Jim Winn, REALTOR®
Exceeding expectations through successful negotiations and outstanding client services.
6 Montgomery Village Ave
Suite 200
Gaithersburg, MD 20879
301.258.7757 x505
Direct 301.921.4505


Jim Winn || Principal Agent & Team Leader- JW Homes, Inc.


Born 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 includes 3 other licensed agents, full-time administrative assistance, and transaction and marketing coordinators- and therefore is able to provide enhanced, top-notch services to his clients – transactionally and relationally. Our team mission is “Exceeding expectations through successful negotiations and outstanding clients services.” And we have utilized the acronym SCALE, to articulate our pursued core team values: Serve, Care, Advocate, Love and Enthusiasm. Jim loves to negotiate, communicate, and has a fierce passion to love and serve his clients, each step of the way and beyond, in what is usually the single largest and perhaps most important investment someone will ever make in their lifetime.

As a Real Estate consultant licensed in MD, DC and VA, Jim is not looking for a one-time transaction, but rather aspires to be your trusted advisor who provides personal and professional services for life!

Jim’s clients automatically become members of his exclusive “Client Appreciation Program” in which they receive numerous ongoing services, and fun opportunities throughout the year. And if you need a good service or trades professional, Jim is happy to connect you to his network of business relationships through his extensive business directory. Jim is a long-time “One2One” and now in the next-level “Team Coaching” member of the largest Real Estate business coaching network in North America, (Buffini & Company) and leads a monthly Success Group for regional agents. Jim is also an exclusive member of Dave Ramsey’s Real Estate Entre-Leadership- “All-Access” program, part of which includes a monthly Mastermind network with agents across the country. Additionally, Jim is a certified DRS Agent, and has helped many clients in the Doctor and Medical community, as well as in the law enforcement community. Jim is also a Real Estate network advisor for Gary Clark Incorporated. Through these relationships, Jim is not only a regional, but a national agent, and with his high-level real estate connections across the country, Jim is therefore able to provide enhanced services to his clients who may be re-locating into and out of the area.

Aside from his passion for helping buyers and sellers achieve their home dreams, Jim is a sports enthusiast, enjoys physical fitness, reading, serving in his local church, (has coordinated Dave Ramsey’s “FPU” course), and hanging out with his wife and kids, family and friends.


Joshua D’Ambrosio || Team Agent


Josh is our newest Team Agent and is excited to be part of the great team at Jim Winn Homes. His background in construction and certification as a welder has given him great knowledge in those fields of work. What he loves most about this profession is the opportunity to serve people and help clients find their dream home. He is committed to providing personalized attention, reliable information, and timely communication to meet your unique needs.  Outside of work, Josh enjoys spending time with his beautiful wife and baby girl. He is also an avid sports fan, particularly when it comes to football and baseball. But what truly drives him is his love for people and his passion for serving others. Listening, helping, and providing information are all key aspects of Josh’s approach to real estate. Whether you’re buying or selling, he is dedicated to being there every step of the way to ensure a smooth and successful transaction and is eager to help you achieve your real estate goals.


Tessa Winn || Team Agent & Client Care Director


Tessa is our Client Care Director and a licensed team agent on the JW Homes Team.  Having a natural enthusiasm for loving people from a young age, Tessa received her degree as a Physical Therapist Assistant from Carroll Community College and began a career in Physical Therapy where she could use her gifts of compassion in patient care. Since starting a family with Jim, she has only expanded her capacity and skills in management, diligence, and thoughtfulness in the vigilant care of her family as a stay-at-home mom. Jim and Tessa’s working relationship had its beginnings in college campus ministry where they met, accomplishing common goals as he lead ministry and she provided admin support. They are excited to once again partner together using their time, energy and resources to take client appreciation and care to the next level! Her Client Care Director role is designed to enhance our client appreciation and care with various relational services that go beyond transactional business. Whether it’s popping by with seasonal gifts, coordinating events, or connecting about home improvement needs, she is grateful for the opportunity to serve our clients! Being a licensed team agent also allows her to support Jim on occasion where particular transaction needs may arise.

Tessa enjoys spending time with her family and friends. She loves swimming,  triathlon training, singing in community choir and church worship team, traveling and photography. She find most joy in blessing other people and thrives in connecting with community.


Becca Kless || Executive Assistant


Becca is our Team Executive Assistant. She was born and raised in Montgomery County, Maryland. She met her husband while attending Montgomery College and they got married just days after she graduated from the University of Maryland, College Park. They have four sons aged 10 to 2 years old and life at home is loud and fun! Becca has worked as an executive assistant for nearly two decades in several roles, honing her communication and organization skills, while working behind the scenes to help others’ work shine. She looks forward to helping the Jim Winn Homes Team continue its excellent customer care and professional service.


Stacey Wood || Transaction Coordinator


Stacey is our Team Transaction Coordinator.  She was born and raised in the Pocono Mountains, PA and moved to Montgomery County, MD in the late ‘90s. Stacey and her husband have been married for over 20 years and have 2 wonderful daughters. She and her family bond over activities such as camping, 4-wheeling, and traveling to see friends and extended family back in PA. Stacey comes to us with an expansive professional experience, covering nearly 30 years in various industries including banking/lending and insurance. She is delighted to be a member of the JW Homes Team again and looks forward to serving you.


Anne Tippett || Listing Coordinator


Anne is our Team Listing Coordinator and has served the JW Homes Team for over 4 years. She was born and raised in St. Mary’s County and relocated to Montgomery County over 22 years ago. She developed extensive administrative experience before putting her career on hold to stay at home with her two children. Anne’s background in Quality Assurance lends itself to our detailed home-selling process. In her free time she loves getting back to St. Mary’s and spending time with her family and friends. She enjoys photography, crafting, and relaxing boat rides on the Patuxent River. Anne strives to serve you with exceptional support and integrity throughout the selling of your home.


Shannon Mesmer || Marketing Coordinator


Shannon is our Team Marketing Coordinator.  She was born and raised in Mililani, Hawaii, but now resides in North Carolina with her wonderful husband and four amazing children.  Shannon has more than 30 years of experience in a diverse array of administrative and managerial skills, with a strong proclivity towards customer service and client care.  Spreading joy and helping people has always been an important aspect in her life, both professionally and privately.  Personal interests of hers include reading, creating handmade jewelry, volunteering for school projects, and event planning.  She loves spending time with her family and the beach is her happy place.  Shannon is an enthusiastic member of Jim’s team, and she is committed to assisting you.  Working collectively with the team, she will strive towards providing exceptional service and care to help you achieve your home selling or purchasing goals.