Los Gatos Homes with Hills View

Welcome to Los Gatos, California – a picturesque town nestled in the foothills of the Santa Cruz Mountains. Known for its charming downtown, vibrant arts scene, and stunning natural beauty, Los Gatos offers a unique blend of suburban tranquility and urban sophistication. With its tree-lined streets, boutique shops, and an array of gourmet dining options, this community has something for everyone.

One of the most alluring features of Los Gatos is its breathtaking homes with hill views. Imagine waking up to the serene sight of rolling hills bathed in golden sunlight, or enjoying a glass of wine on your patio as the sun sets over the stunning landscape. These properties not only provide a sense of privacy and seclusion but also allow residents to immerse themselves in the beauty of California’s natural environment.

Los Gatos is also home to some of the best schools in the state, making it an ideal location for families seeking a nurturing community. Outdoor enthusiasts will love the nearby hiking trails, parks, and the picturesque Los Gatos Creek, which offers opportunities for biking, jogging, and leisurely strolls.

Whether you’re looking for a cozy cottage or a luxurious estate, Los Gatos’ homes with hill views promise a lifestyle filled with comfort, elegance, and breathtaking scenery. Come discover the charm of this enchanting town, where every day feels like a retreat in the hills. Your dream home awaits!

Newest Los Gatos Homes with Hills View

$3,958,000

5 Beds ⋅ 3 Baths ⋅ ML82064885 MLS

Discover the charm of this beautifully designed 5-bedroom, 3-bath home in the sought-after Worcester Park area of Los Gatos. Thoughtfully arranged with a desirable reverse floor plan, the home offers two bedrooms on the main level, and a full bath, while the upper level features three additional bedrooms including a private primary suite along with a family room, gourmet kitchen, and stunning living room showcasing beautiful hill views. Enjoy the best of indoor-outdoor living with a charming backyard featuring enchanting pathways and inviting spaces for relaxing and entertaining. As an added bonus, this home is next to the Worcester Park for the outdoor lifestyle. Modern amenities include paid solar and Tesla Powerwall batteries for added energy efficiency and peace of mind. This home is absolutely charming. Located within the award-winning Los Gatos school district, next to Worcester Park, close to the vibrant downtown. This special home offers a wonderful blend of comfort, character, views, and modern convenience.

133 Worcester LOOP, Los Gatos

Listed by Sue Nystrom-Walsh, 408-482-9343 from Compass
(If provided) CoList: from

$5,500,000

5 Beds ⋅ 3 Baths ⋅ ML82065795 MLS

Set within the prestigious Glen Una enclave of Saratoga, 15500 Glen Una presents an extraordinarily rare & visionary opportunity on approximately .56 of a flat pristine acre. This is truly an exceptional living or building opportunity for one of Silicon Valley's most iconic legendary estates. Possible potential for a subdivision into two remarkable parcels of equal distinction. Currently enhanced w/ a charming Victorian residence, or this crown jewel property invites the most discerning buyer to create a world-class architectural masterpiece tailored to an uncompromising lifestyle, where scale, privacy, and design excellence converge. Surrounded by majestic oak trees, this setting evokes a serene, park-like sanctuary with capturing luxury estate views of the nearby neighbors. The expansive grounds offer extraordinary flexibility to create a gated compound with ample space for a grand main residence, guest house, pool and spa pavilions, discreetly tucked garages, and curated gardens that blend natural beauty with refined landscaping. Surrounded by majestic valley oak trees, the site offers panoramic mountain views for architectural brilliance. The range of possibilities on this estate is limitless. Build a luxury masterpiece on this legacy estate or completely remodel this estate.

15550 Glen Una DR, Los Gatos

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

$4,998,000

5 Beds ⋅ 6 Baths ⋅ ML82065789 MLS

Warm minimalism meets sculptural design in this 2026 ground-up new construction by Redefine, located in Los Gatos' Blossom Manor neighborhood. Offering 4,258 SQFT of combined living space, the property includes a 3,525 SQFT main residence with 4 bedrooms and 4.5 baths, plus a separate 733 SQFT, 1-bedroom, 1-bath ADU. Floor-to-ceiling windows fill the expansive great room with natural light. The kitchen features paneled appliances, a 48" induction range, 30" refrigerator and freezer columns, two dishwashers and a walk-in prep pantry. A Venetian plaster spiral staircase with a curved white oak handrail and integrated lighting creates a striking centerpiece. Limestone exterior veneer, trimless doors, baseboard-free walls, white oak veneer closets and brass, alabaster and marble lighting bring warmth and refinement throughout. Smart features include hardwired Ubiquiti Wi-Fi and cameras, Sonos, hardwired window coverings, Nest thermostats, smart locks and owned solar. Served by Alta Vista Elementary, Union Middle and Leigh High School, all rated 10/10. Easy access to Highways 85 and 17 connects you to Silicon Valley tech campuses, with Los Gatos shopping, dining and recreation close to home.

