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.

301.221.7679 | jim@jimwinnhomes.com

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 of 6 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- transactionally and relationally. 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, 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” 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 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.


Tessa Winn || Team Agent & Client Care Director

301.802.6775 | tessa@jimwinnhomes.com

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.


Roanna De Spirito || Team Agent/Executive Assistant

301.258.7757 x 358 | roanna@jimwinnhomes.com
Roanna is our Executive Assistant and a Team Agent. She was born in Washington, D.C. and has lived in the Maryland/DC area for most of her life. She has had years of administrative roles; including office management, accounting, and owning and managing a retail business. Roanna loves to spend time with her husband and extended family. She also enjoys working on her home, gardening, photography, and playing with her young Goldendoodle. Roanna is enjoying, and committed to serving Jim’s clients in the process of their buying and/or selling of their homes with integrity, and detail-oriented, administrative support.


Kate Kirkham || Transaction Coordinator


Kate is our team Transaction Coordinator. She and her husband Steve, have 3 daughters and one son ranging in age from 7-18 with their oldest just heading off to Penn State.  Raising her kids has been perfect training for her role as a Transaction Coordinator with lots of multitasking and organization required. Prior to starting to work in the real estate field, she helped run a successful online retail and advertising business from home. She loves working with people and helping them through the sometimes stressful process of buying and selling a home.

Kate loves spending time with family and being outdoors – especially at the beach! She enjoys many outdoor activities like camping, hiking and kayaking. Her favorite thing to do is travel and meet new people and learn about different cultures.


Anne Tippett || Listing Coordinator


Anne is our Listing Coordinator. She was born and raised in St. Mary’s County and relocated to Montgomery County almost 20 years ago. She developed extensive administrative experience before putting her career on hold to stay at home with her two children. Prior to staying home with her children, Anne’s background was in Human Resources and Quality Assurance.  In her free time, she enjoys spending time with her family and friends and loves watching her kids play lacrosse. Some of her interests are boating, photography and crafting. Anne is excited to serve you and help you throughout the home-selling process.


Sarah Jane (SJ) Thomas || Marketing Coordinator

301.956.4018 | sarahjane@jimwinnhomes.com

Sarah Jane is our Marketing Coordinator. She was born and raised in Maryland and is pursuing a B.A. degree in Communication at UMCP with a focus on Film and Digital Media. In her free time, she loves to listen to music and podcasts, cook, video game, study television and film, spend time with loved ones, and pursue creative writing. She looks forward to serving you as a part of Jim’s team.


Tara Owens || Referral Coordinator

301.660.8546 | tara@jimwinnhomes.com

Tara is our Referral Coordinator. She was born and raised in Montgomery County, Maryland, and has 2 beautiful children. Tara comes to us with an expansive professional experience, covering nearly 20 years in various industries. Each industry has allowed her to develop wonderful customer service skills, office management, among many other invaluable skills.  In her free time, she and her family bond over activities such as hiking, biking, and anything else that takes them outdoors. Tara is delighted to be the newest member of the JW Homes Team and looks forward to serving you.