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1586 Lexington AVE, San Mateo
$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

1719 Monticello RD, San Mateo
$3,200,000
4 Beds ⋅ 3 Baths ⋅ ML82053530 MLS
This expanded 2,020 sq. ft. mid-century modern home delivers a move-in-ready experience in the sought-after San Mateo Highlands. The 4-bed, 3-bath layout features exposed beams, dual pane windows, and brand-new premium rigid plank flooring throughout. The fully remodeled open-concept kitchen is anchored by a Bosch induction range, sleek quartz countertops, and handmade Fireclay tile. All 3 baths are completely updated with premium Toto toilets; the primary en-suite offers radiant heated floors. The finished 2-car garage studio features commercial-grade epoxy floors, ideal for a workspace or gym. Seamless indoor-outdoor living is achieved via a 9-foot Fleetwood sliding glass door opening to a custom Seed Studio landscape. This low-maintenance native and artificial turf yard is an entertainers highlight, featuring an arbor dining area, built-in Bromic heater, Lynx outdoor grill, and custom Concreteworks fire pit. Foundational infrastructure is modernized: a 200-amp panel, EV charger, replaced sewer lateral, and new 3-ply roof recoat over a foam base. Efficiency is maximized with a 7.2 kW NEM 2.0 solar system, Nest, Ring, and Rachio. Residents enjoy Highlands Rec Center access, After-School priority, and efficient San Francisco/Silicon Valley commutes.

1719 Monticello RD, San Mateo

Listed by William Fox, 650-576-6124 from Berkshire Hathaway HomeServices DrysdaleProperties
(If provided) CoList: from

Sold listing courtesy of Austin Herman from APR

2027 New Brunswick DR, San Mateo
$3,100,000
4 Beds ⋅ 2 Baths ⋅ ML82042371 MLS
Classic Eichler design meets sweeping Bay views in this beautifully updated San Mateo Highlands home. Expansive walls of glass frame panoramic vistas and fill the home with natural light, creating a seamless indoor-outdoor living experience. From sunrise to sunset, the home's elevated setting offers a rare sense of openness, privacy, and connection to the surrounding landscape. Spanning 1,856sf on an 8,250sf lot, the home showcases Eichler's signature open floor plan, vaulted ceilings, and clean mid-century lines. The layout flows effortlessly from living and dining spaces to outdoor entertaining areas, ideal for both everyday living and hosting. Thoughtfully upgraded, the home blends iconic design with modern comfort. Features include porcelain tile flooring, remodeled primary bath, curated designer lighting, and a gas fireplace with tile surround. The kitchen is enhanced with a glass tile backsplash, while upgraded electrical with EV charging, new garage doors and systems, and integrated audio add convenience and functionality. Set in the SM Highlands, the property offers a quiet, private setting with easy access too 1-280, SFO, Highway 92 and nearby amenities such as a community pool, pickle ball/tennis, playground. A rare opportunity to enjoy exceptional Bay view living.

2027 New Brunswick DR, San Mateo

Listed by Kathleen Azzopardi, 650-868-2878 from Compass
(If provided) CoList: Eddie Azzopardi from Compass

Sold listing courtesy of Kyle Rawls from AGNC

637 Vanessa DR, San Mateo
$2,300,000
3 Beds ⋅ 2 Baths ⋅ ML82037035 MLS ⋅ 19th Ave Park BLDG.
A rare opportunity to own a beautifully remodeled, move-in-ready Eichler in the heart of San Mateo. This light-filled residence showcases classic mid-century modern design enhanced with contemporary upgrades that preserve the homes architectural character. The open-concept floor plan centers around a remodeled kitchen and updated baths, complemented by engineered hardwood flooring and dual-pane windows. Energy efficiency and sustainability come together with a foam roof, owned solar, 3 Tesla Powerwalls, and all-electric heat pump system. The home offers a spacious primary suite with an ensuite bath and 3 additional bedrooms ideal for family, guests, or a home office. The 4th bedroom is currently open to the living area, creating an airy flexible space that can easily be converted back. Indoor-outdoor living takes center stage with floor-to-ceiling glass and 3 sliding doors that open to a new concrete patio, perfect for entertaining. A spacious backyard offers space for outdoor gatherings, creating a seamless extension of the living space. Ideally located on the Peninsula, the home offers exceptional convenience with easy access to SFO, Caltrain, 101, 92, and 280. Major tech employers including YouTube, Meta, Snowflake, and Google are within easy reach of this 19th Ave. Park Gem.

