Monte Sereno Multi-Generational Homes for Sale

5 Beds ⋅ 9 Baths ⋅ ML82025383 MLS ⋅ Loma Serena BLDG.

Welcome to 15288 Via Pinto, a custom transitional ranch completed in 2021. Designed by Gary Schloh and crafted by Parden Construction, this modern Monte Sereno masterpiece offers approximately 8,328 square feet of refined living on nearly half an acre. A dramatic foyer introduces sun-filled formal living and dining areas with soaring ceilings, exquisite finishes, and an effortless sense of scale. The chefs kitchen is a showpiece, featuring a grand island, premium appliances, and a walk-in pantry that flows seamlessly into the family room and outdoor entertaining spaces. Five ensuite bedrooms include a luxurious primary retreat with a custom walk-in closet and spa-inspired bath with a soaking tub beneath a skylight. A private office, elevator, and lower-level entertainment wing offer exceptional flexibility, complete with a media room, wet bar, wine cellar, gym with sauna, and guest suite. The six-car garage with dual lifts, 800-amp service, and multiple EV chargers will captivate any automotive enthusiast. This property is located within the prestigious Loma Serena neighborhood, where residents enjoy more than 44 acres of private open space, scenic trails, and exclusive equestrian facilities.

15288 Via Pinto, Monte Sereno

Listed by Dan Pfister, 408-836-6084 from Milestone Real Estate Services
(If provided) CoList: Maria De La Luz Pfister from Milestone Real Estate Services

Sold listing courtesy of Jessie Li from NTERO

$9,500,000

5 Beds ⋅ 7 Baths ⋅ ML82035731 MLS

This spectacular Monte Sereno estate showcases exquisite architecture, curated landscape, and exceptional craftsmanship, embodying timeless French Country elegance. Set on more than 30,000sqft, the residence was comprehensively reimagined during an extensive 2020-2022 renovation, preserving romantic architectural character while elevating every system and finish. A decorative brick wall, iron gates, sweeping lawn, and mature trees create a storybook arrival. Inside, ten-foot ceilings, bespoke millwork and wide-plank oak floors introduce refined living spaces designed for both everyday comfort and elegant entertaining. The kitchen stands as a culinary showpiece with a LaCanche range, honed quartzite surfaces, mosaic stone backsplash, and a large island with seating for eight. Five ensuite bedrooms and executive office span two levels, including two main-level suites ideal for guests or multigenerational living. The primary suite enjoys a fireplace, private balcony, and spa-inspired bath with radiant heated marble floors and a freestanding tub. A separate pool house with kitchen, living area, two bedrooms, and sauna adds remarkable flexibility. Expansive grounds surround the pool, spa, and outdoor kitchen beneath a beautiful loggia, creating an inviting setting for outdoor living.

17930 Vineland AVE, Monte Sereno

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

Sold listing courtesy of Kiersten Ligeti from AGNC

$6,800,000

7 Beds ⋅ 10 Baths ⋅ ML82019938 MLS

Experience elevated living in this extraordinary new construction located in the heart of highly sought-after Monte Sereno. Thoughtfully designed with timeless elegance and modern sophistication, this expansive home features a seamless open floor plan, soaring ceilings, and exquisite custom cabinetry that rises to the ceiling, adding a sense of refined grandeur throughout. With 7 bedrooms, 8 full bathrooms, and 2 half bathrooms, this dream residence includes a luxurious primary suite, private gym, sauna, elevator, and a beautifully integrated attached ADUperfect for guests or multigenerational living. The spacious entertainment room with a stylish wet bar sets the stage for unforgettable gatherings, while every detail has been meticulously crafted for comfort, style, and function. Ideally located in a prestigious Monte Sereno neighborhood served by top-rated Los Gatos schools, this home offers unmatched convenience to shopping, dining, and major commute routes. A rare opportunity to own a brand-new masterpiece in one of Silicon Valleys most coveted communities.

