luxury real estate for sale San Gregorio, United States

Escape to the country coastal lifestyle just two minutes from the sandy beaches of the Pacific Ocean. Spanning 19 acres of mostly level grounds, this pristine property offers opportunities for organic farming and equestrian pursuits and has private access to Tunitas Creek with direct trail to the ocean. At its heart lies a stylishly designed home where contemporary elegance seamlessly unfolds. Towering ceilings, expansive windows, and an open floor plan create a modern ambiance. Fine hardwood floors, cable-strung stair railings, and exquisite tile and quartz finishes enhance the allure. The gourmet kitchen and separate wine bar anchor the flowing public spaces and a vast front deck with built-in heaters welcomes al fresco enjoyment. There are 4 bedrooms plus an ocean-view office or 5th bedroom. The main-level primary suite has a spa-inspired luxe bath plus there are two bedrooms in a separate wing with a large living room making it the perfect quarters for extended family. Three detached units serve as possible future living spaces or for office/storage needs now. Equestrian amenities include a 6-stall barn, fenced corrals and arena, plus a vintage barn. Two acres of organic farmland await cultivation and water is plentiful with four wells. Just 10 minutes away, find world-class golf, the Ritz Carlton, and charming downtown Half Moon Bay with boutique shops and restaurants. Whether cherishing the tranquil privacy of everyday life or escaping city life for coastal living on the weekends, this property offers the best of California living just one-half hour from the San Francisco Peninsula. At a Glance • Luxe contemporary style home 2 minutes from the beach • Approximately ~ 19.06 acres (18.93 acres + 0.1375 acre easement) • One-quarter interest in shared 0.55 acre easement to enchanting Tunitas Creek culminating at the Pacific Ocean • 4 bedrooms, office or 5th bedroom, and 3.5 baths, including 2-bedroom, 1-bath guest quarters • Approximately 3,345 square feet of living space • Detached studios, with plumbing in place, for potential future living quarters, office space, and/or workshops • Equestrian facilities with 6-stall barn, workshop, fenced corrals and potential arena space, plus large vintage barn • Approximately 2 acres of organic farmland • 4 wells plus creek with pump • Just 10-minute drive to quaint downtown Half Moon Bay with boutique shops and restaurants

One of the most extraordinary properties on the SF Peninsula on almost 18 acres. The property has endless potential (including zoning for commercial use) and has been used to raise horses, to showcase a car aficionados collection, and to host philanthropic and social events easily up to 200 guests, all the while serving as a comfortable venue for everyday living. 5-floor main residence from the 10+ car garage to a viewing room at the top of one of the turrets. Personal quarters include multiple apartments plus tremendous, dedicated office space. The barn is a matching masterpiece with both buildings hand-crafted by local and international artisans with individual details taking up to a year to complete. Magnificent grounds include a 4-tee golf practice area, RC car track, resort-inspired pool and spa, and direct access to miles and miles of hiking and equestrian trails in bordering Wunderlich Park. Woodside or PV schools. 17 minutes to Woodside town center.

Discover your private sanctuary nestled on over an acre of serene woodland in the quiet embrace of the Redwoods. This exquisitely remodeled home offers two bedrooms and two bathrooms, positioned creekside for a tranquil, nature-filled living experience. Just steps away from the Butano Canyon community pool, this property boasts one of the premier locations in the area—perfect for unwinding, recharging, and enjoying outdoor activities like playing in the creek or gathering around the cozy fire pit under towering Redwoods. The spacious lot provides ample opportunity for expansion, whether you envision adding an accessory dwelling unit (ADU) for guests or creating more room for your dream home. Animal lovers will delight in the space to roam and the freedom to keep pets. Located just 10 minutes from the vibrant town of Pescadero and its picturesque coastal beaches, and less than an hour's drive from the tech hubs of Silicon Valley, this gated community offers both seclusion and accessibility. Experience the best of both worlds—peaceful, rural living with proximity to urban conveniences. Your dream home awaits in the majestic Butano Canyon.

