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$1,800,000
3 Beds ⋅ 3 Baths ⋅ ML82030169 MLS
This 3 bed/ 3 bath Los Gatos exclusive is a must see. Over 5 acres of gated serene mountain living near Highway 17 in the coveted Loma Prieta School District. The home has over 2500- sq.ft. of beautifully remodeled space. The vaulted ceilings, sky lights, and huge picture windows capture spectacular daylight on the main floor, making the gourmet kitchen with its stainless steel appliances, gas range, handpainted ceramic backsplash, soap stone counters, and two islands the envy of any home chef. Theres a formal dining room/den with a half bath and a great room with a fireplace and access to the upper deck, where you can take in the sweeping mountain views beneath a pergola. Also on the main floor, a retreat style primary bedroom and a primary bathroom with a standalone soaking tub, dual vanities and a bay window for extra sunlight. On the lower level, youll find the remaining bedrooms, bathroom, storage area and access to the lower deck. Outside, theres an attached 2 car garage, detached office/artist studio, chicken coop, and a 4 car detached garage with a separate driveway perfect for an ADU. There are too many incredible features to list; youll have to see for yourself!

23695 Hutchinson RD, Los Gatos

Listed by Katie Keeler, 831-588-6959 from eXp Realty of California Inc
(If provided) CoList: from

$974,999
2 Beds ⋅ 1 Baths ⋅ ML82050444 MLS ⋅ Chemeketa Park BLDG.
Charming Los Gatos redwood retreat blending cabin vibes with modern updates! This 1,128 sq ft home features 2 main-level bedrooms and a large tiled bath. The layout has no hallways, feeling extra spacious. The kitchen boasts green marble, pine, checkerboard flooring, a gas cooktop, and stainless appliances (washer/dryer incl.). Enjoy a formal dining room, family room, and flex space. Downstairs is a 385 sq ft finished basement with laundry, a workshop, and storage. Stay cozy with propane central forced air, a propane water heater, and a wood stove with winter wood provided. Upgrades include a 2019 roof and a Tesla Level 2 EV charger. Outside, enjoy an 850 sq ft sunny deck, terraced yard, and private patio. Located in a top school district just 14 minutes to the high school! The $218/ mo fee covers water, roads, and community amenities.

20905 Comanche TRL, Los Gatos

Listed by Brant Schenk, 831-227-5739 from eXp Realty of California Inc
(If provided) CoList: from

$900,000
4 Beds ⋅ 3 Baths ⋅ ML82054756 MLS
Luxury Live Auction! Bidding to start from $900,000.00! A rare opportunity to steal this private mountain estate on ~5 acres in the Los Gatos Mountains, just appraised at $1.45M. This beautifully renovated and move-in ready retreat delivers breathtaking panoramic views spanning mountains to city lights, where luxury meets serenity. Behind a gated, tree-lined drive, discover a stylish 4BD/2.5BA main residence (2,134± SF) plus a detached ADU ideal for guests or multigenerational living. The designer kitchen features custom cabinetry, marble counters, gas range & walk-in pantry. Expansive living spaces open to multiple view decks for seamless indoor-outdoor living. Equestrian-ready with flat usable land, paddocks & riding area. Recent upgrades include new roofs, hardwood floors, A/C & so much more, must see to appreciate. Now launching via luxury auction - where market demand meets opportunity.

30680 Loma Chiquita RD, Los Gatos

Listed by Sandy Jamison, 408-214-8821 from Tuscana Properties
(If provided) CoList: The Jamison Team from Tuscana Properties
$900,000
2 Beds ⋅ 2 Baths ⋅ ML82052436 MLS ⋅ Aldercroft Heights BLDG.
Amazing views above Lexington Reservoir from this updated Aldercroft Heights Home! Discover this custom-built gem by Pacific Modern Homes (approx 1992), designed for durability and comfort. The interior is bathed in natural light from stunning arched picture windows and french doors, centered around a dramatic living room with soaring vaulted ceilings that create an airy, open sanctuary. The home offers a highly functional layout, with 1 one bedroom & bath upstairs, and another bedroom & bath downstairs, including a spacious basement with a dedicated laundry area. Recent updates include new exterior paint, new wideplank flooring, updated bathroom vanities and fixtures. Featuring the renowned "Pacific SmartWall System," this residence is built with robust construction offering peace of mind in a beautiful, natural setting. Two levels of lovely covered decks are perfect for enjoying morning coffee or serving as a peaceful space. Outdoor living is a dream with breathtaking mountain views with a peek at the reservoir and small yard for gardening and play. Friendly Aldercroft Heights community & proximity to Lexington Reservoir for kayaking, fishing and hiking. Great Commute; 10 minutes to town and best Los Gatos Schools: Lexington Elementary, Fisher Middle and Los Gatos High!

