The Highlands / Ticonderoga Homes for Sale

Welcome to The Highlands, a picturesque neighborhood nestled in the heart of San Mateo, California. This charming area, often referred to as Ticonderoga, offers a unique blend of suburban tranquility and urban convenience, making it an ideal place to call home. Surrounded by lush greenery and stunning views of the Bay Area, The Highlands is known for its friendly community vibe and picturesque streets lined with well-maintained homes.

Residents enjoy easy access to a variety of parks and recreational areas, perfect for outdoor enthusiasts and families alike. The nearby Coyote Point Recreation Area boasts breathtaking coastal views, picnic areas, and trails for hiking and biking. The neighborhood is also conveniently located just minutes from downtown San Mateo, where you’ll find a vibrant mix of shops, restaurants, and cultural attractions.

As for homes for sale in The Highlands, prospective buyers will find a delightful array of architectural styles, from charming mid-century ranch homes to contemporary builds. Each property is thoughtfully designed, often featuring spacious yards, modern amenities, and inviting interiors. The real estate market in this area is thriving, with options that cater to various lifestyles and budgets.

Whether you are looking to settle down in a family-friendly environment or seeking a peaceful retreat with easy access to urban conveniences, The Highlands/Ticonderoga is a neighborhood that truly has it all. Explore the available homes for sale today and discover the perfect place to create lasting memories in this enchanting corner of San Mateo!

Newest The Highlands / Ticonderoga Homes for Sale

$2,398,000

3 Beds ⋅ 2 Baths ⋅ ML82065002 MLS ⋅ SM Highlands BLDG.

JUST REDUCED 90K.....Set on a quiet cul-de-sac, this 3 Bedroom 2 Bath home sits on an oversized 12,638 sq. ft. lot, blending iconic mid-century design. One of the largest level lots in the SM Highlands for expansion possibilities. The 1,360 sq foot layout flows effortlessly from living and dining spaces to outdoor entertaining areas, ideal for both everyday living and hosting large events. Floor to ceiling walls of glass w/original Mahogany wood paneling. A permitted free-standing studio with additional square footage adds flexible space for a home office, gym, or artist workshop. Recently epoxied 2-car garage floor. Resealed Foam roof. Sewer lateral replaced in 2025. Successor Trustee sale with limited disclosures. This original owner home has been cared for since 1958. Staged for the fall season with a pumpkin patch to show off the generous sized grounds! Rec center includes community pool, tennis courts, and after school programs. Sawyer Camp Road close by for walking, jogging, plus bike trails along the Crystal Springs reservoir. Close to Highlands Elementary School. In the Aragon High School district. Location! Location! Location!

2015 Ticonderoga DR, San Mateo

Listed by Glenn Sennett, 650-208-7355 from Coldwell Banker Realty
(If provided) CoList: from

$2,788,000

4 Beds ⋅ 2 Baths ⋅ ML82064607 MLS ⋅ Highlands Community BLDG.

For the first time since 1967, this charming San Mateo mid-century home, cherished by its original owners since it was built, is now being offered. Set on an expansive, approximately 16,886-square-foot lot, the home is filled with natural light and offers scenic views toward Crystal Springs Reservoir and the Coastal Range. With approximately 1,770 square feet of living space, it features 4 bedrooms, 2 bathrooms, and a well-proportioned layout with wonderful potential to make it your own. The private, resort-style backyard is ideal for relaxing and entertaining, with a swimming pool, spacious poolside entertaining area, and secluded hot tub just outside the primary suite. A rare three-car garage, abundant storage, and ample driveway parking add to the home's appeal. Nestled in the San Mateo Highlands neighborhood, residents enjoy a strong sense of community, access to the Highlands Recreation Center and Highlands Elementary School, and beloved neighborhood traditions, including the annual Fourth of July parade and fireworks. A rare opportunity to make this special home your own in one of San Mateo's most welcoming communities. Your next chapter starts here- welcome home!

1245 Laurel Hill DR, San Mateo

Listed by Justin Schneider, 650-224-4428 from Intero Real Estate Services
(If provided) CoList: from

$4,498,000

3 Beds ⋅ 2 Baths ⋅ ML82060534 MLS ⋅ The Highlands BLDG.

A rare architectural offering, this one-of-a-kind 1956 Mid-Century Modern X-100 prototype, designed by an acclaimed team of architects, represents a pivotal moment in mid-century modern design. The home showcases six exposed steel I-beams, eliminating interior load-bearing walls and creating a dramatic open, light-filled environment with seamless indoor-outdoor flow. Thoughtfully restored while honoring its original vision, recent updates include fresh interior/exterior paint, recoated foam roof, refinished vinyl and concrete floors, updated radiant heating, curated furnishings, and refreshed landscaping. The home is organized around two private garden atriums with in-ground planting beds, while 32 feet of skylights flood the interiors with natural light. Signature materials, steel, glass, and Formica, highlight the home's authentic modernist character. Built-ins and kitchen elements are fully integrated into the architecture. Debuted in 1956, the X-100 gained national attention and influenced generations of modern residential design, set against the backdrop of Crystal Springs Reservoir. Listed on the National Register, this is a true collector-grade property ideal for design enthusiasts, historians, and those seeking a singular living experience. A legacy of visionary design.

1586 Lexington AVE, San Mateo

Listed by Boyenga Team, 408-373-1660 from Compass
(If provided) CoList: Graeham Watts from Compass

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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.

The Highlands / Ticonderoga Homes for Sale

Newest The Highlands / Ticonderoga Homes for Sale

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