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$3,599,992
4 Beds ⋅ 3 Baths ⋅ ML82050779 MLS
An Eichler that lives as well as it looks. Set on a quiet cul-de-sac with sweeping valley views, Roxbury House preserves the light, openness, and indoor-outdoor connection that define Eichler living while offering the space, comfort, and functionality modern life demands. At the heart of the home, a generous kitchen, dining, and family room open directly to the beautifully landscaped backyard, creating an effortless connection between indoor and outdoor living. Walls of glass frame the surrounding landscape and fill the home with natural light throughout the day, while slender side-lite windows sneak leafy vignettes into the living spaces, creating moments of delight at every turn. With 4 bedrooms, 3 bathrooms, a separate laundry room, an art studio adjacent to the two-car garage, dual-pane windows, an updated roof, and a rare flat backyard with dedicated play areas, Roxbury House offers something increasingly difficult to find: an Eichler designed not just to admire, but to enjoy every day.

40 Roxbury LN, San Mateo

Listed by William Cheung, 650-759-8779 from Compass
(If provided) CoList: Laura Lee from Compass

Sold listing courtesy of Joel Stieber from KWLGE
$3,250,000
4 Beds ⋅ 2 Baths ⋅ ML82055667 MLS
Architectural elegance meets modern luxury in this masterfully reimagined Eichler-inspired residence in the coveted San Mateo Highlands. Thoughtfully renovated from top to bottom, this 4-bedroom, 2-bath home offers 1,764 sq. ft.living space on a private, flat lot surrounded by mature trees. Walls of glass, soaring beam ceilings, and all-new windows create a seamless indoor-outdoor connection filled with natural light.The chef's kitchen showcases custom cabinetry, premium Thermador appliances, exquisite Taj Mahal quartzite countertops with custom fabrication, designer under-cabinet and island lighting.Engineered hardwood floors flow throughout the open-concept living and dining areas, highlighted by a dramatic fireplace wall and views of the beautifully landscaped grounds.Spa-inspired bathrooms feature custom floating vanities with matching Taj Mahal quartzite, Toto washlet toilets, and designer finishes. Newly completed hardscape and landscape, a private front courtyard atrium with fountain, serene backyard water feature, new horizontal fencing, and multiple entertaining spaces.Additional highlights include a finished two-car garage with epoxy flooring and exceptional attention to detail throughout. Ideally located near parks, hiking trails, shopping, and major commuter routes.

1739 Lexington AVE, San Mateo

Listed by Soofie Jadallah, 650-785-3096 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Kathy Tai from GGP2V
$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
$3,150,000
4 Beds ⋅ 2 Baths ⋅ ML82057692 MLS
An expanded Eichler that's as livable as it is beautiful. Set on a quiet cul-de-sac, this 4+ bedroom home sits on an oversized 10,880 sq. ft. lot, blending iconic mid-century design with thoughtful modern engineering. Beyond the private front courtyard, vaulted ceilings and signature walls of glass provide brilliant natural light to the living spaces, framing private garden views. Four bedrooms, 2 bathrooms, a sunroom, a flexible bonus room, a separate laundry room and outdoor storage deliver the space, comfort and functionality needed for modern life (county records show 2140sf, floor plans show 2400sf). Step out to a backyard designed for seamless indoor-outdoor living, complete with a dining areas, a hot tub and mature landscaping. A free-standing studio adds flexible space for a home office, gym, or creative workshop. Engineered for reliable, year-round comfort, this all-electric home features owned solar, a Tesla Powerwall, Level 2 EV charging, dual-pane windows and mini-split heat pumps. Located near the Highlands Rec Center, Sawyer Camp Trail, and top schools, this property offers a combination rarely available: classic Eichler soul, an expansive lot and self-sufficiency for true peace of mind.

