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Winchester, KY real estate

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 June 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

Feb 1, 2026 - Apr 30, 2026

Median sale price
$235K
-9.7% from Q1 '26
Median list price
$248K
+1.3% from Q1 '26
Active listings
143
+25% from Q1 '26
Homes sold
44
+13% from Q1 '26
New pendings
74
+40% from Q1 '26
New listings
85
+57% from Q1 '26

Quarterly Pricing Trends for Winchester

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Winchester Q2 '21 Q2 '22 Q2 '23 Q2 '24 Q2 '25 Q1 '26 Median sale price in Apr 2021 - Jun 2021: $180K Median sale price in Jul 2021 - Sep 2021: $161K Median sale price in Oct 2021 - Dec 2021: $186K Median sale price in Jan 2022 - Mar 2022: $174K Median sale price in Apr 2022 - Jun 2022: $191K Median sale price in Jul 2022 - Sep 2022: $217K Median sale price in Oct 2022 - Dec 2022: $196K Median sale price in Jan 2023 - Mar 2023: $230K Median sale price in Apr 2023 - Jun 2023: $178K Median sale price in Jul 2023 - Sep 2023: $203K Median sale price in Oct 2023 - Dec 2023: $234K Median sale price in Jan 2024 - Mar 2024: $211K Median sale price in Apr 2024 - Jun 2024: $235K Median sale price in Jul 2024 - Sep 2024: $240K Median sale price in Oct 2024 - Dec 2024: $207K Median sale price in Jan 2025 - Mar 2025: $181K Median sale price in Apr 2025 - Jun 2025: $223K Median sale price in Jul 2025 - Sep 2025: $260K Median sale price in Oct 2025 - Dec 2025: $267K Median sale price in Jan 2026 - Mar 2026: $260K Median list price in Apr 2021 - Jun 2021: $175K Median list price in Jul 2021 - Sep 2021: $175K Median list price in Oct 2021 - Dec 2021: $190K Median list price in Jan 2022 - Mar 2022: $175K Median list price in Apr 2022 - Jun 2022: $217K Median list price in Jul 2022 - Sep 2022: $185K Median list price in Oct 2022 - Dec 2022: $221K Median list price in Jan 2023 - Mar 2023: $230K Median list price in Apr 2023 - Jun 2023: $215K Median list price in Jul 2023 - Sep 2023: $235K Median list price in Oct 2023 - Dec 2023: $214K Median list price in Jan 2024 - Mar 2024: $217K Median list price in Apr 2024 - Jun 2024: $240K Median list price in Jul 2024 - Sep 2024: $250K Median list price in Oct 2024 - Dec 2024: $192K Median list price in Jan 2025 - Mar 2025: $230K Median list price in Apr 2025 - Jun 2025: $240K Median list price in Jul 2025 - Sep 2025: $275K Median list price in Oct 2025 - Dec 2025: $248K Median list price in Jan 2026 - Mar 2026: $245K Apr 2021 - Jun 2021 Median sale price $180K Median list price $175K Jul 2021 - Sep 2021 Median sale price $161K Median list price $175K Oct 2021 - Dec 2021 Median sale price $186K Median list price $190K Jan 2022 - Mar 2022 Median sale price $174K Median list price $175K Apr 2022 - Jun 2022 Median sale price $191K Median list price $217K Jul 2022 - Sep 2022 Median sale price $217K Median list price $185K Oct 2022 - Dec 2022 Median sale price $196K Median list price $221K Jan 2023 - Mar 2023 Median sale price $230K Median list price $230K Apr 2023 - Jun 2023 Median sale price $178K Median list price $215K Jul 2023 - Sep 2023 Median sale price $203K Median list price $235K Oct 2023 - Dec 2023 Median sale price $234K Median list price $214K Jan 2024 - Mar 2024 Median sale price $211K Median list price $217K Apr 2024 - Jun 2024 Median sale price $235K Median list price $240K Jul 2024 - Sep 2024 Median sale price $240K Median list price $250K Oct 2024 - Dec 2024 Median sale price $207K Median list price $192K Jan 2025 - Mar 2025 Median sale price $181K Median list price $230K Apr 2025 - Jun 2025 Median sale price $223K Median list price $240K Jul 2025 - Sep 2025 Median sale price $260K Median list price $275K Oct 2025 - Dec 2025 Median sale price $267K Median list price $248K Jan 2026 - Mar 2026 Median sale price $260K Median list price $245K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
19
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Feb 2026 - Apr 2026).

Year over year, Winchester’s rolling three-month data shows notable price growth even with some recent softening. The typical home value is up about a quarter from last year, while the current median sale price sits around $234,879 with list prices near $248,036.