17415 Locust DR, Los Gatos

Listed by Nicki Banucci, 408-515-7247 from Compass
(If provided) CoList: Lisa Sgarlato from Compass
$1,250,000
2 Beds ⋅ 2 Baths ⋅ ML82021608 MLS ⋅ Redwood Estates BLDG.
Charming home located in the highly desirable Redwood Estates Community. The spacious floor plan includes 1410 sq ft of living space, two large bedrooms and two fully renovated bathrooms. The modern kitchen and dining area opens up to a large backyard, perfect for enjoying your morning coffee or hosting a dinner party. Incredible opportunity for expansion: take the spiral staircase upstairs to an unfinished second floor with about ~1000 sq ft. Recent upgrades include tankless water heater, copper plumbing, and whole house generator. Enjoy the serenity and calmness of living in the redwoods yet being only moments away from Downtown Los Gatos with premier shopping and dinning. Residents enjoy access to a swimming pool, two playgrounds, and a community center. Award winning Los Gatos schools: Lexington Elementary, Fisher Middle, and Los Gatos High School.

18143 Gloria CT, Los Gatos

Listed by Dhara Mehta, 408-646-3404 from Redfin
(If provided) CoList: from

$1,499,000
3 Beds ⋅ 3 Baths ⋅ ML82053710 MLS ⋅ Redwood Estates BLDG.
Wonderfully updated and comfortable REDWOOD ESTATES private home. Quality upgrades, fine craftsmanship, high functionality are highlights of this tastefully updated sunlit abode. Spectacular sunrises on sprawling decks with panoramic views of the lush and inspiring Sierra Azul. Huge usable lot welcomes creativity for vast gardening, pets, pool, ADU? or a variety of uses. The updates to this home include EV charger, on demand h20, back up whole house gen, high capacity AC, designer - paints, trim, lighting, switches, outlets, hardware, doors, Calif. closets, hardwoods, custom front door and trim pkg, hardwood floors, dbl pane windows, marble counters, deep sink, elec. blinds, designer hardware, copper gutters, downspouts and ext. lighting, built ins, murphy bed, Kitchen Aid appliance suite. Vaulted ceilings & skylight, large hearth and mantle, great floor plan offers fine livability. Neighborhood pool, pavilion, park, pizza place, playing field and convenience store provide a community hub adjacent to a large SCC Fire Station. World Class Los Gatos public schools, easy access freeway corridors and proximus to silicon valleys biggest tech campuses, SJC, SFO and downtown's Los Gatos finest entertainment, dining and shopping. You wont find this kind of living for this kind of price.

21546 Alma CT, Los Gatos

Listed by Drew Reid, 408-515-1362 from Coldwell Banker Realty
(If provided) CoList: from

$3,035,000
3 Beds ⋅ 3 Baths ⋅ ML82053525 MLS
Immaculately maintained and thoughtfully upgraded, this exceptional private estate is just 5.3 miles from downtown Los Gatos. Set on nearly 2 beautifully landscaped acres of rare, all-usable land, the front yard overlooks a gently sloping 1+ acre meadow with expansive long-range views, while the backyard is framed by mature forests, creating a peaceful and private setting. Offering approximately 3,000 sq ft of living space, including a private 512 sq ft studio apartment with its own entrance, the property is ideal for guests, extended family, a home office, or rental income. The main home features 3 bedrooms, 2 baths, a versatile loft, vaulted ceilings, abundant natural light, and a spacious great room. The kitchen offers generous space for cooking and entertaining. Amenities include a black-bottom micro-pebble pool with automatic safety cover, a 120 sq ft climate-controlled wine cellar, fully deer-proof orchard with 25 mature fruit trees, automated irrigation throughout the property, finished heated garage/fitness studio, separate laundry, utility and mechanical rooms, tool/equipment shed, recent 50-year roof, new 3-zone HVAC, backup generator, security system, water softener, and reverse osmosis drinking water system.

