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$1,888,000
3 Beds ⋅ 2 Baths ⋅ ML82048989 MLS
Thoughtfully rebuilt and expanded, this extensively updated residence blends modern design, everyday functionality, and an unbeatable Peninsula location. Vaulted ceilings, wide-plank hardwood floors, and an open-concept layout w/ natural light. The chef's kitchen was completely rebuilt in 2021 & showcases sleek custom cabinetry, a full suite of Thermador appliances and a dramatic waterfall quartz island that anchors the living & dining areas. The spacious primary suite features a spa-inspired bath w/ dual vanities and his-and-her walk-in closets. Generously sized secondary bedrooms are complemented by a window-lined pantry currently used as a home office, plus an additional office area created from a portion of the garage-side laundry space. Major improvements include a rebuild and expansion of the bedroom & living areas in 2019, followed by additional upgrades in 2021. Additional features include central A/C, heating, whole-house water filtration, tankless water heater, sprinkler system, & newer washer/dryer. The beautifully redesigned backyard features expansive paver patios & artificial turf, creating a low-maintenance setting. Walking distance to Whole Foods and Hillsdale Shopping Center, w/ quick access to Highway 101.

233 Poinsettia AVE, San Mateo

Listed by Wen Guo RE Group, 650.867.1128 from KW Advisors
(If provided) CoList: from

$1,620,000
2 Beds ⋅ 1 Baths ⋅ ML82053886 MLS
This welcoming home situated on an oversized corner lot offers approx. 1,000 square feet of living space, w/two bedrooms & one bath. The open floor plan creates a bright, airy atmosphere, enhanced by hardwd floors throughout. The living room fireplace provides a cozy ambiance. The chef's kitchen boasts a breakfast bar, perfect for casual dining. The remodeled bathroom showcases modern finishes. Abundant closet & storage space ensures ample organization throughout. Outside, you'll be enchanted by the spectacular landscaping, featuring a great variety of plants & fruit trees. Raised vegetable garden beds offer an opportunity to cultivate your own fresh produce. The covered deck, draped in grapevines, provides a delightful outdoor living & entertainment space. Meticulously maintained & upgraded the home boasts excellent overall condition, w/newer systems, dual pane windows, high-quality doors & hardware, & crown moldings. The designer color interior & luxury garage flooring add an element of refined sophistication. The SM Village, a great community of close knit neighbors, is located in the mid-peninsula area. It offers very easy access to SFO Airport, San Francisco, & Silicon Valley. An ideal choice for those seeking a superior, well-appointed & centrally situated property.

3801 Orinda DR, San Mateo

Listed by Frances Boscacci, 650-759-7885 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Caitlin Beanan from CBR
$1,899,000
4 Beds ⋅ 2 Baths ⋅ ML82052368 MLS
Oozing with the timeless charm and character of yesterday, this delightful 4bed/2bath home offers warmth, personality, and inviting living spaces throughout. The spacious living room features a gas fireplace and gleaming real hardwood floors, while the separate family room with a built-in bar is perfect for entertaining or relaxing. The eat-in kitchen offers a breakfast bar, stainless steel appliances, and a functional layout for everyday living. Private backyard with mature landscaping, ideal for relaxing or entertaining. Two utility sheds offer additional storage, and a private well provides a valuable resource for landscape irrigation. Ideally located in the heart of the Peninsula between San Francisco and Silicon Valley, this home is just minutes from Hillsdale Shopping Center, Caltrain, and Highways 101, 92, and 280, providing exceptional access to shopping, dining, parks, and major commute routes. A wonderful opportunity to own a home full of character in an unbeatable Peninsula location.

114 E Hillsdale BLVD, San Mateo

Listed by Allison M Fujimoto, 650-888-3863 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$1,550,000
3 Beds ⋅ 2 Baths ⋅ ML82052134 MLS
Classic comfort, flexible living, and everyday convenience come together in the heart of San Mateo Village. This inviting 3-bedroom, 2-bath home blends original character with thoughtful updates and abundant natural light. The living room sets the tone with Mid-Century hardwood floors, a cozy fireplace, oversized vinyl dual-pane windows, and plantation shutters. Skylights, solar tube, expansive windows, and sliding glass doors give the home a bright feel. Recent improvements include interior paint, upgraded interior doors, hinges, and hardware, plus electrical fixtures, a durable 2019 TPO/PVC roof. The remodeled hall bath features marble tile and tasteful finishes, the kitchen and family room combo offer everyday ease with tile flooring, a convection oven, gas cooktop, microwave oven, dishwasher, generous cabinet space, butlers station, pantry, and seamless patio access. A separate den with exterior access adds flexibility for an office, studio or guest space. The spacious primary suite opens to a private covered patio for morning coffee, relaxed evenings, and year-round outdoor enjoyment. Near Whole Foods, Trader Joes, Hillsdale Shopping Center, Caltrain, commute routes, and leading Peninsula employers, this San Mateo Village gem delivers lifestyle, location, and livability.