40 Powhatan PL, San Mateo

Listed by The Dwyer Group, 650-931-2036 from Compass
(If provided) CoList: from

Sold listing courtesy of Sue Crawford from CBR
$3,150,000
4 Beds ⋅ 2 Baths ⋅ ML82057464 MLS
Joseph Eichler w/ amazing unobstructed Santa Cruz Mountain views in the heart of the Highlands neighborhood! Beautiful mid-century modern w/ original period details including a light & bright open floor plan w/ exposed beams, high ceilings, wood panel siding, & globe pendant lighting. A spacious living room area welcomes you, seamlessly combining into a dining room/family room area along with a chefs eat-in kitchen w/ a large custom island w/ breakfast bar, custom cabinets, & stainless steel appliances. Ready to move-in with quality updates including double pane windows, custom Hunter Douglas automatic shades, radiant heating, updated bathrooms w/ imported tiles, copper plumbing, LVP flooring, & even an electric car charger. While a custom Garapa front fence welcomes you, the backyard is an entertainers delight w/ manicured hardscaping & landscaping, a glass rear fence, & your very own heated pool w/ hot tub & high end imported automatic pool cover. Conveniently located within Crystal Springs Shopping Center, Highway 280, Sawyer Trail, & a desirable school district. Such a proper & gorgeous home.

2052 Lexington AVE, San Mateo

Listed by Chris A. Sabido, 650-922-8888 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Lisa Oh from CBR
$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
$3,000,000
4 Beds ⋅ 3 Baths ⋅ ML82047272 MLS ⋅ Highlands Recreation BLDG.
Rarely for sale...10 LAUREL HILL COURT is an excellent example of mid-century architecture. Complete interior renovation and expansion (2020 with permits)this property offers filtered views of Crystal Springs reservoir, canyon and the bay! A "Unicorn in the Community representing only 1% of mid-century architecture community (over 700 mid century homes in Highlands Neigh)." This home is unique with a lower level that offers a 2-car garage and bonus space ideal for a home gym, office, creative space, or storage. The light-filled open space offers a sleek remodeled custom kitchen, with island, soaring beamed ceilings and quality finishes that include floor-to ceiling Milgard windows and hardwood-style vinyl floors. The living room has a brick, electric fireplace and access to a large balcony w/filtered views. An inviting side deck and yard that wraps around the home completes the indoor/outdoor dynamic. Highlands Recreation Center featuring a pool, tennis courts, playground, daycare, and after-school programs. Convenient access to Highways 280 and 92 offers an easy commute to both San Francisco and Silicon Valley. This is a show-piece, and you don't want to miss it.

10 Laurel Hill CT, San Mateo

Listed by Carmen Miranda, 650-743-4320 from Compass
(If provided) CoList: Mayya Brusilovskaya from Compass

Sold listing courtesy of Gary (gang) Liu from CBR
$3,000,000
4 Beds ⋅ 3 Baths ⋅ ML82040752 MLS ⋅ SM Highlands BLDG.
This gorgeous custom built SM Highlands home offers privacy & Zen like experiences w/ a babbling creek in the rear yard. Located next to protected county land. 4BD/2BA upstairs. Large office could be 5th BD and full BA downstairs. Family room, 2 gas/wood burning fireplaces, formal dining, Gourmet kitchen, Radiant heat, central vacuum, integrated sound system, custom lighting. Much more! Don't miss out! Rec center includes community pool, tennis courts, & after school programs. Sawyer Camp road close by for walking, jogging, & bike trails along the Crystal Springs reservoir. Great school district. Location! Location! Location!

