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24766 Skyland RD, Los Gatos
$1,575,000
3 Beds ⋅ 2 Baths ⋅ ML82063639 MLS
Perched in the celebrated Skyland community of Los Gatos, 24766 Skyland Road is a rare find that captures the essence of a modern rural lifestyle on nearly three sprawling acres. At the heart of the property sits a modern 14-year-old main residence with breathtaking views that stretch across the valley to the Loma Prieta Ridge. The private outdoor oasis, where the grounds have lots of usable land features persimmons, berries, lemons, apples, pears, and plums; a true gardener's dream. The property's heritage as part of a historic ranch is reflected in its versatile structures. An oversized shop provides parking for two vehicles plus a generous amount of space for projects, or additional covered storage. Two additional structures include the original ranch house, which now serves as a functional ADU, and a separate accessory structure which was previously utilized as a living unit. Parking for many vehicles. Significant recent investment has been poured into the grounds and the secondary structures. For those looking to embrace the equestrian or outdoor lifestyle, the partial stables offer a unique head start. This is a property that offers both the quiet beauty of the mountains and the modern infrastructure and flexibility to support a busy, creative lifestyle.

24766 Skyland RD, Los Gatos

Listed by Keith Kanady, 408-316-1666 from Compass
(If provided) CoList: from

17808 Tourney RD, Los Gatos
$6,300,000
5 Beds ⋅ 6 Baths ⋅ ML82061245 MLS
Stunning Views of the Valley!! Situated on a Private Road, This Gated Modern Oasis Offers a Sweeping Panorama of the Mountains, Silicon Valley, and Bay Area Skylines. The Serene Setting Provides a True Sense of Retreat, While Just Minutes to Downtown Amenities. Exquisitely Designed For Everyday Luxury, Melding Sleek Architectural Features w/ a Soft Organic Aesthetic. Accordion Glass Nano-Doors Offer Seamless Indoor/Outdoor Transition for Entertaining w/ Fire Pit, BBQ and TV Lounge. Resort-Style Features Include Heated Saltwater Pool and Spa w/ Waterfall, In-Pool Seating, Sauna and Fully Equipped Outdoor Kitchen. Chef's Kitchen Features Thermador Appliances, Dual Ovens, Natural Stone Countertops and Accordion Window with Pass-through to Outdoor Bar. 4 En Suite Bedrooms Including a Main Floor Suite and Downstairs Guest Suite w/ Private Entrance. Luxurious Primary Suite Features Sweeping Views, Spa-Like Bathroom, Walk-In Closet and Adjoining Office (or 5th Bedroom). Lower-level Media/Game Room Adds Versatility. Wellness Features Include Radiant Heated Floors, MERV 16 Air Filtration and Whole-house Water Purification. Smart Home Control4 Automation System w/ Indoor/Outdoor Speakers, Perimeter Cameras, Gate Control and Security Alarm. Outdoor Decking Spans 2000+ SqFt. A True Sanctuary

17808 Tourney RD, Los Gatos

Listed by Tim O'Halloran, 408-930-2900 from Coldwell Banker Realty
(If provided) CoList: Cara O'Halloran from Coldwell Banker Realty

19375 Montevina RD, Los Gatos
$1,950,000
2 Beds ⋅ 1 Baths ⋅ ML82060794 MLS
~15 acres of heaven on top of the hill in Los Gatos. Surrounded by $3M to $6M estates, this beautifully remodeled home offers exceptional privacy, sweeping 270 degree views, Los Gatos schools, and expansive, usable land with endless possibilities and all just approximately 10 minutes from downtown Los Gatos and 28 minutes from Santa Cruz. The property is serviced by PG&E electricity and features a high-production private well with 20,000 gallons of fresh water storage. Approximately three fenced acres are ready for a vineyard, while an additional three acres across the road offer potential for another home, expanded vineyard acreage, or other possibilities. Inside, the main living space features soaring 15+ foot ceilings, Andersen sliding doors, Sonos audio, and a home theater system. A highly insulated, temperature-controlled wine cellar is finished with stone throughout. Two versatile sheds provide laundry facilities, additional storage, and flexible space for a variety of uses. Plans for a home expansion and infinity pool are available upon request.