Inventory conditions have shifted meaningfully compared with a year ago. Months of supply has climbed to about 5.3, up sharply from early 2025 levels, even though active listings are roughly flat year over year at 143.

Buyer activity looks mixed in this period, with homes sold down more than 25 percent from a year ago while pending sales are also lower than last year. At the same time, nearly half of homes still go off the market within two weeks and the average sale-to-list price ratio is just over 98 percent, so both buyers and sellers can benefit from an Agent Pronto–recommended agent to navigate these conditions effectively.



Learn more about what Winchester has to offer.

Winchester offers residents a friendly, family-oriented community with a historic downtown, abundant parks and outdoor recreation, affordable living, and convenient access to regional amenities.

Winchester offers small city convenience with quick access to Lexington and the I‑64 corridor, making daily commuting and regional travel straightforward. Residents appreciate its manageable traffic, established neighborhoods, and a downtown that blends historic character with practical services and dining.

Life here centers on accessible amenities. Historic Main Street features local shops and restaurants like Loma’s at the Opera House, along with seasonal events that bring neighbors together. Families are served by Clark County Public Schools, including George Rogers Clark High School, while the Clark County Public Library offers programs for all ages, remote workers, and students. Everyday errands are easy thanks to grocery options, medical offices, and services clustered along the bypass.

Outdoor recreation is a major draw. The Legacy Grove Park trail system, Lykins Park, and the Winchester-Clark County Parks & Recreation center support an active lifestyle close to home. Nearby natural destinations such as Red River Gorge are an easy day trip. Local government resources, including City of Winchester and Clark County, help residents stay informed about services and infrastructure. For a broader picture of the region, explore Lexington, Clark County, Fayette County, and Richmond.

Whether you are relocating across town or from out of state, a knowledgeable local agent can clarify neighborhoods, commutes, and price trends. Agent Pronto connects buyers and sellers with experienced Winchester professionals who help streamline decisions and reduce stress at every step.

Find your Winchester real estate agent today →


Trusted by over 500,000 buyers and sellers.

See why so many people rely on Agent Pronto to make their real estate journey a success.

“Marsha was wonderful to work with! I could text her with any questions and she was always so quick to respond and so helpful! Definitely would work with her again.”

Sarah Gourley · Paducah, KY

Photo of Marsha Bartlett
eXp Realty LLC Kentucky
“I could not have gotten better care. he sold my home during the WAR. I think that is outstanding”

Cindy Trimble · Campbellsville, KY

Photo of David Hittle
United Real Estate Louisville
“Working with Derrick was an outstanding experience from start to finish. He and his team helped get our property completely ready for market by coordinating repairs, cleanup, and improvements that made a huge difference in how the home showed. His team worked tirelessly and brought a tremendous amount of knowledge and experience to the project, making the entire process smooth and efficient. Derrick’s understanding of what buyers are looking for and what actually adds value was incredibly helpful. Once the property was ready, he handled the listing and marketing process seamlessly, and the home sold quickly. What could have been a stressful situation became simple and organized thanks to Derrick and his team. I would absolutely recommend him to anyone looking to prepare and sell a property.”

Robert · Richmond, KY

Photo of Derrick Simpson
Century 21 Advantage Realty
“I am writing to express my sincere appreciation for the outstanding service provided by Scarlett throughout my recent real estate transaction. From our initial consultation to the final closing,Scarlett demonstrated exceptional professionalism, market expertise, and dedication. Her attention to detail, clear communication, and commitment to ensuring a smooth process made what can often be a stressful experience remarkably seamless. Scarlett consistently went above and beyond expectations — promptly addressing every question, providing thoughtful guidance, and negotiating with great skill and integrity. Her deep understanding of the market, strategic approach, and genuine concern for my best interests were evident at every stage.”

Ranjita Mishra · Union, KY

Photo of Scarlett  Sackmann
Berkshire Hathaway Home Services Professional 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!”

Kristen Curtis · Clarksville, TN

Photo of Marie LaVoise
CENTURY 21 Platinum Properties
“We loved our realtor! April Meredith is outstanding to work with she went above and beyond to help us find our forever retirement home.”

Dawn B. · Caneyville, KY

Photo of April Meredith
ERA Real Estate Schuler Bauer Real Estate Services
“James Martin understood what we wanted and needed. He worked with our schedules so we could look at houses and helped us pick the perfect house for us.”