2060 Bunker Hill DR, San Mateo

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

Sold listing courtesy of Daniel Smith from APR
$2,750,000
6 Beds ⋅ 3 Baths ⋅ ML82046672 MLS
Rare opportunity to own a fully permitted, expanded San Mateo Highlands home on the market for the first time in over 60 years. This expansive 2,460 sq ft 6BR/3BA home sits on a 9,800 sq ft lot and backs to the canyon, offering the privacy and serenity that makes this neighborhood so coveted. Soaring 10-foot tongue-and-groove ceilings and walls of glass in the main living areas, clean lines, and indoor-outdoor flow define the legacy here, while a thoughtfully expanded footprint gives multigenerational families genuine room to breathe. A newer roof and sewer line (both replaced in 2021) anchor a home that is otherwise primed for a full, thoughtful renovation. The home is ready for a family with vision someone who recognizes that the bones, the setting, the location, and the history cannot be replicated, and that the opportunity to put their own mark on a true mid-century original rarely comes twice. Moments from the community Recreation Center, Highlands School, and convenient access to Highways 280, 92, and 101.

1879 Lexington AVE, San Mateo

Listed by Pamela Merkadeau, 650-280-9046 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Joe Day from COMPS
$2,750,000
3 Beds ⋅ 2 Baths ⋅ ML82044883 MLS
Iconic Mid Century Home with vaulted ceilings, walls of glass, and a backyard peering out to open space. The walls of glass flood the home with natural light, creating a serene indoor-outdoor living experience. This highly desirable floor plan features 3 bedrooms and 2 bathrooms with additional bonus space that offers flexible options for work, fitness, or hobbies. The home is thoughtfully updated with mini-split heating and cooling for year-round comfort, double-pane windows, a newer foam roof, and solar power features for improved efficiency. Skylights and remote-controlled blinds enhance both light and livability. Outdoor living is effortless with a spacious patio overlooking a peaceful, private yard. Perfect for relaxing or entertaining. Ideally located within walking distance to the Highlands Recreation Center featuring a pool, tennis courts, playground, daycare, and after-school programs. Convenient access to Highways 280 and 92 offers an easy commute to both San Francisco and Silicon Valley.

2044 Lexington AVE, San Mateo

Listed by Mitch Wong, 650-483-8573 from Compass
(If provided) CoList: from

Sold listing courtesy of Bali Liu from CBR
$2,700,000
4 Beds ⋅ 2 Baths ⋅ ML82046976 MLS
Iconic Mid-Century Modern home in the highly sought-after San Mateo Highlands, thoughtfully remodeled to enhance its signature design. Walls of glass and skylights flood the home with natural light, creating a seamless indoor-outdoor living experience. The open-concept kitchen, dining, and living areas serve as the heart of the home, framed by floor-to-ceiling windows and new sliding glass doors that open effortlessly to the surrounding outdoor spaces. The spacious primary bedroom offers a peaceful retreat with a large walk-in closet, spa-inspired bath, and direct access to the backyard. Three additional bedrooms are generously sized and filled with natural light. Outdoor living is equally inviting, featuring a private interior courtyard ideal for al fresco dining and a spacious patio overlooking serene, tree-lined grounds designed for both relaxing and entertaining. Ideally located within walking distance to Highlands Elementary and close to the Highlands Recreation Center with pool, tennis courts, playground, daycare, and after-school programs. Convenient access to Highways 280 and 92 allows for an easy commute to both San Francisco and Silicon Valley.

2236 Bunker Hill DR, San Mateo

Listed by Hope Pilch, 650-619-4732 from HP Properties
(If provided) CoList: from

Sold listing courtesy of Mariana Pappalardo from COMPS
$2,620,000
4 Beds ⋅ 2 Baths ⋅ ML82041472 MLS
Gorgeous Eichler-style home in the highly sought-after Highlands community, showcasing the best of indoor-outdoor living with an open floor plan and abundant natural light. This 4-bedroom, 2-bath residence features an updated kitchen with a spacious island that flows seamlessly into the expansive living and dining areas, perfect for both everyday living and entertaining. Well-appointed bedrooms and updated bathrooms offer comfort and modern style. The spacious front yard provides privacy, while the beautifully landscaped backyard boasts a redwood deck, seasonal blooms, and a variety of fruit trees including orange, lemon, pear, apple, apricot, mulberry, and avocado. Located in a desirable neighborhood known for its strong community feel and scenic surroundings, this home is just minutes from shopping, hiking trails, and top-rated schools, with easy access to major freeways for a convenient commute.

