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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

$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

$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

$3,300,000
4 Beds ⋅ 4 Baths ⋅ ML82042958 MLS
Excellent Opportunity to Own a Gorgeous Flat Piece of Property w/Two Beautiful Light & Bright Houses on a HUGE 11,040 Sq Ft Lot in Highly Desirable Los Gatos w/Award Winning Daves Avenue, Fisher Middle & Los Gatos High! In the Main House, Explore the Many Features Including a Spacious Floor Plan Showcasing (4) Bedrooms, (2.5) Bathrooms, 2,221 +/- Sq Ft of Living Space PLUS 447 +/- Sq Ft Finished Basement, Inviting Living Room w/Cozy Wood Burning Fireplace, Oversized Family Room, Sun-Lit Kitchen w/New Gas Cooktop, Hood & Double Oven, White Cabinetry & Peninsula, Luxury VP Flooring, Re-imagined Bathrooms, Recessed Lighting, Skylights, Sun Tunnel, Raised Panel Doors, New Modern Light Fixtures & Door Handles, Modern Interior & Exterior Paint. The Second Home Offers an Open Floor Plan w/Full Kitchen & Kitchen Nook w/Abundance of Cabinetry, Open Bedroom w/Flex Space, Bathroom, Living Room, Dining Area, Recessed Lighting & Carpeting Boasting 628 +/-Sq Ft of Living Space. Enjoy the Captivating Front & Back Yard Boasting Newly Planted Drought Tolerant Shrubs, Rose Bushes, Newly Installed Fresh Sod, Mature Trees, & Large Deck for Indoor/Outdoor Entertaining. Potential for Expansion w/Premier Location. Minutes to Shopping, Restaurants, Vasona Park, Trails & Downtown Los Gatos.

17391 E Vineland AVE, Los Gatos

Listed by Lisa Thompson, 408-373-6656 from Intero Real Estate Services
(If provided) CoList: Bill Thompson from Intero Real Estate Services

Sold listing courtesy of Daniel Harbuck from HC44P
$7,800,000
5 Beds ⋅ 5 Baths ⋅ ML82044168 MLS
A beautifully executed, move-in ready luxury residence in the highly sought-after Surrey Farms neighborhood, this custom home by architect Gary Kohlsaat blends refined design, resort-style amenities, & a premier Los Gatos setting on a thoughtfully designed half-acre. Expansive living spaces flow into an open-concept kitchen & family room, where side-by-side La Cantina doors open to the resort-style grounds. The gourmet chefs kitchen is designed for both everyday living & entertaining, featuring premium appliances, an oversized waterfall island, designer finishes, & seamless connection to the main gathering spaces. The backyard is a true retreat with pool, spa, fire pit, turf lawn, play areas, built-in trampoline, sauna, outdoor shower, & covered loggia with fireplace, skylight, TV & outdoor kitchen with Evo grill. The primary suite offers a private deck, spa-like bath, & dual walk-in closets, while a detached ~800 sq ft pool house/ADU includes a living area, optional bedroom/dance-yoga studio & full bath for flexible living or guests. Additional features: game room, dedicated office, ground-level en-suite bedroom, smart home features, mudroom, & ~973 sq ft three-car garage with epoxy floors, home gym, & built-in storage. A truly special home with coveted Los Gatos schools.

140 Twin Oaks DR, Los Gatos

Listed by Fran Papapietro, 408-623-4155 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Lisa Radding from CBR
$4,998,000
6 Beds ⋅ 7 Baths ⋅ ML82041336 MLS
$1,000,000 PRICE IMPROVEMENT! BEST VALUE IN LOS GATOS Welcome to this newly constructed compound estate on over 10 acres at 19534 Montevina Rd in Los Gatos. This rare hillside retreat offers three separate dwellings, combining luxury living, usable land, and flexible space just minutes from downtown. The main villa features 4 bedrooms and 3.5 bathrooms with breathtaking views of the San Jose city lights from its main living areas and outdoor spaces. Step into your private vineyard, which produces your own privatelabeled wine, and you are greeted by an impressive AutoHouse for car enthusiasts. The Auto House offers five car bays for collectors, plus an office and wet bar, creating an ideal setting for storage, display, and entertaining. Down the hill, a separate gated entry leads to a live barn with 8 stalls for livestock or equestrian use. Configured as a working farm, the barn includes laundry and a bathroom downstairs, with a fully permitted 2-bedroom, 2 bathroom living space upstairs. Perfect for ranch hands, rental income, guests, or returning adult children. Approximately 3 miles from Downtown Los Gatos, you enjoy privacy while still close to shops, dining, and amenities. Award winning schools, hiking trails and scenic views this is a property you don't want to miss!