Coming Soon! Located in the sought-after Woodside neighborhood of Skywood Acres, this magnificent three-level home offers breathtaking panoramic views of the Bay and City Lights. With a compound-like setting, privacy and stunning vistas of The Peninsula and Bay are ensured. Spanning approximately 5,500 square feet, it accommodates large families and remote work with two offices. The well-designed layout includes a spacious kitchen, separate dining and family rooms, a library, and an office. The ground floor features four bedrooms, including two primary, one with a balcony, and five luxurious bathrooms. Remodeled baths and kitchen blend elegance and contemporary flair while preserving the Spanish architectural theme. The third-floor office provides inspiring views from San Fransico to San Jose. This Skywood Acres residence combines luxury, comfort, and mesmerizing views for a serene retreat. La Honda Winery manages the vineyard and produces quality wine! Make this your Home Sweet Home!

Welcome to The Lake House! This beautiful, 6 bedroom, 8 bathroom house sits on 4.2± acres with valley views, a private lake along with a private redwood grove. Step into this amazing contemporary country home featuring abundant light, energy efficient metal roof with solar panels supporting tesla powerwalls. An outside gym - a Kenguru Pro Fitness Workout station, dog run, and custom-built tree house are all located on one side of the property. Upon entering the front door, the captivating views draw you immediately to the upper terraces. On the main level of the home, there are 3 en suite bedrooms and a separate office with full bath, along with the living/dining room, eat in kitchen and family room. The lower level has a secondary prime bedroom with large bath and closet area. Two bedrooms with a shared bath. A safe room, and a small theater room with a full bath, and a large family/playroom supported by a secondary kitchen area. There are over 4000± sq. ft. of floating deck designed terraces featuring slate squares. A built in fire pit with a level for comfortable seating allows one to enjoy the sunsets over the valley. The stucco walls are finished with Brazilian ipa wood accents and ceilings under the first floor decking. There is an attached 2-car garage and a detached 2-car garage. 2 EV outlets. Private 20,000 gallon water tank with dedicated hydrant. The private lake provides an ideal spot for swimming, fishing, or just relaxing in the sun. Walk the trail around the lake and relax in your own private redwood grove. Enjoy the privacy and tranquility of country living, with access to an extensive trail system, and still be able to quickly access the flats - only 3.9 miles from 280. Portola Valley schools.

This stunning Portola Valley gem is set back from the street on almost one-third acre. Beautifully updated, this move-in ready home boasts one-level living with a level yard in the front and a private terrace in the back. Inside, newly refinished hardwood floors, an updated kitchen, and bathrooms with designer touches throughout provide elegance and style throughout the tastefully appointed country home. Expansive windows provide abundant natural light into the living spaces. The finished garage offers additional play and storage space with potential for a family room. The gated front motor court provides plenty of parking. The level yard, fresh landscaping and new pavers make it perfect for entertaining and outdoor activities. Additionally, the home's sizeable lot provides various expansion options. Conveniently located near Highway 280 and Sand Hill Road venture capital centers, this home is perfect for commuters. Close to Portola Valley schools, Village Square, the library, the Farmer's Market, and trails on the Woodside/Portola Valley loop, it is a true Portola Valley gem!

Rare 3.3 level acres-perfect for a family compound with multiple structures for the ultimate in flexibility of use and all in a fabulous close-in-location. Comprised of several buildings with the opportunity to create a family compound, conference center, or both, the entire estate blends Spanish Revival architecture, with signature red-tiled roofs, and sleek modern interiors. Espresso-hued hardwood floors, towering sky-lit ceilings, and entire walls of glass imbue the home with sophisticated style and brilliant natural light and all on an exceptional setting. Main home with 4 bedrooms and 5.5 baths, including a 2-bath primary suite. Impressive open concept kitchen with vaulted ceiling opening seamlessly to the family room with multiple doors to the impressive grounds. Detached office/conference center/recreation structure with 1 bedroom and 1.5 baths. Attached fitness center/recreation room with 1 bath and sauna. Detached guest house,1-bedroom, 1-bath with full kitchen. Two three car garages for a total of 6 garage spaces. All inclusive approximately 10,066 square feet-buyer to verify. Incredible value and opportunity with excellent Portola Valley Schools, perimeter trees, sparkling pool, gated estate-a must see.

