Find the perfect real estate agent in Cherrywood, San Jose, CA

We analyze top real estate agents in San Jose’s Cherrywood neighborhood and across the country to find you the most proven local agents, for free.

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Real estate in San Jose’s Cherrywood neighborhood.

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Home buyers and sellers love Agent Pronto.

Here’s what some of the 400,000+ home buyers and sellers have had to say about our service.

“We couldn't have had a better realtor. With Geoff's experience, he was able to explain the process and the why's. Any realtor can help you when everything is smooth sailing, but when our sale started getting bumpy, Geoff was there always explaining options, ultimately leaving the decisions to us. He was definitely in our corner and earned our respect.”
5 stars
JP
Julie P.
San Jose, CA
“It was a pleasure to deal with Louis in regards to the sale of my property.”
5 stars
SL
Svein L.
San Jose, CA
“Connected me with a very good, knowledgeable agent, which made the whole experience very satisfying. Would definitely recommend.”
5 stars
MH
Mark H.
Morgan Hill, CA
“Thank you for quickly responding with a very good agent at the top of your list for my area. I am using Jameson to manage my newly acquired property. He did a great job finding the property I finally bought!”
5 stars
MM
Madeleine M.
Bakersfield, CA
“The house sold 4 days after it went on the market, and for $10,000 over list price. Nothing more could be said. Great recommendation.”
5 stars
JM
Jerry M.
Riverside, CA
“We had Matthew Welch as our realtor and he was so easy to work with. What I appreciated most was the consistent open communication. He was available to us at all hours and assisted with anything we had questions about. Matt has a very positive outlook and reassured us that our perfect home was out there. He was right. He worked hard for us and worked to give us the best chance of getting the house we really wanted.”
5 stars
MR
Mahcon R.
Long Beach, CA
“It was fast and easy!”
5 stars
JG
Joel G.
Fresno, CA
“Agent Pronto was great! They connected me with an awesome agent who was with me every step of the way. My agent provided information at each intersection of my purchase! Even with a few bumps in the road, Sheila Green kept me informed.”
5 stars
DR
Daniel R.
Sacramento, CA
“Jess Williams was very professional and did a fine job.”
5 stars
WP
William P.
San Francisco, CA
“All was A+ and Kelli was very knowledgeable. She said a fast sale, and that it was...I would use Kelli again!”
5 stars
LS
Linda S.
Sacramento, CA

Cherrywood real estate Market Report.

Information and statistics on the latest trends in the Cherrywood real estate market, updated for June 2025. *

The typical home value in Cherrywood is projected to be $1,410,000 for the month of May. April’s finalized data reported the typical value of a home in the neighborhood to be $1,410,000—down 25.55% over the previous 12 months. For comparison, city-level data pegged home values at $1,480,000 in San Jose for the most recent reporting period. That number is expected to float around $1,480,000 in May.

Cherrywood had 8 new listings and 5 listings that went under contract in April, increasing the area’s total available inventory to 3—up 200.0% from the previous month. Inventory is projected to have further increased in May.

The median listing price for homes in Cherrywood grew 4.5% from March to April, bringing the current median listing price to $1,462,000. Based on projected data for May, listing prices may continue to grow.

The number of days that homes have been on the market prior to going under contract rose year-over-year. In April 2025, the median time for a listed property to go pending was 8 days, compared to -1 days in April 2024. In recent months the median number of days from listed to pending appears to be steady. That trend is predicted to have carried through to this May.

Real estate in San Jose’s Cherrywood neighborhood.
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Seller’s Market
Seller’s Market
Buyer’s Market
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25
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75
100

Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.

* Data provided by Redfin, a national real estate brokerage.

Learn more about what Cherrywood has to offer.

Cherrywood offers residents a vibrant community atmosphere with convenient access to parks, local amenities, and diverse dining options, making it a welcoming place to call home.

Cherrywood offers an inviting living experience in the northern reaches of San Jose, seamlessly blending accessibility with a welcoming residential character. Residents are drawn to this area for its well-maintained homes, mature tree-lined streets, and its advantageous location—just moments from major corridors such as I-880 and Montague Expressway, connecting you swiftly to tech hubs and nearby destinations like Santa Clara. Cherrywood stands out for its ease of access to Bay Area amenities while retaining a sense of community prized by families and professionals alike.

Education plays a central role in daily life, with Cherrywood Elementary and Adrian Wilcox High, both part of the Santa Clara Unified School District, providing reputable academic programs and a diverse range of extracurriculars. For outdoor relaxation, Townsend Park invites locals to unwind with walking paths and playgrounds, while nearby Cataldi Park offers additional recreation options for all ages.

Shopping and dining are minutes away, thanks to destinations like the Great Mall and an array of local eateries that reflect the vibrant culinary scene of Silicon Valley. Cherrywood’s proximity to the Levi’s Stadium means that world-class entertainment and sports events are always within reach. Additionally, well-established public transit via the Santa Clara Valley Transportation Authority opens up robust commuting possibilities.

Whether you are buying or selling, Cherrywood’s unique blend of convenience and comfort makes it an attractive choice. With Agent Pronto, both buyers and sellers can be matched with top real estate professionals to make the most of their Cherrywood experience.

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Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!

Sarah W.

Take the guesswork out of finding an agent.

With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.

We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Cherrywood to qualify the best agents for your specific needs.

We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.

Data analysis with a human touch.

Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in San Jose. But we don’t stop there.

Our Agent Specialists will take into account any special requests you have when searching for your real estate agent recommendation.

Need a great agent who speaks fluent Spanish and is a luxury condo expert in your neighborhood? No problem!


Frequently Asked Questions

There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.