Why Choose JW Homes

Our team is relentlessly committed to personal and professional growth & development. You can expect the highest level of client services and accountability because we make the necessary investments in our business. We learn from the best in the industry as it relates to everything from master negotiation skills, team leadership & development, goal setting, and efficient time management, to continually raise our team standards and improve methods to better serve you.  The JW Homes Team is recognized as a Top-Producing team, and received multiple “Washingtonian Best” awards, RE/MAX Mid-Atlantic regional awards, and the prestigious RE/MAX Platinum Award for 8 consecutive years.

Established in 1996 by Brian Buffini, Buffini & Company has world-class coaching and training. Jim, having received personal and professional coaching since 2010, has been a member of the exclusive “One2One” coaching program, and is now part of the newest and premier “Team Leadership” coaching program. Buffini coaching agents consistently produce over 10-15 times the national average. Our success and connections with Buffini & Co puts us in the country’s top 1% of REALTORS in average production volume. Jim is a Buffini & Co certified mentor and has facilitated agent training courses, conferences and regional small groups. 

Jim has been a Ramsey Trusted ELP since 2017 and is a Top 5 Ramsey Trusted ELP Regional Agent, producing double the current national ELP average.  As an exclusive member of the (Dave) Ramsey Trusted “ELP”, he has access to this nationwide network that connects people with the top 10% of producing real estate agents in their area for help with home buying and selling. Ramsey Solutions only endorses trustworthy, high-caliber real estate professionals who are well-respected in their communities, maintain very high standards of service and production, are committed to personal growth and development, and have a demonstrated heart of a teacher.

Jim’s close relationship with Washington Redskins WR Legend Gary Clark, provides our clients with opportunities for NFL Experiences via our exclusive “NFL LEGENDS Network”!


While most real estate agents are primarily focused on trying to find and pay for new leads (cold-calling, farming neighborhoods, purchasing online leads, pursuing FSBO’s and expired listings), we don’t do any of those things, but rather, we devote our time, energy, and resources to serving our existing relationships! We want your experience to be successful, smooth, and stress-free, thus making you comfortable and eager to confidently refer us to the people you care about.

What our clients are saying about working with the JW Homes Team


Our “working by referral” model lays the foundation of becoming your trusted real estate advisor for life. While we certainly hope to initially earn that trust when we are successful in meeting your transactional needs, we also believe in maintaining relationships with our clients long after the transaction and aim to meet your relational needs.


Our team’s combined experience in sales, leadership, vocational ministry, marketing, management, and business administration, has resulted in consistent business growth and production since 2008. With nearly $150 million in real estate sold, we are in a unique position to advise you.


Our exclusive Client Portal is a personalized website where you can view listings, documents, and other information. You will be able to see accurate and up-to-date listing activity that matches the criteria you provide.


Our licensed and accredited home staging partners specialize in staging a home to make it more appealing while still allowing the potential buyers to envision putting their own personal touch on the property.


We are very active in the market and have numerous relationships with service vendors (contractors, electricians, plumbers, etc.) who we are happy to connect to our clients. Because we refer regularly, our clients often get preferential treatment and, at times, special pricing from our preferred vendors.

Through faithfully living out our mission statement and core values, the JW Homes team aspires to set the gold standard in the real estate industry as a team who has a reputation of excellence in how we love and serve one another, our clients, cooperating agents, and all service-related relationships. With trust, skill, integrity, grateful hearts, and humility, we produce highly successful results, including WINNing negotiations, in which all parties mutually benefit. Through our tremendous and enduring impact on each person's life, they will always fondly remember their amazing experience and become loyal, raving fans who refer others to experience the same.
~ Jim Winn & the JW Homes Team

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.


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.


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.

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.


Tessa Winn || Team Agent & Client Care Director

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 finds the 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.

Jim Winn || Principal Agent & Team Leader

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 2 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 – in both transactional and relational ways. Our team mission is “Exceeding expectations through WINNing 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 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 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 RamseyTrusted Advisor, 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. On Saturdays during his kids summer swim season, Jim enjoys serving his local community as the home meet announcer.