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Windsor, VA real estate

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

Jul 1, 2026 - Sep 30, 2026

Median sale price
$355K
-12% from Q2 '26
Median list price
$524K
-4.2% from Q2 '26
Active listings
39
No change from Q2 '26
Homes sold
13
+30% from Q2 '26
New pendings
11
-8.3% from Q2 '26
New listings
20
-23% from Q2 '26

Quarterly Pricing Trends for Windsor

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

Quarterly Pricing Trends for Windsor Q4 '21 Q4 '22 Q4 '23 Q4 '24 Q4 '25 Q3 '26 Median sale price in Oct 2021 - Dec 2021: $234K Median sale price in Jan 2022 - Mar 2022: $260K Median sale price in Apr 2022 - Jun 2022: $361K Median sale price in Jul 2022 - Sep 2022: $280K Median sale price in Oct 2022 - Dec 2022: $300K Median sale price in Jan 2023 - Mar 2023: $275K Median sale price in Apr 2023 - Jun 2023: $392K Median sale price in Jul 2023 - Sep 2023: $335K Median sale price in Oct 2023 - Dec 2023: $388K Median sale price in Jan 2024 - Mar 2024: $410K Median sale price in Apr 2024 - Jun 2024: $350K Median sale price in Jul 2024 - Sep 2024: $363K Median sale price in Oct 2024 - Dec 2024: $347K Median sale price in Jan 2025 - Mar 2025: $406K Median sale price in Apr 2025 - Jun 2025: $406K Median sale price in Jul 2025 - Sep 2025: $413K Median sale price in Oct 2025 - Dec 2025: $364K Median sale price in Jan 2026 - Mar 2026: $398K Median sale price in Apr 2026 - Jun 2026: $402K Median sale price in Jul 2026 - Sep 2026: $355K Median list price in Oct 2021 - Dec 2021: $210K Median list price in Jan 2022 - Mar 2022: $345K Median list price in Apr 2022 - Jun 2022: $275K Median list price in Jul 2022 - Sep 2022: $320K Median list price in Oct 2022 - Dec 2022: $249K Median list price in Jan 2023 - Mar 2023: $390K Median list price in Apr 2023 - Jun 2023: $322K Median list price in Jul 2023 - Sep 2023: $395K Median list price in Oct 2023 - Dec 2023: $372K Median list price in Jan 2024 - Mar 2024: $350K Median list price in Apr 2024 - Jun 2024: $355K Median list price in Jul 2024 - Sep 2024: $365K Median list price in Oct 2024 - Dec 2024: $430K Median list price in Jan 2025 - Mar 2025: $350K Median list price in Apr 2025 - Jun 2025: $420K Median list price in Jul 2025 - Sep 2025: $410K Median list price in Oct 2025 - Dec 2025: $409K Median list price in Jan 2026 - Mar 2026: $385K Median list price in Apr 2026 - Jun 2026: $547K Median list price in Jul 2026 - Sep 2026: $524K Oct 2021 - Dec 2021 Median sale price $234K Median list price $210K Jan 2022 - Mar 2022 Median sale price $260K Median list price $345K Apr 2022 - Jun 2022 Median sale price $361K Median list price $275K Jul 2022 - Sep 2022 Median sale price $280K Median list price $320K Oct 2022 - Dec 2022 Median sale price $300K Median list price $249K Jan 2023 - Mar 2023 Median sale price $275K Median list price $390K Apr 2023 - Jun 2023 Median sale price $392K Median list price $322K Jul 2023 - Sep 2023 Median sale price $335K Median list price $395K Oct 2023 - Dec 2023 Median sale price $388K Median list price $372K Jan 2024 - Mar 2024 Median sale price $410K Median list price $350K Apr 2024 - Jun 2024 Median sale price $350K Median list price $355K Jul 2024 - Sep 2024 Median sale price $363K Median list price $365K Oct 2024 - Dec 2024 Median sale price $347K Median list price $430K Jan 2025 - Mar 2025 Median sale price $406K Median list price $350K Apr 2025 - Jun 2025 Median sale price $406K Median list price $420K Jul 2025 - Sep 2025 Median sale price $413K Median list price $410K Oct 2025 - Dec 2025 Median sale price $364K Median list price $409K Jan 2026 - Mar 2026 Median sale price $398K Median list price $385K Apr 2026 - Jun 2026 Median sale price $402K Median list price $547K Jul 2026 - Sep 2026 Median sale price $355K Median list price $524K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
35
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 (Jul 2026 - Sep 2026).

Inventory in Windsor has expanded notably in this rolling three-month view, with active listings up sharply year over year and holding at 39. Contract activity has also picked up compared with a year ago, as homes sold have increased significantly while new listings have risen even faster, suggesting more options but also more movement through the pipeline.

Pricing is adjusting to this added supply, with the typical home value down double digits from a year earlier even as the median list price has climbed substantially. Longer marketing times, now at a median of 51 days and higher than a year ago, indicate buyers have more breathing room to evaluate properties before committing.

Conditions have shifted from very tight to more balanced, with months of supply jumping severalfold year over year to 5.7, yet the area still registers as a seller’s market. Even in this cooler environment, roughly 31 percent of recent sales closed above list price and the average sale-to-list ratio remains close to 100 percent, showing that well-priced homes can still attract strong offers. Buyers and sellers who want to navigate these changing dynamics can rely on Agent Pronto to connect them with a local Windsor agent who understands both sides of the deal.



