Buying a Home in Hillsborough

Sternsmith Group


Welcome to the prestigious enclave of Hillsborough, nestled in the verdant hills north of Silicon Valley, where timeless elegance, a storied history, and refined living harmoniously converge. This alluring community, celebrated for its opulent estates and majestic surroundings, exudes an air of sophistication that captivates the discerning few who call it home.

The choice of making Hillsborough your new home is indeed a wise one — with excellent schools, gorgeous golf courses, outdoor spaces, and scenic views of San Francisco Bay, you will never tire of the stunning landscape and incredible amenities here.

The Hillsborough real estate scene is truly unparalleled, offering luxury living at every turn. As you traverse the tree-lined streets, each estate presents itself as a masterpiece of architectural brilliance, meticulously designed to blend perfectly with its natural surroundings. Graceful mansions adorned with grand facades and stately columns stand as a testament to the artistry and craftsmanship that define Hillsborough's luxury real estate landscape.

Every corner of this illustrious town is adorned with lush lawns and manicured gardens, offering a symphony of colors. The serene beauty of the surroundings creates a seamless connection between the grandeur of the residences and the tranquility of nature. Not only that, but Hillsborough residents enjoy an easy trip to San Francisco and all that the big-city life has to offer.

If you’re considering calling Hillsborough your new home, read on for everything you need to know to get started!

A closer look at the Hillsborough real estate market trends

As we step into the real estate sphere of gorgeous Hillsborough, there's a rich tapestry of information to decipher. Considering the 2023 housing market trends, the typical selling price for homes in Hillsborough rests around the $6,780,000 mark, according to the latest data from the California Association of Realtors. As the data reflects, the Hillsborough housing market commands soaring prices with unparalleled luxury properties.

The local housing market's immense vitality is underscored by the fact that only approximately seven properties exchange hands each month, with only 31 available currently. Moreover, properties here spend a median of about 19 days listed on the market before being swept up by eager buyers.

Exploring the variety of available homes

Hillsborough offers an array of amazing housing options catering to a broad range of tastes. Whether you're leaning towards a stately historic mansion or a contemporary sprawling estate, you'll find an extensive selection of impressive home designs and architectural styles here. From trophy estates with custom-built designs and expansive lawns to alluring mansions with soaring ceilings, formal entry parlors, and cinema theaters, there is no shortage of luxury and refinement on the Hillsborough real estate scene.

A major benefit to having a local expert is their knowledge of off-market homes.

When a property is listed off-market, this means that their listing is not being listed in the MLS and syndicated to platforms for everyone to see. When you have a local expert that is in tune with the off-market opportunities, this will provide you access to additional inventory that not everyone is privy to.

Defining your priorities

Before embarking on your luxury home journey, take the time to establish your must-haves and want-to-haves. Maybe you’re seeking a grand kitchen oasis, a spacious fenced backyard, a media room, a private terrace, or seven bedrooms. Setting your goals can align your preferences from the get-go and help you narrow down your home search to properties that match your lifestyle and needs.

Financial preparation is key

In any real estate endeavor, it’s essential to be financially prepared before moving forward and committing to a property purchase. Buying a home in Hillsborough will necessitate a substantial initial investment. Of course, the down payment required will depend on various factors, such as the housing price and your mortgage terms.

The value of mortgage pre-approval

If you are financing your home purchase with a mortgage, pre-approval isn't just a formality. It's a powerful tool that can arm you with a realistic understanding of your borrowing capacity and significantly smoothen and streamline your home-buying journey.

Deciding on real estate representation

Navigating the real estate labyrinth is not a task for the uninitiated. Even if your Hillsborough home isn’t your first venture in the real estate game, teaming up with an expert agent is a wise choice if you’re seeking a successful, stress-free transaction.

A professional real estate agent, well-versed in the nuances of the Hillsborough real estate market, homes for sale off market in Hillsborough,  negotiation strategies, and more, can prove invaluable in securing the home of your dreams without a hitch.

Anticipating potential bidding contests

Hillsborough's robust real estate market can often lead to competitive situations, with multiple buyers vying for these stunning properties. For this reason, it's crucial to be prepared for potential bidding wars, especially when considering gorgeous homes in high-demand areas like Hillsborough. Your trusted agent will connect you with outstanding properties and help you devise a strong offer that the seller will be inclined to choose over all the rest.

Partner with the Sternsmith Group to achieve your dreams

For those who appreciate the fusion of sophistication and natural beauty, Hillsborough stands as a timeless sanctuary — an emblem of privilege, elegance, and prosperity. Welcome to a world where luxury knows no bounds, and dreams find their fullest expression amidst the prestigious embrace of Hillsborough real estate, Northern California's crown jewel.

