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Nestled in the hills above downtown San Carlos, this striking contemporary residence designed by Fred Herring offers a masterclass in architectural character. The home immediately impresses with its signature curved vaulted ceilings and a dramatic wall of windows that frame sweeping canyon and neighborhood views. Thoughtfully designed for both entertaining and privacy, the layout features seamless living spaces on the entry level that flow naturally toward the scenery. Two bedrooms are tucked away on their own level, providing a serene retreat with peaceful views of the surrounding trees and landscape. A third bedroom and full hall bathroom are situated on a separate split level, offering a flexible and spacious floor plan. The primary suite occupies its own expansive wing, serving as a true sanctuary. Double doors open onto a private deck, while the luxurious en suite bathroom features a generous soaking tub and a separate shower. This residence offers a premier address with effortless access to tech hubs such as Meta and Google. Situated moments from the greenery of Highland Park, it blends urban convenience with the prestige of a highly sought-after school district. A standout choice in The City of Good Living.

4 Beds ⋅ 3 Baths ⋅ ML82061751 MLS

Nestled in the hills above downtown San Carlos, this striking contemporary residence designed by Fred Herring offers a masterclass in architectural character. The home immediately impresses with its signature curved vaulted ceilings and a dramatic wall of windows that frame sweeping canyon and neighborhood views. Thoughtfully designed for both entertaining and privacy, the layout features seamless living spaces on the entry level that flow naturally toward the scenery. Two bedrooms are tucked away on their own level, providing a serene retreat with peaceful views of the surrounding trees and landscape. A third bedroom and full hall bathroom are situated on a separate split level, offering a flexible and spacious floor plan. The primary suite occupies its own expansive wing, serving as a true sanctuary. Double doors open onto a private deck, while the luxurious en suite bathroom features a generous soaking tub and a separate shower. This residence offers a premier address with effortless access to tech hubs such as Meta and Google. Situated moments from the greenery of Highland Park, it blends urban convenience with the prestige of a highly sought-after school district. A standout choice in The City of Good Living.

215 Winding WAY, San Carlos

Listed by Soraya Orumchian, 650-888-1794 from Compass
(If provided) CoList: from

$3,998,000

Situated on a highly-sought after street in desirable San Carlos, this refined 2016 home seamlessly blends classic elegance with turnkey modern functionality. Inside, high ceilings, wide-plank hardwood floors, and custom cabinetry create a warm, polished backdrop flooded with natural light. The main level is designed for effortless living with a welcoming living room overlooking an inviting front porch. The layout flows naturally into an open-concept family room and chef's kitchen complete with marble countertops, a central island, and premium Bosch, Sub-Zero, and Wolf appliances opening directly onto a covered patio for fluid indoor-outdoor entertainment space. A main-floor bedroom and full bath offer ideal flexible space for guests or multi-generational living. A dedicated laundry room and attached two-car finished garage with ample storage space offers extra functionality. Upstairs, the primary suite is complete with two walk-in closets, a granite bath with a soaking tub, dual vanity, and marble shower. Outside, the low-maintenance grounds are framed by mature oak trees. Close to Arguello Park and located just a mile from the vibrant Laurel Street, this home offers easy access to Highways 101, 280, and top-rated local schools including Carlmont High School.

4 Beds ⋅ 3 Baths ⋅ ML82063566 MLS

Situated on a highly-sought after street in desirable San Carlos, this refined 2016 home seamlessly blends classic elegance with turnkey modern functionality. Inside, high ceilings, wide-plank hardwood floors, and custom cabinetry create a warm, polished backdrop flooded with natural light. The main level is designed for effortless living with a welcoming living room overlooking an inviting front porch. The layout flows naturally into an open-concept family room and chef's kitchen complete with marble countertops, a central island, and premium Bosch, Sub-Zero, and Wolf appliances opening directly onto a covered patio for fluid indoor-outdoor entertainment space. A main-floor bedroom and full bath offer ideal flexible space for guests or multi-generational living. A dedicated laundry room and attached two-car finished garage with ample storage space offers extra functionality. Upstairs, the primary suite is complete with two walk-in closets, a granite bath with a soaking tub, dual vanity, and marble shower. Outside, the low-maintenance grounds are framed by mature oak trees. Close to Arguello Park and located just a mile from the vibrant Laurel Street, this home offers easy access to Highways 101, 280, and top-rated local schools including Carlmont High School.

