Baywood Real Estate

Welcome to Baywood, a charming subdivision nestled in the heart of San Mateo, California. Renowned for its picturesque tree-lined streets and a strong sense of community, Baywood offers a tranquil suburban lifestyle while being just a stone's throw away from the vibrant city life.

Baywood is characterized by its stunning architecture, featuring a delightful mix of classic and contemporary homes that reflect the area’s rich history. Many of these residences boast spacious yards, perfect for family gatherings or enjoying the beautiful California sunshine. The neighborhood is ideal for families, professionals, and retirees alike, offering a welcoming atmosphere for all.

One of Baywood’s standout features is its proximity to top-rated schools, making it a sought-after location for families looking for quality education. The area is served by the San Mateo-Foster City School District, which is known for its commitment to academic excellence. Additionally, residents enjoy easy access to various parks, including the nearby Baywood Park, where you can relish in outdoor activities such as picnicking, jogging, and leisurely strolls.

For those who appreciate the finer things in life, Baywood is conveniently located near a plethora of dining, shopping, and entertainment options. From cozy cafes to upscale restaurants, there’s something to satisfy every palate.

With its perfect blend of suburban charm and urban convenience, Baywood is not just a place to live; it’s a place to thrive. Experience the warmth of community living in this delightful San Mateo subdivision—your dream home awaits!

Newest Listings in Baywood

$1,158,000

4 Beds ⋅ 3 Baths ⋅ 41142674 MLS

Welcoming curb appeal invites you to this expansive 2,474 sq. ft. home featuring 4 bedrooms and 3 baths in the established Upper Baywood neighborhood of Castro Valley. Enjoy stunning panoramic valley views by day and twinkling lights at night from the rear deck & from many rooms inside. Freshly painted interior & exterior, this home has been owned by the same family who appreciated these views along with the home's spacious rooms, flexible floor plan, and abundant storage space for many years . The main level hosts an updated kitchen which opens to the main living areas on either side, along with the primary suite, an additional bedroom and a full bath. Downstairs offers another bedroom, full bath, and a generous bonus room that can serve as a fourth bedroom, home office, family room, or whatever a buyer may need. This level also provides direct access to a large basement/storage area with standing headroom, offering exceptional storage space. Additional highlights include drought-resistant landscaping and a desirable location close to Trader Joe's, shopping, and convenient commuter access. See this special property soon! OPEN Sat. 7/25 & Sun. 7/26 from 1PM-4PM.

21714 Shadyspring Rd, Castro Valley

Listing courtesy of Ted Von Roll from RE/MAX Accord. 510-919-1234

$1,099,998

3 Beds ⋅ 3 Baths ⋅ 41128976 MLS

Back on the market, Professionally Painted, Staged and ready for Immediate Occupancy! Come Check Out this move-in-ready showplace! Fabulous Castro Valley VIEWS! Upgraded kitchen & bathrooms, inside laundry. Hardwood floors. Professionally landscaped, low maintenance yards. The large party deck off the kitchen-family room & dining area is sure to provide countless hours for creating lots of happy memories with family and friends! Just minutes from downtown Castro Valley, BART, both Eden and Kaiser Medical Centers, two International Airports, three Universities and thousands of High Tech, high paying Job Opportunities! If you saw this one before the mid-June upgrades, Come Check this out again! You won't be sorry.

21671 Shady Spring Rd, Castro Valley

Listing courtesy of Steve Moniz from Premier Properties. 510-304-6563

$599,000

41131657 MLS

Is it time to own your practice space and build long-term equity? This highly visible, centrally located ±1,344 sq ft commercial property is thoughtfully configured for healthcare, wellness, or personal service uses. The layout includes multiple treatment rooms—each equipped with a sink—supporting a wide range of professional needs. Currently occupied by a mix of established practitioners, including chiropractors, an aesthetician, and a massage therapist, the space also features a generous waiting area, a reception area with built-in cabinetry, and a private office ideal for administrative work or use as a break room. Located directly across from Trader Joe’s and near popular dining and retail options, the property offers excellent convenience for clients and strong daily visibility. Additional highlights include a ramp to the front door for easy access, three rear parking spaces, and ample street parking. A rare opportunity for a healthcare or wellness professional to own and customize their practice environment in a thriving location.

22179 Redwood Rd, Castro Valley

Listing courtesy of Tannis Kristjanson from Berkshire Hathaway Home Services. 510-459-9065

Start Your Search

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: