Leonardtown Homes with Pool

Leonardtown Homes with Pool

Welcome to Leonardtown, Maryland – a charming town steeped in history and bursting with vibrant community spirit. Nestled in the heart of St. Mary’s County, Leonardtown serves as the county seat and offers a delightful blend of small-town charm and modern conveniences. With its picturesque streets lined with quaint shops, delightful eateries, and a rich historical backdrop, Leonardtown is the perfect place to call home.

One of the standout features of homes in this area is the availability of properties with pools. Imagine enjoying the warm Maryland summers by lounging by your very own pool, hosting barbecues, or enjoying a refreshing swim after a long day. Homes with pools in Leonardtown not only provide a private oasis for relaxation and entertainment but also enhance the overall lifestyle, making every day feel like a vacation.

In addition to the allure of poolside living, Leonardtown boasts numerous parks, waterfront access, and recreational activities that cater to families and outdoor enthusiasts alike. The community hosts various events throughout the year, from art festivals to farmers' markets, fostering a strong sense of togetherness among residents.

Whether you’re a first-time homebuyer or looking for a serene retreat, Leonardtown’s homes with pools offer the perfect blend of comfort, style, and leisure. Discover the joys of living in this inviting town, where every day brings new opportunities for relaxation and connection. Explore the real estate options in Leonardtown today, and take the first step toward your dream home!

Newest Leonardtown Homes with Pool

5 Beds ⋅ 4 Baths

Welcome Home! A covered front entry and separate covered sitting porch create a charming first impression. Step inside to a two-story foyer with hardwood flooring and elegant moldings that continue into the dining room. To the left, a versatile room is ideal for a home office, library, study, or playroom. The dining room flows through the butler's pantry and adjoining walk-in pantry before opening to the kitchen. A large center island anchors the kitchen, featuring granite countertops, abundant cabinetry, a gas cooktop, and double wall ovens. The kitchen opens to the family room, where a gas fireplace creates a warm and inviting gathering space. Upstairs, the owner's suite features a spacious bedroom, two walk-in closets with custom closet systems, and a private bath with a double vanity, a soaking tub with a tile surround, and a beautifully tiled walk-in shower with dual shower heads. Three additional bedrooms, a full hall bath, and a conveniently located upper-level laundry room complete the upper level. The finished walk-out lower level is designed for entertaining, featuring a spacious recreation room with easy access to the patio and backyard. A fifth bedroom with a walk-in closet, currently outfitted as a fitness room, is complemented by a full bath, offering excellent flexibility for guests, multigenerational living, or a private retreat. An unfinished storage room provides valuable additional storage. As the day winds down, the composite deck offers a peaceful place to relax and enjoy the changing colors of the evening sky. The fully fenced backyard features raised garden beds and generous open space for outdoor enjoyment. Located in the sought-after community of Clark’s Rest, residents enjoy an exceptional lifestyle with amenities that include a pool, clubhouse, playgrounds, tennis courts, sidewalks, jogging trails, and more. Just minutes from downtown Leonardtown, shopping, dining, and the Leonardtown Wharf, this home offers the perfect blend of comfort, convenience, and community. Schedule your private tour today!

23214 Dairy Barn Dr, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

4 Beds ⋅ 4 Baths

IMMACULATE & Impressively Upgrades 4 Bed 3.5 Bath End-Unit Townhome w/ a 2- Car Garage & a Screened in Porch in Clark's Rest! Located in the highly sought-after Clark's Rest community in the heart of Leonardtown, this beautifully maintained end-unit townhome offers the perfect blend of space, comfort, and convenience. Just minutes from historic downtown Leonardtown, Leonardtown Wharf, restaurants, boutique shopping, parks, award-winning schools, and an easy commute to NAS Patuxent River, this home combines modern living with an unbeatable location. Featuring three spacious bedrooms, two and a half bathrooms on the upper level, and a versatile lower level currently configured as a fourth bedroom with its own full bathroom, this home offers exceptional flexibility for guests, a home office, fitness room, or additional living space. The open-concept main level is filled with natural light thanks to the desirable end-unit location. The gourmet kitchen showcases quartz countertops, abundant cabinetry, a large center island, gas cooking, and seamless flow into the dining and living areas, making it ideal for both everyday living and entertaining. The upgraded gas fireplace serves as a beautiful focal point, creating a warm and inviting atmosphere. Retreat to the spacious primary suite featuring a tray ceiling, generous walk-in closet, and an ensuite bath complete with dual vanities, a soaking tub, separate shower, and ceramic tile flooring. The additional bedrooms are generously sized, while the thoughtfully designed laundry room includes a convenient utility sink. Additional features include efficient natural gas heat, central air conditioning, a tankless gas instant hot water heater, ceramic tile bathrooms, an attached two-car garage with a professionally finished epoxy floor, and a large screened porch perfect for enjoying your morning coffee or relaxing at the end of the day. Residents of Clark's Rest enjoy beautifully maintained sidewalks, walking trails, playgrounds, community amenities, and a welcoming neighborhood atmosphere, all within one of Southern Maryland's most desirable communities. This exceptional home offers the perfect combination of style, functionality, and location—an opportunity you won't want to miss.

