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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

Luxury real estate agent Stephanie Nash was born and raised on the Peninsula. She currently serves the communities of Woodside, Portola Valley, Atherton, Half Moon Bay, San Carlos, Redwood City, Emerald Hills, and the surrounding areas, from Burlingame to Los Gatos. According to Stephanie, there is so much to love about this area, including the sunny weather, easygoing lifestyle, and the abundance of country property with large parcels, hiking trails, ocean views, and great food.
 
In 1987, Stephanie began her illustrious career in real estate by working in title companies, eventually moving into an assistant role for a top-producing agent. She became a licensed real estate agent herself in 1991. Since then, she has forged a stellar reputation as a trusted advisor for her clients; a compassionate and solutions-driven professional, Stephanie’s clients know that when they work together, they are on track to achieve their real estate goals.
 
With over 30 years of experience in real estate, clients can count on Stephanie to help them find the perfect home. Whether they’re moving to a larger house for their growing family, downsizing to a cozy home, or finding the perfect property with sprawling acres of land, Stephanie knows how to handle each and every situation. She is a great listener, honest navigator, and hardworking agent with a positive attitude and strong ethics. Stephanie's availability and good communication skills set her apart from the competition, and she is proud to have helped many clients achieve their dream of homeownership – including a tremendous sale of a 500-acre property. 
 
Stephanie is grateful for her life, her beloved children, and the wonderful people she meets through her work. In her free time, Stephanie enjoys swimming, spending time with her dog at the beach, cooking for friends and family, and starting a new hobby as a gardener and caretaker for her plants and 13 chickens. 
 

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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