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1722 Pebble Beach CT, Milpitas
$2,798,888
4 Beds ⋅ 4 Baths ⋅ ML82063545 MLS ⋅ Summitpointe BLDG.
Welcome to this exceptional executive home in the exclusive, gated Summitpointe Country Club community, where panoramic valley views meet comfort, privacy and low-maintenance living. Approx. 2800 sf of upgraded, meticulously maintained space, this versatile home offers 3-4 bedrooms and 4 full bathrooms, plus an unfinished 533 sf basement for a future home office, gym or guest area. Three decks showcase the spectacular views and peaceful surroundings. Inside two skylights and a sun tunnel fill the home with natural light, while three fireplaces, gas featured, add warmth and ambiance. The gourmet kitchen is made for everyday living and entertaining, with a picture window, numerous upgrades, dual dishwashers and spacious pantry. The oversized primary suite is a true retreat with fireplace and stunning views, plus a luxurious bathroom with an elegant marble floor. Outside, enjoy low maintenance landscaping with artificial turf and extensive concrete walkways. The oversized driveway fits up to six cars, and the three-car garage offers exceptional parking & storage. This home combines serene surroundings, impressive views, privacy and convenience, all just minutes from the city. Come experience the views, space and effortless lifestyle this remarkable home has to offer!

1722 Pebble Beach CT, Milpitas

Listed by Debbie I. Giordano, 408-945-8988 from Master Brokers
(If provided) CoList: from

16421 Matilija DR, Los Gatos
$7,100,000
4 Beds ⋅ 5 Baths ⋅ ML82061272 MLS
With million dollar views looking out of practically every window on the North side, on this prestigious Matilija drive, it can be a little lonely on the top, but it feels extremely comfortable. Wake up to abundant morning sun allowed in through the enormous windows next to the soaring ceilings. This magnificent North facing home is surrounded by multi-million dollar homes down the road. And although this mansion is zoned for Saratoga schools, those who prefer to send their kids to Harker find it a breeze to drive there. The current owners raised their very successful children in this lucky house, and became very successful! They moved to the most prestigious neighborhood in the Bay Area. So come get the good karma! 7.03 acres of lot presents the potential to do SB9 lot splits. Buyer to investigate. $150K spent to get an ADU approved, near the entrance, pending retaining wall reviews. Enormous 1st level has primary + 2nd bedroom ensuites, and office on the first floor, giving you the expansive feel. Soaring 12' high ceiling in the living room, with 20' ceiling in the round stair case leading to 2 more ensuites on the 2nd floor! Private backyard and swimming pool. Mountains on the back & right side provide sense of protection. Solar w/ Powerwall is fully owned. Live your dream now

16421 Matilija DR, Los Gatos

Listed by Charles Liu, 650-999-3888 from Compass
(If provided) CoList: from

26883 Dezahara WAY, Los Altos Hills
$9,800,000
4 Beds ⋅ 5 Baths ⋅ ML82061986 MLS
A Private Los Altos Hills Retreat, Designed for Living - Tranquil one level acre offers exceptional privacy while remaining connected to the best of Los Altos Hills. Lush gardens, mature citrus & fruit trees, roses, and a blackberry garden create beauty throughout the seasons. The viewing deck captures Bay views and sparkling evening lights. At the heart of the property, a free-form pool with a dramatic rock waterfall. An open-air loggia with custom hot tub creates a private spa retreat, while expansive NanaWall doors open the residence to the terrace for seamless indoor-outdoor living. The pool house is a flexible space to accommodate entertaining, guests, theater, fitness or wellness. Inside, gracious formal rooms blend with inviting spaces for everyday living. Bay views enhance the living and dining rooms, while the chefs kitchen features extensive custom cabinetry, eat-in area, and seating for six. A dedicated office and separate conditioned studio offer flexibility for work, fitness, art, or creative pursuits. Substantial infrastructure includes an oversized four-car garage, exceptional storage, approximately 300-amp electrical service, EV charging with capacity for two additional chargers, and more than 70 owned solar panels.

