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25373 Spanish Ranch RD, Los Gatos
$13,000,000
3 Beds ⋅ 2 Baths ⋅ ML82021201 MLS
Extraordinary opportunity offering the ultimate in privacy and natural beauty. Enjoy 12 miles of groomed trails that wind through pristine, forested land, creating endless possibilities for hiking, biking, and exploring. Several access points to Soquel Creek provide serene water views and scenic moments. Wildlife abounds here, with sightings of deer, turkeys, and trout, creating a true sanctuary in nature. The property includes a 3-bedroom, 2-bath caretakers residence, ensuring year-round maintenance and immediate usability. A potential building site at the propertys highest point offers breathtaking ocean views, allowing for a future custom retreat in a truly unmatched setting. The original sawmill exists and is in operating condition. Located next to Soquel Demonstration State Forest, the land is bordered by protected open space dedicated to education and preservation. While wonderfully secluded, the property also provides convenient access to Silicon Valley and San Francisco, making it an easy getaway and an investment in lifestyle. This is a once-in-a-lifetime opportunity to own one of the largest private collections of old-growth redwoods, offering unmatched beauty, adventure, and tranquility.

25373 Spanish Ranch RD, Los Gatos

Listed by The Dreyfus Group, 650-485-3476 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Bryan Chambers from S1955

15681 Kennedy RD, Los Gatos
$11,350,000
8 Beds ⋅ 11 Baths ⋅ ML82010691 MLS
Experience the epitome of luxury living at Villa di Fiori, an award-winning architectural masterpiece nestled in the breathtaking vistas of Los Gatos, Silicon Valley. This extraordinary multi-generational smart home, recently remodeled in 2025, spans approximately 12,405 sq ft across 3.56 acres of meticulously designed private space. Featuring two exquisite dwellings, a brand new Tesla roof, and an infinity-edge PebbleTec pool with a Jacuzzi, this estate offers 8 sumptuous suites, 10.5 baths, and an array of entertainment options including an expansive theater lounge, game room, executive office, gym, wine cellar, and music room. With state-of-the-art smart home technology, 24-hour surveillance, and stunning panoramic sunset views, Villa di Fiori is not just a home; its a sanctuary of elegance and innovation, perfect for hosting grand gatherings or enjoying serene moments in your own private oasis. Experience the cascading waterfall and scent of fresh flowers, verandas & fountains accented by roses, Italian Cypress, a lush olive grove and pristine sculpture gardens. Minutes from the vibrant downtown Los Gatos, indulge in a lifestyle rich with art, culture, and culinary delights, all while surrounded by the beauty of Italian-inspired gardens and tranquil courtyards. Welcome home.

15681 Kennedy RD, Los Gatos

Listed by Ofelia Ventura, 408-218-1405 from KW Silicon City
(If provided) CoList: from

Sold listing courtesy of Greg Simpson from KWLGE

16140 Matilija DR, Los Gatos
$11,000,000
6 Beds ⋅ 8 Baths ⋅ ML82030244 MLS
Spectacular single-story estate offering modern luxury, privacy & smart-home living in a prime Los Gatos location with top Saratoga schools. Sprawling contemporary residence set amid lush gardens, rolling hills & sweeping views. Generous interior features curated finishes & open living spaces with picture windows, skylights, high ceilings & custom woodwork, creating seamless indooroutdoor flow. Two private wings include six en-suite bedrooms & an executive office on the main level, including two primary suites with spa baths & custom built-ins, plus two J&J suites. Two laundry rooms, one of each wing. Sleek designer kitchen showcases a dramatic crescent-shaped island with walnut counter bar & premium Gaggenau, Perlick & Miele appliances. Family room features a striking metal entertainment console; living & dining rooms with walls of glass overlook the rear grounds. Lower level includes a bonus room, full bath, lounge & wine cellar. Resort-style outdoor living offers expansive patios, pool & spa, built-in BBQ, fire pit, play area, raised planter beds, bocce & horseshoe courts. Pool house/ADU with dressing area. Minutes to downtown Los Gatos, Saratoga Village, hiking & biking trails & an easy Silicon Valley commute. Refined, elegant & exceptional comfort for the most discerning!

