San Mateo Highlands Homes

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  /78

  $2,298,000 Open Sat 1:30PM - 4:30PM

  • 4 Beds
  • 3 Baths
  • 1,890 Sq Ft

  2055 Ticonderoga Dr, San Mateo, CA 94402

  Stunning 4-bedroom, 3-bath courtyard model Eichler on a rare 9,600± sq ft lot in San Mateos coveted Highlands. This architectural gem blends timeless Eichler design with modern updates, creating a home that is both iconic and highly livable. Soaring tongue-and-groove ceilings, dramatic post-and-beam lines, and signature floor-to-ceiling glass flood the interiors with natural light while framing

  Boyenga Team Compass

  2055 Ticonderoga Dr, San Mateo, CA 94402
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  Explore San Mateo Highlands

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  /40

  $2,700 - $3,450 per month

  Hillside Gardens

  1 - 2 Beds

  810 Polhemus Rd, San Mateo, CA 94402

  Surrounded on three sides by forested hillsides, enjoy the peaceful and breathtaking views of the San Mateo Hills while you lounge at our resort-style pool and sundeck. Our spacious one- and two-bedroom floor plans feature large private patios, high ceilings, and generous windows. Two large interior courtyards with mature trees are wonderful for pets and their people to play in! Appreciate the

  810 Polhemus Rd, San Mateo, CA 94402
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  /80

  $3,950,000 Sold Sep 10, 2025

  • 3,390 Sq Ft
  • $1,165/SF
  • 33 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2022

  2185 Cobblehill Place, San Mateo, CA 94402

  Discover the perfect blend of luxury, comfort, & California living at 2185 Cobblehill Place, nestled in the highly sought-after Highlands neighborhood of San Mateo. Situated on a sprawling 17,997 sq ft lot, this beautifully crafted home features 4 bedrooms, 3.5 bathrooms, & 3,390 sq ft of thoughtfully designed living space. Expansive picture windows in the light-filled living & dining areas frame

  Disen Cai KW Advisors

  2185 Cobblehill Place, San Mateo, CA 94402
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  /29

  Est $2,803,228 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,860 Sq Ft

  1284 Laurel Hill Dr, San Mateo, CA 94402

  1284 Laurel Hill Dr, San Mateo, CA 94402
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  /69

  $1,975,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,670 Sq Ft

  30 White Plains Ct, San Mateo, CA 94402

  Tucked at the end of a quiet cul-de-sac on a spacious, level 9,635 sq. ft. lot, this 4-bedroom, 2-bath Eichler blends iconic mid-century modern architecture with exciting potential. Signature Eichler features include post-and-beam construction, a brick fireplace, and an open-concept layout that seamlessly connects indoor and outdoor living. The original kitchen and bathrooms are ready for your

  Ranya Kaileh Francis Sotheby's Intl Rlty

  30 White Plains Ct, San Mateo, CA 94402
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  /2

  $2,850,000 Sold Sep 08, 2025

  • 1,710 Sq Ft
  • $1,667/SF
  • 4 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1958

  1984 Ticonderoga Dr, San Mateo, CA 94402

  Welcome to the San Mateo Highlands Sleek Modern Mid-century Eichler home! Four-bedroom, Two-bathroom plus highly desirable atrium floor plan. Spanning a comfortable 1,710 square feet, this property offers an open concept living space with radiant floor heating and additional heating/AC zones for ideal temperature control. The modern kitchen is equipped with quartz countertops, a built-in oven,

  Glenn Sennett Coldwell Banker Realty

  1984 Ticonderoga Dr, San Mateo, CA 94402
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  /60

  Est $2,584,166 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  1268 Laurel Hill Dr, San Mateo, CA 94402

  1268 Laurel Hill Dr, San Mateo, CA 94402
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  /38

  $2,398,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft

  1531 Forge Rd, San Mateo, CA 94402

  Built in 1959 by the renowned builder Joseph Eichler, this home stands as a testament to his mid-century modern design philosophy. Located on a generous size lot, the updated home remains a pristine example of Eichlers vision of boldness, change, and optimism offering superb indoor-outdoor living. Freshly painted inside and out, the home begins with a signature atrium that serves as a central

  Charles Krakow Krakow Company

  1531 Forge Rd, San Mateo, CA 94402
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  /2

  $2,340,000 Sold Sep 08, 2025

  • 2,040 Sq Ft
  • $1,147/SF
  • 36 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1956

