Luxury real estate for sale San Gregorio, United States

An exceptional Woodside estate set on approximately 6.6 acres, this private 4-bed, 3-bath residence offers a rare opportunity to experience refined living surrounded by nature. Encompassing approximately 2,760 sq ft, the home is thoughtfully designed to capture captivating views of the surrounding mountains & clear across the Bay while providing a serene retreat just moments from local amenities. Soaring ceilings, expansive living spaces create a sense of volume & elegance, complemented by two fireplaces adding warmth & character throughout the home. Generously sized bedrooms offer comfort & privacy, while large windows invite an abundance of natural light. The kitchen serves as a central gathering space, featuring an island, pantry & seamless connection to the main living areas. Indoor-outdoor flow leads to a spacious deck & hot tub, perfect for relaxing & set against a backdrop of tranquil, open land. The grounds offer remarkable privacy & scale w/space to explore & unwind. Additional features include a recently installed Jackery generator, Tesla EV charger, attached 2-car garage & abundant on-site parking. This is a rare offering for the discerning buyer seeking an elegant refuge where peace, privacy & convenience coexist in one of the Peninsulas most prestigious settings.

Set on 8.5 private acres in coveted Half Moon Bay, this beautifully remodeled contemporary ranch offers the rare combination of refined living and exceptional equestrian amenities just minutes from town. The home has been thoughtfully redesigned with a clean, modern aesthetic and an effortless indoor-outdoor flow. A dramatic living room anchored by an architectural steel fireplace opens to serene views of the creek and mature landscaping, while the formal dining area creates an elegant setting for entertaining. The chef’s kitchen is finished with sleek European cabinetry and top-tier appliances including a Gaggenau stove and steamer, Miele dishwasher, oven and refrigerator, and a built-in wine fridge. A spacious family room and dedicated office add flexibility for both relaxed living and working from home. The property is equally impressive for equestrian use. A well-designed barn offers three stalls, tack room and hay storage, complemented by paddocks, an arena, and open pasture. Direct trail access makes it ideal for riders seeking both privacy and immediate connection to the coastal trail system. Additional features include a detached two-car garage and a separate one-bedroom mobile home with kitchen, living room and bath—perfect for guests, extended family, or caretaker use. Gated and peaceful, yet just minutes from the charm of downtown and the coast, this is a rare opportunity to own a turnkey ranch property in one of the most desirable areas along the San Mateo County coastline. Offered at $3,798,000

Perched a top of Skyline Ridge, this gated custom estate offers spectacular views of the San Francisco South Bay, including Mt. Diablo, Stanford, and San Jose. Nestled on a private 5+ acre east-facing parcel near the 942-acre Wunderlich Park, the home features 5 bedrooms, 4.5 bathrooms, 4 large decks, and a 2-car garage. The gourmet kitchen with center island, dining room, and large pantry opens to the great room with vaulted ceiling, skylights, and 3 French doors. Upstairs showcases imported slate floors, a central family/activity room, a guest half bath, a library/office, and a spacious primary suite with a walk-in shower, a 2-person jetted spa, a private deck, double sinks, a bidet, and a walk-in closet. A nearby flexible room could serve as a bedroom, nursery, or den. The laundry area opens to a flat yard suitable for a future pool, tennis court, or stables. Downstairs includes 2 bedrooms, a large bath, a sitting room, and a fully self-contained ADU with private entry and a deck. In the coveted Portola Valley/Woodside School District, the estate feels private yet is minutes from Alice's Restaurant, Fogarty Winery, central Woodside, Stanford, and the Coast.

Located within the gated Ocean Colony community, this spacious 5-bedroom, 3.5-bath residence offers exceptional coastal living just moments from the beach. Beautifully updated and meticulously maintained, the home blends elegant design with comfortable everyday living. The main level features a formal living room, formal dining room, and a chef-style kitchen appointed with high-end appliances and marble countertops. A spacious family room opens seamlessly to the backyard, creating the perfect indoor-outdoor flow for entertaining. The outdoor space includes a patio, cozy firepit, and a private putting green. This level also includes a versatile office or guest bedroom with an ensuite bathroom and a convenient half bath. Upstairs, the expansive primary bedroom suite offers a relaxing retreat with a sitting area, dedicated home gym space, and a luxurious ensuite bathroom with dual vanities and three walk-in closets. Three additional bedrooms, a full bathroom, and a laundry area complete the upper level. Additional features include owned solar panels, Tesla Powerwalls and EV chargers, and a spacious three-car garage. The landscaping is drought tolerant requiring little to no water and very low maintenance. Ideally located near The Ritz-Carlton Half Moon Bay, the beach, and the shops and restaurants of Downtown Half Moon Bay, the home also offers convenient access to Highway 92 for commuting to the greater Bay Area. Residents of Ocean Colony enjoy resort-style amenities including a clubhouse and fitness facilities, pool and tennis, and 36 holes of golf adjacent to The Ritz-Carlton making this an exceptional opportunity to enjoy the best of coastal living.

