Refine Search
Map
Sort by
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

19465 Montevina RD, Los Gatos
$3,598,000
5 Beds ⋅ 3 Baths ⋅ ML82056050 MLS
Experience the pinnacle of gated estate living with breathtaking views stretching from Lexington Reservoir & Mt Umunhum to the lights of downtown San Jose. Just minutes from Los Gatos, this sophisticated residence combines privacy, luxury, & an exceptional setting. The refreshed interior features new flooring, fresh paint, & an open floor plan designed for effortless living & entertaining. The main level offers an office & guest suite with a full bath. At the heart of the home is the chefs kitchen with granite countertops, a gas cooktop, & abundant cabinetry, flowing seamlessly into a light-filled living area where walls of glass frame the views. Upstairs, the versatile floor plan includes two additional bedrooms & a private gym. The luxurious primary retreat is a sanctuary of comfort, featuring a spa-inspired bath & private viewing deck. Outdoor living is equally impressive, with an expansive veranda & outdoor kitchen, creating the perfect setting for entertaining. The property also features a detached barn with a workshop, loft, & abundant storage. The loft offers potential for an ADU, while the barn & usable acreage provide possibilities for equestrian use, hobbies, or additional workspace. Served by Lexington Elementary, Raymond J. Fisher Middle School, and Los Gatos High.

19465 Montevina RD, Los Gatos

Listed by Jill Cole, 408-219-3416 from Coldwell Banker Realty
(If provided) CoList: from

600 Ridge Top RD, Los Gatos
$2,295,000
3 Beds ⋅ 4 Baths ⋅ ML82060472 MLS
"Ridge Top" estate on 13 acres with breathtaking ocean, mountain & vineyard views! Tri-level Mediterranean-style home built in 1992. Spacious formal entry with vaulted ceilings. Steps up to living/dining room w/fireplace, vaulted wood ceilings, sliders to deck. Remodeled kitchen with cherry cabinets, granite countertops, stainless appliances. Pool view from kitchen window. Bright breakfast bay with floor-to-ceiling windows, spectacular 180 views. New hardwood flooring, bathrooms remodeled in '24. Two large primary suites, new custom plantation shutters. Primary bathroom features a luxurious deep, free-standing soaking tub under window, oversized shower, dual vanity. Steps down to guest suite with huge walk-in closet. Lower level family/rec room with wet bar, sitting area, spacious office bay. 3rd bedroom with fireplace, sliders to deck, adjacent hall bath. Lwr level layout designed for potential 4th bedroom. Lap pool w/spa, sunny travertine deck. Usable land offers space for vineyard, gardening, sport court or horses. Long circular driveway, generous parking, room for oversized vehicle/ RV. 4 car drive-thru garage, vaulted wood ceilings, potential to convert to ADU? Comcast internet, excellent shared well. Central location near Summit store & schools, easy drive to town or beach!

600 Ridge Top RD, Los Gatos

Listed by Rebecca Smith, 408-507-7165 from Christie's International Real Estate Sereno
(If provided) CoList: Karen Izzo from Christie's International Real Estate Sereno
15730 Shannon Heights RD, Los Gatos
$5,488,000
4 Beds ⋅ 5 Baths ⋅ ML82060376 MLS
Enjoy a beautiful contemporary Mediterranean-style estate, conveniently located just off Shannon Road, minutes from schools, parks and town. This private enclave offers remarkable privacy, sweeping surround mountain views, and a strong connection to the outdoors. Refined interiors feature travertine and engineered hardwood floors, carved limestone fireplaces, alder cabinetry & chef's kitchen with professional-grade appliances, prep sink, wine refrigerator, walk-in pantry and large island. The main level includes an executive office or 5th bedroom, en-suite guest bedroom, mudroom and attached two-car garage with Level 2 EV charging. Upstairs, the primary suite features a vaulted open-beam ceiling, fireplace, walk-in closet, private balcony, plus two additional en-suite bedrooms, a bonus room with wet bar, wine closet and laundry. Landscaped grounds include a central courtyard, covered entertaining area with fireplace and heaters, outdoor kitchen, greenhouse, garden swing and mature oaks. Smart-home technology, multi-zone HVAC, dual tankless water heaters, water softening, leak detection, and 10,000 gallons of on-site water storage complete the home. This luxurious hillside retreat brings together remarkable privacy with a balance of serenity, convenience and exceptional lifestyle.

