
Get to know the team
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 hi...
Team listings & sales (417)
For Sale (3)
Address | Bed/Bath | Listing price |
|---|---|---|
![]() 5710 Emory Rd Upperco, MD 21155
| 4 Bed, 3 Bath | $1,000,000 |
![]() 101 Kestrel Ct Gaithersburg, MD 20879
| 4 Bed, 4 Bath | $475,000 |
![]() 10350 Watkins Mill Dr Gaithersburg, MD 20886
| 4 Bed, 3 Bath | $465,000 |
Sold (414)
Address | Sold date | Closing price | Represented | Flag Sale |
|---|---|---|---|---|
| 12/4/2025 | $910,000 | Seller | ||
| 11/25/2025 | $329,900 | Buyer | ||
| 11/21/2025 | $725,000 | Seller | ||
| 11/20/2025 | $595,000 | Seller | ||
| 11/18/2025 | $375,000 | Seller |
Team reviews (75)
Write a review- Highly likely to recommend||5.05.0
12/1/2025 - scottchjones
Sold a Single Family home in 2025 in Clarksburg, MD.Local knowledgeProcess expertiseResponsivenessNegotiation skillsWe've known Jim for many years and he led us well through what was an incredibly difficult selling market. He's seen it all through many years of market experience and didn't flinch when challenges came. Despite the difficult market, he was able to s... - Highly likely to recommend||5.05.0
11/20/2025 - lisa karam9535
Sold a Townhouse home in 2025 in Gaithersburg, MD.Local knowledgeProcess expertiseResponsivenessNegotiation skillsIt was fantastic working with Jim and his team! Everyone was so engaged, helpful, and so patient with me. I especially liked how they kept me up to date with all the showings as soon as the house went to market. I felt very much that we were all in t... - Highly likely to recommend||5.05.0
9/9/2025 - fangelying
Sold a Townhouse home in 2025 in Clarksburg, MD.Local knowledgeProcess expertiseResponsivenessNegotiation skillsJim’s team makes the process of selling a house much less stressful. They are honest, committed, encouraging, professional and hardworking. I simply can’t say enough good words about them! - Highly likely to recommend||5.05.0
7/25/2025 - Scott Greenberg
Bought and sold a Single Family home in 2022 in Aspen hill, Rockville, MD.Local knowledgeProcess expertiseResponsivenessNegotiation skillsJim is an amazing realtor and is a wealth of knowledge and support. He's helped us purchase 2 single-family homes and sell one. I highly recommend Jim for anyone looking for an all-star agent. - Highly likely to recommend||5.05.0
7/25/2025 - armandosedojr
Sold a Townhouse home in 2025 in Laurel, MD.Local knowledgeProcess expertiseResponsivenessNegotiation skillsJim did a great job helping us sale our home. His knowledge, expertise, and his team were excellent in the whole process. They were attentive and helpful through the entire process.
Service areas (30)
- Fairfax, VA
- Falls Church, VA
- Frederick, MD
- Olney, MD
- Silver Spring, MD
- Columbia, MD
- Edgewater, MD
- Montgomery Village, MD
- Severn, MD
- Urbana, Frederick, MD
- Damascus, MD
- Clarksville, MD
- Odenton, MD
- Germantown, MD
- Laytonsville, MD
- Mount Airy, MD
- Rockville, MD
- Wheaton, Silver Spring, MD
- Elkridge, MD
- Bethesda, MD
- Washington, DC
- Gaithersburg, MD
- Potomac, MD
- Woodbine, MD
- Clarksburg, MD
- Ijamsville, MD
- Manassas Park, VA
- Monrovia, MD
- Glenmont, Silver Spring, MD
- Chevy Chase, MD