  1652 Lexington Ave, San Mateo, CA 94402

  Architectural Gem with Panoramic Views in the Coveted Highlands Perched in the highly desirable Highlands neighborhood, this rare Eichler is a striking example of mid-century modern design elevated for contemporary living. With sweeping panoramic views and professionally designed landscaping, the home offers a serene retreat that seamlessly blends indoor and outdoor spaces. The well-designed

  Lisa Karson Golden Gate Sotheby's International Realty

  1652 Lexington Ave, San Mateo, CA 94402
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  /43

  Est $2,547,747 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,860 Sq Ft

  2096 Ticonderoga Dr, San Mateo, CA 94402

  2096 Ticonderoga Dr, San Mateo, CA 94402
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  /41

  $1,925,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,660 Sq Ft

  2224 Bunker Hill Dr, San Mateo, CA 94402

  Commanding views from this highly coveted classic Eichler home, nestled in the picturesque San Mateo Highlands. Set on an expansive 8,330sf lot, this home backs to open space, providing breathtaking views. True to Eichlers signature style, the open floor plan and walls of glass invite abundant natural light while creating a harmonious indoor-outdoor living experience. The living room exudes

  Laura Bertolacci Christie's International Real Estate Sereno

  2224 Bunker Hill Dr, San Mateo, CA 94402
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  /121

  $2,700,000 Sold Jul 31, 2025

  • 1,550 Sq Ft
  • $1,742/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1956

  1651 Lexington Ave, San Mateo, CA 94402

  NEW MODERN EICHLER IN SAN MATEO HIGHLANDS Completed in 2020, this MCM home had a radical remodel integrating new materials and technologies while preserving architectural integrity. Curb appeal is a 10. Colorful, textured landscaping with the ebony Eichler is captivating and the emerald courtyard preceding the front door, delightful. Inside, the white interior has beamed ceilings, engineered

  Julie Baumann Compass

  1651 Lexington Ave, San Mateo, CA 94402
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  /59

  Est $2,609,302 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,740 Sq Ft

  2096 Lexington Ave, San Mateo, CA 94402

  2096 Lexington Ave, San Mateo, CA 94402
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  /27

  $2,200,000 Sold Jun 12, 2025

  • 1,590 Sq Ft
  • $1,384/SF
  • 32 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1957

  2104 Lexington Ave, San Mateo, CA 94402

  Mid-Century Modern enthusiasts will be delighted with this meticulously maintained Eichler. This special home features 3 bedrooms, 2 full bathrooms, front entry courtyard, gorgeous high ceilings, great natural light and unobstructed views of the mountains (no backyard neighbors). Recent improvements include: newer foam roof, exterior paint, Pella Impervia energy-efficient (fiberglass) windows and

  Monique Anton Modern Homes Realty

  2104 Lexington Ave, San Mateo, CA 94402
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  /55

  Est $2,463,381 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,830 Sq Ft

  1968 Ticonderoga Dr, San Mateo, CA 94402

  1968 Ticonderoga Dr, San Mateo, CA 94402
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  /96

  $2,665,000 Sold Jun 11, 2025

  • 2,087 Sq Ft
  • $1,277/SF
  • 4 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1965

  1251 Laurel Hill Dr, San Mateo, CA 94402

  Your Dream Home Awaits at 1251 Laurel Hill Drive- Where Style Meets Serenity, this ranch-style retreat nestled in the San Mateo Highlands will have you falling in love with every detail. This 4BD/3BA home combines warmth, modern upgrades, and canyon views into a space that feels both elevated and grounded. The open-concept kitchen is a showstopper, featuring custom maple cabinetry, quartzite

  Olivia Mcnally Real Brokerage Technologies

  1251 Laurel Hill Dr, San Mateo, CA 94402
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  /22

  Est $2,668,741 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft

  2023 Ticonderoga Dr, San Mateo, CA 94402

  2023 Ticonderoga Dr, San Mateo, CA 94402
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  /63

  $2,400,000 Sold May 23, 2025

  • 1,630 Sq Ft
  • $1,472/SF
  • 8 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1965

  1719 Yorktown Rd, San Mateo, CA 94402

  Tranquil coastal mountain views frame this beautifully remodeled, modern single-story Eichler home in a prime location. Featuring 4 bedrooms, 2 remodeled baths, and Eichlers signature post-and-beam construction, vaulted ceilings, and floor-to-ceiling glass, this home seamlessly connects indoor and outdoor living. The open-plan kitchen flows into a family room, with a formal dining room and

  Sheldon Rilliet Compass

  1719 Yorktown Rd, San Mateo, CA 94402
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  /33

  Est $2,200,646 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,490 Sq Ft

  2264 Sheraton Place, San Mateo, CA 94402

  2264 Sheraton Place, San Mateo, CA 94402
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  /53

  $2,475,000 Sold May 16, 2025

  • 1,550 Sq Ft
  • $1,597/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1956

