Leonardtown Homes with Ranch/Rambler Style

Leonardtown Homes with Ranch/Rambler Style

Welcome to Leonardtown, Maryland, a picturesque town nestled in the heart of St. Mary’s County. Rich in history and charm, Leonardtown is known for its vibrant community, scenic waterfront, and a delightful blend of small-town living with modern conveniences. As the county seat, it boasts a variety of local shops, restaurants, and annual events that foster a strong sense of community. The town is also home to the historic Leonardtown Wharf, where residents can enjoy leisurely strolls, fishing, or simply taking in the breathtaking views of the Patuxent River.

For those seeking a serene lifestyle in Leonardtown, ranch and rambler-style homes are an excellent choice. These single-story residences are celebrated for their open floor plans, accessibility, and seamless flow between indoor and outdoor spaces. Perfect for families, retirees, and anyone in between, ranch homes offer the convenience of living without stairs, making them a practical option for all ages.

Many of these charming homes come with spacious yards, ideal for gardening or outdoor gatherings, and often feature modern updates that blend classic charm with contemporary amenities. Living in a ranch-style home in Leonardtown means you can enjoy the tranquility of suburban life while still being just a short drive away from the bustling activities of nearby cities.

Whether you’re drawn to the historical allure of Leonardtown or the comfort of a ranch-style home, this delightful town offers the perfect backdrop for your next chapter. Discover the warmth and community spirit of Leonardtown today!

Newest Leonardtown Homes with Ranch/Rambler Style

3 Beds ⋅ 2 Baths

BEST AND FINAL OFFERS DUE BY MONDAY AUGUST 10th at 10:00 AM Owned by the same family since the 1960s, this 3-bedroom, 2-bath rambler has been lovingly maintained and is ready for its next chapter. This one already has the space, setting, and major improvements to make the possibilities exciting. The larger updates have already been taken care of, including a newer roof, siding, windows, new septic (early 2000's) and a 21x15 composite deck overlooking the backyard. The HVAC and furnace have also been serviced annually, allowing the next owner to focus on fresh paint, personal touches, and making the home their own. Inside, the oversized 25x12 owner’s suite includes a private bath and plenty of room for a king-size bed and sitting area. A spacious 35x12.5 addition with two separate entrances offers incredible flexibility for a family room, home office, playroom, guest space, in-law setup, studio, or hobby area. The layout also provides an opportunity to expand the kitchen and create an even larger gathering space. Original HARDWOOD flooring is under the carpet in all three bedrooms, just waiting to be uncovered and restored. Situated on a level, fully fenced lot just under half an acre, nearly every inch of the property is usable. There is plenty of room for pets, gardening, entertaining, outdoor play, or even a future pool. A storage shed and driveway parking for at least five vehicles add even more convenience. Two private community beaches with sweeping view of the Potomac River are just a short walk from the front door, and there is no HOA. Bring your fishing poles, beach chairs, and imagination. This one feels like home!

43927 Lanedon Dr, Leonardtown

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

3 Beds ⋅ 2 Baths

**Seller offering $10,000 in Closing Help** Step into this ONE level, completely renovated home that was stripped down to the studs and everything was replaced from the roof to the floor, new well, and connected to public sewer in 2022. Expand without having to worry about where the septic or septic reserve area is. See and feel the craftsmanship that was put in with wood flooring, stainless appliances, sought after barn type door bedroom closets, Primary step in glass/tile shower, and tiled secondary bath. This is like getting a brand new home at a secondary home price. All of this so close to Leonardtown, the hospital, schools, and shopping. See it today!

23898 Speith Rd, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009

4 Beds ⋅ 4 Baths

Experience waterfront living at its finest in this beautifully renovated home overlooking Saint Clements Bay. Designed to maximize the breathtaking water views, this light-filled home features an open-concept floor plan that seamlessly blends comfortable everyday living with exceptional entertaining space. Offering 4 bedrooms, 2 full baths, and 2 half baths, the home has been extensively renovated from top to bottom with quality craftsmanship and modern coastal finishes. Expansive windows showcase stunning bay views throughout much of the home, while the spacious waterfront deck and extensive waterside patio create the perfect setting for outdoor dining, entertaining, or simply relaxing while enjoying the scenery. The private L-shaped pier provides direct access to boating, fishing, kayaking, paddleboarding, and all the recreational opportunities waterfront living has to offer. Recent renovations include a new central heating, air conditioning, and ventilation system; new plumbing and electrical throughout; a beautifully updated kitchen with new cabinetry, quartz countertops, and brand-new appliances (dishwasher is original); new engineered hardwood flooring, ceramic tile, and carpet throughout; fully renovated bathrooms featuring new vanities, toilets, tubs/showers, and fixtures; a new water heater; repaired and reinforced floor joists, roof joists, and subflooring where needed; repaired foundation; new attic insulation; brand-new siding; a new roof with 50-year architectural shingles; termite treatment; and a crawl space enhanced with a dehumidifier, insulation, and vapor barrier. Outdoor improvements include a new low-maintenance artificial lumber deck with steps leading to the pier, as well as reset pavers with a new setting bed for the expansive waterfront patio and front sidewalk. Ideally located just minutes from Leonardtown Square, this exceptional waterfront property offers the perfect combination of stunning views, extensive renovations, modern amenities, and convenient access to shopping, dining, and local attractions. Enjoy the best of coastal living in a home where every day feels like a getaway.

