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3023 Del Ray Street, San Mateo
$2,048,000
3 Beds ⋅ 2 Baths ⋅ ML82066033 MLS
At the base of the San Mateo Terrace foothills, 3023 Del Ray Street is a 3-bedroom, 2-bath home in San Mateo's Beresford Park neighborhood, offering 2,116 sq ft of character and modern comfort. Colorful gardens and a paver walkway welcome you inside, where hardwood floors, arched doorways, crown molding, and a wood-burning fireplace reflect its 1946 origins. A skylit dining room leads to a thoughtfully updated kitchen, where quartz counters, a marble chevron backsplash, and a Thermador appliance suite make cooking and entertaining a pleasure. A center island with microwave drawer and a breakfast bar connect the kitchen to the family room, where sliding doors open to a Trex deck with peekaboo Bay and East Bay hill views. Below, a paver patio framed by mature maples, roses, and lavender invites outdoor gatherings. Three main-level bedrooms are complemented by a separate lower-level wing with flexible spaces for guests, recreation, entertaining, or working from home. Two updated baths, an 11-kW Generac generator, and an attached garage with laundry and storage add everyday ease. Enjoy nearby Beresford Park, 25th Avenue dining, Hillsdale Shopping Center, Bay Meadows, and Hillsdale Caltrain.

3023 Del Ray Street, San Mateo

Listing courtesy of Rumana Jabeen from KW Advisors. 650-743-4503

1242 Shafter Street, San Mateo
$2,498,000
3 Beds ⋅ 2 Baths ⋅ ML82064601 MLS
This beloved Colonial pairs classic traditional character with stylish touches, and it feels special the moment you walk in. Sunlight fills every room, highlighting hardwood floors and elegant crown molding. The stunning living room invites gathering, with a cozy fireplace and French doors that bring the outdoors in. The casual dining room, framed by picture windows, is perfect for holiday dinners and celebrations. The home has an updated and inviting kitchen and family room, the true heart of the home. French sliders lead to an expansive backyard, ready for summer barbecues, weekend play, or simply relaxing outside. An ideal floor plan, indoor laundry room, and two-car garage, office or studio make everyday living easy. Walkable to downtown, parks and all the top rated schools. All of this is in the sought-after Baywood/Aragon school district. Come see where your next chapter begins.

1242 Shafter Street, San Mateo

Listing courtesy of Gillian Kilroy from Compass. 650-868-2644

104 Franklin Parkway, San Mateo
$2,199,000
4 Beds ⋅ 4 Baths ⋅ ML82065961 MLS
Spectacular living in one of the most desirable floor plans! Offering nearly 2,500 square feet of beautifully designed living space, this stunning home combines modern elegance, spacious interiors, and an unbeatable location. Soaring ceilings, an open-concept floor plan, abundant natural light, and gorgeous wide-plank flooring create a bright and airy atmosphere throughout. At the heart of the home is the expansive chefs kitchen flowing to the dining and living rooma standout feature of this highly sought-after floor planoffering exceptional space for cooking, entertaining, and gathering with family and friends. Upstairs, you'll find three generously sized bedrooms connected by a spacious hallway with convenient built-in storage. The sun-drenched primary suite is a true retreat, featuring a walk-in closet, private patio, and luxurious ensuite bath with dual vanities, an oversized walk-in shower, and separate water closet. The lower level offers incredible flexibility with a spacious fourth bedroom or family room, complete with its own ensuite bathroom and walk-in closet. Attached two-car garage with an EV outlet. Love life in Bay Meadows - moments from Caltrain, Whole Foods, Paddock Park, Hillsdale Shopping Center, and an array of shopping, dining, and everyday amenities.

