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11837 Upland WAY, Cupertino
$7,750,000
5 Beds ⋅ 6 Baths ⋅ ML82057011 MLS
A RARE CUSTOM-BUILT HILLSIDE ESTATE. This house was built with the original owners vision in mind. Every aspect was designed around generous living spaces, quality construction, expansive terraces and architectural character for the owners own residence. It commands a rare, sweeping panorama stretching from the Palo Alto area south to the Almaden Valley. Photographs can't capture the true scale and beauty of this extraordinary setting. The breathtaking view is something that must be experienced in person. County record is 3,782 SF. The house has 4,609 SF of total conditioned space, including 2,489 SF on the main level and 2,120 SF on the upper level. The main level offers 1,662 SF of primary living space, complemented by an additional 827 SF (basement area with permit, but not counted against allowable floor area) currently configured for storage, private office, and home theater/media room. The upper level is thoughtfully designed with all 5 bedrooms and 4 full bathrooms, while 2 additional half bathrooms are conveniently located on the main level. The upper level is designed around exceptional outdoor living, with terrace access from every upper-level bedroom. The property offers a 3-car garage and an extra parking area with room for additional 5-6 additional vehicles.

11837 Upland WAY, Cupertino

Listed by Hsin-Chieh Chou, 408-518-9677 from Giant Realty Inc.
(If provided) CoList: from

10536 S Tantau AVE, Cupertino
$3,998,000
6 Beds ⋅ 5 Baths ⋅ ML82056142 MLS
Brand new custom-built Contemporary style home in the highly sought after Rancho Rinconada area in Cupertino. This New Custom-Built Contemporary Style Home offers 2,611 sq ft of living space on a 5,241 sq ft lot, including a 1,899 sq ft main home and a 712 sq ft attached ADU. This luxurious home features a great room with a modern kitchen, a family room, a dining area, and 6 bedrooms and 5 bathrooms, all boasting contemporary finishes & 10-feet ceilings in throughout the house. Chef's Kitchen features European style Cabinets, Silostone Quartz Counters and a large Island adorned with waterfalls, a full backsplash and all high-end Thermador Kitchen appliances. Spacious patios and beautifully landscaped yards offer a peaceful garden setting, perfect for outdoor activities. Fully owned 15 solar panels system produces 6.6 kwh power. Attached large sized 2 car garage with EV Charger. The attached ADU has 2 bedrooms, 2 full bathrooms and a full kitchen and living room that provides extra living space or a business office or additional rental income. Convenient Cupertino location with walking distance to the parks and easy access to Cupertino Main Street, Valley Fair & Santana Row shopping centers, Highways 85 and 280, Apple Campuses and other major Silicon Valley companies.

10536 S Tantau AVE, Cupertino

Listed by Tracy Hsu, 408-464-5030 from U16818 Financial Services
(If provided) CoList: from

15060 Montebello RD, Cupertino
$5,850,000
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

20564 Kirwin LN, Cupertino
$4,240,000
4 Beds ⋅ 3 Baths ⋅ ML82055612 MLS
A brand-new, PRE-CONSTRUCTION home in prime Cupertino location near Monta Vista High & Apple campus. With high vaulted ceilings, a striking pivot-style front door, & covered entry porch. The living room has floor-to-ceiling picture window, while the family room includes a high vaulted ceiling, wood ceiling panels, skylights, recessed lighting, black-framed windows, a custom slat-wood accent wall, a floating cabinet, & expansive glass doors. The kitchen features cabinetry, full-height backsplash, stainless steel appliances: French-door refrigerator, double oven, range, hood, & dishwasher along with a waterfall-edged island, sliding window, breakfast bar, & dining area. The primary suite offers a large picture window & walk-in closet. The primary bathroom features decorative accent tile, shower accent wall, freestanding tub, glass shower enclosure, backlit mirror, double-sink floating vanity, & water closet. Additional amenities include a dedicated office space, bedrooms with built-in closets, & Jack-and-Jill bathroom with a dual-sink floating vanity & frameless glass shower enclosure. The hallway bath offers a vanity plus tub & shower. Hallway closets, laundry area, spacious deck, & landscaped front & backyard.