16140 Matilija DR, Los Gatos

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

Sold listing courtesy of Kimberly Douglas from REEX

109 Sporleder CT, Los Gatos
$7,900,000
5 Beds ⋅ 7 Baths ⋅ ML82055447 MLS
New construction contemporary home offering approximately 6,671 SF on an approximately 16,000 SF lot. This 5-bedroom, 6 full and 1 half bath residence spans three levels with 10-foot ceilings, 7-inch European White Oak hardwood flooring, flush baseboards, stained cabinetry and interior doors, and abundant natural light. The main level features a dramatic two-story entry, spacious great room with fireplace and sliding doors to the backyard, dining room with wine bar, gourmet kitchen with oversized island and built-in dining table, Viking 48-inch built-in refrigerator, Viking 48-inch induction range, large laundry room, office/nursery, and a main-level primary suite. The primary bath features radiant heated floors, freestanding tub, walk-in shower, and oversized walk-in closet with a $10,000 builder credit toward a custom closet system. Upstairs are two ensuite bedrooms with walk-in closets. The lower level includes a large recreation room with wet bar/kitchenette, temperature-controlled wine room, theater/game room, gym or golf simulator room, additional bedroom with full bath, and storage. Expansive backyard offers room for a pool (buyer to verify). Oversized two-car garage. Convenient Los Gatos location near shopping, dining, parks, and commuter routes.

109 Sporleder CT, Los Gatos

Listed by Tom Yore, 408-691-6024 from KW Bay Area Estates Saratoga
(If provided) CoList: Theresa Van Zant from KW Bay Area Estates

Sold listing courtesy of Rick Chehab from AMWST

140 Twin Oaks DR, Los Gatos
$7,800,000
5 Beds ⋅ 5 Baths ⋅ ML82044168 MLS
A beautifully executed, move-in ready luxury residence in the highly sought-after Surrey Farms neighborhood, this custom home by architect Gary Kohlsaat blends refined design, resort-style amenities, & a premier Los Gatos setting on a thoughtfully designed half-acre. Expansive living spaces flow into an open-concept kitchen & family room, where side-by-side La Cantina doors open to the resort-style grounds. The gourmet chefs kitchen is designed for both everyday living & entertaining, featuring premium appliances, an oversized waterfall island, designer finishes, & seamless connection to the main gathering spaces. The backyard is a true retreat with pool, spa, fire pit, turf lawn, play areas, built-in trampoline, sauna, outdoor shower, & covered loggia with fireplace, skylight, TV & outdoor kitchen with Evo grill. The primary suite offers a private deck, spa-like bath, & dual walk-in closets, while a detached ~800 sq ft pool house/ADU includes a living area, optional bedroom/dance-yoga studio & full bath for flexible living or guests. Additional features: game room, dedicated office, ground-level en-suite bedroom, smart home features, mudroom, & ~973 sq ft three-car garage with epoxy floors, home gym, & built-in storage. A truly special home with coveted Los Gatos schools.

140 Twin Oaks DR, Los Gatos

Listed by Fran Papapietro, 408-623-4155 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Lisa Radding from CBR

16541 Cypress WAY, Los Gatos
$7,450,000
5 Beds ⋅ 8 Baths ⋅ ML82008476 MLS
Château de la Vue | Elevated above Los Gatos, boasts over 9,500 sq. ft. of living space and presides over an ultra-private 2-acre estate where panoramic 180° views stretch from the lights of Silicon Valley to the skyline of San Francisco. This dual-gated compound offers an unmatched blend of security, tranquility, and architectural significance just minutes from downtown Los Gatos. The main residence spans over 7,000 sq. ft. with 4 bedrooms accompanied by 5 bathrooms and an executive office. The interior balances timeless luxury with dramatic indoor-outdoor flow, creating seamless entertaining experiences across expansive terraces, views, and landscaped grounds. A separate, over 2,200 sq. ft. guest house, accessed via its own gated driveway delivers full dual-living flexibility across two levels, each with its own kitchen, accompanied by 1 bedroom and 3 bathrooms. Ideal for multigenerational living or a private retreat. Resort-style amenities include a 75-foot lap pool and spa, movie theater, gym, and oversized 3-car garage.. Modern regulations make replication of an estate of this size, above ground, virtually impossible today. Chateau De La Vue is a generational opportunity to own one of Silicon Valleys most iconic, irreplaceable estates!

16541 Cypress WAY, Los Gatos

Listed by The Gummow Brothers, 408-616-9146 from Christie's International Real Estate Sereno
(If provided) CoList: Kirsten Trapani from Christie's International Real Estate Sereno

Sold listing courtesy of The Gummow Brothers from SGP

652-656 N Santa Cruz AVE, Los Gatos
$7,400,000
ML82026895 MLS ⋅ Shower Park LLC BLDG.
KW Commercial South Bay, on behalf on ownership, is proud to present a rare opportunity of a trophy investment property in the heart of Downtown Los Gatos. The property features three versatile and well-maintained buildings, totaling 16,499 square feet, thoughtfully designed for mixed-use functionality including retail, office, and residential. Each structure contributes to a dynamic and flexible investment profile, ideal for long-term income and value appreciation. Positioned on a generous 42,086 square foot lot, the property offers prominent visibility with approximately 189 feet of frontage along bustling North Santa Cruz Avenue, and convenient secondary access via Industrial Avenue. This prime location, combined with its diverse use potential and strategic layout, makes the property a standout investment in one of Silicon Valleys most desirable markets.