104 Franklin Parkway, San Mateo

Listing courtesy of from Compass. 650-678-5455

1315 Maple Street, San Mateo
$1,875,000
2 Beds ⋅ 2 Baths ⋅ ML82065243 MLS
Welcome to this charming home in a sought-after San Mateo neighborhood, offered for the first time in over 40 years. Set on a manicured corner lot, the home offers a gracious formal entry and a thoughtfully designed floor plan featuring beautiful hardwood floors, an inviting living room with a cozy gas fireplace, and a spacious adjoining dining area. Elegant plantation shutters throughout the home beautifully filter natural light, creating a warm ambiance. The kitchen retains its vintage character, while a separate laundry/utility room provides access to the back porch and yard. Two bedrooms and a hall bathroom complete the main living spaces. An approximately 490-square-foot garage features two windows providing natural light, a convenient storage loft, and a 2nd full bathroom. The spacious backyard provides an inviting setting for outdoor entertaining, relaxation, and gardening. Established landscaping, including mature Fuji apple and fig trees, adds to the property's appeal. Notable improvements include a new roof in 2025 and a recently replaced sewer lateral. Nearby schools include highly rated Baywood Elementary, Borel Middle, and Aragon High School. Conveniently situated near parks, shopping, dining, and downtown San Mateo, this cherished home is ready for its next chapter.

1315 Maple Street, San Mateo

Listing courtesy of Tim Allen Alevizos from Remax Capital. 650-255-7635

2800 Monterey Street, San Mateo
$2,998,000
4 Beds ⋅ 3 Baths ⋅ ML82065164 MLS
Expanded and fully remodeled, this beautifully reimagined 4-bedroom, 3-bath San Mateo home offers approximately 2,341+/- square feet of thoughtfully designed living space on a 7,583+/- square foot lot. An inviting front porch, cascading entry steps, and striking solid wood front door introduce light-filled interiors with vaulted ceilings, oversized windows, and an open-concept floor plan. The designer kitchen features a generous island with prep sink and flows seamlessly into the living and dining spaces, accented by statement lighting and custom metal and fluted wood shelving. The main-level features three bedrooms, with the primary suite offering a spa-inspired bathroom. Upstairs one additional en suite provides privacy alongside a flexible bonus space and additional storage. The beautifully landscaped backyard features turf lawn, new plantings, and a magnificent sculpted California live oak highlighted by landscape lighting. Additional amenities include air conditioning, an expansive driveway, multi-car garage with epoxy flooring, and EV-ready electrical infrastructure. Conveniently located near parks, shopping, dining, and neighborhood amenities, this home blends modern style, comfort, and exceptional indoor outdoor living.

2800 Monterey Street, San Mateo

Listing courtesy of from KW Advisors. 650-766-5333

171 Starlite Drive, San Mateo
$2,689,000
3 Beds ⋅ 3 Baths ⋅ ML82065545 MLS
With picture-perfect curb appeal, a great room with big sunny windows, a backyard view deck, and a superb Baywood Park location, this lovely home is ideal for California indoor/outdoor living. Just behind a picket fence, the lush front yard boasts a variety of plantings and a walkway leading to an inviting covered porch. Inside, glowing hardwood floors, natural brick accents, and high ceilings enhance the sense of volume throughout the entertainment and private spaces. Highlights of the 3- bedroom, 3-bath floor plan include a light-filled primary suite and a second bedroom with en suite bath. The backyard features an expansive view deck for enjoying the treetop vistas and a dining patio with pergola. Combining serenity with convenience, this wonderful retreat is just minutes to commute routes, shopping and dining, sought-after schools, plus hiking and biking at beautiful Crystal Springs Reservoir.