26883 Dezahara WAY, Los Altos Hills

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

0 Swiss Creek LN, Cupertino
$549,800
ML82061088 MLS
SPECTACULAR OPPORTUNITY WITH BAY VIEWS | Seize this unprecedented opportunity to build your ultimate view estate. Steeped in privacy yet within easy reach of popular wineries and vineyards, this scenic property blends the romance of Napa Valley with the convenience and access of Silicon Valley. The immense grounds showcase breathtaking panoramas extending to San Francisco Bay and beyond. Graced with California oaks, the property is already prepped for the construction of your dream home, offering a flat building pad, on-site power, and private well access. Nestled in a custom residential enclave immersed in natural beauty, your new home will let you enjoy breathtaking views, wildlifewatching, wine-tasting, and outdoor recreation. Nearby are golf, trails, and nature preserves, and within easy reach are freeways, top tech companies like Apple, and sought-after Cupertino schools.

0 Swiss Creek LN, Cupertino

Listed by Stefan Walker, 408-209-6100 from KW Bay Area Estates
(If provided) CoList: from

10285 Magdalena RD, Los Altos Hills
$21,950,000
7 Beds ⋅ 12 Baths ⋅ ML82052707 MLS
Boasting exceptional San Francisco Bay views, this estate property offers unparalleled distinction on approximately 1.4 acres. Inspired by villas in the Mediterranean, the home is masterfully finished with an array of elaborate details from hand-painted ceilings to dazzling chandeliers and 5 fireplaces each with magnificent mantelpiece. Luxurious amenities are plentiful with an extraordinary wine cellar, professionally equipped theatre, recreation room with full bar, plus fitness center with sauna. There are 7 bedrooms, each with en suite bath, offering myriad options for family members, guests, and staff alike. From most every room, French doors open to a balcony or the grounds for a seamless connection to the outdoors and Bay views. Not to be missed are the numerous outdoor venues for entertaining highlighted by a resort-inspired pool and spa, newly added sports court, luscious green lawn, three separate outdoor kitchens, including a fabulous cabaña with sports bar, and even a zip line from the custom treehouse. Completing this rare offering is its location with easy access to all of Silicon Valley or to San Francisco plus access to excellent local schools

10285 Magdalena RD, Los Altos Hills

Listed by Gary Campi, 650-388-0730 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

3625 Sierra RD, San Jose
$3,800,000
6 Beds ⋅ 5 Baths ⋅ ML82060669 MLS
Grand hilltop estate with awe-inspiring, unobstructed sunset, city lights, and valley views spanning from San Francisco to San Jose! This enormous ~5,688 sf home rests on 2 parcels of ~1.7 acres and is embraced by undeveloped hillside almost encircling it. Only 10 minutes to hwy 680. Leave the bustle of the valley as you ascend to these breathtaking views. A sweepingly large and open kitchen/family room accommodate large gatherings while drinking in the views and sunsets through walls of glass. The formal dining room opens to the living room with soaring ceilings, fireplace, and a graceful curved staircase. The breezeway office boasts relaxing views. A generous primary suite invites in the one-of-a-kind views. Its private balcony beckons an idyllic sanctuary. 3 more upstairs bedrooms served by a large, full bathroom. The 5th bedroom and 3rd full bathroom are conveniently downstairs. On the left side of the house is a 1-bed 1-bath apartment with separate entrance for possible ADU conversion or additional living quarters. A 3-car attached garage and a 2-car garage house 5 cars. All of this grandeur and privacy conveniently close to hwy 680, restaurants, and shopping. Arguably one of the rarest, magnificent views in all of Santa Clara County sweeping from San Francisco to San Jose!

