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Best Places to Shop in San Mateo

10/7/25  |  Stephanie Nash

A Guide to Luxury Destinations for Shoppers in San Mateo.


San Mateo is known for its thriving community, proximity to Silicon Valley, and strong real estate market. Beyond its residential appeal, the city also offers shopping destinations that attract both locals and visitors. For those interested in San Mateo, CA real estate, exploring the retail options highlights the lifestyle opportunities that come with living in this area. Below are some of the best places to shop in San Mateo, with options that align with the preferences of a luxury-minded clientele.

Hillsdale Shopping Center


Hillsdale Shopping Center is one of the most recognized retail hubs in San Mateo. With a mix of well-known national brands, department stores, and specialty retailers, the mall offers a broad range of shopping experiences. Recent updates have added more high-end options, fine dining choices, and modern design elements. Its mix of upscale and practical retailers makes it a cornerstone of shopping in the city.

Draeger’s Market


Draeger’s Market combines gourmet grocery shopping with specialty products that cater to discerning tastes. Known for its extensive wine selection, prepared foods, and high-quality ingredients, it appeals to those who prioritize quality and convenience. Draeger’s also offers a selection of home goods and gift items, making it more than just a grocery store. This market is a well-established part of the San Mateo shopping landscape.

25th Avenue Shopping District


The 25th Avenue Shopping District offers a collection of independent boutiques, specialty shops, and local businesses. Visitors will find clothing stores, jewelry shops, and specialty food retailers. The district maintains a neighborhood feel while offering high-quality goods and services. For residents, it provides a walkable shopping area with a sense of community.

B Street Boutiques and Shops


Downtown San Mateo’s B Street is lined with boutiques and shops that cater to a variety of styles. From clothing and accessories to home décor, this area provides an array of independent retailers. The district is popular with those who enjoy exploring smaller shops rather than large malls. Its proximity to dining and entertainment makes it a convenient destination for a day out.

Sur La Table


Sur La Table is a well-known destination for culinary enthusiasts. The San Mateo location offers professional-grade cookware, kitchen tools, and cooking classes. It appeals to homeowners who want to invest in high-quality products for their kitchens and dining spaces. With its emphasis on premium brands, Sur La Table fits well into San Mateo’s retail environment.

Macy’s at Hillsdale


Macy’s continues to serve as a department store anchor for the area, offering everything from clothing to home furnishings. Its selection appeals to shoppers seeking trusted brands and a wide variety of goods under one roof. The store’s location within Hillsdale Shopping Center ensures convenience for those looking to shop for multiple needs in one visit.

Kiehl’s


For luxury skincare and grooming products, Kiehl’s provides an option for those seeking premium personal care items. Located within Hillsdale Shopping Center, the store offers products known for their quality and effectiveness. Kiehl’s draws shoppers who prioritize wellness and self-care, aligning with a lifestyle that values both appearance and health.

Apple Store, San Mateo


Technology remains an essential part of modern living, and the Apple Store in Hillsdale Shopping Center is a central stop for many shoppers. The store provides access to the latest devices, accessories, and customer support services. Its design and product offerings align with a clientele that values innovation, quality, and integration of technology into daily life.

Nordstrom Rack


Nordstrom Rack gives San Mateo shoppers access to high-end fashion at discounted prices. The store includes clothing, accessories, and home goods, all from premium brands. For residents who want quality items at value, it remains a practical but stylish shopping option. Its location makes it easy to combine with other stops during a shopping trip.

Wine Affairs


Wine Affairs is a boutique wine retailer that caters to collectors and casual enthusiasts alike. The shop offers curated selections of both domestic and international wines, with a knowledgeable staff to assist customers. For those who enjoy entertaining or maintaining a personal cellar, it provides a tailored shopping experience.

About Stephanie Nash


Stephanie Nash has been a licensed real estate professional since 1991 and has lived in the Bay Area her entire life. She is committed to offering her clients reliable service as they navigate the buying and selling process. Known for her attentive approach, honesty, and work ethic, she helps clients find the right home for their needs. Her consistent availability and strong communication skills have set her apart in the industry. Over the years, she has helped many people achieve their goals of homeownership.

Ready to explore real estate in San Mateo, CA? Contact Stephanie Nash today to begin the search for your dream home.



Stephanie Nash

Stephanie Nash

About The Author

For more than three decades, Stephanie Nash has been one of the Peninsula’s most trusted and proven real estate advisors, serving Woodside, Portola Valley, Atherton, Redwood City, Emerald Hills, San Carlos, Half Moon Bay, and the surrounding communities from Burlingame to Los Gatos.

Born and raised on the Peninsula, Stephanie brings true insider knowledge of the region; its micro-neighborhoods, school corridors, country-property enclaves, and the lifestyle features that make this area so coveted: sunny weather, an easygoing spirit, hiking trails, large-parcel retreats, ocean-view hillsides, and world-class food and culture.

A career built on experience, ethics, and results

Stephanie began her real estate career in 1987 working in local title companies before becoming the assistant to a top-producing agent. She earned her real estate license in 1991, and since then has built a reputation as a solutions-driven, ethical, and steady negotiator who guides clients through every complexity of a California transaction.

Her track record includes everything from luxury estates to rural acreage to trust and estate sales, including the successful sale of a 500-acre property, a transaction requiring extensive due diligence, jurisdictional navigation, and long-term strategy.

Nationally recognized performance

Stephanie has been recognized multiple times by RealTrends as one of the “Best Agents in America,” most recently in 2024; an honor reserved for the top tier of agents nationwide based on verified production.

Expert Witness in Real Estate Matters

In addition to client representation, Stephanie now serves as a retained Expert Witness in California real estate cases—including valuation disputes, fiduciary sales, marketing standards, agent performance, disclosure practices, and industry-standard care.

What clients rely on her for

Whether you are buying, selling, downsizing, expanding, or handling a trust/estate sale, Stephanie offers:

  • Deep regional expertise across multiple Peninsula micro-markets

  • Strong negotiation skills grounded in fairness, strategy, and consistent communication

  • Experience in complex transactions (trusts, estates, multiple-heir negotiations, title defects, rural land issues)

  • Compassionate guidance rooted in decades of hands-on client service

  • Unmatched availability and responsiveness

Clients praise her listening skills, honesty, and ability to navigate even the most emotional or complicated sale with clarity and professionalism.

A life built around community and care

Stephanie is deeply grateful for her family, her life on the Peninsula, and the meaningful relationships formed through her work. 

Work With Stephanie

Stephanie respects residential real estate’s dual role as a personal investment and chief financial one. Whether you are buying or selling a home, it will likely be one of the largest financial decisions you make. Stephanie will be with you every step of the way to expertly guide you.

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