171 Starlite Drive, San Mateo

Listing courtesy of Erica Damelio from Compass. 650-571-8000

509 Crescent Avenue, San Mateo
$3,888,000
5 Beds ⋅ 4 Baths ⋅ ML82065540 MLS
Set on an expansive 8,670-square-foot lot in coveted San Mateo Park, 509 Crescent Avenue offers an exceptional blend of timeless character, privacy, and effortless indoor-outdoor living. A gracious formal living room and elegant dining room create beautiful spaces for entertaining, while the kitchen serves as the heart of everyday life, opening naturally to the backyard. Outside, a generous lawn framed by mature trees creates a private setting for play, gatherings, and relaxed afternoons at home. Inside, approximately 2,940 square feet unfold across a versatile five-bedroom, four bath floor plan. Two bedrooms on the main level offer flexibility for guests, a home office, or multigenerational living, while upstairs are three additional bedrooms, including the primary suite and two secondary bedrooms that share a full bath. A generous family room provides additional space to gather, and a detached two-car garage adds convenience and flexibility. Enjoy all that San Mateo Park has to offer tree-lined streets, beautiful homes, neighborhood block parties, and walkability. Just minutes from downtown Burlingame, 509 Crescent offers a rare combination of space, privacy, charm, and convenience in one of the Peninsulas most beloved neighborhoods.

509 Crescent Avenue, San Mateo

Listing courtesy of from Compass. 650-678-5455

27 Condon Court, San Mateo
$2,898,000
3 Beds ⋅ 3 Baths ⋅ ML82065358 MLS
Welcome to 27 Condon Court... An outstanding San Mateo location in the sought-after Laurelwood neighborhood. This light, bright, airy 3-bedroom, 2.5-bathroom home was originally built in 1973 and has been lovingly updated and maintained by its current owner for many years. The lower level or main level, features high ceilings and a free-flowing floor plan that opens to an outdoor entertaining patio and the rear garden with breathtaking canyon and San Francisco Bay Views. The custom-built 3-hole golf putting green is the centerpiece of this lovely outdoor space. The 2nd floor has an oversized primary suite and two modest bedrooms. There is space to create an additional bedroom. This home has been recently enhanced by many cosmetic updates, including new floors, painting throughout, new light fixtures and light kitchen and bathroom improvements. Laurelwood Park, a 225-acre public open space located is only blocks away. The popular Laurelwood Shopping Center is also blocks away. Award-winning schools are nearby, including the College of San Mateo. This desirable neighborhood blends classic mid-century suburban comfort with immediate suburban conveniences. Easy access to SR-92, Interstate 280, 101 and Highway 1 and SR-35 (Skyline Blvd). We are move-in ready for you. Welcome Home!

27 Condon Court, San Mateo

Listing courtesy of Ken Constantino from Compass. 650-814-0277

1408 Royal Avenue, San Mateo
$1,398,000
3 Beds ⋅ 3 Baths ⋅ ML82065517 MLS
Ready to be Re-Imagined! Situated in San Mateo's desirable South Shoreview neighborhood, this 3-bedroom, 3-bathroom residence offers approximately 1,790 square feet of interior living space and an exceptional opportunity to bring your vision to life. Ready to be reimagined, the home features a versatile layout with exciting potential to create a sophisticated, personalized retreat tailored to today's lifestyle. Generously proportioned interiors provide a wonderful canvas for thoughtful design and modern enhancements. Conveniently located with easy access to major commute routes, this property blends opportunity with everyday practicality. A wonderful opportunity to transform this residence into something truly special in a well-established San Mateo neighborhood.

1408 Royal Avenue, San Mateo

Listing courtesy of Cory Cooper from JetSet Homes. 650-921-9855

422 Peninsula Avenue, San Mateo
$1,780,000
ML82065454 MLS
422-426 Peninsula Ave presents a rare owner-user or investment opportunity located on the border of San Mateo and Burlingame (Currently 100% Vacant, Situated on a 6,098 square foot parcel of land, the subject property was originally constructed in 1954, offering approximately 3,456* square feet of net rentable square feet. 422-426 Peninsula Ave is currently built out as 3 separate suites but can be reconfigured to cater leasing needs. The property benefits from its strategic Peninsula Ave location, providing convenient access to both San Mateo and Burlingame and proximity to major transportation corridors, established residential neighborhoods, and a broad range of retail and commercial amenities. The surrounding area features a diverse mix of office, flex, retail, and residential uses, supporting the property's appeal to a variety of local businesses and professional users. With its attractive Peninsula location, flexible configuration, and multiple potential use strategies, 422-426 Peninsula Ave offers a compelling opportunity for an owner-user or investor seeking well-located commercial real estate in the San Mateo/Burlingame market.