652-656 N Santa Cruz AVE, Los Gatos

Listed by Mark Von Kaenel, 408-568-6602 from KW Bay Area Estates
(If provided) CoList: David Giambruno from KW Bay Area Estates

Sold listing courtesy of J.J. Taughinbaugh from M&MKW

23020 Old Santa Cruz HWY, Los Gatos
$7,350,000
5 Beds ⋅ 6 Baths ⋅ ML82015557 MLS
One-of-a-kind luxury estate set on ~30 acres with sunny pastures, redwood forest, & distant bay views. Impressive colonial style home with grand entry hall, formal living & dining rooms, family room, billiards room/library, wine tasting room with wine cellar, sumptuous primary suite with loft, 3rd floor recreation room & unfinished attic space, planned as home theater, has plumbing for half bath. All bedrooms have ensuite baths, 5th bed with wet bar over att. 3 car garage, and huge laundry room (potential 2nd kitchen). Detached guest house/legal ADU with own address: 3 beds/2.5 baths, sun room, private patio. Outdoor kitchen/living area with stone fireplace, European style pond with waterfall, beach entry & deck. Fenced gardens with custom pergola, mature orchard, bocce court. Fiberglass dome observatory with telescope, floodlit all-weather sports court, 60'x36' MD Barnmaster barn (inc. car lift, houses sellers' car collection), barn door raised for RV. Level/gently sloped fenced pastures, ample space to add a riding arena. Private trails through the redwood forest. Potential equestrian use, winery, organic farm, retreat/sanctuary. New roof, 22.5W solar system, auto generators for both houses. Only 1.5miles from Hwy 17, 8 miles/10-12 mins to downtown Los Gatos

23020 Old Santa Cruz HWY, 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

Sold listing courtesy of Amin Kuchaki Rafsanjani from PY2PP

15651 Kennedy RD, Los Gatos
$6,940,000
4 Beds ⋅ 4 Baths ⋅ ML82017790 MLS
Don't wait! For a limited time Seller will entertain offers between $7.3M and $8M for the entire 9.6 acre property with ability to capture up to 3 legal developable parcels. One parcel currently offered for sale at $1.8M pending approvals (ML82017796). Options abound: keep the existing home while gaining two new parcels to develop or sell, offset costs by selling one or more parcels, or double the property's underlying value and hold for generational wealth. Arguably one of the finest estate properties in Los Gatos, this fully fenced and gated retreat offers unmatched privacy features sweeping 270 degree views of bucolic hills and the valley below. Despite being less than 5 minutes to Los Gatos Blvd, this multi-acre property features meandering trails wind through organic fruit trees, custom enclosures, and landscaped grounds with sunset vistas. Outdoor amenities include bocce, volleyball, swimming, and multiple gathering areas. The recently updated home is centered around a beautiful courtyard entry and features spacious bedrooms, a serene office, and multiple entertainment spaces. Expansive Brazilian Ipe decking surrounds the residence, framing sweeping hillside views. Located minutes from Los Gatos High, fine dining, and shopping, and served by top-rated Los Gatos schools.

15651 Kennedy RD, Los Gatos

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

Sold listing courtesy of George Lee from FT23T

130 Longmeadow DR, Los Gatos
$6,800,000
5 Beds ⋅ 4 Baths ⋅ ML82049070 MLS ⋅ Surrey Farms BLDG.
This stunning modern farmhouse has been meticulously renovated & thoughtfully designed by Kim Anderson of Arcadia Design known for Martis Camp interiors. Featuring refined finishes, elegant architectural details & warm, inviting aesthetic throughout. Shows like a model with numerous amenities. Gourmet chef's kitchen with custom cabinetry and Carrara marble surfaces. Commercial grade S/S appliances. All baths are unique to their own design. Primary bedroom features gas fireplace, huge walk-in closet & romantic primary bath. Wide plank wood flooring throughout . Formal living room gas fireplace & french doors to patio. Formal dining room with high ceiling . Features include cloth walls. Separate guest house features a full bath, steam shower, entertaining bar/kitchen, cooled wine cellar, including a Full Swing golf simulator and Swing Catalist analysis system and projector, and wide plank wood floors. Central HVAC. Outdoor sitting area w/heaters, flat screen TV & speakers. The exterior features numerous sitting & entertaining area's. There's a sparkling in-ground pool w/ beach access & electric cover. Separate gas fireplace. Full outdoor kitchen featuring a gas grill, beer refrigerator & dispenser, sink, refrigerator, granite counters bar seating,heaters, flat TV, speakers, Solar

