Jim Winn Real Estate Agent at Re/max Realty Group

Jim Winn

Real Estate Agent at
Re/max Realty Group

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Agent Highlights

Jim sells properties fast - selling more than 48% quicker than the average Gaithersburg agent.
Jim gets the job done - completing more sales than the average Gaithersburg agent.
Jim also has Townhome expertise - working with over 122 more townhomes than the average agent.

Jim's Transactions

  • 1311 Whitetail Court
    Mount Airy
    Single Family Home
  • 9507 Ashbury Place
    Single Family Home
  • 13887 Foggy Bottom Court
    Mount Airy
    Single Family Home
  • 10607 Hunters Chase Lane
    Single Family Home
  • 8002 Sanctuary Court
    Single Family Home
  • 4300 Parkland Court
    Single Family Home
  • 4303 Weller Court
    Single Family Home

More about Jim Winn

Born in D.C. and raised primarily in the Montgomery County (MD) suburbs of Washington, D.C., Jim and Tessa, along with their 3 children, are grateful to call this region, home. Jim is proud of his military heritage as both of his parents served in the U.S. Army, and his mother would eventually serve in Real Estate for nearly 30 years, making Jim a 2nd-Generational REALTOR. Prior to Real Estate, Jim served in pastoral ministry. He completed his Bachelor of Science in Biblical studies, some post-graduate studies in Seminary, and also additional pastoral training in his local church. While Jim enjoyed working in full-time vocational ministry and especially loving and serving people, a growing desire to transition into the marketplace led to the eventual career move to full-time Real Estate in 2008. As the principal agent and team leader of JW Homes, Inc., Jim leads a team that ...
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Boyce College, Southern Seminary, SGM Pastors College


Multiple RE/MAX "Platinum Club" Awards, Multiple RE/MAX "100% Club" Awards

License Number


Jim Winn's Reviews & Ratings

Tell us about your experience with
Jim Winn

  • Jim helped me buy a home

      Jim was fantastic through the entire process. We are first time home buyers and the level of help and care he gave us was above and beyond what we had hoped for. I’ve never seen a RE agent care more about his clients.

    • Jim helped me buy a home

        My experience with Jim Winn was nothing short of excellent. As a first time homebuyer, I was anxious about starting the entire process. After all, when would I find time for all that additional stress? But one meeting with Jim was enough to put my mind at ease. He quickly proved he had the knowledge and the expertise – and the confidence – to help find what I was looking for within my budget. Jim is also an all-around great guy to work with; he always made himself available, patiently answering my random questions, checking in to see how I was doing, and keeping me updated on what was happening in the process and what to expect next. Nothing was left to mystery or guesswork. And about a month and a half after my initial meeting with Jim, I was in my very own house! I highly, highly recommend Jim Winn and his capable crew without a single doubt or reservation. Jim, Katie, and the rest of the team not only made the entire process easy, they also made home buying a fun experience—and that made all the difference to me.

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      • Jim helped me buy a home

          My wife and I are expecting our first child this spring. When we first began our home search Jim was recommended to us by a friend. This was the best thing that could have happened to us during this process. Jim is the realtor that everyone wants. He has an extreme knowledge of all things home and always has an answer to your questions. You can truly see Jim's passion for helping people as he always goes above and beyond in fulfilling your requests. From beginning to end, Jim will be there for you.

        • Jim listed and sold my home

            Jim and his entire team are top notch and I am so pleased to have chosen them to sell our home. The need was sudden, and it had to be sold as quickly as possible without sacrificing profit. On top of that, it was being listed at a time one would think is undesirable - just before Christmas and headed into the middle of Winter. Jim didn't flinch, setting up the initial meeting and walk through with immediate plans for a photographer to take shots and enable the home to "go live" within days. There was a surprisingly large number of showings given the time of year, with varied levels of interest but no immediate offers. Jim was as positive as he is experienced, staying in constant contact by phone, e-mail and video to calm any fears and lend assurance that the "right buyer would come along", which indeed happened. An offer for the asking pricing was received, JUST as the full effects of the Covid-19 quarantine were taking hold. Jim worked seamlessly with the title company to ensure a prompt and orderly "VIRTUAL" settlement process that was quite unlike anything I had ever experienced! Even at settlement, as I signed closing documents alone in a mask and gloves, Jim was right there beside me on video chat! The follow-up couldn't have been tighter and more complete, from Jim's remaining presence to the continued contact with Roanna and other members of his team. There is no such thing as a "former" client to Jim, as he runs a client appreciation program with drawings, prizes, and industry bulletins through e-mail and social media. It's truly a "once a client, always a client" mentality with this team. I am blessed and grateful for their service!