422 Peninsula Avenue, San Mateo

Listing courtesy of Cole Simpson from Marcus & Millichap. 650-391-1735

115 10th Avenue, San Mateo
$2,400,000
4 Beds ⋅ 3 Baths ⋅ ML82065440 MLS
OFFERS DUE MONDAY(2nd) @ 12Noon Welcome home to a private, gated retreat in San Mateo's highly desirable Hayward Park neighborhood, close to downtown. Set back behind a wrought-iron gate, lush landscaping, and a towering palm, this sunny 4 bed, 3 bath home is freshly painted inside with new lighting throughout. A formal entry opens to refinished red oak floors on the first level and stairs. The living room offers a bay window, built-in shelving, and a newly tiled fireplace. The formal dining room opens to the rear yard and features a magnetic metal wall for art. The large kitchen has quartz counters, skylights, under-cabinet lighting, double ovens, a breakfast bar, and a sunny nook. First-floor bedroom with built-in desk plus a full bath. Upstairs, new carpet and an opening stairwell skylight. The large primary retreat has an arched window, a huge walk-in closet, and a bath with walk-in shower and opening skylight. Hall bath with new quartz counter and ample storage. Out back, a private yard with deck, patios, a screenhouse with raised beds, and a detached building for a workshop, studio, gym, or potential ADU, with 220V and exhaust. Owned solar, two furnaces, water filtration, auto drip and landscape lighting. One-car garage plus storage!

115 10th Avenue, San Mateo

Listing courtesy of Christopher Eckert from KW Advisors. 650-627-3799

3809 Colegrove Street, San Mateo
$1,398,000
2 Beds ⋅ 1 Baths ⋅ ML82065217 MLS
Pride of ownership! Offer date: Mon Nov 2 by 3:30 R2 Zone. This truly unique home is exceptional for casual living and designed for entertainment. The backyard gazebo extends the living space for al fresco dining, complemented by a covered, year-round built-in rotisserie grill. The detached two-car garage has been upgraded with heating, air conditioning, and a full bathroom, making it a perfect home office or multipurpose space. Outside, the yard features solid fencing for privacy, artificial turf for low maintenance, custom rolling storage cabinets, additional built-in storage throughout, and a dedicated greenhouse area for growing vegetables. Additional key features include: - R2 Zoning - 12-panel solar system for energy efficiency - Updated front yard for maximum curb appeal - Central A/C and double-pane windows - New appliances and porcelain tile kitchen flooring - Upgraded 200-amp electrical panel - Skylight and Jacuzzi The location is ideally situated close to shopping, schools, restaurants, and major freeways. A full feature list will be available to pick up during the open house

3809 Colegrove Street, San Mateo

Listing courtesy of Michele Dee from Better Homes and Gardens RE Reliance. 650-455-2260

710 Laurel Avenue, San Mateo
$14,950,000
ML82065118 MLS
MNM Realty Group is pleased to offer 14 tenant-in-common (TIC) positions in Park Laurel Apartments. Together they make up a 64.75% undivided interest in a renovated 26-unit apartment community at 710 Laurel Avenue, bordering Central Park in downtown San Mateo. Individual positions range from 0.70% to 32.00% and may be bought on their own or combined. Each is priced pro rata to a $14,950,000 property valuation ($575,000 per unit). The property has received more than $1.3 million in capital improvements, including a seismic retrofit. Eighteen of the 26 units have been fully renovated with in-unit washer/dryers, new kitchens and modern baths. Amenities include a heated pool, a rare feature in the area, and the property has a Walk Score of 97. It sits about 2 miles from Burlingame Avenue and 10 minutes from SFO. TIC positions offer investors a fractional entry into a supply-constrained Peninsula multifamily asset with remaining value-add upside as market rents continue increasing