3625 Sierra RD, San Jose

Listed by Catherine Gortner, 408-258-6400 from Catherine Gortner Properties
(If provided) CoList: from

22649 Country View CT, San Jose
$1,290,000
EB41143458 MLS
Ready build flat lot, roads n build permit, exclusive estate. Approved permits/complete utilities/infrastructure/approved septic and everything present including a driveway to the flat building site(from county road) and construction storage onsite. One of a kind lot in the Calero lake estate(Almaden) 360 clear views, huge county park backyard. All permits paid and plans stamped for construction. Pictures show sample villa home at another lot built with same approved plans/design All terms flexible. PGE upgraded safety in April. Build your dream home with county approved villa design(5 bedroom/5b, 4800 sq ft), expand later adding more area/ADUs/pools/courts/winery in your backyard etc. Unlimited options. All plans/CAD files included for easy edits/modifications if needed and seller will support the building process. Even ADU plans included. Possible to subdivide in future with CA SB9 lot split for exponential growth. Developed over 40 years ago with wide road/infra/approved lot.

22649 Country View CT, San Jose

Listed by Jonathan Minerick, (888) 400-2513 from HOMECOIN.COM
(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

12780 Clayton Rd, San Jose
$4,999,000
BE41139047 MLS
Rare Opportunity: ±60 Acres in East Foothills, San Jose - Expandable to 90 Acres! This is a truly rare offering-approximately 60 acres of stunning land in the highly desirable East Foothills of San Jose, just minutes from everything Silicon Valley has to offer. An adjoining 30-acre parcel is also available, allowing buyers to combine both for a total of 90 acres at $6.9 million. An existing private well adds incredible value, making the property ideal for creating your own vineyard, orchard, or other agricultural retreat. A seasonal stream runs along the edge of the land, bordered by a neighboring apricot mini orchard-adding both charm and potential utility. Buyers are encouraged to bring their own creative vision-whether it's: Subdividing for single-family residential homes Developing multifamily units Establishing a cultural, educational, or religious center Or exploring other high-potential land uses. Buyers are strongly advised to conduct their own due diligence with the City and County of San Jose regarding zoning, re-zoning, subdivision, and permitted uses. Seller is willing to sell the property in separate parcels as outlined below: Parcel 001: 32 acres - includes a well Parcel 002: 19 acres - includes a house. Parcel 003: 24 acres Parcel 004: 15 acres-includes a spring.

12780 Clayton Rd, San Jose

Listed by Gowthaman Gurusamy, (925) 594-2990 from Realty Champion Inc
(If provided) CoList: Neema Bhatt from Realty Champion Inc

3463 Calaveras RD, Milpitas
$6,798,000
ML82040662 MLS
Spectacular 26.5-Acre Estate Site with Panoramic Views and Boundless Possibilities: Breathtaking, unobstructed 360-degree views from rolling Spring Valley hills to Silicon Valley city lights. This rare parcel is minutes from Milpitas, offering exceptional privacy with convenient access to major tech hubs, dining, and regional amenities. An on-site natural spring provides a unique water feature and potential sustainable design element. Property highlights include expansive outdoor living spaces, a large equestrian arena, and ample room for recreation, vineyards, or wellness amenities; proximity to Calaveras Reservoir, golf courses, and the Bay Areas vibrant energy, and flexible development potential to accommodate a private compound, multiple residences, guest quarters, or executive estate concepts. Investment and lifestyle benefits feature a large-format parcel in a premier Silicon Valley vicinity with long-term value and legacy opportunities, dramatic sunsets, and a natural landscape with significant architectural expression potential, all in a quiet, private setting with easy access to major transport corridors, tech employers, and regional services.