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          • Buying or selling a home is always a stressful time. It is especially true when you are on the other side of the country trying to complete these transactions. I have been through three home transactions (2 buying and one selling). By far Jim was the agent that seemed most engaged with me through all the agents I have worked with. Through this journey we had many upsets and surprises that presented different challenges. The professionalism of both Jim Winn, Katie his assistant, and his referred specialist helped to quickly deal with the stress and issues as they presented. If at any time I know of a person in the DMV area in need of a Real Estate Team, Jim is at the top of my list for referrals.

            - Gregory Straub
          • Honestly, my husband and I can't say enough about Jim. As first time home buyers, we weren't quite sure what to expect, especially with the end of our apartment lease approaching. From start to finish, Jim was there to explain the whole process to us. We were beyond blessed to have worked with Jim and, in a crazy turn of events, ended up purchasing his home! If there is any realtor everyone should have the pleasure of working with it's Jim.

            - Erin Ray
          • From the moment we reached out to Jim to begin the process of buying our first home, we were so blessed by his help. Jim... and his team were always quick to respond to any questions we had, they always made us feel like we were their first priority, and they were faithful to make sure our questions were answered. It could have potentially been a very overwhelming process as first time homebuyers, but the amount of knowledge Jim has, the endless resources, and the time he spent with us was truly remarkable and we couldn't have dreamed that everything would have gone as well as it did. We will gladly be passing along his information to anyone we know who may need a realtor in the future!

            - Buff and MB Fairchild
          • Jim is a great real state agent, provided excellent customer service to my husband Josh and I when we were looking for our first house in 2013. We also participate in his Client Appreciation Program receiving newsletters periodically, contests for prizes and referral for contractors in the area. My brother-in-law also bought a house with him last year. We recommend to all of our friends and family in the area. He cares about his clients like no other!

            - Josh and Talita Dreis
          • Jim Winn represented us as both the sellers agent of our condo in late 2016, and as our buyers agent in the Spring of 2017. Jim and his team are truly exceptional. He operates with the highest level of integrity and has his clients best interest at heart. As a sellers agent, Jim advised us on what items we could upgrade to get the best return on our property and get to a quick sale. His photographer took phenomenal pictures of our place, and Jim advertised our property widely across every channel you can think of. We feel that Jim really helped us put our best foot forward on the sale of our place. Jim also excelled when it came time to negotiate with the buyer. His negotiation skills are excellent, and we felt that we were able to get the best price for our property as a result of his skilled approach.As a buyers agent, Jim made himself available for home tours as often as needed, sometimes even last minute which was quite helpful in this competitive market where homes would go under contract within a couple of days. Jim also did excellent research on the comparable sales allowing us to make informed bids. Jim never pushed us one way or another, but rather provided us the information needed to make informed decisions. Jim is truly resilient and his positive spirit helped us remain persistent, even as we got outbid on the first few properties we pursued. We cannot say enough positive things about Jim. We would highly recommend Jim and his team to anyone looking to buy or sell a home.

            - Chris Monje and Carolyn Inoa
          • Jims team made the home buying experience far less stressful than imagined. He is willing to work with your schedule and goes the extra mile to make sure you dont encounter any major problems. For first time homebuyers we found his positive attitude encouraging throughout the entire process. The group is efficient and highly professional. We hope to work with Jim again when we sell the house.

            - Patrick LaBreck
          • Jim and his team were literally a "dream team". He covered everything from the initial meetings to get market ready down to the final details of getting ready for settlement. They don't miss a beat, and I never felt like things fell through the cracks. Jim is available (and even Katie for last minute showings). I said many times we feel like we are your only customer!! Which wasn't true, but they always made us feel that way. Jim knows what he is doing and has a great rapport with all people involved, especially the other team of realtors/lenders. He knows how to strike an awesome deal without being pushy or rude. He always made sure we knew what next steps were and always explained everything clearly and precisely. I can't rave enough. So happy we chose them for selling and buying a home!

            - Jeff and Laura Lewis
          • Jim was THE essential part of our home buying experience. He was knowledgeable, readily available, and honest. I am convinced that without him and the whole team with Jim Winn Homes we would not have found nor won the bid for our dream house! He is simply put the best!!