130 Longmeadow DR, Los Gatos

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

Sold listing courtesy of Mark Chiavetta from CBR

16781 Littlefield LN, Los Gatos
$6,775,000
6 Beds ⋅ 7 Baths ⋅ ML82038523 MLS
Exceptional Custom Craftsman Style Home with Incredible Designer Fixtures and Finishes throughout. Built in 2015 and already remodeled with style and luxury. The grand entry and welcoming living room have 21 ft ceilings, radiant windows and an impressive floor to ceiling stone fireplace. The distressed hardwood floors and dining area are accented by a reclaimed wood wall with two perfectly fitted sconces. Phenomenal Chef's Kitchen includes an oversized Quartzite island, awesome 42" Viking 6-burner range with griddle, pot filler, used brick exhaust hood, walk-in pantry, extensive cabinetry, separate beverage refrigerator and more. Open-concept family-great room has a perfect spot for a large everyday dining table with two stylish light fixtures. Another beautiful stone fireplace is balanced by art lighting on both sides. 6-Panel By-Folding Doors all open to the oversized backyard with paver patio. The spacious primary suite boasts a private deck, spa like bathroom and walk-in closet is upstairs along with 3 additional bedrooms and large laundry room. Lower level is an entertainers dream! Full service bar with all the amenities. Theater Room, exercise room and an en-suite bedroom. 4-car garage has epoxy flooring and a car lift. Close proximity to the sought after Los Gatos Schools.

16781 Littlefield LN, Los Gatos

Listed by Greg Simpson, 408-832-2323 from KW Bay Area Estates
(If provided) CoList: from

Sold listing courtesy of Fran Papapietro from SGP

115 Glenridge AVE, Los Gatos
$6,750,000
6 Beds ⋅ 4 Baths ⋅ ML82042289 MLS
Iconic Craftsman property sits proudly in one of the most desirable locations in dwntwn Los Gatos! Just short stroll to the hustle & bustle of Los Gatos' dining & shopping district & nearby hiking & biking trails, the calm peaceful ambience of this pristine setting will not disappoint. One of LG''s most treasured historic residences, a white picket fence frames the front facade w/ trailing white roses intertwined among pickets. Meandering brick path extends to large wrap-a-round porch entry. Expansive living spaces w/ large picture windows & French doors showcase boxed beam ceilings, lovely casework & hdwd floors, period details w/ updated systems. Kitchen-prof grade appliances including Subzero refrig, gas range, 2 ovens, warming drawer & sep bar sink, butlers pantry. 6 bdrms, including 3 en-suite. Upstairs suite enjoys beautiful hillside views, large bath w/ soaking tub & generous shower. Dedicated laundry on ea floor. Gardens to relax & enjoy, boxwood hedges frame fragrant lavender. Blooming hydrangea & sculptural maple trees flank walking paths & lawn. Water cascades at fountain next to covered arbor, a delightful spot to dine & relax. Raised irrigated planters & workshop. Detached oversized 2 car garage & extra parking provided at rear of property. Top Los Gatos schools!

115 Glenridge AVE, Los Gatos

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

Sold listing courtesy of Ducky Grabill from SGP

16220 S Kennedy RD, Los Gatos
$6,600,000
5 Beds ⋅ 5 Baths ⋅ ML82060328 MLS
Resort-style living meets Silicon Valley convenience at this exceptional custom built, single-level residence. Gated & privately positioned on a flat acre just minutes from vibrant downtown Los Gatos, this property seamlessly connects sophisticated interiors with extraordinary outdoor spaces, creating a private retreat equally suited for everyday living & entertaining. The residence centers around an open kitchen-family great room overlooking the spectacular grounds. The chef's kitchen features an island with seating, Wolf/Sub-Zero/Thermador appliances, slab counters & walk-in pantry. A spacious living/dining room provides an elegant setting for larger gatherings. A private bedroom wing features a gracious primary suite with fireplace, sliding French doors, dual-sided walk-in closet & spa-inspired bath. A separately positioned 4th bedroom with full bath is ideal for guests or a private executive office. The detached guest house is a destination unto itself with its great room, full kitchen, bedroom suite & laundry. Outside, the property transforms into a private oasis. Expansive lawns surround a sparkling pool & spa, bocce court & outdoor kitchen pavilion. Solar, 3-car garage, Los Gatos schools, moments to downtown LG & convenient access to leading Silicon Valley tech campuses.