15750 Loma Vista AVE, Los Gatos

Listed by Christina Khosrowabadi, 408-318-4863 from Christie's International Real Estate Sereno
(If provided) CoList: from

$785,000

ML82064017 MLS

Enjoy sweeping top of the world views of Monterey Bay and Santa Cruz as you drive into the serene Ocean View neighborhood consisting of estate homes, leading to a tranquil setting framed by majestic oak trees. Skip the years of red tape and the endless cycle of county reviews. This is your rare opportunity to move past the grueling planning process and straight toward building your dream home. Shovel-ready and sitting on approximately 2.5 acres, this property offers a combination of privacy, natural beauty, and development readiness that is nearly impossible to find. Much of the many year pre-construction work is already behind you. Permits have been issued for a 2,330-square-foot residence and an 819-square-foot garage. Geological and soils testing are finished, and grading plans are fully approved and in place. A well is already installed, and power is available at the street, providing a massive head start on the infrastructure needed to bring your vision to life. Served by highly regarded local schools, including Loma Prieta Elementary, C.T. English Middle, and Los Gatos High. You're just a minute from the Skyland Mountain Church and five minutes from the Summit Center Market. Only 20 minutes from the beach or the vibrant shops and dining of downtown Los Gatos.

Ocean View RD, Los Gatos

Listed by Keith Kanady, 408-316-1666 from Compass
(If provided) CoList: from

$3,998,000

5 Beds ⋅ 3 Baths ⋅ ML82064697 MLS

Tucked away on a quiet, non-through court that most Los Gatos residents have yet to discover. Room for everyone! 3,300 sq ft on a 10,000 sq ft lot. Short walk to Van Meter, Fisher Middle and Los Gatos High. The backyard is the headline. A covered premium outdoor kitchen fully outfitted with Lynx grill, griddle, warming drawer, sink, fridge, storage, all set in Macaubas Quartzite and stacked stone plus gorgeous matching outdoor gas fireplace, stunning solar-heated pool w/water features cascading from a raised stone ledge and an automatic safety cover. Set in pavers with curated mature landscaping - this is the backyard everyone will want to be at. Inside is a sun-filled kitchen with a breakfast nook, wall pantry, wine fridge. Adjacent is formal dining with wainscoting and the living room with fireplace. The large family room is the space for gathering! Additionally, a large home office at the front entry completes the main level. Four bedrooms upstairs, plus a fifth recorded bedroom currently set up as an oversized laundry room. The detached 2-car garage features epoxy floors + storage, the long driveway accommodates many cars. Minutes to downtown Los Gatos, Hwy 17 & 85, excellent commuter access to Apple, Netflix, Meta, Google, Nvidia, MSFT, and short drive to Santa Cruz beaches.

100 Calfhill CT, Los Gatos

Listed by Tracy Pina, 408-460-0861 from Coldwell Banker Realty
(If provided) CoList: from

$2,650,000

4 Beds ⋅ 5 Baths ⋅ ML82064954 MLS

Elegant mountain home situated in the desirable 'Summit Woods', close to the heart of the Summit community and local amenities including the Summit Store, wineries, churches, Loma Prieta elementary & CT English middle schools. Approx 20 mins to downtown Los Gatos & Los Gatos High, or Capitola & the beach! Over 5000 sqft luxurious living space, set on 1.26 acres sunny, all usable land...ample space to add a pool, sports court, vineyard...even horses. The ground floor comprises a formal entry & parlor, chefs ktichen with island and informal dining, living room with vaulted ceilings & rock fireplace. Huge formal dining room features walk-in wine cellar with wrought iron gate. Expansive master suite with spa-like bathroom. Laundry room leads to attached SIX CAR garages with marble tile floors! On the 2nd floor; 3 further bedrooms incl. 2 ensuite baths, hall bath and family room/den, large balcony with mountain views. The property exterior features a gated entry with paver driveway, perimeter fencing, rear deck with views over the raised gardens & gently sloped land. Huge enclosed dog run, custom chicken coop, garden tractor garage, and whole house generator. Summit Woods annually welcomes the mountain community for Halloween trick-or-treating. Beloved family friendly neighborhood!

