“Professional and easy to work with”
OWN Real Estate, LLC
- Agent Pronto
- Virginia
- Windsor
The best way to find top real estate agents in Windsor, VA
We analyze thousands of real estate agents in Windsor and nationwide to find you proven local professionals, for free.
Compare top Windsor real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for October 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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Windsor real estate Market Report.
Information and statistics on the latest trends in the Windsor real estate market. *
Latest Rolling 3-Month Snapshot
Jun 1, 2026 - Aug 31, 2026
Median sale price
$400K
-0.7%
from Q2 '26
Median list price
$560K
+2.4%
from Q2 '26
Active listings
40
+2.6%
from Q2 '26
Homes sold
11
+10%
from Q2 '26
New pendings
10
-17%
from Q2 '26
New listings
16
-38%
from Q2 '26
Quarterly Pricing Trends for Windsor
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Windsor
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Windsor
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Windsor
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 Windsor
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 Windsor
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
40
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 (Jun 2026 - Aug 2026).
Inventory in Windsor has expanded noticeably in this rolling three-month view, with active listings up sharply from a year ago and months of supply climbing more than fourfold to 5.2 months. Even with more choices on the market, homes are taking longer to sell, as median days on market have risen about 22% year over year to 51 days.
On the pricing side, typical home values have edged down nearly 4% compared with last year, even as the median list price has surged more than 40% year over year. This gap between sale and list trends suggests sellers are testing higher asking prices while buyers remain more price sensitive.
Contract activity shows steady interest, with homes sold up modestly from a year ago and pending sales higher by about 26% in this same rolling period. At the same time, roughly 36% of recent sales closed above list and the average sale-to-list ratio is just over 100%, indicating well-priced homes can still attract strong offers. Buyers navigating these mixed signals and sellers trying to position their homes effectively can both benefit from an Agent Pronto–recommended real estate agent to interpret the local data and guide their next move.
Learn more about what Windsor has to offer.
Windsor offers residents a close-knit community with small-town charm, convenient access to outdoor recreation and local amenities, and a welcoming, neighborly atmosphere.
Windsor offers small town living with practical access to larger job and shopping centers in Suffolk, Chesapeake, and Norfolk. Located along U.S. Route 460, it provides a straightforward commute while keeping a quieter, residential feel that appeals to both long‑time residents and newcomers.
Daily life is centered around local amenities and community services. Families appreciate Windsor Elementary School and Georgie D. Tyler Middle School, both part of Isle of Wight County Schools. Outdoor time often revolves around Windsor Town Center and Garris Park, with playgrounds, walking areas, and town events that make it easy to connect with neighbors.
Local dining spots and everyday conveniences line the main corridor, while bigger-box shopping and healthcare options are a short drive away in Isle of Wight County. The Windsor Library and community programs offer activities for all ages, and town services like public works and planning are coordinated through the Town of Windsor offices.
Whether you are moving across town or relocating from a nearby city, a real estate agent who knows Windsor’s streets, school zones, and back‑road commute routes can simplify every step. Agent Pronto connects buyers and sellers with local experts who help reduce stress and keep the process on track.
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See why so many people rely on Agent Pronto to make their real estate journey a success.
“It was a pleasure working with Wes on the sale of my home. He is professional, knowledgeable and informative. He was always available to answer any of my questions. I was able to sell the house quickly with no major hold ups. Thank you again Wes.”
eXp Realty, LLC
“Brooke sold us two properties, one rural hunting property that will be built on someday and a residential property until then. She serviced both spectrums for us.”
Century 21 Legacy
“We loved working with Bree!! She was very responsive, knowledgeable, knew what to ask, and really looked out for our best interests! We were looking for a vacation home over two hours away and she was with us every step of the way. I would recommend her to anyone, she makes it so easy and a great experience.”
Century 21 Realty at Home
“Kris kept in constant communication with expert advice to get us through the closing. She keep us in focus & redirect when we needed help through several delays to closing. Kris listened with patience & understanding & represented us with her expert knowledge. Thank you is not enough we appreciate you in many ways.”
