luxury houses with pool for sale Hillsborough, United States

A rare mid-century retreat with sweeping bay and mountain views is offered for the first time in over 45 years. This well-maintained 4BR/2BA home sits on an expansive 24,000 sq ft lot at the end of a quiet cul-de-sac in one of San Mateo's most desirable Hillside neighborhoods. Enjoy panoramic views of San Francisco, the Peninsula, and the East Bay. The home blends classic mid-century character with a functional, inviting layout. Sunlit living spaces feature all new double-paned windows, hardwood floors, and a fireplace, complementing a formal dining area ideal for gatherings. The updated kitchen offers generous counter space, ample storage, and new appliances. Four well-sized bedrooms and two full baths provide flexibility for living, guests, or a home office. A dedicated laundry room adds convenience. The oversized lot offers a rare sense of privacy and openness. The peaceful secluded backyard features a pool and areas for entertaining and offers a calm space to recharge with daily opportunities for wildlife viewing! Located near Laurelwood Park and Sugarloaf Open Space, with access to hiking trails, top-rated schools, shopping, dining and easy access to Hwy 92. A unique opportunity to own a classic mid-century home with exceptional space, privacy, and views in a sought-after San Mateo location.

Vacant, easy to show. Seller complete disclosures to be posted shortly

Bucket list property alert! Flat, lush grass right off of the kitchen overlooking world class views of the San Francisco Bay, Bridges, and City Lights from San Francisco on down the Peninsula and across to the eastern mountains. This view property is flanked by an expansive lawn on one side and a gorgeous pool and spa on the other. Still more views of the green canyon frame your entrance to this rare property. Your majestic and uplifting arrival home on the daily is ready now, you could be living here before the Holiday season. Freshly remodeled, across the street from from the local Belmont trail system including Water Dog Park and Hidden Canyon, you can venture into the parks and trails from your front door and still enjoy all the downtown amenities just a few moments away in both Belmont and San Carlos. A short commute to the entire bay area with painless access to Highways 280 and 92. Hilltop living without the downsides, abundant living space with six bedrooms plus an office, vau

Charming 3BR/2BA home with pool in Redwood City's desirable Roosevelt neighborhood. This 1,440 sq ft residence on a 5,880 sq ft lot offers classic character and a flexible layout. The main level features a comfortable living room with fireplace, dining area, and a galley kitchen with vintage charm, dining area overlooking the backyard pool, plus two comfortable bedrooms and a full bath. The private primary suite upstairs provides a peaceful retreat with separation from the main level. Outdoor living is a highlight, enjoy the swimming pool, multiple spaces for entertaining, and a welcoming covered front porch. An attached garage and fenced yard add convenience. Ideally located near Red Morton Park, a community hub with year-round activities, playgrounds, and sports facilities, as well as the beloved Schaberg Library. Close to local shops, eateries, and downtown Redwood City with easy access to commute routes. Stanford, Downtown Menlo Park, Palo Alto, Apple Park & San Francisco International all 10-30 minutes nearby. 754 Topaz St, a wonderful opportunity in an amenity-rich, community-oriented neighborhood.

Charming 3BR/2BA home with pool in Redwood City's desirable Roosevelt neighborhood. This 1,440 sq ft residence on a 5,880 sq ft lot offers classic character and a flexible layout. The main level features a comfortable living room with fireplace, dining area, and a galley kitchen with vintage charm, dining area overlooking the backyard pool, plus two comfortable bedrooms and a full bath. The private primary suite upstairs provides a peaceful retreat with separation from the main level. Outdoor living is a highlight, enjoy the swimming pool, multiple spaces for entertaining, and a welcoming covered front porch. An attached garage and fenced yard add convenience. Ideally located near Red Morton Park, a community hub with year-round activities, playgrounds, and sports facilities, as well as the beloved Schaberg Library. Close to local shops, eateries, and downtown Redwood City with easy access to commute routes. Stanford, Downtown Menlo Park, Palo Alto, Apple Park & San Francisco International all 10-30 minutes nearby. 754 Topaz St, a wonderful opportunity in an amenity-rich, community-oriented neighborhood.

