Active - Single Family Residence
$1,750,000
4 beds
2 baths
2,130 sqft
Bayside Road, Leonardtown, MD 20650
haley family realty 
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Welcome to Leonardtown, MD, where your dream home awaits! Explore our extensive listings of homes for sale in this charming Maryland town. Whether you’re searching for a cozy single-family home, a waterfront property with breathtaking views, or a brand new construction, Leonardtown has it all. Our team of experienced real estate agents is here to assist you every step of the way. With affordable options and a variety of amenities to choose from, finding your perfect home in Leonardtown is easier than ever. Start your search today and discover the beauty and tranquility that Leonardtown has to offer. Leonardtown is one of the best places to live in Maryland, boasting a rich cultural experience as the only Arts & Entertainment District in Southern Maryland. From historic sites like Leonard Hall Plantation to vibrant outdoor activities along the Patuxent River, Leonardtown offers an exceptional living experience.
If you’re in the market for a new home, we’ve got you covered. Check out our listing of homes for sale below, and discover the perfect place to make your dreams a reality. Just click the “Request More Information” button when viewing the details of that property. We can provide disclosures, past sales history, dates and prices of homes recently sold nearby, and more.
And, if you haven’t already, be sure to register for a free account so that you can receive email alerts whenever new Leonardtown listings come on the market. Or are you curious about the value of your current home?
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4 beds
2 baths
2,130 sqft
Bayside Road, Leonardtown, MD 20650
haley family realty
6 beds
4.5 baths
5,500 sqft
19700 Mulberry Fields Road, Leonardtown, MD 20650
long & foster real estate, inc.
4 beds
3 baths
2,097 sqft
22393 Saint Clements Avenue, Leonardtown, MD 20650
listwithfreedom.com
2 beds
1 bath
1,018 sqft
20798 Waterside Drive, Leonardtown, MD 20650
re/max one
3 beds
2 baths
1,238 sqft
23581 Belmar Drive, Leonardtown, MD 20650
exp realty, llc
3 beds
2 baths
1,728 sqft
41620 Church Street, Leonardtown, MD 20650
evergreen properties
3 beds
2 baths
1,636 sqft
42195 White Point Beach Road, Leonardtown, MD 20650
franzen realtors, inc.
3 beds
1.5 baths
1,161 sqft
42249 Saint Johns Road, Leonardtown, MD 20650
century 21 new millennium
4 beds
3.5 baths
2,604 sqft
Lot 140 - 23659 Dragonfly Lane, Leonardtown, MD 20650
re/max one
3 beds
2 baths
1,144 sqft
21983 Point Lookout Road, Leonardtown, MD 20650
re/max one
3 beds
1 bath
2,952 sqft
25365 Point Lookout Road, Leonardtown, MD 20650
residential plus real estate services
4 beds
3.5 baths
2,554 sqft
Lot 156 - 23634 Dragonfly Lane, Leonardtown, MD 20650
re/max one
4 beds
3.5 baths
2,571 sqft
Lot 157 - 23640 Dragonfly Lane, Leonardtown, MD 20650
re/max one
3 beds
2.5 baths
1,684 sqft
21113 Arbor Court, Leonardtown, MD 20650
o'brien realty era powered
3 beds
2 baths
2,400 sqft
22405 Hood Lane, Leonardtown, MD 20650
o'brien realty era powered
5 beds
5 baths
5,410 sqft
22856 White Swan Way, Leonardtown, MD 20650
kw metro center
3 beds
3 baths
2,331 sqft
22397 Armstrong Drive, Leonardtown, MD 20650
real broker, llc
4 beds
2 baths
2,474 sqft
40743 Magee Drive, Leonardtown, MD 20650
real of pennsylvania
4 beds
3 baths
2,097 sqft
22393 Saint Clements Avenue, Leonardtown, MD 20650
allfirst realty, inc.
