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$4,498,000
4 Beds ⋅ 5 Baths ⋅ ML82051734 MLS
Prestigious Glen Ridge Masterpiece | Steps to Downtown Los Gatos Experience the pinnacle of modern luxury living in downtown's most coveted neighborhood. Balancing timeless character with modern livability, this grand 4BR/4.5BA custom estate spans 4,015 SF of light-filled space on an expansive 9,750 SF lot. Exquisite craftsmanship shines through custom doors/windows, crown molding, and rich hardwood floors. The versatile floor plan features formal living/dining rooms, an office/music room, and 2 family rooms. At the heart is a gourmet kitchen and breakfast room. A rare highlight is the private guest suit with its own full bath and kitchen perfect for multi-gen living or an au pair. Step outside to a private sanctuary: the family room opens to a luxury entertaining balcony overlooking a breathtaking, lush backyard oasis. Enjoy quiet exclusivity paired with vibrant walk-to-town convenience to world-class dining, shopping, and top-tier Los Gatos schools!

52 Hernandez AVE, Los Gatos

Listed by Mahnaz Westerberg, 408-667.2623 from The Agency
(If provided) CoList: from

$3,800,000
6 Beds ⋅ 6 Baths ⋅ ML82051259 MLS
Exceptional opportunity located at the corner of Shannon and Short Rd, this spacious 3,480 sq ft home on a 1 acre lot offers 5+ bedrooms and 5 full bathrooms in the main house plus a 1 bed/1 bath 792 Sq Ft guest house. The main level benefits from stunning views over Los Gatos and exceptional natural light. You'll find 2 full bedroom suites on this floor as well as formal living/dining with gorgeous views, large modern kitchen, breakfast nook, and office/family room. A spacious family rm (optional third bedroom) completes the upper level. A fully finished 1175 SqFt walkout basement conversion offers a potential 3 further bedrooms (currently 2 bedrooms are combined), 2 bathrooms and a recreation room. The property sits on a private 1 acre lot and includes a two-car garage, ample parking, an expansive terrace and a resort style pool, spa and beach area. Amenities include whole house on-grid solar power with battery backup. All buildings, pool, spa and terraces are located on the upper half acre leaving the lower half ready for your imagination. SB9 lot split may be possible (buyer to investigate) or simply enjoy the rural feel of your own private acre. A rural paradise with the convenience of a popular in-town neighborhood. Truly a unique opportunity.

16057 Shannon RD, Los Gatos

Listed by Slater Thomson Team, 408-205-3758 from Intero Real Estate Services
(If provided) CoList: from

$2,980,000
4 Beds ⋅ 3 Baths ⋅ ML82050572 MLS
Extensively remodeled in 2024 to 2025, this beautifully upgraded home is nestled in one of the areas most sought-after neighborhoods. Recent major improvements include a brand-new ROOF, HVAC, and water heater, along with elegant engineered hardwood flooring, updated lighting, a stunning remodeled kitchen, and a luxurious primary bathroom. The home was also fumigated in 2024 and includes a 3-year termite-free warranty for added peace of mind. A grand formal foyer welcomes you into the sophisticated living room, highlighted by a warm fireplace. The redesigned kitchen features sleek SS appliances and a peninsula that seamlessly connects to the dining area. This flexible space can also serve as a family room, with direct access to the side yard. The spacious primary suite is a true retreat, opening to a large private deck, perfect for relaxing mornings or evening unwinding. Additional upgrades include an extended driveway with new paving and redwood gate, as well as a beautifully landscaped backyard complete with mature fruit trees, including a fig tree.Located within a top-rated school district and just a short stroll to vibrant downtown Los Gatos, this home also offers convenient access to major commute routes and nearby open spaces. A rare, turnkey opportunity not to be missed.

321 Johnson AVE, Los Gatos

Listed by Serena Zhang, 510-272-7777 from Shè Homes
(If provided) CoList: from

$9,500,000
5 Beds ⋅ 8 Baths ⋅ ML82049293 MLS
Exceptional luxury estate featuring 5 bedrooms and 7.5 baths. Ideally located within walking distance of downtown Los Gatos and just off prestigious Karl Ave. Separate access via a private road and tucked at the end of a quiet cul-de-sac. This fully gated property offers exceptional privacy. While moments from town, the estate feels miles away, with remarkable tranquility, privacy, and breathtaking canyon views. Designed for modern living, the home features Lutron RadioRA lighting and automated shade systems, individually zoned heat/ac for every room, radiant floor heating, whole-house Sonos audio and central vacuum system. Enjoy breathtaking canyon views from the resort-style infinity-edge pool and spa, thoughtfully positioned on a separate level from the main yard for enhanced safety and an elevated resort ambiance. Outdoor amenities include a built-in fire pit with seating, plus a entertainment pavilion featuring a Lynx outdoor kitchen, BBQ, range, warming drawers, and more. An additional 300 sq. ft. open-concept pool house with a full bath and shower provides flexible space for guests, recreation, fitness, or entertaining and not included in the home's square footage. A rare opportunity to own a private, technology-forward retreat in one of Los Gatos most desirable locations.