Undeveloped parcel in prime location in central Woodside set amongst estate properties. Currently used as vineyard and adjacent to 211 Winding Way that is being offered for sale. Endless possibilities to create your own compound and vision. Stately trees and gentle knoll with loads of sunshine.

The allure of nature seamlessly intertwines with architectural brilliance at this exclusive vineyard estate on one of Woodsides most esteemed streets. Spanning over 4.399 acres, with the possibility of purchasing the adjacent lot of 3 acres for a total of 7.4 level acres, the entrance sets the tone of what lies within with an organic setting that begins with a serene lily pond and interconnected waterways with architecture by Atelier Ugo Sap of San Francisco and built by Van Acker Construction whose detail work is undeniable. The grand formal living room an antique mantelpiece adorn the wood burning fireplace and formal dining room grace the home for large gatherings. Dedicated office with fireplace, impressive open kitchen, breakfast and family room. Two levels with elevator, 6 bedrooms including luxurious primary suite, 6 full baths, and 2 half-baths including two main-level bedroom suites. Rustic-designed 1 bed/1 bath pool house with luxurious spa and kitchen. Additional structure for flexible use as gym, office or guest house with kitchenette and bath. Sparkling pool and magnificent grounds. Approximately 11,650 total square feet including 3-car garage. Cultivating wine, jam, honey and olive oil from the property. Acclaimed Woodside Elementary School and convenient location.

Interesting opportunity to build on this peaceful, sun-drenched parcel. This land could be a great location for your estate home or quiet get-away. 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 adjacent to this property. Seller has 2 lots for sale (0-220 and 0-250 Heacox) and the actual address is not yet determined. Land has been surveyed and septic perc tested. Plans available to prospective buyers. Electric pole on site and an old well. Miles of trails and open space. 1 mile from Thomas Fogarty Winery.

Interesting opportunity to build on this peaceful oak-studded parcel. Sun and shade, flat and grade, seasonal creek, this land could be the location for your estate home or quiet get-away. 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 adjacent to this property. Seller has 2 lots for sale (0-220 and 0-250) and the actual address is not yet determined. Land has been surveyed and septic perc tested. Electric pole on site and area should have plentiful water for a well. 1 mile from Thomas Fogarty Winery.

Embrace breathtaking views from the mid-century modern rustic home in prime Westridge location of Portola Valley. Set on ~2.5 private acres, this gem is a blank canvas for the creative buyer. Great layout with good-sized rooms ready for personalized improvements. Ideal location with top-rated Portola Valley Schools. Incredible value!

Move in condition and lovely views of the western hills. The home's versatile floor plan (officially three bedrooms and four bathrooms) includes an expansive lower level with a large family room, extra storage area, and a large guest/au pair suite or second home office. The main level has an open living, dining, and kitchen area, the primary suite is amazing featuring: a gas fireplace in the bedroom, a small private deck with views, a large primary bathroom with a large glass shower, two vanities, spacious dressing area, and a huge primary closet. Also on a third level and in the primary suite area is a stunning office with views western hills and a private deck. You'll never go back to the office once you've worked here! Two other bedrooms and bathrooms are on this same level. The kitchen is a large entertainer's island kitchen with state-of-the-art appliances. The living, dining and kitchen area opens to a new Trex deck which boasts expansive views. The lower level offers a spacious family room with a fireplace, a full bathroom, and a large storage area. Also on the lower level is an au pair or guest suite. Wonderful views from the hot tub off the family room. A two car garage is located off the family room. The home has solar panels and three Tesla batteries, as well as EV charging.