605 E 39th AVE, San Mateo

Listed by J.D. Anagnostou, 650-704-5134 from Realsmart Properties
(If provided) CoList: from

Sold listing courtesy of Maria Baker from APR
$2,737,000
3 Beds ⋅ 2 Baths ⋅ ML82051525 MLS
Located in desirable San Mateo Village, this exceptional home has been thoughtfully expanded and extensively renovated to showcase modern design and luxury living. The open-concept floor plan is centered around a striking contemporary fireplace and seamlessly connects the living room, dining area, kitchen, and family room, filled with abundant natural light. The living room features a premium 5.2.2 Dolby Atmos surround sound system, ideal for entertaining and everyday enjoyment. The beautifully appointed kitchen offers custom cabinetry, designer finishes, a pot filler, built-in microwave, and a spacious island with additional storage. The primary suite features a tray ceiling, walk-in closet with built-ins, and a spa-inspired bath with Hansgrohe fixtures, custom vanities, and built-in cabinetry. Smart home upgrades include app and voice-controlled lighting, Ubiquiti security cameras, in wall/ceiling Wi-Fi access points, and a G4 doorbell integrated within the UniFi ecosystem. A detached shed provides flexible space for a home office, gym, or studio. The landscaped backyard features artificial turf and a pebble-rock play area, while the front yard offers natural grass. Conveniently located near Bay Meadows, restaurants, Hillsdale Shopping Center, Caltrain, and Highway 101.

174 Mclellan AVE, San Mateo

Listed by Mike Danao, 650-274-8890 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of James Steele from COMPS
$1,620,000
2 Beds ⋅ 2 Baths ⋅ ML82048052 MLS
This home has it all! Excellent natural light. Superb school district. A must see for those seeking the best in value, condition and location. This ranch style home is located on a highly desired street in one of San Mateo's most sought-after neighborhoods, San Mateo Village. Enter under the welcoming covered front porch to the spacious living room with large front picture window. The home enjoys a large family room - perfect for entertaining! The remodeled kitchen has new cabinetry topped in marble-style counters and new stainless-steel appliances include range and dishwasher. Both baths have been completely updated. The large family room opens up to a big backyard. There are entertainment possibilities galore!! This home sits on a quiet, highly desirable street less than one mile from Whole Foods, restaurants, Hillsdale Shopping Center, located blocks from George Hall Elementary School, with close proximity to Caltrain, Casanova Park and the Bay Meadows development. It has convenient access to Highways 101, 92, & 280. Run, Dont Walk to this home. You won't want to Miss It!

3908 Regan DR, San Mateo

Listed by Jill Ballard GRI, 408-828-6759 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Helen Li from RDFIN
$1,675,000
3 Beds ⋅ 2 Baths ⋅ ML82045820 MLS
COMFORT, FLEXIBILITY & CHARM IN DESIRABLE SAN MATEO VILLAGE! The beautiful home offers a wonderful blend of comfort, functionality, and flexible living space. The spacious living room features a cozy gas fireplace, crown molding, and hardwood flooring. Updated kitchen with quartz countertops, ample cabinetry, and adjacent dining area with built-in shelving and storage. Main level includes three generous bedrooms and updated bathroom with full-size step-in shower, quartz vanity, recessed cabinetry, and two spacious hall closets. Hardwood flooring continues throughout the main living areas and bedrooms, creating a cohesive and timeless feel. Finished attic offers exceptional versatility with loft-style bedroom or office/den, closet, a full bathroom with stall shower, quartz-top vanity, and storage cabinet, plus an expansive bonus room ideal for media room, playroom, office, guest retreat, or creative space. Private backyard features mature trees, colorful foliage, lush lawn, and patio area perfect for outdoor dining, entertaining, or quiet relaxation. Conveniently located near parks, shopping, dining, excellent schools, Caltrain, and major commuter routes. Wonderful opportunity to put down roots and begin your next chapter!

