Skyline Area Homes with Bay View

Welcome to the Skyline Area of Woodside, California—a hidden gem nestled in the picturesque San Mateo County. Known for its breathtaking vistas and serene ambiance, this neighborhood offers an unparalleled living experience that seamlessly blends nature with luxury.

The Skyline Area is renowned for its stunning homes that boast panoramic views of the San Francisco Bay and the rolling hills that define the region. Imagine waking up each morning to the sun rising over the bay, casting a warm glow across your spacious deck or patio. These homes are not just residences; they are sanctuaries where tranquility reigns supreme. With properties ranging from modern architectural masterpieces to charming rustic retreats, there is something for every discerning homeowner.

Nature enthusiasts will find their paradise here, with an abundance of hiking and biking trails just a stone's throw away. The nearby Purisima Creek Redwoods Preserve offers a chance to immerse yourself in the beauty of towering redwoods and lush landscapes, making it a perfect spot for weekend adventures or peaceful strolls.

Despite its serene setting, the Skyline Area is conveniently located just minutes from the vibrant culture and amenities of downtown Woodside and nearby cities. Fine dining, boutique shopping, and top-rated schools are all within easy reach, providing the perfect balance of rural charm and urban convenience.

Experience the allure of the Skyline Area, where breathtaking bay views and a close-knit community await you. Discover your dream home in this enchanting neighborhood today!

Newest Skyline Area Homes with Bay View

$2,870,000

7 Beds ⋅ 6 Baths ⋅ ML82039818 MLS

A rare opportunity to own an expansive estate with breathtaking panoramic views, exceptional square footage, and incredible potential in a private hillside setting. From the moment you arrive, the home commands attention with its grand entry and impressive scale. Inside, soaring ceilings, dramatic open spaces, and walls of windows flood the home with natural light while showcasing sweeping valley views. The main level is built for both everyday living and entertaining, featuring a spacious living room, multiple gathering areas, and seamless access to a wraparound deckperfect for true indoor-outdoor living. The kitchen offers a large island, ample cabinetry, and a functional layout ready to be elevated into a stunning chefs space. Generous bedrooms and flexible living areas include a primary suite with scenic windows, dual vanities, and a soaking tub, creating a peaceful retreat with beautiful natural surroundings. The lower level offers an expansive bonus/game room with bar area and endless possibilities for entertaining, recreation, or extended living. A dedicated wine cellar adds a rare and desirable touch. Expansive decking and usable outdoor space complete this exceptional offering, blending privacy, scale, and opportunity in a truly unique setting.

245 Heacox RD, Woodside

Listed by Aaron Derbacher, 408-828-8114 from KW Bay Area Estates
(If provided) CoList: Benjamin Frieden from KW Bay Area Estates

$2,195,000

3 Beds ⋅ 3 Baths ⋅ ML82042155 MLS

Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes from Highway 280. A palatial driveway leads to a two-story, 3-bedroom, 3-bath, open-plan residence with walls of windows capturing the rolling hill and city-light views. Almost every room has glass doors to the long, view balcony. Lawn and mini orchard. A separate charming barn captures the Old West Woodside feel with a wood-beamed ceiling, full-sized bar, and French doors to a veranda with flowering vines. Just a mile to the Thomas Fogarty Winery and 8 minutes to Alice's Restaurant.

20255 Skyline BLVD, Woodside

Listed by Jennifer Paulson, 650-996-7147 from Christie's International Real Estate Sereno
(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 Fine Group Real Estate 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.