20378 Black RD, Los Gatos

Listed by Michael R Simpson, 650-207-1126 from Cruz Properties
(If provided) CoList: from

$1,195,000
4 Beds ⋅ 3 Baths ⋅ ML82043742 MLS
Nearly 3 acres across two buildable legal parcels, HS-SR zoned, positioned on Highway 17 at the intersection of Silicon Valley work, Los Gatos schools, and Santa Cruz Mountain living. This 4BD/3BA, 1,855 sq ft home is genuinely turnkey: freshly painted interior and exterior, new carpet throughout, owned solar system, Tesla Powerwall battery backup, EV charging, and a detached workshop. Mutual water, septic. Sits in the Lexington Elementary, Raymond J. Fisher Middle, Los Gatos High (rated 10/10) school triangle. 15 minutes to downtown Los Gatos and top-rated schools. 20 minutes to Silicon Valley employment centers. Steps to world-class hiking and biking trails. Weekend accessible to Santa Cruz and Monterey Peninsula. Second parcel buildable, subject to county approval and buyer verification genuine flexibility without obligation. Built for buyers seeking land, schools, infrastructure investment, and access without compromise.

20476 Santa Cruz HWY, Los Gatos

Listed by Michael Riese, 408-781-7692 from Coldwell Banker Realty
(If provided) CoList: Sunil John from Coldwell Banker Realty
$900,000
2 Beds ⋅ 2 Baths ⋅ ML82052618 MLS ⋅ Redwood Estates Services Associa BLDG.
Charming and Sought After Redwood Estates Cottage! This 2-bedroom, 2-bath home offers approximately 1150 sq ft of living space on a 5,850 sq ft lot. Enter to high ceilings, sunny space with skylights, windows, patio sliders and french doors throughout providing ambient light. Wide plank wooden flooring in living room combine with kitchen. The kitchen is equipped with tile countertops, a gas cooktop and oven range, dishwasher, refrigerator, and exhaust fan and eat-in bar. Spacious deck off of kitchen for relaxing under the lovely mountain views. Primary bedroom with carpeting and ceiling fan and a full bathroom with a shower over tub are on the upper floor. Spiral staircase leads to lower level with 2 adjoining rooms for den plus bedroom combo and full bathroom along with large basement storage space. Step outside where your hot tub awaits amongst the garden space. Laundry is conveniently situated in the utility room with 220V electricity hookup and washer/dryer included. Central heat and wired for generator. Friendly community with pool, playgrounds, community center, new fire station, Pizza restaurant, post office and general store in a great commute location 7 minutes to town. Great Los Gatos Schools: Lexington Elem, Fisher Middle, Los Gatos High

21590 Madrone DR, Los Gatos

Listed by Lisa Sgarlato, 408-396-7231 from Compass
(If provided) CoList: from

$1,075,000
3 Beds ⋅ 2 Baths ⋅ ML82050409 MLS ⋅ Chemeketa Park BLDG.
Charming and Sunny Los Gatos hills retreat! Located in Chemeketa Park, just minutes to town, this 1,448 sq ft home sits on a 18,000+ sq ft lot and offers three bedrooms and two bathroom. The living room features a wood-burning fireplace and vaulted ceilings, while the flooring combines laminate and carpet throughout. The kitchen includes quartz countertops, an oven range, microwave, hood over the range, and refrigerator, with an eat-in dining area. Bedrooms are on the ground floor, including the primary with a stall shower; the full bathroom features a shower over tub. Central forced air heating and ceiling fans provide comfort. Laundry is conveniently located inside with washer and dryer hookups. Amazing entertainers back yard! Covered patio with built in kitchen featuring bbq and granite counters plus sitting area with TV and Gas fireplace. Property includes a shed and an electric vehicle Level 2 (240 volts) hookup. Friendly Chemeketa park community features playground and community room also includes water company. Near Lexington reservoir with hiking, biking trails, fishing and kayaking. Fantastic commute location close to downtown Los Gatos. Los Gatos Schools featuring Lexington Elementary (IB Programme), Fisher Middle and Los Gatos High