15730 Shannon Heights RD, Los Gatos

Listed by Amy McCafferty, 408-387-3227 from Golden Gate Sotheby's International Realty
(If provided) CoList: Eric McCafferty from Golden Gate Sotheby's International Realty
16900 Sheldon RD, Los Gatos
$1,695,000
2 Beds ⋅ 2 Baths ⋅ ML82056341 MLS
Huge price reduction on this home minutes up Overlook Road & a short walk to downtown Los Gatos. Enjoy direct access to Aquinas Trailhead at the end of the road. 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

18911 Decatur RD, Los Gatos
$19,998,888
10 Beds ⋅ 8 Baths ⋅ ML82056922 MLS
Located in the heart of Silicon Valley, this extraordinary Monte Sereno estate represents a rare fusion of grand scale, refined elegance, & unparalleled convenience. Recently transformed through a $10M+ comprehensive renovation, the residence evokes the timeless grandeur of a stately European estate. Set on 1.37 pristine, flat acres, it offers approximately 17,000 square feet of impeccably curated living & storage space beneath a brand-new $1M Tesla solar roof. The main residence features ten bedrooms & eight bathrooms, complemented by a private guest house & separate apartment. Resort-caliber amenities abound, including a ten-car garage, underground shooting range, indoor basketball & racquetball court, USTA-regulation tennis court, resort-style lap pool & spa, expansive great room, home theater, private elevator, two formal libraries, and a gym/nursery. Taken down to the studs, every detail has been reimagined w/ uncompromising quality new Jeld-Wen windows & doors, all-new appliances, plumbing, & electrical systems. Secluded within a private enclave & surrounded by other prestigious estates, the property offers sweeping mountain & city light views. This is a truly iconic Silicon Valley offering! This estate is also available to lease for $45,000 a month on a year to year basis.

18911 Decatur RD, Los Gatos

Listed by Joe Piazza, 408-410-5020 from Coldwell Banker Realty
(If provided) CoList: from

13755 Skyline BLVD, Los Gatos
$4,198,000
6 Beds ⋅ 5 Baths ⋅ ML82055683 MLS
A rare combination this close to Silicon Valley: modern architecture on nearly three private acres, surrounded by protected public forest land with direct access to the Skyline Trail, assigned to Saratoga High School, and approximately 15 minutes from downtown Saratoga via Highway 9. This turn key home is ready for walking right in to enjoy a spectacular life of luxury. Private without being remote. Architectural yet warm. A home designed to experience the landscape as much as the house itself. Featured in DWELL and built in 2018, this striking contemporary home pairs dramatic scale with expansive windows, natural light and herringbone hardwood floors. The nearly 20-foot tall ceilings in the great room flows into a kitchen anchored by a dramatic oversized natural-stone island, 48-inch Wolf range and Sub-Zero refrigeration. The primary suite features approximately 14-foot ceilings, its own private patio and freestanding soaking tub. Additional bedrooms & a detached 400 +/- sq.ft. suite connected by a covered breezeway offers flexible guest, office and studio space. Outside, landscaped patios transition to mature forest and an open meadow with a three-stall barn. A rooftop deck captures distant Bay Area lights. Modern design, exceptional privacy and Saratoga just minutes away.

13755 Skyline BLVD, Los Gatos

Listed by Tiger Teerlink, 408-828-9614 from Compass
(If provided) CoList: from

15295 Kennedy RD, Los Gatos
$4,300,000
4 Beds ⋅ 4 Baths ⋅ ML82053472 MLS
This spacious 4-bedroom, 3.5-bathroom home in Los Gatos offers 2,686 sq. ft. of living space with a combination of hardwood and tile flooring throughout. The kitchen is equipped with modern amenities including a built-in dishwasher, microwave, refrigerator, garbage disposal, tile countertops, and a 220-volt outlet. Enjoy cozy evenings by the gas-burning and wood-burning fireplaces in the living areas. The home features a separate family room and a dining area, as well as an open, inverted floor plan with vaulted and open beam ceilings, skylights, and a garden window. Laundry facilities include washer/dryer hookups with both 110V and 220V electricity in the utility room. Additional amenities include built-in vacuum, wet bar, and a security gate. The property sits on a large lot of over 123,000 sq. ft. with a fenced, in-ground pool. Cooling is provided by ceiling fans, central AC, and multi-zone systems. The residence is located within the Los Gatos Union Elementary school district. Two-car garage included.

15295 Kennedy RD, Los Gatos

Listed by Lawrence Hernandez, 408-315-1200 from Realty One Group Infinity
(If provided) CoList: from

14411 Shannon RD, Los Gatos
$11,600,000
7 Beds ⋅ 8 Baths ⋅ ML82049737 MLS
Welcome to this 25.5 pristine acre Los Gatos equestrian & vineyard estate w/ magnificent hillside views*Total living square feet of this one of a kind estate is over 8,935 SQFT which includes the main house custom built in 2015, the guest house, and a bedroom suite & office in the magnificent equestrian facility*This exquisite equestrian arena and garage space is 26,135 SQFT combined and has 8 equine stalls 12x24, a one bedroom studio suite, an office, a tack room, a saddle room, hay dry storage, multiple vehicle and boat garages/storage, & 3 car garage attached to the main house*This massive solar paneled world class equestrian facility could also be converted into an indoor sports facility under lights to include tennis/pickle ball, soccer, football, and lacrosse/field hockey*This rare estate includes a large office, home gym, arts & craft room, wine cellar, pool, spa, outdoor kitchen and a guest house with a separate kitchen, living room, and bedroom suite* This Los Gatos Estate is only five minutes to Downtown. There will never again be an estate in Los Gatos with 25 acres, a 25,000 SQFT equestrian arena, 9,000 SQFT contemporary home, multiple vineyards, subdivision opportunities, views, guest house, boat/RV storage, walking/riding trails, pickle ball court, & a gated estate!