This home personifies tranquility. Nestled in a serene country setting just minutes from I-280 and top-rated Portola Valley schools, this beautifully updated 6-bedroom, 2- Office 3+-bathroom custom designed home perfectly balances rural privacy with modern convenience. The interior boasts an expansive, light-filled atmosphere defined by cathedral ceilings and large windows that frame the surrounding natural beauty. High-end functional upgrades include a spacious center island kitchen with adjacent family area & fireplace. A formal dining room overlooking the pond and into the Redwoods. A spacious living room with soaring ceilings and fireplace. A large primary bedroom with a spacious walk in master bathroom and a nice private deck with a hot tub. 2 artist studios / offices. One was used a pottery studio the other was a photographic studio. Outside, the property serves as a private retreat with direct access to local hiking and biking trails. An additional magical feature is the adjacent pond. This provides a magical setting and helps the home create an oasis of peace and tranquility.

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.

Welcome to Cypress Cove, a sought-after coastal community. This beautifully updated three-bedroom, three full bathroom home features a bright open layout, vaulted ceilings, hardwood and marble floors, and newer carpet in the bedrooms. The chef’s kitchen impresses with a Barazza four-burner gas cooktop, oversized stainless steel sink, Miele oven and dishwasher, and a premium Liebherr refrigerator. Spacious primary suite features a walk-in closet and a spa-glass shower with skylight. Enjoy multiple living areas, a private deck, and an abundance of natural light throughout. Additional highlights include a cozy fireplace, recessed lighting, a laundry closet with a washer/dryer, and an attached two-car garage with an additional 9' x 18' bonus storage room. Located minutes from the ocean, hiking trails, and charming downtown amenities, this residence combines modern convenience with a serene lifestyle.

Rare opportunity to build on this oak-studded parcel. Large home deemed possible by Lea and Braze engineers; price includes feasibility study, survey, and septic perc test results. This land could be a great location for your estate home or quiet getaway. Approximately one mile from Thomas Fogarty Winery. Plenty of room for horses, animals and/or hobby farm, you'll find that you are perfectly situated to access the hiking and riding trails that abound in the open space near this property. Seller has two lots for sale (0-220 and 0-250 Heacox), and the actual address is not yet determined. Electric pole on site. Seasonal creek and temperate climate.

Tranquil land. Excellent opportunity to build on! This sun-drenched parcel has a gentle grade for development.3800 ft2 home plus 1000 ft2 ADU deemed possible by Lea and Braze engineers; price includes feasibility study, survey, and septic perc test results. This land could be a great location for your estate home or quiet get-away. Plenty of room for horses, animal,s and/or hobby farm, you'll find that you are conveniently located to access the hiking and riding trails that abound in the area's open space. Seller has 2 lots for sale (0-220 and 0-250 Heacox); the actual address is not yet determined. Electric pole on site. Old well on-site (plentiful water here), you add septic system. Invest in your future!

On the market for the first time, this exceptional Craftsman home is located in prestigious Blue Oaks, an enclave of estate homes surrounded by 285 acres of open space & trails. Built by Chessler Construction in 2003, the home showcases timeless architecture, exquisite woodwork, & a flexible multi-level floor plan designed for today's lifestyle. Set on approx. 1.29 acres, the property enjoys a backdrop of natural beauty with miles of nearby hiking trails, plus sweeping views out to the San Francisco Bay & East Bay hills from the top level. Main level is ideal for both grand entertaining & comfortable everyday living, offering formal venues, professional office, & seamless connection to expansive outdoor spaces that include front & rear terraces, loggia with fireplace, plus an in-ground spa & outdoor shower. Primary suite has Bay views & each bedroom has private balconies & elegantly appointed bathrooms. Finishing touches include an attached 4-car garage, backup generator, & a community pool & clubhouse. Blue Oaks location offers quick access to Portola Valley's charming town center & excellent public & privates schools, with Stanford University just 15 minutes away. Acreage & open space provide unmatched lifestyle in one of the area's most sought-after neighborhoods.