710 Laurel Avenue, San Mateo

Listing courtesy of Jake Anthony from MJA Equity Investments, Inc.. 650-787-6707

3726 Branson Drive, San Mateo
$1,488,000
2 Beds ⋅ 1 Baths ⋅ ML82062264 MLS
Welcome to 1326 Branson, located in the highly sought-after San Mateo Village neighborhood. This charming 2-bedroom, 1-bath home offers 920 sq. ft. of living space plus approximately 275 sq. ft. of additional space, offering flexibility for a family room, home office, playroom, or entertaining area. Inside, hardwood floors add warmth and character, while a wood-burning fireplace creates a cozy focal point in the additional living area. The light-filled kitchen features a skylight along with a gas cooktop, dishwasher, microwave, and refrigerator, and opens to an adjacent dining area for easy everyday living. Situated on a 5,000 sq. ft. lot, the property also features a one-car garage with laundry area, washer and dryer, an existing storage shed, and plenty of opportunity to make the outdoor space your own. Conveniently located near shopping, dining, transportation, and major commute routes, this San Mateo Village home offers a wonderful opportunity to enjoy one of San Mateo's most desirable neighborhoods.

3726 Branson Drive, San Mateo

Listing courtesy of Gary Mano from Intero Real Estate Services. 408-315-5086

no property photo
$2,798,000
3 Beds ⋅ 2 Baths ⋅ ML82064984 MLS
This absolute jewel is ideally situated in the heart of The Lanes, across from a hidden park and readily accessible to everything including shopping, transit, schools, dining and entertainment. Upon entering, the outdoor room and garden beyond the wall of bay windows beckon you. The open floorplan, enormous kitchen and high-end finishes provide for seamless indoor/outdoor living and entertaining. The kitchen features custom cherrywood cabinetry, soapstone countertops, abundant storage with pullout drawers, and an extra-deep stainless-steel sink. A Thermador gas 5-burner stove, electric double ovens (convection) and a large kitchen island create a space for both serious cooking and casual entertaining. The covered patio serves as an outdoor room featuring cabin-style rustic wood beams overhead, a cozy stone fireplace and an outdoor TV. An overhead fan and heaters enable year-round comfort. Shaded gravel pathways lead to a hidden vegetable garden and a detached studio, offering a private and tranquil space for work or creative pursuits. Just across the street and down a discreet pathway lies the hidden East Hillsdale Park a local treasure. Beautifully crafted and stewarded, this home offers the best that mid-peninsula living has to offer.

151 Louise Lane, San Mateo

Listing courtesy of Philip Watson from Christie's International Real Estate Sereno. 650-274-5187

2015 Ticonderoga Drive, San Mateo
$2,488,888
3 Beds ⋅ 2 Baths ⋅ ML82065002 MLS
Set on a quiet cul-de-sac, this 3 Bedroom 2 Bath home sits on an oversized 12,638 sq. ft. lot, blending iconic mid-century design. One of the largest level lots in the SM Highlands for expansion possibilities. The 1,650 sq foot layout flows effortlessly from living and dining spaces to outdoor entertaining areas, ideal for both everyday living and hosting large events. Floor to ceiling walls of glass w/original Mahogany wood paneling. A permitted free-standing studio adds flexible space for a home office, gym, or artist workshop. Recently epoxied 2-car garage floor. Resealed Foam roof. Sewer lateral replaced in 2025. Successor Trustee sale with limited disclosures. This original owner home has been cared for since 1958. Staged for the fall season with a pumpkin patch to show off the generous sized grounds! Rec center includes community pool, tennis courts, and after school programs. Sawyer Camp Road close by for walking, jogging, plus bike trails along the Crystal Springs reservoir. Close to Highlands Elementary School. In the Aragon High School district. Location! Location! Location!

