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$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 $55,000 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

$6,698,888
5 Beds ⋅ 5 Baths ⋅ ML82056345 MLS
This Hacienda View Estate emerges as a rare legacy property of exceptional distinction, encompassing 4.4 private acres of uncompromised privacy, & timeless elegance. This meticulously designed estate commands sweeping city light and valley views that unfold in panoramic splendor, offering a serene sanctuary mere moments from the charm of downtown Los Gatos and the dynamic innovation corridor of Silicon Valley. Boasting a total enclosed area of approximately 8,731 SQFT for the main house, and including al 600 SQFT guest quarters. The estate features a spectacular glass-enclosed solarium with a retractable roof. This architectural triumph seamlessly integrates with an enormous California Room, creating an expansive year-round indoor-outdoor living experience. The chefs kitchen stands as a culinary masterpiece, elegantly appointed with premium quartz countertops, high-end finishes, and an abundance of natural light. The main residence encompasses four bedrooms, an office, and a guest quarters providing exceptional flexibility for multigenerational living. A grand motor court and striking architecture create an unforgettable sense of arrival, establishing this estate as a true family compound of rare versatility, peace, and enduring legacy! By far the best view estate in Los Gatos!

5770 Harwood PL, Los Gatos

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

$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

$11,350,000
8 Beds ⋅ 11 Baths ⋅ ML82010691 MLS
Experience the epitome of luxury living at Villa di Fiori, an award-winning architectural masterpiece nestled in the breathtaking vistas of Los Gatos, Silicon Valley. This extraordinary multi-generational smart home, recently remodeled in 2025, spans approximately 12,405 sq ft across 3.56 acres of meticulously designed private space. Featuring two exquisite dwellings, a brand new Tesla roof, and an infinity-edge PebbleTec pool with a Jacuzzi, this estate offers 8 sumptuous suites, 10.5 baths, and an array of entertainment options including an expansive theater lounge, game room, executive office, gym, wine cellar, and music room. With state-of-the-art smart home technology, 24-hour surveillance, and stunning panoramic sunset views, Villa di Fiori is not just a home; its a sanctuary of elegance and innovation, perfect for hosting grand gatherings or enjoying serene moments in your own private oasis. Experience the cascading waterfall and scent of fresh flowers, verandas & fountains accented by roses, Italian Cypress, a lush olive grove and pristine sculpture gardens. Minutes from the vibrant downtown Los Gatos, indulge in a lifestyle rich with art, culture, and culinary delights, all while surrounded by the beauty of Italian-inspired gardens and tranquil courtyards. Welcome home.

15681 Kennedy RD, Los Gatos

Listed by Ofelia Ventura, 408-218-1405 from KW Silicon City
(If provided) CoList: from

Sold listing courtesy of Greg Simpson from KWLGE
$3,800,000
4 Beds ⋅ 8 Baths ⋅ ML81988807 MLS
Sales Price reflect No buyer or buyer agent concession. Situated in the coveted Montevina neighborhood of the Los Gatos mountains is Halls Manor. This stately, gated, equestrian and vintner estate offers a unique blend of elegance w/numerous onsite amenities, presenting an unparalleled lifestyle opportunity just 6 miles from town. Set on an expansive 7.2± acre lot, the property boasts dramatic views of Lexington Reservoir, surrounding mountains and canyons, and valley floor. The vineyard, which yields approx 5-6 tons of Pinot Noir varietal, adds a touch of vintner charm to the estate. Enjoy the putting/chipping practice green, golf tee box, and horse shoe pit. Estate is designed w/ fully functioning equestrian facility, including a 4-stall barn, tack room, service kitchen, 1 & ½ baths, expansive game room/bunk house. The equestrian area is further enhanced with hot walker, palpation chutes, and paddock. Spanning 7,591± sf, the residence features 4 bedrooms, 4 full baths, 2- ½ baths, 5 fireplaces, dramatic vaulted ceilings, theater, expansive office and extensive finished attic and basement spaces. Photovoltaic solar for the main house and barn, 4 zones for heat and a/c, whole-house generator, and 2 large propane tanks.

19520 Montevina RD, Los Gatos

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

Sold listing courtesy of Klaus Feldmeier from SKFE01
$10,200,000
8 Beds ⋅ 13 Baths ⋅ ML81970865 MLS
A once in a lifetime opportunity to own a brand new contemporary masterpiece in one of the most prestigious estate neighborhoods in the Silicon Valley*No expense spared, impeccable quality, craftsmanship, technology, & modern-day luxury throughout creating a comfortable & entertaining ambience*Located on 1.2 pristine acres w/ city light views, this 10,179 SQFT masterpiece designed by Gary Kohlsaat & is built by Six Sigma Construction*Excellent contemporary floor plan w/ phenomenal architectural design featuring 8 bedrooms, 13 designer bathrooms, immense great room, fantastic bonus room/billiards room/in-law quarters, amazing office/library, & an upstairs family room*A palette of wood, stone, metal, glass, & fire is harmoniously woven together both indoors & outdoors*Enormous open epicurean kitchen w/ Thermador & Miele appliances, exquisite cabinetry & an enormous butler's pantry*Large 4-car garage w/ separate storage*Excellent indoor/outdoor living areas w/ city light views, outdoor kitchen, & resort-like pool & spa*Distinguished Saratoga Schools*Minutes to downtown Saratoga & Los Gatos* Convenient elevator & double staircase for all three levels*Sophisticated style & quality, along with artistically curated materials, blend seamlessly to create this extraordinary estate

