Portola Valley Homes with Hills View

Nestled in the heart of San Mateo County, Portola Valley is a picturesque town that seamlessly blends natural beauty with a vibrant community spirit. Known for its rolling hills and scenic landscapes, this charming enclave offers an idyllic lifestyle for those seeking tranquility just a stone's throw from the bustling Silicon Valley.

Portola Valley is renowned for its commitment to preserving the environment, with over 80% of its land designated as open space. Residents enjoy an abundance of outdoor activities, from hiking the trails of the Windy Hill Open Space Preserve to picnicking in the serene surroundings of the Portola Valley Town Center. The area is also home to a strong sense of community, with local events and farmers' markets that foster connections among neighbors.

One of the standout features of Portola Valley is the stunning homes with hill views. Imagine waking up to breathtaking vistas of the Santa Cruz Mountains, with the golden sun rising over the peaks and casting a warm glow on your property. These homes are designed to maximize the natural beauty of the landscape, featuring expansive windows and outdoor spaces that invite the stunning scenery indoors. Whether you prefer a modern architectural masterpiece or a charming rustic retreat, Portola Valley offers a diverse array of properties that cater to every taste.

With its exceptional schools, friendly community, and close proximity to major tech hubs, Portola Valley is not just a place to live—it's a lifestyle. Discover the perfect home with a hill view in this enchanting town, where every day feels like a retreat into nature.

Newest Portola Valley Homes with Hills View

$11,500,000

ML82062842 MLS

Spanning an exceptionally rare 5.239 flat acres, this remarkable property offers an unrivaled combination of privacy & convenience in one of the Peninsula's most desirable locations. Large, level parcels of this scale are virtually impossible to find, particularly in such a central setting with effortless access to Palo Alto, Menlo Park, Stanford & leading tech campuses. The property enjoys a breathtaking pastoral setting framed by gently rolling hills & bordered by the tranquil waters of Los Trancos Creek. Unlike many large estates on the Peninsula, this exceptional property is reached without navigating winding hillside roads. Comprising two APNs of approximately 4 & 1.239 acres, the estate presents unparalleled flexibility for creating a legacy family compound. Preliminary design concepts by a renowned architect envision a spectacular estate 20,000+ sqft. Geographically located in Portola Valley, the property falls under Santa Clara County planning & building jurisdiction & benefits from acclaimed Palo Alto schools. Offering unmatched scale, a rare flat topography, extraordinary privacy, pastoral beauty & one of the Peninsula's most coveted locations, this is a remarkable canvas upon which to create a world-class estate that will be enjoyed for generations to come.

Address not disclosed, Portola Valley

Listed by Billy McNair, 650-862-3266 from Coldwell Banker Realty
(If provided) CoList: from

$11,500,000

ML82062838 MLS

57-59 Los Trancos Woods RD, Portola Valley

Listed by Billy McNair, 650-862-3266 from Coldwell Banker Realty
(If provided) CoList: from

$3,498,000

3 Beds ⋅ 2 Baths ⋅ ML82060118 MLS ⋅ Portola Valley Ranch BLDG.

45 Bear Paw offers a rare opportunity to own an updated, single-level home just steps from the entry to Portola Valley Ranch. A 2 car garage with ample storage connects to the main level via interior elevator for easy, step-free access. Large windows frame the gracious living room, where soaring ceilings, designer chandeliers, and an attractive marble fireplace surround create a serene, light-filled space. Striking bar with custom glass shelving, wine fridge and floral wallpaper. Spacious kitchen offers handsome wood cabinetry, and recently updated counters and backsplash. Three generous bedrooms and two beautifully updated bathrooms are grouped together in bedroom wing. The primary suite enjoys its own peaceful views of Windy Hill, updated bath with roll-in shower, walk-in closet, and its own 100-sq.-ft. deck. Living space extends outdoors with a substantial patio and a 216-sq.-ft. attached sunroom. The Ranch is an extraordinary place to call home-- a 6 minute drive to the Ladera County Shopper and 8 minutes to Highway 280, yet offering a remote, resort-like feel with exceptional community amenities including heated pools, tennis courts, a fitness center, a community vineyard, gardens, and miles of hiking trails. Excellent Portola Valley schools. Roof recently replaced.