            - David and Izabel Saville
          • Jim was great in helping my wife and I through our first home purchase. He helped us understand the process at each step and was so patient with all of our questions. When we purchased our house we didn't have many options so when we found a house we liked Jim quickly put together an offer and negotiated it to the top of about 15 other offers! He was both diplomatic and strong in getting us the best possible deal. Thanks to Jim, my wife and I are now in our first home and loving every minute of it!

            - Michael and Camila Dygert
          • It was such a pleasure working with Jim on the sale of our home and the purchase of our new house. He was so patient as I asked many questions - sometimes repeatedly, thank you! So kind, consideration and understanding throughout the process. I am glad we called Jim after viewing one of his properties online - he responded quickly, came by shortly thereafter and became our partner and trusted agent on the journey providing sage advice all along the way.

            - Robin Thomas
          • We knew from the start of our home buying process that Jim Winn was the realtor for us. He came well recommended. We felt at peace knowing he was on our team and working hard to secure us the perfect home. Being first time home buyers, there are a lot of unknowns throughout the whole process. Jim and his staff were not only quick to help, but also well informed and had great resources. He has integrity and an incredible work ethic. He does not push his own agenda, but diligently seeks to learn what your exact wishes and desires are. He is a great advocate and doesn't press you to "get the more expensive product" so that he can walk away with a bigger commission. He was always eager to help, even being willing to talk on the phone at random times. Even though our home buying process has ended, our connection with Jim and his staff has not. We still receive client appreciation gifts as well as hand written notes and emails checking in. We join our voices with the many praises of Jim Winn and his team! You won't regret using him and will be well serviced in his care.

            - Riley and Kelsey Shenk
          • We so enjoyed having Jim as our realtor. He walked us through every part of the housing process, both the buying and selling aspects. We never felt like we didn't understand what was going on. Jim was always very patient w/us, even when we went to look at about 20 houses in one weekend. Even when we went to visit a couple of the houses 2 or 3 times, he told us to take our time and that eventually we would find the right house. We never felt pressured to pursue something we weren't comfortable with. We also were grateful for his counsel and expertise during the selling and buying process. He always steered us w/a steady hand and was faithful to help calm our fears when we were getting stressed.

            - Dan Middleton and Caylie Zidwick
          • We had a unique and challenging situation when selling our house this past summer. Our house went under contract three times due to buyers' loans falling through each time. During these six months Jim became like family to us, helping us through each step of the stressful process of selling a house (x3!). Jim was always available for our numerous questions and provided us with great business advice as well as caring for us personally as we walked through this hard season. He personally took care of snafus that occurred along the way without bothering us with stressful details when it wasn't necessary. He helped us stay within our asking price and got us the deal we were hoping for. He went above and beyond MANY times for us throughout our buying/selling process. We could not have asked for a better realtor! We also need to give a shout out to Katie, his assistant, for all her kindness and how quickly she responded to our questions as well. Jim was able to provide us with great business sense only because he has a wonderful executive assistant taking care of so many things behind the scene for him. We love them both!

            - Gene and Renee Huston
          • Jim was our second realtor for selling our house. We had been on the market for 4+ months with nothing. We moved to Jim and had 3 offers within a week. Blew my mind. I wish I started with him as it had been a painful experience before. With Jim it truly was painless. Collaborative and very much believe in open communication. He treats his clients like family. Will always recommend Jim.

            - Dan Shapiro
          • Jim and Katie did an incredible job seeing us through the entire home-buying process. They were responsive, knowledgeable, and committed to walking us through every single detail along the way. They provided constant, timely responses to our many questions and were patient, organized, and very professional in all of their work. When we found the house we wanted at 2pm on a Sunday, they were able to help us submit a competitive offer within several hours! Would recommend them without hesitation to any prospective home buyers!

            - Billy and Carrie Buttrey
          • Originally, we weren't looking forward to the house-buying process thinking it would be stressful but Jim and his team proved us wrong all the way through. We couldn't have been more happy with the process. They were on top of everything and managed the paperwork with great care. From start to finish, we experienced outstanding customer care, transparency, and ease of mind. Highly recommend them!

            - Ezequiel and Carolina Galeano
          • Jim Winn is an amazing agent! He came to us highly recommended from our friends who recently purchased a new home with Jim's assistance. Jim is extremely knowledgeable about the real estate markets. He was never too busy to take our calls or emails and has a fantastic office team as well. From start to finish we could not have asked for a better person to be by our side. In both the selling of our townhome in Germantown to the purchase of our single family home in Sykesville Jim had all the details covered. This guy knows his stuff and has your back!!! The only thing I can say is USE him!! He has definitely earned our business for life.