14411 Shannon RD, Los Gatos

Listed by Joe Piazza, 408-410-5020 from Coldwell Banker Realty
(If provided) CoList: from

19534 Montevina RD, Los Gatos
$4,499,999
6 Beds ⋅ 7 Baths ⋅ ML82041336 MLS
MOTIVATED SELLER. $1,500,000 PRICE IMPROVEMENT! Welcome to this newly constructed compound estate on over 10 private acres at 19534 Montevina Rd in Los Gatos. This rare hillside retreat features three separate dwellings, combining luxury living, usable land, and flexible space just minutes from downtown. The main villa offers 4 bedrooms and 3.5 bathrooms with breathtaking views of the San Jose city lights from its main living areas and outdoor spaces. Step outside to your private vineyard producing your own custom-labeled wine before arriving at an impressive Auto House built for car enthusiasts. The Auto House includes five car bays for collectors, plus an office and wet bar, creating the perfect setting for storage, display, and entertaining. Down the hill, a separate gated entry leads to a barn with 8 stalls, ideal for livestock or equestrian use. Configured as a working farm, the barn includes a laundry room and bathroom downstairs, with a fully permitted 2-bedroom, 3-bathroom living space upstairs perfect for ranch hands, rental income, guests, or returning adult children. Enjoy close proximity to the El Sereno Open Space Preserve Trail, world-renowned schools, and all the incredible restaurants and entertainment Los Gatos has to offer.

19534 Montevina RD, Los Gatos

Listed by Justin Moles, 408-896-3835 from Intero Real Estate Services
(If provided) CoList: Dominic Nicoli from Intero Real Estate Services
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

16363 Aztec Ridge DR, Los Gatos
$1,898,000
ML82042527 MLS
Beautiful view vacant parcel awaiting the design and construction of your new home. This .93 of an acre property offers an expansive flat building pad with unobstructed views of the valley floor and San Francisco Bay. Utilities are available at the street providing San Jose Water, electricity and natural gas by PG&E, and fiber optic for internet by Frontier. Septic system will need to be tested for and installed. Updated geological, soil, and geotechnical reports will need to be obtained as these parcels were entitled in approximately 1985 by the city of Los Gatos. Survey and plot map available. Award winning Los Gatos schools.

16363 Aztec Ridge DR, 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
OPEN SUN 10/25 from 1-3pm! 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. Horses are certainly possible!

24854 Skyland RD, Los Gatos

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

20245 Gist RD, Los Gatos
$550,000
ML82022340 MLS
Discover a rare opportunity to own sunny, buildable acreage just minutes from town, yet surrounded by nature. This 3.5+ acre private lot offers the perfect blend of seclusion and convenience, with a graded and rocked building pad already in place and current Building Site Approval! Observation deck with stunning panoramic views of South San Jose and surrounding mountains. Power available at the street, excellent shared well, septic design, geo/soils testing all done. Shared driveway with approved grading plan. Ready to Build - Includes custom engineered plans for a two-story home. Private trails for hiking throughout the property. Includes multiple sheds for storage and utility. Whether you're dreaming of a full-time residence or a weekend escape, this property offers the perfect canvas to build your mountain homejust 10 minutes from downtown Los Gatos. Excellent schools: Lakeside Elementary district, Los Gatos High!

20245 Gist RD, Los Gatos

Listed by Rebecca Smith, 408-507-7165 from Christie's International Real Estate Sereno
(If provided) CoList: Karen Izzo from Christie's International Real Estate Sereno
0 Twin Oaks DR, Los Gatos
$16,000,000
ML81936703 MLS
EXCELLENT OPPORTUNITY! PRIME LOCATION! This land includes the house on 170 Twin Oaks Dr! Perfect Estate property or Subdivision. One of the last large and close-in properties in Los Gatos. Located in the prestigious neighborhood of Surrey Farms, this was the original developer's home and land. The property offers sweeping valley and mountain views with gently rolling hills studded with majestic oak trees but still offers an abundance of level acreage. This special property offers an endless array of possibilities... Grand Estate, Development Opportunity, Vineyard, Equestrian...

0 Twin Oaks DR, Los Gatos

Listed by Gaylene Wyatt, 408-832-6922 from Christie's International Real Estate Sereno
(If provided) CoList: Jeff Wyatt from Wyatt & Associates

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 The Villages Realty - Rodda Realty Team 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.


Copyright 2026 MLSListings Inc. All rights reserved

How much is your home worth?

Get instant property value now!