Hillside Real Estate, Homes, Condos for Sale in Monte Sereno, CA

6 Beds ⋅ 3 Baths ⋅ ML82056437 MLS

Beautiful tri-level home ideally situated at the end of a quiet cul-de-sac on an approximately 10,585 sq ft landscaped lot. Designed for comfortable everyday living and effortless entertaining, the private backyard features a sparkling pool, expansive deck, and low-maintenance landscaping, creating the perfect outdoor retreat. Inside, the light-filled contemporary floor plan offers an inviting blend of formal and casual living spaces, enhanced by a freshly painted exterior and interior with new carpeting. Sliding glass doors from the family room and informal dining area open seamlessly to the spacious deck for year-round dining and relaxation. The generous kitchen offers abundant counter space and overlooks the picturesque backyard. The spacious primary suite features an en suite bath and walk-in closet. Enjoy the best of downtown Los Gatos living, just one block from Bachman Park and moments from vibrant shops, acclaimed restaurants, the weekly farmers' market, and scenic hiking and biking trails. Convenient access to Highways 17 and award-winning Los Gatos schools complete this move-in-ready home, offering an exceptional combination of location, lifestyle, and indoor-outdoor living.

16342 Alexander AVE, Monte Sereno

Listed by C.T. Harris, 408-375-9265 from Christie's International Real Estate Sereno
(If provided) CoList: Kirsten Trapani from Christie's International Real Estate Sereno

$2,812,000

4 Beds ⋅ 4 Baths ⋅ ML82043910 MLS

Fabulous and immaculate home in desired Montalvo Oaks development. Built just 5 years ago with modern high-end fixtures and finishes. Premium gourmet kitchen with award winning Hestan appliances including 48" 5-burner gas range + griddle, u-line beverage center, Orinda style white cabinets, waterfall quartz counter-top, & pantry. The open concept floorplan is perfect for luxury living. Spacious primary suite has a large spa like bathroom with soaking tub, separate commode room and an oversized walk-in closet. Two additional bedrooms upstairs are both en-suites with walk-in closet. Versatile ground level bedroom is perfect for guests or as an office. Nice private paver patio for dining or entertaining. Additional features include a spacious upstairs laundry room with wash sink, custom electric window shades and nice built-in cabinetry throughout. Energy efficient upgrades include owned solar, tankless water heater and an EV charger. Ideally located almost halfway between downtown Los Gatos and Saratoga Village. Sought after Saratoga schools.

18867 Montalvo Oaks CIR, Monte Sereno

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

Sold listing courtesy of Nataliia Khimich from KWLGE

$6,150,000

5 Beds ⋅ 7 Baths ⋅ ML82040024 MLS

Elegant, comfortable and well-appointed Monte Sereno home with scenic views, beautiful backyard and just a few blocks to the heart of Downtown Los Gatos. Great floor plan with ground floor guest suite + library/office. All en suite bedrooms. Spacious, open-concept gourmet kitchen with large island, extensive cabinet space, walk-in pantry, butlers pantry and views of the backyard. Primary suite with hill views, natural light, huge walk-in closet, spa-like shower, large soaking tub and pass-through gas fireplace. 1-level guest house with high ceilings, kitchen, full bathroom, fireplace and Murphy bed with built-in cabinetry. Beautifully-landscaped property with drought-tolerant plants, mature roses, custom stonework and extensive patio space for family BBQs or entertaining on a grand scale. Room for a pool. Extensive driveway with pavers and 3-car garage. Pleasant cul-de-sac setting. Top-rated Los Gatos schools.

18211 Bancroft AVE, Monte Sereno

Listed by Erin Burke, 408-316-8369 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Theresa Wellman from HMWN

$5,000,000

5 Beds ⋅ 3 Baths ⋅ ML82036971 MLS

An extraordinary historic estate in Monte Sereno, where timeless architecture and preserved craftsmanship meet thoughtful modern updates. Spanning 3,802 sq ft, this 5 bedroom home includes a dedicated office and bonus room. The primary suite is on the main level, featuring a bathroom with a custom stained glass piece of lilies illuminated from outside. Upstairs offers three generous bedrooms and a huge den with the original pool table. Rich Craftsman-style woodwork, original picture rails, wavy glass, textured wallpaper, high ceilings, skylights, and two fireplaces showcase the homes historic charm. The large kitchen has abundant cabinetry, granite countertops, gas cooktop, double oven, and dishwasher. Set on 28,345 sq ft, the grounds feature a large driveway, 3-car garage with EV charger, expansive backyard with scenic views, play area, tree house, fruit trees, front and enclosed porches, and a huge basement with storage. A framed newspaper article highlights the homes history. This estate may qualify for Mills Act tax benefits. This is more than a home. It is a piece of Monte Sereno history. A truly rare opportunity to own a property defined by original architecture, enduring character, and timeless beauty. Award-winning schools!