3726 Casanova DR, San Mateo

Listed by Kelly Hunt, 408-506-0709 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of The Sharp Group from KWPEN
$1,588,000
3 Beds ⋅ 1 Baths ⋅ ML82046089 MLS
This 3-bedroom, 1-bath home is located in San Mateo on a lot of approximately 5,000 square feet. The 1,080 square-foot interior features hardwood and vinyl/linoleum flooring throughout. The kitchen includes granite countertops and a gas range, and is adjacent to a formal dining room. The living room has a fireplace, and heating is provided by central forced air. Laundry facilities are conveniently located in the garage, which offers one parking space. The bathroom includes a shower over the tub. The home is part of the San Mateo-Foster City Elementary school district.

3705 Pasadena DR, San Mateo

Listed by Kent Flinn, 650-534-7749 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Peter Thai from APR
$1,710,000
3 Beds ⋅ 1 Baths ⋅ ML82046723 MLS
Set on a picturesque residential street, this beautifully reimagined home blends classic charm with modern sophistication. Storybook-inspired architecture, a crisp designer palette, and refreshed curb appeal create an inviting first impression, enhanced by drought-conscious landscaping and a welcoming stone pathway. Inside, the expansive living room features a striking stacked-stone fireplace with gas insert, recessed lighting, and built-in surround sound system. The light-filled dining area flows seamlessly into the remodeled kitchen, showcasing shaker cabinetry, quartz countertops, porcelain tile backsplash, and stainless steel appliances. 3 spacious bedrooms offer abundant light and storage, while the updated bath includes a granite surround, quartz vanity, and LED smart mirror. A versatile bonus space is accessed through the attached 1-car garage. The serene backyard is ideal for entertaining with a covered paver patio, outdoor TV, tiki bar, lawn, citrus trees, and storage shed. Conveniently located near shopping, dining, fitness, medical services, Hillsdale Shopping Center, Caltrain, and Highways 101 & 92. Too many updates to list! Some photos have been digitally altered.

3533 Pasadena DR, San Mateo

Listed by Cynthia Smith, 650-743-6865 from Compass
(If provided) CoList: from

Sold listing courtesy of Christopher Eckert from KWPEN
$1,575,000
2 Beds ⋅ 1 Baths ⋅ ML82042170 MLS
Situated on a desirable street in the heart of San Mateo Village, this beautifully updated single-level home blends timeless charm with thoughtful modern upgrades. A picture-perfect front porch and refreshed landscaping create an inviting first impression. Inside, luminous hardwood floors and a soft neutral palette set a warm, cohesive tone, while natural light fills the space through large windows and plantation shutters. The living area is anchored by a classic fireplace, offering both comfort and style. The remodeled kitchen features stone countertops, quality cabinetry, stainless steel appliances, and a breakfast bar that flows seamlessly into the dining area with direct backyard accessideal for everyday living and effortless entertaining. Bedrooms are well-proportioned and versatile, while the updated bathroom and refined finishes throughout reflect pride of ownership. Additional features include dual-pane windows, crown molding, and a newer roof. Step outside to an expansive backyard with mature trees, multiple seating areas, and space to relax or gather. Conveniently located near parks, shopping, dining, and major commute routes.

3920 Regan DR, San Mateo

Listed by Wen Guo RE Group, 650.867.1128 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Alice Xu from ZL2TR
$2,200,000
4 Beds ⋅ 2 Baths ⋅ ML82043440 MLS
Where form, function, scale, and light seamlessly coexist, this completely renovated and expanded 4BR/2BA showpiece in San Mateo Village offers a transformative living experience. Elegantly composed and spanning approximately 1,536 SF, the refined floor plan is elevated by wide plank flooring, crown moldings, premium millwork, contemporary fixtures, and a designer color palette. The spacious living room flows effortlessly into the dining area and ideally positioned kitchen, beautifully appointed with quartz countertops, shaker cabinetry, a gas range, and stainless-steel appliances. Privately situated, the magnificent primary suite is distinguished by a soaring cathedral open-beam ceiling, direct access to the rear deck, a walk-in closet, and a sumptuous bath featuring a skylight, dual vanities, and an impressive, oversized shower. Three additional bedrooms, a full bath, a laundry room, and an attached one-car garage complete the interior. Outside, an inviting lounging terrace transitions seamlessly to a pergola-covered dining pavilion with integrated heaters, a built-in barbecue, and an artisan pizza oven, creating an exceptional setting for year-round outdoor enjoyment. A sizable lawn, expansive paved side yard, and storage shed further enhance the thoughtfully designed grounds.