Nestled on a quiet, beautifully wooded lot in desirable Woodside Hills, this meticulously updated residence blends timeless elegance with modern comfort. Light-filled interiors showcase expansive windows, refined finishes, custom window coverings and seamless indoor-outdoor flow. The remodeled chef's kitchen (2019) features a quartz-topped island, custom cabinetry, and premium Thermador, Bosch, and LG appliances, while opening to inviting dining and family spaces. A gracious living room with a redesigned gas fireplace and access to a deck creates an ideal setting for entertaining. Up the grand staircase, a serene primary suite offers high ceilings, dual walk-in closets, and a spa-inspired bath with soaking tub, curb-less shower, and designer finishes. Two additional bedrooms enjoy natural light and peaceful views. Extensively renovated, the backyard presents a resort-like retreat with multiple entertaining areas, a saltwater pool, AZEK decking, stamped concrete patios, gazebo and stone retaining walls and box planters, all surrounded by majestic oaks. Smart home features throughout the home include an EV charger. This exceptional home is situated in a premier, ultra-private location while being close to the Town of Woodside, Redwood City, schools, shopping, dining and Hwy 280.

Set on beautifully landscaped grounds with sweeping Bay views, this impeccably maintained Woodside residence offers a rare blend of privacy, scale, and resort inspired living. Thoughtfully designed to balance formal and casual living, the home features a gracious entry introducing light filled interiors with high ceilings, refined millwork, and an elegant flow throughout. The living and dining rooms offer defined spaces for entertaining, while the well appointed kitchen with custom cabinetry, stone countertops, and a central island anchors the homes gathering spaces and opens to the adjacent family room. The family room connects seamlessly to the outdoors, extending daily living into the surrounding landscape. The primary suite is a private retreat with generous proportions, a view deck, and a spa like bath. Three additional bedrooms provide flexibility for guests, office, or extended living. Designed for everyday living and entertaining, the grounds offer expansive patios, a pool, and a covered lounge area. Multiple vantage points capture natural beauty and Bay views, creating a sense of tranquility throughout. Now thoughtfully repositioned for todays market, offering a timely opportunity to secure a premier Woodside residence with convenient access to Peninsula amenities.

Outstanding development opportunity in Redwood City on over half an acre. Includes two parcels: 2139 Alameda De Las Pulgas (13,163) and the vacant lot next door 069-291-460 (14,917) for a combined total square footage of 28,080. Parcels to be sold together. Many multi-million dollar homes sold in the neighborhood. Well maintained existing home on property with pool.

A modern masterpiece, striking high end new construction in highly sought after West Atherton location. Stunning modern design and exceptional craftsmanship define this just completed new home set on an expansive, resort like grounds of roughly one acre. Clean architectural lines, white oak floors & designer lighting create a sophisticated ambiance across two levels. Main home has 6 bedrooms, 6.5 baths, 2 offices, including flex gym space & ideal guest quarters. Formal living & dining rooms set the stage for refined entertaining,while the kitchen & family room unfold beneath soaring ceilings & retractable glass walls opening to rear grounds. Taj Mahal countertops, premium appliances & custom cabinetry anchor the chefs kitchen. A recreation and media room with wine cellar & wine bar extends seamlessly through a disappearing wall of glass to the pool, spa, & heated cabana with outdoor kitchen. Upstairs, a skylit lounge area gives way to the luxurious primary suite and three additional bedroom suites.A 5th bedroom upstairs can also be used as a gym or flexible space.Detached 2-bedroom guest house w/full kitchen adds exceptional versatility.Solar, home automation,attached 3-car garage with EV charging complete this extraordinary offering in this prime West Atherton setting.

