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$5,750,000

Magnificent custom-built Foothill estate tucked into one of Cupertino's most sought-after enclaves, offering 5 bedrooms - including two spacious primary suites - plus 4.5 baths and two offices, ideal for modern and multi-generational living. One office enjoys its own separate side-yard access for added privacy - perfect for a home business, private study, or receiving guests. A grand double-door entry opens to an elegant marble foyer. The formal living room impresses with soaring ceilings, dramatic clerestory windows, a warm fireplace, and rich hardwood floors. The gourmet kitchen is appointed with a professional-grade gas range with six burners and a built-in griddle, a built-in Sub-Zero refrigerator, a center island with sink, abundant cabinetry, and a walk-in pantry. The adjoining family room offers a built-in entertainment center, wet bar, and sliding doors that open seamlessly to the rear yard for effortless indoor-outdoor living. The luxurious primary suite is a private retreat with serene mountain views. Outside, a sprawling backyard is filled with mature fruit and flowering trees - a tranquil setting for gatherings or quiet mornings. Zoned for top-rated Cupertino schools: Stevens Creek Elementary, Kennedy Middle, and Monta Vista High. Just minutes to premier shop

5 Beds ⋅ 5 Baths ⋅ CROC26185857 MLS

Magnificent custom-built Foothill estate tucked into one of Cupertino's most sought-after enclaves, offering 5 bedrooms - including two spacious primary suites - plus 4.5 baths and two offices, ideal for modern and multi-generational living. One office enjoys its own separate side-yard access for added privacy - perfect for a home business, private study, or receiving guests. A grand double-door entry opens to an elegant marble foyer. The formal living room impresses with soaring ceilings, dramatic clerestory windows, a warm fireplace, and rich hardwood floors. The gourmet kitchen is appointed with a professional-grade gas range with six burners and a built-in griddle, a built-in Sub-Zero refrigerator, a center island with sink, abundant cabinetry, and a walk-in pantry. The adjoining family room offers a built-in entertainment center, wet bar, and sliding doors that open seamlessly to the rear yard for effortless indoor-outdoor living. The luxurious primary suite is a private retreat with serene mountain views. Outside, a sprawling backyard is filled with mature fruit and flowering trees - a tranquil setting for gatherings or quiet mornings. Zoned for top-rated Cupertino schools: Stevens Creek Elementary, Kennedy Middle, and Monta Vista High. Just minutes to premier shop

10935 Miramonte, Cupertino

Listed by Fei Li, 949-353-9999 from Latitude 33 Real Estate
(If provided) CoList: from

$5,850,000

A truly extraordinary Vintner Estate spanning 3.6 overlooking Silicon Valley, offers sweeping panoramic San Francisco Bay Area views and an unparalleled blend of luxury and privacy, with approximately half an acre of mature estate vines including Cabernet Sauvignon, Cabernet Franc, and Merlot, creating a truly distinctive lifestyle offering. The charming 1,968 sf residence with 3 bedrooms, 2 baths features open living space, high ceilings, hardwood floors, chef's kitchen w/premium appliances and quartz counters, luxurious primary suite, versatile bonus room, and an expansive deck. Designed for grand scale entertaining, the separate 2,598 sf timber-frame event venue offers dramatic wood beam ceilings, walls of glass, indoor/outdoor fireplace, wet bar, loft, office, full bath, audio system, and stunning observatory with a premium Planewave 12.5" telescope. The 1,937 sf operational winery includes 4 fermentation tanks, bottling room, wine cellar, and climate-controlled storage. Additional highlights include owned 24kW solar generating ~35,000 kWh annually, two 2-car garages, EV charging, manicured gardens, trails, pool, hot tub, outdoor entertaining areas, and ample parking. Ideally located near wineries, hiking, and acclaimed Cupertino schools. An absolute luxury retreat.