409 Poinsettia AVE, San Mateo

Listed by Nicholas Delis, 650-515-6394 from Compass
(If provided) CoList: from

Sold listing courtesy of Val Vandervort from VERIT
$2,300,000
3 Beds ⋅ 2 Baths ⋅ ML82043299 MLS
A beautiful move-in ready home in a warm and friendly neighborhood, offering comfort, convenience, and future potential. It features 1,400 sq ft of living space on an oversized 7,370 sq ft corner lot. The inviting living room features large windows and a wood-burning fireplace, while the adjacent dining area opens to a spacious backyard. The brand-new kitchen is filled with abundant natural light, creating a bright and enjoyable space for everyday cooking. The primary bedroom faces the backyard for added privacy, while two additional well-appointed bedrooms share a full bath. A flexible room next to the kitchen provides the perfect space for a home office or guest room. The expansive front and back yards, enhanced with new landscaping and mature fruit trees, are ideal for gardening or creating a private outdoor retreat. The generous lot also offers excellent potential for an ADU or future expansion (buyer to verify). A two-car garage adds convenience and ample storage. Ideally located within close proximity to George Hall Elementary School, Casanova and Laurie Meadows Parks, the Caltrain station, Hillsdale Shopping Center, and Bay Meadows, with convenient access to Highways 101, 92, and 280, this home offers an ideal central Peninsula location. Welcome to your beautiful home!

245 E 40th AVE, San Mateo

Listed by Sherry Cao, 415-261-8004 from BQ Realty
(If provided) CoList: April Zhao from BQ Realty

Sold listing courtesy of Hebe Li from AGNC
$2,050,000
3 Beds ⋅ 2 Baths ⋅ ML82042428 MLS
First time on the market in over 65 years! Welcome to this cherished 3-bedroom, 2-bathroom family home located in the highly desirable San Mateo Village neighborhood. Brimming with pride of ownership, this home features beautiful hardwood floors, elegant crown molding, dual-pane windows, central heating, leased solar panels, in-home laundry, and a two-car garage. The well-appointed kitchen offers stainless steel appliances, a gas stove, and natural stone countertops, seamlessly flowing into a spacious family room. From there, step out onto the expansive deck and enjoy the private backyard...Perfect for entertaining or relaxing with family and friends. Ideally situated, this home provides close proximity to Caltrain, Hillsdale Shopping Center, Whole Foods, and the vibrant Bay Meadows development and commuters will appreciate easy access to Highways 101, 92, and 280.

3713 Santiago ST, San Mateo

Listed by Dennis Murphy, 415-310-7956 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Sameen Babar from SZIR01
$1,700,000
3 Beds ⋅ 1 Baths ⋅ ML82041279 MLS
A charming and beautifully updated ranch style single family home in the heart of San Mateo. The 3-bedroom, 1-bathroom layout is thoughtfully designed, with natural flow between living spaces. New flooring throughout. Bright living room has fireplace, large windows. The well-appointed kitchen boasts modern appliances, stylish cabinetry, and ample counter space, making it a joy for both aspiring chefs and seasoned cooks alike. Large backyard with covered lounge area, ideal for outdoor dining, quiet mornings and evening relaxation. This house is close to shops, parks, schools and major commuting routes. Welcome home!

505 Santa Clara WAY, San Mateo

Listed by Ziwei Wang, 408-771-9191 from Coldwell Banker Realty
(If provided) CoList: Dan Li from Coldwell Banker Realty