Grand Lindenwood estate in one of Athertons most sought-after neighborhoods. This extraordinary three-level residence, exceptional craftsmanship, refined finishes, and resort-caliber amenities throughout. Elegant interiors feature radiant-heated stone floors, Venetian plaster walls, Italian windows and doors, new wool carpet. Designed for grand-scale entertaining and comfortable living, offering formal and casual spaces, including a beautifully remodeled chefs kitchen with handcrafted cabinetry, center island, professional-grade appliances, dumbwaiter and butlers pantry. The adjoining family room opens seamlessly to the outdoor terrace and pool. The luxurious primary suite is complemented by customized dual walk-in closets and a spa-inspired bath. Connected by sweeping staircase and elevator, the home includes 5 main level ensuite bedrooms including the primary. The lower level includes recreation and wellness, featuring theater, fitness center, spa with jacuzzi, sauna and steam, recreation room, and a wine cellar. The spectacular grounds offer vast lawns, mature trees, orchard, heated saltwater pool and spa, outdoor kitchen, and pool house. Advanced home automation, commercial grade electrical panel, security, distributed audio, programmable lighting and more. Excellent schools.

Rarely available estate, located in the highly sought-after Westridge neighborhood of Portola Valley. This lovely home is set on 3.86 serene acres w/ majestic oaks and offers a panoramic view of the SF Bay from Stanford to Mount Diablo. Enjoy a picturesque vista from the main home and newly built, stunning ADU. A gated driveway escorts you to a light-filled home highlighted by an open concept floorplan with high beamed ceilings and a wall of sliding doors to an expansive deck for al fresco dining and entertaining. Enjoy peaceful days and quiet nights filled with sparkling lights from the bay. The main home, containing 5bd/ 5ba, private office, family room and den one primarily one-story. The 1bd/1ba ADU has a spectacular deck with views too! Adding to the appeal is the sprawling grounds including a resort-like pool, hot tub, fire pit, gazebo, greenhouse, chicken coop and 2 fenced dog runs. Family/friends can gather throughout the exquisite property at numerous quaint outposts. This home is ideal for entertaining. Easy access to 280, Stanford University, Westridge hiking trails, shops and restaurants. Just 1.5 miles to the Ladera Shopping center, a 5-minute drive to Interstate 280, and access to top-ranked Portola Valley schools (buyer to verify eligibility)

TRI-LEVEL ESTATE OFFERS POOL HOUSE, 3+ ACRES Transport yourself to the East Coast in this incomparable custom estate. Gated acreage framed by California oaks reveals an exquisite Shingle-style home surrounded by bridges, enchanting gardens, a three-car garage, and fully functional pool house with pool and spa. Faced by a circular gravel drive, the tri-level main residence built in 2010 has been wonderfully maintained, boasting all ensuite bedrooms, a study, gym, and media lounge with full bar. Enjoy a sensational master chefs kitchen, ultra-luxurious primary suite, multiple fireplaces, surround sound, and ground-level guest/au pair quarters. Superb details include graceful turrets, round windows, soaring ceilings, gorgeous hardwood floors, and extensive millwork throughout. Outdoor retreats abound with amenities like a barbecue island, fireplace, paver terraces, wisteria-laden pergola, raised beds, and more. Moments from shopping, dining, trails, and breathtaking scenery, this piece of bucolic paradise is nestled near tech and venture capital centers, and only ~ 30 minutes from SFO and SJC. Excellent Portola Valley Schools. Property is on sewer giving a buyer full use of the lot. Main residence 5861 sq ft, guest house 732 sq ft=6593 sq ft Plus 888 sq ft garage.

With five bedrooms, four bathrooms, this home has space and options. The 1.14± acre gated property enjoys level lawn, pool and mature privacy trees. The home is welcoming. They say the kitchen is the heart of the home and this space embodies that. Amenities include quality appliances and extras: six-burner Wolf range, two ovens, microwave and warming drawers, two dishwashers – one for dishes, one for pots and pans. Exceptional storage with pull-out shelving, custom corner cabinets and an appliance lift. The island provides workspace and seating. An adjacent family room has light, a fireplace, and access to the large deck. French doors open to incorporate the formal dining/living rooms into this space. Beamed ceilings, a fireplace, hardwood floors, a wall of windows and doors allow you to access the deck, to enjoy the view and host large gatherings. With a private entry a flexible, bookshelf-lined space could be an office, au pair or guest suite. There are two primary suites: three additional bedrooms plus an office. The upper-level has the second primary and includes a bonus room for an office/nursery/or workout space. There is a bedroom off the family room (ideal for guests). Great Portola Valley location: close to local shopping, Alpine Hills Swim & Tennis club, The Alpine Inn, excellent Portola Valley schools, and just four minutes to Highway 280.

