429 Virginia Avenue

  • 5

    Beds

    per county records

  • 3.5

    Baths

    per county records

  • 3,270 sq ft

    Home Size

    per county records

  • 8,605 sq ft

    Lot Size

    per county records

For Sale

0 days on market

$3,795,000

Overview

Elevated above the street in the sought-after Baywood neighborhood, this extensively transformed Craftsman home commands sweeping views across the Bay, the San Francisco skyline, and the East Bay hills while offering a rare combination of scale, architectural character, and thoughtfully designed outdoor living. Beautiful stone cladding, tapered columns at the impressive front portico, shingled siding, and bluestone walkways define the authentic Craftsman architecture.

Spanning approximately 3,270 square feet across two levels, the home balances expansive gathering spaces with 5 bedrooms, plus a bonus main-level room/office space and 3.5 bathrooms, thoughtfully arranged for a variety of lifestyle needs. Brazilian cherry wood floors extend throughout, while custom built-ins, skylights, and carefully selected natural stone and tile finishes contribute warmth and sophistication. The foyer and formal living room offer walls of custom cabinetry perfect for the display of books or collectibles. Crowned by a stunning coffered ceiling with skylight, the living room features a gas fireplace with a stone surround and a parade of front-facing windows framing the beautiful views. A spacious dining area, lined with windows looking out to the garden, provides French doors to the covered barbecue patio. The ideally appointed kitchen reflects a clean contemporary aesthetic with sleek taupe cabinetry, granite slab surfaces with full-height backsplashes, a spacious island, a peninsula counter with seating, premium appliances, and a vaulted operable skylight.

The personal accommodations of 5 bedrooms and 3.5 baths are highlighted by a luxurious upstairs primary suite with private balcony, two organized walk-in closets, and a spa-inspired bath with heated floors and oversized curbless shower. A second suite, ideal for guests, is located on the main level, while 3 additional bedrooms are distributed across both levels. Rounding out this versatile floor plan is a bonus main-level room/office space and an upstairs family room with custom cabinetry and wet bar. A detached bonus studio, with wraparound windows, is ideal for an office, fitness center, creative studio, or playroom.

Finishing touches include a laundry room with chute access from upstairs, an attached 2-car garage with finished floor and storage closet, and a privately located spa on the rear grounds. All of this is just one-half mile from downtown San Mateo. Schools: Baywood Elementary, Borel Middle, and Aragon High (buyer to verify).

  • Built in

    1951

  • Listed

    3 hours from now

  • Neighborhood


Amenities

  • Distinctive Craftsman sophistication with sweeping views of the East Bay hills and hills of South San Francisco from its elevated position

  • 5 bedrooms and 3.5 baths on two levels, plus bonus main-level room/office space

  • Approximately 3,270 s/f of living space

  • Detached bonus studio ideal for office, fitness, or playroom

  • Outstanding curb appeal with extensive stone cladding and shingled exterior, classic tapered columns on the front portico, and bluestone walkway with integrated medallion and stairs framed by columns topped with Craftsman lights

  • Craftsman front door with raised dentil detail beneath inset panes of glass

  • Spacious foyer introduces Brazilian cherry wood floors that extend throughout both levels; an entire wall of built-in open shelves adds abundant storage

  • Crowned by a gorgeous coffered ceiling with skylight, the formal living room has seven side-by-side front windows framing Bay, East Bay, and San Francisco views; an entire wall of custom open display cabinetry flanks a gas fireplace outlined to the ceiling in natural stone; an additional wall features cabinetry beneath display shelves; a French door opens to the rear covered porch

  • Designer kitchen features light taupe sleek cabinetry, including island and peninsula counter with seating, all topped in granite slab with full-height backsplashes; an operable vaulted skylight is positioned above the island and a French door opens to a covered rear patio

  • Stainless steel appliances include: Electrolux gas range with 6 burners and pot filler; Sharp microwave; two Bosch dishwashers; separate Electrolux refrigerator and freezer; Zephyr wine cooler

  • Spacious open dining area lined with windows looking out to the rear yard and double French doors to the covered barbecue patio

  • Main-level bedroom suite has front-facing windows, a wall of closets, recessed lighting, and en suite bath with modern wall-mounted stainless steel sink, slate tile floor, and frameless-glass shower with fixed and handheld sprays

  • An additional main-level bedroom with closet and ceiling lighting is served by a hall bath with contemporary glass-topped vanity and dual faucets, travertine floors, corner jetted tub, and frameless-glass shower

  • A large and convenient bonus office is perfect for work-from-home needs

  • Upstairs family/media room with operable skylight, East Bay hill views, wet bar with mini refrigerator, media wall with built-ins

  • Upstairs primary bedroom suite has two organized walk-in closets, sliding glass doors to a balcony, vaulted ceiling, and en suite bath with contemporary glass-topped vanity with dual faucets, heated tile floor with textured leaf patterns, and tiled walls including a curbless shower with pebble stone floor, two ceiling rain showers, and handheld spray

  • Two additional upstairs bedrooms, each with beadboard wainscot and ample closet space, are served by a skylit half-bath with two wall-hung vessel sinks on a wall of glass mosaic tiles (possible plans for conversion to a future full bath are available)

