Los Gatos/Monte Sereno Homes with Hills View

Nestled in the heart of Santa Clara County, Los Gatos and Monte Sereno are two enchanting communities that offer an idyllic blend of suburban charm and natural beauty. Known for their picturesque landscapes and vibrant local culture, these neighborhoods are perfect for those seeking a serene yet sophisticated lifestyle.

Los Gatos boasts a delightful downtown area filled with boutique shops, gourmet restaurants, and art galleries, all framed by the stunning backdrop of the Santa Cruz Mountains. Residents enjoy a tight-knit community atmosphere, with numerous events throughout the year, including the popular Los Gatos Music in the Park series and the annual Los Gatos Art and Wine Festival. The town is also home to top-rated schools, making it an attractive choice for families.

Just a stone's throw away, Monte Sereno offers a more tranquil setting, characterized by its spacious lots and luxurious homes, many of which boast breathtaking views of the surrounding hills. This exclusive enclave is known for its privacy and serenity, with lush landscaping and scenic trails that encourage outdoor exploration. Whether you’re hiking through the nearby parks or enjoying a quiet evening on your patio, the natural beauty of Monte Sereno is truly captivating.

For those seeking homes with hill views, both Los Gatos and Monte Sereno deliver stunning properties that seamlessly blend comfort and elegance. Imagine waking up to the gentle hues of sunrise over the hills or unwinding in the evening with panoramic vistas that stretch as far as the eye can see. Here, every day feels like a retreat, and the beauty of the landscape becomes a cherished part of your everyday life. Discover the perfect home in this enchanting area, where the hills are not just a backdrop, but a way of life.

Newest Los Gatos/Monte Sereno Homes with Hills View

$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

$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

$2,198,000

3 Beds ⋅ 2 Baths ⋅ ML82062990 MLS ⋅ Live Oak Manor BLDG.

Stunning, beautifully updated single-story ranch in prime Live Oak Manor with award-winning Los Gatos schools. Offering 3 bedrooms, 2 baths, and approx. 1,296 sq ft, this home pairs classic charm with fresh paint inside and out, new LVT flooring, dual-pane windows, and new recessed and accent lighting. A two-tone exterior, lush front lawn, and landscaped borders create inviting curb appeal. The living room features a fireplace with a tiled mantel and sliding glass doors to the backyard. The updated kitchen showcases Kashmir quartz counters, freshly painted cabinetry, new hardware, generous storage, and a bar-top peninsula. Appliances include a stainless steel gas downdraft cooktop, built-in oven and microwave, and stainless steel dishwasher. Refreshed baths include an updated guest vanity and tub/shower, plus a primary bath with new vanity, mirror, designer lighting, and glass-enclosed shower. Enjoy the interlocking brick patio, new lawn, heritage oak, and mature greenery. Attached two-car garage with refreshed floor finish. Near Live Oak Manor Park, Whole Foods, Trader Joe's, shopping and dining, Vasona Lake County Park, Oak Meadow Park, Los Gatos Creek Trail, and downtown Los Gatos. Award-winning LG schools: Blossom Hill Elementary, Fisher Middle, and Los Gatos High.

117 Hollycrest DR, Los Gatos

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

$2,498,000

ML82062720 MLS

In the highly sought after Monte Sereno neighborhood of multi million dollar estates and located in the Saratoga school district, sits this beautiful, .58 acre newly formed parcel. This property offers beautiful vistas of the surrounding mountains. Discussions between the Civil Engineer and the City of Monte Sereno determined a Floor Area Ratio (FAR) maximum of 4,400sf of living area, not including the garage. Buyers to confirm this information with the City of Monte Sereno. Seller wishes to close escrow in year 2027. Topo and Survey available. Utilities are available at the street.

16099 Greenwood RD, Monte Sereno

Listed by Nevis and Ardizzone, 408-891-8149 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

$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

$5,488,000

4 Beds ⋅ 5 Baths ⋅ ML82060376 MLS

Enjoy a beautiful contemporary Mediterranean-style estate, conveniently located just off Shannon Road, minutes from schools, parks and town. This private enclave offers remarkable privacy, sweeping surround mountain views, and a strong connection to the outdoors. Refined interiors feature travertine and engineered hardwood floors, carved limestone fireplaces, alder cabinetry & chef's kitchen with professional-grade appliances, prep sink, wine refrigerator, walk-in pantry and large island. The main level includes an executive office or 5th bedroom, en-suite guest bedroom, mudroom and attached two-car garage with Level 2 EV charging. Upstairs, the primary suite features a vaulted open-beam ceiling, fireplace, walk-in closet, private balcony, plus two additional en-suite bedrooms, a bonus room with wet bar, wine closet and laundry. Landscaped grounds include a central courtyard, covered entertaining area with fireplace and heaters, outdoor kitchen, greenhouse, garden swing and mature oaks. Smart-home technology, multi-zone HVAC, dual tankless water heaters, water softening, leak detection, and 10,000 gallons of on-site water storage complete the home. This luxurious hillside retreat brings together remarkable privacy with a balance of serenity, convenience and exceptional lifestyle.