5 beds
3.5 baths
4,051 sqft
23591 Margrave Drive, Leonardtown, MD 20650
re/max one
5 beds
3.5 baths
4,834 sqft
23628 Belmar Drive, Leonardtown, MD 20650
re/max one
3 beds
2 baths
1,632 sqft
23898 Speith Road, Leonardtown, MD 20650
re/max one
4 beds
3.5 baths
2,554 sqft
Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
re/max one
4 beds
3.5 baths
2,554 sqft
Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
re/max one
4 beds
3.5 baths
3,314 sqft
41462 Culpepper Way, Leonardtown, MD 20650
re/max one
4 beds
2.5 baths
2,370 sqft
40777 Center 40 Circle, Leonardtown, MD 20650
century 21 new millennium
5 beds
3.5 baths
2,993 sqft
40115 Combs Creek Way, Leonardtown, MD 20650
century 21 new millennium
2 beds
1.5 baths
1,568 sqft
39534 Potomac Avenue, Leonardtown, MD 20650
o'brien realty era powered
4 beds
2.5 baths
4,836 sqft
23636 Hansel Court, Leonardtown, MD 20650
taylor properties
4 beds
2.5 baths
2,774 sqft
40659 Klear Court, Leonardtown, MD 20650
baldus real estate, inc.
4 beds
3.5 baths
3,690 sqft
41444 Osborne Lane, Leonardtown, MD 20650
century 21 new millennium
3 beds
2 baths
1,667 sqft
18800 Mckays Beach Road, Leonardtown, MD 20650
re/max one
4 beds
2.5 baths
3,072 sqft
42084 Wildflower Drive, Leonardtown, MD 20650
re/max one
4 beds
2.5 baths
3,072 sqft
42108 Wildflower Drive, Leonardtown, MD 20650
re/max one
4 beds
2.5 baths
2,701 sqft
42102 Wildflower Drive, Leonardtown, MD 20650
re/max one
4 beds
2.5 baths
2,976 sqft
42096 Wildflower Drive, Leonardtown, MD 20650
re/max one
Leonardtown is a community as well as the county seat of St. Mary’s County in Maryland. It’s home to about 3600 residents and includes a small historic district, healthcare facilities, and a large public high school. It’s bordered by Holly Oaks to the west, Wildewood to the east, Pawpaw Hollow and Breton Bay to the south, and Oakville to the north, even though it’s quite a way up to the Oakville border along Highway 235.
Centrally located, Leonardtown is a convenient hub of shopping, dining, historical quaint town square, waterfront trail, and winery. It’s close to the Newtowne Neck state park perfect for paddleboarding, row boating, and fixturing as well as the Potomac River, hiking, birdwatching, and hunting.
Leonardtown gets its history as early as the 1650s when the town was originally known as Newtown or Newtowne Hundred. Over the years, people came and went and the historic Leonardtown area remains the only incorporated municipality in St. Mary’s County. The town has been experiencing a renaissance of its downtown district with recent openings of several new restaurants, boutiques, retail shops, and businesses. It has several buildings registered as part of the National Register of Historic Places and is known for its fine dining cuisine, fantastic shops and galleries, and close proximity to exploration recreational activities such as the Leonardtown Wharf, the Port of Leonardtown Winery, the Patuxent Adventure Center, and the Macintosh run water trail.
Get ready for a shopping experience like no other at Shepherd’s Old Field Market, the ultimate one-stop marketplace! With 90 shops and services at your fingertips, you’ll find everything you need and more. Treat yourself to gifts, grab a coffee, indulge in tasty eats, unwind in the beer garden, hit up a yoga or fitness class, spruce up your look at the barbershop, or even get some new ink at the tattoo studio! Don’t miss out on all the fun.
Get a taste of the Salted Scoop! Experience farm fresh ice cream, shakes, and more. Savor every scoop of their hand-dipped, farm-to-cone creations. Treat yourself or your loved ones with gift cards and take-home delights.
Indulge in the Rich Flavors of Heritage Chocolates. Satisfy your sweet cravings with the handmade delights of Heritage Chocolates. Escape to this quaint confectionery in Leonardtown, MD, or conveniently shop their small-batch goodies online. Experience chocolate that’s truly made with love and passion. Join the #heritagehandmade movement today!
Get hooked on Crazy for Ewe Yarns! Since 2004, the shop’s playful sheep-filled windows have been a staple on the square in Leonardtown. Step inside and indulge in a color wonderland filled with luscious textures and a warm community of fellow knitters. From beginner to pro, they offer empowering individual lessons and group classes, plus an array of stylish patterns to show off your handiwork. Experience the ultimate knitting destination with events and classes for enthusiasts of all levels. Come knit your dreams into reality today!
Escape to paradise at Fitzies Restaurant and Pub! Indulge in mouth-watering crabcakes and juicy burgers, paired with classic American cuisine. Enjoy open-air dining with stunning views of the beach at our breezy tiki bar. Arriving by boat? We’ve got you covered! Immerse yourself in the perfect summer vibe with our full-service bar. Paradise is just a reservation away at Fitzies!