17666 Navajo TRL, Los Gatos

Listed by Lisa Sgarlato, 408-396-7231 from Compass
(If provided) CoList: Charles Holcomb from Compass
$975,000
2 Beds ⋅ 2 Baths ⋅ ML82051193 MLS
Escape to the tranquility of the Santa Cruz Mountains without giving up proximity to town. This move in ready Redwood Estates retreat was rebuilt down to the studs in 2015 and blends modern comfort with the natural beauty of its redwood surroundings. This home offers light-filled spaces designed for today's lifestyle. An open-concept floor plan creates seamless flow between the living area and well-appointed kitchen, featuring granite countertops, breakfast bar seating, and abundant cabinetry. Wood window framing, crown molding, and travertine flooring add warmth and quality throughout. The floor plan offers space well suited for a home office, creative studio, or guest accommodations. Privacy surrounds the property, while ample parking provides a valuable advantage. Approx.10 min. from Downtown Los Gatos, enjoy convenient access to shopping, dining, recreation, and major Silicon Valley employment centers while maintaining the serenity and beauty of mountain living. Those seeking a full-time residence, a quiet retreat, or a place to recharge will find the perfect balance of accessibility and escape. In the highly regarded Los Gatos School District, this is a rare opportunity to enjoy modern living, natural beauty, and a highly sought-after location all in one special property.

21568 Alma CT, Los Gatos

Listed by Kathleen Hendricks, 831-917-0839 from Sotheby's International Realty
(If provided) CoList: from

$2,750,000
5 Beds ⋅ 4 Baths ⋅ ML82049542 MLS
Perched on a picturesque 2.25 acres of sunny, usable land with mountain & partial ocean views in the desirable Los Gatos Mountains, this beautiful updated home offers 3,417 sq ft of living space just mins from Hwy 17. The gourmet kitchen features Viking & Thermador appliances, Miele built-in coffee system, center island, & custom cabinetry. The kitchen opens to the dining & living rooms with soaring ceilings, abundant natural light, & wood-burning fireplace. A lower level family room offers space for entertaining with access to the outdoor patio. The spacious light filled primary suite features a remodeled bathroom with soaking tub, oversized shower & dual walk-in closets. The outdoor amenities include an expansive covered pergola with custom bar, dining & lounge areas ideal for large gatherings or events, fire pit, sports court, & detached game room. The fully fenced gated grounds offer open lawn areas, mature redwoods, a hot tub with serene mountain views, ample parking & multiple outdoor spaces to unwind. Additional highlights include owned solar, whole-house generator, a 400 sq ft 1-bed 1-bath guest unit ideal for multigenerational living or rental income. Served by the exceptional Los Gatos-Saratoga High School District. 15 mins to Los Gatos and 20 mins to Santa Cruz.

23457 Summit RD, Los Gatos

Listed by Suzanne Merrick, 408-416-7130 from Christie's International Real Estate Sereno
(If provided) CoList: from

$1,850,000
4 Beds ⋅ 3 Baths ⋅ ML82047653 MLS
Sun-filled Aldercroft Heights home with awesome canyon views and privacy behind a motorized gate, less than 15 minutes from downtown Los Gatos. Updated main level offers a modern kitchen with breakfast nook, spacious living room with wood burning fireplace, 3 bedrooms/2 bathrooms, and a sunroom for extra living space. Flexible layout includes potential office or formal dining room. Includes high ceilings, ceiling fans, french doors, and other details. Lower level includes an additional en-suite bedroom/bathroom, 2 wood stoves, large entertainment room with the opportunity to create a separate unit with private entrance, and lots of charm! Multiple decks, additional structures for studio/office/workshop, new attic insulation, and completed inspections. Includes parcel (APN #558-22-018) across the street. Excellent schools. A unique property with abundant space, views, and endless possibilities! Twilight/furnished photos are virtual.

