Los Gatos Homes with Vineyard View

Nestled in the heart of California’s Silicon Valley, Los Gatos is a picturesque town that seamlessly blends natural beauty with a vibrant community spirit. Known for its charming downtown area, tree-lined streets, and stunning vistas, Los Gatos offers a unique lifestyle that attracts families, professionals, and retirees alike. With its rich history dating back to the 1800s, the town boasts a delightful mix of historic architecture and modern amenities, making it a desirable place to call home.

One of the most enchanting features of Los Gatos is its proximity to breathtaking vineyards that dot the surrounding hillsides. Imagine waking up each morning to the sight of rolling vineyards, their lush grapevines stretching out as far as the eye can see. Homes with vineyard views in Los Gatos provide a serene backdrop that enhances the beauty of everyday life. These properties often feature expansive outdoor spaces, perfect for entertaining or simply enjoying a glass of local wine while taking in the stunning sunset over the vineyards.

In addition to its scenic landscapes, Los Gatos is known for its exceptional schools, thriving arts scene, and numerous parks and recreational opportunities. The town hosts a variety of events throughout the year, from farmers’ markets to art walks, fostering a strong sense of community among its residents. With its idyllic setting and vibrant lifestyle, Los Gatos is not just a place to live; it’s a place to thrive. Discover your dream home with vineyard views in this charming town and experience the best of California living!

Newest Los Gatos Homes with Vineyard View

$3,400,000

5 Beds ⋅ 3 Baths ⋅ ML82058469 MLS

Perched on the crest of the Santa Cruz Mountains, 26765 Havenhill Lane offers a rare combination of luxury living, privacy, space, and the natural beauty of the mountains. Sweeping mountain and Monterey Bay views, neighboring vineyards, and spectacular sunsets create a setting intimately connected to the landscape. Set on just over an acre, the Mediterranean-inspired home is designed for entertaining, everyday comfort, and seamless indoor-outdoor living. A gourmet kitchen, wine room, indoor sports court, and media/game room offer spaces to gather, unwind, and have fun. Outside, an infinity-edge pool and spa, outdoor kitchen, fire pit, covered terraces, and landscaped grounds create a true resort-like experience. A detached workshop, garden, and chicken coop offer space to create, grow, and connect with the land. Starlink, Ubiquiti networking, owned solar, a commercial-grade generator, two EV chargers, and a three-car garage make remote work and daily life effortless. 5 min to Summit Store and 20 min to downtown Los Gatos, with Silicon Valley within commuting reach and prime mountain biking out your door--close enough to feel connected, far enough to exhale. A rare property with space to gather, unwind, and enjoy the best of the Santa Cruz Mountains.

26765 Havenhill LN, Los Gatos

Listed by Mike Bloch, 831-588-1588 from Christie's International Real Estate Sereno
(If provided) CoList: Lindsey Didia from Christie's International Real Estate Sereno

$590,000

ML82050404 MLS

Own your own working vineyard in the Los Gatos Mountains, complete with ocean views and award-winning Los Gatos schools. This exceptional 2.5-acre parcel features approximately 500 organically farmed Pinot Noir vines that have produced grapes for the past 27 years, along with Sauvignon Blanc vines bordering the upper property line. Gently sloping terrain, mature oak trees, and a privacy fence create a peaceful, private setting with endless possibilities. On clear days, enjoy views stretching to Monterey Bay, providing a spectacular backdrop for a custom home designed to capture both mountain and ocean vistas. Some infrastructure is already in place, including a shared well and power available at the street. Located in a Firewise USA community, which may help reduce insurance costs, and just minutes from the Summit Store offering gourmet foods, groceries, a full-service butcher, and espresso. Downtown Los Gatos and the beaches of Capitola are approximately 20 minutes away. Whether you envision a boutique vineyard estate, modern mountain retreat, or private sanctuary, this rare property is served by Loma Prieta Elementary, C.T. English Middle School, and Los Gatos High School.