4 Beds ⋅ 3 Baths ⋅ ML82055779 MLS

A truly extraordinary Vintner Estate spanning 3.6 overlooking Silicon Valley, offers sweeping panoramic San Francisco Bay Area views and an unparalleled blend of luxury and privacy, with approximately half an acre of mature estate vines including Cabernet Sauvignon, Cabernet Franc, and Merlot, creating a truly distinctive lifestyle offering. The charming 1,968 sf residence with 3 bedrooms, 2 baths features open living space, high ceilings, hardwood floors, chef's kitchen w/premium appliances and quartz counters, luxurious primary suite, versatile bonus room, and an expansive deck. Designed for grand scale entertaining, the separate 2,598 sf timber-frame event venue offers dramatic wood beam ceilings, walls of glass, indoor/outdoor fireplace, wet bar, loft, office, full bath, audio system, and stunning observatory with a premium Planewave 12.5" telescope. The 1,937 sf operational winery includes 4 fermentation tanks, bottling room, wine cellar, and climate-controlled storage. Additional highlights include owned 24kW solar generating ~35,000 kWh annually, two 2-car garages, EV charging, manicured gardens, trails, pool, hot tub, outdoor entertaining areas, and ample parking. Ideally located near wineries, hiking, and acclaimed Cupertino schools. An absolute luxury retreat.

15060 Montebello RD, Cupertino

Listed by Nevis and Ardizzone, 408-781-0779 from Compass
(If provided) CoList: from

$2,900,000

Perched in Cupertino's coveted Inspiration Heights, this beautifully updated home offers the perfect blend of luxury, comfort, and breathtaking hillside views. Sunlight pours through soaring ceilings, highlighting newly refinished hardwood floors, stunning contemporary lighting, and an open, inviting floor plan designed for modern living. The spectacular gourmet kitchen flows seamlessly into the spacious great room and covered deck, while the luxurious primary suite features a private balcony and a beautifully remodeled spa-inspired bath. Outside, enjoy a private backyard retreat complete with a basketball court, scenic vista point, and multiple entertaining spaces. Nestled on a quiet cul-de-sac and served by award-winning Cupertino schools, this exceptional home offers the Silicon Valley lifestyle at its finest.

4 Beds ⋅ 3 Baths ⋅ ML82054927 MLS

Perched in Cupertino's coveted Inspiration Heights, this beautifully updated home offers the perfect blend of luxury, comfort, and breathtaking hillside views. Sunlight pours through soaring ceilings, highlighting newly refinished hardwood floors, stunning contemporary lighting, and an open, inviting floor plan designed for modern living. The spectacular gourmet kitchen flows seamlessly into the spacious great room and covered deck, while the luxurious primary suite features a private balcony and a beautifully remodeled spa-inspired bath. Outside, enjoy a private backyard retreat complete with a basketball court, scenic vista point, and multiple entertaining spaces. Nestled on a quiet cul-de-sac and served by award-winning Cupertino schools, this exceptional home offers the Silicon Valley lifestyle at its finest.

23005 Standing Oak CT, Cupertino

Listed by Laura McCarthy, 650-269-1609 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$899,888

Enjoy the space & comfort of a well-designed home with the convenience of condo living in an exceptional location. Set along the CupertinoLos Altos border, this bright, move-in-ready residence offers generous living spaces, treetop & foothill views, & easy access to major employers, shopping, dining, & recreation, like Rancho San Antonio Park. The spacious living room opens to a private patio & features built-in cabinetry & a wet bar, creating an inviting setting for living & entertaining. The kitchen offers updated appliances, pantry storage, and a comfortable dining area. The generous primary suite offers abundant closet space & plantation shutters, while the second bedroom works equally well for guests, a home office, or both. New flooring, recessed lighting, fresh paint, and updated fixtures give the home a clean, refreshed feel, with the opportunity to personalize the kitchen and baths over time. Additional features include central A/C, in-unit laundry, a formal entry, and two side-by-side spaces in the secure underground garage. Woodsprings residents enjoy a pool, spa, and maintained greenbelts. Ideally situated near top-rated Cupertino schools, Apple, Google, Rancho San Antonio, shopping and dining, with easy access to Hwy 280/85, Foothill Expressway, and Caltrain.

