Leonardtown Land for Sale

Leonardtown Land for Sale

Welcome to Leonardtown, Maryland – a charming town that beautifully blends rich history with modern living! Nestled in the heart of St. Mary's County, Leonardtown serves as the county seat and boasts a vibrant community spirit that welcomes newcomers with open arms. With its picturesque waterfront along the Patuxent River, this quaint town offers stunning views and a serene atmosphere that makes it a perfect place to call home.

Leonardtown is steeped in history, with many buildings dating back to the 18th century, including the iconic Tudor Hall and the historic courthouse. The town is not just a glimpse into the past; it thrives with contemporary amenities, including delightful shops, cozy cafes, and a variety of recreational activities. Whether you’re enjoying a leisurely stroll through the charming streets or participating in local festivals, Leonardtown is a community that celebrates togetherness.

For those looking to invest in their future, we are excited to present prime land for sale in Leonardtown. This is a unique opportunity to secure a piece of this picturesque town and create your dream home or a thriving business. With its convenient location, excellent schools, and a friendly atmosphere, the land available for sale is perfect for anyone looking to settle down or expand their investment portfolio.

Don’t miss out on the chance to be a part of Leonardtown’s enchanting community. Explore the possibilities today and discover why so many are eager to call this delightful town home!

Newest Leonardtown Land for Sale

One of only two lots remaining! Breton Knolls is a 24-lot subdivision, conveniently located in Leonardtown, featuring lot sizes from 1 to 7 acres. Bring your own builder or ask us about one of our preferred builders. Breton Knolls HOA is $300 annually with an initial capital contribution of $500 per lot. Please contact us for additional information or to schedule a private showing.

24645 Springhill Ln, Leonardtown

Listing courtesy of Greenmark Real Estate. Contact: 3017055000

One of only two lots remaining! Breton Knolls is a 24-lot subdivision in Leonardtown with 1-7.5-acre lots. HOA of $300 annually with a $500 initial capital contribution.

22501 Bull Rd, Leonardtown

Listing courtesy of Greenmark Real Estate. Contact: 3017055000

Looking for land to build your dream home....well wait no more! This 5.8 acre parcel has been perc tested, recorded, surveyed and even has builder specs for a future home site and floor plans. You can also pick your own builder and get construction started on your new home. Property is currently registered and enrolled in an Agricultural program. Close to schools, shopping and area amenities. Easy drive to downtown Leonardtown where you can enjoy local shops, restaurants and the wharf.

21365 Bogies Ln, Leonardtown

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279

Great building lot in the Leonardtown city limites with water and sewer available. Part of Singletree but no HOA dues. Currently staked for a house location. Property corners are not staked. See map in documents. Located across from the hospital, walking distance to down town.

41650 Miss Bessie Dr, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

Build your dream home in one of Leonardtown's most desirable locations! Welcome to Parcel 323, Tract 2, a newly created homesite just moments from the heart of historic downtown Leonardtown. Perfectly positioned to take advantage of beautiful water views of Breton Bay, this exceptional parcel offers the opportunity to enjoy the best of small-town coastal living. Imagine strolling to Leonardtown's charming shops, restaurants, coffee houses, wineries, and waterfront Wharf, where you'll enjoy year-round events, live music, kayaking, and breathtaking sunsets. Whether you're looking to build your primary residence or a weekend retreat, this property offers an unbeatable combination of convenience, scenic surroundings, and walkable lifestyle. A recent survey has already been completed by the sellers and markers are present and visible. Buyers are responsible for verifying all building requirements, permitted uses, utility connection and development plans with the Town of Leonardtown and the St. Mary's County Permitting Office. Don't miss this rare opportunity to build in one of Southern Maryland's most sought-after waterfront communities while enjoying the charm, history, and vibrant atmosphere of downtown Leonardtown.

Parcel 323 Tract 2 Washington Street, Leonardtown

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

Finding the perfect lot offering a tranquil, secluded setting yet within an easy drive of historic Leonardtown, NAS Pax River, schools, and amenities can be a real whirlwind of an experience! No worries, as this is the ideal opportunity to achieve just that. This 23-acre parcel of raw land offers many possibilities, whether establishing an enduring farmette, subdividing to reap the rewards, or creating the family compound you've all been dreaming of. This beautiful land is conveniently positioned just off Rt. 5, in a prime location between St. Mary's State Park and the charming St. Mary's County seat, Leonardtown. Note that the location is not actually ON Whirlwind Rd; it is best accessed at the end of Redgate Ln. Future potential to create access from both Rt. 5 and Redgate Ln. Call for more details!