20955 Panorama DR, Los Gatos

Listed by Kathy Royer, 408-391-6200 from Coldwell Banker Realty
(If provided) CoList: from

$1,500,000
5 Beds ⋅ 3 Baths ⋅ ML82050416 MLS
Incredible Price! Best value in Los Gatos! Almost heaven, a timeless Spanish estate style ridge top property with 360 degree views of Santa Clara County and the Pacific Ocean! Open floor plan with soaring ceilings showcases a sophisticated design that radiates luxury and comfort. With 5 bedrooms plus den/office and 2 and a half bathrooms, this home offers ample space for relaxation and entertainment and an abundance of expansive windows that flood the home with natural light and offering breathtaking views from every room. Living/Dining room has vaulted ceiling and a cozy fireplace and sliders to the outdoors. Gourmet kitchen with ample counter space, a built-in oven, electric stove with grill, garbage compactor, and a pantry. Primary suite with sliders offering valley views, two walk-in closets, bathroom with dual sinks, a large soaking tub, and a separate stall shower. potential 2 more ensuite bathrooms (plumbing under floor). 3 car garage, room for RV, 5 acres sunny flat land with barn, potential horse property. Easy to convert Barn to ADU. Riding trails nearby. Great well, Starlink and satellite internet available. Award Winning Los Gatos Schools: Lexington elem (IB Programme), Fisher Middle and Los Gatos High. Worth the scenic drive to this slice of paradise!

16420 Soda Springs RD, Los Gatos

Listed by Lisa Sgarlato, 408-396-7231 from Compass
(If provided) CoList: from

$1,067,000
2 Beds ⋅ 2 Baths ⋅ CC41137874 MLS
Fully remodeled 2-bedroom, 2-bath home in the highly sought-after Los Gatos school district, just 8 minutes from vibrant downtown Los Gatos. This exceptional redwood retreat offers the rare combination of modern comfort, natural beauty, and everyday convenience. Nestled among towering redwoods in the desirable Redwood Estates community, the home seamlessly connects with its surroundings through soaring ceilings, warm wood accents, abundant natural light, and timeless architectural character. Thoughtfully updated throughout, it preserves original charm while incorporating modern upgrades for today's lifestyle. Designed for both everyday living and effortless entertaining, the open-concept layout flows naturally between indoor and outdoor spaces. The updated kitchen features real wood cabinetry, brand-new appliances, an oversized granite workstation sink, and a charming arched doorway. The living area opens to a newly stained deck overlooking the forest canopy, creating a seamless extension of the home - ideal for morning coffee, outdoor grilling and dining, entertaining, or relaxing among the trees. The spacious primary suite offers a true retreat with room for a king-sized bed and additional furnishings. The newly remodeled spa-inspired bathroom includes a deep soaking tub, rain

18103 La Verne Dr, Los Gatos

Listed by Carissa Brikken Brown, (925) 209-4842 from Christie's Intl RE Sereno
(If provided) CoList: from

$5,000,000
2 Beds ⋅ 2 Baths ⋅ ML82050479 MLS
Set across approximately 30.9 gently rolling acres at approximately 2,400 feet in elevation within the prestigious Santa Cruz Mountains AVA, Ascona Vineyards is a distinguished wine country estate that seamlessly blends agricultural functionality with timeless architectural elegance. Sweeping vineyard and countryside views frame approximately 16 acres of organically farmed vines planted with a curated collection of premium grape varietals, presenting a rare opportunity for boutique wine production, lifestyle ownership, or long-term legacy investment. **Accepting BackUp offers** At the heart of the estate, the Tuscany Revival farmhouse evokes the warmth and character of a refined European vineyard retreat. Thoughtfully positioned to capture the surrounding natural beauty and tranquil setting, the residence features luxurious finishes, inviting living spaces, and an effortless connection to the landscape. Designed for both private enjoyment and commercial vineyard operations, the property is fully fenced and extensively improved with a professionally designed winery facility, utility and storage buildings, and infrastructure supporting ongoing production and future expansion.

18516 Skyline BLVD, Los Gatos

Listed by Billy Caruso, 408-304-4872 from KW Bay Area Estates
(If provided) CoList: Danielle Davenport from KW Bay Area Estates
$1,499,000
2 Beds ⋅ 1 Baths ⋅ ML82048729 MLS
APN 562-31-014 & APN 562-31-013. Mountaintop Privacy & Panoramic OCEAN & City Lights Views at 15880 Soda Springs Road, Los Gatos. Perched high above Silicon Valley on nearly eight acres of pristine hilltop land, Two lots of record, 15880 Soda Springs Rd offers a rare combination of seclusion, scale, & truly sweeping views, while remaining just 20 minutes from the heart of Los Gatos. The property sits adjacent to the 19,000 acre Sierra Azul Open Space Preserve, protected by Santa Clara County's High Scenic zoning. This not only safeguards long-term views and value, but also provides direct access to miles of scenic trails for hiking or horseback riding. This is a property designed for those who value privacy, nature, and the freedom to create a legacy estate in one of Northern California's most desirable mountain settings. On this property is a charming English style home that blends comfort with character. Featuring high ceilings, large casement windows flooding the interior with natural light, wood flooring throughout, a spacious attic for storage or future living space, and an expansive deck ideal for enjoying sunsets, coastal breezes, and starlit evenings. Opportunity to live in the existing home while creating your dream custom home and/or luxury equestrian estate.