20564 Kirwin LN, Cupertino

Listed by Anson Ip, 408-221-7887 from Compass
(If provided) CoList: from

22540 Stevens Creek BLVD, Cupertino
$3,194,888
4 Beds ⋅ 4 Baths ⋅ ML82048415 MLS ⋅ Alan Row BLDG.
Built in 2023 & thoughtfully enhanced by its current owners this award-winning contemporary green residence offers sophisticated modern design exceptional craftsmanship and truly turnkey living in the heart of Cupertino Featuring an open light-filled floor plan soaring ceilings luxury porcelain flooring designer finishes a dramatic LED floating fireplace.Chef-inspired kitchen with an expansive quartz island premium stainless-steel appliances Bosch dishwasher built-in oven and range custom cabinetry & generous space for everyday living and entertaining The spacious primary suite includes a walk-in closet & owner enhancements include custom automated window treatments added linen storage Additional features include a wet bar interior laundry room Nest multi-zone HVAC Owned solar Level 2 EV charging add modern efficiency and convenience The oversized two-car garage features a distinctive contemporary translucent garage door low-maintenance outdoor spaces complement the home's easy lock-and-leave lifestyle Ideally located near shopping dining parks and major Silicon Valley employers A distinctive opportunity to own a newer move-in-ready contemporary home combining modern architecture thoughtful design and low-maintenance living in one of Cupertino's most desirable school districts.

22540 Stevens Creek BLVD, Cupertino

Listed by Douglas Marshall, 408-857-9911 from Christie's International Real Estate Sereno
(If provided) CoList: from

21911 Dolores AVE, Cupertino
$5,250,000
4 Beds ⋅ 5 Baths ⋅ ML82051689 MLS
Exceptional new construction coming soon in Cupertino, situated on a rare 10,955 SF lot (per land survey) with an estimated completion in Q2 2027. Located in one of Cupertino's most sought-after neighborhoods, this modern two-story home offers approximately 3,721 SF featuring 4 bedrooms, 4.5 bathrooms, a dedicated office, and an attached 2-car garage. The open-concept design showcases modern finishes, abundant natural light, and seamless indoor-outdoor living. Upstairs features three bedrooms, including two en-suites. The primary suite offers skylights, an oversized wet area, and a spacious walk-in closet, creating a true retreat. An optional detached 749sqft 2BD/2BA ADU provides exceptional flexibility for multi-generational living, guest accommodation, or a private office. Conveniently located near Apple, major tech campuses, shopping, dining, parks, and within the Monta Vista High School district (buyer to verify). A rare opportunity to own a brand-new Cupertino estate with outstanding lifestyle and investment potential. Early buyers may have the opportunity to personalize finishes. *Images and renderings are for illustrative purposes only and subject to change.

21911 Dolores AVE, Cupertino

Listed by Axis Elite Team, 415-734-8513 from Aspire Homes
(If provided) CoList: Lisa Gao from Aspire Homes

20888 Cherryland DR, Cupertino
$4,980,000
6 Beds ⋅ 6 Baths ⋅ ML82046797 MLS
PRE SALE NOW! An exclusive new community of six single-family homes in the heart of Cupertino, starting at $4.98M. Estimated completion from Q1 2027. 20888 Cherryland features a 3,304 sq ft main house with 6 beds and 4.5 baths, plus a 563 sq ft attached ADU offering 1 bed and 1 bath. Situated on a 8,581 sq ft lot, the home blends modern American architecture with timeless charm. Enjoy an open-concept layout, soaring ceilings, and upscale designer finishes throughout. Located minutes from major tech campuses, shopping, dining, parks, and top Cupertino schools(buyer to verify). Ask about current incentives! Artistic Rendering; Images are for illustration only and do not depict the actual property.

20888 Cherryland DR, Cupertino

Listed by Axis Elite Team, 408-320-8584 from Aspire Homes
(If provided) CoList: from

10200 Empire AVE, Cupertino
$3,488,000
4 Beds ⋅ 4 Baths ⋅ ML82041938 MLS
Designed for the way Silicon Valley lives today, this exceptional custom home built in 2019 offers a rare blend of luxury, privacy and flexibility just minutes from Apple Park and major tech campuses. The thoughtfully designed three-level floor plan creates distinct living spaces ideal for executives working from home, multigenerational living, long-term guests, au pair quarters or growing families seeking separation and privacy. Filled with natural light, the open-concept great room flows seamlessly to a chef's kitchen featuring premium Viking appliances, custom cabinetry, waterfall quartz island and breakfast bar, then opens to a private deck and low-maintenance backyard. A main-level ensuite provides exceptional flexibility, while the luxurious upstairs primary retreat offers a spa-inspired bath with freestanding tub, oversized shower and walk-in closet. The private lower level features two spacious bedrooms with exterior access, full bath, bonus room ideal for office, fitness or media space, plus oversized laundry. Beautifully appointed with engineered hardwood floors, designer lighting, Nest thermostats, hot water recirculation, 240V hookup and finished garage. Outstanding Cupertino schools: Stevens Creek Elementary, Kennedy Middle and Monta Vista High

10200 Empire AVE, Cupertino

Listed by Carol Jeans, 408-313-0067 from Christie's International Real Estate Sereno
(If provided) CoList: from

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