19375 Montevina RD, Los Gatos

Listed by The Gummow Brothers, 408-616-9146 from Christie's International Real Estate Sereno
(If provided) CoList: Brandon Gummow from Christie's International Real Estate Sereno

16900 Sheldon RD, Los Gatos
$1,799,000
2 Beds ⋅ 2 Baths ⋅ ML82056341 MLS
Absolutely darling cottage minutes up Overlook Road and a short walk to downtown Los Gatos. Enjoy direct access to Aquinas Trailhead at the end of the road with miles of trails for walking and riding. This lovingly updated home features a remodeled kitchen with cherry cabinets, granite counters, stainless steel appliances, double oven, microwave and dishwasher. There are two renewed bathrooms with stone and tile surfaces, high ceilings, double pane windows and french door, newer retaining walls and refreshed landscaping including lemon, lime, plum, peach, and passion fruit trees. Hickory hardwood floors throughout. Two spacious bedrooms with built-in closet organizers offer beautiful and far reaching views. Recent upgrades include a new heating and air-conditioning system, new ducts, and fresh interior and exterior paint. Entertain on the large viewing deck or relax in the expansive backyard with mature landscaping & enclosed pergola and Trex decking& landscape lighting. A large two car garage with storage, plus extra parking provide convenience for guests. Served by award winning Los Gatos schools, Daves Ave Elementary, Raymond J Fisher Middle & Los Gatos High School. This charming home offers incredible sweeping views of the valley, mountain and city lights visible for miles

16900 Sheldon RD, Los Gatos

Listed by William Lister, 408-892-9300 from Coldwell Banker Realty
(If provided) CoList: from

1095 Wilderfield, Los Gatos
$1,500,000
3 Beds ⋅ 3 Baths ⋅ ML82055608 MLS
Just 20 minutes from downtown Los Gatos, this beautifully renovated mountain retreat offers the perfect balance of privacy, modern comfort, and natural beauty. Located on a paved road with easy year-round access, the property feels worlds away while remaining close to Silicon Valley. Enjoy high-speed internet, owned solar, EV charging, backup generator, and a strong-producing private well that provides abundant water year-round. An added benefit is the fire station located directly below the property, providing nearby emergency response and additional peace of mind. The thoughtfully renovated home features timeless finishes, inviting living spaces, and expansive windows that capture sweeping ocean views and fill the home with natural light. Outside, enjoy your own private sanctuary with a private hiking trail, raised garden beds, and peaceful surroundings. Relax on the deck while taking in breathtaking sunsets or entertain family and friends in complete privacy. A separate downstairs apartment offers flexibility for multigenerational living, guests, a home office, or rental income. Move-in ready and combining privacy, self-sufficiency, spectacular views, and modern amenities, 1095 Wilderfield Road offers an exceptional mountain lifestyle just minutes from downtown Los Gatos.

1095 Wilderfield, Los Gatos

Listed by David Derousseau, 831-246-6564 from Epique Realty
(If provided) CoList: from

950 Oak Ridge RD, Los Gatos
$2,388,000
3 Beds ⋅ 3 Baths ⋅ ML82054818 MLS
A Rare Los Gatos Mountain Estate with 21.59 Acres, Privacy, Views & ADU Discover an extraordinary private ridge-top sanctuary just minutes from downtown Los Gatos and Silicon Valley. Set on 21.59 sun-drenched acres, this gated estate offers exceptional privacy, sweeping valley and mountain views, and an unmatched sense of space and serenity. The 3,083 sq ft main residence features vaulted ceilings, expansive windows, abundant natural light, and seamless indoor-outdoor living. The recently remodeled gourmet kitchen is designed for both everyday living and entertaining. A spacious dedicated office provides an ideal work-from-home setting, while expansive view decks create spectacular spaces for entertaining and enjoying unforgettable sunsets. A detached 484 sq ft ADU offers flexible space for guests, home office, or potential rental use. The expansive acreage includes private trails, producing orchard and garden areas, multiple outdoor living spaces, and room to create your own mountain lifestyle. Owned solar, backup power, and a private well add valuable self-sufficiency. Located in the Los Gatos High School service area, this rare property combines desirable schools with exceptional privacy, panoramic views, usable acreage, an ADU, and convenient Silicon Valley access.

