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$5,995,000

Offered for the first time in over 40 years, this iconic Hillsborough estate presents a rare opportunity to own a piece of local history. Set within the coveted Lakeview neighborhood on a private cul-de-sac, the home is thoughtfully designed to embrace its breathtaking surroundings, where panoramic Bay and canyon views are showcased through dramatic walls of windows and enjoyed from multiple view decks. Light-filled interiors offer seamless indoor/outdoor living with expansive gathering spaces, four bedrooms, each with an en suite bathroom, a fitness/yoga studio with sauna, and a dedicated media room ready to become the ultimate home theater. Set on an expansive 25,000± sq. ft. lot with over 7,000 sq. ft. of living space, this timeless estate blends privacy, scale, and natural beauty. Ideally located between San Francisco and Silicon Valley, just minutes from SFO, Highway 280, and top-rated public and private schools. A truly rare opportunity to call one of the Peninsula's most prestigious neighborhoods home.

4 Beds ⋅ 7 Baths ⋅ ML82054112 MLS

Offered for the first time in over 40 years, this iconic Hillsborough estate presents a rare opportunity to own a piece of local history. Set within the coveted Lakeview neighborhood on a private cul-de-sac, the home is thoughtfully designed to embrace its breathtaking surroundings, where panoramic Bay and canyon views are showcased through dramatic walls of windows and enjoyed from multiple view decks. Light-filled interiors offer seamless indoor/outdoor living with expansive gathering spaces, four bedrooms, each with an en suite bathroom, a fitness/yoga studio with sauna, and a dedicated media room ready to become the ultimate home theater. Set on an expansive 25,000± sq. ft. lot with over 7,000 sq. ft. of living space, this timeless estate blends privacy, scale, and natural beauty. Ideally located between San Francisco and Silicon Valley, just minutes from SFO, Highway 280, and top-rated public and private schools. A truly rare opportunity to call one of the Peninsula's most prestigious neighborhoods home.

95 Southdown CT, Hillsborough

Listed by Madelyn Brown, 408-761-7776 from KW Bay Area Estates
(If provided) CoList: Scott C. Poncetta from KW Bay Area Estates

$3,750,000

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. Recently refreshed & updated, 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.

4 Beds ⋅ 4 Baths ⋅ ML82051481 MLS

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. Recently refreshed & updated, 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

$4,000,000

A rare opportunity to develop a pristine piece of residential land in one of California's most sought after luxury housing markets. The Meadowood Estates project has a tentative map approved for 8 single family homes. This listing represents one half of the overall project. The approved tentative map has two separate cul-de-sacs, one accessible off of Tartan Trail rd, and the other off of Crystal Springs rd. These two cul-de-sacs can be purchased together or separately. Each cul-de-sac can be developed for between 1 to 4 single family homes. Great opportunity for a developer looking for a multiple home project, or an owner user looking to create an idyllic private residence / compound. The drive for this cul-de-sac would come off of Crystal Springs Rd.

ML82012016 MLS

A rare opportunity to develop a pristine piece of residential land in one of California's most sought after luxury housing markets. The Meadowood Estates project has a tentative map approved for 8 single family homes. This listing represents one half of the overall project. The approved tentative map has two separate cul-de-sacs, one accessible off of Tartan Trail rd, and the other off of Crystal Springs rd. These two cul-de-sacs can be purchased together or separately. Each cul-de-sac can be developed for between 1 to 4 single family homes. Great opportunity for a developer looking for a multiple home project, or an owner user looking to create an idyllic private residence / compound. The drive for this cul-de-sac would come off of Crystal Springs Rd.

0 Crystal Springs Rd, Hillsborough

Listed by John Hansen, 650-704-8708 from Sequoia Realty Services
(If provided) CoList: from

$4,750,000

A rare opportunity to develop a pristine piece of residential land in one of California's most sought after luxury housing markets. The Meadowood Estates project has a tentative map approved for 8 single family homes. This listing represents one half of the overall project. The approved tentative map has two separate cul-de-sacs, one accessible off of Tartan Trail rd, and the other off of Crystal Springs rd. These two cul-de-sacs can be purchased together or separately. Each cul-de-sac can be developed for between 1 to 4 single family homes. Great opportunity for a developer looking for a multiple home project, or an owner user looking to create an idyllic private residence / compound. The drive for this cul-de-sac would come off of Tartan Trail Rd.

ML81973193 MLS

A rare opportunity to develop a pristine piece of residential land in one of California's most sought after luxury housing markets. The Meadowood Estates project has a tentative map approved for 8 single family homes. This listing represents one half of the overall project. The approved tentative map has two separate cul-de-sacs, one accessible off of Tartan Trail rd, and the other off of Crystal Springs rd. These two cul-de-sacs can be purchased together or separately. Each cul-de-sac can be developed for between 1 to 4 single family homes. Great opportunity for a developer looking for a multiple home project, or an owner user looking to create an idyllic private residence / compound. The drive for this cul-de-sac would come off of Tartan Trail Rd.

0 Tartan Trail Road, Hillsborough

Listed by John Hansen, 650-704-8708 from Sequoia Realty Services
(If provided) CoList: from