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
$5,875,000
7 Beds ⋅ 5 Baths ⋅ ML82042840 MLS
Welcome to La Estancia, a rare historic estate in Glenridge, one of the towns most sought-after neighborhoods and just moments from exciting downtown Los Gatos. Originally crafted in the late 1800s and refined in 1901 by architect Willis Polk, whose work includes the famed Filoli estate in Woodside, California. This Mission Revival residence blends timeless character with exceptional privacy. Set behind gates on over 1.289 FLAT acres, the property features a grand main home, a guest house, a pool, a cabana, a detached oversized two-car garage, a 1,687 sq ft walkout basement with office and storage, and a tranquil pond with a water feature framed by mature trees. Expansive living spaces highlight rich architectural details, arched openings, and hillside views. Multiple indoor-outdoor areas create an ideal setting for entertaining or a quiet retreat.

18000 Overlook RD, Los Gatos

Listed by Donald Knight, 408-313-2191 from Coldwell Banker Realty
(If provided) CoList: Robin Sedgwick from Coldwell Banker Realty
$2,400,000
4 Beds ⋅ 3 Baths ⋅ ML82040577 MLS
Two homes, two separate addresses (20471 Black Rd and 20469 Black Rd), over 32 acres of beautiful land dropping down to a creek. Wide trail to creek and current owners take their dirt bikes on rides through the lower property. Incredible views, very peaceful. The main house has the primary suite on one side with a nearby second bedroom that can be used as an office. Two other bedrooms are on the opposite side of the home for privacy. One bedroom is an ensuite, the other has a bathroom just outside its door. Large laundry room. Kitchen, dining room and living room have incredible views of the nearby hills. Large orchard and multiple fruit trees including apple and Meyers lemons. Current owner is working to separate the two homes into two properties. both homes have their own addresses. Once separated, you could add an ADU to each home for rental income. If you enjoy hiking or offroad trail riding on private land, this property is for you. The second home has its own garage with an upper level storage area, 3 bedrooms, 1.5 baths, and a deck overlooking the hills and meadow. Zillow estimate is for only one home.

20471 Black RD, Los Gatos

Listed by Cassandra Maas, 408-472-7988 from Anderson Christie, Inc.
(If provided) CoList: from

Sold listing courtesy of Tanya Gianatasio from EXPCA
$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

$3,300,000
4 Beds ⋅ 3 Baths ⋅ ML82039619 MLS
Welcome to this beautifully remodeled and gated home in the heart of historic downtown Los Gatos. Thoughtfully updated throughout, it blends modern convenience with the warmth and character of its original design. The inviting living room features an original stone woodburning fireplace, creating a cozy place to gather. The chefs kitchen offers slab porcelain countertops, custom cabinetry, and topoftheline appliances, flowing into a dining room with builtin display cabinets and views of the outdoor entertaining areas. A spacious utility room off the kitchen provides excellent storage. The mainlevel primary suite offers a peaceful retreat with its spalike bathroom. A charming detached cottage adds wonderful flexibility with a full kitchen and bathroom ideal for guests, extended family, or a private workspace. Multiple outdoor spaces make entertaining effortless, including an outdoor kitchen with a barbecue, smoker, and refrigeration. Ideally located near toprated schools and downtown amenities, this home feels like a private sanctuary in the center of it all.

