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Jennifer Thomas

Jennifer Thomas

REMAX Executive | Chester
Jennifer Thomas

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About Jennifer

A Maryland native with a love for all things local, Jennifer brings a signature blend of charm, expertise, and Eastern Shore lifestyle to every client experience. Whether she’s cheering on the Baltimore Orioles or the Baltimore Ravens, out on the Chesapeake Bay, or spending time with her 6-year-old daughter, home is always at the heart of everything she does. Armed with a Master’s degree from Towson University and an entrepreneurial spirit, Jennifer launched a successful property management business while still in college—setting the foundation for over 20 years of hands-on experience. She transitioned into real estate sales in 2014, bringing with her deep industry knowledge, sharp investment insight, and a results-driven approach. Jennifer has a particular passion for real estate investing and short-term rentals, achieving Superhost status on platforms like Airbnb. Her clients benefit from real-world expertise that goes far beyond the transaction. And for a truly unforgettable closing experience? Jennifer is a licensed 50-ton Master Captain—so don’t be surprised if your home purchase ends with a celebratory cruise. Around here, she’s known simply as *Captain Jen*.

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Jennifer's properties

Jennifer has 11 properties for sale and sold 35 properties in the last 12 months, showing 4, sorted by most recent activity

SoldJun 23, 2026
$550,000
18 Fallon Dr
Lake Shore MD 21122
3
2
2
Single-Family
Listing courtesy of REMAX Executive | Waynesville and Redfin Corp
Show more detail >
SoldJun 9, 2026
$450,000
729 Ravenwood Dr
Pasadena MD 21060
3
3
2
Townhouse
Listing courtesy of Compass and REMAX Executive | Waynesville
SoldJun 5, 2026
$799,500
528 Warbler Way
Stevensville MD 21619
4
3
4
Single-Family
Listing courtesy of REMAX Executive | Waynesville and Keller Williams Flagship of Maryland
Show more detail >
For Sale
$585,000
11/129 Wheelhouse Way
Stevensville MD 21619
2
3
1
Condo
Listing courtesy of REMAX Executive | Waynesville
 Show all 46 properties
Jennifer Thomas
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