16220 S Kennedy RD, Los Gatos

Listed by Billy McNair, 650-862-3266 from Coldwell Banker Realty
(If provided) CoList: Andrea Schultz from Coldwell Banker Realty

Sold listing courtesy of Mimi Trieu from RDFIN

146 Tait AVE, Los Gatos
$6,518,929
5 Beds ⋅ 5 Baths ⋅ ML82035234 MLS
Located in a highly desirable setting in the heart of downtown Los Gatos, this beautifully updated residence offers 3,429sq ft in the main home with 4 bedrooms and 3.5 baths, plus a flexible office/yoga studio, and the 5th bedroom is a detached 1-bed, 1-bath cottage (210 sq ft) ideal for guests, extended family, or private work-from-home retreat. Since 2018, the property has benefited from over $700K in improvements, including new A/C and furnace for the main home, new HVAC and hardwood floors in the cottage, and a fully integrated A/V and whole-home internet system. The kitchen has been thoughtfully refreshed with new Perrin & Rowe hardware, a professional Wolf gas range, complemented by a marble backsplash in both the kitchen and butler's pantry. Interiors are elevated by a striking stone fireplace wall in the great room and refinished hardwood floors throughout. The resort-style backyard is a true showpiece, completely reimagined with an outdoor fireplace and a built-in BBQ, earning 1st Place in the Medium Landscape Category (CLCA Awards, 2021). The improvements by JT Masters Construction reflect quality craftsmanship throughout. Dining, boutiques, Sunday Farmer's Market, trails, and more, this is turnkey living in one of Silicon Valley's most sought-after neighborhoods.

146 Tait AVE, Los Gatos

Listed by Steve&ChristinePerry, 408-391-4465 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of DeLeon Team from DLRPA

5770 Harwood PL, Los Gatos
$6,400,000
5 Beds ⋅ 5 Baths ⋅ ML82056345 MLS
This Hacienda View Estate emerges as a rare legacy property of exceptional distinction, encompassing 4.4 private acres of uncompromised privacy, & timeless elegance. This meticulously designed estate commands sweeping city light and valley views that unfold in panoramic splendor, offering a serene sanctuary mere moments from the charm of downtown Los Gatos and the dynamic innovation corridor of Silicon Valley. Boasting a total enclosed area of approximately 8,731 SQFT for the main house, and including al 600 SQFT guest quarters. The estate features a spectacular glass-enclosed solarium with a retractable roof. This architectural triumph seamlessly integrates with an enormous California Room, creating an expansive year-round indoor-outdoor living experience. The chefs kitchen stands as a culinary masterpiece, elegantly appointed with premium quartz countertops, high-end finishes, and an abundance of natural light. The main residence encompasses four bedrooms, an office, and a guest quarters providing exceptional flexibility for multigenerational living. A grand motor court and striking architecture create an unforgettable sense of arrival, establishing this estate as a true family compound of rare versatility, peace, and enduring legacy! By far the best view estate in Los Gatos!

5770 Harwood PL, Los Gatos

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

Sold listing courtesy of Desiree Dutra from CBR

14942 Larga Vista DR, Los Gatos
$6,250,000
4 Beds ⋅ 4 Baths ⋅ ML82056494 MLS
San Francisco to Gilroy views from 13.5 acres in Los Gatos, with usable, gently sloped land near the home and hillside beyond, shaded by heritage oak trees. Room for farm animals or a future vineyard. Minutes from downtown Los Gatos, Saratoga, Campbell, and San Jose, with easy freeway access. The 2,830 sq ft home has a Tahoe-esque feel, hardwood and tile floors, and was extensively remodeled in 2017. The kitchen is built for real cooking: six-burner stove, pot filler, double ovens, and its own fireplace. Solid core doors throughout. The primary suite has a fireplace and feels like its own retreat. 4 bedrooms, 3.5 baths. Attached 2-car garage plus a detached 2-car garage with pool storage, and a pool. Outdoor kitchen and two sitting areas make this the spot for every family gathering, with land still left over to explore. Part of the original Blossom Hill, this is only the second time the property has changed hands in over 100 years! If you love a view, this is the one to see; it has some of the best in Silicon Valley.

14942 Larga Vista DR, Los Gatos

Listed by Suzanne Freeze Manning, 408-623-5599 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Nikil Balakrishnan from RWXE