41379 Margrove Cir, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

3 Beds ⋅ 3 Baths

Experience breathtaking panoramic views of Breton Bay and unforgettable sunsets! Cape Cod-style home featuring 3 bedrooms plus a spacious loft. Designed to maximize the water views, the home offers hardwood floors throughout and an inviting floor plan with a living room, family room, dining room, and breakfast room—all overlooking the bay. Enjoy the expansive 37' x 8' front porch or the equally generous 37' x 8' rear porch, where you can relax and take in the peaceful waterfront scenery. Recent updates include new siding, a new roof, and a new gutter system. The side-load garage includes a staircase leading to a large upper-level storage area. Perfectly situated next to the neighborhood beach and pier, this property offers easy access to the waterfront and outdoor recreation. It's also within walking distance of the Breton Bay Golf & Country Club, where memberships are available for golf, swimming, and dining at the clubhouse restaurant. Whether you're looking for a year-round residence or a weekend retreat, this exceptional home combines stunning views, thoughtful updates, and an unbeatable location in one of Breton Bay's most desirable settings.

40579 Port Pl, Leonardtown

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279

3 Beds ⋅ 3 Baths

Set on a level, open corner lot with a small view of the Potomac River—and best of all, **NO HOA**—this well-maintained split-foyer offers comfortable living, thoughtful updates, and a backyard designed for entertaining. A blacktop driveway provides a clean, finished approach to the oversized two-car garage, which accommodates two vehicles with plenty of additional room. The main level features hardwood flooring throughout most of the space, installed in 2019. The kitchen is appointed with cherry cathedral-style cabinetry, Corian countertops, an L-shaped center island, an Americast sink, and indirect lighting above and below the cabinets. The full suite of stainless-steel appliances includes a refrigerator with ice and water in the door, range, dishwasher, and built-in microwave. Hardwood stairs with white risers and balusters connect the home’s two levels. The foyer welcomes guests with 12-by-12-inch ceramic-marble tile and a fiberglass front door featuring sidelights and decorative leaded glass. The spacious primary bedroom includes a walk-in closet with a distinctive cedar ceiling. Its private bathroom offers a jetted soaking tub and separate shower. The second bedroom features luxury vinyl plank flooring, the third bedroom is carpeted, and the hall bathroom includes a tub-and-shower combination. Downstairs, the finished living area offers luxury vinyl plank flooring and a wood-burning fireplace surrounded by brick painted a stylish red. This level also includes a full bathroom with a tub-and-shower combination, a newer washer and dryer, and flexible space for relaxing, entertaining, working, or accommodating guests. The home is also wired for an alarm system. Outdoor living is a standout feature. A composite deck with vinyl pickets and handrails overlooks the fully fenced backyard, while the patio beneath the deck provides additional covered entertaining space. The backyard also includes a tiki-style entertainment area, a three-year-old 12-by-24-foot Intex above-ground pool, and a very large storage shed offering plenty of room for lawn equipment, tools, recreational gear, and seasonal items. Major improvements include the roof and hardwood flooring in 2019, HVAC in 2017, and water heater in 2015. Only two people have occupied the home since 2015, reflecting the light use and care it has received. With **NO HOA**, a level corner lot, an oversized garage, a blacktop driveway, abundant storage, extensive outdoor amenities, and a glimpse of the Potomac River, this home delivers the space and freedom to enjoy your property your way.