15880 Soda Springs RD, Los Gatos

Listed by Monterey Peninsula Home Team, 831-601-3284 from KW Coastal Estates
(If provided) CoList: from

$949,000
2 Beds ⋅ 2 Baths ⋅ ML82048722 MLS ⋅ Chemeketa Park BLDG.
Charming Mountain Home with Custom-Built Cabin Retreat in the Hills of Los Gatos Escape to this peaceful, wooded Los Gatos hills home mountain living with Silicon Valley convenience. The living room features new windows opening to a sunny deck with forest views. The gourmet kitchen boasts custom cabinetry, center island, new LG appliances with double oven, gas range, and walk-in pantry with washer/dryer. Primary suite offers walk-in closet and tiled shower. One additional bedroom and a flex for family, guests, or office. Outside, a restored 121 sq ft custom cabin suits guests, studio, gym, or home office. Deck overlooks Los Gatos Creek with under-deck storage. Recent Improvements: New flooring, Expanded windows, New roof, Kitchen remodel, Furnace, Water heater, Electrical panel & gateway, 2 Tesla Powerwalls, 220V EV charger, Landscape lighting, Retention walls, Refurbished cabin Community: playground, garden & clubhouse with hikes and events. Location 6 min to Lexington Elementary (IB World School) Feeds Fisher Middle & Los Gatos High, Hwy 17 access, Minutes to downtown, Lexington Reservoir & redwood trails, 2 fire stations nearby (incl. S-70i Firehawk) Ideal for families, remote workers, or anyone craving mountain charm near the Bay Area. Book a showing today.

20851 Assiniboine TRL, Los Gatos

Listed by Dan Hunnicutt, 650-704-5628 from eXp Realty of Northern California, Inc.
(If provided) CoList: from

$5,500,000
3 Beds ⋅ 2 Baths ⋅ ML82047686 MLS
A rare fully improved private estate compound opportunity in Los Gatos. Set across 8.23 secluded acres just 15 minutes from downtown, this extraordinary property offers immediate luxury living today and a dramatically accelerated path to a future world-class custom estate. Accessed through two secure electric gates and a long stone-paver drive, the property includes an architecturally designed luxury guest residence with sophisticated smart-home integration, floor-to-ceiling glass, automatic shades, wide-plank engineered hardwoods, quartz finishes, steam shower, expansive view deck, spa, dual EV charging, and high-speed Starlink connectivity. What makes this offering exceptionally rare is the immense infrastructure and time-compression value already in place: premium flat buildable estate area, completed site work, permitted septic infrastructure, domestic well, substantial water storage, advanced solar + intelligent battery microgrid, and the ability to bypass years of planning, excavation, and development complexity. A true private sanctuary with top Los Gatos schools, exceptional proximity to Silicon Valley, and extraordinary optionality for the visionary buyer seeking a legacy estate, luxury retreat, or multi-generational compound.

19751 Hicks RD, Los Gatos

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

$3,590,000
5 Beds ⋅ 4 Baths ⋅ ML82038848 MLS
Three Homes, Endless Possibilities. First time on the market ever! This extraordinary Chalet-style estate offers a true Lake Tahoe feel just 10 minutes from downtown Los Gatos with award-winning Los Gatos schools. Nestled on approximately 3.85 scenic acres surrounded by majestic redwoods and breathtaking views, this custom-built 1971 estate delivers privacy, versatility, and natural beauty. The main residence features 5 bedrooms and 4 full baths with soaring vaulted ceilings, expansive windows, formal dining room with views, oversized family room with distant views of Lexington Reservoir, and a sunroom designed to capture spectacular morning sunrises. The expansive deck & swimming pool create the perfect setting for entertaining and indoor-outdoor living. A private attached casita with a giant loft offers ideal accommodations for guests or extended family. Two detached rented ADUs provide immediate income while maintaining privacy. One unit, built in the early 2000s, is 1,200 SF with a chef inspired kitchen, while the 2nd ADU is nearly 1,000 SF. This estate is not just for horses; it's built for horsepower, featuring both a 2 car garage & oversized 4-car garage with high ceilings for large vehicles. A rare Los Gatos opportunity combining luxury, income, privacy, and lifestyle.