  • Detached studio with reclaimed vintage glass and wood front door plus secondary outside entrance, wraparound windows, coffered ceiling, indoor/outdoor carpet, and two wall sconces

  • Other features: laundry room with Kenmore washer/dryer, outside entrance, and laundry chute from upstairs; attached 2-car garage with finished floor and adjoining storage room; Nest thermostats; wall-mounted air conditioning in main-level bedroom suite; built-in sound speakers in some rooms

  • Inviting rear yard with expansive lawn, privately located spa, basketball area, stone-clad garden beds, utility sink, and covered flagstone patio with built-in barbecue and separate wood-fired rotisserie barbecue

  • Lot size of approximately 8,605 square feet

  • Sought-after Baywood neighborhood, one-half mile from downtown San Mateo

  • Schools: Baywood Elementary, Borel Middle, and Aragon High (buyer to verify)


San Mateo

Baywood

Baywood fits snugly into a corner formed by Alameda de las Pulgas, Crystal Springs Road, and El Camino Real. Notre Dame Avenue separates the neighborhood from Aragon. It is within a brisk walk of downtown San Mateo and a short drive from commute routes and highways 101, 92, and 280, but what brings out the pride in Baywood residents isn’t their comfortable homes, their close-in location, their gently curving streets, or the cache that comes with a Baywood address – it’s their schools.

Among San Mateo neighborhoods, Baywood real estate is surpassed only by the stately mansions of San Mateo Park. Homes in Baywood are larger than those in other neighborhoods, with three, four, or five bedrooms and, as a rule, more than 2,000 square feet of living space. More often, Baywood houses have 2,500 or more square feet, ranging all the way up to 4,000 in some cases. Homes are built in a variety of classic pre-war styles: Spanish, English, Moorish, Tudor, and Colonial, with only a few post-1950 homes mixed in. Lots are larger than those in Aragon or Baywood Knolls, with some rare ones up to 10,000 square feet in size.

Many homes have been updated. Even those that don’t have amenities that were reserved only for the upper class when they were built, like en-suite baths and walk-in closets. Homes rarely come up for sale in Baywood, but when they do, they sell between $3 million and $5 million. The neighborhood median home price in 2025 was $3.7 million, and the average home price was $3.8 million. However, with only 16 home sales in the neighborhood during all of 2025, data can be skewed depending on the mix of homes in any one year. Buyers who like Baywood also generally look for homes in Baywood Knolls, Aragon, San Mateo Park, and the Burlingame neighborhoods of Easton Addition and Burlingame Park.

Baywood is a neighborhood of style and grace. A stroll through its gently curved, wide streets reveals beautifully manicured lawns, children happily (and safely) playing, and driveways full of luxury cars. It is as much an idea as a place – and it’s been that way since the days of John Parrott.

Just nearby Baywood across El Camino, the impressive San Mateo Library is state-of-the-art and tech-smart, and the 16 acre Central Park features the cherish Japanese Tea Garden with its koi pond, where the koi are fed every day at 11 a.m. and at 3 p.m.

To view a detailed google map of the Baywood neighborhood, click here. The MLS area is 438.

Explore Baywood

San Mateo has it all: a diversity of neighborhoods, great parks, easy access, a plethora of shopping, and home to many businesses and an anchor for employment on the peninsula. With a rich heritage, dating back to the turn of the century with its most famous resident being A.P. Giannini, the founder of the Bank of Italy and later Bank of America, San Mateo offers a delightful spread of activity for all. The downtown area is studded with delicious restaurants and a variety of retail stores, and also boasts a 12 screen movie theatre and one of the largest wine cellars in the country, at Draeger’s Grocery Store. Shopping abounds at Hillsdale and Bridgepointe as well as the many neighborhood shopping centers.

Perhaps the most well known natural area is Coyote Point, a rock outcropped peninsula that juts into San Francisco Bay and home to a natural history museum, the Peninsula Humane Society, windsurfing, a private marina, and large picnic areas with uplifting vistas. Within walking distance of downtown, Central Park has something for everyone: ride the toy train, pick up a game of tennis, take a serene walk through the Japanese Garden, have a picnic while listening to Thursday evening’s Jazz in the Park, or enjoy the playgrounds.

San Mateo attracts a variety of homeowners, from those seeking their first home in the upcoming neighborhoods of the Village, Parkside, or Shoreview, to those looking for more a little more space in Hillsdale or the Meadows, to larger families seeking the spaciousness offered by San Mateo Park, Baywood, and Aragon.

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Small town feel
Big-city downtown amenities with a small town residential neighborhood feel
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Diverse housing
Very diverse housing opportunities ranging from downtown condos to suburban ranches and secluded San Mateo Park mansions
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Top schools
Baywood schools ranked among the state’s best
Explore San Mateo

Early San Mateo was a place of large estates and boldface names familiar to anyone who’s driven the town’s streets. Parrott, Hayward, Borel—these were the wealthy pioneers who sowed the seeds that eventually grew into today’s modern city of 100,000 residents. San Mateo was borne from their needs and later from their subdivided land, all around a stagecoach stop established in 1849 by Nicolas de Peyster on former Ohlone tribal land.

Team photo.

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