The Leonardtown Hamptons is a charming neighborhood in Leonardtown, MD, that is perfect for families and anyone looking to settle down. With its quiet, tree-lined streets and well-maintained homes, the Leonardtown Hamptons is a haven for those seeking a peaceful, safe community. The neighborhood is known for its friendly residents and strong sense of community, making it an ideal place to raise children or retire. From quaint coffee shops and boutiques to family-owned restaurants and parks, the Leonardtown Hamptons has something for everyone. Come and experience the warmth and welcoming atmosphere of this lovely neighborhood in Leonardtown, MD.
Nestled in the heart of Maryland is the charming neighborhood of Chestnut Hills. Leonardtown is proud to boast this welcoming community, complete with well-manicured lawns and the perfect balance between suburban charm and city convenience. With easy access to major highways and all the amenities you could ask for, Chestnut Hills is a place that makes coming home feel like a breath of fresh air. Whether you’re looking to settle down or just starting out, this neighborhood in Leonardtown, MD has something to offer everyone.
Hood Ln is an inviting neighborhood located in Leonardtown, MD. The neighborhood boasts its quiet streets and friendly atmosphere, perfect for those looking for a peaceful place to call home. Hood Ln is situated in a prime location, close to local amenities and surrounded by scenic parks and historic landmarks. Residents of the neighborhood enjoy the benefits of living in a close-knit community while still having easy access to the wider area. If you’re searching for a place to settle down and create lasting memories, Hood Ln might just be the perfect spot for you.
Clarks Rest is one of the premier neighborhoods in Leonardtown, MD. Known for its picturesque streets lined with beautiful homes, this neighborhood offers a peaceful and idyllic living experience. The community is comprised of friendly and welcoming neighbors who take pride in maintaining their properties and fostering a strong sense of community. Residents enjoy easy access to local amenities, including shopping centers, restaurants, and various recreational opportunities. Clarks Rest is a neighborhood that truly embodies the charm and character of Leonardtown, MD.
Fenwick St is a charming neighborhood nestled within the vibrant town of Leonardtown, MD. This quaint community boasts a small town atmosphere while providing residents with access to all the necessary amenities for modern living. Fenwick St is an ideal place for those looking to enjoy the peace and tranquility of a cozy residential neighborhood, yet still be close to the action. The neighborhood is home to a diverse mix of people, from young families to retirees, and offers a range of housing options. Whether you’re looking for a cozy bungalow or a spacious two-story, Fenwick St has something to offer for everyone looking for the perfect place to call home.
Residents are part of the St. Mary’s County public school division and most residents with school-age children are assigned to the Leonardtown elementary school, the Leonardtown middle school, and the Leonardtown high school. These schools receive excellent ratings, scores, and reviews by students and parents alike.
“Leonardtown prides itself on our community, academics, and sports. Leonardtown is a high school with wonderful staff that are willing to provide the best experiences for students. Examples of this would be spirit weeks, lunch activities, diverse clubs, monthly events, clean classrooms, and welcoming spaces for all. There is something for everyone at LHS arts, sports, and much more! WE ARE RAIDER STRONG!” – Leonardtown High School Review
There’s a variety of homes and styles available in Leonardtown with an average home price of about $380,000. 55% of residents own their own homes and there’s a median rent of about $879 as of the publishing of this post in 2020. Home prices are all over the board starting at $120,000 up to $800,000 depending on size, condition, and location. There are several historical homes, fixer-uppers, homes that would make a great renovation project, and brand-new homes. You’ll find a wide range of styles, designs, and prices in this extremely popular town. If you’re looking for homes on the water, check out Foxwell Point that may offer waterfront homes in Leonardtown.
“Leonardtown is a family friendly area with great schools, close to restaurants, fresh produce, and can ride your bike or walk to activities in downtown Leonardtown. Downtown Leonardtown has family events each season. Wonderful place to live!”
“Leonardtown is a welcoming town to live in. Leonardtown is continuing to build. Leonardtown has an amazing waterfront park in down town. Leonardtown has many restaurants, a local winery, kayak launch, and local businesses. Leonardtown is in the process of building a new library.” – Niche.com
You can see that Leonardtown is a wonderful place to call home. It’s not too big, not too small, definitely is its own city in its own right, nestled up against the water, yet minutes to multiple bays, rivers, and surrounding communities and towns in St. Mary’s County. If Leonardtown seems like your neck of the woods, browse available listings on my website for free or simply contact me below to get more information on homes for sale in Leonardtown, a virtual tour, or private showing.