637 Vanessa DR, San Mateo

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

Sold listing courtesy of Todd Montgomery from COMP12

678 Connie AVE, San Mateo
$2,200,000
3 Beds ⋅ 2 Baths ⋅ ML82037348 MLS
Welcome to 678 Connie Ave in San Mateo a beautifully updated 3 bedroom, 2 bathroom, 1440 sqft Eichler-style home in the desirable Nineteenth Park community. Showcasing classic mid-century design, it features dramatic floor-to-ceiling windows that fill the space with natural light and connect indoor and outdoor living. Designed for modern living, the home offers an open kitchen, dining, and living floor plan ideal for everyday living and entertaining. Brand-new engineered hardwood floors and radiant heating run throughout, providing warmth and comfort. The updated kitchen features a large island, stainless steel farmhouse sink, designer tile backsplash, top-of-the-line BOSCH range, built-in microwave, and generous prep and seating space all open to the main living areas. The spacious primary bedroom includes a private ensuite and direct yard access. Two additional bedrooms offer flexibility for guests, a home office, or growing needs. Additional upgrades include new air conditioning, fresh paint, epoxy garage floors, and a spacious 2-car garage. Fresh landscaping enhances curb appeal. Centrally located near Trader Joe's, Whole Foods, Hillsdale Shopping Center, and Bridgepointe with easy access to Highway 92, this home offers a perfect balance of style, comfort, and location.

678 Connie AVE, San Mateo

Listed by OWN Real Estate, 650-888-0153 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of OWN Real Estate from KWPEN

2096 Ticonderoga DR, San Mateo
$2,750,000
5 Beds ⋅ 3 Baths ⋅ ML82030158 MLS
Beautiful remodeled Eichler w/mid-century architecture & modern updates & rare expansive flat yard. Classic Eichler elements: soaring wooden & beam ceilings, A formal entry to spacious liv.rm w/high ceilings, beams, a brick accent wall a wood-burn fireplace. The kitchen is a striking modern showpiece w/high-gloss fire-engine red & white cabinetry. Granite countertops,5 burner gas cooktop, sleek hood, built-in oven, trash compactor. Oversized commercial-style refrigerator is flanked by pantry storage.The eat-in dining area connects to the front yard. Off the kitchen is a separate family or private bdrm. w/flexible living space. A full modern bath w/stall shower. Perfect for media or extended living. The bedrm wing includes 4-bedrms; 1 bdrm is used as a (home office) w/skylight. The primary suite w/spacious closet & a sliding door that opens to the yard. Remodeled bath w/a shower & tile floors. The newly renovated contemporary hallway bath. w/a suspended floating vanity, dramatic dark tile floors & green tiled accent wall. W&D located in the hallway. Front yard w/custom pergola, & lush landscaping. Bonus hobby studio approx.215 sq. ft. Nest thermostat, newer boiler system & sewer lateral, 22 owned solar panels. Showcased in Eichler Mag. & The Almanac for weekend brunch"Table for 6"

2096 Ticonderoga DR, San Mateo

Listed by Debbie Wilhelm, 650-400-3111 from Coldwell Banker Realty
(If provided) CoList: Roy Barba from Coldwell Banker Realty