16070 Matilija DR, Los Gatos
$6,250,000
5 Beds ⋅ 7 Baths ⋅ ML82053834 MLS
Welcome Home to 16070 Matilija Dr, a 3,050 SF Main House + 1,000 SF ADU a Gorgeous Estate in a Prestigious Los Gatos Location w/ Saratoga Schools! Set on Over Half an Acre w/ a 4BD Main Home + Detached 1BD ADU, 4 Full & 3 Half Baths & Mountain Views. Driveway w/ Paver Apron, Cultured Limestone Facade, Covered Entry w/ Exterior Chandelier & Oversized Pivot Door Provide Gorgeous Curb Appeal. Open Floor Plan w/ 10' Ceilings, White Oak Wide-Plank Hardwood Floors, Skylights & Sun Tunnels. Great Room w/ 72" Linear Fireplace, Travertine Surround & Multi-Directional Sliding Doors. Chef's Kitchen w/ Raised Ceiling, Skylights, Long Quartzite Island, Lavender Marble Counters & Backsplash, Pass-Through Bi-Fold Windows, Viking & Wolf Appliances. Primary Suite w/ Mountain Views, Back Garden Access, Custom Walk-In Closet & Spa-Like Ensuite w/ Radiant Heat, Dual Vanity, Oversized Shower & Standalone Tub. Detached ADU w/ Full Kitchen, Laundry, Bedroom Suite & Mini-Split Heating/Cooling. Finished 2-Car Garage w/ Epoxy Floors, Cabinetry, Skylights & Half Bath. Back Patio w/ Pergola, Outdoor Kitchen, Artificial Lawn, Water Feature & Resort-Style Landscaping. Minutes to Downtown Los Gatos & Saratoga, Farmers Markets, Hwy 17, Apple & NVIDIA.

16070 Matilija DR, Los Gatos

Listed by Andy Tse, 408-807-8808 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Arthur Sharif from SIR

227 Alexander AVE, Los Gatos
$6,250,000
4 Beds ⋅ 3 Baths ⋅ ML82045746 MLS
Walk to Downtown Los Gatos from this beautifully remodeled home in the premier Glen Ridge neighborhood. Extensively updated since ownership, the residence pairs classic curb appeal with a thoughtfully reimagined interior and modern systems. A lush front setting with blooming roses and a mature oak canopy creates a warm first impression. Inside, wide-plank engineered hardwood floors, vaulted ceilings, and abundant natural light define the living spaces. The living room sits just off the entry with fireplace and picture windows with plantation shutters. The kitchen is designed for everyday living and entertaining, fully updated with top of the line appliances, custom cabinetry, and under-cabinet lighting. Dining and family room areas open to the patio through French doors, enhancing indoor-outdoor flow. The main level includes 3 guest beds, 2 full baths and laundry closet. The expansive primary suite occupies the upper level with vaulted wood-plank ceilings, private balcony, soaking tub, tile shower, skylights, multiple closets, and laundry. A lower-level bonus room adds flexibility. The backyard enjoys a tile patio with built-in BBQ, mature oak and ample land to enjoy. Paved driveway lined with greenery leads to the detached 2-car garage with epoxy flooring. This home has it all!

227 Alexander AVE, 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

Sold listing courtesy of Greg Simpson from KWLGE

16371 Aztec Ridge DR, Los Gatos
$6,000,000
5 Beds ⋅ 5 Baths ⋅ ML82039380 MLS
Welcome to 16371 Aztec Ridge, a 5-bed, 4.5-bath estate set on approximately 2 acres above Los Gatos, offering sweeping views across Silicon Valley and stretching to San Francisco. A gated entry leads to a beautifully maintained setting with expansive parking and a 3-car garage. Inside, the home opens to a grand foyer framed by walls of glass that capture the surrounding landscape. The main level is designed for both everyday living and entertaining, featuring a chef's kitchen with a walk-in pantry, formal dining room, and multiple living spaces that flow seamlessly to outdoor balconies. The lower level offers a private guest suite, game room, and flexible living areas, along with a pre-built home theater ready for completion. Smart home integration allows for effortless control of lighting and systems throughout. The backyard delivers a true resort experience, highlighted by a walk-in infinity-edge pool with a 75-foot water slide, outdoor kitchen, fireplace, and multiple entertaining areas. A private lookout creates the perfect setting to take in city lights and fireworks, while a large turf area adds space for recreation. Located within the highly regarded LG School District and just minutes from downtown, this property offers a rare combination of privacy and lifestyle.

16371 Aztec Ridge DR, Los Gatos

Listed by Benjamin Frieden, 408-888-9507 from KW Bay Area Estates
(If provided) CoList: Jason D'amico from KW Bay Area Estates

Sold listing courtesy of Francesca Lampert from CBR

16484 S Kennedy RD, Los Gatos
$5,880,070
6 Beds ⋅ 8 Baths ⋅ ML82035442 MLS
New Construction to be Built! Located on the prestigious South Kennedy Road, these two side-by-side parcels each span just over one acre, offering approximately one acre of usable flat land per parcel. The architectural renderings reflect thoughtfully designed residences that will be built with exceptional quality, attentional to detail, and enduring craftsmanship. Each proposed home offers massive living space. Parcel 1 offers 6,387 SqFt. JADU of 500 SqFt. 6 beds and 7.5 baths. Parcel 2 offers 6,375 SqFt. 6 beds and 6.5 baths and a 3 car garage. Both residence also include a separate office/bonus room, and an I.T room. The stunning properties are situated near Los Gatos Boulevard and surrounded by other distinguished multi-million dollar estates. These homes are part of a lot split project that the town of Los Gatos is excited to see come to life. Located within the highly sought-after Los Gatos school district. These homes will be built by 1One Development Group, known for their signature standard of excellence, these homes will reflect superior craftmanship, striking design, and a commitment to quality that sets them apart.