43954 Main Way Rd, Leonardtown

Listing courtesy of Keller Williams Flagship. Contact:

4 Beds ⋅ 4 Baths

Charming Home in Prime Leonardtown Location This inviting home sits in the heart of historic Leonardtown— a highly sought-after community with easy access to schools, the hospital, parks, restaurants, and shops. Inside, an open floor plan with abundant natural light creates a welcoming feel. A flexible main-level room works perfectly as a bedroom, office, or playroom. The separate dining room connects through a butler’s pantry to a full walk-in pantry and flows into a modern kitchen featuring granite counters, upgraded cabinetry, stylish subway tile backsplash, large center island, gas cooktop, double wall ovens, and a premium Samsung Bespoke 4-drawer refrigerator with beverage center. The kitchen flows to an eat-in area and a cozy family room with gas fireplace flanked by beautiful custom built-ins. A powder room completes the main level. Luxury vinyl plank flooring runs throughout the main level and upstairs hallway, with hardwood stairs. Upstairs, the spacious primary suite includes a deluxe bathroom with dual sinks, soaking tub, ceramic-tiled shower, and a large walk-in closet. Three additional generous bedrooms, another full bath, and a sizable laundry room round out the upper level. The finished lower level offers a flex room, family room, full bath, and excellent storage. Outside, enjoy a composite deck, fully fenced yard, and firepit — perfect for relaxing or entertaining. Additional highlights include a 2-car garage and owned solar panels that keep utility bills impressively low. Enjoy resort-style living with neighborhood amenities including a spacious clubhouse, a 3,500 sq ft pool with separate kiddie pool, tennis and basketball courts, playground, and walking trails. Ideal location, thoughtful layout, and move-in ready condition — this home checks every box.

41444 Osborne Ln, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

4 Beds ⋅ 3 Baths

CREDIT FOR REPAIRS!! New Lower Price!!Welcome home to 23636 Hansel Court! This stunning Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Step inside to find gorgeous hardwood floors flowing seamlessly across the main level. The mostly finished basement is an entertainer's dream, featuring a dedicated theater area ready for your custom equipment, a spacious office area, a flexible bonus room, and a fascinating secret room hidden away for ultimate privacy or storage. Basement bathroom rough in ready for your unique finishes. Enjoy peace of mind with a brand-new tankless hot water heater installed at the end of 2025. Outside, the premium, fully fenced backyard boasts a 6-foot white vinyl privacy fence, offering a pristine and secure oasis for pets, play, or relaxing. Don't miss this one-of-a-kind home in a fantastic location! Situated in the highly sought after Leonards Grant neighborhood with tennis court, basketball court, community pool, large green, multiple playgrounds and recreation center. Within walking distance to Elementary School and very close to the amazing Leonardtown Square with restaurants, water views , and shops

23636 Hansel Ct, Leonardtown

Listing courtesy of Taylor Properties. Contact:

5 Beds ⋅ 4 Baths

Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year. Perfectly positioned to capture breathtaking water views, this exceptional property offers a rare opportunity to own a private waterfront oasis with an expansive shoreline along both Breton Bay and Combs Creek, extending all the way to the point of its sandy beach peninsula. Enhanced riprap protection, extensive landscaping, and mature surroundings create a truly unforgettable setting. Enjoy 1,545 feet of bay-front water life. Kayakers, yachters, dolphin enthusiasts, fishers, crabbers, and star-gazers are just a few who may find interest in this exemplary waterfront gem. The centerpiece of the outdoor living experience is the spectacular saltwater pool, thoughtfully designed for both relaxation and entertaining. The saltwater pool is finished with premium Wet Edge Premier Stone and Artistic Paver tiles, (featuring embedded seashells sourced from Miami). The tanning ledge measures approximately 8x16' providing the perfect place to lounge and enjoy waterfront views, while a diving board adds to the fun. A dedicated pool pump house and separate dual pool storage unit with its own half bath supports the pool operation. Water enthusiasts will appreciate the exceptional marine amenities. Walking down the hill from the residence leads to a private boathouse and pier system designed with serious boaters in mind. The pier features new stringers, updated power and water service, two slips including the boathouse, and one open slip, a fish cleaning station, and kayak launch area. Low water depth at the end of the pier averages approximately eight feet, making this deep-water location highly desirable for larger vessels and year-round boating. The boathouse, along with the pier, pool house, and detached garage, are all serviced through a dedicated electrical panel system. Water is also available on the pier. Inside, the home has undergone substantial improvements over the years, including a complete transformation of the kitchen and dining areas, creating a stunning gourmet gathering space that serves as the heart of the home. Updated Andersen windows, updated flooring, fresh interior paint, and a beautifully finished laundry and utility room further enhance the home’s appeal. The impressive enclosed sunroom, encompassing approximately 440 square feet, offers year-round enjoyment and flexible living space while showcasing the property’s incredible waterfront views in all seasons. Additional improvements include HardiePlank fiber cement siding, a whole-house generator capable of operating the kitchen and well systems during outages, and a detached 2.5-car garage with a raised floor to improve site grading. The garage offers exceptional storage and future potential for additional finished space should a buyer desire to build up. The well is approximately eight years old. When drilled, the well and pump were upgraded to provide for the additional water needs of the pool, pier and future lawn irrigation. The laundry and utility area features a Navien boiler installed in 2016, providing domestic hot water as well as support for the home’s heating systems. For added value and future convenience, the sellers are in the process of connecting the property to public sewer, which is available within the property. We cannot wait for you to come see the lifestyle that Combs Creek Way has to offer you.