20100 Black RD, Los Gatos

Listed by David Conti, 408-896-4081 from KW Bay Area Estates
(If provided) CoList: from

$2,998,000
5 Beds ⋅ 3 Baths ⋅ ML82042111 MLS
Offered by the Kennedy Estate as part of a multiparcel disposition, this 3,378 sq ft residence along with APN 562-01-038 will be sold together making approximately 79 total acres, presenting a rare large acreage opportunity in the Los Gatos mountains. Built in 1925, the home features five bedrooms, three bathrooms, an attached garage, and a detached garage. The land highlights the properties long history in the region, with natural terrain, established improvements, and a mature apple orchard that has been part of the landscape for many years. The location reflects a largescale ownership footprint within the Loma Prieta community, offering notable acreage, enduring character, and a setting that showcases the scale and presence of this mountain property.

24580 Loma Prieta AVE, Los Gatos

Listed by Gregg Fussell, 408-857-0957 from Coldwell Banker Realty
(If provided) CoList: Bill Wilson from Coldwell Banker Realty
$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
$995,000
2 Beds ⋅ 3 Baths ⋅ ML82044756 MLS ⋅ Redwood Estates BLDG.
Nestled inside the Los Gatos redwoods, this beautiful ranch home of 1371sqft, features 2 bedrooms, 2.5 bathrooms, and 2 bonus rooms. The gourmet kitchen features clean, cool tones, quartz countertops, an electric Maytag range/oven and whirlpool refrigerator. The kitchen opens up to a cozy dining and warm living area. The inviting living area is accented with vaulted ceilings, and plentiful natural light streams in from the skylights and large windows. The electric fireplace anchors the room. There are two bedrooms (one is a suite) off the ground floor, and a half bathroom with laundry area. The lower floor features an open office/bonus space, a room with a large window, and the large semi-finished storage area. Hardwood floors throughout. Current upgrades include: a HVAC system with Nest thermostat, new paint, window shades and screens, and a new fence. Public water and PG&E services. Septic. The home is immaculate, and an excellent investment property with strong income potential for both long and short term (Airbnb) rentals. Excellent school district - Los Gatos Saratoga. Fifteen minute commute to downtown Los Gatos or downtown Santa Cruz. Enjoy the fresh air, immense redwood trees, and spectacular views in this peaceful woodland retreat.

18115 La Verne DR, Los Gatos

Listed by Melissa Lynch, 408-839-3580 from Galway Real Estate & Management
(If provided) CoList: from

$1,098,000
2 Beds ⋅ 3 Baths ⋅ ML82028582 MLS
Recently installed 8-panel solar system with back up battery storage and inverter, plus a 220V EV charger. This updated home delivers the perfect blend of privacy, convenience, and modern comfort just 7 minutes away from downtown Los Gatos and schools. Bright and welcoming, the two-level layout (plus an approximately 300 sq. ft. basement) is filled with natural light from large windows and skylights. The main living area features beamed ceilings that flow easily to a spacious patio, perfect for relaxing and entertaining. The remodeled kitchen offers high ceilings and a light, open feel. Upstairs, two comfortable bedrooms and two updated bathrooms provide a clean, modern retreat. Multiple terraced yards are an oasis for gardening. Gentle creek nearby creates a peaceful and inviting outdoor setting. Additional highlights include: central A/C and heating, upgraded electrical panel, two tankless water heaters, backup battery, and ample parking. Located within the highly regarded Los Gatos school district and a tight knit mountain community surrounded by majestic redwoods, offering a rare blend of serene mountain living with convenient access to town.