2209 Carmelita DR, San Carlos

Listed by The Dreyfus Group, 650-485-3476 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$1,298,888

Discover the natural beauty of hillside living at 237 Winding Way in San Carlos. This one-bedroom, one-bath home offers a wonderful opportunity for a first-time buyer, with stunning views that make the setting truly special. Enjoy the peaceful feel of a hillside retreat while staying close to shopping centers and everyday conveniences. For those with a bigger vision, the property also presents an opportunity to explore an addition or a new home, subject to applicable requirements and approvals. Whether you're looking for a place to call your own or imagining its future potential, this property offers a beautiful setting and room to dream. All Section one items in the termite report have been cleared.

1 Beds ⋅ 1 Baths ⋅ ML82062925 MLS

Discover the natural beauty of hillside living at 237 Winding Way in San Carlos. This one-bedroom, one-bath home offers a wonderful opportunity for a first-time buyer, with stunning views that make the setting truly special. Enjoy the peaceful feel of a hillside retreat while staying close to shopping centers and everyday conveniences. For those with a bigger vision, the property also presents an opportunity to explore an addition or a new home, subject to applicable requirements and approvals. Whether you're looking for a place to call your own or imagining its future potential, this property offers a beautiful setting and room to dream. All Section one items in the termite report have been cleared.

237 Winding WAY, San Carlos

Listed by Shawn Jahan, 408-916-8665 from Realty World Dominion
(If provided) CoList: from

$3,750,000

The ultimate blend of one-level living and one of the greatest views on the Peninsula has just hit the market! Custom-built for the current family, this home was not just lived in... it was loved for nearly 50 years! Featuring 4 spacious bedrooms and 2 1/2 baths, along with a formal dining room, formal living room, and one of the largest kitchens you'll find, this home is perfectly appointed for a world-class chef. Top-quality materials and craftsmanship, combined with a tremendous amount of counter space, make this the perfect setting for every holiday, celebration, and gathering! Let's not forget the family room with soaring ceilings, stunning views, and a fireplace! Gleaming hardwood floors and fresh paint inside and out add to the appeal, while the home and garage are conveniently situated on the same level for easy everyday living. And now for the hidden gem a fully separate 1-bedroom, 1-bath ADU with its own private balcony and stunning views! Whether for extended family, guests, a home office, or additional flexibility, the possibilities are endless. With a separate laundry room, tremendous storage, exceptional privacy, and great San Carlos schools, you may never want to leave! Make this one-of-a-kind dream home a priority to see. $3,750,000 is a transparent price.

5 Beds ⋅ 4 Baths ⋅ ML82061647 MLS

The ultimate blend of one-level living and one of the greatest views on the Peninsula has just hit the market! Custom-built for the current family, this home was not just lived in... it was loved for nearly 50 years! Featuring 4 spacious bedrooms and 2 1/2 baths, along with a formal dining room, formal living room, and one of the largest kitchens you'll find, this home is perfectly appointed for a world-class chef. Top-quality materials and craftsmanship, combined with a tremendous amount of counter space, make this the perfect setting for every holiday, celebration, and gathering! Let's not forget the family room with soaring ceilings, stunning views, and a fireplace! Gleaming hardwood floors and fresh paint inside and out add to the appeal, while the home and garage are conveniently situated on the same level for easy everyday living. And now for the hidden gem a fully separate 1-bedroom, 1-bath ADU with its own private balcony and stunning views! Whether for extended family, guests, a home office, or additional flexibility, the possibilities are endless. With a separate laundry room, tremendous storage, exceptional privacy, and great San Carlos schools, you may never want to leave! Make this one-of-a-kind dream home a priority to see. $3,750,000 is a transparent price.