16108 Mays AVE, Monte Sereno

Listed by Estila Raissi, 408-316-8899 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Pauline David from NTERO

$4,400,000

4 Beds ⋅ 5 Baths ⋅ ML81999441 MLS

Nestled in the heart of the coveted Twin Creeks neighborhood of Monte Sereno, this extraordinary estate on a private 1.07 acre parcel strikes the perfect chord between elegance, functionality & potential. Sweeping spiral staircase & crystal chandelier set the tone for a grand experience. W/4 bedrooms 4.5 bathrooms & 5,085sf of living space. Music room & arts/crafts room can be transformed into bedrooms, bringing total of a possible 6 bedrooms. Formal dining room & living room w/wood burning fireplace. Family room w/surround sound, projector w/drop down screen, & remote blackout shades perfect for movie nights. Master suite w/walkin closet/dressing room, dual vanities, separate shower & tub. 3 additional well-appointed bedrooms, office, & many closets/storage areas. Huge Music room w/full bathroom & separate entrance, can transform to a private teaching studio or Aupair suite. Add kitchen in hobby area for even more versatility! Covered patio, fire pit, & pool/spa make entertaining a breeze. Cabana plumbed for electricity/water, perfect for relaxing in the shade. 1+ acre lot w/seasonal creek & plenty of room to add tennis/pickleball/sports court or anything else you desire. Located in one of the most sought-after neighborhoods in the Bay Area w/award-winning Los Gatos schools.

15374 Tamson CT, Monte Sereno

Listed by Travis R. Bertelsen, 408-335-1469 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Lili Song from COMPS

$8,350,000

5 Beds ⋅ 7 Baths ⋅ ML81992590 MLS

SPECTACULAR CUSTOM FRENCH CHATEAU ESTATE IN PRIME AREA OF MONTE SERENO WITH STUNNING VIEWS OF THE CITY AND MOUNTAINS! TOP OF THE LINE QUALITY CONSTRUCTION! TOP RATED SCHOOLS! WALK TO DAVE'S ELEMENTARY! VERY PRIVATE LOCATION AMONGST HIGH END ESTATES! ONLY 6 MINUTES TO TOWN. HOME FEATURES 6037 SQUARE FEET WHICH INCLUDES 300 SQ FT OFFICE/GYM! 5 BEDROOMS WITH TWO PRIMARYS, ONE ON THE MAIN FLOOR AND ONE UPSTAIRS. GRAND ENTRY WITH SOARING CEILINGS AND BEAUTIFUL SPIRAL STAIRCASE! LARGE SEPARATE DINING ROOM, LIBRARY/MUSIC ROOM OFF LARGE SEPARATE LIVING ROOM BOTH WITH BEAUTIFUL FIREPLACES. GOURMET KITCH WITH CUSTOM CABINETRY, FULL SLABS, PANTRY AND TOP OF THE LINE APPLIANCES. LARGE BREAKFAST ROOM AND ADJACENT FAMILY ROOM WITH FIREPLACE AND FULL ENTERTAINMENT CENTER. WINE CELLAR, THEATRE, STEAM SHOWER! UPSTAIRS UTILITY ROOM! STUNNING BACKYARD WITH LARGE COVERED OUTDOOR KITCHEN AND BARBECUE, BATHROOM AND OFFICE/GYM. BEAUTIFUL IN GROUND POOL AND SPA AS YOU RELAX AND ENJOY CITY AND MOUNTAIN VIEWS! 4 CAR GARAGE WITH 240 EV CHARGER

18232 Daves AVE, Monte Sereno

Listed by John Faylor, 408-605-8133 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Nicole Emanuel from CBR

