“Nancy is professional, easy to communicate with, responsive to calls and text. She is a very experienced realtor who knows the market well and has many useful contacts for new home owners. I highly recommend her and for Fudge reators.”

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Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for August 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.
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Information and statistics on the latest trends in the Winchester real estate market, updated for August 2025. *
The typical home value in Winchester is projected to be $1,357,500 for the month of July. June’s finalized data reported the typical value of a home in the city to be $1,500,000—up 5.26% over the previous 12 months. For comparison, county-level data pegged home values at $869,500 in Middlesex County for the most recent reporting period. That number is expected to float around $874,250 in July.
Winchester had 32 new listings and 30 listings that went under contract in June, decreasing the area’s total available inventory to 52—down 0.0% from the previous month. Inventory is projected to have further decreased in July.
Of those 52 active listings, 32.69% reduced their price in the month of June. The median listing price for homes in Winchester grew 14.7% from May to June, bringing the current median listing price to $1,662,000. Based on projected data for July, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract has been fairly steady year-over-year. In June 2025, the median time for a listed property to go pending was 18 days, compared to 18 days in June 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 July.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Winchester offers residents a charming blend of historic charm, excellent educational opportunities, and a vibrant community atmosphere that fosters a high quality of life.
Winchester invites residents to enjoy a vibrant blend of scenic elegance, top-tier academics, and a true sense of community just a quick train ride from the Boston city bustle. Majestic Victorian and Colonial homes line leafy streets, accenting the town’s blend of historic character and modern sophistication. Families are drawn to Winchester for its acclaimed Winchester Public Schools, including Vinson-Owen Elementary and Winchester High School, both known for academic excellence and an outstanding network of support programs.
Local life flourishes around Winchester Center, where bustling cafes, trendy boutiques, and an old-fashioned movie house foster a welcoming small-town atmosphere. The peaceful Mystic Lakes draw joggers, kayakers, and picnickers, while the nearby Middlesex Fells Reservation entices hikers and nature lovers to its forested trails. For history enthusiasts, the Griffin Museum of Photography and Winchester Public Library provide a window into the town’s artistic and cultural vibrancy.
Easy access to Medford and Lexington broadens your world with even more dining, shopping, and historical exploration, all while you return home to the calm of your friendly neighborhood. Whether you’re looking to put down roots or considering selling your home, Agent Pronto is here to make your Winchester transition smooth and successful by connecting you with the best local real estate professionals.
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!
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.
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Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Winchester. But we don’t stop there.
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Tips and market insights to make your Winchester real estate journey a success.
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.
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.
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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