2 Beds ⋅ 2 Baths ⋅ ML82045578 MLS ⋅ Woodsprings BLDG.

Enjoy the space & comfort of a well-designed home with the convenience of condo living in an exceptional location. Set along the CupertinoLos Altos border, this bright, move-in-ready residence offers generous living spaces, treetop & foothill views, & easy access to major employers, shopping, dining, & recreation, like Rancho San Antonio Park. The spacious living room opens to a private patio & features built-in cabinetry & a wet bar, creating an inviting setting for living & entertaining. The kitchen offers updated appliances, pantry storage, and a comfortable dining area. The generous primary suite offers abundant closet space & plantation shutters, while the second bedroom works equally well for guests, a home office, or both. New flooring, recessed lighting, fresh paint, and updated fixtures give the home a clean, refreshed feel, with the opportunity to personalize the kitchen and baths over time. Additional features include central A/C, in-unit laundry, a formal entry, and two side-by-side spaces in the secure underground garage. Woodsprings residents enjoy a pool, spa, and maintained greenbelts. Ideally situated near top-rated Cupertino schools, Apple, Google, Rancho San Antonio, shopping and dining, with easy access to Hwy 280/85, Foothill Expressway, and Caltrain.

22330 Homestead RD 226, Cupertino

Listed by Debra Schwartz Truman, 408-529-0099 from Realty One Group Infinity
(If provided) CoList: from

$1,950,000

Are you seeking the perfect piece of land to build the architectural masterpiece you have been dreaming of? Vintner's Overlook is a one of a kind legacy property at the summit of Montebello Ridge in Cupertino. This private land offers a rare above the clouds vantage point with 270 degree panoramic views of Silicon Valley and the SF Bay. This expansive 7 acre estate borders the iconic Montebello Road. Vintner's Overlook represents a unique development opportunity for a buyer seeking a private compound. The combination of breathtaking views and lush foliage throughout the property begs for floor to ceiling windows. Further enhancing the value is a private creek and the same soil as iconic local wineries. Experience total serenity just 20 minutes from Silicon Valley and 50 miles to San Francisco. Vintners Overlook embodies a rare convergence of scale, accessibility, and ridge top privacy. To find over 7 pristine acres overlooking the heart of the peninsula is a generational opportunity. This is more than a building site; it is a storied canvas offering a level of seclusion and prestige that cannot be replicated. Buyer or buyers agent to verify suitability of land for building with Santa Clara County.

ML82043457 MLS

Are you seeking the perfect piece of land to build the architectural masterpiece you have been dreaming of? Vintner's Overlook is a one of a kind legacy property at the summit of Montebello Ridge in Cupertino. This private land offers a rare above the clouds vantage point with 270 degree panoramic views of Silicon Valley and the SF Bay. This expansive 7 acre estate borders the iconic Montebello Road. Vintner's Overlook represents a unique development opportunity for a buyer seeking a private compound. The combination of breathtaking views and lush foliage throughout the property begs for floor to ceiling windows. Further enhancing the value is a private creek and the same soil as iconic local wineries. Experience total serenity just 20 minutes from Silicon Valley and 50 miles to San Francisco. Vintners Overlook embodies a rare convergence of scale, accessibility, and ridge top privacy. To find over 7 pristine acres overlooking the heart of the peninsula is a generational opportunity. This is more than a building site; it is a storied canvas offering a level of seclusion and prestige that cannot be replicated. Buyer or buyers agent to verify suitability of land for building with Santa Clara County.

0 Montebello RD, Cupertino

Listed by Andy Pickering, 415-917-3133 from California Outdoor Properties, Inc.
(If provided) CoList: from