$5,361,000

5 Beds ⋅ 5 Baths ⋅ ML81992143 MLS

A true masterpiece of modern California living, this stunning 5-bed, 4.5-bath home was rebuilt in 2025. Spanning 3,554 sq. ft. on a 12,155 sq. ft. lot, it blends luxury, style, and functionality with seamless indoor-outdoor living. Soaring ceilings, abundant natural light, and impeccable craftsmanship greet you upon entry. The chef's kitchen boasts top-tier Thermador appliances, a wine column fridge, custom white oak cabinetry, and an oversized pantry. Each en-suite bedroom offers spa-like baths and walk-in closets, while the primary suite is a true sanctuary, opening to the backyard through sleek folding doors. Designed for entertaining, this home features seven skylights, four folding patio doors leading to a sprawling deck, a gas fireplace, and a built-in speaker system. The indoor laundry room includes two washers and dryers for effortless living. An oversized driveway provides ample parking for guests. Located in the award-winning Los Gatos School District, this exceptional home offers modern amenities just minutes from Downtown Los Gatos.

18080 Arlee DR, Monte Sereno

Listed by Christina Khosrowabadi, 408-318-4863 from Redefine Real Estate
(If provided) CoList: from

Sold listing courtesy of JJ JJ Team:Jones/Cassel from NTERO

$5,960,000

5 Beds ⋅ 5 Baths ⋅ ML81973243 MLS

Sprawling, single-story estate in pristine Monte Sereno location! Superior quality, timeless charm & thoughtful floor plan enjoys volume ceilings & generous picture windows-views of pristine gardens & lg entertaining spaces & beyond on mostly level lot. Welcoming front porch opens to fantastic great room w/ formal dining area anchored by handsome fireplace. Wall of windows offering spectacular views & multiple sliders for exterior access-ultimate indoor/outdoor living experience. Gourmet kitchen ready for culinary enthusiast- large center island w/ sink, prof grade appliances, dining nook. Expansive family rm, attached game rm & private ensuite bedroom. Right wing w/ primary suite w/ attached retreat, lg walk-in closet & dressing area. Spa-inspired bath w/ soaking tub, separate steam shower. 3 additional bedrooms share generous hall bath. Walk out lower level of 500+ sqft, used as office w/ built-in desk, full bath & private entrance. Meticulously landscaped, park-like grounds are built to enjoy! Meandering stone paths pass thru landscape w/ ample open space, generous lawns & open areas. Small redwood grove shades dry creek bed. Premier quiet location w/ easy access to Hwy 9, 85 & 17. Exceptional opportunity - Close to dwntwn LG & Saratoga Village- plus top-rated LG Schools!

18242 Seebree LN, Monte Sereno

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

Sold listing courtesy of Arti Miglani from APR

$3,750,000

5 Beds ⋅ 6 Baths ⋅ ML81969163 MLS

IMMACULATE LUXURY HOME IN PRIVATE COMMUNITY | Built in 2022 by SummerHill Homes, this Monte Sereno residence is exquisitely maintained, securely tucked inside a private residential pocket between the downtown districts of Saratoga and Los Gatos. Step into a highly livable floorplan with freeflowing living, dining, and kitchen spaces that open to a private patio retreat. Upscale kitchen amenities include waterfall quartz countertops, premier appliances, Orinda cabinets, and walk-in pantry. All ensuite bedrooms include ground-level guest quarters. An expansive walk-in closet and spa bath with soaking tub and curbless walk-in shower augment the primary suite. Details include high ceilings, wideplank wood floors, EV wiring, owned solar panels, and contemporary finishes throughout. Near downtown destinations, scenic hiking, and acclaimed Saratoga schools (buyer to verify).

