Skyline Area Homes with Bay View

Welcome to the Skyline Area, a breathtaking enclave nestled in the heart of Woodside, California, within the picturesque San Mateo County. This charming neighborhood is renowned for its stunning vistas, where panoramic views of the San Francisco Bay meet the majestic backdrop of the Santa Cruz Mountains. Imagine waking up to the gentle glow of the sunrise casting a golden hue over the bay—this is the everyday reality for residents of Skyline.

The Skyline Area is a haven for nature lovers and outdoor enthusiasts, with an abundance of hiking and biking trails that wind through lush forests and serene landscapes. The nearby Purisima Creek Redwoods Preserve offers miles of trails that beckon you to explore the towering redwoods and vibrant flora. Whether you enjoy a leisurely stroll or an adventurous hike, the natural beauty surrounding Skyline is simply unparalleled.

Homes in this area are unique and diverse, often featuring spacious lots and breathtaking views of the bay. Many properties boast expansive decks and large windows designed to capture the stunning vistas, creating an inviting atmosphere for entertaining or simply relaxing in your own private retreat. The architectural styles range from charming cottages to luxurious estates, ensuring there’s something for everyone.

In addition to its natural beauty, the Skyline Area is conveniently located near top-rated schools, boutique shops, and gourmet dining options in nearby Woodside and Redwood City. With its perfect blend of tranquility and accessibility, the Skyline Area is not just a place to live; it’s a lifestyle choice that embodies the best of California living. 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

Start Your Search

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 Christie's International Real Estate Sereno 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.