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.

Classic architecture & beautifully curated grounds define this inviting Woodside home set on more than one-third acre moments from the town center. Stone-clad exteriors, newly planted lawns, & a picture-perfect approach introduce interiors that are warm, welcoming, & thoughtfully designed for everyday living. Natural light fills the home through expansive windows, hardwood floors, detailed millwork, & a floor plan that offers both openness & comfortable separation of spaces. Main living areas transition easily from formal rooms to casual gathering spaces, welcoming family room & well-appointed kitchen designed for both function & connection. Lower-level recreation/media room adds flexibility for entertainment or office use. Privately located primary suite with jetted tub & steam shower, bedroom with its own outside entrance & adjacent bath ideal for guest quarters. Outdoor living is a central focus, with a large arbor-covered deck extending from the home & terraced grounds below featuring a play area & garden spaces, all enhanced by refreshed landscaping. Located on a cul-de-sac street in the Woodside Glens neighborhood, with acclaimed Woodside School & offers a combination of traditional appeal, updated comfort, & an exceptionally convenient setting with a true sense of retreat.

Imagine life at this exceptional Portola Valley residence: an elevated lifestyle in one of the areas most coveted settings. Close-in to Alpine Road and Highway 280, this private sanctuary is surrounded by natural beauty while close to every convenience. A dramatic arrival begins with a sculptural stone waterfall and a grand entry flanked by flexible living spaces: a private office or fifth bedroom with a half bath on one side, and a guest retreat with kitchenette and full bath on the other. This sets the tone for the home's sleek design and exceptional craftsmanship. Upstairs, soaring ceilings define the expansive living area, where walls of glass invite the outdoors in. Designed for entertaining and everyday living, the great room with modern fireplace opens through telescoping glass doors to an expansive terrace and resort-inspired grounds with a spa. The adjoining kitchen features bespoke counters, rich walnut cabinetry, generous pantry, and top-tier appliances. The luxurious primary suite offers a private terrace, walk-in wardrobe, and serene bath with skylit shower and rainfall fixture. Additional spaces include two more bedrooms, a library with fireplace, wine room, and mudroom. Owned solar and EV charging (240V) add efficiency. 12,400 square foot lot within the Portola Valley School District.

This hidden treasure on nearly half an acre offers an expansive, serene lot tucked behind a private gated entry. Professionally landscaped grounds showcase mature orchard trees, lush plantings, and an abundance of flowers blooming year-round. The exceptional single-level main residence features three bedrooms, three bathrooms, and 1,842 sq ft of luxurious living space. Completely renovated in 2017 the open, light-filled floor plan is enhanced by multiple skylights and French Oak floors that extend throughout the home. A beautiful lanai leads into the spacious living room, highlighted by custom built-in cabinetry and designer lighting, flowing effortlessly into the chef’s kitchen with a large center island, premium Thermador appliances, and an inviting dining area. Multiple glass doors open into a stunning 400 sq ft lanai seamlessly blending indoor and outdoor living. The primary suite is a private sanctuary with spa-like bath that features Italian porcelain tile, mosaic marble floors, crystal chandelier and custom closet. Outdoor living spaces include multiple seating areas, an outdoor kitchen, and a gas fire pit and an abundance of parking. A detached garage includes an 687 sq ft of versatile space, ideal for a guest suite or home office. Additional highlights include a 600 sq ft basement, perfect for an office or recreation room, a private well, and potential to add an ADU or expand further. Perfectly situated just moments from Village restaurants and shops, and close to hiking and biking trails, Edgewood Park, Stanford University, major tech campuses, and Interstate 280. Located within the highly regarded Woodside School District.

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.

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.

