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A rare combination of single-story living, usable flat land, and a private pool awaits in the Los Gatos Mountains. Set on approximately 3.5 acres, this gated estate offers exceptional privacy, scenic mountain views, and resort-style living. Beautifully refreshed with new interior and exterior paint, new flooring, updated cabinetry, fresh landscaping and sod, and a brand-new 50-year Presidential roof, the home offers move-in-ready comfort in an extraordinary setting. Expansive picture windows showcase the surrounding landscape, while a spacious kitchen and entertainment room with wet bar create inviting spaces to gather. Outdoors, enjoy a cascading waterfall, tranquil pond, swimming pool, spa, and outdoor kitchen surrounded by mature landscaping. Two dedicated offices and a separate gym provide incredible flexibility for work, wellness, and everyday living. Additional highlights include owned solar, a backup generator, and a three-car garage. Experience the peaceful mountain lifestyle, where nature and wildlife are part of everyday life, all within reach of downtown Los Gatos, Silicon Valley, and the beaches of Santa Cruz.

4 Beds ⋅ 4 Baths ⋅ ML82006582 MLS

A rare combination of single-story living, usable flat land, and a private pool awaits in the Los Gatos Mountains. Set on approximately 3.5 acres, this gated estate offers exceptional privacy, scenic mountain views, and resort-style living. Beautifully refreshed with new interior and exterior paint, new flooring, updated cabinetry, fresh landscaping and sod, and a brand-new 50-year Presidential roof, the home offers move-in-ready comfort in an extraordinary setting. Expansive picture windows showcase the surrounding landscape, while a spacious kitchen and entertainment room with wet bar create inviting spaces to gather. Outdoors, enjoy a cascading waterfall, tranquil pond, swimming pool, spa, and outdoor kitchen surrounded by mature landscaping. Two dedicated offices and a separate gym provide incredible flexibility for work, wellness, and everyday living. Additional highlights include owned solar, a backup generator, and a three-car garage. Experience the peaceful mountain lifestyle, where nature and wildlife are part of everyday life, all within reach of downtown Los Gatos, Silicon Valley, and the beaches of Santa Cruz.

19050 Skyline BLVD, Los Gatos

Listed by Skylight Homes, 408-665-7309 from Skylight Homes
(If provided) CoList: from

$3,750,000

Surrounded by nature's beauty, 17575 Mountain Charlie Road offers a rare opportunity to experience peaceful mountain living while only seven minutes from Downtown Los Gatos. Privately nestled among towering redwoods, this exceptional 3,146 sq.ft. with flexible 297 sq.ft. studio/ADU potential, blends natural beauty and modern convenience. Designed to embrace its breathtaking surroundings, the home showcases dramatic 20 ft vaulted ceilings and windows that fill this home with natural light and spectacular mountain views, creating an inviting atmosphere for indoor, outdoor living and entertaining. The home features four bedrooms, three full bathrooms and one an a half bath, including a desirable ground-floor primary suite with a spacious walk-in closet. The kitchen includes a center island with ample cabinets space, multiple dining spaces and separate family room and formal room. Additional highlights; hardwood and carpet flooring, two fireplaces, indoor laundry room, built-in vacuum system, and an attached 3 car garage. Step outside to enjoy a pergola, in-ground pool, spa, garden beds, fruit trees, and berries. Tesla power wall, a private water well, and onsite CAL FIRE hydrant complete this extraordinary property, offering the perfect balance of privacy, comfort, and convenience.

4 Beds ⋅ 4 Baths ⋅ ML82055182 MLS

Surrounded by nature's beauty, 17575 Mountain Charlie Road offers a rare opportunity to experience peaceful mountain living while only seven minutes from Downtown Los Gatos. Privately nestled among towering redwoods, this exceptional 3,146 sq.ft. with flexible 297 sq.ft. studio/ADU potential, blends natural beauty and modern convenience. Designed to embrace its breathtaking surroundings, the home showcases dramatic 20 ft vaulted ceilings and windows that fill this home with natural light and spectacular mountain views, creating an inviting atmosphere for indoor, outdoor living and entertaining. The home features four bedrooms, three full bathrooms and one an a half bath, including a desirable ground-floor primary suite with a spacious walk-in closet. The kitchen includes a center island with ample cabinets space, multiple dining spaces and separate family room and formal room. Additional highlights; hardwood and carpet flooring, two fireplaces, indoor laundry room, built-in vacuum system, and an attached 3 car garage. Step outside to enjoy a pergola, in-ground pool, spa, garden beds, fruit trees, and berries. Tesla power wall, a private water well, and onsite CAL FIRE hydrant complete this extraordinary property, offering the perfect balance of privacy, comfort, and convenience.

17575 Mountain Charlie RD, Los Gatos

Listed by Anita Salas, 408-310-3918 from The Agency
(If provided) CoList: from

$1,788,888

Welcome to one of the finest homes in Redwood Estates, a rare opportunity to own a beautiful retreat offering exceptional privacy. One of very few homes near the very top of the Santa Cruz mountains, the home offers a ridgetop setting with layered Santa Cruz Mountain views from the bedrooms. Wake to distant ridgelines above the redwood canopy. It is easily accessed with a 2 minute travel time from Hwy 17 and only 15 minutes to downtown Los Gatos and 20 minutes to downtown Santa Cruz. One of the property's most distinctive features is its extraordinary collection of Japanese maples. More than 25 trees representing over 15 different varieties create a living garden that changes character throughout the year, from delicate spring greens to brilliant autumn color. The landscape feels curated yet natural, blending seamlessly with the surrounding mountain setting. The home also features a full 132" projection screen in a 20 foot high slanted ceiling room.