2015 Ticonderoga Drive, San Mateo

Listing courtesy of Glenn Sennett from Coldwell Banker Realty. 650-208-7355

20 W 3rd Avenue Unit #601, San Mateo
$2,500,000
2 Beds ⋅ 3 Baths ⋅ ML82064960 MLS
NEW PRICE!! Welcome to luxury living at the Towers in the heart of San Mateo! This stunning 2BR/2.5BA condo offers an expansive 2,800 SF of modern elegance. Step inside to find high ceilings, sleek hardwood floors, recessed lighting, and plenty of natural light streaming through a multitude of windows. The open layout features a spacious foyer, formal dining room, and a cozy library/den, perfect for working from home or unwinding. The sunlit kitchen is complete with a breakfast nook, cooktop, range hood, dishwasher, refrigerator, and even a wine cooler for entertaining. The private primary ensuite boasts a walk-in closet, a large shower and generous primary bedroom. A small private patio off kitchen offers a serene outdoor space, while the building includes shared rooftop deck, patios, and common outdoor areas. Amenities include pool/spa, sauna, gym, game room, and media/recreation room. With a doorman, elevator access, & security features like an electric gate and voice intercom, convenience and peace of mind are yours. Add'l features include central AC/heating, an in-unit washer/dryer and private storage Located near downtown San Mateo, this condo combines convenience, style, and easy access to downtown restaurants, shops and library

20 W 3rd Avenue Unit #601, San Mateo

Listing courtesy of Susan Herman from Compass. 650-400-4383

934 S Delaware Street, San Mateo
$1,825,000
4 Beds ⋅ 2 Baths ⋅ ML82064947 MLS
Charming 1930s Home Near Downtown Offering Flexible Multi-Unit Living Owned by the same family for over 60 years, this multi-unit property is located just blocks from downtown dining and Central Parks tranquil Japanese Garden. It offers exceptional flexibility for investment income, owner occupancy or a combination of both, while retaining many of its original character details. Tudor half-timbering accents and fresh landscaping enhance the exterior, while newly painted interiors, high coved ceilings, and refinished hardwood floors create a fresh, move-in-ready feel. A large, sunny, two-level deck extends between the two rear units, providing generous outdoor living space, while substantial off-street parking adds valuable convenience. Multi-unit property with investment income potential and flexibility for owner occupancy (permit status unknown) Two-story 4-bedroom, 2-bath main home; approx.1,942 square feet Detached garage (partially converted) with adjoining 1-bedroom, 1-bath unit; approx. 500 square feet (Non Permitted) 1-bedroom, 1-bath unit with separate address (936 S. Delaware Street); approx. 468 square feet Fresh paint inside and out and updated flooring in all units Significant off-street parking Just one-half mile from downtown San Mateo

934 S Delaware Street, San Mateo

Listing courtesy of Ryan Gowdy from The Agency. 408-309-8660

934 S Delaware Street, San Mateo
$1,825,000
ML82064948 MLS
Charming 1930s Home Near Downtown Offering Flexible Multi-Unit Living - Main House & 2 units Owned by the same family for over 60 years, this multi-unit property is located just blocks from downtown dining and Central Parks tranquil Japanese Garden. It offers exceptional flexibility for investment income, owner occupancy or a combination of both, while retaining many of its original character details. Tudor half-timbering accents & fresh landscaping enhance the exterior, while newly painted interiors, high coved ceilings, and refinished hardwood floors create a fresh, move-in-ready feel. A large, sunny, two-level deck extends between the two rear units, providing generous outdoor living space, while substantial off-street parking adds valuable convenience. Multi-unit property with investment income potential and flexibility for owner occupancy Two-story 4-bedroom, 2-bath main home; approx.1,942 square feet Detached garage (partially converted) with adjoining 1-bedroom, 1-bath unit; approx. 500 square feet (Non permitted) 1-bedroom, 1-bath unit with separate address (936 S. Delaware Street); approx. 468 square feet Fresh paint inside and out and updated flooring in all units Significant off-street parking Just one-half mile from downtown San Mateo

