We analyze top real estate agents in Winchester and across the country to find you the best veteran and military-friendly local agents, for free.
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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“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.”
“Len went above and beyond during the whole process of selling my mother's home. He was kind, considerate, compassionate and extremely helpful, during an especially stressful time. I would definitely recommend him without hesitation.”
“El seńor Juan lopera,excelente agente vendedor respetuoso al entrar a la propiedad igual que su equipo de trabajo ,muy buena comunicación,siempre pendiente durante todo el proceso de venta. Gracias.”
“Topnotch service! Grateful that I found him and highly recommend him for any real estate transaction you need help with. Would use him again in a heartbeat. He and his team made selling our family home so much easier than we ever expected. Thank you, Craig Celli!”
“I'd strongly recommend Jill! We felt like we were in good hands every step of the way”
“Rosa stepped in when we were not getting anywhere in finding a suits property. Within 72 hours Rosa had several viewings booked and we had 2 offers in place. Ultimately she brokered a great deal on the perfect place to purchase. She continued to work with us throughout the process and closing. She even helped communicate with the previous agents when we needed something fixing. She is an excellent agent and great ambassador for Real Satisfied.”
“Thank you and great job!!”
“Great real estate experience with Charlotte. I recently had the pleasure of working with Charlotte as my realtor, and I cannot express how grateful I am for her outstanding service throughout the entire home buying process. From our initial meeting to the closing day, Charlotte demonstrated a level of professionalism, expertise, and dedication that greatly met my expectations. One of Charlotte's standout qualities is her extensive knowledge of the local real estate market. She took the time to understand my preferences and priorities, providing valuable insights into neighborhoods, property values, and future market trends. Her expertise not only streamlined the decision-making process but also ensured that I made informed choices.”
“Shawn and Dee were amazing. They made the process very easy and were always available for questions or guidance.”
“I can't thank John Dean enough for handing the sale of my home. John's knowledge of the industry and the area was exceptional. He kept me informed of all the issues and guided me with decisions that had to be made. He offered to make several trips to the house to meet and coordinate the inspections and other people that assisted me with the move. Not being available to make it to the property for various reasons being the distance and caring for a disabled husband, John saved me from having to be there. John was there to manage everything for me. If you need a professional agent, look no further than John Dean.”
“He was honest enough to direct us away from one of the homes that we looked at because of the horrible basement there. He also showed us at least 5+ homes before we settled on the one we're living in now.”
“We can't say enough good things about our experience with Sarah. Throughout the buying process, we always felt that she understood our needs and put our best interest first. She was professional yet completely approachable, and she has given us many tips about our new neighborhood and the surrounding area. We would highly recommend Sarah to anyone looking to purchase a home in the Boston area.”
“Smita was brilliant and the best we could have hoped for - she was a dream to work with. I am very happy with her patience with me as a first time home buyer and she continues to support me post purchase. Smita came very strongly recommended from a trusted source, and we will recommend her to all our friends. Her knowledge of the Shrewsbury market is commendable - in fact all her predictions came true. She was perfect except only one thing - we personally think she could have helped better with the negotiation of another property (141 Worthington). But having said that, she landed us probably a better property.”
“Elena is one of a kind just like how she found my perfect home for me in West Boylston, Massachusetts. I am from San Diego, California and never would have imagined to own a home in central Massachusetts but she opened my eyes to a beautiful town of West Boylston and provided great statistical feedback to help me make my decision. I am happy with my decision and a lot of it comes from a skilled and professional agent such as Elena. Highly recommend her.”
“I had been referred to Marc by a family friend. I could not have been happier. He was incredibly accommodating, understanding, patient and most importantly transparent throughout the process of the sale. I felt very reassured having him represent me through this whole process.”
“The whole team involved was wonderful. Thank you all.”
“Chris Cassidy comes across as a very honest, and approachable person. Chris was involve in selling a 2 family for me , which was caught up in the Columbia Gas crisis which occurred shortly after he listed it. The Columbia gas problem affect homes in a huge area.The property for a few months was essential not able to be sold because of the Columbia Gas issue. During this time Chris did his best to show, and the sell the property. Eventual after Columbia Gas finally fixed all the gas lines that were affected Chris was then able to find the buyer for this property. Took months, but Chris never gave up, or showed any disinterest. I plan to work with him in the near future.”
“We were matched up with Greg Maund who was an incredible broker and help us get the apartment of our dreams. ”
“We researched top brokers on line, then invited 3 to visit us at the home, prior to selection. Karen was professional, thorough, and friendly, as well as well prepared. Karen was incredible throughout the process. She actually sold the house twice, after the first buyers pulled out at the last minute. She had the house sold again in less than a week! A complete professional and great to work with. Couldn’t recommend her more strongly. Always available, and always on top of the situation.”
“It was great working with Sam Renuka , do you help my brother and sister find their dream home,and as time passes me and my wife decided to look for a place of our own so we decided to call Sam up and after five years he still remembers me and my family,there's a lot of stress and buy your house and he made the experience more enjoyable definitely recommend him,The seller agent was very please with him to.”
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.
We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.
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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