This secluded, gated 2.96+/- acre property has three bedrooms, three bathrooms in the main home, and a stunning separate art studio/office with its own driveway. This contemporary home offers a seamless integration of home and nature. The vaulted ceilings soar at approximately 14 feet. Skylights and oversized windows and doors provide natural light and an effortless flow to the natural surroundings— providing inspiration. The living room has a fireplace and sets of doors on both sides that open to patios. A nearby office with built-ins is a few steps up. The formal dining room is surrounded with windows and doors. This allows you to expand entertaining to the outdoor areas. The eat-in kitchen offers sleek maple cabinetry— and lots of it. Stainless steel appliances provide a chef with the right tools. There is a pool, and nearby lower-level apartment or exercise space, with a full bathroom and kitchenette. Located in the desirable Westridge Neighborhood, this home is the epitome of Portola Valley living and is just a short distance to the global financial and tech centers on Sand Hill Road. Highlights: Main Home • Desirable Westridge Neighborhood. Close to Highway 280 for easy access to San Francisco and Silicon Valley. • Three bed, three bathroom, with office, 4320+/- square foot main home. • Lower level au pair/guest apartment with a private entrance, Murphy bed, full bath, kitchenette, and storage. Wall of windows and doors open to a patio overlooking the pool. Pool has shade cabana. • Spacious living room with fireplace, and refinished maple floors. Wall of oversized windows/doors open on both sides to vast terraces. • Large dining area wrapped in windows and doors that fill the space with light and create an easy flow inside and out for expanded entertaining options. • Office featuring custom built-ins. • Primary suite has exceptional storage that includes built-in display shelving that reaches to the ceiling. Fireplace, private bath, over sized doors open to a patio. • Eat-in kitchen with custom maple cabinets, pressed concrete floors, stainless steel appliances, desk area, and adjacent large laundry room with extra storage and two utility sinks. • Amazing art studio/garage or guest House: 1496 square feet; a separate drive leads to this detached building design studio. Soaring ceiling has skylights, plus industrial and directional display lighting. Oversized doors for receiving guests or moving artwork or parking multiple collectable cars. Full bathroom. Kitchenette. Custom artwork storage. Plus, upper-level office (or possible loft bedroom) • Two-car garage plus a one-car carport. Generous off-street parking. • Woodworking/creative space with roll up garage door. • Freshly painted exteriors. Refinished maple hardwood floors. Excellent storage throughout. • Gated property of approximately 2.96 acres. Includes a pool with sheltered cabana/barbecue area, walking paths, and an elevated deck area. • Schools: Ormandale Elementary K-3, Corte Madera School 4-8, Woodside High School 9-12

481 West Maple Way, Woodside is a contemporary gem with awe-inspiring views of the western hills and Crystal Springs reservoir. This home showcases clean lines, soaring ceilings, and an abundance of glass creating a seamless integration with the outdoors. The open-concept layout is ideal for entertaining. A gourmet chef's kitchen with top-of-the-line appliances and a large center island is a focal point. The living and dining areas provide a comfortable and stylish setting from which to admire the view. The master suite is a private sanctuary with a spa-like en-suite bathroom and spacious walk-in closet. The separate studio cottage with full kitchen provides flexibility. Expansive outdoor living spaces include beautiful native plants, a large terrace for al fresco dining, an outdoor living room, soothing hot tub, and putting green. This property combines the best of both worlds serene seclusion and proximity to the vibrant amenities of Silicon Valley and top-rated schools.

Exceptional half acre+ with bay views in sought after Emerald Hills custom home built with meticulous attention to detail. Local artisan designed stone and ironwork. Outstanding floor plan with a focus on indoor-outdoor living the home seamlessly extending from the family room to a mostly covered, tiled deck with a fireplace, lounge, dining area and well-equipped outdoor kitchen offering a serene and inviting space for everyday living. Vaulted ceilings including living room with fireplace, formal dining room with fireplace, sun room and main floor bedroom suite. Granite chefs kitchen with views, breakfast room with outdoor patio, plus adjacent family room with fireplace. Upstairs luxurious primary suite with fireplace, vaulted ceiling, views and sitting room, plus two additional bedrooms and adjoining lounge or office. Lower-level flexible-use room for office, 2-car garage PLUS 735 square feet studio including half bath-possible ADU conversion. Approximately 5,173 square feet of conditioned space plus 2-car garage. Mostly float lot with vast lawn, huge entertaining spaces, privacy and views. Excellent Roy Cloud School, views and vast lawn, mostly flat land. One-of-a-kind enchanting home resting on gentle knoll-a must see.

