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 $1,395,000 for the month of August. July’s finalized data reported the typical value of a home in the city to be $1,430,000—up 8.64% over the previous 12 months. For comparison, county-level data pegged home values at $860,000 in Middlesex County for the most recent reporting period. That number is expected to float around $855,870 in August.
Winchester had 27 new listings and 25 listings that went under contract in July, decreasing the area’s total available inventory to 46—down 13.21% from the previous month. Inventory is projected to have further decreased in August.
Of those 46 active listings, 28.26% reduced their price in the month of July. The median listing price for homes in Winchester fell 9.75% from June to July, bringing the current median listing price to $1,500,000. Based on projected data for August, 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 July 2025, the median time for a listed property to go pending was 18 days, compared to 18 days in July 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 August.
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 blends classic New England streetscapes with everyday convenience, set just a quick commute from Boston and within Middlesex County. A walkable town center hums with cafés, boutiques, and a year-round community calendar stewarded by the Town of Winchester. Weekends often revolve around the Mystic Lakes, tree-lined neighborhoods, and convivial gatherings at the commons.
Families are drawn to the excellence of Winchester Public Schools, consistently recognized for strong academics, arts, and athletics. The town’s commitment to lifelong learning extends beyond the classroom, from story hours at the library to workshops and talks at the Griffin Museum of Photography, a nationally respected hub for the visual arts. Healthcare needs are anchored close to home by Winchester Hospital, offering comprehensive services with the personal feel residents value.
Outdoor lovers make the most of the nearby Middlesex Fells Reservation, where miles of trails invite hiking, biking, and winter walks. Seasonal rhythms feel especially alive at Wright-Locke Farm, a beloved working farm and historic landscape hosting markets, classes, and family-friendly events that connect neighbors to nature and local food.
Whether you picture a classic Colonial, a renovated Victorian, or a modern in-town condo, Winchester offers options that pair small-scale living with big-city access. If you’re considering buying or selling here, Agent Pronto simplifies the process by matching you with a proven local real estate professional who knows Winchester’s streets, schools, and market inside and out.
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.
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!
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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