Sold listing courtesy of James Shinbori from COMP90

2055 Ticonderoga DR, San Mateo
$2,425,000
4 Beds ⋅ 3 Baths ⋅ ML82019751 MLS ⋅ Highlands BLDG.
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 sweeping mountain views. The flexible layout includes two primary suites and three full baths, offering ideal space for multigenerational living, guests, or a private home office. A central courtyard serves as the heart of the homeperfect for entertaining or peaceful relaxation. Recent updates include fresh interior and exterior paint, brand new SPC flooring, an updated kitchen with sleek finishes and new stainless appliances, refreshed baths, new accent lighting alongside original globe fixtures, and fresh landscaping. Original Eichler elementsradiant heat, a floor-to-ceiling brick fireplace, and seamless indoor-outdoor flowpreserve the homes architectural authenticity. Enjoy the Highlands lifestyle with access to the Recreation Center (pool, tennis, fitness), nearby hiking trails, and excellent schools: Highlands Elementary, Borel Middle, and Aragon High (buyer to verify).

2055 Ticonderoga DR, San Mateo

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

Sold listing courtesy of Janelle Boyenga from COMPS

1636 Celeste DR, San Mateo
$2,100,000
4 Beds ⋅ 2 Baths ⋅ ML82018853 MLS
Step into this beautifully remodeled 4-bedroom, 2-bathroom Eichler home in San Mateo's sought-after 19th Avenue Park neighborhood. With its iconic mid-century modern design, this residence captures the timeless spirit of Joseph Eichler while blending in modern updates for today's lifestyle. Inside, you'll find an open-concept floor plan with an additional family room, providing both versatility and comfort. The expansive living spaces are filled with natural light through new double-pane windows and flow seamlessly into the private side yard; perfect for indoor/outdoor entertaining. Classic Eichler hallmarks shine throughout, including clean lines, post-and-beam construction, and a strong connection to the outdoors. The home has been thoughtfully remodeled with contemporary finishes, while preserving its original character and charm. Set in a welcoming neighborhood with tree-lined streets and a strong sense of community, this home offers both lifestyle and convenience. Enjoy easy access to nearby parks, schools, local shops, and restaurants. With close proximity to Highway 92, 101, and Caltrain, commuting to San Francisco, Silicon Valley, or East Bay is a breeze. Don't miss the opportunity to own a classic Eichler that perfectly balances mid-century character with modern living.

1636 Celeste DR, San Mateo

Listed by Alex Lam, 415-860-5092 from Compass
(If provided) CoList: Kristle Lam from Compass

Sold listing courtesy of Amy Wang from CBR

1984 Ticonderoga DR, San Mateo
$2,850,000
4 Beds ⋅ 2 Baths ⋅ ML82017563 MLS ⋅ SM Highlands BLDG.
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, self-cleaning features, and energy-efficient Stainless steel appliances including dishwasher and microwave. Skylights in the dining area and kitchen add natural light to the interiors. The home's flooring is a mix of elegant hardwood and tile, complemented by the warmth of a fireplace in the dining area. Views of the coastal mountains is a plus on this private 8,130 sq foot mostly level lot which includes, a spa/hot tub and sauna, enhancing your relaxation experience plus two gazebos and two decks. Cumaru wood is used on the primary deck. With double-pane windows and solar power features, this home is a blend of comfort and efficiency. Walking distance to the rec center w/community pool, tennis/pickle ball, after school programs, playground, & daycare. Close to Hwy 280 and 92 for easy commuting to Silicon valley jobs. 5 minutes to Sawyer Camp Road for biking, jogging, walking trails.