  1796 Lexington Ave, San Mateo, CA 94402

  Spectacular views of the open space! Sleek San Mateo Highlands remodel! Three bedrooms two baths plus family room. Soaring ten-foot-high ceilings with walls of glass. Light filled home gives off a feeling of serenity throughout the house. Double pane windows. 180 degrees of views of open space and coastal mountain range. Updated bamboo cabinets in the modern open kitchen concept. Stainless steel

  Glenn Sennett Coldwell Banker Realty

  1796 Lexington Ave, San Mateo, CA 94402
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  /43

  Est $3,390,657 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,661 Sq Ft

  45 Lundys Ln, San Mateo, CA 94402

  45 Lundys Ln, San Mateo, CA 94402
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  /77

  $2,800,000 Sold May 13, 2025

  • 3,030 Sq Ft
  • $924/SF
  • 36 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1956

  1760 Lexington Ave, San Mateo, CA 94402

  $200,000 PRICE ADJUSTMENT..Mid-century modern Highlands Eichler! Spacious two-story San Mateo Highlands Eichler home w/amazing views of the coastal mountains and Crystal Springs reservoir. Backs up to the open space for superior location and privacy. Beautiful Landscaped 8,030 square foot lot with the feel of your own park behind the house. One of the largest Eichler Highlands homes to have been

  Glenn Sennett Coldwell Banker Realty

  1760 Lexington Ave, San Mateo, CA 94402
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  /42

  Est $2,789,565 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft

  1547 Tarrytown St, San Mateo, CA 94402

  1547 Tarrytown St, San Mateo, CA 94402
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  /2

  $2,885,000 Sold May 02, 2025

  • 2,510 Sq Ft
  • $1,149/SF
  • 12 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1976

  65 Bennington Dr, San Mateo, CA 94402

  OFFERS DUE WEDNESDAY APRIL 16TH BY 12NOON - This home comes bearing gifts - not just in features, but in lifestyle! From peaceful hillside views to a sun-soaked patio with fruit bearing trees and a raised garden bed, every corner invites you to savor home life. Picture afternoons by the pool and evenings under the stars with the hillside as your backdrop. Inside, comfort meets style in a

  Chris Eckert KW Advisors

  65 Bennington Dr, San Mateo, CA 94402
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  /25

  Est $4,465,128 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,610 Sq Ft

  57 Roxbury Ln, San Mateo, CA 94402

  57 Roxbury Ln, San Mateo, CA 94402
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  /35

  $2,600,000 Sold May 02, 2025

  • 2,550 Sq Ft
  • $1,020/SF
  • 13 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1976

  2184 Bunker Hill Dr, San Mateo, CA 94402

  FIRST TIME ON MARKET! A stylish and beautifully maintained Whitecliff home offering generous space and an abundance of natural light. Large eat-in kitchen, primary bedroom suite, downstairs family room, indoor laundry, and 2-car garage. Dramatic high ceilings in the main living area, fireplaces in both living and family rooms, ample storage and inviting rear deck surrounded by sport court and

  Karyl Eldridge Coldwell Banker Realty

  2184 Bunker Hill Dr, San Mateo, CA 94402
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  /37

  Est $3,013,715 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,040 Sq Ft

  1296 Laurel Hill Dr, San Mateo, CA 94402

  1296 Laurel Hill Dr, San Mateo, CA 94402
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  /54

  $2,850,000 Sold Apr 01, 2025

  • 1,779 Sq Ft
  • $1,602/SF
  • 7 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1958

  2018 Ticonderoga Dr, San Mateo, CA 94402

  Stunning, recently renovated mid-century modern Highlands Eichler situated on a generous 8,500+ sq ft lot along one of the neighborhoods most desirable streets. Expansive, soaring windows flood the home with natural light while maintaining exceptional privacy. A versatile new addition offers endless possibilities: perfect as a bedroom suite with a home office, au pair quarters, or even an ADU.