22393 Saint Clements Ave, Leonardtown

Listing courtesy of Allfirst Realty, Inc.. Contact: 4433201344

3 Beds ⋅ 2 Baths

OWNER FINANCING AVAILABLE, no banks, call for details. Beautifully renovated rambler located in the highly desirable Leonardtown School District, offering the perfect blend of modern updates and peaceful living on almost 1-acre lot. This move-in ready home features 3 bedrooms and 2 full bathrooms, along with a 1-car garage as well as man cave, workshop, or bonus space. The home has been thoughtfully updated with a brand new roof, new windows, new flooring throughout, a fully renovated kitchen with new appliances, and beautifully updated bathrooms, new water heater providing both style and peace of mind. Additional improvements include a new HVAC system to be installed, ensuring comfort and efficiency for the new owner. Enjoy easy single-level living with plenty of outdoor space, ideal for relaxing, entertaining, or future expansion. No HOA. Conveniently located near Leonardtown amenities, shopping, dining, and schools.

21983 Point Lookout Rd, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009

3 Beds ⋅ 2 Baths

THIS PROPERTY IS FOR SALE ONLY AND IS NOT FOR RENT. BEWARE OF SCAMMERS—ANY RENTAL ADVERTISEMENT FOR THIS PROPERTY IS FRAUDULENT. The required verbiage below shall take the place of the MLS Advisory Task verbiage in res.net. This Property was previously financed by a mortgage loan that was insured by the U.S. Department of Housing and Urban Development (“HUD”) and will require disclosure on the MLS. You may use the disclosure language below in lieu of the MLS task requirements issued through RESNET. Disclosure language must be entered in the Agent Private Remarks. If spacing is an issue, you may attach an Offer Instruction document to the MLS along with the First Look Notice of Interest document. No offers will be reviewed unless a buyer has submitted a First Look Notice to you. At a minimum, the first 3 sentences below as italicized should be entered to the Agent Private Remarks section of the MLS with further instruction to read the offer instructions attached in the MLS document section. An Offer Instruction document is attached for your convenience. If using this document insert the Seller’s name per the listing letter and add the RESNET offer fee and offer link from the RESNET MLS tasks prior to loading the document to the MLS. Charming and beautifully updated brick rancher located in the heart of Leonardtown! This single-level home offers 3 bedrooms and 1.5 bathrooms, making it ideal for easy, comfortable living. Recently remodeled, the property features fresh updates throughout, blending classic charm with modern touches. Enjoy a spacious, level lot perfect for outdoor entertaining, gardening, or simply relaxing. The solid brick construction provides timeless curb appeal and durability, while the interior improvements make this home move-in ready. Conveniently located near local shopping, dining, and amenities, this is a great opportunity to own a well maintained home in a desirable area. Don’t miss it!

42249 Saint Johns Rd, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102669005

3 Beds ⋅ 2 Baths

Enjoy peaceful mornings in the 11’ x 26’ sunroom with wall of windows offering unobstructed views of the Potomac River from Piney Point, Virginia shoreline and west to St. Clements Island. End your day with majestic sunsets. A perfect waterfront escape but minutes to Leonardtown! Vintage 1920’s Cottage with all mechanicals, roof, windows, doors updated within the last 10 years but still exhibiting original craftmanship and renovations throughout the years. Livable preserved charm but perfect for an updating to make it your own. Roomy kitchen opens to great room with 9 ft. beamed ceilings, bay window, and a brick fireplace with woodstove all open to expansive sunroom. Master bedroom with large bath with soaking tub, 6’ x 9’ walk in closet and even a bidet. Entrance foyer with laundry area. Second floor 15’ x 7’ loft perfect for extra sleep or rec room. Over 1,600 sq. ft. of finished area plus a newly constructed detached 480 sq. ft. 2 car garage with 2nd level partly finished coach house apartment and 6’ x 10’ covered porch with waterfront views. Apartment is under roof, sided with electrical and plumbing rough-in with over 400 sq. ft. Fully permitted (that’s important). Combined square footage when completed will be over 2,000. Coach House perfect for guests, family, or rental income. Over 100 feet of protected shoreline with 80 ft. pier plus 10’ x 20’ L platform, power boat lift and 1 slip. Nice sized 10 ‘x 21’ deck accessing pier on shoreline. Wooded lot at the end of a dead-end street!

42195 White Point Beach Rd, Leonardtown

Listing courtesy of Franzen Realtors, Inc.. Contact:

3 Beds ⋅ 2 Baths

Fully renovated. Move-in ready. Prime downtown location. Welcome to 41620 Church St — a rare opportunity to own a completely updated home in the heart of Leonardtown at an exceptional value. Step inside to discover brand new vinyl flooring throughout, a stunning kitchen featuring quartz countertops, and beautifully refreshed bathrooms that bring a modern, clean aesthetic to every corner of the home. Outside, enjoy a fully fenced yard surrounding the property — perfect for pets, gatherings, or private outdoor living. The detached two-car garage adds both convenience and versatility, offering space for vehicles, storage, or even a workshop. All the hard work has been done — just move in and enjoy. Located to downtown shops, dining, and local attractions, this home combines lifestyle, location, and value in one compelling package. Homes like this don’t last — schedule your showing before it’s gone.

41620 Church St, Leonardtown

Listing courtesy of Evergreen Properties. Contact:

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