-bedroom, 4-bath residence is surrounded by Japanese-inspired gardens, graceful maples, mature oaks and towering redwoods, creating a serene, park-like setting. Designed for architecture and nature to exist in perfect harmony, the home features soaring ceilings, walls of windows opening to the rear gardens, warm redwood walls, a spacious family room and generously sized bedrooms. The private primary suite enjoys beautiful pool and garden views and an ensuite bath. Outdoors, a sparkling pool, expansive entertaining patios and generous level play areas capture quintessential indoor-outdoor California living. A separate fruit-tree meadow offers added privacy and an ideal setting for a future ADU. Meticulously maintained and beautifully preserved, this extraordinary Hillsborough residence is ready for its next chapter.

15 Mc Kenzie CT, Hillsborough

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

Sold listing courtesy of Laura Bryant from KWPEN

$6,150,000

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

5 Beds ⋅ 5 Baths ⋅ ML82060425 MLS

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

860 Longview RD, Hillsborough

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

Sold listing courtesy of Heather Hansen from APR

$4,700,000

4 Beds ⋅ 3 Baths ⋅ ML82059590 MLS

1520 Tartan Trail 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

$48,888,000

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

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

Listed by Mary Bee, 650-343-9999 from Intero Real Estate Services
(If provided) CoList: from

$4,500,000

Tucked away on a peaceful cul-de-sac just moments from Vista Park, this Chuck Winslow-designed residence masterfully blends the warmth and romance of an Italian villa with refined California living. A dramatic living room welcomes guests with soaring 10-foot ceilings, exposed mahogany beams, rich inlaid hardwood floors, and walls of French doors that frame the sun-drenched pool courtyard, seamlessly blending indoor and outdoor living. At the heart of the home is a truly one-of-a-kind gourmet kitchen inspired by Henri Matisse's celebrated Jazz series. Outdoor living is equally exceptional, with an enclosed courtyard centering around a poured swimming pool and outdoor fireplace. A residence of uncommon character and enduring elegance, this is a home where architecture, art, comfort, and lifestyle come together to create one of Hillsborough's truly distinctive offerings.

4 Beds ⋅ 3 Baths ⋅ ML82058818 MLS

Tucked away on a peaceful cul-de-sac just moments from Vista Park, this Chuck Winslow-designed residence masterfully blends the warmth and romance of an Italian villa with refined California living. A dramatic living room welcomes guests with soaring 10-foot ceilings, exposed mahogany beams, rich inlaid hardwood floors, and walls of French doors that frame the sun-drenched pool courtyard, seamlessly blending indoor and outdoor living. At the heart of the home is a truly one-of-a-kind gourmet kitchen inspired by Henri Matisse's celebrated Jazz series. Outdoor living is equally exceptional, with an enclosed courtyard centering around a poured swimming pool and outdoor fireplace. A residence of uncommon character and enduring elegance, this is a home where architecture, art, comfort, and lifestyle come together to create one of Hillsborough's truly distinctive offerings.

1032 La Cuesta RD, Hillsborough

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

Sold listing courtesy of Rachel DiNapoli from DWELL

$7,100,000

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

4 Beds ⋅ 5 Baths ⋅ ML82058766 MLS

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

2801 Easton DR, Hillsborough

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

Sold listing courtesy of Jason Liu from FQLT

$18,770,000

This English Tudor set on over one flat acre in prime lower North Hillsborough is surrounded by three sides of the Burlingame Country Club Golf Course, making it one of the areas most iconic estates. This fully custom private gated architectural masterpiece is the epitome of California living. Constructed in 2005 with many recent improvements including a remodeled kitchen, refinished floors throughout, updated light fixtures & new landscaping that blend old-world charm with modern aesthetics to create an immediate sense of arrival upon entering.An entertainer's dream, this property features formal rooms and multiple entertaining spaces on both floors. The 6 bedrooms and 7 full bathrooms are thoughtfully designed with a primary bedroom on each level. The French doors throughout create the ultimate indoor-outdoor flow as they lead to the resort style backyard that is complemented by a pool house with a full bath. The backyard features a stunning Pebbletec pool with dual waterfall and a separate spa. The lush landscaping lends privacy to the property and creates a park like setting throughout with the serene courtyard and garden walking path. This property is walking distance to Burlingame Avenue and one block to North Elementary and Crocker Middle School.

6 Beds ⋅ 9 Baths ⋅ ML82057167 MLS

This English Tudor set on over one flat acre in prime lower North Hillsborough is surrounded by three sides of the Burlingame Country Club Golf Course, making it one of the areas most iconic estates. This fully custom private gated architectural masterpiece is the epitome of California living. Constructed in 2005 with many recent improvements including a remodeled kitchen, refinished floors throughout, updated light fixtures & new landscaping that blend old-world charm with modern aesthetics to create an immediate sense of arrival upon entering.An entertainer's dream, this property features formal rooms and multiple entertaining spaces on both floors. The 6 bedrooms and 7 full bathrooms are thoughtfully designed with a primary bedroom on each level. The French doors throughout create the ultimate indoor-outdoor flow as they lead to the resort style backyard that is complemented by a pool house with a full bath. The backyard features a stunning Pebbletec pool with dual waterfall and a separate spa. The lush landscaping lends privacy to the property and creates a park like setting throughout with the serene courtyard and garden walking path. This property is walking distance to Burlingame Avenue and one block to North Elementary and Crocker Middle School.