            - Nancy Damiano Kirkpatrick
          • Jim is awesome. He knows the markets and his business. He is super positive and calming through the whole process. If you are fortunate enough to work with Jim to either buy or sell your property just do what he says and be ready to see results!! An awesome feature about Jim is that after your transaction, he doesn't forget who you are! He is still available to answer questions and help us in any way he can even after our deals have long since been done. This is a rare and valuable trait in a professional. Jim has earned our business for life! Now if we can just get him to come with us when it is time to move out of state...

            - Carl Kirkpatrick
          • Excellent is an understatement when describing our experience with Jim and his team. He is a true professional, as a Realtor his abilities and skills are second to none. He and Katie are quick to help, provide information, and follow up. The amount of communication, guidance and assistance would seriously lead you to believe that you are his only client, and that their only focus is you and your satisfaction. Furthermore at no point is the sale of your current home, search for a new home, or purchase of your new home about anything other than what is best for you and your family. He will not let you compromise, settle for "just okay", or push you into something that is not right for you. And when you find "the one" he will put everything on hold and not give up until "the one" is your new home. However, Jim truly cares about you and your family and this is what raises him above all others. The question he always asks is how you are, and not just a general "how are you?" but a sincere "how are you Jamie?......how are you Heather?......how is the family, kids, dogs, etc....?" And he truly listens to each response and whether it be a day or a week he checks in with you to see how you personally are doing, the sale of your home, search for a new one is secondary to his concern for you and your family. And this genuine concern for you and your family does not end with the sale of your home and/or purchase of a new home as he regularly sends mail checking to see how everyone is doing, and every few months he personally stops by whether it be to drop off leaf bags during the fall or lawn bags during the spring, or just to say "hi". This review could go on and on with nothing but positive words to describe Jim and his team, but to conclude we can honestly say that if you are looking for a true professional, a genuine person, and a Realtor who does things right for all the right reasons than look no further than Jim, we could not speak more highly of him, and have no doubt that if you go with Jim you will be writing a review similar to this yourself in the near future.

            - Jamie and Heather DeFelice
          • We are so thankful to have Jim Winn as our realtor! Before we bought our home, we had about 4 different realtors to choose from. What stuck out about Jim to us was his amazing ability to follow through so quickly on every single thing we talked about. Jim went above and beyond to help us understand the process of a short sale, took on extra work when dealing with the many banks involved in the sale, and even took the responsibility to fix mistakes committed by one of the parties involved. Since the purchase of our home (about 2 years ago), he has stayed in touch by sending us very informative newsletters, and easy-to-read analyses of our local market. He's simply amazing and we are convinced he is the best realtor out there!

            - Marcos and Priscila DaRocha
          • We received Jim's name from a friend who recommended him highly and my wife and I were not disappointed. Jim is a great agent who understands his profession well and always willing to go to bat for his clients. He is not only well versed on current market trends, but is very knowledgeable in dealing with people. He gave us great advice and was patient as we looked at multiple homes for several months. He is gifted and good at what he does, but the most important thing I can say about Jim is that I TRUST him!

            - Chul and Lauri Yoo
          • Our offer was lower than several competing offers for the house but Jim with his excellent negotiation skills was able to win the deal for us. Also, Jim was open and available to answer any questions we had throughout the whole process.

            - Mitch and Allie Paredes
          • Jim recently helped me sell my home for waaaay above asking price and within 1 week of listing. My house is now the highest selling home in the neighborhood. He gave me great advice that helped sell the home quickly. He was ALWAYS available to answer my questions. If he couldn't answer the questions himself, he directed me to a professional who could. He was by my side assisting me through the entire process. He explained things well and made me feel comfortable with everything. I highly recommend Jim! He's awesome to work with! You won't be disappointed! Thanks for everything Jim!

            - Dora Chapman
          • We have been working with Jim for over a year discussing the market and deciding when the right time for us to sell would be. He was very informative and knowledgeable while guiding us. When we decided to move forward it was perfect timing. Not too mention that our house was on the market for just under 10 days and sold nearly at list price - easily the highest price for a home in a very active neighborhood. During the process he always had suggestions that were sound and forward looking as he did a great job of anticipating the buyers' next move. Most impressive was the way he handled very difficult buyers minutes before settlement. He was able to smooth over their concerns and close the deal. He even set us up with another local realtor to the location we were moving to in another state. Can't say enough about stewardship and care he puts into every detail!! Katie, his assistant, is also very attentive and helpful! A great team.