  Michael Talis Coldwell Banker Realty

  2018 Ticonderoga Dr, San Mateo, CA 94402
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  /36

  Est $2,882,898 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,190 Sq Ft

  2024 New Brunswick Dr, San Mateo, CA 94402

  2024 New Brunswick Dr, San Mateo, CA 94402
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  /43

  $2,600,000 Sold Mar 17, 2025

  • 1,640 Sq Ft
  • $1,585/SF
  • 10 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1956

  1990 Lexington Ave, San Mateo, CA 94402

  This four-bedroom, two-bathroom Mid-century Eichler home offers approximately 1,640 square feet of living space. With a private location on a 8,250 square foot level lot, backs up to open space w/views of the coastal mountains. Features an in-ground pool, providing a refreshing outdoor retreat. Open concept living room w/fireplace has 10 foot high ceilings looking out to serene views! The primary

  Glenn Sennett Coldwell Banker Realty

  1990 Lexington Ave, San Mateo, CA 94402
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  /70

  Est $3,068,740 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,360 Sq Ft

  2012 New Brunswick Dr, San Mateo, CA 94402

  2012 New Brunswick Dr, San Mateo, CA 94402
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  /21

  $2,600,000 Sold Mar 13, 2025

  • 1,760 Sq Ft
  • $1,477/SF
  • 12 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1959

  20 Hoods Point Way, San Mateo, CA 94402

  Amazing remodeled Eichler located on a private quiet street with serene views and an extremely large yard. Step into this zen space that features 4 bedrooms, 2 bathrooms, and 1,760 SqFt of living space on a large 7,875 SqFt lot. Other features of this special home include floor to ceiling windows in the front and rear of the home that fill the space with great natural light, an open kitchen with

  Monique Anton Modern Homes Realty

  20 Hoods Point Way, San Mateo, CA 94402
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  /27

  Est $2,513,659 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft

  1783 Lexington Ave, San Mateo, CA 94402

  1783 Lexington Ave, San Mateo, CA 94402
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  /48

  $3,310,000 Sold Mar 06, 2025

  • 2,510 Sq Ft
  • $1,319/SF
  • 8 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1976

  55 Bennington Dr, San Mateo, CA 94402

  OFFERS DUE WEDNESDAY FEBRUARY 12TH BY 12NOON - This 4-bedroom home offers spacious living with a versatile open loft, perfect for a home office or playroom. The 2.5 bathrooms include a luxurious ensuite with a walk-in closet, separate bathing area, sit-down vanity, while the second bath features a jacuzzi tub for a spa-like retreat. The kitchen and great room are the heart of the home: stainless

  Chris Eckert KW Advisors

  55 Bennington Dr, San Mateo, CA 94402
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  /50

  Est $2,697,088 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft

  1555 Tarrytown St, San Mateo, CA 94402

  1555 Tarrytown St, San Mateo, CA 94402
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  /10

  $1,900,000 Sold Dec 13, 2024

  • 1,400 Sq Ft
  • $1,357/SF
  • 7 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1959

  40 Lundys Ln, San Mateo, CA 94402

  Great location in the highly sought-after San Mateo Highlands community! This original-condition Eichler sits at the end of a private cul-de-sac on a spacious lot, offering breathtaking panoramic views from the back patio and nearly every room. Enjoy the convenience of being just a short distance from excellent dining, shopping, and scenic hiking and biking trails.

  Anson Ip Compass

  40 Lundys Ln, San Mateo, CA 94402
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  /47

  Est $2,546,614 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,720 Sq Ft

  1587 Tarrytown St, San Mateo, CA 94402

  1587 Tarrytown St, San Mateo, CA 94402
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  /45

  $2,650,000 Sold Dec 11, 2024

  • 1,660 Sq Ft
  • $1,596/SF
  • 3 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1959

  1523 Tarrytown St, San Mateo, CA 94402

  Move in and enjoy this beautiful four bedroom single-story home nestled near Crystal Springs Reservoir and Hillsborough. Spacious 9,020 SF lot. Private and covered front courtyard including dining deck patio. Beautifully renovated throughout. New floors. Open kitchen with breakfast bar island & Stainless steel appliances. Two dining areas. Bright living area and sitting room. Large primary suite

  David Lillo DPL Real Estate

  1523 Tarrytown St, San Mateo, CA 94402
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  /42

  Est $2,459,277 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft

  5 W Point Place, San Mateo, CA 94402

  5 W Point Place, San Mateo, CA 94402
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  $2,856,750 Sold Nov 27, 2024

  • 1,720 Sq Ft
  • $1,661/SF
  • 19 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1958

  1539 Forge Rd, San Mateo, CA 94402

  Welcome to this beautifully remodeled Eichler home. Set in the highly desirable San Mateo Highlands, this mid-century modern masterpiece has been thoughtfully updated to perfectly blend modern comforts with the iconic Eichler design. As you step inside, natural light pours through expansive floor-to-ceiling windows, filling the home with a bright, open ambiance. The spacious, open-concept layout

  Amanda Elhassan Keller Williams Tri-valley

  1539 Forge Rd, San Mateo, CA 94402

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