3463 Calaveras RD, Milpitas

Listed by Pete Flores, 408-568-5880 from Silicon Valley Residential Brokerage Inc
(If provided) CoList: from

3463 Calaveras RD, Milpitas
$6,798,000
3 Beds ⋅ 2 Baths ⋅ ML82037210 MLS
Spectacular 26.5-Acre Estate Site with Panoramic Views and Boundless Possibilities: Breathtaking, unobstructed 360-degree views from rolling Spring Valley hills to Silicon Valley city lights. This rare parcel is minutes from Milpitas, offering exceptional privacy with convenient access to major tech hubs, dining, and regional amenities. An on-site natural spring provides a unique water feature and potential sustainable design element. Property highlights include expansive outdoor living spaces, a large equestrian arena, and ample room for recreation, vineyards, or wellness amenities; proximity to Calaveras Reservoir, golf courses, and the Bay Areas vibrant energy, and flexible development potential to accommodate a private compound, multiple residences, guest quarters, or executive estate concepts. Investment and lifestyle benefits feature a large-format parcel in a premier Silicon Valley vicinity with long-term value and legacy opportunities, dramatic sunsets, and a natural landscape with significant architectural expression potential, all in a quiet, private setting with easy access to major transport corridors, tech employers, and regional services.

3463 Calaveras RD, Milpitas

Listed by Pete Flores, 408-568-5880 from Silicon Valley Residential Brokerage Inc
(If provided) CoList: from

25200 Loma Prieta AVE, Los Gatos
$9,800,000
4 Beds ⋅ 3 Baths ⋅ ML82039483 MLS
High above Silicon Valley, where the Santa Cruz Mountains meet the sky, lies Lago Lomita, a sanctuary of beauty, heritage, and possibility. Across forty-four acres of terraced vineyards and ridgelines, the estate is less a property than a world unto itself, suspended above the fog with cinematic views of Monterey Bay. The Adobe residence, by architect Guy Deneus, exudes quiet gravitas with bespoke woodwork, antique doors, and a chef's kitchen anchored by Sub-Zero and Thermador. Nearly every space frames the outdoors, honoring sea, sky, and vineyard alike. Sustainably farmed vines, including celebrated Nebbiolo, flourish in this rare terroir, producing vintages recognized by Wine Enthusiast. Beyond the vines, Lago Lomita is a destination: its 40-foot treehouse, featured in National Geographic, and its Lotus Belle Yurt, welcoming travelers, couples, and artists worldwide. For the discerning buyer, Lago Lomita is both a lifestyle and legacy vineyard estate, boutique brand, and stage for quiet mornings to grand celebrations. Secluded yet connected to Los Gatos, Santa Cruz, Silicon Valley, and SJC Airport, it feels a world apart while never out of reach. Lago Lomita offers more than land and vines; it offers a vantage point and a way of life few will ever know, and fewer will claim.

25200 Loma Prieta AVE, Los Gatos

Listed by Kalina Wasman, 650-773-4049 from Compass
(If provided) CoList: from

924 Croy Ridge RD, Gilroy
$800,000
ML82032091 MLS
OWN THE SUMMIT! A once-in-a-lifetime legacy offering, this 40-acre parcel has been held by the same family since the 1800s. Perched at approximately 2,400 feet at the summit of Mount Madonna, the property delivers breathtaking panoramic views of rolling valleys, mountain ranges, and the distant coastline. This pristine, off-grid sanctuary offers unmatched privacy, a tempered mountain climate, abundant wildlife, and extraordinary stargazing. Improvements include multiple level clearings, mature fruit trees, garden boxes, decking, four locked gates, a dog kennel, and an established rainwater catchment system with approximately 20,000 gallons of storage. PG&E is conveniently located next door. Ideal for agricultural use, recreation, horses, or a private retreat, this remarkable land is peacefully secluded yet approximately 30 minutes to Gilroy, Morgan Hill, and Watsonville, with scenic access to San Jose, Santa Cruz, and Monterey. A rare opportunity to have your very own mountaintop retreat.

924 Croy Ridge RD, Gilroy

Listed by Megan Kilmer, 831-888-7530 from Karma Mortgage Solutions, Inc.
(If provided) CoList: from

board logoThe data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than Bailey Properties are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.


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