3 Beds ⋅ 3 Baths ⋅ CRFR26194826 MLS

Welcome to one of the finest homes in Redwood Estates, a rare opportunity to own a beautiful retreat offering exceptional privacy. One of very few homes near the very top of the Santa Cruz mountains, the home offers a ridgetop setting with layered Santa Cruz Mountain views from the bedrooms. Wake to distant ridgelines above the redwood canopy. It is easily accessed with a 2 minute travel time from Hwy 17 and only 15 minutes to downtown Los Gatos and 20 minutes to downtown Santa Cruz. One of the property's most distinctive features is its extraordinary collection of Japanese maples. More than 25 trees representing over 15 different varieties create a living garden that changes character throughout the year, from delicate spring greens to brilliant autumn color. The landscape feels curated yet natural, blending seamlessly with the surrounding mountain setting. The home also features a full 132" projection screen in a 20 foot high slanted ceiling room.

21670 Woolaroc DR, Los Gatos

Listed by Brian Dombroski, 559-477-4332 from Dombroski Realty
(If provided) CoList: from

$1,800,000

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!

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

$919,000

Charming Los Gatos redwood retreat blending mountain cabin vibes with modern updates! Meticulously maintained and largely rebuilt in the early 1990s (architectural plans available), this move-in ready home features fresh interior paint, refinished wood floors, and new tile work. The 1,128 sq ft main level includes 2 bedrooms, a large tiled bath, formal dining, family room, flex space that could be used as a 3rd bed or office, and a hallway-free layout that feels extra spacious. The kitchen boasts green marble, pine accents, new flooring , gas cooktop, and stainless appliances. Downstairs offers a 385 sq ft finished basement with laundry, workshop, and extensive built-in storage. Enjoy central forced air, a wood stove with winter wood included, a 2019 roof, and a Tesla EV charger. Outside features an 850 sq ft sunny deck, private patio, and terraced yard framed by robust wired caged retaining walls. Located in a top school district, 14 mins to the high school. Low $218/mo fee covers water, roads, and community amenities.

2 Beds ⋅ 1 Baths ⋅ ML82050444 MLS ⋅ Chemeketa Park BLDG.

Charming Los Gatos redwood retreat blending mountain cabin vibes with modern updates! Meticulously maintained and largely rebuilt in the early 1990s (architectural plans available), this move-in ready home features fresh interior paint, refinished wood floors, and new tile work. The 1,128 sq ft main level includes 2 bedrooms, a large tiled bath, formal dining, family room, flex space that could be used as a 3rd bed or office, and a hallway-free layout that feels extra spacious. The kitchen boasts green marble, pine accents, new flooring , gas cooktop, and stainless appliances. Downstairs offers a 385 sq ft finished basement with laundry, workshop, and extensive built-in storage. Enjoy central forced air, a wood stove with winter wood included, a 2019 roof, and a Tesla EV charger. Outside features an 850 sq ft sunny deck, private patio, and terraced yard framed by robust wired caged retaining walls. Located in a top school district, 14 mins to the high school. Low $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

$2,475,000

Build your dream estate on the last remaining waterfront properties feat. 6.55 acres with orivacy, direct access to nature, and exceptional convenience less than five minutes from downtown Los Gatos. Preliminary designs for a 13,252 SF estate by Kohlsaat & Associates establishes the vision, with four levels of lake-facing living, covered verandas, wellness suite, theater, golf simulator, catering kitchen, wine room, elevator, four-car garage, and extensive indoor-outdoor entertaining areas. Yet the design is only one expression of what may be possible. County jurisdiction offers meaningful flexibility for buyers seeking greater scale, massing, height, square footage, and additional buildings. Envision a private family compound, secure technology-enabled retreat, underground safe rooms, guest residences, collector garages, recreation facilities, formal gardens, orchards, or a secluded wellness estate. Dual driveway access, a private well, and public water availability add flexibility. Acquire the land and plans, customize the program with Massei Construction, or contract for the completed estate. More than a homesite, this is a rare platform for a one-of-a-kind Silicon Valley legacy property.

ML82054897 MLS

Build your dream estate on the last remaining waterfront properties feat. 6.55 acres with orivacy, direct access to nature, and exceptional convenience less than five minutes from downtown Los Gatos. Preliminary designs for a 13,252 SF estate by Kohlsaat & Associates establishes the vision, with four levels of lake-facing living, covered verandas, wellness suite, theater, golf simulator, catering kitchen, wine room, elevator, four-car garage, and extensive indoor-outdoor entertaining areas. Yet the design is only one expression of what may be possible. County jurisdiction offers meaningful flexibility for buyers seeking greater scale, massing, height, square footage, and additional buildings. Envision a private family compound, secure technology-enabled retreat, underground safe rooms, guest residences, collector garages, recreation facilities, formal gardens, orchards, or a secluded wellness estate. Dual driveway access, a private well, and public water availability add flexibility. Acquire the land and plans, customize the program with Massei Construction, or contract for the completed estate. More than a homesite, this is a rare platform for a one-of-a-kind Silicon Valley legacy property.

00-1 Old Santa Cruz Highway, Los Gatos

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