0 Miller Hill RD, Los Gatos

Listed by Janet Souza, 408-805-3349 from Christie's International Real Estate Sereno
(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

$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 private acres at 19534 Montevina Rd in Los Gatos. This rare hillside retreat features three separate dwellings, combining luxury living, usable land, and flexible space just minutes from downtown. The main villa offers 4 bedrooms and 3.5 bathrooms with breathtaking views of the San Jose city lights from its main living areas and outdoor spaces. Step outside to your private vineyard producing your own custom-labeled wine before arriving at an impressive Auto House built for car enthusiasts. The Auto House includes five car bays for collectors, plus an office and wet bar, creating the perfect setting for storage, display, and entertaining. Down the hill, a separate gated entry leads to a barn with 8 stalls, ideal for livestock or equestrian use. Configured as a working farm, the barn includes a laundry room and bathroom downstairs, with a fully permitted 2-bedroom, 3-bathroom living space upstairs perfect for ranch hands, rental income, guests, or returning adult children. Enjoy close proximity to the El Sereno Open Space Preserve Trail, world-renowned schools, and all the incredible restaurants and entertainment Los Gatos has to offer.

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

$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

$1,895,000

3 Beds ⋅ 2 Baths ⋅ ML82037619 MLS

Ocean Views clear to Monterey from this quiet location nestled in nature! Stunning views every day! Served by top schools & just minutes from downtown Los Gatos and Santa Cruz beaches. This home boasts 1,900 square feet with gleaming hardwood floors; an updated kitchen with quartz counters, breakfast area and bar seating at the center island plus a beautiful view! 3 bedrooms + an office (with a lot); a family room & sunny dining room. You'll love working from home! 2 car garage with storage AND a huge 24 x 48 detached garage/workshop with full bathroom, air compressor, oversized door & pull-through capabilities. The awesome property is 5.69 acres w/over 3 acres fully fenced w/gated entry. Versatility in the land! A small private wine/table grape vineyard + orchard with several varieties of fruit trees including: apple, pear, peach, fig, persimmon, lemon plum, orange & pomegranate. Separate garden space. 10,000 gallons of water storage; an adorable tree house; ample outdoor space for entertaining & plenty of parking! Located in an award winning school district and an easy commute to Santa Cruz or the Silicon Valley this property has it all. Expand the vineyard or enjoy your private harvest! So many possibilities here!

24854 Skyland RD, Los Gatos

Listed by Bobbie J. Herteman, 831-566-5835 from Bobbie Herteman Real Estate
(If provided) CoList: from

$2,400,000

ML82023205 MLS

This property is one of the 4 lots available (544-58-015 with 4 acres) within the 20+ year established, exclusive, private, and gated 8 lot subdivision, Black Ridge Vineyard Estates. Perched high above the valley, offering world-class vineyard land and ready-to-build luxury trophy homesites. Just 1 exit from downtown Los Gatos, this location grants both secluded tranquility and exceptional convenience. As you enter, the level of attention and care is immediately evident, a testament to exquisite craftsmanship and the use of the finest quality materials throughout the existing infrastructure. The estate parcels highlight the natural surroundings and incredible hilltop and vineyard views. 3 of the 8 parcels within the subdivision are built out with magnificent custom homes and now 4 of the 5 remaining vineyard parcels may be purchased as a package or select your favorite one (ranging in size: 3.5, 4.0, 4.9, and 11 acres, totaling 23+ acres). Underground utilities and street improvements, reports are available, including topo, engineering, perc test, and a geotechnical report. The established neighborhood features CC&Rs to assure the quality of future custom homes. The 8 parcels collectively own a Mutual State Small Water Company, which is supplied by on-site wells.

18650 Black RD, Los Gatos

Listed by Paul Burrowes, 408-497-3989 from David Lyng Real Estate
(If provided) CoList: from

$2,600,000

ML82023203 MLS

This property is one of the 4 lots available (544-58-014 with 3.5 acres) within the 20+ year established, exclusive, private, and gated 8 lot subdivision, Black Ridge Vineyard Estates. Perched high above the valley, offering world-class vineyard land and ready-to-build luxury trophy homesites. Just 1 exit from downtown Los Gatos, this location grants both secluded tranquility and exceptional convenience. As you enter, the level of attention and care is immediately evident, a testament to exquisite craftsmanship and the use of the finest quality materials throughout the existing infrastructure. The estate parcels highlight the natural surroundings and incredible hilltop and vineyard views. 3 of the 8 parcels within the subdivision are built out with magnificent custom homes and now 4 of the 5 remaining vineyard parcels may be purchased as a package or select your favorite one (ranging in size: 3.5, 4.0, 4.9, and 11 acres, totaling 23+ acres). Underground utilities and street improvements, reports are available, including topo, engineering, perc test, and a geotechnical report. The established neighborhood features CC&Rs to assure the quality of future custom homes. The 8 parcels collectively own a Mutual State Small Water Company, which is supplied by on-site wells.