15814 Glen Una DR, Los Gatos

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

Sold listing courtesy of Joe Piazza from CBR
$4,340,000
5 Beds ⋅ 5 Baths ⋅ BE41061433 MLS
Experience the splendor of this exquisite Los Gatos estate nestled in a prestigious Neighborhood. Revel in breathtaking panoramic views from the multiple terraced decks that surround this sophisticated home. As you enter through the secluded courtyard shaded by majestic heritage oaks, you are greeted by the grand formal foyer. The meticulously planned wings of this residence cater to a luxurious lifestyle, with towering ceilings in the spacious family room allowing natural light to flood the space. This exceptional property features a sophisticated home office, guest quarters, 5 lavish bedroom suites, sauna, and wine cellar. From the moment you step inside, you'll be captivated by the exquisite finishes and high-quality materials used throughout. The beautiful hardwood flooring adds a touch of elegance to the home. The kitchen, with its stunning island, is sure to be the heart of any gathering. Relax and unwind in the backyard oasis, complete with lush landscaping, a pool, and spa, perfect for hosting unforgettable events.

331 Santa Rosa Dr, Los Gatos

Listed by Imran (Ron) Nasir, (510) 461-0171 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Tanya Spalanzani from REEX
$10,200,000
6 Beds ⋅ 9 Baths ⋅ ML81967275 MLS
Nestled in the coveted Glen Una Ranch, this spectacular 2.75-acre estate embodies elegance and luxury in one of the most prestigious estate neighborhoods in Silicon Valley. This beautifully designed custom French Chateau estate boasts exceptional architecture with a dramatic foyer with soaring ceilings and an open floor plan design. Spanning over 10,385 sf, encompassing 6 bedrooms and 9 bathrooms [7 full /2 partial], including a luxurious primary suite featuring a fireplace and breathtaking views, open formal dining room, impressive library/office, theater room, and a lounge with a wet bar and substantial wine room. Fabulous gourmet kitchen, opening to an informal dining area and an extraordinary family great room. The outdoor amenities include a stunning infinity-edge pool, two spas, an outdoor kitchen, sprawling level lawns, and al fresco dining, all surrounded by lush manicured grounds and a serene eucalyptus grove, providing a private and peaceful setting. Six-car garage plus ample parking for guests. Located near the vibrant downtown areas of Los Gatos and Saratoga, easy access to fine and casual dining, boutique shops, parks, and hiking trails. This masterfully crafted estate presents an unrivaled opportunity to acquire a property of matchless location, size, and character.

15670 Glen Una DR, Los Gatos

Listed by David Welton, 408-234-1826 from Compass
(If provided) CoList: from

Sold listing courtesy of David Welton from COMPS
$12,521,464
7 Beds ⋅ 7 Baths ⋅ ML81966020 MLS
One of the last great estates in Los Gatos. Conveniently located to downtown Los Gatos, this expansive property's living space is just under 10,000 sq ft and offers 7 bedrooms and 6.5 bathrooms, set on a 10.6-acre lot. The estate's stunning architecture and meticulously designed grounds provide a luxurious sanctuary featuring white stucco walls, stylish arches, and intricate detailing reminiscent of European grandeur. The groundwork is in place for two additional lots, offering the potential to create a grand family compound with three homes or sell separately to develop. The 8-car garage offers ample space for car enthusiasts, while the center courtyard provides a perfect venue for large outdoor events such as weddings & parties. Recreational facilities include a sports court and a large swimming pool adorned with decorative tiles, surrounded by a sun-drenched patio ideal for relaxation and entertainment. The landscape features a mix of neatly trimmed lawns and natural wooded areas, offering both aesthetic appeal and functional opportunities. Secret gardens enhance the property's allure, with poolside lounging areas perfect for unwinding. Just 2 miles to town, yet you feel like you're on vacation. This is a genuine estate that exudes timeless elegance and inherited wealth.

239 Forrester RD, Los Gatos

Listed by Kirsten Trapani, 408-761-0686 from Christie's International Real Estate Sereno
(If provided) CoList: Barton Call from Christie's International Real Estate Sereno

Sold listing courtesy of Lilly Liang from SCXB
$5,675,000
5 Beds ⋅ 6 Baths ⋅ ML81921637 MLS ⋅ Kennedy Estates BLDG.
Fantastic Equestrian and car lovers dream hilltop Mediterranean estate in the prestigious Kennedy Estates neighborhood of Los Gatos, Ca. Situated on 4.83 lot. The main house sits atop the hillside property offering great views for the Los Gatos foothills. The property has a 1,200 square foot detached shop with an oversized garage door and a full bathroom. Two additional 2 car garages and a covered workshop space. Below the main house is a horse stable, a horse rink with plenty of pasture space below.The spacious and expansive residence has 5 bedrooms with en-suite bathrooms, 2 half bathrooms and 8,085 square feet. Home includes a wine cellar, an office/den, large living and family rooms, formal dining, a massive butler's pantry and a private deck off the primary bedroom. The gourmet kitchen has a 6 burner gas stove, duel ovens, built in refrigerator, a warming drawer, wine refrigerator within a massive kitchen island. The back yard has an infinity pool with connected spa. Lot split possible with SB9. Come and see!

233 Forrester RD, Los Gatos

Listed by Allan Mc Gurk, 408-590-1598 from eXp Realty of California Inc
(If provided) CoList: Martin Quintana from eXp Realty of California Inc

Sold listing courtesy of Martin Quintana from EXPCA

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