46 Pleasant ST, Los Gatos

Listed by Donald Knight, 408-313-2191 from Coldwell Banker Realty
(If provided) CoList: Robin Sedgwick from Coldwell Banker Realty

Sold listing courtesy of Shannon Ray from GGSIR
$2,280,000
2 Beds ⋅ 2 Baths ⋅ ML82036032 MLS
Rare single-story opportunity just moments from town! This charming 2BR/2BA home offers approx 1,252sf on a 3,600sf lot, plus a ~200sf casita. A winding brick pathway, classic picket fence, and expansive front porch create inviting curb appeal. Inside, the bright great room is ideal for everyday living and entertaining. The spacious kitchen features a breakfast bar, island, abundant cabinetry, and direct backyard access, with a convenient laundry closet. Beautifully refinished hardwood floors throughout. The secondary bedroom and hall bath are thoughtfully positioned for privacy. The expansive primary suite is a true retreat with a fireplace, walk-in closet, built-ins, recessed lighting, and private patio. The spa-like bath includes a stall shower, oversized jetted tub, dual vanities, and separate toilet room. Outdoor living shines with multiple paver patios, backyard TV sitting area, bistro lighting, vegetable planter boxes, and charming hidden dog house. The converted one-car garage offers a versatile detached casita with kitchenette, full bath, and laundry (without permits). Tons extra storage in casita attic. Close to downtown shops, dining, parks, and top-rated schools in a peaceful neighborhood setting. Electric vehicle charger and permit parking add to the convenience.

14 Cross WAY, Los Gatos

Listed by Nicolette Rodman Kelly, 408-483-8040 from Golden Gate Sotheby's International Realty
(If provided) CoList: Marlene Rodman from Golden Gate Sotheby's International Realty

Sold listing courtesy of Neen Martelino from GGSIR
$6,518,929
5 Beds ⋅ 5 Baths ⋅ ML82035234 MLS
Located in a highly desirable setting in the heart of downtown Los Gatos, this beautifully updated residence offers 3,429sq ft in the main home with 4 bedrooms and 3.5 baths, plus a flexible office/yoga studio, and the 5th bedroom is a detached 1-bed, 1-bath cottage (210 sq ft) ideal for guests, extended family, or private work-from-home retreat. Since 2018, the property has benefited from over $700K in improvements, including new A/C and furnace for the main home, new HVAC and hardwood floors in the cottage, and a fully integrated A/V and whole-home internet system. The kitchen has been thoughtfully refreshed with new Perrin & Rowe hardware, a professional Wolf gas range, complemented by a marble backsplash in both the kitchen and butler's pantry. Interiors are elevated by a striking stone fireplace wall in the great room and refinished hardwood floors throughout. The resort-style backyard is a true showpiece, completely reimagined with an outdoor fireplace and a built-in BBQ, earning 1st Place in the Medium Landscape Category (CLCA Awards, 2021). The improvements by JT Masters Construction reflect quality craftsmanship throughout. Dining, boutiques, Sunday Farmer's Market, trails, and more, this is turnkey living in one of Silicon Valley's most sought-after neighborhoods.

146 Tait AVE, Los Gatos

Listed by Steve&ChristinePerry, 408-391-4465 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of DeLeon Team from DLRPA
$5,995,000
5 Beds ⋅ 7 Baths ⋅ ML82033361 MLS
Legendary Chateau Liberte' is a landmark property at the Summit of Old Santa Cruz Highway, presiding over seventy-two pristine acres of towering Redwood forests. Main residence is restored with milled Redwood from the property. The income producing multiple rental dwellings include two cottages, a magical treehouse, and a secluded Cavco cedar cabin home. There is a large swimming pool, ponds, creeks, waterfalls with an underground prolific Artesian fed cistern supplying water to all the houses, pool, and ponds. Multiple fruit and nut trees with ten acres or arable land for vineyards of Pinot Noir and Chardonnay grapes. There is incredible horse property potential with manicured trails encompassing all 72 acres. The Williamson Act encompasses all parcels.Two RV sites with full utility hook-ups. 5,240 feet of security fencing with a security gate. Six-tenths of a mile private paved driveway. Your own private world awaits with rolling meadows, Koi and Turtles in the 360,000 gallon pond with it's own idyllic dock. Top Los Gatos Schools. APN# 558-04-045, 16 acres, SCC Cert. of Compliance included, 3 parcels total. Helicopter landing area. Only eight miles to the charming Los Gatos village. Majestic property. Lifetime opportunity for the next steward of the legendary Chateau Liberte'.