15301 Robin Anne LN, Monte Sereno

Listed by George Montanari, 408-497-2213 from Compass
(If provided) CoList: from

$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

$3,488,800
4 Beds ⋅ 4 Baths ⋅ ML82048749 MLS
Brand-new modern farmhouse with attached ADU with kitchenette great for extended family. Located near Downtown Los Gatos and w/n the highly regarded Los Gatos school district. On the main level, open concept living and dining spaces. The chef's kitchen features slab quartz countertops, custom-crafted cabinetry, walk-in pantry, premium stainless-steel appliances and a large center island anchor the space. Luxury engineered hardwood flooring throughout with decorative wood-plank ceilings. Upstairs, a versatile loft provides the perfect setting for a secondary media lounge. An expansive laundry room. The light-filled primary suite is complete with a spa-inspired ensuite featuring dual vanities, designer finishes, and a generous walk-in closet. Two additional well-appointed bedrooms and a beautifully finished full bathroom with dual vanities complete the second floor. For that indoor outdoor living is an expansive covered veranda with wood-plank ceiling, slate tile. Rear yard includes paver patio, artificial turf, water-conscious landscaping, and modern landscape lighting. Additional amenities include Mitsubishi split-system heat pump, dual tankless water heaters, EV charging station, epoxy garage flooring, smart irrigation, alarm system, fire sprinklers, and built-in audio wiring.

16011 Stephenie LN, Los Gatos

Listed by Ralph & Rachel, 408-807-3073 from Compass
(If provided) CoList: from

$6,995,000
5 Beds ⋅ 7 Baths ⋅ ML82048776 MLS ⋅ Highlands of Los Gatos BLDG.
Magnificent Mediterranean Estate perched on 1.72 acre's in the Highlands Development with spectacular views of Los Gatos, Western Hill's, Mountain Winery, Cupertino Foothills, & East Bay. As you enter the wrought iron & glass doors you will find a formal entrance, formal dining room, formal living room with cast stone gas fireplace, box beam ceiling, Picture view window and french doors to exterior deck. There are 5 bedrooms with en-suite baths, 0ne 1/2 bath, including 2 large primary suites, one on each level. Spacious gourmet chef's kitchen with Thermador commercial grade appliances, 3 ovens, 6 burner gas cook-top, 2 dishwashers, wine fridge, warming drawer, and a huge center island. Attached family room with built-in cabinetry, box beam ceiling, built-in speakers, gas fireplace, and stack stone accent wall. Indoor laundry room with wash basin. Separate office with privacy glass doors. All bath surfaces are stone, granite, onyx, and travertine. Walk-in closets all with custom built-ins. Lower level Theater with screen and projector. Temperature controlled wine cellar with brick & wood beamed ceiling. Lower level game/media room with built-in speakers, 2nd butlers kitchen with rare Egyptian stone. Media rack, whole house Savant system, wood & stone floors. The list is endless!

15315 Santella CT, Los Gatos

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

$2,275,000
4 Beds ⋅ 3 Baths ⋅ ML82046670 MLS
PRICE REDUCED! Perfect home in the coveted Town of Los Gatos lifestyle! Tucked away on a quiet court, this beautifully maintained 4-bedroom single-family home backs up to historic OLD NOT ACTIVE railroad tracks, offering the ultimate premium privacy with no rear neighbors and absolutely no active train. Inside, enjoy a polished, approachable modern aesthetic with a versatile floor plan bathed in brilliant natural light. Families will love the "triple crown" of Los Gatos education: Dave's Avenue Elementary, Raymond J. Fisher Middle, and Los Gatos High School! The location is truly unbeatable. You are within easy walking distance to the Bay Club Courtside, where families can enjoy a vibrant social community, fitness, and 3 amazing pools. While this private enclave offers a peaceful retreat, you are strategically positioned just minutes from the Netflix campus, premier Silicon Valley employers, the 85 freeway, and weekend golf at La Rinconada Country Club. A rare opportunity for a premier "in-town" location!

