“Brad was wonderful to work with. He was very patient with us on trying to find our forever home. I would recommend him to anyone who wants someone who listens to you.”
Century 21 Wright Realty
- Agent Pronto
- Tennessee
- Winchester
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Compare top Winchester real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for August 2026.*
* 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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Winchester real estate Market Report.
Information and statistics on the latest trends in the Winchester real estate market. *
Latest Rolling 3-Month Snapshot
May 1, 2026 - Jul 31, 2026
Median sale price
$386K
+11%
from
Q2 '26
Median list price
$376K
-8%
from
Q2 '26
Active listings
200
-3.8%
from
Q2 '26
Homes sold
72
+2.9%
from
Q2 '26
New pendings
65
-3%
from
Q2 '26
New listings
88
-5.4%
from
Q2 '26
Quarterly Pricing Trends for Winchester
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Winchester
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Winchester
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Winchester
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Winchester
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Winchester
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
31
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (May 2026 - Jul 2026).
Inventory in Winchester has expanded in this rolling three-month view, with active listings up more than 30% year over year and around 200 homes now on the market. At the same time, closings and contract activity have picked up, as homes sold have climbed by roughly two-thirds and pending sales are up more than 50% from a year ago.
Pricing has been adjusting alongside this stronger flow, with the typical home value up nearly 30% year over year even as the median list price is slightly lower than a year ago. Sellers are seeing an average sale-to-list ratio around 96%, and only a small share of homes are closing above asking, suggesting buyers have somewhat more room to negotiate than in past peak periods.
Time on market has lengthened notably, with the median days on market now into triple digits in this latest three-month window, yet months of supply has fallen compared with last year, keeping Winchester in seller’s market territory. With new listings up close to 30% from a year ago but homes no longer flying off the market immediately, local conditions can feel very different depending on a property’s price point and presentation. Buyers and sellers who want to navigate these mixed signals can turn to Agent Pronto to connect with a Winchester real estate agent who understands the latest trends.
Learn more about what Winchester has to offer.
Winchester offers residents a warm, close-knit community with easy access to parks, schools, local shops, and a steady calendar of events that make everyday life engaging and comfortable.
Winchester sits at the heart of Franklin County, offering small city convenience with easy access to Tims Ford Lake and larger hubs like Chattanooga and Huntsville. Daily life revolves around practical amenities, from local schools and health care to shopping and services that keep errands straightforward.
Residents appreciate the walkable historic square, anchored by the Oldham Theater and local restaurants that make a night out simple and close to home. Outdoor enthusiasts value the marinas, boat ramps, and trails around Winchester City Park, plus quick trips to Twin Creeks Marina for waterfront dining and recreation. The Franklin County School District and local libraries provide education and enrichment that matter to families planning for the long term.
Commuters find straightforward routes along US‑41A and nearby highways, while local events like festivals around the square add a sense of community without sacrificing quiet neighborhoods and lakefront retreats. From established in‑town homes to newer developments closer to the water, Winchester offers a range of housing that fits different budgets and stages of life.
Navigating these options, understanding upcoming developments, and pricing accurately can be complex. Agent Pronto connects you with Winchester agents who know the market, easing the stress for both buyers and sellers so you can focus on the move instead of the hassle.
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“Katelyn went above and beyond to keep us informed and engaged in the selling process. She provided helpful insight and guidance without ever pushing -- always leaving the decision in our hands. We look forward to working with Katelyn again when our next property is ready to list.”
Castle & Associates Real Estate
“This was the third time dealing with David Edwards and I will always work with David should the opportunity arise again! He is honest and professional and I trust him completely!”
CENTURY 21 Legacy
“Mike was an excellent agent to work with. He went above and beyond to find out all the information on the property details and answers to all questions we had. He was available anytime we needed. We would recommend him to anyone interested in purchasing or selling a home. He is the best!!”
Century 21 Legacy
“Shawn was wonderful to work with. He was super helpful in getting us in contact with local services to work on our home. I would definitely recommend his business to others.”