22700 Old Santa Cruz HWY, Los Gatos

Listed by George Rabe, 408-234-8238 from Intero Real Estate Services
(If provided) CoList: from

$11,000,000
6 Beds ⋅ 8 Baths ⋅ ML82030244 MLS
Spectacular single-story estate offering modern luxury, privacy & smart-home living in a prime Los Gatos location with top Saratoga schools. Sprawling contemporary residence set amid lush gardens, rolling hills & sweeping views. Generous interior features curated finishes & open living spaces with picture windows, skylights, high ceilings & custom woodwork, creating seamless indooroutdoor flow. Two private wings include six en-suite bedrooms & an executive office on the main level, including two primary suites with spa baths & custom built-ins, plus two J&J suites. Two laundry rooms, one of each wing. Sleek designer kitchen showcases a dramatic crescent-shaped island with walnut counter bar & premium Gaggenau, Perlick & Miele appliances. Family room features a striking metal entertainment console; living & dining rooms with walls of glass overlook the rear grounds. Lower level includes a bonus room, full bath, lounge & wine cellar. Resort-style outdoor living offers expansive patios, pool & spa, built-in BBQ, fire pit, play area, raised planter beds, bocce & horseshoe courts. Pool house/ADU with dressing area. Minutes to downtown Los Gatos, Saratoga Village, hiking & biking trails & an easy Silicon Valley commute. Refined, elegant & exceptional comfort for the most discerning!

16140 Matilija DR, Los Gatos

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

Sold listing courtesy of Kimberly Douglas from REEX
$3,700,000
4 Beds ⋅ 4 Baths ⋅ ML82020797 MLS
Welcome to a home designed for effortless living and unforgettable gatherings. This single level, newly built home combines soaring 18+ft ceilings with thoughtful details throughout, including an additional 2bed 990 sq ft ADU (total permitted: 3030sq ft). Built in 2024, the home features a gourmet kitchen, boasting custom cabinetry, Thermador stainless steel appliances, and beverage station complete with a built-in coffee machine. Flowing seamlessly into the living and dining spaces, its perfect for morning rituals or lively evenings w/ friends. Every detail has been carefully curated. Custom automatic shades, smart lighting, and custom Millgard windows invite natural light, while waterproof WPC flooring and custom thicker glass showers add both beauty and durability. Enjoy low-maintenance, drought-friendly landscaping, where manicured turf stays lush and green all year. Additional detached guest suite also offers a flexible private space designed for visiting guests, a home office, gym, or creative retreat. The separate 2 bedroom ADU offers a perfect opportunity for multigenerational living, extended family stays, or rental income. With leased solar and modern features throughout, this is more than a house, it is a lifestyle of convenience, comfort, and understated luxury.

15729 Linda AVE, Los Gatos

Listed by Pam Tran, 650-334-1993 from Loveseat Homes
(If provided) CoList: from

Sold listing courtesy of Vivian Lee from HMNRE
$5,250,000
6 Beds ⋅ 8 Baths ⋅ ML82017888 MLS
Set along one of Los Gatos most sought after ridge lines, this extraordinary estate captures sweeping yet intimate panoramas. Nearly every window frames views across downtown Los Gatos, Vasona Lake, the surrounding mountain ridges, and even the distant skylines of San Francisco, Oakland, and San Jose. Wrapped in privacy and framed by elegant landscaping, this breathtaking residence combines grandeur, comfort, and a deep connection to its natural setting. A tall wrought-iron entry door accented by mosaic glass opens to a grand foyer with volume ceilings and an elegant chandelier. Dual staircases sweep upward, creating balance and presence, while large windows allow natural light to pour in. Radiant heated marble and tile floors flow throughout the property for year-round comfort. The home unfolds with thoughtful flow and scale. With an expansive primary suite, four guest bedrooms, executive office, attached ADU with full kitchen and bath, detached pool house and two finished three-car garages, this estate is a home of scale, refinement, and enduring presence. With panoramic views dusk to dawn, an elegant design and resort-style amenities, it offers a true Los Gatos estate experience private, expansive, memorable, and a wonderful place to call home.