950 Oak Ridge RD, Los Gatos

Listed by Nian Gong, 949-877-9768 from Goodview Financial & Real Estate
(If provided) CoList: from

27255 Loma Prieta WAY, Los Gatos
$1,399,000
4 Beds ⋅ 3 Baths ⋅ ML82053342 MLS
Perched in the scenic Los Gatos Mountains, this beautifully maintained 4-bedroom, 3-bathroom home offers breathtaking panoramic views, spacious living, and exceptional flexibility for today's lifestyle. Thoughtfully designed, the home features hardwood floors, generously sized bedrooms, and an inviting floor plan that blends comfort with functionality. The expansive upstairs bonus area provides incredible versatility, making it ideal as a guest bedroom, home office, media room, playroom, fitness space, or multi-purpose retreat to fit your changing needs. Large windows frame the stunning mountain vistas, creating a peaceful backdrop throughout the home while filling the living spaces with natural light. Pride of ownership is evident inside and out, with meticulous maintenance allowing the next owner to move right in and enjoy. Whether you're searching for a Los Gatos mountain home, a property with gorgeous views, flexible living space, or room to work from home while enjoying a tranquil setting, this home delivers the perfect balance of privacy and space.

27255 Loma Prieta WAY, Los Gatos

Listed by Monica Lussier, 408-472-2414 from Compass
(If provided) CoList: Michele Replogle from Compass

0 Soda Springs RD, Los Gatos
$1,800,000
ML82052900 MLS
Rare opportunity to own approximately 18 acres in the picturesque Los Gatos Mountains along Soda Springs Road. Comprised of 4 contiguous parcels, this exceptional property is located just 30 minutes from Downtown Los Gatos. A private road winds through the property, providing access to multiple potential building sites positioned to capture sweeping views of Monterey Bay, Vasona Reservoir, Silicon Valley, and on clear days, the San Francisco Peninsula. Held by the same family for generations, this legacy property offers significant possibilities - a private estate, multi-generational family compound, vineyard, equestrian retreat, hobby farm, or luxury mountain getaway. Enjoy the privacy and tranquility of your own mountain landscape while remaining within easy reach of Silicon Valley. Seller will finance subject to acceptable terms and conditions. Buyers should verify zoning, development potential, utilities, water rights, access, and all land use possibilities.

0 Soda Springs RD, Los Gatos

Listed by Geoff Hollands, 408-761-7307 from Coldwell Banker Realty
(If provided) CoList: Michael Majchrowicz from Coldwell Banker Realty

19751 Hicks RD, Los Gatos
$5,500,000
3 Beds ⋅ 2 Baths ⋅ ML82047686 MLS
A rare, fully improved private estate compound opportunity in Los Gatos. Set across 8.23 secluded acres just 20 minutes from downtown, this extraordinary property offers immediate luxury living today and a dramatically accelerated path to a future world-class custom estate! Accessed through two secure electric gates and a long stone-paver drive, the property includes an architecturally designed luxury guest residence with sophisticated smart-home integration, floor-to-ceiling glass, automatic shades, wide-plank engineered hardwoods, quartz finishes, steam shower, expansive view deck, spa, dual EV charging, and high-speed Starlink connectivity. What makes this offering exceptionally rare is the immense infrastructure and time-compression value already in place: premium flat buildable estate area, completed site work, permitted septic infrastructure, domestic well, substantial water storage, advanced solar and intelligent battery microgrid, and the ability to bypass years of planning, excavation, and development complexity. A true private sanctuary with top Los Gatos schools, exceptional proximity to Silicon Valley, and extraordinary optionality for the visionary buyer seeking a legacy estate, luxury retreat, or multi-generational compound.