Perched on a knolltop within prestigious Blue Oaks, this luxurious estate epitomizes elegance and exclusivity. Set on 2.53 acres of naturally organic beauty, this residence offers unparalleled privacy and breathtaking views of the San Francisco Bay. A true sanctuary, the home seamlessly blends sophisticated design with the tranquility of its natural surroundings. The expansive living room, bathed in natural light from floor-to-ceiling windows, provides a stunning backdrop of the sweeping Bay views. The heart of the home is the gourmet kitchen, a culinary enthusiast's dream, that opens to a spacious family room, creating a true great room that is ideal for both everyday living and entertaining. Multiple adjacent terraces offer 360-degree views. Each of the 5 bedrooms is an en suite retreat. The primary suite offers a luxurious spa-like bath, walk-in closet, fireplace and picture windows that capture the serene vistas. In addition to an executive home office, the estate boasts a home gym, media/rec room, wine cellar, expansive swimming pool and 4-car garage. This estate in Blue Oaks is more than a home; it is a lifestyle. With its unmatched privacy, luxurious amenities and awe-inspiring views, it offers a unique opportunity to experience the pinnacle of Silicon Valley living.

Completed in 2006, this magnificent vineyard estate is the perfect place to escape from the fast daily pace of Silicon Valley. The approximately 41 acres are as peaceful as they are beautiful, with spectacular top-of-the-world San Francisco Bay views. Arriving on the front terrace is as if stepping into the Italian countryside. The scale of the home is destined for grand entertaining spilling out to exceptional front and rear terraces. The kitchen is a culinary retreat with commercial-quality appliances, and the wine cellar awaits a sizable collection. Multiple rooms for everyday living, a theatre, plus a well-being center with spa, steam, and sauna add luxurious touches. Both 5660 Alpine Road and APN 080-040-120 are being offered for sale together.

Contemporary masterpiece with two-story guest house, pool pavilion, plus pool and spa on just over one acre of manicured gated grounds. Exotic woods of curly maple, pear, and Sapele mahogany complement maple and Halila limestone floors and counters in Brazilian granite and limestone. Graceful curves adorn walls, ceilings, windows, and cabinetry that maximizes storage. Five bedrooms and six and one half baths, library, lounge, full bar, nine-seat theatre, 2,000 bottle wine cellar, fitness center with steam & sauna, plus two offices one with secret Orient Express train car room with overhead train track that runs through both rooms. The guest house is designed in a Japanese teahouse style and the pavilion has a full kitchen for poolside entertaining. Meticulously landscaped grounds have many water features including streams, ponds, and waterfalls. Behind the scenes is home automation, security, whole-home backup generator, radiant heat & EV charging in the five car garage. Desirable cul-de-sac and close-in location. Excellent Los Altos schools.

Coming Soon! Regally positioned in complete privacy on approximately three acres, this palatial residence conjures images of European grand manors. Masterfully crafted with unparalleled quality, the estate presents luxurious grandeur and sumptuous comfort in equal measures. From the magnificent entrance with multiple water features and impressive porte cochere to the lavishly appointed interiors, the ambiance is decidedly elegant and glamorous. Vast expanses of richly veined marble or Brazilian walnut finish the floors, crown moldings are uniquely appointed with unmatched detail, and lofty ceilings showcase dazzling German chandeliers. Grand formal rooms are complemented by a more relaxed family room adjoining a tremendous gourmet kitchen, a cherry paneled office is fit for any executive, a twelve-seat theatre, and wine cellar awaits your collection. Outside, the grounds are truly resort-inspired with an infinity edge pool and spa, amazing entertainment terrace lined with European statuary, barbecue center, and breathtaking grounds.

