We analyze top real estate agents in Windham and across the country to find you the best veteran and military-friendly local agents, for free.
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for August 2025. *
* 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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“Matt is very kind and has a welcoming energy that is just what you need when buying a home. It can be a very stressful time when buying a home, and he made our lives easy with his attentiveness, patience, and fun spirit. He is very optimistic and has great attention to detail. If I ever look to buy a home or sell again, he will be my go to guy! Thanks Matt! I appreciate you, always!(:”
“Michele kept us informed all the way through the process of selling our home. She did well to keep our son in the loop as per our request.”
“Very professional honest trustworthy”
“Julia was very knowledgeable in the development which I moved...kept up with all the particulars...”
“Not only is Jess a wonderful agent to help navigate the unknown act of selling a home, she cared and really wanted the best for you, her client. She was always ready to answer questions and give you, the seller, advice to help the house sell faster at the best price possible. It was very apparent that Jess knows how to correctly sell a house keeping the the seller's best interests in mind. i give her a 5 star rating.”
“I was concerned from the beginning. She was there for me the whole way. Everything worked out fine, as she said it would.”
“I have purchased and sold 10 properties. Shannon is by far the best to work with. Every transaction is simply, efficient and most of all extremely pleasant with Shannon. I direct all friends and family to Shannon.”
“We were moving from Rhode Island to South Carolina and he was so helpful and listened to what we were looking for and so patient with us we took a few months but he was always checking in with us and sending photos of houses was so helpful and helped us find our Dream Home thank you Mike Matulis”
“Wadewas very professional and fast”
“Jennifer Burns is very professinal , commumicative, and available on short notice. The best !”
“Cassandra was amazing to work with! We relocated from another state and that in itself is stressful but she made it easy with her detailed video walk-through and constant communication. She's professional, kind and incredibly organized. She even lent us her air mattresses so we could spend our first night in our new home comfortably before our moving truck arrived. Truly above and beyond throughout the entire process! We highly, highly recommend her!”
“Sean is very attentive to your needs, always available answering questions or last minute requests to viewing properties. His knowledge on all subjects pertaining to real estate is impeccable. This was my seventh real estate transaction in 40 years and with my experience with other agents he is by far the most professional and honest agent I have worked with!”
“Buying your first home can be scary, but Todd made the process as easy as I could have ever wished for. He stayed in touch the entire way, and when problems came up, he turned them into learning opportunities for me. I learned so much from the way he broke things down and helped me understand every step. Todd took care of every problem and obstacle we ran into, making the whole experience smooth!”
“It was a pleasure working with Kellie and I look forward to working with her again”
“Gerald Burkett did an excellent job of marketing our property. He is really good at dividing properties into separate parsels to facilitate the overall sale. I would definitely use him again to sell any property.”
“Rosario exceeded my expectations by demonstrating understanding and competency with the process of purchasing a new home. She was able to explain and answer our questions exceptionally.”
“Crystal was absolutely amazing. Not only did she help me during a difficult time, but had all the resources available to help find a home quickly and exactly where I wanted to be. She helped me with every aspect of securing a bridge loan quickly, and finding the perfect place for me within weeks. She walked into my house as a stranger and walked out the same day as a friend. I have never received more support and help from a realtor, it was all about me and my needs, never about her. She was always available to help, explain and answer all my questions, usually within minutes. I dont think I would have gotten through this with out her help. But she made it easy, quick and (almost) painless. She was a total Godsend.”
“Lee Hurst was outstanding throughout the entire process. We ended up buying a house sight unseen, and I don't think we could have done that if we did not trust Lee. From the very beginning, Lee was responsive and communicated in a timely manner with us, and that led to a level of trust. No matter the situation or question that came up, Lee did an outstanding job of putting our minds at ease with answers and communicating our concerns to the Seller. I am not sure if we will ever buy another home, but if we do, I will definitely reach out to Lee again. Coming from Seattle, WA, I am not very networked in Oklahoma, but I would not hesitate to recommending Lee to my family and friends. Brent Biggerstaff”
“Eric Ropp is a top notch real estate agent, that is knowledgeable, and great to work with. I have worked with Eric on prior and current real estate transactions and plan to work with Eric in the future. I highly recommend Eric for any of your real estate needs.”
“I would give Katelyn a million and one stars! She's mastered her skills and knowledge! 4th time working with Katelyn, and all have been exceptional! I recommend 110%💪🫵❤️🙌”
Information and statistics on the latest trends in the Windham real estate market, updated for August 2025. *
The typical home value in Windham is projected to be $494,500 for the month of July. June’s finalized data reported the typical value of a home in the city to be $497,000—up 8.75% over the previous 12 months. For comparison, county-level data pegged home values at $589,090 in Cumberland County for the most recent reporting period. That number is expected to float around $608,640 in July.
Windham had 46 new listings and 34 listings that went under contract in June, increasing the area’s total available inventory to 59—up 9.26% from the previous month. Inventory is projected to have further increased in July.
Of those 59 active listings, 35.59% reduced their price in the month of June. The median listing price for homes in Windham fell 1.26% from May to June, bringing the current median listing price to $592,450. Based on projected data for July, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract fell year-over-year. In June 2025, the median time for a listed property to go pending was 18 days, compared to 24 days in June 2024. However, in recent months the median number of days from listed to pending appears to be rising. That trend is predicted to have carried through to this July.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Windham offers its residents a vibrant community filled with picturesque parks, engaging local events, and convenient access to outdoor recreation, making it an ideal place to live and thrive.
Windham offers a blend of serene countryside and lively community spirit, drawing families and professionals seeking an ideal place to call home. Just a short drive from Portland, this town delivers the comfort of suburban living with easy access to the region’s employment and cultural opportunities. The draw of Sebago Lake State Park is ever-present, providing residents with opportunities to paddle, swim, or hike amidst some of the area’s most beautiful natural scenery.
Outdoor activities thrive here—from fishing on the Presumpscot River to biking along the Mountain Division Trail, there’s no shortage of ways to enjoy Windham’s landscape. For shopping and dining, residents frequent the bustling North Windham Village, a vibrant hub teeming with local restaurants, specialty shops, and community events. Families appreciate the highly regarded Windham Raymond School District, which includes schools like Windham High School, celebrated for its academic and extracurricular achievements.
Cultural enthusiasts find a home at the Schoolhouse Arts Center, where year-round theater productions and arts education create a close-knit creative community. For local knowledge, the Windham Public Library is a resourceful haven, while the annual Windham Summerfest brings together residents with music, parades, and food in a true show of hometown pride.
Whether you’re searching for a peaceful retreat or a place full of community connection, Windham excels in maintaining a welcoming atmosphere and strong educational foundation. If you’re ready to make your move, Agent Pronto is equipped to match both home buyers and sellers with the right real estate expertise for a smooth journey ahead.
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!
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 Windham 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.
Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Windham. 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!
Tips and market insights to make your Windham real estate journey a success.
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.
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.
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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