16383 Aztec Ridge DR, 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

Sold listing courtesy of Yan Tian from BOR
$6,940,000
4 Beds ⋅ 4 Baths ⋅ ML82017790 MLS
Don't wait! For a limited time Seller will entertain offers between $7.3M and $8M for the entire 9.6 acre property with ability to capture up to 3 legal developable parcels. One parcel currently offered for sale at $1.8M pending approvals (ML82017796). Options abound: keep the existing home while gaining two new parcels to develop or sell, offset costs by selling one or more parcels, or double the property's underlying value and hold for generational wealth. Arguably one of the finest estate properties in Los Gatos, this fully fenced and gated retreat offers unmatched privacy features sweeping 270 degree views of bucolic hills and the valley below. Despite being less than 5 minutes to Los Gatos Blvd, this multi-acre property features meandering trails wind through organic fruit trees, custom enclosures, and landscaped grounds with sunset vistas. Outdoor amenities include bocce, volleyball, swimming, and multiple gathering areas. The recently updated home is centered around a beautiful courtyard entry and features spacious bedrooms, a serene office, and multiple entertainment spaces. Expansive Brazilian Ipe decking surrounds the residence, framing sweeping hillside views. Located minutes from Los Gatos High, fine dining, and shopping, and served by top-rated Los Gatos schools.

15651 Kennedy RD, Los Gatos

Listed by Michael Riese, 408-781-7692 from Coldwell Banker Realty
(If provided) CoList: Collette D'amico from Coldwell Banker Realty

Sold listing courtesy of George Lee from FT23T
$4,250,000
4 Beds ⋅ 5 Baths ⋅ ML82016920 MLS
Outstanding property in downtown LG! Lovely Spanish Mediterranean w/ modern comfort & efficiency. Expanded & remodeled in 2012 w/ new systems, upgraded by current owner w/ designer finishes & fixtures. Wonderful interior space flows to spectacular rear yard! True indoor/outdoor living! Light-filled great rm w/ pic windows, coved ceilings, gas fireplace. Elegant oak flooring thru out. Spacious kitchen has glazed custom cabinetry, honed granite counters, professional-grade appliances, wine refrig. Exquisite hand-blown glass pendants over center island! Main floor has 2 bds that share adjoining bath. Upstairs 2 bdrm including spacious primary suite. Suite enjoys 2 custom walk-in closets, balcony, bath has beautiful Calacutta marble, dual vanity, steam shower & copper clad soaking tub imported frm Italy. 4th bed w/ pic window & full bath. Detached 2 car garage w/ attached guest unit offers additional living space w/ sitting rm, motorized Murphy bed, full kit/full bath. Rear yd is private sanctuary designed for leisure & celebration alike. Sparkling pool, jetted spa, outdoor fireplace, built-in BBQ & multiple lounging areas. Entertain in style or relax in your resort style paradise! Short stroll to shopping, dining & parks! Enjoy top Los Gatos Schools & convenient fwy access!

20 Mariposa AVE, Los Gatos

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

Sold listing courtesy of Irina Luck from APR
$7,350,000
5 Beds ⋅ 6 Baths ⋅ ML82015557 MLS
One-of-a-kind luxury estate set on ~30 acres with sunny pastures, redwood forest, & distant bay views. Impressive colonial style home with grand entry hall, formal living & dining rooms, family room, billiards room/library, wine tasting room with wine cellar, sumptuous primary suite with loft, 3rd floor recreation room & unfinished attic space, planned as home theater, has plumbing for half bath. All bedrooms have ensuite baths, 5th bed with wet bar over att. 3 car garage, and huge laundry room (potential 2nd kitchen). Detached guest house/legal ADU with own address: 3 beds/2.5 baths, sun room, private patio. Outdoor kitchen/living area with stone fireplace, European style pond with waterfall, beach entry & deck. Fenced gardens with custom pergola, mature orchard, bocce court. Fiberglass dome observatory with telescope, floodlit all-weather sports court, 60'x36' MD Barnmaster barn (inc. car lift, houses sellers' car collection), barn door raised for RV. Level/gently sloped fenced pastures, ample space to add a riding arena. Private trails through the redwood forest. Potential equestrian use, winery, organic farm, retreat/sanctuary. New roof, 22.5W solar system, auto generators for both houses. Only 1.5miles from Hwy 17, 8 miles/10-12 mins to downtown Los Gatos