1936 Ticonderoga DR, San Mateo

Listed by Angie Ni, 650-863-0879 from Coldwell Banker Realty
(If provided) CoList: Bali Liu from Coldwell Banker Realty

Sold listing courtesy of Jennifer Davis from SRNO04
$2,500,000
4 Beds ⋅ 2 Baths ⋅ ML82048838 MLS
Nestled in the coveted Highlands neighborhood, this cherished Eichler offers a rare opportunity to own a true piece of mid-century modern history. Lovingly enjoyed by the same family for decades & originally selected as one of the neighborhood's model homes, this home embodies the timeless appeal of Eichler design paired with the warmth of true community living. Ideally positioned on a flat lot, this open concept single-story residence is filled with natural light, skylights, & seamless indoor outdoor flow. The spacious kitchen features ample cabinetry, built in storage, stainless steel appliances including a gas range, eat up bar, & opens beautifully into the main living space. Custom built-ins & a media cabinet add both style & functionality. Walls of glass connect the indoors to a lush backyard opening to serene open space and a private front courtyard, creating the quintessential California lifestyle Eichler enthusiasts adore. The flexible floor plan offers 4 bedrooms plus a bonus room or walk-in closet off the primary suite. Enjoy the home's timeless character as is or personalize it over time. Moments from Crystal Springs Village, the Highlands Recreation Center, top commuter routes including 280, 92, and 101, and beloved neighborhood traditions.

2203 Allegheny WAY, San Mateo

Listed by Lana Morin, 650-207-5229 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Rayyan Fani from COMPS
$2,450,000
4 Beds ⋅ 2 Baths ⋅ ML82057712 MLS ⋅ Highlands BLDG.
Mid-century modern Highlands Eichler on a large Approx. 7,778 square foot landscaped lot with room for expansion or an ADU! Entertaining living room w/10-foot high soaring ceilings. Updated Sliding doors and dual pane windows. Nicely maintained original wood paneled walls. Four bedrooms Two baths, sitting room/office, plus additional space in garage ideal for game room. New carpets, new interior/exterior paint. Foam roof. Kids playroom in backyard. Outdoor covered patio for a relaxing shaded space. 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!

1708 Monticello RD, San Mateo

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

Sold listing courtesy of Joe Day from COMPS
$2,350,000
3 Beds ⋅ 2 Baths ⋅ ML82049103 MLS ⋅ SM Highlands BLDG.
recently updated in a desirable location! With approximately 1500 square feet of living space, plus an additional approx. 300 square foot bonus room. This house is perfect for those who value both comfort and convenience with a spacious feel of this Eichler home! The living room is cozy and inviting, with large windows that let in plenty of natural light. Wood burning fireplace for extra comfort. The kitchen is well-appointed, with a galley kitchen & plenty of counter space for meal preparation. The dining area is conveniently located adjacent to the kitchen, making it easy to entertain guests. The bonus/hobby room can easily double as a home office or utility room. The house is situated on a big Level lot providing a peaceful and serene environment. The backyard is spacious and perfect for expansion or an ADU. The property also features a two-car garage Rec center includes community pool, tennis courts, & after school programs. Sawyer Camp road close by for walking, jogging, & bike trails along the Crystal Springs reservoir. Great school district. Location! Location! Location!