16202 Serena Vista CT, Monte Sereno

Listed by Michael Galli, 650-800-1980 from Compass
(If provided) CoList: from

Sold listing courtesy of Joe Piazza from CBR

$4,200,000

4 Beds ⋅ 4 Baths ⋅ ML82038157 MLS

Major $500K adjustment from the original list price. A rare Monte Sereno hillside property on prestigious Withey Road, offering one of the South Bays best views of the Valley, with sweeping city-light, garden, and vineyard outlooks. The elevated setting creates the dramatic outlook, peaceful separation, and tucked-away feel while still being only a 4-min drive to vibrant downtown Los Gatos. The property offers privacy, charm, and rare seclusion in one of the areas most exclusive enclaves. The elegant two-story residence is move-in ready and filled with natural light through high ceilings, large windows, and skylights. The very spacious kitchen offers abundant cabinetry and opens to the main living areas and a large deck. 2 fireplaces, a private primary balcony, large walk-in closet, and second ensuite with stunning hillside views. Outdoor has a flat lawn area, detached wine house with running water & electricity, small vineyard, mature landscaping, and 8 private parking spaces exclusive to this residence. Large rear-yard access provides flexibility for a potential ADU with separate entrance, plus opportunity to expand usable grounds from the vineyard or lawn. A remodeled bathroom, new dual HVAC systems, and Tesla EV charger. Saratoga Unified Schools, Highways 85 and 17.

18782 Withey RD, Monte Sereno

Listed by Spencer Hsu, 408-223-5493 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Mike Masoumi from REMAX

$3,927,986

4 Beds ⋅ 5 Baths ⋅ ML82037329 MLS

Set on an expansive 12,517 sq ft flat lot, this beautiful traditional residence offers exceptional space & functionality in a desirable location near Bachman Park & just moments from downtown dining, shopping, and community amenities. A gated entry leads to a charming brick courtyard with a tranquil koi pond & serene zen garden, creating a welcoming approach to the home. The well-designed floor plan features formal living room with French doors opening to the garden, formal dining room with bay window, & an inviting separate family room. The spacious kitchen includes a garden window overlooking the backyard, SS appliances, & generous breakfast nook with access to the rear patio. A dedicated office with built-in workstation & powder room provides an ideal work-from-home space. The main level includes a large primary suite with walk-in closet, plus second en-suite bedroom for flexible guest accommodations. Upstairs features new carpeting, an expansive bonus space, 2 bedrooms, & 2 full baths. Additional highlights include dual-pane windows, Nest thermostat, dedicated laundry room, and a 2-car garage plus 1-car covered carport with workshop area & cabinetry. The expansive backyard & patio offer excellent space for outdoor entertaining, everyday enjoyment, and incredible potential.

16345 Alexander AVE, Monte Sereno

Listed by Ducky Grabill, 408-761-4073 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Eric McCafferty from GGSIR

$6,500,000

5 Beds ⋅ 4 Baths ⋅ ML82019861 MLS

Nestled within one of the most coveted neighborhoods, this sensational property offers an unparalleled lifestyle on a rare, flat, and expansive acre+ parcel. Prepare to be captivated by the prolific gardens and the allure of your own regulation-sized tennis court that can accommodate pickleball, and basketball as well, providing a wide range of recreational options for sports enthusiasts.Discover large, light-filled entertaining rooms graced with gorgeous hardwood floors. The living & dining rooms provide sophisticated spaces for gatherings, complete with a convenient wine and china closet. For those who work from home or desire a quiet retreat, a sumptuous office/den is conveniently located on the main level. The expansive kitchen offers multiple workspaces, a practical butler's pantry, & ample storage. Enjoy preparing meals while overlooking the breathtaking back gardens and taking in the picturesque views of the south mountains and stunning sunrises. The primary suite, a true oasis featuring a cozy fireplace, a private balcony to savor the views, a generous walk-in closet, and a huge bathroom. Pamper yourself with his/her sink areas, a large shower, and an oversized tub. A 2nd bedroom suite provides comfort and privacy with a walk-in closet and an elegant bathroom.