            - Mike and Stacy Hollen
          • There's a lot I could say about Jim - from him not forcing us in a house we didn't want, to being patient with us even though we made some mistakes, to even his willingness to help us close during the heaviest snow fall in Maryland recent history! Overall you can't say Jim's faith doesn't play a role how he treats others and sacrificially makes time for his clients all the while making sure to be there for his family. Katie his assistant was also very helpful to answer questions. My only regret is knowing that many others will not know how great a realtor he is and how before, during, and way after the sale, he is still involved in your life and bringing gifts all the time when most realtors just leave you in the dust. Another regret is knowing if I ever want to find a home outside of Maryland, I won't have a good man like Jim to help me find a great house. SO PLEASE if you want the best experience in getting a house or even if your just want to see what you can afford, please contact Jim and Katie.

            - Jonathan George
          • Jim knows what he's doing and is easy to work with...simply the best.

            - Joe and Julie Giove
          • One month ago, today, Jim Winn was by our side as we settled on our first home! I call it a 'home' because Jim helped us purchase a house that we had always dreamed about, but never thought we would actually have. The DC area is a quick-growing, mostly unaffordable, area for first time homeowners, and our job locations were not as forgiving. One of us traveling east of Baltimore every day, and the other commuting to Greenbelt, we spent months trying to find the right location with that community feel. Jim was patient, committed and always open to our opinions. He promised us that we would find the right place and we should not settle until we did. Not even two months ago we saw the listing for an amazing home and we knew it was the one. Jim was quick to connect with the selling agent and helped direct us through the bidding process. We were shocked when the seller said "it is yours"! Almost sounded too good to be true! Today, we still could not be happier and we are honored to have been able to work with Jim. We would not recommend anyone else to help you find your dream 'home'. Thank you Jim!

            - Laura Brickley
          • Jim is not only a great realtor, he's a great individual and a man of God! This guy went above and beyond to help me purchase my first home. He was there for me every step of the way, and even though we did not have a prior relationship, I had no doubt in my mind that he was all about serving me and helping me purchase something that my family and I would love and could handle. When you meet an individual like Jim, you will not only want to work with him, you will want to become his friend. I'm glad that I have Jim in my circle.

            - Troy Green
          • I highly recommend Jim for anyone looking to purchase or sell a home in Maryland. Don't let his unwavering kindness fool you into thinking he's reluctant to go to bat for his clients. He'll negotiate and structure a deal better than anyone in the industry, and all the while, treating everyone with respect (a rarity in this profession). He's definitely a one stop shop for all your real estate needs.

            - Duke Walker
          • Jim helped my wife and separately my mother-in-law find a home. Not only was he patient with us, new to the home owning process, but he was professional, available and showed his experience in every circumstance from viewing a home to the settlement. I would recommend Jim wholeheartedly to anyone going through this process!

            - James Overman
          • We are an immigrant family who have been living in the US only 4 years. So, when we decided to buy a home we were stepping into a huge and complicated legal, financial and business system and were feeling like inexperienced swimmers thrown into a deep and stormy sea. However, when our friend from the Covenant Life Church recommended Jim we felt more confident being sure that God was leading us to the right direction. After we first met Jim, our confidence was 100 % and we realized that God entrusted us to a person who combined high professionalism with dedication to customers. All advice given by Jim hit the target and during all the buying process we were led through its dark forest by his skillful hand and friendly support. Thank you, Jim and Katie! You took an important part in our obtaining of the American Dream!

            - Yury Petrov and Victoria Kapustina
          • Love the service, excellence, and thoroughness. Great guy!

            - Kris and Jess Marcantonio
          • Thanks, Jim, for all of your hard work in selling our house. It was our first home as a family. We are grateful that, thanks to you and your fantastic team, we can celebrate our house being sold!

            - Steve and Beth Techtmann
          • Jim Winn is my real estate agent and he has become a friend. He helped me sell one house through difficult times and purchase another under happier circumstances. Jim also worked with my daughter and her husband when they purchased their first home. Jim is very professional and knowledgeable. He always provided a very positive outlook. His friendly, happy and supportive manner was a pleasure at all times. I highly recommend Jim for real estate sales and purchase.

            - Chuck Eirkson