Sold listing courtesy of Long Chen from KWCU
$2,560,000
3 Beds ⋅ 2 Baths ⋅ ML82039472 MLS
Beautifully updated 3-bedroom, 2-bathroom home with open-concept living in the desirable San Mateo Village neighborhood. The floor plan flows seamlessly from the welcoming living room with fireplace and plantation shutters to the dining and family areas. The chef-inspired kitchen features quartzite counters with breakfast bar, stainless steel appliances, and ample cabinetry. Vaulted ceilings with exposed beams, recessed lighting, and large French doors enhance indoor-outdoor flow to the private backyard with lawn, multiple patios, paver and wood decking, mature landscaping, string lighting, and flip-out window. The primary suite includes vaulted ceilings, French doors, and a walk-in closet with built-ins, while two additional bedrooms feature wood-plank tile floors and quality fixtures, with a marble vanity in the primary bath and a quartz vanity in the hall bath. and wood-plank tile floors complete the home. Attached garage with updated 220-volt 50-amp charging outlet, built-ins, workspace, laundry, and storage. Walking/biking distance to Casanova Park, Bay Meadows shops and restaurants, Whole Foods, top San Mateo schools, Caltrain, and Highway 101.

3944 Regan DR, San Mateo

Listed by Raziel A. Ungar, 650-720-5483 from Compass
(If provided) CoList: from

Sold listing courtesy of Gillian Kilroy from APR
$1,418,888
2 Beds ⋅ 1 Baths ⋅ ML82039185 MLS
This single-story home in the desirable San Mateo Village offers immense potential, featuring two generous bedrooms, a full bath, hardwood flooring, and a kitchen equipped with granite countertops and wood cabinetry. Situated on a 5,000 sq. ft. lot, the expansive backyard provides endless possibilities for outdoor living, gardening, or future expansion. This is an ideal starter home in a neighborhood where renovations represent a significant value-added opportunity. The property also includes two storage sheds for additional convenience. The location offers exceptional appeal with close proximity to George Hall Elementary, the Hillsdale Shopping Center, and Caltrain. Playgrounds and a dog park at Laurie Meadows and Casanova Parks are just down the road. The home provides easy access to San Francisco and Silicon Valley via Highways 101, 92, and 280.

3726 Martin DR, San Mateo

Listed by Kueilan Lee, 650-430-1826 from K Lee California Realty
(If provided) CoList: from

Sold listing courtesy of Tiffany Nga Nguyen from RDFIN
$2,050,000
3 Beds ⋅ 2 Baths ⋅ ML82038494 MLS
San Mateo Village living at its best! Modern refinement, quality upgrades, and pride of ownership are evident throughout this beautifully maintained 3-bedroom, 2-bathroom home. Features include luxury vinyl flooring, crown molding, dual-pane windows & central heating. The well-appointed kitchen boasts stainless steel appliances, granite countertops & an Italian-tiled floor & opens to the adjoining dining room highlighted by a skylight that fills the space with natural light. Both bathrooms have been tastefully updated and feature Toto toilets and blue-light ventilation fans. The hallway bathroom includes a jetted tub and Brazilian tiled floor, while the primary bathroom offers a step-in shower, lighted mirror, and skylight. Enjoy the spacious family room with a sliding patio door that opens to a fabulous private backyard....perfect for relaxing or entertaining. The outdoor space features a Calstone paver patio, numerous fruit trees, drought-resistant landscaping, and decorative Salmon Bay pebbles. Ideally located near Casanova Park & just blocks from George Hall Elementary School. Conveniently located near the Hillsdale Shopping Center, Whole Foods Market & the vibrant Bay Meadows development. Commuters will appreciate easy access to Caltrain & nearby Highways 101, 92, and 280.

3817 Martin DR, San Mateo

Listed by Dennis Murphy, 415-310-7956 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Christine Rosenfeld from APR
$2,350,000
3 Beds ⋅ 2 Baths ⋅ ML82038492 MLS
Move right in and start enjoying life in the San Mateo Village. This beautifully updated 3-bedroom, 2-bath home blends comfort, charm, and an unbeatable neighborhood setting known for its strong sense of community and highly regarded George Hall Elementary. Inside, refinished oak floors, vaulted ceilings with skylights, modern lighting, dual-paned windows, and fresh interior and exterior paint create a bright, polished feel throughout. The living room with fireplace flows into a dining area with French doors opening to the patio and gardens, while the granite-finished kitchen features a dining island and stainless steel appliances. The spacious primary suite offers lofty ceilings, a cozy window alcove, walk-in closet, and bath with elevated soaking tub. Two additional bedrooms sit along a private hallway for comfortable living. Outside, stone pathways wind through colorful botanicals, fruit trees, and dry creek beds, creating a peaceful garden retreat. A charming stand-alone cottage adds flexible space for hobbies, work, or relaxation. Perfectly located in one of the Peninsulas most beloved neighborhoods, with easy access to parks, shopping, and major commute routes, you don't want to miss this turn-key gem.

