“We used Jimmy to sell our home in St. Mary's County and it sold within a couple of weeks with multiple contracts, all above the list price. The process from contract to settlement was very successful. We have used Jimmy in possible home searches and he has been helpful in offering options that would be useful to seniors. He listens to what you say and follows up. We are happy with his services and we consider him a top-notch realtor in Southern Maryland. You want success, Jimmy Hayden is the agent for you. Thanks Jimmy for all your hard work. You are the best.”

St. Mary's, Calvert & Charles Counties · Est. 2007
Southern Maryland real estate, handled by someone who's from here.
Nineteen years of full-time experience, a lifetime of local knowledge, and a phone that gets answered. Buying, selling, acreage, waterfront, or an estate — Jimmy Hayden will walk you through it.

About Jimmy
Born here. Serving here. Invested here.
I've spent 19 years helping Southern Maryland families buy and sell homes, and a lifetime learning the roads, the neighborhoods, the waterfront, and the people who make this area what it is. That knowledge shows up in the details: which creeks silt in, which builders stand behind their work, and which streets hold value when the market shifts.
My approach is hands-on and direct. You'll get data-driven pricing, honest advice, and negotiation that protects your interests from the first showing through settlement. Whether you're a military veteran coming into the area, a first-time home buyer born and raised here, or an investor looking for your next investment, you'll have one point of contact who picks up the phone.
- 19
- Years of Experience
- Native
- Southern Maryland Born & Raised
- Full-Time
- REALTOR®
- 5.0
- Client Rating
Rooted in Southern Maryland
A local record, not a slogan.
Community serviceYears of volunteer leadership with local youth, civic, and charitable organizations across St. Mary's County.
Local knowledgeFirsthand familiarity with waterfront regulations, zoning laws, septic and well systems, acreage, and the builders who work here.
Range of experienceFirst-time purchases, move-up sales, relocations to Patuxent River NAS, senior living and estate sales, and land.
Serving Southern Maryland
Service Areas
Explore Southern Maryland
Multiple communities, each with its own character, price points, and pace. Every one of them is a place I know from the road, not from a map.

St. Mary's County
Leonardtown, MD
A historic county seat with a genuine walkable square, a waterfront wharf on Breton Bay, well-regarded schools, and a mix of in-town homes, newer neighborhoods, and waterfront estates.
Explore Leonardtown, MD
St. Mary's County
California, MD
The retail and dining center of St. Mary's County, minutes from Patuxent River NAS, with newer neighborhoods, the Wildewood community, and easy access to Route 235.
Explore California, MD
St. Mary's County
Mechanicsville, MD
Northern St. Mary's County living with larger lots, farmland, newer estate neighborhoods, and the shortest drive to Charles County, Waldorf, and the D.C. metro.
Explore Mechanicsville, MD
St. Mary's County
Hollywood, MD
A central St. Mary's County community of wooded residential lots, creekside waterfront on the Patuxent, Greenwell State Park, and a location balanced between Leonardtown and the base.
Explore Hollywood, MD
Calvert County
Lusby, MD
Southern Calvert County between the Bay and the Patuxent, with Chesapeake Ranch Estates, Drum Point, Solomons Island nearby, and some of the region's most attainable water-access living.
Explore Lusby, MD
St. Mary's County
Great Mills, MD
A well-located community along Route 5 and the St. Mary's River, with established neighborhoods, newer townhome developments, and one of the shortest drives to Patuxent River NAS.
Explore Great Mills, MDClient Experiences
Trusted by Neighbors, Proven in Results
Buyers and sellers across Southern Maryland describe the same things: fast responses, clear guidance, caring, and someone who genuinely had their back.
“Jimmy represented us with the listing and sale of our existing home, and purchase of our new home. Throughout the entire process he was extremely responsive, knowledgeable, patient, and handled both transactions with great integrity and professionalism. Born and raised in Southern Maryland, Jimmy is the real deal and can be trusted to handle all of your real estate needs. He loves our community, and is a big supporter and donor of local organizations and charities. I highly recommend his services!”
“What a pleasure to do business with him! Jimmy explained everything in detail and helped us make this experience a smooth process. We had been in our home for 40 years and had no idea what was involved in selling it. Our house sold very quickly due to Jimmy's hard work and advertising. He communicated with us almost daily and his advice was gladly appreciated. I highly recommend him if you are looking to buy or sell your home in the Southern Maryland area!”
“Working with Jimmy Hayden to buy our first home was an amazing experience! He was very responsive and knowledgeable. We appreciated his patience with all our questions and his flexibility with our schedules. Jimmy made a stressful process completely seamless! He offered expert guidance at every step and did amazing during negotiations. He was very quick and efficient, we were able to close on our home in just 28 days! I would highly recommend Jimmy to anyone looking for a dedicated, honest, and hard-working realtor!”
“Jimmy is very knowledgeable about the area and was very responsive to any requests or questions I had throughout the process of buying a house. If you're looking for a realtor in Southern Maryland, you won't go wrong with Jimmy Hayden.”
“After attempting to sell our property last year without success, we interviewed four new realtors and chose to work with Jimmy Hayden of RE/MAX this year. He is always responsive. He was professional in his approach to selling and marketing our property, including setting a fair sales price. He is knowledgeable about how to resolve all issues and complications we ran into during the selling process and even-handed at every point along the way.”
Plan Ahead
Estimate Your Monthly Payment
A quick, honest look at the numbers before we talk. Adjust the inputs to fit your situation.
Estimated Monthly Payment
$2,275
Principal & interest only
- Loan Amount
- $360,000
- Down Payment
- $90,000 (20%)
- Total Interest
- $459,160
Estimates only. Contact a lender for exact figures. Taxes, insurance, and HOA dues are not included.
Let's Talk
Ready to Make Your Move in Southern Maryland?
Whether you're pricing a longtime family home, buying acreage, or just starting to look, you'll get a direct answer and a clear next step.
