Skyline Area Homes for Sale

Welcome to the beautiful Skyline Area in Woodside, California! Nestled in San Mateo County, this neighborhood offers a tranquil and picturesque setting for those seeking a peaceful escape from the bustling city life.

Skyline Area is renowned for its natural beauty and stunning landscapes. Surrounded by lush greenery and towering trees, residents here enjoy breathtaking views of the surrounding hills and valleys. The area is also home to several hiking and biking trails, providing ample opportunities for outdoor enthusiasts to explore and connect with nature.

When it comes to real estate, the Skyline Area has a variety of homes for sale that cater to different preferences and budgets. Whether you're looking for a cozy cottage or a spacious modern estate, you'll find a range of options to choose from. Many of the homes in this area boast large lots, allowing for privacy and room to create your own oasis.

Living in the Skyline Area offers a peaceful and close-knit community atmosphere. Residents enjoy the benefits of a small-town feel while still being within easy reach of the amenities and conveniences of nearby cities. The neighborhood is also known for its top-rated schools, making it an ideal choice for families.

If you're looking for a serene and picturesque neighborhood with a strong sense of community, the Skyline Area in Woodside, CA is the perfect place to call home. Don't miss the opportunity to explore the homes for sale in this charming area and experience the beauty and tranquility it has to offer.

Newest Skyline Area Homes for Sale

$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

$1,899,950

3 Beds ⋅ 2 Baths ⋅ ML82053343 MLS

One-of-a-Kind Mountain Oasis on Spacious Sunny Lot! Charming 1930s log cabin cottage getaway with impeccable newer construction master suite addition, on fenced 1/3 acre of natural, drought resistant landscaping among dozens of majestic redwoods. Open kitchen with granite counters and new six-burner gas range. High ceilings, radiant heated hardwood and tile floors throughout. High quality finishes and attention to detail should not be overlooked. Expansive south facing deck with morning and afternoon sun provide stunning views. Large detached single car garage with EV charger, storage and attic, plus parking for multiple vehicles. Walking distance to Alice's Restaurant, Skywood Trading Post Grocery, and endless hiking/biking trails. Easy access to HWY 35 Skyline Blvd and HWY 84 Woodside Road to Silicon Valley or the coast. A welcoming neighborhood and close knit community are the inherent benefits of ownership. Old world character meets modern day amenities in an idyllic setting!

252 Blakewood WAY, Redwood City

Listed by Allen Nazari, 650-313-7619 from Park Lane Capital Inc
(If provided) CoList: from

$3,195,000

3 Beds ⋅ 3 Baths ⋅ ML82045702 MLS

Luxury retreat offers a serene escape on 9+ acres, secured by an electronic gate. Under 2 miles and just minutes to Alices restarant. Stunning style on one level, the home features dramatic light-filled interiors with an open-concept design, SOARING CEILINGS, and abundant sliding glass doors and skylights. Bamboo floors, vertical grain cabinetry, and polished concrete counters. The main rooms revolve around a central patio with a stunning heritage oak tree, while an expansive rear deck with a large spa beneath the redwoods and a sunswept front yard for gardening enhance the outdoor experience. Three privately located bedrooms, each with its own bath, ensure comfort and flexibility. An equally well-appointed ADU above the garage includes a kitchen, bath, and laundry. Total privacy directly adjacent to MidPen open space. Flat useable grounds with large vegetable garden, ample of paved parking, large ground level deck and heritage oak entertainment area for large parties. Open sunny side toward views and beauty of Redwood forest on the oposite side of the house with heated spa under the redwoods. Main house 2870 sq.ft, plus ADU 550 sq.ft., plus attached garage 525 sq.ft for total of 3945 sq.ft.

1100 Old La Honda RD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

$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

$2,999,000

4 Beds ⋅ 8 Baths ⋅ ML82017325 MLS

*NOW REDUCED FOR SALE* SKY VILLA: RE-IMAGINE ROYALTY IN THE WOODS. Sky Villa is an opportunity to dream big with unmatched grandeur & privacy. This is a bank-owned, non-livable development opportunity, approximately 70% complete, with expired permits. Buyer to verify with County of San Mateo the existence and status of any past permits and the ability to resume construction towards completion. Grand scale luxury features such as: 2-Story Lobby with Imperial Staircase | 4 levels of destinations inspire your finishing details | Library off the lobby | Two Enormous Primary Suites (one main level, one upstairs) | Multiple Offices | Immense walk-in closets | Unfinished lower levels of Rec Room, Wine Vault, Grand Loggia, & dreamy Mezzanine facing majestic Sequoia Forest | Flat rear grounds inspire a future pool & ADU | Off-street parking for the most grand events, plus 2 separate attached garages: a daily 3-car at the motor court, plus a lower level 2-car attached garage | Long the bastion for Silicon Valley founders and CEO's, Woodside blurs the line between timeless province and epicenter of wealth and innovation. SKY VILLA, prepare to take flight in one of California's most prestigious communities.

1 Reids Roost RD, Woodside

Listed by Geoffrey Nelson, 650-455-3735 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 JABEZ REALTY 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.