16484 S Kennedy RD, Los Gatos

Listed by Christina Aguirre, 408-728-2393 from The Agency
(If provided) CoList: from

Sold listing courtesy of Christina Aguirre from AGNC

17435 Phillips AVE, Los Gatos
$5,850,000
5 Beds ⋅ 5 Baths ⋅ ML82021076 MLS
Stunning custom Mediterranean estate boasts a private setting on 1.45 acres with peaceful views of the Los Gatos hills. This 5,166 sf, 5 bedroom, 4.5 bathroom home exudes sophisticated elegance and comfort with soaring 12 ceilings, wide plank hardwood floors, custom mill work and generous rooms. Impeccable quality and craftsmanship blends tasteful design and modern high-end amenities throughout. The beautifully maintained landscape features a Cabernet vineyard, flower covered trellises, illuminated gardens and a private patio that is an ideal setting for gatherings or quiet relaxation. The grounds also include room for a pool, additional vineyard, sport court, or possible ADU. Close to vibrant downtown Los Gatos with casual and fine dining, boutique shopping, Farmers market, community events and hiking/biking trails. Distinguished Los Gatos schools.

17435 Phillips AVE, Los Gatos

Listed by Nevis and Ardizzone, 408-781-0779 from Compass
(If provided) CoList: from

Sold listing courtesy of Eric Chang from CRBG

16255 Short RD, Los Gatos
$5,700,000
4 Beds ⋅ 4 Baths ⋅ ML82043859 MLS
Tucked into one of Los Gatos most sought-after, country-style lanes, 16255 Short Road offers a rare blend of privacy, scale, and natural beauty on 0.56+/- acre with picturesque hillside views. Designed by renowned architect Chris Spaulding and built by Dave Flick, this beautifully maintained residence showcases timeless craftsmanship and thoughtful design. Featuring 4 bedrooms plus a main-level office (optional 5th bedroom), the home offers a versatile and functional floor plan ideal for both everyday living and entertaining. Expansive windows, soaring ceilings, and multiple fireplaces fill the home with natural light and warmth. The dramatic family room opens seamlessly to a chefs kitchen with premium appliances, center island, and walk-in pantry. Outdoor living is exceptional, with a pool, spa, expansive patios, and lush grounds oriented to capture stunning sunset views. A separate outdoor office/studio provides added flexibility. Additional highlights include a newer roof and beautifully landscaped grounds. Located just minutes from downtown Los Gatos with boutique shopping, dining, and top-rated Los Gatos schools.

16255 Short RD, Los Gatos

Listed by Nevis and Ardizzone, 408-781-0779 from Compass
(If provided) CoList: from

Sold listing courtesy of Nevis and Ardizzone from COMPS

15955 Cerro Vista CT, Los Gatos
$5,700,000
4 Beds ⋅ 4 Baths ⋅ ML82019338 MLS
Stunning 4B+Office /3.5 bth residence with Los Gatos Schools. This home offers ~5,033 sqft luxurious living space, 2 suites, on ~1.08 acre of park-like land, just 10 minutes away from the downtown. Custom-built in 1991, it went thru a major renovation in 2017-18. Step inside to the 9-12 ft ceilings, an open floor plan and the peaceful views of the Hills! The main floor features a formal living room, dining room, an office, a large high-end kitchen, a spacious family room, the massive primary suite, a powder room & Laundry. The downstairs offers the 2nd suite, 2 more bedrooms w/ a jack & jill bath and walk-in closets, and a wine cellar. The kitchen showcases abundant Omega cabinetry w/ Italian quartzite countertops, large island under a skylight, 2 prep sinks, Sub-Zero refrigerator, Wolf cook range, Asko dishwasher, &butler's pantry. The spacious primary suite w/ a spa-like bath, walk-in closet & fireplace. Enjoy beautiful HW floors, double-pane windows & doors, Multi-zone HVAC, tankless heater, heated tile floors in all full baths, "TOTO" smart toilets, Porcelanosa premium tiles and designer fixtures. Finished 3-car garage. 6.39KW solar panels & 4 Tesla batteries. This exceptional home combines luxury, nature, and convenience in one of Silicon Valley's most desirable communities.