Designed by renowned Palo Alto architect Steve Borlik, this stylish home is situated at the end of a premier cul-de-sac just steps from downtown Los Altos and acclaimed Santa Rita Elementary. Perfectly turn-key from top to bottom, this single-level home offers an incredible great room, spacious formal dining room, inviting family room, private bedroom wing, and a large, well-designed backyard. Enjoy high-end construction and materials, custom built-ins, expansive picture windows, a built-in sound system, and solar powered energy. Having both a formal dining room and an open-concept kitchen and family room provides the perfect venue for entertaining and relaxing with family. And in the backyard, a gorgeous travertine patio surrounds the resort-style pool and spa, a fire pit patio sits within an area of level lawn, and a garden has two large raised beds and easy access to a storage shed or potential ADU site. Move-in ready, with a highly coveted location!

This remarkable home offers a rare combination of space, style, and convenience, highlighted by a resort-inspired backyard. ~11,000 sq. ft. lot on one of the most sought-after streets in Los Altos! Premier North Los Altos neighborhood just a mile to Los Altos downtown and convenient to all three local schools for this home. Desirable 5-bed/4-bath floor plan with a spacious en-suite on the main level. Expansive great room with open-beam ceilings and seamless flow between the kitchen, dining, family areas, and the outdoors. Kitchen features granite island with breakfast bar and top-of-the-line Viking Professional 6-burner gas cooktop, Sub-Zero refrigerator and wine refrigerator, two refrigerated drink drawers, and two Bosch dishwashers; ample cabinetry and pantry for storage. Primary suite boasts high ceilings, balcony, 2 walk-in closets, 2-way fireplace, steam shower, and jetted tub. Fabulous private backyard complete with covered patio, pool with water features, cabana with fireplace, outdoor island grill, and lawn/play area with Goalrilla basketball hoop. Cabana offers ~300 sq. ft. additional space not included in the 3,471 sq. ft. main home. Acclaimed Los Altos schools: Santa Rita, Egan, Los Altos High. Convenient to downtown, library, community center, TJs, and Whole Foods

This remarkable home offers a rare combination of space, style, and convenience, highlighted by a resort-inspired backyard. ~11,000 sq. ft. lot on one of the most sought-after streets in Los Altos! Premier North Los Altos neighborhood just a mile to Los Altos downtown and convenient to all three local schools for this home. Desirable 5-bed/4-bath floor plan with a spacious en-suite on the main level. Expansive great room with open-beam ceilings and seamless flow between the kitchen, dining, family areas, and the outdoors. Kitchen features granite island with breakfast bar and top-of-the-line Viking Professional 6-burner gas cooktop, Sub-Zero refrigerator and wine refrigerator, two refrigerated drink drawers, and two Bosch dishwashers; ample cabinetry and pantry for storage. Primary suite boasts high ceilings, balcony, 2 walk-in closets, 2-way fireplace, steam shower, and jetted tub. Fabulous private backyard complete with covered patio, pool with water features, cabana with fireplace, outdoor island grill, and lawn/play area with Goalrilla basketball hoop. Cabana offers ~300 sq. ft. additional space not included in the 3,471 sq. ft. main home. Acclaimed Los Altos schools: Santa Rita, Egan, Los Altos High. Convenient to downtown, library, community center, TJs, and Whole Foods

Striking contemporary home with expansive grounds and privately located pool. Over one-third acre lot includes an inviting front garden courtyard, spacious rear terrace, manicured level lawn and stone walkways leading to the sun-swept pool. Newly remodeled in 2015. Traditional foyer introduces espresso-hued floors that extend through the main level. Formal dining room with wood-burning fireplace and wide front window. Open concept chef’s kitchen with Poggenpohl cabinetry, Caesarstone counters, peninsula with breakfast bar seating, waterfall-wrapped island and stainless steel appliances. Three bedrooms on main level. Spacious master retreat encompasses the entire second level with dormer ceiling and carpeted floors; master bath with tumbled marble tile, separate vanities, glass-enclosed shower, and free-standing tub. Beautifully landscaped grounds. Attached 2-car garage with electric car outlet. Desirable North Los Altos location. Excellent Los Altos schools!