We analyze thousands of real estate agents in Leonardtown and nationwide to find you proven local professionals, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for July 2026. *
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
Information and statistics on the latest trends in the Leonardtown real estate market. *
Apr 1, 2026 - Jun 30, 2026
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Apr 2026 - Jun 2026).
Leonardtown’s rolling three-month numbers show a pickup in activity, with active listings up more than 50% year over year and new listings rising by about two thirds. Homes sold have also climbed sharply compared with a year ago, and pending sales are higher too, signaling stronger contract flow through the market.
Price trends are moving in a different direction, as the typical home value is down about 16% from a year earlier and median list prices have fallen more than 20%. Even with that pullback, the average sale-to-list ratio is still near 100%, and roughly 41% of recent sales closed above list price, indicating that well-positioned homes can still attract strong offers.
Conditions have tightened considerably despite softer prices, with months of supply at about 1.2, versus much higher levels seen in prior years. Homes are taking around 41 days to sell on a typical basis, only slightly slower than a year ago, which points to steady, not frantic, pacing for both sides of the transaction. Buyers and sellers who want to navigate these shifting dynamics can use Agent Pronto to connect with a local Leonardtown agent who understands this data and can advocate for their needs.
Leonardtown offers residents a close-knit community with historic charm, scenic waterfront parks, a thriving local scene, and convenient access to shops, schools, and outdoor recreation.
Leonardtown offers small-town scale with everyday convenience, anchored by a historic downtown and easy access to larger employment centers across St. Mary’s County. Residents appreciate walkable streets, a strong school presence, and a setting that keeps daily errands close to home.
The town’s core surrounds Leonardtown Wharf Park, where a waterfront playground, kayak access, and seasonal events bring the community together. Nearby, the Port of Leonardtown Public Park offers a quiet spot for paddling and picnics along McIntosh Run. Local dining options, including stops along the Leonardtown Arts & Entertainment District, make it easy to meet friends after work or enjoy a weekend meal without a long drive.
Families value educational options such as Leonardtown High School and the Leonardtown Library, both central to day to day life. Healthcare is close at hand through MedStar St. Mary’s Hospital, an important benefit for all ages. Commuters heading toward Lexington Park or the broader Southern Maryland region find practical routes to major employers, while still returning to a quieter home base.
Whether you are relocating to Leonardtown or planning a move across town, a local real estate agent who understands neighborhoods, schools, and traffic patterns can simplify every decision. Agent Pronto connects buyers and sellers with knowledgeable Leonardtown agents who reduce stress and keep your move on track.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“I did a big move from a different state, totally different process pace and Kerry guide me, supported me and held my hand to make it seamless; without her help I don’t know how I would navigate until happily receive my property keys. Working with Kerry is not like any realtor is like a friend that sees what you can’t due the overwhelming process. I highly recommend her”
“It was my pleasure working with you Daniel. You listened to my concerns and responded positively. Thank you”
“Awesome service”
“Nicki has been such a blessing to my family throughout our real estate journey. She helped us buy our very first home, guided us through selling it, and then walked with us every step of the way as we purchased our beautiful new-build home. Through every milestone, she was patient, knowledgeable, responsive, and always had our best interests at heart. She made what could have been stressful feel manageable and was always there to answer questions and offer reassurance. I’m incredibly grateful for her dedication and support, and I truly can’t imagine going through this process with anyone else. If you’re looking for a realtor who genuinely cares about her clients, Nicki is the one.”
“Working with Boris in DC was an outstanding experience from start to finish. He was knowledgeable, responsive, and truly understood the DC market. Throughout the entire process, he made us feel informed and supported, always going above and beyond to answer questions and advocate for our interests. His professionalism, honesty, and attention to detail made what could have been a stressful experience feel smooth and manageable. I would highly recommend Boris to anyone looking to buy or sell a home in the DC area.”
“Working with Makeda Phillander to sell our home in Maryland was truly a great experience. From the beginning, she was professional, knowledgeable, and very responsive, which made the entire process feel much less stressful. She guided us through every step, from pricing the home correctly to handling showings and negotiations, and we always felt confident that everything was being managed the right way. What we appreciated most was her patience, honesty, and the genuine effort she put into making sure the sale went smoothly. We're very grateful for her support throughout the process and would absolutely recommend her to anyone looking to sell their home.”
