- Agent Pronto
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- Winchester
Find the perfect real estate agent in Winchester, San Jose, CA
We analyze top real estate agents in San Jose’s Winchester neighborhood and across the country to find you the most proven local agents, for free.
Compare the top 25 real estate agents in Winchester
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for May 2025. *
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
The easiest way to find the best real estate agent.
Sell your home fast and for top dollar or find your dream home at the best possible price. Use our free service to find top agents you can trust.
- Tell us what you need.
- Answer a few quick questions about your real estate needs so we can begin our search.
- Match with the perfect agent.
- Our personalized matching system will connect you with a top-rated real estate agent with the local expertise and experience you need.
- Meet your agent.
- Review the details of your top agent recommendations and speak with them to learn exactly how they can make your real estate journey a success.
- Buy and sell with confidence.
- While real estate decisions are among the most important financial and personal decisions we make, you can rest easy knowing that you have a proven real estate professional on your side.
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.
“It was a pleasure to deal with Louis in regards to the sale of my property.”
“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.”
“Connected me with a very good, knowledgeable agent, which made the whole experience very satisfying. Would definitely recommend.”
“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.”
“Jess Williams was very professional and did a fine job.”
“You recommended 2 agents, both of whom contacted me but Tyron did so within a few hours and we hit it off and he got the job. Thank you for the excellent recommendation!”
“When it was time for my elderly parent to sell her home I had no idea how to select an agent to represent her. Agent Pronto selected two agents to talk to who were familiar with her location. They both responded to me quickly and gave me great advice!”
“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.”
“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.”
“He was excellent!!!”
Winchester real estate Market Report.
Information and statistics on the latest trends in the Winchester real estate market, updated for May 2025. *
The typical home value in Winchester is projected to be $1,764,120 for the month of April. March’s finalized data reported the typical value of a home in the neighborhood to be $1,650,000—up 2.36% 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 $1,501,750 in April.
Winchester had 58 new listings and 39 listings that went under contract in March, increasing the area’s total available inventory to 28—up 40.0% from the previous month. Inventory is projected to have further increased in April.
The median listing price for homes in Winchester fell 10.39% from February to March, bringing the current median listing price to $1,509,860. Based on projected data for April, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract has been fairly steady year-over-year. In March 2025, the median time for a listed property to go pending was 13 days, compared to 15 days in March 2024. However, in recent months the median number of days from listed to pending appears to be rising. That trend is predicted to have carried through to this April.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Learn more about what Winchester has to offer.
Winchester offers residents a vibrant community enriched with beautiful parks, top-rated schools, and convenient access to shopping and entertainment options.
Winchester draws a lively mix of energy from its position in western San Jose, offering a seamless blend of urban accessibility and comfortable suburban living. Life here revolves around discovery, with the iconic Winchester Mystery House serving as both a neighborhood landmark and a gateway to fascinating local lore. Food lovers find themselves just minutes from Santa Row, an upscale shopping and dining corridor perfect for everything from relaxed brunches to celebratory dinners, while the Westfield Valley Fair mall expands shopping options even further.
Families in Winchester appreciate access to both public and private educational opportunities. Monroe Middle School draws students from the community, while several nearby elementary schools, like Lynhaven Elementary School, help anchor a strong foundation for young learners. Numerous parks, including Starbird Park, offer ample space for kids to play, while the Bascom Community Center provides classes, fitness programs, and year-round activities.
Bordered by convenient thoroughfares and close to both Santa Clara and Campbell, Winchester is perfect for commuters and those who crave quick access to major employment centers and destinations throughout Santa Clara County. Whether you're drawn by the storied past of the Winchester Mystery House, outstanding public amenities, or the sheer variety of shopping and dining, Winchester offers a welcoming environment for newcomers and longtime residents alike. If you're looking to find your ideal home—or hoping to connect with the right buyer—Agent Pronto makes it easy to link up with a knowledgeable local real estate agent who understands the Winchester neighborhood from every angle.
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!
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 Winchester 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!
Resources for buyers and sellers.
Tips and market insights to make your San Jose real estate journey a success.
Frequently Asked Questions
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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.
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Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
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We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
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No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents.
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