15955 Cerro Vista CT, Los Gatos

Listed by Maggie Li, 650-533-7351 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Katie Keeler from EXPCA

101 Glen Ridge AVE, Los Gatos
$5,400,000
6 Beds ⋅ 6 Baths ⋅ ML82030875 MLS
A landmark residence that embodies the grace, history, and charm of old Los Gatos - this vintage Craftsman stands in the prestigious and highly sought-after Glen Ridge neighborhood. Blending timeless architectural character with modern livability this grand home offers approximately 5,500 square feet of living space featuring expansive rooms, numerous picture windows, rich Hardwood floors and 6 generous bedrooms & 5.5 bathrooms. Set on an expansive 16,910-square-foot corner lot, the property showcases a sparkling pool, multiple outdoor entertaining areas, and two additional usable strips of land ideal for gardens, a bocce court, or putting green. A rare opportunity to own one of Los Gatos most admired legacy homes in a premier downtown location.

101 Glen Ridge AVE, Los Gatos

Listed by Barton Call, 408-483-9632 from Christie's International Real Estate Sereno
(If provided) CoList: Kirsten Trapani from Christie's International Real Estate Sereno

Sold listing courtesy of Mahnaz Westerberg from AGNC

18000 Overlook RD, Los Gatos
$5,375,000
7 Beds ⋅ 5 Baths ⋅ ML82042840 MLS
Welcome to La Estancia, a rare historic estate in Glenridge, one of the towns most sought-after neighborhoods and just moments from exciting downtown Los Gatos. Originally crafted in the late 1800s and refined in 1901 by architect Willis Polk, whose work includes the famed Filoli estate in Woodside, California. This Mission Revival residence blends timeless character with exceptional privacy. Set behind gates on over 1.289 FLAT acres, the property features a grand main home, a guest house, a pool, a cabana, a detached oversized two-car garage, a 1,687 sq ft walkout basement with office and storage, and a tranquil pond with a water feature framed by mature trees. Expansive living spaces highlight rich architectural details, arched openings, and hillside views. Multiple indoor-outdoor areas create an ideal setting for entertaining or a quiet retreat.

18000 Overlook RD, Los Gatos

Listed by Donald Knight, 408-313-2191 from Coldwell Banker Realty
(If provided) CoList: Robin Sedgwick from Coldwell Banker Realty

Sold listing courtesy of Michael Roberts from CBR

16383 Aztec Ridge DR, Los Gatos
$5,250,000
6 Beds ⋅ 8 Baths ⋅ ML82017888 MLS
Set along one of Los Gatos most sought after ridge lines, this extraordinary estate captures sweeping yet intimate panoramas. Nearly every window frames views across downtown Los Gatos, Vasona Lake, the surrounding mountain ridges, and even the distant skylines of San Francisco, Oakland, and San Jose. Wrapped in privacy and framed by elegant landscaping, this breathtaking residence combines grandeur, comfort, and a deep connection to its natural setting. A tall wrought-iron entry door accented by mosaic glass opens to a grand foyer with volume ceilings and an elegant chandelier. Dual staircases sweep upward, creating balance and presence, while large windows allow natural light to pour in. Radiant heated marble and tile floors flow throughout the property for year-round comfort. The home unfolds with thoughtful flow and scale. With an expansive primary suite, four guest bedrooms, executive office, attached ADU with full kitchen and bath, detached pool house and two finished three-car garages, this estate is a home of scale, refinement, and enduring presence. With panoramic views dusk to dawn, an elegant design and resort-style amenities, it offers a true Los Gatos estate experience private, expansive, memorable, and a wonderful place to call home.

16383 Aztec Ridge DR, 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

Sold listing courtesy of Yan Tian from BOR

130 Sierra Azule, Los Gatos
$5,200,000
4 Beds ⋅ 4 Baths ⋅ ML82039123 MLS
Luxurious private executive estate, which sits atop a premiere ridge-top parcel and offers spellbinding panoramic Silicon Valley views. Immaculate attention to detail evident in all facets of this home; the yard, landscaping, and supporting systems are exquisite. Elegant traditional home featuring spacious formal living room and dining room, an executive office, a large ground-floor en suite, a grand entry and staircase, a huge chef's kitchen with top-rated appliances, butler's pantry/pantry. massive three-car garage, idyllic outdoor entertaining areas, ample flat lawn space for a pool or additional square footage, observation deck for delightful sunrises & coffee time, a huge sunlit raised garden, significant solar panel system with Tesla Powerwall backups. Home is supported by first-rate Los Gatos public schools. Only moments from town, Lunardi's, Peet's, Blossom Hill Elementary, and Highway 17/85 access, while offering the serenity of a mountaintop escape. Set among world-class hiking trails and neighboring estate properties, this hillside neighborhood embodies exceptional prestige, refined luxury, and elegance. Lovingly and meticulously maintained by original owner, this distinguished, well-appointed home is ready for next chapter for the fortunate new owner. Welcome home!

130 Sierra Azule, Los Gatos

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

Sold listing courtesy of Tracy Webb from CBR

board logoThe 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.


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