934 S Delaware Street, San Mateo

Listing courtesy of Ryan Gowdy from The Agency. 408-309-8660

24 N Idaho Street, San Mateo
$1,388,000
3 Beds ⋅ 2 Baths ⋅ ML82064914 MLS
Welcome to 24 N Idaho, a thoughtfully reimagined 3-bedroom, 2-bath home where every detail has been renewed to match the way people want to live today. The layout opens directly to the backyard, creating an easy, natural flow between indoor living and the outdoors that makes everyday life and entertaining feel effortless. Inside, entirely new interiors are filled with natural light from morning through evening. The kitchen is the heart of the home, finished with brand-new appliances, fresh cabinetry, and refined surfaces that balance clean, modern style with everyday function. New finishes carry throughout every room, giving the home a bright, cohesive feel that is ready for you to move right in. The real treasure in this home is the expansive lot - 7,828 square feet, offering a rare sense of space for the area. There is room to garden, play, gather with friends, or simply unwind outside, along with exciting potential to add an ADU for extended family, guests, a home office, or rental income. Downtown San Mateos restaurants, caf s, shops, and Caltrain are moments away, and quick access to Highway 101 makes commuting up and down the Peninsula remarkably easy. It is a home that offers both a relaxed, light-filled retreat and an exceptionally connected lifestyle.

24 N Idaho Street, San Mateo

Listing courtesy of Lailah Morris from KW Advisors. 650-740-1066

1455 Ascension Drive, San Mateo
$2,895,000
4 Beds ⋅ 3 Baths ⋅ ML82064849 MLS
Surrounded by mature trees in desirable Baywood Park is a beautifully updated 4 bed, 3 bath home offering approximately 2,260 sq ft of stylish living and inviting indoor-outdoor spaces. Thoughtfully refreshed throughout with new windows, new hardwood floors, a new deck, a new fire pit, and refreshed landscaping. An open living and dining area welcomes you with abundant natural light, a cozy fireplace, and wide-plank flooring. The skylit kitchen features warm wood cabinetry, a statement range, generous counter space, and ample seating, creating an ideal setting for everyday living and entertaining. Step outside to the expansive new deck, perfect for al fresco dining and relaxing with a new fire pit creating the perfect gathering spot. The spacious primary suite offers a well-appointed bath with dual sinks and a separate tub. A lower-level bedroom and full bath provide flexibility for guests, extended family, or a home office. A dedicated laundry room, additional storage, and attached garage complete the homes thoughtful amenities. Enjoy close proximity to Crystal Springs Shopping Center, scenic Crystal Springs trails, and convenient access to Highways 92 and 280. A wonderful opportunity to enjoy modern comfort, natural beauty, and the best of Peninsula living.

1455 Ascension Drive, San Mateo

Listing courtesy of from KW Advisors. 650-465-5742

3605 Kingridge Drive, San Mateo
$2,899,888
4 Beds ⋅ 2 Baths ⋅ ML82064445 MLS
A rare opportunity in San Mateo's desirable Knolls neighborhood! Custom-built in 1957 and cherished by the same family for nearly 70 years, this exceptional home is offered for the first time. Nestled on a secluded, nearly half-acre lot, the property offers privacy, space, and effortless single-level living. With 2,290 sq. ft., the home features 4 bedrooms and 2 bathrooms; beautifully updated kitchen and baths. The thoughtfully designed floor plan separates lively gathering spaces from the peaceful bedroom wing, offering an ideal balance of entertaining and everyday comfort. Light-filled living areas and expansive windows seamlessly connect indoors and out. The true showstopper is the resort-inspired backyard, featuring a sparkling pool, pool house, overlook deck, and generous entertaining spaces. Mature trees and lush surroundings create a private retreat. Ample additional parking alongside the home adds convenience and flexibility offering additional parking for cars or guests. Moments from Sugarloaf Open Space, scenic trails, parks, and schools, this special property is ready for its next chapter. Welcome to The Knolls Haven!