19751 Hicks RD, Los Gatos

Listed by Amy McCafferty, 408-387-3227 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

16840 Cypress WAY, Los Gatos
$8,498,000
5 Beds ⋅ 6 Baths ⋅ ML82036889 MLS
Welcome to an exquisite Mediterranean estate nestled in the foothills of Los Gatos at 16840 Cypress Way. Located at the bottom of Cypress Way, this gated property offers privacy and dramatic views with easy access to the vibrant downtown. This luxurious residence boasts breathtaking vistas of the valley, offering a stunning 5,844sf± of refined living space. Designed for both elegance and comfort, the home features 5 sumptuous bedrooms, each with private ensuite bath, including a convenient main level suite for multi-generational living. The expansive main level is thoughtfully arranged, encompassing a formal living room, spacious office, kitchen/great room, and a formal dining room that opens onto a voluminous covered patio. Perfect for entertainment, this outdoor space overlooks the verdant gardens and enchanting water features. The property spans over 2.03± acres. This gated sanctuary is complemented by a 800sf± estate entertainment retreat, jacuzzi pavilion, and sunning terrace, inviting you to indulge in the serene surroundings. Enter through a custom gated entry onto an expansive car park, accented by a central fountain. Award winning Los Gatos Schools! Seller to provide $200,000 credit to buyer for any cosmetic modifications. Furnishings to be included in the sale.

16840 Cypress WAY, Los Gatos

Listed by Nevis and Ardizzone, 408-891-8149 from Compass
(If provided) CoList: from

22065 Old Santa Cruz HWY, Los Gatos
$360,000
ML82038705 MLS
Imagine your dream home nestled amongst the majestic redwoods of the Santa Cruz Mountains. This remarkable parcel offers the rare advantage of a mostly flat building envelope, a blank canvas ready for your architectural vision. Privacy, peace, and unparalleled natural beauty surround you. From this elevated vantage point, enjoy breathtaking views glittering city lights stretching across the valley and the tranquil expanse of Lexington Reservoir shimmering under the California sun. Beyond the views, discover a profound connection to nature. Towering trees, the calming sounds of the forest, and an abundance of local wildlife create an idyllic retreat from the everyday. This is more than a property; it's a lifestyle. Significant investments have been made in its development. Numerous investigations and meticulously prepared reports lay the groundwork for your build; septic perc test, a detailed geological report, architectural renderings for conceptual purposes, and precise build pad drawings, PGE substructure designs and a shared well agreement, simplifying your path to development. Ready for its new owner to make the final push for build site approval and break ground. EZ commute. Nearby historic town of Patchen, rich local history. Loma Prieta Elem. Los Gatos High School.

22065 Old Santa Cruz HWY, Los Gatos

Listed by Ed Dee, 408-896-1117 from Sanctuary Real Estate
(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

24854 Skyland RD, Los Gatos
$1,895,000
3 Beds ⋅ 2 Baths ⋅ ML82037619 MLS
Ocean Views clear to Monterey from this quiet location nestled in nature! Stunning views every day! Served by top schools & just minutes from downtown Los Gatos and Santa Cruz beaches. This home boasts 1,900 square feet with gleaming hardwood floors; an updated kitchen with quartz counters, breakfast area and bar seating at the center island plus a beautiful view! 3 bedrooms + an office (with a lot); a family room & sunny dining room. You'll love working from home! 2 car garage with storage AND a huge 24 x 48 detached garage/workshop with full bathroom, air compressor, oversized door & pull-through capabilities. The awesome property is 5.69 acres w/over 3 acres fully fenced w/gated entry. Versatility in the land! A small private wine/table grape vineyard + orchard with several varieties of fruit trees including: apple, pear, peach, fig, persimmon, lemon plum, orange & pomegranate. Separate garden space. 10,000 gallons of water storage; an adorable tree house; ample outdoor space for entertaining & plenty of parking! Located in an award winning school district and an easy commute to Santa Cruz or the Silicon Valley this property has it all. Expand the vineyard or enjoy your private harvest! So many possibilities here!

24854 Skyland RD, Los Gatos

Listed by Bobbie J. Herteman, 831-566-5835 from Bobbie Herteman Real Estate
(If provided) CoList: from