Whirlwind Rd, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009

Nestled in the countryside of Leonardtown in St. Mary's County, this 4.11± acre wooded parcel on St. Andrews Church Road is a rare chance to build, invest, or settle into your own recreational retreat. The property already has a previous perc site in place for a conventional septic system. Soil stability testing will be required, but preliminary work points to favorable conditions. Buyers are encouraged to perform their own due diligence. Access comes off Honey Tree Lane. A good portion of the northern section sits flat, making an ideal homesite or recreational area, while the land rises toward the southern end, farthest from the road, topping out at roughly 90 feet in elevation. A small ditch runs through the middle of the property, adding character while supporting natural drainage. A network of trails winds throughout, offering easy access and plenty of room for ATV riding and exploring. The acreage is primarily wooded with a healthy mix of mature hardwoods and softwoods. This is where it gets exciting for the hunters, the property sees high deer traffic, with multiple trails and rubs throughout, and has already produced some nice bucks. Imagine building a homesite where you can walk out your front door and see deer moving through, or hunt right off the porch. That kind of opportunity doesn't come along often. Zoned residential, the property offers flexibility for a future homesite in a convenient Southern Maryland location. Aggressively priced, this is a rare opportunity to secure a 4.11± acre parcel for recreation, investment, or building the home you've been dreaming about.

0 Saint Andrews Church Rd, Leonardtown

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

Discover a prime 15-acre parcel of land, offering a unique investment opportunity with significant potential returns. This property features a serene backdrop of trees and wooded areas, providing a tranquil setting while ensuring privacy. The sloping terrain enhances the natural beauty and could be ideal for various development projects, from residential homes to recreational retreats. The wooded landscape adds aesthetic value. The natural surroundings and potential for development make it a compelling choice for those looking to maximize their investment in real estate. Don't miss out on this opportunity to secure a piece of land with both beauty and potential. 15 Acres in Leonardtown. This could be a great property for the right buyer. Lots of potential, could possibly be sub-divided. Has an old house on property, with failed septic system. (Please do not enter home for your safety)

42700 Moll Dyer Rd, Leonardtown

Listing courtesy of Coldwell Banker Premier. Contact: 5406624500

UNIQUE BEAUTIFUL OPPORTUNITY to Unlock the potential of a lifetime with this rare and spectacular waterfront property! This stunning PENINSULA boasts approximately 1200 feet of waterfront, with its prime location fronting St. Clements Bay with protected coves/creeks on either side. There is some sandy beach on property in one section. This property offers breathtaking views and endless possibilities for waterfront living at its finest. It's a wonderful place to relax, entertain and make wonderful memories in the years to come! Build your dream house and enjoy gorgeous sunsets over the water. With a convenient Leonardtown location, this waterfront gem is a true treasure. Don't wait - seize this once-in-a-lifetime opportunity to own a piece of paradise with gorgeous views all around. There is an old abandoned big house on the property (helps with impervious surface requirements when you decide to build) - PLEASE DO NOT ENTER HOUSE - not structurally sound! Property sold AS-IS!! Schedule your showing today!"

39645 Sweetpea Ln, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

Discover a rare opportunity to create your dream home just moments from the charm and culture of Leonardtown Historic Art District. Ideally situated within walking distance to local shops, dining, the scenic Leonardtown Wharf, and the United States Postal Service. This property offers the perfect balance of privacy and community living. Conveniently located within walking distance of highly rated private and public schools. Whether you're envisioning a custom-built residence tucked away in a peaceful setting or seeking a smart opportunity, this parcel delivers exceptional potential. Previously considered for a single family home with preliminary builder plans already drafted, the possibilities here are expansive. Enjoy the tranquility of your own space while being just outside the vibrant and growing arts and cultural scene of Leonardtown Arts District. This is your chance to secure a prime piece of land in a highly desirable location. where small-town charm meets modern convenience. Mortgage savings may be available for buyers of this listing.

41708 Fenwick St, Leonardtown

Listing courtesy of Redfin Corp. Contact: 3016586186

Discover the ultimate canvas for your vision at this 10.2-acre waterfront parcel overlooking Breton Bay. This rare offering combines natural beauty, privacy, and opportunity—an ideal setting to create your own waterfront retreat. With perc approval already in place, the property is ready for your dream home. The land features a mix of open fields and wooded areas, with views of the bay and abundant wildlife all around, creating a peaceful and scenic setting. For outdoor enthusiasts, this property offers deep water access suitable for larger boats, with easy access to Breton Bay and the lower Potomac River. Boating, fishing, and crabbing are all easily accessible. Located in the desirable Leonardtown area, the property is just minutes from Breton Bay Golf & Country Club and a short drive to Leonardtown Wharf and Town Square for dining, shopping, and local amenities. The property is currently under agricultural assessment and enrolled in the Forest Management Program, providing reduced property taxes. Access to local builders and preliminary pricing information is available to assist with planning and development. A unique opportunity to own a sizable waterfront parcel offering privacy, usable land, and water access.

Ferny Hills Ln, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

6+ acre lot zoned RPD in a prime location with approximately 600 ft of road frontage and high visibility potential. This is NOT currently a residential building lot because it failed a perc test in April 2005. However, the current Comprehensive Zoning Ordinance lists other “potential” uses that may not require on-site sewage disposal. The list includes but is not limited to: Construction Materials and Equipment Storage, Equestrian Facility, Farmer’s Market, Fairgrounds & Flea Markets, Shows and Events, Outdoor, Animal Boarding - Sales & Service, Crop Production and Horticulture, Agricultural Industry - Minor and Roadside Stand. The lot is in the critical area and Flood Zone AE. Potential buyers must conduct their own due diligence and contact St. Mary’s County agencies. Information deemed Reliable but not Guaranteed.

St. Andrews Church Road, Leonardtown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4103940990

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