Jim Winn

Real Estate Consultant & Owner

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Born in DC and raised primarily in the Montgomery County, Maryland suburbs of Washington, DC, Jim and Tessa Winn, 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-Generation 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.

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Joshua D’Ambrosio

Team Agent

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Josh is our newest Team Agent and is excited to be part of the great team at Jim Winn Homes. His previous background in construction, and his 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 to help clients in finding their dream home. He is committed in dedicating his time and efforts to providing personalized attention, accurate & reliable information, and timely communication to meet your specific or 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.

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Anne Tippett

Listing Specialist

Anne has proudly served the JW Homes Team for over six years, bringing warmth, precision, and a deep commitment to client care. Recently returned to her hometown of St. Mary’s County, Maryland, Anne blends her local roots with extensive administrative experience and a background in Quality Assurance—making her an ideal guide through the detailed home-selling process. In her free time, Anne enjoys photography, crafting, and peaceful boat rides on the Patuxent River. She’s dedicated to providing exceptional support and integrity every step of the way.

Julie Bocatot

Client Care and Marketing Coordinator

With a passion for growth and a commitment to excellence, Julie is a valued member of our team as Client Care and Marketing Coordinator. She supports both client care and marketing initiatives, ensuring that communications and processes run efficiently behind the scenes. Julie’s positive energy, eagerness to learn, and dedication to detail allow her to contribute meaningfully to the team’s success. By strengthening internal operations, she helps provide clients with a seamless and supportive real estate experience.

Jim Winn || Real Estate Consultant & Owner

Born in DC and raised primarily in the Montgomery County, Maryland suburbs of Washington, DC, Jim and Tessa Winn, 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-Generation 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 2 other licensed agents, full-service admin & listing coordinators, 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 WINNing negotiations and outstanding client services.” 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 agent licensed in MD, DC and VA, Jim and team go where our relationships take us. We are not looking for a one-time transaction, but rather aspire to be your trusted advisors who provide personal and professional services for life!

 

Jim’s clients automatically become members of his exclusive “Client Appreciation Program” in which they receive ongoing services and fun opportunities throughout the year. Additionally 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 15+ year member, in “Leadership Coaching” at the largest Real Estate business coaching network in North America, Buffini & Company, and led a monthly Success Group for regional agents for many years. Jim is also an exclusive member of Dave Ramsey’s Entre-Leadership “All-Access” program as one of his Ramsey Trusted Advisors, which includes a monthly Mastermind network with top team leaders 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 also has NFL Football Legends relationships with Gary Clark. Through these relationships, Jim is not only a regional, but a national agent. With his high-level real estate connections across the country, Jim is able to provide enhanced services to his clients who may be relocating into and out of the area.

Aside from his passion for helping buyers and sellers achieve their home dreams, Jim is a non-staff pastor in his local church, a raving sports enthusiast, enjoys physical fitness, reading, has coordinated Dave Ramsey’s FPU course, and he loves hanging out with his wife and kids, family and friends. On Saturday’s during his kids summer swim season, Jim enjoys serving his local community as the home meet announcer.

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.