18828 Montalvo Oaks CIR, Monte Sereno

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

Sold listing courtesy of Bill Gorman from CBR

$5,400,000

4 Beds ⋅ 4 Baths ⋅ ML81962756 MLS ⋅ Loma Serena BLDG.

Beautiful single story home on large flat lot in popular Loma Serena neighborhood of Monte Sereno! Spacious rooms, large picture windows showcase lovely views of surrounding foothills & beyond. Mature landscaping of variegated & flowering bushes & trees create relaxing, peaceful retreat. Sparkling hardwood floors flow through generous living areas. Recently remodeled, thoughtful interior provides ample space for entertaining. Generous living room & formal dining area overlook front landscape. Large kitchen w/ ample cabinetry, center island w/ seating opens to expansive family room w/ views of rear landscape. Four bedrooms on left wing, gorgeous primary bedroom w/ spa inspired bath and 3 additional bedrooms including another en-suite and separate office. Rear yard is built for enjoyment! Large slate patio, covered outdoor loggia w/ built-in kitchen. Large counter bar for casual dining, relax under the covered loggia watching a game on the outdoor TV. Generous lush lawn surrounded by garden trees & flowing shrubs. Expansive side yard w/ extra storage. Enjoy 42 acres of open space & trails for the exclusive use of homeowners of association. Top Los Gatos schools! Easy commute w/ convenient access to Hwy 85 & 880.

15400 Via Palomino, Monte Sereno

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

Sold listing courtesy of Maria Finkle from CARRC

$12,100,000

7 Beds ⋅ 9 Baths ⋅ ML81958606 MLS

French provincial-inspired masterpiece is the dream home for the most discerning buyer. This home has a commanding presence while driving through arguably the most prestigious neighborhood of Monte Sereno. Built on the top of a knoll overlooking the newly planted vineyard, the home has views of the lush mountains and postcard sunsets. The 1.1 acre knoll gives the house a regal feel and has a huge, flat, fully landscaped backyard with room for a sports court or the largest garden. Built by renowned builder Mason Hammer, with impeccable craftsmanship, design, and artistry. An entertainers delight with at least 8 outdoor patio areas for the grandest parties. Main house is approximately 8215 sf (3365 sf on the first floor, 2185sf on the second floor and 2665sf basement) Additional 593sf ADU, 4-car, 900+/- sf of garage space. Plus over 3000sf of outdoor patio and balconies. A grand total of over 10708+/-sf of new construction.) 6 bdrms, Office,8 full baths plus one half bath. Two, 2-car garages. epoxy floors, electric car chargers. Luxurious kitchen with 2 islands, 8 burner 48 gas stove, double ovens, 2 sinks, Dacor refrig/freezer, 2 dishwashers, steam oven, plus a fully equipped caterer's kitchen! Theatre room, gym, solar panels, wine room, 2 laundries, this mansion has it all!

16005 Greenwood LN, Monte Sereno

Listed by Anita Hunter, 408-930-1265 from Compass
(If provided) CoList: from Compass

Sold listing courtesy of Purush Viswanathan from LNKSV

$8,200,000

6 Beds ⋅ 8 Baths ⋅ ML81957105 MLS

This is a truly a once in a lifetime opportunity. A home of this scale and grandeur is a rare jewel located in the prestigious Town of Monte Sereno. A life of leisure awaits you in this Mediterranean Villa nestled between Los Gatos & Saratoga. From the grand foyer to the remarkable, unique design elements blend w/ sophisticated, high-end finishes. Limestone & hardwood stretch across the floors, crown molding, & beamed ceilings extend overhead. Pass by the lavish formal living spaces to arrive at the impressive great room or head down the hall to the primary suite complete w/ a home office. Throughout the house, French doors connect the spacious interior to the expansive lot. Loggias, stone patios, & flourishing gardens encompass the estate, as a pool/spa, BBQ, fireplace, a volleyball court, bocce ball & a vineyard create a resort-like atmosphere. A Guinness created Pub, & a wine cellar grace the lower level. This home is a once in lifetime opportunity on fully landscaped flat 1.5 flat acres with everything you could ever desire. Perfect for a wonderful family night or grand entertaining. This special home has everything you can dream!

15121 Becky LN, Monte Sereno

Listed by George Montanari, 408-497-2213 from Compass
(If provided) CoList: from

Sold listing courtesy of Betty Chen from GNVR

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