24010 Summit Woods DR, 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

$3,000,000

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

$7,100,000

4 Beds ⋅ 5 Baths ⋅ ML82061272 MLS

With million dollar views looking out of practically every window on the North side, on this prestigious Matilija drive, it can be a little lonely on the top, but it feels extremely comfortable. Wake up to abundant morning sun allowed in through the enormous windows next to the soaring ceilings. This magnificent North facing home is surrounded by multi-million dollar homes down the road. And although this mansion is zoned for Saratoga schools, those who prefer to send their kids to Harker find it a breeze to drive there. The current owners raised their very successful children in this lucky house, and became very successful! They moved to the most prestigious neighborhood in the Bay Area. So come get the good karma! 7.03 acres of lot presents the potential to do SB9 lot splits. Buyer to investigate. $150K spent to get an ADU approved, near the entrance, pending retaining wall reviews. Enormous 1st level has primary + 2nd bedroom ensuites, and office on the first floor, giving you the expansive feel. Soaring 12' high ceiling in the living room, with 20' ceiling in the round stair case leading to 2 more ensuites on the 2nd floor! Private backyard and swimming pool. Mountains on the back & right side provide sense of protection. Solar w/ Powerwall is fully owned. Live your dream now

16421 Matilija DR, Los Gatos

Listed by Charles Liu, 650-999-3888 from Compass
(If provided) CoList: from

$1,575,000

3 Beds ⋅ 2 Baths ⋅ ML82063639 MLS

Perched in the celebrated Skyland community of Los Gatos, 24766 Skyland Road is a rare find that captures the essence of a modern rural lifestyle on nearly three sprawling acres. At the heart of the property sits a modern 14-year-old main residence with breathtaking views that stretch across the valley to the Loma Prieta Ridge. The private outdoor oasis, where the grounds have lots of usable land features persimmons, berries, lemons, apples, pears, and plums; a true gardener's dream. The property's heritage as part of a historic ranch is reflected in its versatile structures. An oversized rustic shop provides parking for two vehicles plus a generous amount of space for projects, or additional covered storage. Two additional structures include the original ranch house, which now serves as a functional ADU, and a separate accessory structure which was previously utilized as a living unit. Parking for many vehicles. Significant recent investment has been poured into the grounds and the secondary structures. For those looking to embrace the equestrian or outdoor lifestyle, the partial stables offer a unique head start. This is a property that offers both the quiet beauty of the mountains and the modern infrastructure and flexibility to support a busy, creative lifestyle.

24766 Skyland RD, Los Gatos

Listed by Keith Kanady, 408-316-1666 from Compass
(If provided) CoList: from

$1,699,000

2 Beds ⋅ 2 Baths ⋅ ML82061111 MLS

Rare opportunity just moments from Downtown Los Gatos! Charming Craftsman-style cottage built brand new in 1999, offering 2 bed, 2 baths in one of Los Gatos most desirable tree-lined neighborhoods. Bright and airy with 9-foot ceilings, large windows, hardwood floors, crown molding, and exceptional quality throughout. Beautiful custom kitchen with custom cabinetry, granite, marble, limestone, and stainless-steel appliances. French doors leading to brick patio for outdoor dining. Central A/C, attached garage with opener, and fantastic curb appeal. Dropdown attic ladder in garage with standing room storage area. Ideally located near downtown, shopping, dining, and award-winning Los Gatos schools.

27 Cross WAY, Los Gatos

Listed by Peter Myers, 408-605-0428 from Coldwell Banker Realty
(If provided) CoList: from

$3,750,000

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

$2,288,000

4 Beds ⋅ 2 Baths ⋅ ML82061470 MLS

Welcome to this charming single-level home where comfort, character, and an incredible location come together. Offering 4 beds, 2 bathrooms, this light-filled home combines inviting indoor spaces with beautiful mountain views. Kitchen: garden window views of the surrounding mountains, stainless steel appliances: micro, fridge, stove/range, newer flooring throughout much of the home, dual-pane windows, a freestanding fireplace. Updated primary bathroom offers a fresh, modern touch. Inviting side deck, imagine starting your mornings with coffee, relaxing in the spa after a long day, enjoying dinner under the stars. The backyard offers additional space and exciting potential for creating your own outdoor retreat or future improvements. Buyer to verify all building possibilities/capabilities with appropriate authorities. Covered carport, abundance of storage beneath the home. Enjoy easy access to great LG schools, coffee shops, stores, medical facilities, dining, freeway, and downtown amenities. Beyond the doorstep, explore nearby trails, head up the road to TestaRossa Winery. With its single-level floor plan, mountain views, natural light, this home offers a rare opportunity to enjoy comfort, convenience, and the quintessential LG lifestyle including those beloved holiday parades!

200 Jackson ST, Los Gatos

Listed by Susan LaRagione, 408-242-5901 from Sync Brokerage Inc
(If provided) CoList: from

Start Your Search

The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than Bailey Properties are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Los Gatos Homes with Hills View

Newest Los Gatos Homes with Hills View

How much is your home worth?

How much is your home worth?