600 Eucalyptus AVE, Hillsborough

Listed by Joseph Miller, 650-455-6552 from Miller/Steil Properties
(If provided) CoList: Chelsea Miller from Miller/Steil Properties

Sold listing courtesy of Stanley Lo from GRBA

$10,300,000

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.

6 Beds ⋅ 5 Baths ⋅ ML82057038 MLS

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

19 Farm LN, Hillsborough

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

Sold listing courtesy of Michele Oravec from APR

$4,400,000

Nestled in Hillsborough's prestigious Skyfarm neighborhood, this expansive single-level residence sits on an exceptionally private half-acre lot with sweeping panoramic Bay views and extraordinary potential. Thoughtfully designed for comfortable living and effortless entertaining, the home features four generously sized bedrooms, three-and-one-half bathrooms, soaring vaulted ceilings, floor-to-ceiling windows, rich hardwood flooring, and a wood-burning fireplace. The well-appointed kitchen offers picturesque Bay views, a breakfast bar, and an adjoining breakfast room, while a separate office provides an ideal work-from-home space. Outside, the sprawling grounds showcase a sparkling pool, remarkable privacy, and an expansive backyard with endless possibilities for a sport court, gardens, outdoor entertaining, or a future ADU or guest house (buyer to verify). Additional highlights include owned solar, a spacious three-car garage, abundant storage, and a highly desirable single-level floor plan. Combining timeless architecture, breathtaking views, exceptional privacy, and incredible opportunity, this is a rare chance to personalize a premier property in one of Hillsborough's most coveted neighborhoods.

4 Beds ⋅ 4 Baths ⋅ ML82056870 MLS

Nestled in Hillsborough's prestigious Skyfarm neighborhood, this expansive single-level residence sits on an exceptionally private half-acre lot with sweeping panoramic Bay views and extraordinary potential. Thoughtfully designed for comfortable living and effortless entertaining, the home features four generously sized bedrooms, three-and-one-half bathrooms, soaring vaulted ceilings, floor-to-ceiling windows, rich hardwood flooring, and a wood-burning fireplace. The well-appointed kitchen offers picturesque Bay views, a breakfast bar, and an adjoining breakfast room, while a separate office provides an ideal work-from-home space. Outside, the sprawling grounds showcase a sparkling pool, remarkable privacy, and an expansive backyard with endless possibilities for a sport court, gardens, outdoor entertaining, or a future ADU or guest house (buyer to verify). Additional highlights include owned solar, a spacious three-car garage, abundant storage, and a highly desirable single-level floor plan. Combining timeless architecture, breathtaking views, exceptional privacy, and incredible opportunity, this is a rare chance to personalize a premier property in one of Hillsborough's most coveted neighborhoods.

35 Silk Tree PL, Hillsborough

Listed by Emma Elfving, 650-773-5115 from Compass
(If provided) CoList: Erik Elfving from Compass

Sold listing courtesy of Julie Boc from SGP

$5,300,000

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.

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

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

$12,019,880

Extraordinary gardens and complete privacy create one of South Hillsborough's most exceptional residences. This circa 1931 Spanish Hacienda home presents a compelling blend of enduring architecture and recently completed updates. Surrounding this gated estate are approximately 2.55 acres of park-like grounds with a separate guest home, cabana, pool, spa and sports court. Signature details of the era remain beautifully intact, from vaulted ceilings, Gothic arched doorways, and all-wood beamed ceilings. Recent improvements introduce a fresh aesthetic, including a remodeled designer kitchen and service area, updated lighting, and refinished hardwood floors. The home balances impressive scale with comfortable livability through a collection of elegant formal rooms, a dedicated office, a tremendous kitchen and family room combination, and lower-level spaces for fitness and staff accommodations. The 5 bedrooms and 5.5 baths in the main residence are complemented by a detached one bedroom guest house plus a pool cabana, while the grounds unfold with meandering pathways, mature trees, and abundant privacy. Bay views from the primary suite add another dimension to this distinguished Hillsborough estate.

6 Beds ⋅ 7 Baths ⋅ ML82055882 MLS

Extraordinary gardens and complete privacy create one of South Hillsborough's most exceptional residences. This circa 1931 Spanish Hacienda home presents a compelling blend of enduring architecture and recently completed updates. Surrounding this gated estate are approximately 2.55 acres of park-like grounds with a separate guest home, cabana, pool, spa and sports court. Signature details of the era remain beautifully intact, from vaulted ceilings, Gothic arched doorways, and all-wood beamed ceilings. Recent improvements introduce a fresh aesthetic, including a remodeled designer kitchen and service area, updated lighting, and refinished hardwood floors. The home balances impressive scale with comfortable livability through a collection of elegant formal rooms, a dedicated office, a tremendous kitchen and family room combination, and lower-level spaces for fitness and staff accommodations. The 5 bedrooms and 5.5 baths in the main residence are complemented by a detached one bedroom guest house plus a pool cabana, while the grounds unfold with meandering pathways, mature trees, and abundant privacy. Bay views from the primary suite add another dimension to this distinguished Hillsborough estate.

862 Chiltern RD, Hillsborough

Listed by Lori Buecheler, 650-387-2716 from Compass
(If provided) CoList: Olivia Maggi from Compass

Sold listing courtesy of Gary Johnson from COMP

$8,999,000

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!!!

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

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