3612 Santiago ST, San Mateo

Listed by Maria Baker, 415-412-2590 from Compass
(If provided) CoList: Julie Baumann from Compass

Sold listing courtesy of Hira Bakhsh from SZIR01
$2,585,000
4 Beds ⋅ 3 Baths ⋅ ML82037503 MLS
Turn-key Modern Masterpiece in highly desirable San Mateo Village! Previously taken down to the studs and expanded, this single-story stunner features a brilliant open floor plan, vaulted ceilings, and an abundance of natural light. The chefs kitchen is equipped with high-end Bertazzoni appliances, beautiful quartz countertops, and custom cabinetry, flowing seamlessly across gorgeous engineered hardwood floors. You can buy with absolute confidence knowing this home was comprehensively upgraded during its massive remodel, featuring modernized electrical and plumbing, a premium tankless water heater, dual-pane windows, updated roof and insulation, plus Central Heating & A/C. Perfectly situated just steps from Casanova and Lauriedale Parks, you are minutes away from top dining, shopping, and major commute routes. Come experience the incredible neighborhood friendliness and community spirit that The Village is famous formove right in and welcome home!

3992 Casanova DR, San Mateo

Listed by Lina Pan, 669-666-4384 from SALA Homes Realty & Development
(If provided) CoList: from

Sold listing courtesy of Sameen Babar from SZIR01
$2,250,000
3 Beds ⋅ 2 Baths ⋅ ML82035526 MLS
Welcome to 3957 Martin Dr, a bright and inviting residence offering comfort, functionality, and an ideal Peninsula location. Boasting a total of 1,635 sq.ft. (1,450 sq.ft. main living area plus an additional 185 sq.ft. sunroom). Thoughtfully updated and beautifully maintained, this home features a well-designed floor plan filled with abundant natural light, spacious living areas, and seamless indoor-outdoor flow. The living room showcases large windows and a warm, welcoming ambiance, while the kitchen offers ample cabinetry and generous workspace for effortless meal preparation. Bedrooms are well-proportioned and comfortable. Luxurious bathrooms featuring Porcelanosa floating vanities, tiles, and skylights that fills the space with beautiful natural light. Additional living space awaits in the stunning sunroom, offering panoramic views of the lush backyard. Step outside to your private backyard oasis with a manicured lawn and tranquil patio -- perfect for alfresco dining and weekend gatherings. Owned solar panels and Tesla EV wall connector. This beautiful home invites you to settle in and enjoy nearby parks, restaurants, shopping, all amenities and easy access to freeway, high tech companies, and the best recreation and entertainment venues in the area! Enjoy your new home!

3957 Martin DR, San Mateo

Listed by Heidi Tang, 510-316-4797 from Valley Vine Realty
(If provided) CoList: Yu-En Tsai from Valley Vine Realty

Sold listing courtesy of Vivian Lee from HMNRE
$2,401,888
4 Beds ⋅ 3 Baths ⋅ ML82033884 MLS
Your dream home awaits in San Mateo! This spacious 4 BED / 3 BATH home offers ~2,020 sq ft of well-planned living on a quiet, highly desirable street. The home's heart is the Family Great Room that flows to the Kitchen as well as the serene outdoors. A large open stadium kitchen with stainless steel appliances, granite countertops and breakfast bar opens to the dining area and family great room, which flow out to a fabulous landscaped backyard with 2 patio areas, perfect for everyday living and easy alfresco entertaining. The flexible floor plan includes two primary suites, (one on each level) perfect for multigenerational living plus there are 2 additional bedrooms & a generous formal living room with a fireplace. This home has abundant space to live, work, and play! Located blocks from George Hall Elementary with easy access to Caltrain, Hillsdale Shopping Center, Whole Foods, Bay Meadows, Downtown San Mateo Dining, Parks, and Conveniences. Quick commuting via Highways 101, 92, & 280 makes this an ideal central Peninsula location. Welcome home to 3936 Regan Drive!