NextHome Mission
“Judy Petrak is one of those rare agents that has a superb combination of utmost competence, great communication skills, enthusiasm, honesty and superior knowledge of the local Realestate market. Totally satisfied with the outcome of the sale.”
Century 21 New Millennium
“Debbie has great local knowledge and can recommend great people for services for your home. She has a great personality and we enjoyed spending time with her. She is definitely on your side with negotiations and contracts. She knows her stuff!! Highly recommend.”
DM
The Real Estate Group
“It was a pleasure working with William Mallory. He is patient, diligent, and has the buyers best interest at heart. I recommend working with him as he makes the home buying experience exciting and makes you feel supported throughout the process.”
Iron Valley Real Estate
“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
“Gurdeep is a top notch realtor. We have worked with her over the last 16 years on the purchase of 3 homes and the sale of 2 homes. Gurdeep has handled each transaction with extraordinary knowledge, professionalism, and care. She has a keen eye for detail and makes sure all aspects of the sale are done correctly. She is incredibly articulate and uses her skills to finesse through challenging moments with excellent negotiation skills. Her media presentation for our property included a beautiful flyer presentation and drone footage of our 5 acre property that were completely above and beyond. This attracted serious buyers immediately. We have always had a fantastic experience with Gurdeep and we can’t recommend her enough! If you want the BEST, then choose Gurdeep!”
Century 21 New Millennium
“Marc is the consummate professional, with top notch expertise and excellent people skills. Marc creates an environment where you truly feel heard and understood, and he makes you feel completely at ease throughout the entire process. Marc is very responsive and easy to get in touch with. A true pleasure to work with, I would highly recommend him.”
Century 21 New Millennium
“We were looking for a house in a certain area and told Pam of our needs. A house came on the market and she emailed me the listing right after it went live. We were the first people to call and tour the house and put in an offer, and I believe that the fast work that Pam put in was a decisive factor in how we got the home. There were days when I might call Pam half a dozen times and she always answered the phone and I could tell she had a smile on her face. This is the second time I've worked with her and I will definitely do it again in the future.”
Century 21 Century21 New MILLENNIUM
“Jamie and his team are top tier. I have full confidence that we would not have had the same level of success had we not partnered with them. For those looking for a team that differentiates themselves, James Strum and the Strum Group is the obvious choice!”
Long & Foster Real Estate Long and Foster
“It was a pleasure working with Debra. Her approach to getting my house sold quickly and for the best price was just what I needed. She easily navigated the many obstacles that came up during the process and her knowledge and experience really made the difference. I felt very much at ease knowing Debra was on the job.”
Century 21 New Millennium
“a excelent realtor. very profecional”
Carrington Real Estate
“It was my pleasure working with you Daniel. You listened to my concerns and responded positively. Thank you”
Real Living Real Estate RLAH @properties
“We were so happy we picked Karen as our realtor. The only realtor that told us Virginia is a buyer beware state. The process is long and Karen has the patience and flexibility to work with you. We received excellent customer service and highly recommend her for all your realtor needs. Thank You, Karen for helping us find our new home.”
Century 21 Realty @ Home
“I cannot recommend Lindsay enough. She was always available to answer my questions, kept me updated throughout the entire process, and made what could have been a stressful experience feel smooth and manageable. She genuinely cared about helping me find the right home and was there every step of the way. I am extremely grateful for all of her hard work and would not hesitate to work with her again or recommend her to my family and friends.”
NextHome Mission
“Carla is a seasoned agent with a wealth of knowledge in the Northern Virginia area. We worked with her in the past, both buying and selling homes. We were extremely happy throughout the process then, and on the recent sale of our home. She is the only agent I would use going forward should the need arise. Thank you Carla!!”
Century 21 New Millennium
“Nick was great to work with! He was very personable and easy going. He made time for every home we wanted to see at the exact times we wanted to see it. He stuck with us even after a 6 month lull in looking at homes. I would consider Nick not only a professional, but he has become a friend.”
Century 21 New Millenium
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 Windsor. 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 Windsor Realtor® or real estate agent today.
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