Find the perfect real estate agent in Windsor, VA

We analyze top real estate agents in Windsor and across the country to find you the most proven local agents, for free.

Customer Reviews Equal Housing Opportunity
Windsor, VA real estate

The easiest way to find the best real estate agent.

Sell your home fast and for top dollar or find your dream home at the best possible price. Use our free service to find top agents you can trust.

Tell us what you need.
Answer a few quick questions about your real estate needs so we can begin our search.
Match with the perfect agent.
Our personalized matching system will connect you with a top-rated real estate agent with the local expertise and experience you need.
Meet your agent.
Review the details of your top agent recommendations and speak with them to learn exactly how they can make your real estate journey a success.
Buy and sell with confidence.
While real estate decisions are among the most important financial and personal decisions we make, you can rest easy knowing that you have a proven real estate professional on your side.
Agent profile screenshot
Agent profile screenshot

Home buyers and sellers love Agent Pronto.

Here’s what some of the 400,000+ home buyers and sellers have had to say about our service.

“Because I was trying to do a long distance short sale, I needed someone who really knew what they were doing. I was given the name and number of Colin. He took on the challenge and a little over two years later, we finally closed. If you have done a short sale before, it is a very trying ordeal! Colin took good care of the house, had repairs done, and always had clients waiting in line with a new contract. I believe it was the 5th contract and a lot of patience that got us to closing.”
5 stars
DW
Denise W.
Norfolk, VA
“Great communication and overall great service!”
5 stars
EH
Ed H.
Chesapeake, VA
“Deb Kelly did a fantastic job!”
5 stars
JL
Jeannine L.
Hampton, VA
“Kimberly and Holly were very personable and professional. They were very informative. They guided us through this cumbersome and tedious process. They both were great to work with and kept us abreast with what we needed to do to sell our home. We are most grateful to work with them. They know what it takes to sell a house!”
5 stars
DP
Derald E P.
Newport News, VA
“We had a 5-star experience. Thank you so much for helping us close on our new condo!”
5 stars
MC
Maryjane C.
Virginia Beach, VA
“Mark was a great person to work with. I found him to have a high level of integrity and I would not hesitate to recommend Mark or use him again if conditions warranted. Mark was a pleasure to work with and I feel that he placed my requirements above his, a wonderful representation of a professional realtor and individual. Highly recommended!!”
5 stars
EA
Edward M A.
Chesapeake, VA
“My overall experience has been great! My wife and I decided on the same Realtor - which is rare we agree after 38 years. We chose Raquel Ott and she has done a superb job for us!!”
5 stars
EP
Earl P.
Reedville, VA
“Angela Fink was wonderful! She was professional, personable, and kept me updated and informed on all issues. I would highly recommend her to my family and friends should they need a real estate agent.”
5 stars
SN
Shirley N.
Free Union, VA
“Melissa Sanford was like an angel sent to me. She was professional...she kept me informed every step of the way and closing was a breeze. I would recommend her as an agent to anyone looking to sell their home/land. If I could give her more than five stars, I would.”
5 stars
AB
Annmarie B.
Gum Spring, VA
“Excellent. Very professional and supportive. It was a pleasure working with Dwight.”
5 stars
SJ
Sue J.
Pulaski, VA

Windsor real estate Market Report.

Information and statistics on the latest trends in the Windsor real estate market, updated for May 2025. *

Windsor, VA real estate
60
Buyer’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.

* Data provided by Redfin, a national real estate brokerage.

Learn more about what Windsor has to offer.

Windsor offers its residents a charming community with rich history, welcoming atmosphere, and convenient access to local parks and amenities.

Windsor is a community where the slow pace of life beautifully intersects with modern conveniences and genuine Southern hospitality. Located just a short drive from Smithfield and offering easy access to Suffolk, Windsor presents residents with the rare opportunity to enjoy peaceful, small-town living while remaining within reach of bustling cities and coastal destinations.

The heart of Windsor beats within its local gems like Windsor Castle Park, where scenic walking trails and open spaces invite outdoor adventures. The annual Windsor Farmers’ Market brings fresh produce and local artisan fare to Main Street, fostering a strong sense of connection among neighbors. Educational opportunities abound thanks to the well-regarded Windsor High School and Georgie D. Tyler Middle School, part of the Isle of Wight County school district, both known for their engaging programs and supportive staff. Families are thrilled by the Windsor Library, a hub for community events and lifelong learning.

Embracing both tradition and progress, Windsor’s historic downtown hosts seasonal festivals and community parades that honor its roots, while newer developments provide fresh dining and shopping experiences. Residents enjoy the convenience of recreation at Windsor Town Center and appreciate quick commutes to larger employment and entertainment centers like Chesapeake.

For those considering buying or selling a home, Windsor offers an inviting blend of community spirit, educational excellence, and small-town peace. Let Agent Pronto connect you to the right local expert for your next move in Windsor.

Woman smiling

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!

Sarah W.

Take the guesswork out of finding an agent.

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 Windsor 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.

Data analysis with a human touch.

Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Windsor. 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!


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. 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.