3936 Regan DR, San Mateo

Listed by Yelena Lepina, 650-288-2815 from Luxuriant Realty
(If provided) CoList: from

Sold listing courtesy of Jennie Lok from KWPEN
$1,755,000
5 Beds ⋅ ML82033640 MLS
Welcome to 53-55 E 39th Street, a rare and spacious duplex located in the heart of San Mateo. This versatile property offers an incredible opportunity for investors, multi-generational living, or owner-occupants seeking additional rental income. The front unit features 3 bedrooms and 1 bathroom with a generous layout ideal for a family or primary residence, while the rear unit offers 2 bedrooms and 1 bathroom, perfect for a small family. Each unit enjoys its own private entrance, garage, indoor laundry, and access to outdoor yard space. Interiors are bright and well-maintained, with hardwood flooring and updated kitchens throughout. Not to mention each unit has its own oversized back yard, bringing in additional cashflow for investors. Located on a quiet, tree-lined street just minutes from Hillsdale Shopping Center, Caltrain, top-rated schools, and an array of dining and retail options, this property offers a perfect blend of comfort, convenience, and long-term value. Easy access to Highways 92, 101, and El Camino Real makes commuting a breeze. Whether you're looking to live in one unit and rent the other, or add a high-quality asset to your real estate portfolio, 53 E 39th Street presents a rare and rewarding opportunity in one of the Peninsulas most desirable locations.

53 E 39th AVE, San Mateo

Listed by Dominic Gluhaich, 408-710-4538 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Vygandas Razhas from CCREEB
$1,500,000
3 Beds ⋅ 2 Baths ⋅ ML82033443 MLS
Welcome to 98 E. Hillsdale Blvd! This beloved long-time family home offers a unique opportunity in a highly convenient Peninsula location. Featuring 3 bedrooms and 2 bathrooms on a spacious 6,000+ sq. ft. lot, the property presents strong potential for an owner-user to customize or an investor to reimagine and add value. Ideally positioned near shopping, dining, major commute routes, and everyday amenities, this is an excellent chance to secure a foothold in a well-established San Mateo neighborhood.

98 E Hillsdale BLVD, San Mateo

Listed by Jalayne Forrester, 408-799-5175 from KW Bay Area Estates
(If provided) CoList: from

Sold listing courtesy of Namrata Anandikar from KWLGE
$2,268,000
4 Beds ⋅ 2 Baths ⋅ ML82032976 MLS
Mid-century modern home with contemporary updates, move-in ready and turnkey. Light-filled 4BR/2BA open floor plan featuring floor-to-ceiling windows in living, dining, and primary bedroom, plus skylights in kitchen and baths. Chefs kitchen offers oversized island with induction cooktop, high-powered hood, built-in panel wall with dual ovens plus steam oven, Bluetooth coffee maker, and generous cabinetry. Spacious primary suite includes walk-in closet and private patio access. Extensive custom storage throughout, including built-ins and upgraded shelving for easy organization. Spa-style bathrooms with dual sinks, curbless showers, and rainfall heads. Major upgrades include new roof (2020, 30-yr warranty), tankless water heater (2021), stainless steel gutter guards, remodeled garage with Polycuramine flooring, custom storage, lighting, and work area. Smart home features include Ring doorbell, Nest thermostat and outdoor cam, and Philips Hue smart lighting. Private backyard with modern floating deck, smart irrigation system, retractable hose reel, tall fencing, and creek backdrop. Convenient location near Hillsdale Shopping Center, Whole Foods, Trader Joes, Caltrain, Hwy 101/92, and top-rated schools. Fiber internet available.

78 Poinsettia AVE, San Mateo

Listed by Daniel Xi, 408-623-0766 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Nick Villanueva from KINE
$1,317,000
3 Beds ⋅ 1 Baths ⋅ BE41122406 MLS
Located in a desirable San Mateo neighborhood, 4105 Branson Dr offers a functional layout with generous living spaces and abundant natural light. The home provides a solid foundation and presents an excellent opportunity for buyers looking to update and customize to their own taste. Set on a quiet residential street, the property is conveniently close to parks, shopping, dining, and major commute routes. A great option for owner-occupants or investors seeking long-term potential in a well-established community.