45 Bear Paw, Portola Valley

Listed by Lynn Wilson Roberts, 650-255-6987 from Compass
(If provided) CoList: Annie Roberts from Compass

$5,488,000

5 Beds ⋅ 4 Baths ⋅ ML82052826 MLS

Set on 2.8 AC, this home offers a peaceful retreat in a coveted setting. Warm, welcoming interiors span more than 3,700 SF across a multi-level floorplan, blending rustic character with an easy livability that harmonizes with the surrounding landscape. A soaring vaulted ceiling elevates the living room anchored by a fireplace and expansive windows framing views that reach toward the Stanford Dish, while the main living spaces also include a formal dining room, granite kitchen with Thermador appliances, a comfortable family room with a fireplace, and a lower-level recreation room. Five bedrooms plus an office provide flexibility and comfort. With nearby access to scenic nature preserves and trailheads, a short drive to the Ladera Country Shopper shopping center and local favorites such as Alpine Inn, this home offers a rare balance of seclusion and convenience, all with access to acclaimed schools including Ormondale and Corte Madera (buyer to verify eligibility).

285 Escobar RD, Portola Valley

Listed by DeLeon Team, 650-407-0160 from Deleon Realty
(If provided) CoList: from

$2,595,000

2 Beds ⋅ 1 Baths ⋅ ML82052857 MLS

Beautiful (Bonita!) very large property in upper Los Trancos Woods. Over 1.6 AC of mostly flat land with old, mostly not habitable House, Cottage, Garage and Carport, comfortably spread throughout the property. In Feb 2026, San Mateo County approved a 2 lot subdivision, and work is ongoing to complete the final map recording. The house is available prior to recording of the subdivision as a single lot for buyers who might want more flexibility in what they do with the property. Extensive geological, geotechnical, arborist, historical, biological and civil reports and plans come with the property.

245 Bonita RD, Portola Valley

Listed by Mike Sokolsky, 650-465-2573 from Coldwell Banker Realty
(If provided) CoList: from

$1,749,000

2 Beds ⋅ 2 Baths ⋅ ML82047556 MLS

SUNLIT GEM ON NEARLY ONE-HALF ACRE WITH PLANS TO EXPAND! Fresh, inviting, and completely sophisticated, this retreat has been transformed into a light-filled setting. Easily accessed via wide streets, the property spans nearly one-half acre of predominantly level grounds and includes plans for a future expansion. The current home, with 2 bedrooms and 2 baths, offers a streamlined scale yet the open concept design lends an unexpected sense of expansiveness. A crisp palette of whites defines the interiors, from the all-white kitchen with quartz countertops and subway tile backsplashes to the remodeled baths finished in marble and tile. Vaulted ceilings with skylights and exposed beams enhance the airy atmosphere, while wood-like luxury vinyl floors provide continuity throughout. Multiple sets of glass doors open to wraparound flagstone patios and expansive land, where limited tree canopies allow brilliant sunlight to fill both the interiors and outdoor gathering spaces. Finishing touches include a separate laundry room, an outdoor storage shed, and a two-car carport. Portola Valleys acclaimed schools and miles of scenic trails are just moments away, making this a remarkable opportunity to enjoy contemporary style and comfort today with the option to expand in the future.

76 Old Spanish TRL, Portola Valley

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

$7,495,000

5 Beds ⋅ 8 Baths ⋅ ML82036782 MLS ⋅ Blue Oaks BLDG.

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.

1 Redberry RDG, Portola Valley

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

$8,748,000

5 Beds ⋅ 8 Baths ⋅ ML82034238 MLS ⋅ Blue Oaks BLDG.

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.

7 Redberry RDG, Portola Valley

Listed by Billy McNair, 650-862-3266 from Coldwell Banker Realty
(If provided) CoList: from

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The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than Legacy Real Estate Inc are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.