Overflowing with character, this 1,933 square foot home is sited on an over 16,000 square foot lot, with views looking over the peninsula towards the bay and east bay hills. An over 300 square foot front porch welcomes you into a foyer, spacious living room and dining room. The eat-in kitchen provides a breakfast bar with granite counter top that opens to the outdoor bbq patio with ample space for seating and detached two car garage. Spacious workshop with cabinets offers many use options. All three bedrooms benefit from tons of natural light and over look the large garden area. Lovingly maintained, the garden offers raised beds, fruit trees, olive tree and various entertaining areas. The large yard and lot may offer expansion and development opportunities as well. Every space in the home has views of the well maintained grounds. Well located in Emerald Hills, this home has easy access to the main transportation routes, shopping and local community activities.

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)

This exceptional 2.8-acre vacant parcel presents an extraordinary opportunity in a prestigious setting, offering endless possibilities for building. Perfectly situated beside a magnificent high-end estate, also available for sale at 961 High Road, this property can stand on its own or combine with the neighboring estate for an unparalleled expanse. The vacant land, bordering the Menlo Country Club, offers gently rolling terrain with open meadows, wildflowers, perimeter trees, and views of the East Bay hills. With a serene landscape and conceptual plans for a custom residence and accessory structures, this lot offers a unique chance to establish an exceptional property in a sought-after location. 961 High Road is also for sale.

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.

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.

Build your dream home on this approx. 4.2-acre undeveloped country parcel situated adjacent to Portola Valley on Santa Clara County land just up from the Ladera Shopping Center shops and restaurants. The lot is surrounded by open space, Stanford lands and the gently flowing Los Trancos Creek and is in the Palo Alto Unified School District.

3554 Oak Knoll Drive is your everyday treehouse - an airy 3 bedroom, 2.5 bathroom retreat perched in Redwood City's coveted Emerald Hills neighborhood. Approximately 2,398 square feet of thoughtfully designed living space unfolds among walls of windows, filling every corner with natural light and views of the surrounding trees. Recent flooring, fresh interior and exterior paint, and updated bathrooms mean you can unpack and start living right away. A separate, finished approximately 400 square foot flex space extends your possibilities: movie room, library, art space, or meditation area - whatever fuels your next chapter. The open kitchen / dining / living layout keeps gatherings easy, while the three bedrooms offer privacy without sacrificing flow. Minutes to Edgewood Park trails, Hwy 280, and downtown Redwood City, this peaceful home blends treetop serenity with everyday convenience.

Nestled in the Emerald Hills neighborhood of Redwood City, this nearly century-old Craftsman home is a serene oasis that feels like living in a sophisticated treehouse. Set on a fully fenced, nearly half-acre lot, the property is defined by gorgeous heritage oak trees that create a sculptural canopy over various flat areas perfect for lounging, dining, or play. Inside, the home reveals stunning period details, including beautiful hardwood floors and a breathtaking double-height living room anchored by a statement fireplace of reclaimed stone, all framed by original Redwood beams, paneling, and a handcrafted banister. While the home retains its historic soul, it features modern comforts like an updated kitchen with newer appliances, refreshed bathrooms, and updated systems, including a newer roof. Take in peaceful Bay views on the lounging deck while looking over the terraced planting beds with decomposed granite pathways meandering throughout. Beyond the living space, an oversized garage with a workshop area and ample storage offers incredible versatility, while the vast lot provides significant potential for expansion, a separate ADU, or nearly anything imaginable. Plenty of parking for guests and easy access to the 280 for a seamless commute to San Francisco or Silicon Valley.

Classic traditional appeal defines this split-level home with charming white picket fence and expansive wraparound grounds. Best block of Alameda De Las Pulgas with easy access to Woodside Rd and 280. Freshly painted interiors are complemented by hardwood floors in most rooms contributing to the homes overall warmth. The living and dining room combination offers generous space highlighted by a fireplace, crown moldings, and abundant natural light. The kitchen has been refreshed with newly painted cabinetry, reglazed tile countertops, and new vinyl flooring, plus there is a spacious family room with new carpet, fireplace, and rear deck access. The homes 4 bedrooms and 2 baths include a main-level bedroom and newly remodeled bath, plus three upstairs bedrooms and a bath with resurfaced finishes. Outdoor living is a standout feature, with a large wraparound yard that includes expansive hardscape, deck with shade sail, a rear lawn with putting green, and a cabana lounge for relaxation or entertaining. Attached 2 car garage with built in cabinetry, AC, dual pane windows and more make this a great place to call home!