“Highly professional, very imformative on locations and specifications that would fit the needs of my family. Was able to respond to me during my wild hours of work. She knows her stuff and she can get the job done. Highly highly highly recommended.”
“Pam is the epitome of professionalism and honesty. She operates with respect and integrity. She's incredibly well informed very balanced and measured in how she approaches things. She's always looking for solutions and a win-win outcome.”
“Bob's professionalism, knowledge, and patience exceeded my expectations. I highly recommend Bob for your next move.”
“She is an awesome real estate agent We would not hesitate to recommend her to multiple clients, She is a very understanding and patient person. We do love our new home ,the right one did came ..we would work with her again and again.. Thank u miss Kay.. We appreciate you !!”
“After speaking with Tyrone, it's clear he possesses the experience, expertise, local market knowledge and professionalism I was looking for in a realtor. Throughout the entire home buying process he patiently listened to me and quickly understood what my needs were in terms of amenities, community, location, proximity to work, and convenient access to shopping, dining entertainment, etc. And when it came to preparing and presenting our offer, it was collaborative because he valued my input! He had the foresight to establish rapport and an open line of communication with the listing agent early on in the negotiation phase, which helped tremendously! Aside from being a top tier real estate professional, Tyrone is good people...he's an honest guy and his integrity is beyond reproach!!! I recommend him highly, without reservation.”
“The service was great, and for the agent, you couldn't ask for anyone better.”
“Ms. Brenda made working with Century 21 such a pleasant experience. My family and I cannot thank her enough for the outstanding job that she did. From the beginning of the process Ms Brenda went above and beyond to make sure everything went smoothly. She took the time to understand our goals, developed a strong marketing strategy and showcased our home beautifully. Her communication skills and patience were one of the things that really stood out for us. She answered all questions with patience and made us feel like we were top priority every single time. If you're looking for an agent who will truly go the extra mile, and really knows their stuff then I wholeheartedly recommend Ms Brenda Burrell. She exceeded our expectations in every way! Thank you again Ms Brenda”
“My agent, Nisha Smithrick, was the ideal agent. We had tried to work with other Baltimore agents over the past year and they were terrible. Nisha was amazing from the get-go. She reached out immediately. She asked questions to understand our specific desires for my son's first home. She presented relevant listing within a day. She made herself available for appointments to fit our schedules. She showed us a great selection of homes. She followed up, gave her honest advice. She then was a great sounding board for creating an offer and negotiating with the seller. She was responsive and proactive through the whole process including to inspections and closing. She answered all our questions thoroughly and quickly. I highly recommend Nisha.”
“I loved John and Susan like they were my own family! Absolutely loved working with them! Communication was great and just the experience from start to finish was amazing! I would highly recommend John to anybody who needs a realtor! Words can't express nor describe what a wonderful experience I had working with John and Susan! They deserve the highest level of appreciation! Thank you for aligning me with them through my sale! The world needs more people like John and his sister Susan in the realtor community! Hugs to them!”
“Mary Ann understood what I wanted and found just the right home! I could not be happier with the price we paid. She helped get us a credit after the inspection showed plumbing issues. I would recommend her to anyone looking for a home.”
“This was my first home sale and Brittney made the entire process stress free! From first walk through to signing she was proactive and kept me in the loop. She always answered any questions I had and was extremely knowledgeable about the market and trends in the area. I highly recommend Brittney!!”
“This is our second time working with Tanya Cunningham and she continues to be incredible in all aspects of real estate transactions. She went above & beyond several times throughout our sale process to make it as easy on us as possible. I want to be like Tanya when I grow up. Would highly recommend to anyone in need.”
“Vicki was excellent. She handled every detail quickly, accurately, and professionally. She was available every time we needed to contact her. We were in Florida during the process of selling our home so Vicki had to handle all details and necessary actions without our help and she did. We are totally satisfied.”
“Jetta was recommended to me by Octavia and I completely see why she came recommended. She took care of my family and I the entire time even through emergency situations we had to deal with outside of the home purchase. Jetta was reliable, communicative and highly supportive every step of the way. She ensured that we had every answer to question we had. Additionally, Jetta kept our interest as a priority and resolved every issue ethically and efficiently.”
There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Leonardtown. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Leonardtown Realtor® or real estate agent today.
We’ll match you with top-rated real estate agents in just about any city—wherever your next move takes you.