4105 Branson Dr, San Mateo

Listed by Jeff Goodman, (510) 407-0905 from Compass
(If provided) CoList: Heather Duke from Compass

Sold listing courtesy of Alexander Lehr from SFBR
$1,899,000
ML82032146 MLS
19 E 41st Place is a well-maintained six-unit multifamily asset in the desirable San Mateo submarket. Built in 1957 and significantly renovated in 2014, the 2,447 SF building on a 7,699 SF lot features upgraded interiors, improved building systems, dual-pane windows, and refreshed exterior finishes. The property offers six spacious studio units, including one with a private yard and one with a private patio. Operational efficiency is a key advantage, with tenants paying all utilities through RUBS, minimizing operating expenses. Additional upside includes an owner-owned on-site laundry machine and six dedicated carport parking spaces, a strong amenity in this Peninsula location.

19 E 41st PL, San Mateo

Listed by Theodore Wong, 650-228-9930 from Compass
(If provided) CoList: Aparna Sayana from Compass
$1,140,000
2 Beds ⋅ 1 Baths ⋅ ML82027285 MLS
Off Market Sale - Comp Purposes only

208 San Miguel AVE, San Mateo

Listed by Olivia Mcnally, 650-576-6666 from Real Brokerage Technologies
(If provided) CoList: from

Sold listing courtesy of Olivia Mcnally from RBT
$1,350,000
2 Beds ⋅ 1 Baths ⋅ ML82025121 MLS
First time on the market in 40 years!! This well-cared for two-bedroom, one-bathroom charmer sits on a large 6,392 sq. ft. lot with a ton of potential! This home boasts hardwood flooring, dual pane windows, central heating, and an updated bathroom. The updated kitchen features stainless steel appliances, gas stove, and granite countertops. Enjoy the expansive backyard complete with multiple fruit trees and patio....Perfect for entertaining! Located blocks from George Hall Elementary School, with close proximity to Caltrain, The Hillsdale Shopping Center, Whole Foods, the Bay Meadows development and convenient access to Highways 101, 92 & 280.

3605 Pacific BLVD, San Mateo

Listed by Dennis Murphy, 415-310-7956 from Golden Gate Sotheby's International Realty
(If provided) CoList: Nicholas Bocci from Bocci Realty, Richard J.

Sold listing courtesy of Les Juan Ruan from KINE
$1,900,000
3 Beds ⋅ 2 Baths ⋅ ML82025070 MLS
Nestled on a charming street, this beautifully maintained home captures the warmth and character that make the Village so special. Step inside to a cozy living room filled with soft natural light that flows throughout the home. The thoughtfully updated kitchen opens to a spacious family room - an ideal spot for movie nights, playtime, or gatherings with friends. The comfortable primary suite provides a peaceful retreat with its own private bath, while two additional bedrooms offer plenty of space for family, guests, or a home office. Outside, escape to your very own private backyard retreat, centered by a beautiful water feature with lush lawn, patio, and plenty of space for outdoor entertaining or peaceful relaxation. Enjoy all that Village living has to offer walk to George Hall Elementary, local parks, Whole Foods, and the vibrant Hillsdale Shopping Center. With easy access to Caltrain and major freeways, youre close to everything yet tucked into a welcoming community that feels like home. A truly special place where comfort, connection, and everyday ease come together.

3513 Casanova DR, San Mateo

Listed by Mani Singh Bhachu, 650-888-0098 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of JJ Team:Jones/Cassel from NTERO
$2,400,000
8 Beds ⋅ ML82022896 MLS
SC Properties is pleased to present. This multi-family property offers a total of 5,740 square feet of living space on a generous 13,500 square foot lot. The property features a beautifully remodeled duplex, each unit offering 2 bedrooms and 2 baths with tasteful finishes throughout. TPO roof on the duplex was installed in 2025, and the sewer lateral was replaced in 2024. The duplex and single-family home have separate utilities. Additionally, there is a spacious 3,500 square foot single-family home with two stories and a basement, providing ample space for a large family. Built in 1935 and recently remodeled in 2016, this property is equipped with modern amenities and individually metered units. The private yards offer a secluded outdoor space for each unit. Located in a desirable neighborhood, this property provides convenient access to Bay Meadows, Hilldale Mall, local schools, parks, and dining options. With parking available in the carport and on the street, tenants will never have to worry about finding a space. Offered at $2,395,000, this multi-family property is the perfect opportunity for investors or those looking to live in one unit and rent out the others. Don't miss out on this rare find.

58 E 39th AVE, San Mateo

Listed by Rachid Atie, 650-868-0202 from SC Properties
(If provided) CoList: Chris Giotinis from SC Properties

Sold listing courtesy of Rinat Kaufman from CBR

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