1571 Forge RD, San Mateo

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

Sold listing courtesy of Soofie Jadallah from CBR
$1,275,000
2 Beds ⋅ 3 Baths ⋅ ML82048166 MLS
Tucked away in the desirable San Mateo Highlands, this private and serene townhome offers a thoughtful multi-level layout with stylish updates and inviting indoor-outdoor living. The updated kitchen anchors the expansive main living level, where soaring wood beam vaulted ceilings create a bright and airy atmosphere across the open-concept living and dining spaces. The living room flows seamlessly to a spacious deck, creating the perfect setting for entertaining or everyday relaxation. The lower level features a spacious primary ensuite with its own private outdoor patio, along with an additional bedroom, full bath, and dedicated laundry room. One of the homes standout features is the dramatic third-floor loft overlooking the main living area an ideal flex space for a home office, media room, creative studio, or guest retreat, filled with natural light and architectural character. Enjoy the convenience of a detached garage parking space plus an additional assigned spot. Community amenities include a swimming pool and tennis courts. Ideally located just minutes from Crystal Springs Village, Hillsdale Shopping Center, College of San Mateo, scenic parks and trails, top-rated schools, and easy access to Highways 92, 101, and 280.

2329 Ticonderoga DR, San Mateo

Listed by Nick Roe, 650-719-1881 from Real Brokerage Technologies
(If provided) CoList: from

Sold listing courtesy of David Cao from RBT
$1,080,000
2 Beds ⋅ 3 Baths ⋅ ML82051026 MLS ⋅ Ticonderoga Townhomes BLDG.
Completely rebuilt in 2022, this stunning Tahoe-inspired 2-story townhouse seamlessly blends luxury, sustainability, and AI smart home technology. Soaring arched vaulted ceilings with custom skylights and a retractable sun roof fill the home with natural light, while white oak wood floors and a warm gas fireplace with custom tile and mantle create an effortless elegance throughout. The brand-new granite kitchen features custom wood cabinetry, stainless steel appliances, a trash compactor, and a charming breakfast/office nook overlooking majestic Redwood Trees a chef's dream with an eco-conscious heart. Philips Hue smart lighting, whole-home surround sound, and smart lock entry technology complete the connected living experience. The primary ensuite offers a soaking tub, walk-in shower, dual custom closets, and direct patio access, while a second bedroom and smart Samsung laundry room round out the lower level. Two balconies showcase breathtaking canyon, pool, tennis court, pickleball and hot tub views. A 400 sq. ft. private patio is perfect for entertaining or relaxing. New vapor barrier and insulation dramatically reduce energy costs. Attached garage with whisper-quiet door, Parking Spot #1, and ample guest parking. HOA maintained. Walk to Crystal Springs Village.

2321 Ticonderoga DR, San Mateo

Listed by Mike Masoumi, 408-666-2112 from RE/MAX Santa Clara Valley
(If provided) CoList: from

Sold listing courtesy of Stanley Zhu from KINE
$1,049,000
2 Beds ⋅ 3 Baths ⋅ ML82046209 MLS ⋅ Ticonderoga Townhomes BLDG.
Huge price reduction! Extra large, remodeled 2bd/2.5bth townhome with two parking spaces in the highly sought-after Ticonderoga community, ideally located near Highlands Elementary, the College of San Mateo, and Highways 92 and 280. Renovated in 2018, this home features extensive upgrades, including a newer roof, oak hardwood floors, dual-pane windows, wood-paneled ceilings, fire sprinklers, an updated furnace and water heater, newer bedroom carpeting, fresh interior paint, and skylights that fill the home with natural light. The upper level offers an open-concept layout with soaring ceilings, creating a bright, loft-like feel that seamlessly connects the kitchen, dining, and living areas. The expansive living area provides plenty of room for large furnishings and includes a gas fireplace, an extra-wide wall ideal for a large TV or projection system, a half bathroom, and a private deck overlooking the trees and backyard - perfect for entertaining! The lower level includes two bedrooms, two full bathrooms, a laundry room, and direct backyard access from the master bedroom. There are two parking spaces - one enclosed garage space and one extra parking space. Community amenities include a pool, tennis court, and two pickleball courts.

2319 Ticonderoga DR, San Mateo

Listed by David Howarth, 415-867-9569 from Bay Capital Real Estate
(If provided) CoList: from

Sold listing courtesy of Kathy Chern from SNIG01

board logoThe 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 Intero 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.


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