22125 Miller Ridge RD, Los Gatos
$1,650,000
4 Beds ⋅ 3 Baths ⋅ ML82037375 MLS ⋅ Las Cumbres BLDG.
Perched atop a sunny ridge, this home offers stunning views of the Santa Cruz Mountains in the tranquil Las Cumbres community, where natural serenity meets modern luxury. Recently remodeled, the interior features hardwood floors, granite countertops, recessed lighting, a home gym, and Nest and Ring smart home systems. Panoramic windows frame mountain vistas, while multiple decks invite relaxation. Outside, the home boasts just as much as within; enjoy the playground with a sandbox and room to run, a hot tub, and a gas fire pit under the stars. Wine enthusiasts will love the custom wine cellar, adding sophistication to this retreat. A large solar system, two electric car chargers, and a Generac backup generator provide sustainable energy and peace of mind. With high-speed internet, a home office with inspiring views becomes a reality. Practical touches include a two-car garage with a workshop, a fenced dog run, a spacious lower driveway, and ample upper parking. Top-rated schools include Lakeside Elementary, CT English Middle, and Los Gatos High. This is a serene mountain sanctuary.

22125 Miller Ridge RD, Los Gatos

Listed by Thomas Mendoza, 831-435-8518 from Compass
(If provided) CoList: from

0000 Wagner RD, Los Gatos
$1,650,000
ML82023960 MLS
Build Your Dream Home on 23 Acres in Los Gatos. Discover a truly unique opportunity to build on a 23-acre parcel surrounded by multi-million-dollar estates. It is conveniently located with easy freeway access to highway 85 and a short 10-minute drive to downtown Los Gatos while avoiding highway 17. This tranquil, south-facing property offers panoramic views, a burbling creek, and the perfect canvas for your custom home. Enjoy the best of both worlds: a serene, rural setting with modern conveniences just a short drive away. With easy access to Downtown Los Gatos and Blossom Hill Road, you'll find top-tier dining, shopping, amenities in two directions and award-winning Los Gatos schools. Outdoor enthusiasts will love the direct access to over 1,000 acres of adjacent Mid-Peninsula Regional Open Space, with private trails for hiking and horseback riding. The land's sunny exposure provides a perfect setting to plant your own vineyard. Home plans for 5,251 sf plus 401 sf garage, civil engineering and geological reports available to help you begin the process.

0000 Wagner RD, Los Gatos

Listed by Paul Burrowes, 408-497-3989 from David Lyng Real Estate
(If provided) CoList: from

14721 Shannon RD, Los Gatos
$1,150,000
ML82018990 MLS
Welcome to your future Tuscan-inspired estate, nestled in the scenic foothills of Los Gatos where rolling vineyards, oak-studded hillsides, and sweeping vistas create the perfect backdrop for luxury living. Just minutes from downtown Los Gatos, award winning schools, boutique shopping, fine dining, hiking trails, wineries and freeway access, this property offers both tranquility and convenience. Set on 1.19 acres, the proposed 4,310 sqft residence features a detached 2 car garage with workspace plus an attached 1 car garage. The homesite is ideally positioned to capture panoramic views while providing privacy and serenity. Much of the preparation work has already been completed: architectural plans, civil plans, soil engineering report, and topographic survey, with water and electricity nearby. This significantly shortens the development timeline, creating a rare opportunity for buyers looking to custom build their dream home or investors seeking a premier project in one of Silicon Valleys most desirable communities. Buyer to verify all disclosures, reports and information provided to their satisfaction.

14721 Shannon RD, Los Gatos

Listed by Nikil Balakrishnan, 408-813-8001 from Realty World Premier Properties
(If provided) CoList: Mohini Balakrishnan from Realty World Premier Properties

16497 S Kennedy RD, Los Gatos
$1,698,000
5 Beds ⋅ 6 Baths ⋅ ML82008703 MLS
Spectacular 2.58± acre building site in the prestigious South Kennedy Road neighborhood of Los Gatos. Planning approval has been received from the town of Los Gatos for a 4,810sf±, 5 bedroom, 4 full and 2 half bathroom home. This beautiful property offers open vistas of the surrounding Los Gatos mountains and stately oak trees with a clear and easily accessible building site. The location sits amongst beautiful estate quality homes with convenient access to the charming downtown, local schools, shopping, and freeways. There are two possible entry points onto the property which offers elegant access to your newly built home. City utilities are available at or very near the building site for efficient site development. Geotechnical and soils, survey, and topographical reports available. This site sits within the Los Gatos School District.

16497 S Kennedy RD, Los Gatos

Listed by Nevis and Ardizzone, (408) 891-8149 from Compass
(If provided) CoList: from

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