This gorgeous, spacious contemporary home is nestled atop the trees of verdant Emerald Hills, an unincorporated town between Woodside and Redwood City and close to 280. With sweeping Bay views all the way to Mt. Diablo, this much luxury at this price has to be seen to be believed. Set between two greenbelts, the privacy is unbeatable. Beautiful landscaping, a hot tub with a view, and an expansive back deck make indoor-outdoor part of life. Tasteful, open-plan, and sophisticated, there are 12-foot ceilings throughout, wood, stone, and carpet floors, skylights and light-flooded windows. On the ground floor, there is a large family room, 3 bedrooms and 2 bathrooms (1 en-suite) along with a laundry room, mudroom, and grand staircase. The main stairs leads to the living areas on the second floor, with a wall of windows, two large living rooms (both with gas fireplaces), a dining room, and a gourmet kitchen built for chefs. Also on this floor is the vast master bedroom with a gas fireplace and en-suite bathroom with shower, jetted tub, and two walk-in closets. Multiple outdoor spaces are accessed from this level. On the third level, there are 2 additional bedrooms (or offices) with a full bath, a library area, and access to another outdoor patio and the hot tub. Close to many great hiking trails (Edgewood Park ¼ mile away, dog-friendly Pulgas Ridge 3 miles), and 1 mile to the award-winning Roy Cloud Elementary School. 7 minutes to 280, 8 minutes to Whole Foods and 12 minutes to 101.

Located in the highly desirable Woodside Heights on a vast 41,000 sq ft lot! Featuring an open concept floor plan, soaring ceilings and an abundance of natural light, this four bedroom, three bathroom, 2,990 sq ft villa sets the stage for gracious living and entertaining! Formal living room, fireplace and custom cabinets with access to the beautiful stone terrace. The large kitchen with dining bar opens to an inviting family room and adjacent spacious dining room. Paces away you have a separate laundry room, perfectly placed space for a home gym and beautiful wine cellar. Rounding out this level is a wonderful library/office and full bathroom. Just upstairs you have a private and spacious primary suite retreat with walk-in closet and spa-like bath! Down the hall, three additional bedrooms share a full hall bathroom. Relax or entertain outside in the elaborate yard with lush mature, landscaping boasting sweeping views and several seating areas. Located just minutes to Town Center, great schools and streamlined commute routes!

Nestled amongst the verdant Emerald Hills and majestic oak trees, 35 Agua Vista was custom-built in 2012 and perfectly sited to enjoy panoramic Bay views from nearly every room. Timeless architectural details with an elegant yet comfortable design complement the gracious scale of the interiors with high ceilings throughout. The spacious kitchen with expansive marble island, features a Thermador appliance suite with double dishwashers, double ovens, and abundant counter+storage space. Tucked away from the living spaces, the luxurious primary bedroom features a walk-in closet and sumptuous en-suite bathroom with water closet, soaking tub, two vanities, and a generous walk-in shower. The lower level features a dedicated gym, storage area, and an attached ADU with kitchenette, living space, bedroom, and full bathroom. Resort-inspired outdoor spaces offer multiple spaces for al fresco relaxation and entertaining including the upper terrace, outdoor kitchen with Viking grill and prep sink, infinity edge pool, in-ground spa, and fire pit. Additional comforts include an Enphase battery backup system, PV solar panels, two EV-chargers, and two washers and dryers in the laundry room. Mostly level sideyard for play and fenced garden beds. This home is a must see!