23020 Old Santa Cruz HWY, 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

Sold listing courtesy of Amin Kuchaki Rafsanjani from PY2PP
$2,900,000
5 Beds ⋅ 4 Baths ⋅ ML82010797 MLS
We have the perfect landing spot for your blended family / Three residential homes just blocks from Downtown Los Gatos / Over an acre to create your own private estate or enjoy the primary residence of more than 3000 square feet with 5 bedrooms and 4 bathrooms / Separate cottage over 800 square feet with one bath / Studio built with permits is the perfect ADU or home office over 200 square feet / Four car garage / Additional out buildings include garden shed and artist studio and separate workshop / The property will be sold as is but that makes it ready for your improvement selections / You can choose hardwood or luxury plank flooring / You can replace the vinyl with tile / Decide if you want quartz or granite counters in the kitchen and baths atop your new custom cabinets / Maybe you will add dual pane windows and upgrade the heater and air conditioning / We encourage you to convert the wood burning fireplace to natural gas / You could compliment everything with warm color paint and may we suggest crisp white moldings / The low maintenance grounds might become your private vineyard / Take a stroll into town for the best of everything Los Gatos / Easy access to commute corridors will get you or your tenants quickly to the Coast or anywhere in Silicon Valley / Welcome Home !

100 Wood RD, Los Gatos

Listed by Brian Kiernan, 408-506-4017 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of RECIP from RCIP
$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
$7,450,000
5 Beds ⋅ 8 Baths ⋅ ML82008476 MLS
Château de la Vue | Elevated above Los Gatos, boasts over 9,500 sq. ft. of living space and presides over an ultra-private 2-acre estate where panoramic 180° views stretch from the lights of Silicon Valley to the skyline of San Francisco. This dual-gated compound offers an unmatched blend of security, tranquility, and architectural significance just minutes from downtown Los Gatos. The main residence spans over 7,000 sq. ft. with 4 bedrooms accompanied by 5 bathrooms and an executive office. The interior balances timeless luxury with dramatic indoor-outdoor flow, creating seamless entertaining experiences across expansive terraces, views, and landscaped grounds. A separate, over 2,200 sq. ft. guest house, accessed via its own gated driveway delivers full dual-living flexibility across two levels, each with its own kitchen, accompanied by 1 bedroom and 3 bathrooms. Ideal for multigenerational living or a private retreat. Resort-style amenities include a 75-foot lap pool and spa, movie theater, gym, and oversized 3-car garage.. Modern regulations make replication of an estate of this size, above ground, virtually impossible today. Chateau De La Vue is a generational opportunity to own one of Silicon Valleys most iconic, irreplaceable estates!

16541 Cypress WAY, Los Gatos

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

Sold listing courtesy of The Gummow Brothers from SGP
$6,250,000
4 Beds ⋅ 4 Baths ⋅ ML82001667 MLS
This private vineyard estate offers the essence of California resort-style living in a stunning setting near downtown Los Gatos. Secure gates open to an extraordinary property of nearly one acre with western hill views and professionally landscaped gardens, all bordered by a Zinfandel vineyard of 110 vines. Inside and out, the entire property was transformed into a serene and sophisticated retreat with amenities designed for year-round enjoyment. The floor plan is open and flowing, centered around a spacious great room that connects to the front and rear grounds, and a separate wing with the primary suite plus additional bedroom and bath. Private quarters upstairs offers flexible space with a central living area, bedroom, and bath ideal for office or guest suite. Separately a 1-bedroom, 1-bath guest house ADU with kitchen completes the accommodations. Outdoor living shines with a pool, spa, putting green, vast lawn, numerous fire pits, full outdoor kitchen, and automated louvered and heated lounges with outdoor media. Sustainable features include solar power, 3 Tesla Powerwalls inside the garage, EV charging, and a backup generator. Close to downtown Los Gatos and yet offering complete privacy, this rare opportunity invites an experience of California living at its finest.

114 Nina CT, Los Gatos

Listed by Gary Campi, 650-799-1855 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Anne Katzenmeyer from SRNO04
$2,415,000
4 Beds ⋅ 3 Baths ⋅ ML82003265 MLS
Single level 3bd 2ba, 2426sf± Main home PLUS 1bd 1ba, 840sf± Guest Home previously rented $3000+. Easy exit on Bear Creek Rd. and cruise the beautiful Old Santa Cruz Highway backroad straight to your front door! Just 4 short miles into Downtown Los Gatos, a rare opportunity to own over 2ac. of usable land. Both garage's set for Level 2 EV charging. Summer-ready backyard features a pool, pergola patio, propane plumbed in ready for your BBQ and firepits, grow your dream garden! Inside, natural light and lovely views in all living spaces, dine with stunning views. Kitchen and breakfast nook look out to vibrant green mountains and the pond! Separate family, living, and formal dining rooms are excellent to host gatherings. Unwind in your Primary Suite Retreat by the fireplace, or, rejuvenate in your spa bath with sauna, shower for two, so much natural light, and sliding glass doors to an idyllic private patio. Mn hm: 2-car gar., 1 carport. Gst Hm: 1-car gar., 1 carport, Other features: potential rental income or multi-gen. living, zoned heat, pre-wired for video/audio, laundry rm, deer fence. Los Gatos schools. Multiple routes to and from the home, take backroads to the beach or around town, easy access to hiking and biking!