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.

Find your Windsor 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.

“Highly responsive - from initial request to closing was about five weeks, 5 weeks and I'm sitting in my new home writing this review! William was friendly, helpful and flexible. Not only did he show up on time and get back to me on my home searches quickly, he answered my questions on time and actually, in a thoughtful way, I could tell he cared for my well being when choosing a new home. I would absolutely recommend William Mallory, we will definitely be using him again in the future!”

Keith Tuggle · Portsmouth, VA

Photo of William Mallory
Iron Valley Real Estate
“Judy is awesome! This is the second time she has been our real estate agent. I have had other agents and by far she is the best! She is completely on your side and vested in your best interest. She knowledgeable and always very communicative, reliable and listens to your needs and feedback. She was a pleasure to work with on our real estate journey.”

Wendy · Woodbridge, VA

Photo of Judy Petrak
Century 21 New Millennium
“It was great to once again work with Debra Mcelroy to find a new house. She had previously helped me find my first house in Virginia and this year, she helped me sell that house and purchase a new one. Because of my previous experience with her, I didn't even consider any other agents. And that decision paid off tremendously. She sold my house quickly and for a great price, then help me successfully win the bidding on the house I really wanted to purchase. Throughout the process, she was always on top of things and always available to respond to my questions. Her knowledge and experience were evident throughout and made the difference in several difficult situations.”

Darren Wright · Woodbridge, VA

Photo of Debra McElroy
Century 21 New Millennium
“Mike was knowledgeable about the area and understanding what was important to get our property sold. We had a very unique property that he was able to market and price very well. He was extremely efficient and helpful in the entire process, even before we officially decided to work with him, he took time to research and inform us on tax status that we were unaware of in order to successfully accomplish the goal of selling our property. He was patient but also urgent in his communication and helping us everything needed to reach our goal. We would definitely work with him again and refer him to others! 10/10 highly recommend!”

Darrell Bond · Kingsport, TN

Photo of Creation Properties
Century 21 Legacy
“Gurdeep did an exceptional job as our realtor. We were first time homebuyers and she made sure that we had all the information we needed throughout the process. The sellers gave us a tight timeline to close and she worked proactively with the inspectors and loan company, even on weekends, to make sure deadlines were hit. We had a smooth closing and she has also given us great contractor recommendations. Thank you Gurdeep!”

Megan Andersen · Alexandria, VA

Photo of Gurdeep Mangat
Century 21 New Millennium
“Regina was easy to work with always answering my calls, and explaining all my questions. Thank you for all your help!”

Rusty and Tania · Hiwassee, VA

Photo of Regina Piland
Century 21 Valley Real Estate
“Working with Marvin James was very smooth and easy being this was my first time purchasing a home everything was quick and if I had any questions he was quick to answer them for me.”

Matt R · Wingina, VA

Photo of Marvin James
eXp Realty
“Bree was amazing to work with as first-time home buyers! She made the entire process easier, answered all of our questions, and was always there to help us along the way. We’re so grateful to have had her help finding our first home and would absolutely recommend her to anyone!”

Scout · Powhatan, VA

Photo of Bree Cox
Century 21 Realty at Home
“Pam Milan is truly one of the best real estate agents I have ever worked with. From the very beginning, she was so caring, patient, and supportive throughout both the sale of my home and the purchase of my new home. She was always available to answer my questions, no matter how many I had, and she made a stressful process so much easier for me. I truly appreciate all the time, effort, and care she put into helping me. She is professional, knowledgeable, trustworthy, and genuinely cares about her clients. I highly recommend Pam to anyone who is buying or selling a home. You will be in great hands with her!”

Afrooz Pour · Fairfax Station, VA

Photo of Pam Milan
Century 21 Century21 New MILLENNIUM
“Sara Andrews Hart is a professional realestate agent who deeply cares about her clients and works tirelessly on their behalf. Communication is an exceptionally strong suit as realestate transactions are multifaceted and can be complicated. She navigates challenges that arise and has a plethora of resources to handle them; therefore, allievating much stress for home sellers. She is highly recommended.”

Sandra · Virginia Beach, VA

Photo of Sara Andrews Hartz
The Real Estate Group
“Professional and easy to work with”

Herb Cross · Chesapeake, VA

Photo of Wanda Harris
OWN Real Estate, LLC
“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.”

Wayne · Mount Jackson, VA

Photo of Wes Sparks
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.”

Jerry · Church Hill, TN

Photo of Brooke Shelton
Century 21 Legacy
“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.”

Jamie Jochum · Fredericksburg, VA

Photo of Kris Riley
NextHome Mission
“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.”

Thomas & Karen Sweeney · Chesapeake, VA

DM
The Real Estate Group
“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.”

Mary · Ashburn, VA

Photo of Marc Massis
Century 21 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!”

Scott McConnell · Powhatan, VA

Photo of The Strum Group
Long & Foster Real Estate Long and Foster
“a excelent realtor. very profecional”

Marcial Flores · Woodbridge, VA

Photo of Alfonso Torres
Carrington Real Estate
“It was my pleasure working with you Daniel. You listened to my concerns and responded positively. Thank you”

Cecilia Doe · Beltsville, MD

Photo of The Washingtonian Group
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.”

Joe & Denise · Glen Allen, VA

Photo of Karen Dailey
Century 21 Realty @ Home

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 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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