3291 Melendy DR, San Carlos

Listed by Alex Lehr, 650-766-5300 from Guide Real Estate
(If provided) CoList: from

$2,998,000

From the moment you enter, the views take center stage. Expansive picture windows frame striking mountain and open-space vistas throughout this spacious five-bedroom San Carlos home. Four separate decks extend the living spaces outdoors, offering inviting places to relax, entertain, and enjoy the scenery. With almost 3,400 square feet across two levels, the home offers a thoughtful balance of gathering spaces and private retreats. The main level features the primary suite, two additional large bedrooms, a spacious eat-in kitchen with hillside views, separate living and family rooms, and a formal dining room for the nights that call for it. Downstairs, two more bedrooms, a full bath, and a third family room offer flexibility for guests, extended family, or whatever your needs may be. Refinished hardwood floors, fresh paint throughout, upgraded lighting, and newly rebuilt Trex decks add to the home's move-in-ready appeal. Multiple furnaces and A/C provide year-round comfort. Mature lemon, loquat, and cherry trees add a delicious touch to the property. Top-rated schools, shopping, dining, and parks are all within walking distance, with easy access to downtown San Carlos, Belmont, Highways 280 and 101, and Caltrain.

5 Beds ⋅ 3 Baths ⋅ ML82056276 MLS

From the moment you enter, the views take center stage. Expansive picture windows frame striking mountain and open-space vistas throughout this spacious five-bedroom San Carlos home. Four separate decks extend the living spaces outdoors, offering inviting places to relax, entertain, and enjoy the scenery. With almost 3,400 square feet across two levels, the home offers a thoughtful balance of gathering spaces and private retreats. The main level features the primary suite, two additional large bedrooms, a spacious eat-in kitchen with hillside views, separate living and family rooms, and a formal dining room for the nights that call for it. Downstairs, two more bedrooms, a full bath, and a third family room offer flexibility for guests, extended family, or whatever your needs may be. Refinished hardwood floors, fresh paint throughout, upgraded lighting, and newly rebuilt Trex decks add to the home's move-in-ready appeal. Multiple furnaces and A/C provide year-round comfort. Mature lemon, loquat, and cherry trees add a delicious touch to the property. Top-rated schools, shopping, dining, and parks are all within walking distance, with easy access to downtown San Carlos, Belmont, Highways 280 and 101, and Caltrain.

66 Club DR, San Carlos

Listed by Robert Purnell, 415-272-1498 from Compass
(If provided) CoList: from

$5,988,000

Majestically situated on a lush .47-acre lot at the end of a quiet, scenic cul-de-sac, this exquisite custom-built home commands attention with its Mediterranean-inspired design, impeccably manicured grounds, and breathtaking panoramic Bay views. Spanning over 6,500 square feet, the home boasts five bedrooms and five full bathrooms, offering a perfect balance of grandeur and warmth. The thoughtfully designed three-level floor plan features soaring ceilings, elegant marble finishes, and expansive windows that showcase stunning views from every room. Regal fireplaces and gleaming hardwood floors enhance the sophisticated yet inviting ambiance throughout the home. Outside, the grounds are a masterpiece of vibrant landscaping adorned with fragrant wisteria, heritage oaks, and romantic pathways. Sweeping view-facing decks, a level lawn area and an enchanting arbor create an idyllic outdoor retreat, perfect for relaxation or entertaining. Located just minutes from the dynamic energy of Silicon Valley, this rare and extraordinary home provides a peaceful sanctuary to unwind and recharge after a busy day. Welcome home!!!

5 Beds ⋅ 5 Baths ⋅ ML82031347 MLS

Majestically situated on a lush .47-acre lot at the end of a quiet, scenic cul-de-sac, this exquisite custom-built home commands attention with its Mediterranean-inspired design, impeccably manicured grounds, and breathtaking panoramic Bay views. Spanning over 6,500 square feet, the home boasts five bedrooms and five full bathrooms, offering a perfect balance of grandeur and warmth. The thoughtfully designed three-level floor plan features soaring ceilings, elegant marble finishes, and expansive windows that showcase stunning views from every room. Regal fireplaces and gleaming hardwood floors enhance the sophisticated yet inviting ambiance throughout the home. Outside, the grounds are a masterpiece of vibrant landscaping adorned with fragrant wisteria, heritage oaks, and romantic pathways. Sweeping view-facing decks, a level lawn area and an enchanting arbor create an idyllic outdoor retreat, perfect for relaxation or entertaining. Located just minutes from the dynamic energy of Silicon Valley, this rare and extraordinary home provides a peaceful sanctuary to unwind and recharge after a busy day. Welcome home!!!

222 Oakley AVE, San Carlos

Listed by Vicky Yu, 650-701-5058 from Coldwell Banker Realty
(If provided) CoList: from

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