18301 Idylwild RD, Los Gatos

Listed by Paula L Leary, 408-425-3345 from Golden Gate Sotheby's International Realty
(If provided) CoList: Kathryn Harrold from Golden Gate Sotheby's International Realty

Sold listing courtesy of Asif Subedar from COMPS
$3,065,000
6 Beds ⋅ 5 Baths ⋅ ML82002323 MLS
Welcome to 16460 Wood Acres Rd in Los Gatos with Saratoga Schools. This unbelievable property has 2 residences. The main structure is completely remodeled in 2025 and has nearly 2800 sq ft, 3 bedrooms and 3 bathrooms and unforgettable views of the Silicon Valley. Soaring ceilings, open kitchen concept, a commercial grade prep kitchen, and a serene retreat of a primary bedroom. The guest cottage is over 900 sq ft with 3 bedrooms and 2 bathrooms. Equipped with everything you need for in laws, rental, or full time living. This property has over an acre of land, and has a swimming pool with a custom water slide, a private driveway with new asphalt and retaining walls. Do not miss out on this multi generational property that is beautifully remodeled and designed with high end finishes! The views make this property one of a kind!

16460 Wood Acres RD, Los Gatos

Listed by Erfan Modir, 408-772-1275 from Intero Real Estate Services
(If provided) CoList: Bobby Chiorean from Intero Real Estate Services

Sold listing courtesy of John Wu from GEMH
$1,750,000
5 Beds ⋅ 2 Baths ⋅ ML81995388 MLS
Exceptional Property with Main House & Cottage. Prime Location near Hwy 17 & Summit. A rare opportunity, this fenced and gated property offers usable land in a highly desirable location just minutes from town. Enjoy the beauty of established landscaping, gardens, and a tranquil pond, creating a serene retreat. The main house features custom kitchen cabinetry, seamlessly opening to the family room. Wood floors. Luxurious primary suite with a recently renovated spa-like bathroom. A dedicated office or bonus room for added versatility. Sunroom filled with natural light. Spacious utility room for extra convenience. A separate 1-bedroom, 1-bathroom cottage provides additional flexibility, ideal for guests, a home office, or rental potential. Frontier Fiber Internet. Enjoy easy access to local amenities, including Summit Store, wineries, top-rated schools, and coastal beach towns. Served by award-winning schools: Loma Prieta Elementary, C.T. English Middle School, and Los Gatos High.

17615 Mountain Charlie RD, Los Gatos

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

Sold listing courtesy of Heidi Herz from GGSIR
$8,000,000
4 Beds ⋅ 5 Baths ⋅ ML81999864 MLS
Absolutely stunning home by renowned architect Gary Kohlsaat in the highly desirable Surrey Farms Neighborhood. Set on an immaculate half an acre, this luxurious farmhouse style property blends modern luxury with seamless indoor-outdoor living checks all the boxes! An open concept kitchen and family room with side by side La Cantina doors completely opens to the resort-like backyard. Perfect 800 sq ft pool house. Custom designer materials and fixtures throughout. The primary suite offers a spa-like retreat, private deck, along with custom his and hers walk-in closets. Oversized game room with La Cantina doors. Impressive cedar wood details throughout the interior and exterior. The incredible loggia has a gas burning fireplace, skylight, TV, outdoor kitchen with Evo grill. The yard is perfect for entertaining & family fun with a pool, hot tub, large turf lawn, kids play structure, built-in trampoline, gas fire pit, sauna & outdoor shower. Pool house has living room, legit gym & full bathroom. Gym room was designed as an optional bedroom. Ground level bedroom has an en-suite bathroom. Beautiful dedicated office with custom built-in cabinets. Massive 973 sq ft garage with epoxy flooring & built-in storage cabinets. Great mud room. Extensive smart home features. Just perfect!