Mr and Mrs Ortega · Owingsville, KY

Photo of James Martin
Realty World Adams & Associates
“Joseph was right there for us when we contacted for an agent. He was open and honest with us on everything Joseph didn't stop looking for places even when we couldn't go until after 430. We both felt comfortable talking to him over all our expenses and what we needed Joseph forums us the perfect house and we would definitely use him again if needed and would recommend him to other people. Thanks from both Lee and I for helping us find our perfect new home. Connie and Lee”

Connie Heisler · Florence, KY

Photo of Joe  Lockaby
ERA Real Estate ERA REAL SOLUTIONS REALTY
“Jason was awesome to work with! Very professional and knowledgeable about the area. He was always willing to answer any questions we had, especially since we were first time sellers. Would recommend to anyone!”

Ivan Adame · Lexington, KY

Photo of Jason Hayes
Rector Hayden Realtors
“Joe is a highly experienced realtor and has excellent people skills. He listens and responds appropriately. He is respectful and friendly. Most importantly he is an expert and most knowledgable in his profession. He navigated through both the sale and purchase processes, answering and addressing all of our questions and concerns. And, in my opinion, his best feature of all is.... he is a really nice person! I am glad to know him, and we were fortunate to have him guide us through our journey.”

John Nackhla · Maineville, OH

Photo of Joe Weiner
Coldwell Banker Realty
“Chris went above and beyond to help me, my mother, and the sale of the home . He was in constant communication and we had a great experience with him ”

Keith H. · Booneville, KY

Photo of Chris Riggsby
Dream Maker Realty
“Natasha Bintz is an amazing person and a great realtor. We would highly recommend her to anyone wishing to sell their house in Kentucky. She went above and beyond to help us when we needed to sell quickly and was sweet about it the whole time. Thank you, Natasha!”

Joshua B. · Covington, KY

Photo of Natasha  Bintz
Keller Williams realty service
“Mary was great and pleasant to work with and I would recommend her to anyone!”

Charles H. · Lebanon Junction, KY

Photo of Mary Ashburn
Re/Max Clinkenbeard
“Erin is very good at what she does. She knows the market values, the area, she is very personable and easy to work with. Her achievements were important in our decision to use Eric. I would and have recommended her to other people that have mentioned about they were thinking of buying or selling. We know several realater but we didn't want to use someone we knew, I'm glad we made that decision or we would not have meet Eric, we are very satisfied with the sale of our parents house. Eric is a great sales person and a great person, and great to work with!! You have a great Sales Lady !!!!”

Phyllis P · Deer Park, OH

Photo of Erin Tarantino
Coldwell Banker
“I found a wonderful realtor by the name of Tamara Cecil, she worked fast and hard to help us get our house sold. Not only did I have over 20 showings in less than two days, I also had multiple offers as well with the unicorn offer of everything we wanted. She was such a great agent and I could not have chosen anyone better to sell my home. Not only was she a great agent, but also became a friend in the process. I am telling everyone I know about Tamara!”

Sarah L. · Louisville, KY

Photo of Tamara Cecil
Realty Advanced
“I am truly grateful for the amazing experience that we had. Robin's service was above and beyond. There were many challenges in the circumstances that surrounded the sale of this house and above everything else she was so kind and considerate.”

William Co Jacqueline B. · Elizabethtown, KY

Photo of Robin Cole
RE/MAX Executive Group, Inc
“Jenn took a hectic situation, selling 2 properties and looking for a new property and made it stress free. She had constant open communication and went above and beyond to get our homes sold in a timely manner and get us into our dream home. I will never recommend another realtor she will be our agent and our recommended agent for life!”

Chelsea · Independence, KY

Photo of Jen Mischke
Plum Tree Realty
“Traci and another agent from her group, Lana, helped me see as many houses as I wanted. They were very helpful and considerate. Between the two ladies, I saw so many houses and never felt pushed to buy any of them. I was informed of potential issues with houses and they respected if I didn't like something about a house. Days before I was set to go back home, Traci found a house that had just come on the market and I bought it! It has almost everything on my wish list. I couldn't be happier!”

Debra C. · Nicholasville, KY

Photo of Traci Mitchell
The Local Agents
“Lana Stephens and Traci Mitchell are a pleasure to work with. They are professional and friendly, and know their business. They not only sold my late father's townhome, they helped me completely gut and remodel it. And I live out of state! Their team put together a great plan. They kept in constant contact with plans, purchases and those things that pop-up when remodeling. I appreciate their patience, kindness and special treatment since it was my father's place. I can't think of a better fit for what I needed. I highly recommend them to work with any situation.”

Elizabeth S. · Lexington, KY

Photo of Lana Stephens
The Local Agents
“Agent Pronto helped us find a competent, efficient, talented broker at the Oatley Team!”

Susan Z. · Louisville, KY

Photo of The Oatley Team
Keller Williams Adam Borders

Frequently Asked Questions

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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