19060 Laurel DR, Los Gatos

Listed by Team Russ Homes, 408-502-5454 from Coldwell Banker Realty
(If provided) CoList: Ronnie Cope from Coldwell Banker Realty
$4,750,000
3 Beds ⋅ 2 Baths ⋅ ML82042918 MLS
Rare Commercial Tourism (CT) Opportunity on Highway 17 with 586' of frontage! Situated at the summit of scenic Highway 17 between Los Gatos and Santa Cruz, this versatile 2.34-acre parcel offers endless possibilities for investors and business owners. This must-see property features high-visibility highway frontage with a dedicated turn lane and is improved with a charming 3-bedroom, 2-bathroom house, a former restaurant building with a full kitchen, a 4-car garage, and three 12x14 cottages with a dedicated 8x8 bathroom facility. Benefit from massive exposure with over 40,000 vehicles passing daily, with even higher volumes on weekends and holidays. Offering unlimited business potential for a boutique lodge, destination eatery, retail shop, or service-oriented venture. Bring your vision to this iconic Santa Cruz Mountains site! Buyer to verify all intended uses, sizes, permits, statues/legality of all existing structures and zoning requirements with the Santa Cruz County Planning Department.

22990 Santa Cruz Highway 17, Los Gatos

Listed by Paul Oh, 669-888-4967 from New Star Realty Silicon Valley
(If provided) CoList: from

$2,150,000
2 Beds ⋅ 1 Baths ⋅ ML82033907 MLS
Perched above Montevina Road in the Los Gatos Mountains, this 15-acre gated estate offers privacy, scale, and panoramic views of the Bay Area, Lexington Reservoir, and Lyndon Canyon, just minutes from downtown Los Gatos. A paved road leads to a gated entrance, creating a private mountain retreat with dramatic sunrises and sunsets. The property includes an approximately 3 acre fenced area suitable for vineyard use, along with an additional 3 acres across the road offering potential for a second residence or expanded vineyard acreage. A high producing well is complemented by two 10,000 gallon storage tanks and an on site fire hydrant. The home features stone mosaic wall cladding, knotty pine cabinetry, solid core doors, hardwood floors, and a temperature controlled wine cellar finished in stone. The kitchen offers a stone island with seating, a chef quality six burner Jade range, and a Thermador oven. Two versatile outbuildings provide laundry and storage. Located within the Los Gatos School District, this is a rare opportunity to own a private, view-driven estate with close proximity to town!

19375 Montevina RD, Los Gatos

Listed by Ashley Melikian, 831-419-6685 from eXp Realty of California Inc
(If provided) CoList: from

$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

$798,000
1 Beds ⋅ 1 Baths ⋅ ML82034137 MLS
This property is part of the Kennedy Estate. A rare 26.8-acres Los Gatos mountain property featuring a natural spring, mature trees, and exceptional privacy. This property includes an older home situated within a serene, wooded setting, offering a unique opportunity for those seeking substantial acreage and a natural water source. Buyers should verify zoning, access, utilities, square footage, septic, water rights, and all permitted uses with Santa Clara County. A peaceful retreat ideal for those looking to secure significant land in a desirable mountain location.

24733 Loma Prieta AVE, Los Gatos

Listed by Gregg Fussell, 408-857-0957 from Coldwell Banker Realty
(If provided) CoList: Bill Wilson from Coldwell Banker Realty
$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

$1,449,000
3 Beds ⋅ 3 Baths ⋅ ML82032455 MLS
Impressive Aldercroft Heights view property, only 10 minutes/6 miles from downtown Los Gatos! Featuring a spacious living room with beamed ceiling, woodburning fireplace, and multiple picture windows framing stunning mountain views... flooding the home with natural light. Gleaming hardwood floors throughout the open concept, upper-level living areas. Formal dining area with vaulted ceiling, bay window. Beautiful kitchen features granite countertops & stainless appliances, vaulted ceiling with skylights. Separate family room/den, or study, with slider to brick patio. Potential 4th bedroom - includes built-in closet and ensuite full bath. Gorgeous primary suite with hardwood flooring, double sliders open to expansive front deck with mountain views. Oversize jetted tub, stall shower and double vanity. Two further bedrooms on lower level, & 3rd full bath. Large recessed laundry area with sink, offers potential for 2nd kitchen. Wine cellar! 3 levels of spacious decking for entertaining or basking in the sun. Enjoy panoramic mountain views from every part of the property! Large walk-in basement, tons of storage areas. 1 car garage and ample driveway parking. Incredible value for a large 1990 quality-built home in the coveted Los Gatos school district - just a few minutes from LGHS!

21386 Sunnyside 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

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