Jim Winn, REALTOR®
We exist to exceed client 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 || Owner of JW Homes, Inc.

301.221.7679 | jim@jimwinnhomes.com

Born and raised in the Montgomery County suburbs of Washington, D.C., Jim and Tessa, along with their 3 children, have deep roots in this region.

Jim received his Bachelor of Science from Boyce College and completed some graduate studies at Southern Seminary. After moving back home to MD after school, Jim graduated from the Sovereign Grace Ministries Pastors College and then served on staff at Covenant Life Church as Ministry Director in the Singles Ministry for 3 years. While Jim enjoyed working full-time in vocational ministry at Covenant Life, a growing desire to transition into the marketplace led to the eventual career move to full-time Real Estate in 2008.

As the owner of JW Homes, Inc., Jim leads a team that consists of 3 other team members- including a full-time licensed assistant and buyer agent, and a transaction coordinator- 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 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. Through these memberships, 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 Covenant Life Church (including coordinating Dave Ramsey’s “FPU” & “Legacy Journey” courses), and hanging out with his wife and kids, family and friends.

Ashley Collins || Team Agent & Assistant

301.760.6513 | ashley@jimwinnhomes.com

Ashley is a REALTOR® on the JW Homes team and Jim’s full-time licensed assistant and is one of the youngest agents in her brokerage. She is a Filipino-American that was born and raised in Montgomery County, Maryland. Ever since she was a little girl she has had an interest in being a real estate agent. She comes to the team with experience in customer service, business administration (from past positions held in small businesses and in her local church), and possesses her real estate license. Ashley has earned her Associate Degree in Communication Studies at Montgomery College. In her free time, she likes going out with her friends, hiking, and lifting heavy weights. Some of her interests are fitness, sports, beauty, and fashion. Ashley loves working with people and is delighted to serve you and help you throughout the home-buying process.

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.

Kate Kirkham || Transaction Coordinator

240.855.8316 | kate@jimwinnhomes.com

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 || Team Assistant

301.520.7588 | anne@jimwinnhomes.com

Anne is our assistant and newest member of our team. 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.