Century 21 Wright Realty
“Jeremiah was an absolute pleasure to work with! We have never had an agent as informed and quick to respond as he was. We're not unfamiliar with the home buying process, but Jeremiah was still able to explain any questions we had and work with us through difficult and unique circumstances. We absolutely love the house we got, but if we ever consider a different one down the line, Jeremiah will be the first person we reach out to. And I will recommend anyone looking for houses in the area to do the same.”
Epique Realty
“Brooke was amazing!! She truly went above and beyond to help me find a house to call home. I truly could not be more thankful I got to work with her!!!”
Century 21 Legacy
“Tracey is the best realtor. She makes stressful negotiations a breeze from start to finish. She is professional but adds her personal touch to all communications and transactions to make you feel like family. I have used Tracey for over 10 years in buying and selling several homes. I would never use another realtor in buying or selling my home.”
RE/MAX Real Estate Ten Midtown
“Misty was an absolute pleasure to work with! She went above and beyond in the entire home buying process. Misty went out of her way to meet with us to view several potential properties on short notice. Her insight and knowledge were critical in informing my decisions. She walked me through the tough negotiations so I could navigate them confidently. Myself and my family are truly thankful for her help in finding our home!”
Century 21 Platinum Properties
“I contacted Pronto because we needed to sell a deceased relative's home in Tennessee, while we live in Ohio. Agent Pronto put us in touch with two agents, and we chose Amber Vittetoe who was nothing short of fabulous. She provided us with many resources that we wouldn't have known about since we're not local, and she was extremely responsive 24/7. We couldn't have asked for a better agent. Thank you!”
MG Rise Realty
“Khristian was extremely helpful in buying my home. I truly felt at home and at ease working with him. He made sure I was aware of everything going on, and took me to every home I wanted to see.”
Keller Williams First Class Real Estate
“Jessica is an amazing Realtor. She truly cares about the people she works with and goes above and beyond to make her clients transition a smooth one. We just loved working with her and will definitely work with her again. She is great for vacation homes too both in the Smokies and Panama City Beach FL. Her knowledge of short term rentals helped us tremendously.”
Realty One Group Emerald Coast
“Mr. Black made it so for us.”
Century 21 Platinum Properties
“Good service nice response time very polite overall very satisfied stay dangerous Betty lol”
eXp Realty
“She helped us buy our house, then sell it a few years later. Couldn't recommend more! So communicative, answered all my questions at a timely, proffessional manner. I was probably not the easiest client at times because stress, but she was so calm and reassuring through the whole process! Seriously so grateful for how smoothly this sale went, all with the help of Marie!”
CENTURY 21 Platinum Properties
“Rolanda was absolutely wonderful to work with during the selling process. She was professional, knowledgeable, resourceful, and patient. She ensured that I was represented well and every step of the way. I highly recommend Rolanda to friends, family, or associates.”
Coldwell Banker Pryor Realty
“Ms. Kimberly Townsend is an awesome realtor! She assisted us in finding our forever home with all our wants. She went over and beyond to make sure all of our needs were met. We truly appreciate her due diligence to property details that buyers would not have notice. She is very knowledgeable and professional. She explained every step of the home buying process in depth. She made this experience enjoyable! Excellent Job, Ms. Townsend.”
Century 21 Patterson & Associates
“Miss Candy was very helpful with the sale of the property she knew what she was doing and how to handle all things that needed to be handled. I would recommend her to anyone that needed help with the sell of their property and I will use her again if I need help with selling any property, Thank you so much Miss Candy for helping in the sale of the property.”
Keller Williams Realty
“Matthew demonstrated excellent realtor service. From communicating, providing assistance and more, this is tge type of serivice you would look for an a realtor!”
EXP Realty
“Ruby Alexander is excellent at everything she does. She previously helped us purchase our home. Ruby is professional, knowledgeable, honest, hard-working, friendly, intuitive, and resourceful. She goes above and beyond the call of duty. We would not have wanted to take the journey of buying or selling our home with anyone else.”
CENTURY 21 Legacy
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 covering the housing market in and around Winchester. 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. Find your Winchester Realtor® or real estate agent today.
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