3605 Kingridge Drive, San Mateo

Listing courtesy of Rosa Baltodano from Compass. 650-267-1548

155 12th Avenue, San Mateo
$2,250,000
3 Beds ⋅ 2 Baths ⋅ ML82064811 MLS
Craftsman charm, an exceptional kitchen, and a private backyard retreat in San Mateos Hayward Park. Shingle-clad 3-bedroom, (PLUS OFFICE) 2-bath home blends timeless architectural details with thoughtful updates. Beautifully maintained hardwood floors, a wood-burning fireplace, and classic Craftsman built-ins bring warmth and character to the main level. A welcoming covered entry overlooks a magnificent green maple tree. The extensively updated kitchen features wood cabinetry, granite countertops, a breakfast bar, abundant storage with pullouts, and an extra-deep stainless steel sink. A 48-inch Wolf range with double ovens, griddle, and indoor grill anchors the kitchen, complemented by a built-in fryer, pot filler, LG refrigerator and double-drawer beverage refrigerator. An adjoining laundry room adds everyday convenience. Two generously sized bedrooms and a full bath occupy the main level, while the thoughtfully converted, permitted upper level offers two additional bedrooms, a full bath, and a family room. Outside, the private backyard features beautiful stonework, a sauna, lemon tree, and ample side-yard space. A two-car garage includes EV charger and a built-in workshop completes the property. Enjoy downtown shopping and dining nearby, plus convenient access to Caltrain

155 12th Avenue, San Mateo

Listing courtesy of from Compass. 650-678-5455

221 N Delaware Street, San Mateo
$1,198,000
3 Beds ⋅ 2 Baths ⋅ ML82064806 MLS
An extra-deep lot in downtown San Mateo with two units and room to grow. Built in 1907, this single-family home retains its original character, including an enclosed front porch. It has been converted so that each unit has its own full kitchen and bath. The front unit offers 2 bedrooms and 1 bath, and the back unit offers 1 bedroom and 1 bath. New heating and air conditioning are already in place. The possibilities are wide open. Live in one unit and let the rent from the other help cover the mortgage. Use both for multigenerational living, with privacy and independence under one roof. Or add it to your portfolio as a two-unit investment. The property is delivered vacant, so you can set your own rents and move at your own pace. Out back, the oversized yard is a rare find in such a central location. Mature fig and lemon trees frame a generous space for gardening and entertaining, with the potential to expand the existing home or add another dwelling. A detached garage and long driveway offer off-street parking, along with flexibility for storage, a workshop, or a possible future ADU conversion. Walk to the shops and restaurants of downtown San Mateo, with Caltrain and Hwy 101 close by for an easy commute anywhere on the Peninsula.

221 N Delaware Street, San Mateo

Listing courtesy of Michael Mclean from Coldwell Banker Realty. 650-240-6566

421 W 39th Avenue, San Mateo
$1,789,000
3 Beds ⋅ 2 Baths ⋅ ML82064798 MLS
Views! Views! Views!!!!!! Perched atop a hillside, this residence offers breathtaking, excellent views that stretch across the expansive San Francisco Bay to the East Bay Hills. This elevated ranch-style home is perfectly situated within the highly sought-after and prestigious Westwood Knolls neighborhood, known for its charm and tranquility. The residence features three generously sized bedrooms, highlighted by an expansive primary suite designed for comfort. The full-sized kitchen serves as a functional heart of the home, complete with a charming breakfast nook and convenient, direct access to the private rear yard, perfect for seamless indoor-outdoor living. The interior is anchored by an expansive L-shaped living and dining area, which serves as a stunning vantage point for taking in the impressive northern vistas of the city skyline and the shimmering bay. The living spaces are elegantly finished with classic hardwood floors and benefit from the efficiency and clarity of updated dual-pane windows throughout. Additionally, the property includes a spacious two-car garage. With its exceptional layout and inherent potential, this property presents a remarkable opportunity to customize and create a personalized sanctuary that perfectly reflects your unique lifestyle.

421 W 39th Avenue, San Mateo

Listing courtesy of Charles Floyd from Compass. 650-892-3464

Bay East © 2026. CCAR © 2026. BridgeMLS © 2026. Information Deemed Reliable But Not Guaranteed. This information is being provided by the Bay East MLS, or CCAR MLS, or bridgeMLS. The listings presented here may or may not be listed by the Broker/Agent operating this website. This information is intended for the personal use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on:

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