15730 Shannon Heights RD, 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

$2,998,000

3 Beds ⋅ 2 Baths ⋅ ML82058028 MLS

ENCHANTING UPDATED HOME BY DOWNTOWN | Built in 1923, this home seamlessly blends the charm of years past with today's modern conveniences. Located within blocks of Santa Cruz Avenue, this Almond Grove residence affords coveted access to downtown shopping and dining without compromising privacy and tranquility. Period details like picture railing and ceiling treatments add authenticity, while an array of new upgrades, including new flooring, roofing, and full interior renovation lends modern style and convenience. The pristine remodeled kitchen is nestled at the heart of the layout, and the large primary suite is private with an elegant bath and backyard access. Extra storage on basement level. Flat and spacious, the grounds offer a formal entry garden, gated drive with plenty of off-street parking, newly landscaped backyard, and plenty of space for play, private relaxation, and future expansion. The detached two-car garage comes complete with HVAC and provides potential for an ADU with private yard. Enjoy excellent proximity to downtown destinations, Bachman Park, Vasona Lake, and excellent Los Gatos schools such as Daves Avenue Elementary, Fisher Middle, and Los Gatos High (buyer to verify).

320 Bachman AVE, Los Gatos

Listed by Stefan Walker, 408-209-6100 from KW Bay Area Estates
(If provided) CoList: from

$1,799,000

2 Beds ⋅ 2 Baths ⋅ ML82056341 MLS

Absolutely darling home minutes up Overlook Road and a short walk to downtown Los Gatos. Enjoy direct access to Aquinas Trailhead at the end of the road with miles of trails for walking and riding. This lovingly updated home features a remodeled kitchen with cherry cabinets, granite counters, stainless steel appliances, double oven, microwave and dishwasher. There are two renewed bathrooms with stone and tile surfaces, high ceilings, double pane windows and french door, newer retaining walls and refreshed landscaping including lemon, lime, plum, peach, and passion fruit trees. Hickory hardwood floors throughout. Two spacious bedrooms with built-in closet organizers offer beautiful and far reaching views. Recent upgrades include a new heating and air-conditioning system, new ducts, and fresh interior and exterior paint. Entertain on the large viewing deck or relax in the expansive backyard with mature landscaping & enclosed pergola and Trex decking& landscape lighting. A large two car garage with storage, plus extra parking provide convenience for guests. Served by award winning Los Gatos schools, Daves Ave Elementary, Raymond J Fisher Middle & Los Gatos High School. This charming home offers incredible sweeping views of the valley, mountain and city lights visible for miles

16900 Sheldon RD, Los Gatos

Listed by William Lister, 408-892-9300 from Coldwell Banker Realty
(If provided) CoList: from

$2,600,000

3 Beds ⋅ 2 Baths ⋅ ML82057196 MLS

Wonderful downtown Los Gatos location in the popular Loma Alta/Johnson neighborhood! This beautiful, almost 1/3-acre parcel features an existing historic home on a spacious lot just steps away from top Los Gatos schools, shops and dining. The expansive, open floor plan enjoys large picture windows overlooking the front as well as the tree studded ravine at the rear of the property. Update and expand while maintaining the historic nature of the exterior front facade. A unique opportunity to own a piece of history in a very desirable location in downtown Los Gatos!

110 Johnson AVE, Los Gatos

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

$4,300,000

4 Beds ⋅ 4 Baths ⋅ ML82053472 MLS

This spacious 4-bedroom, 3.5-bathroom home in Los Gatos offers 2,686 sq. ft. of living space with a combination of hardwood and tile flooring throughout. The kitchen is equipped with modern amenities including a built-in dishwasher, microwave, refrigerator, garbage disposal, tile countertops, and a 220-volt outlet. Enjoy cozy evenings by the gas-burning and wood-burning fireplaces in the living areas. The home features a separate family room and a dining area, as well as an open, inverted floor plan with vaulted and open beam ceilings, skylights, and a garden window. Laundry facilities include washer/dryer hookups with both 110V and 220V electricity in the utility room. Additional amenities include built-in vacuum, wet bar, and a security gate. The property sits on a large lot of over 123,000 sq. ft. with a fenced, in-ground pool. Cooling is provided by ceiling fans, central AC, and multi-zone systems. The residence is located within the Los Gatos Union Elementary school district. Two-car garage included.

15295 Kennedy RD, Los Gatos

Listed by Lawrence Hernandez, 408-315-1200 from Realty One Group Infinity
(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

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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 Legacy Real Estate Inc 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/Monte Sereno Homes with Hills View

Newest Los Gatos/Monte Sereno Homes with Hills View

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