16000 Greenwood RD, Monte Sereno

Listed by Dana & Cyndi, 408-621-4855 from Compass
(If provided) CoList: from

Sold listing courtesy of Malav Patel from COMPS

$2,750,000

2 Beds ⋅ 2 Baths ⋅ ML82015481 MLS

Nestled in the heart of Monte Sereno, this 2-bedroom/ 2 bathroom residence offers comfort with incredible views in a highly desirable setting. Wood accents throughout the living room evoke an organic feel, while vaulted ceilings with exposed beams add architectural charm. Oversized windows bathe the home in natural light, seamlessly connecting the indoors to the surroundings. The open dining room is perfect for hosting, conveniently located next to a fully equipped kitchen featuring mosaic tile accents and ample prep space. A second living area invites relaxation and entertainment alike, complete with a cozy fireplace and direct access to the patio. The expansive backyard provides an ideal space for weekend gatherings or quiet evenings beneath the stars. This home provides a blank canvas allowing you to create your own masterpiece. Located in one of Silicon Valley's most sought-after communities, this home offers a peaceful lifestyle with easy access to top-rated schools and downtown Los Gatos.

18711 Withey RD, Monte Sereno

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

Sold listing courtesy of Brandon Gummow from SGP

$2,680,000

3 Beds ⋅ 3 Baths ⋅ ML82015478 MLS ⋅ Montalvo Oaks BLDG.

Montalvo Oaks! Four Year New homes in Monte Sereno built by SummerHill Homes! Featuring an open concept living/dining/kitchen with fenced in private outdoor patio, & desirable corner location! Chef's kitchen with high end stainless steel Hestan appliances, gas range, beverage refrigerator, white shaker cabinets, quartz counter tops. upgraded lighting package throughout, Nest package, upgraded plumbing finishes, electric shades throughout, upgraded horizontal metal stair rail with wall mounted stair lights, wood and tile floors, A/C, solar (owned) with EV charger! Expansive owner's suite with a spa like bathroom, large walk in closet with high quality closet organizer, large laundry room with sink on second floor & ample guest parking! Offering highly ranked Saratoga schools, near downtown Los Gatos, Saratoga Village, easy commute access to 17/880! You won't want to miss out on this one!

18855 Montalvo Oaks CIR, Monte Sereno

Listed by Joe N. Pollifrone, 408-460-5469 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Warren Ma from FRAME

$2,667,000

4 Beds ⋅ 2 Baths ⋅ ML82004988 MLS

Price Reduced $100,000. Tucked away in a peaceful Monte Sereno cul-de-sac, this Frank Lloyd Wright-inspired home blends timeless architecture with natural serenity. Ideally located with a walking path to downtown Los Gatos and just moments from Bachman Park, this 4-bedroom, 2-bathroom residence sits on nearly half an acre and offers 2,436 sq ft of thoughtfully designed living space. Enjoy a unique reverse floor plan featuring the primary bedroom on the main level and three additional bedrooms downstairs, optimizing privacy and views. Floor-to-ceiling windows frame sweeping vistas and a tranquil backyard stream. Rich tongue-and-groove heart redwood paneling and custom details throughout reflect the craftsmanship of the original owner-builder. Located in the highly acclaimed Los Gatos School District, this rare offering combines architectural inspiration, nature, and convenience in one of the area's most sought-after neighborhoods. A tremendous opportunity to gain access to this school district and neighborhood, which is just minutes from downtown. This home is often compared to the Eichler/Mid-Century Modern style, with plenty of room to add on, expand, fix up, and improve... or move in and enjoy today. Visit and see for yourself what a special secret this home is.

16310 Oakhurst DR, Monte Sereno

Listed by Kirsten Trapani, 408-761-0686 from Christie's International Real Estate Sereno
(If provided) CoList: Barton Call from Christie's International Real Estate Sereno

Sold listing courtesy of Michael Riese from CBR