18700 Black RD, Los Gatos

Listed by Paul Burrowes, 408-497-3989 from David Lyng Real Estate
(If provided) CoList: from

$4,600,000

ML82023200 MLS

This property is one of the 4 lots available (544-58-012 with 11.08 acres) within the 20+ year established, exclusive, private, and gated 8 lot subdivision, Black Ridge Vineyard Estates. Perched high above the valley, offering world-class vineyard land and ready-to-build luxury trophy homesites. Just 1 exit from downtown Los Gatos, this location grants both secluded tranquility and exceptional convenience. As you enter, the level of attention and care is immediately evident, a testament to exquisite craftsmanship and the use of the finest quality materials throughout the existing infrastructure. The estate parcels highlight the natural surroundings and incredible hilltop and vineyard views. 3 of the 8 parcels within the subdivision are built out with magnificent custom homes and now 4 of the 5 remaining vineyard parcels may be purchased as a package or select your favorite one (ranging in size: 3.5, 4.0, 4.9, and 11 acres, totaling 23+ acres). Underground utilities and street improvements, reports are available, including topo, engineering, perc test, and a geotechnical report. The established neighborhood features CC&Rs to assure the quality of future custom homes. The 8 parcels collectively own a Mutual State Small Water Company, which is supplied by on-site wells.

18570 Black RD, Los Gatos

Listed by Paul Burrowes, 408-497-3989 from David Lyng Real Estate
(If provided) CoList: from

$14,200,000

ML82023193 MLS

This property presents an unparalleled offering within the 20+ year established, exclusive, private, and gated 8 lot subdivision, Black Ridge Vineyard Estates. Perched high above the valley, offering world-class vineyard land and ready-to-build luxury trophy homesites. Just 1 exit from downtown Los Gatos, this location grants both secluded tranquility and exceptional convenience. As you enter, the level of attention and care is immediately evident, a testament to exquisite craftsmanship and the use of the finest quality materials throughout the existing infrastructure. This offering includes 4 legal estate parcels that highlight the natural surroundings and incredible hilltop and vineyard views. 3 of the 8 parcels within the subdivision are built out with magnificent custom homes and now 4 of the 5 remaining vineyard parcels may be purchased as a package or select your favorite one (ranging in size: 3.5, 4.0, 4.9, and 11 acres, totaling 23+ acres). Underground utilities and street improvements, reports are available, including topo, engineering, perc test, and a geotechnical report. The established neighborhood features CC&Rs to assure the quality of future custom homes. The 8 parcels collectively own a Mutual State Small Water Company, which is supplied by on-site wells.

18570+ Black RD, Los Gatos

Listed by Paul Burrowes, 408-497-3989 from David Lyng Real Estate
(If provided) CoList: from

$1,150,000

ML82018990 MLS

Welcome to your future Tuscan-inspired estate, nestled in the scenic foothills of Los Gatos where rolling vineyards, oak-studded hillsides, and sweeping vistas create the perfect backdrop for luxury living. Just minutes from downtown Los Gatos, award winning schools, boutique shopping, fine dining, hiking trails, wineries and freeway access, this property offers both tranquility and convenience. Set on 1.19 acres, the proposed 4,310 sqft residence features a detached 2 car garage with workspace plus an attached 1 car garage. The homesite is ideally positioned to capture panoramic views while providing privacy and serenity. Much of the preparation work has already been completed: architectural plans, civil plans, soil engineering report, and topographic survey, with water and electricity nearby. This significantly shortens the development timeline, creating a rare opportunity for buyers looking to custom build their dream home or investors seeking a premier project in one of Silicon Valleys most desirable communities. Buyer to verify all disclosures, reports and information provided to their satisfaction.

14721 Shannon RD, Los Gatos

Listed by Nikil Balakrishnan, 408-813-8001 from Realty World Premier Properties
(If provided) CoList: Mohini Balakrishnan from Realty World Premier Properties

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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 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.