If all this sounds like a dream come true, it’s time to work with a trusted expert who can help you achieve all your real estate aspirations. Offering steadfast commitment to client satisfaction and unmatched success, the experts at the Sternsmith Group dedicate themselves to their client’s goals at every turn. They recognize the deeply personal nature of property transactions and are poised to guide their clients with unwavering support throughout the journey.

Specializing in the luxury market, they have honed their expertise in matching discerning clients with their dream homes. At the Sternsmith Group, the client's needs take center stage, paving the way for a full-service experience that's genuinely personalized and client-focused for on and off-market sales in Hillsborough. As leaders in the San Mateo County real estate landscape, and with over 18 years and $1 billion in successful transactions behind them, these are the professionals you want on your side.

If you're looking to buy or sell a home or have any questions about the Hillsborough real estate market, contact the highly esteemed Realtor®s at the Sternsmith Group today. This seasoned team of professionals is ready to provide you with all the support you need to navigate your real estate journey in Hillsborough effortlessly.

*Header photo courtesy of the Sternsmith Group



Casey Sternsmith

Casey Sternsmith

Founder

Get to Know Me

Meet Casey Sternsmith, founding partner of the Sternsmith Group. In business, exceptional service is what matters most to Casey Sternsmith.

With Casey at the helm of the Sternsmith Group, this level of commitment is shared by all members of the group who pride themselves on being excellent listeners with unwavering integrity, and for providing the best advocacy and negotiation skills for their buyers and sellers.

Casey’s philosophy of “love what you do, or do something else” is at the forefront of the entire team, which is evident by their true passion for helping clients achieve their real estate goals.
 
As a leader in real estate marketing, Casey employs tried and true traditional marketing as well as cutting-edge strategies such as social media marketing and professional videos for every home – from small condos to luxury estate properties. Casey’s clients also benefit from her vast personal network as a lifelong resident of the area.
 
As a result, she often achieves unprecedented outcomes for her sellers with quick sales and prices exceeding the list prices. To her buyers, Casey is known for excelling in competitive multiple-offer situations.
 
With more than 10 years of results that speak for themselves, Casey never looks at the process as a transaction, but rather as a personal decision and life choice that impact each and every day of their life. Because of this, a great deal of Casey’s personal business, and the Sternsmith Group’s as a whole, comes from repeat businesses and referrals.
 
Prior to her career in real estate, Casey owned and operated a personal training/Pilates studio in San Mateo where she honed her customer service, management, organization, and marketing skills. Combined with a bachelor’s degree from UC Santa Barbara, all of this proved to be the ideal foundation for her future success in real estate. Casey and her husband have two small children and reside in Hillsborough.
 
Tess Salter

Tess Salter

REALTOR®

Get to Know Me

Tess Salter is a top-ranked real estate agent in San Mateo County and a key leader of the Sternsmith Group, known for her exceptional negotiation skills, client-first approach, and record of delivering outstanding results. Tess has helped clients buy and sell homes across San Mateo, Burlingame, Hillsborough, Belmont, San Carlos, Redwood Shores, Redwood City, San Bruno, Millbrae, South San Francisco, Bay Meadows, Menlo Park, and Foster City. She specializes in single-family homes, condominiums, townhomes, luxury estates, and investment properties.

With over 10 years of experience, Tess has sold 71 homes in San Mateo County in 2025 and helped 61 buyers and sellers achieve over $125M in sales in 2024, according to RealTrends. Since 2015, Tess and her partner Casey Sternsmith have closed $1.3B+ in total sales, ranking them among the top 5 agents in San Mateo County and the #1 agents in San Mateo for seven consecutive years.

Tess was recognized by Gentry Magazine as one of the Top 10 Agents Under 40 in 2020, and the Sternsmith Group has been nationally recognized on The Leading 100 for the past seven years, celebrating the top-performing real estate teams in the San Francisco Peninsula.

Tess is known for her expertise in off-market listings, pre-market preparation, luxury marketing strategies, and customized property-specific marketing. She leverages Compass’ advanced technology, social media, and Facebook/Instagram Live tours to maximize exposure and deliver top results. With a strong foundation in finance, accounting, and economics, Tess provides data-driven insights that help clients make strategic real estate decisions.

Outside of real estate, Tess is deeply committed to her community. She served as PARCA Auxiliary President (2024–2025), continues on the PARCA Board (2019–2025), volunteers in Hillsborough schools, served on the West Elementary School Site Council, and chairs the Relay for Life for the American Cancer Society.

With 150+ five-star reviews and a reputation for integrity, responsiveness, and personalized service, Tess Salter and the Sternsmith Group provide exceptional guidance, strategic marketing, and unparalleled support for anyone buying or selling in San Mateo County, Burlingame, Hillsborough, and surrounding Peninsula neighborhoods.

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Insightful local knowledge and extensive expertise. We looks forward to earning your family’s trust and leveraging our success for your benefit for generations to come. We looks forward to earning your family’s trust and leveraging our success for your benefit for generations to come.

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