129 Smith Ranch CT, Los Gatos

Listed by Shannon Ray, 408-677-8684 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$9,850,000
7 Beds ⋅ 8 Baths ⋅ ML82044544 MLS
This newly constructed estate is a testament to masterful craftsmanship and contemporary design. Unique architectural elements and bespoke finishes create light-filled spaces with seamless indoor-outdoor flow. Offering 5566± SF on a 1-acre+ lot, the home is tucked behind a shared private gate for ultimate seclusion. The residence features 5 en-suite bedrooms, 5.5 baths, a private office, and an attached in-law suite with a kitchen and laundry. A detached 999 SF ADU offers 2 bedrooms, 2 baths, and a 1-car garage ideal for guests or multi-generational living. A grand pivot entry reveals soaring 15 ceilings, floor-to-ceiling windows, European oak floors, imported stone, and Hi-Fi audio. A marble rotunda staircase, elevator, and spa-inspired baths with steam showers enhance the home scale. The chefs kitchen boasts Miele appliances, a steam oven, espresso station, wine fridge, and touch-latch cabinetry. Resort-style grounds include multiple balconies, fountains, an outdoor kitchen, a fire pit, & space for a pool or tennis court. High-tech amenities include Tesla solar/Powerwalls, EV charging, smart home integration, and a 3-car attached garage. Ideally located minutes from downtown Saratoga and Los Gatos, with easy access to Highways 17 & 85 and served by top-tier local schools.

18800 Saratoga Los Gatos RD, Los Gatos

Listed by Parrin Jalali, 408-497-7797 from Intero Real Estate Services
(If provided) CoList: from

$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

$2,646,000
3 Beds ⋅ 2 Baths ⋅ ML82040247 MLS
Rare Opportunity in the Beautiful and Prestigious town of Los Gatos This classic fixer-upper sits on a spacious, highly desirable lot that offers incredible potential. Perfect for contractors, visionaries, or anyone ready to build their dream home from the ground up. Tear down or renovate to create a custom residence in one of Silicon Valleys most sought-after communities, surrounded by luxury homes and excellent schools in the Los Gatos Union School District. The true value here is the generous lot size and prime location a blank canvas in an elite neighborhood where land opportunities are increasingly scarce.

16001 Stephenie LN, Los Gatos

Listed by Ralph & Rachel, 408-807-3073 from Compass
(If provided) CoList: from

$13,800,000
6 Beds ⋅ 6 Baths ⋅ ML82039880 MLS
Discover extraordinary luxury in the heart of Los Gatos. This breathtaking 20.5-acre estate offers unmatched privacy, mountain views, and a natural flowing stream crossed by your own private bridge. Inside the main residence, enjoy a gourmet chef's kitchen, elegant wet bar, private theater room, steam room, full gym, and dedicated yoga studio. Two laundry areas and a custom dog wash add everyday convenience. Step outside to a resort-style swimming pool surrounded by serene landscape. Plus, a separate two-bedroom guest house features its own laundry room, garage, and private backyard perfect for extended family or guests. Luxury, nature, and sophistication all in one extraordinary property.

130 Wood RD, Los Gatos

Listed by Rick Alva, 408-472-3999 from Windermere Valley Properties
(If provided) CoList: from

$3,988,000
4 Beds ⋅ 5 Baths ⋅ ML82036838 MLS
Classic home in Los Gatos, reimagined by renowned local architect Gary Schloh, to blend historic character with modern livability AND A RARE OPPORTUNITY TO CREATE A FAMILY COMPOUND because an adjacent lot with approved plans is also available. Buyer to verify plans with town. See FAQs and plans among disclosures. Set on approximately 12,000 sq ft, the property unfolds into a private, resort-like retreat. The rear grounds evoke an Italian villa with lush landscaping, mature trees, and multiple spaces for entertaining and relaxation. Inside, warm, sophisticated interiors offer seamless indoor-outdoor flow. The living room with fireplace anchors the home, while formal and informal spaces connect to the gardens. Flexible layout includes a separate dining room, media room/4th bedroom and a great room with patio access that could serve as a 5th bedroom, guest suite, or office. The gourmet kitchen features custom cabinetry and premium appliances and adjoining den and laundry room. The primary suite offers tree-filled views, fireplace, walk-in closet, and spa-like bath with soaking tub and shower. Additional features include wine cellar, 2-car garage, and underground utilities. Near Los Gatos Creek Trail, Vasona Lake Park, and downtown.

120 Oak Meadow DR, Los Gatos

Listed by Robin Sedgwick, 408-355-5374 from Coldwell Banker Realty
(If provided) CoList: Donald Knight from Coldwell Banker Realty
$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

$16,000,000
6 Beds ⋅ 5 Baths ⋅ ML81937235 MLS
EXCELLENT OPPORTUNITY! PRIME LOCATION! VALUE IS IN THE LAND 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...

170 Twin Oaks DR, Los Gatos

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

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