140 Twin Oaks DR, Los Gatos

Listed by Greg Simpson, 408-832-2323 from KW Bay Area Estates
(If provided) CoList: from

Sold listing courtesy of Fran Papapietro from SGP
$4,630,000
5 Beds ⋅ 5 Baths ⋅ ML81995456 MLS
Discover luxury, privacy & serenity with this breathtaking Los Gatos estate, custom-designed and set on nearly 5 acres of pristine land. A gated bridge over a tranquil creek leads to a 3BD/2.5BA main residence and a 2BD/1BA guest unit above the detached 2-car garageideal for guests, multigenerational living, or private office. Surrounded by majestic oaks and rolling hills, this elegant home features soaring ceilings, expansive Anderson windows, and a dramatic stone fireplace. The chefs kitchen is a culinary dream with Sub-Zero, Viking, Dacor appliances, custom cabinetry, and granite countersflowing seamlessly into a spacious family room filled with natural light. Step outside to your private resort-style oasis with a sparkling pool, spa, built-in BBQ, and two pool rooms with showers, sinks & toiletsperfect for entertaining. Equestrian amenities include a barn, two paddocks, fenced pasture, ample storage, and direct access to miles of scenic riding/hiking trails with panoramic valley views. Additional highlights include a temperature-controlled wine room, workshop, storage rooms, and cabana bath. Located minutes from vibrant downtown Los Gatos and zoned for top-rated Blossom Hill Elementary, Fisher Middle, and Los Gatos High. A truly exceptional lifestyle estate.

14205 Shannon RD, Los Gatos

Listed by Boyenga Team, 408-373-1660 from Compass
(If provided) CoList: from

Sold listing courtesy of Lara Carlson from COMPS
$1,550,000
4 Beds ⋅ 3 Baths ⋅ ML81992962 MLS
Welcome to your dream mountain getaway! This beautiful dome house is surrounded by towering redwoods, offering stunning views and plenty of land to explore. You will adore the charming shingled exterior and spacious wraparound redwood deck perfect for enjoying natures beauty. Step inside, and you'll be welcomed by floor-to-ceiling sliding glass doors that seamlessly blend indoor and outdoor living. The newly remodeled kitchen and living area create a warm, open atmosphere, ideal for entertaining friends or enjoying some quiet time. And you will love the master suite! Its a private retreat featuring dual walk-in closets and a luxurious bath with natural stone, an oversized tub, and a spa-like showerjust what you need to unwind after a long day. There are also two additional bedrooms, great for family, guests, or even a home office. Plus, a detached 1-bedroom ADU with its own full kitchen and bath is perfect for rental income or as a cozy spot for family. The spacious yard is a blank canvas for your creativitythink gardens, play areas, or serene relaxation. With top-rated schools nearby and easy access to Hwy 17, youll enjoy both tranquility and convenience. Dont miss out on this incredible opportunityschedule a visit today and start envisioning your new life here!

24706 Hutchinson RD, Los Gatos

Listed by Mojgan Nematollahi, 408-221-7567 from The Agency
(If provided) CoList: Gerry Geoghegan from The Agency

Sold listing courtesy of Daniela Alvarez from NTERO
$3,200,000
3 Beds ⋅ 4 Baths ⋅ ML81992011 MLS
Opportunity abounds, with this 17,402 square foot lot in a desirable and quiet Los Gatos neighborhood. Mediterranean style home including an interior patio with access from the spacious living/dining room (16X23) and kitchen. This Spanish patio format is an entertainer's dream. Three full baths in the main home. The kitchen includes a JennAire range and oven, there is a second oven, wrap around granite counter tops and built-in microwave. The kitchen eating area includes a breakfast bar, a light filled breakfast table area and built in desk and cabinets. Dual paned windows and recessed lighting. Behind the detached two car garage is an ADU or in-law quarters, with mini kitchen and additional full bath. Did I mention the third of an acre park like lot? Long gated driveway to detached garage. Possible lot split? Another lot on the street just received approval of a lot split on a similar size lot.

16156 Camino Del Sol, Los Gatos

Listed by Dennis Moreno, 408-888-2553 from MGM Real Estate
(If provided) CoList: Laura Moreno Little from MGM Real Estate

Sold listing courtesy of Deepak H Chandani from COMPS

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