1984 Ticonderoga DR, San Mateo

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

Sold listing courtesy of Mani Singh Bhachu from CBR

1652 Lexington AVE, San Mateo
$2,340,000
3 Beds ⋅ 3 Baths ⋅ ML82014403 MLS
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 floor plan features three private en suite bedrooms, each with its own entrance, secluded outdoor patio, and dusk-to-dawn lightingideal for hosting guests, multi-generational living, or income-generating opportunities such as Airbnb or extended stays. Thoughtfully updated and impeccably maintained, the home reflects pride of ownership and meticulous attention to detail. From timeless architectural lines to modern finishes, every element is curated for both comfort and style. Adding to its versatility is a permitted ~500 sq. ft. finished bonus area (not reflected in county records), perfect for a home office, creative studio, fitness room, or peaceful retreat. The garage has been converted to a flexible space and can be easily restored if desired. More than just a residence, this is a rare lifestyle opportunity in one of the regions most sought-after communities.

1652 Lexington AVE, San Mateo

Listed by Lisa Karson, 650-759-4644 from Golden Gate Sotheby's International Realty
(If provided) CoList: Pamela Merkadeau from Coldwell Banker Realty

Sold listing courtesy of Ashley Hwang from FIHI

636 Connie AVE, San Mateo
$2,100,000
5 Beds ⋅ 3 Baths ⋅ ML81971892 MLS ⋅ 19th Avenue Park BLDG.
Experience the epitome of modern living in this stunningly remodeled Eichler home, where contemporary design meets timeless architecture. Expanded two years ago by the owner into their dream house, this move-in-ready gem has been thoughtfully updated throughout, featuring brand-new central heating and air conditioning, new exterior wall insulation, and an upgraded 200-amp electrical panel. The kitchen is a chef's dream, boasting custom wood-tone cabinets and a well-proportioned island, perfect for breakfast or evening drinks. Designed to enhance the iconic indoor-outdoor lifestyle of California, this home features an open-concept floor plan with abundant natural light. The spacious living areas flow seamlessly from the kitchen to the dining and living rooms, all accentuated by floor-to-ceiling glass walls that blur the lines between indoor and outdoor spaces. The yard, connected to the living room, is an oasis of outdoor living, ideal for relaxation and entertaining. Enjoy the convenience of a neighborhood park just steps away, along with nearby amenities such as Trader Joe's, Costco, Ranch 99, local restaurants, shops, the YMCA, and more. Easy access to major transportation routes, including HWY 92 and 101, ensures seamless connectivity.

636 Connie AVE, San Mateo

Listed by SALA Homes Group, 650-218-2178 from SALA Homes Realty & Development
(If provided) CoList: Carrie Zhang from SALA Homes Realty & Development

Sold listing courtesy of Linda Trinidad from APR

2295 Allegheny WAY, San Mateo
$3,600,000
4 Beds ⋅ 3 Baths ⋅ ML81979410 MLS
Eichler Remastered. Opportunity to own a one owner, 1957 Eichler, completely remodeled in the most desirable Eichler neighborhood, The Highlands. As you enter, you are greeted by an abundance of natural light streaming through the floor-to-ceiling windows, creating a bright and airy living space. The open floor plan effortlessly connects the living room, dining area, and kitchen, ideal for both relaxing and entertaining. The kitchen features fully custom cabinetry, while maintaining Eichler style, high-end appliances, including Gugganaue refrigerator and freezer and Meile 48" range-oven with built-in microwave and espresso maker and a large center island - a chef's dream. From the kitchen, step outside to the private backyard oasis, where you can enjoy peaceful evenings overlooking the lush landscape. The primary suite is a retreat in itself, with a beautiful en-suite bathroom and direct access to the backyard. There is an additional room off the main master designed to be a home office, nursery of gym. The additional bedrooms are spacious and filled with natural light. This home provides a tranquil escape while still being close to shopping, dining, parks, and excellent schools. Don't miss the opportunity to call this exceptional Eichler home, remastered.

2295 Allegheny WAY, San Mateo

Listed by Vladimir Rivkin, 650-504-1231 from Rothschild & RUK Real Estate, Inc.
(If provided) CoList: from

Sold listing courtesy of Chris A. Sabido from EXPCA

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San Mateo Eichler Style Real Estate & Homes