40115 Combs Creek Way, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

4 Beds ⋅ 3 Baths

Here's your chance to make your new home in Breton Bay! Nestled on a quiet cul-de-sac in the highly desirable Breton Bay Golf Community, this beautifully maintained home offers the perfect blend of comfort, convenience, and Southern Maryland living. Enjoy a peaceful setting with virtually no through traffic, while still being just minutes from the community beach, pier, waterfront access, Leonardtown Square, restaurants, shopping, and PAX River Naval Air Station. This home features a new roof installed in 2026, a high-efficiency oil furnace/hot water system approximately two years old, endless hot water capability, and a transferable warranty on the furnace system. The insulated 2-car garage adds excellent flexibility with its own mini-split system for year-round heating and cooling, a large attic storage area above the garage, and 50-amp RV electrical service. Spacious outdoor living areas provide the perfect setting for relaxing, entertaining, and enjoying the mature landscaping of this established neighborhood. With no HOA, a sought-after golf community location, nearby beach and pier access, and the privacy of cul-de-sac living, this property offers a wonderful opportunity to enjoy the Breton Bay lifestyle. More photos and details coming soon!

40777 Center 40 Cir, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

4 Beds ⋅ 4 Baths

Welcome home to this beautifully refreshed home in the sought-after Leonard’s Grant community! Ideally located on Leonard’s Grant Parkway, this move-in ready home features fresh paint and brand-new carpet throughout, offering a clean, updated feel from the moment you step inside. The thoughtfully designed floor plan showcases beautiful hardwood floors, a gourmet kitchen with abundant cabinetry, a spacious walk-in pantry, and a convenient mudroom just off the rear-entry garage. Adding to the home’s incredible value are solar panels, allowing the current owners to enjoy no monthly electricity bill—an exceptional benefit that provides long-term energy savings. Step outside to your fully fenced backyard, where you’ll find an expansive paver patio designed for relaxing and entertaining. Gather around the built-in fire pit, host summer cookouts, or simply unwind in your own private outdoor retreat. Located in one of Leonardtown’s most desirable neighborhoods, Leonard’s Grant offers outstanding community amenities, including a pool, clubhouse, playgrounds, walking trails, tennis and basketball courts, all just minutes from downtown Leonardtown, restaurants, shopping, and not far from NAS Patuxent River. Move-in ready, energy-efficient, and perfectly located, this home offers the ideal combination of comfort

41462 Culpepper Way, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009

5 Beds ⋅ 4 Baths

Welcome to this home in the desirable Leonard's Grant community, tucked toward the back of the neighborhood and featuring a large fenced backyard and composite deck—perfect for outdoor entertaining and everyday enjoyment. Upon entering, you're greeted by a grand staircase and a front living room with built-in bookshelves that flows seamlessly into the formal dining room and kitchen. The spacious gourmet kitchen offers double ovens, ample cabinetry, and an eat-in area that opens to the comfortable great room with a gas fireplace. The main level also includes a powder room and a convenient laundry room that doubles as a mudroom just off the garage. Upstairs, the generous primary suite features a large bedroom, a private bath with a corner soaking tub and oversized shower, and plenty of space to relax. Three additional bedrooms complete the upper level. The finished basement provides additional living space, including a fifth bedroom, along with abundant unfinished storage space. With no carpet anywhere in the home, this property offers easy maintenance and a clean, updated feel.

23591 Margrave Dr, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009

5 Beds ⋅ 5 Baths

This stunning 5 bedroom home sits gracefully at the end of a cul-de-sac on a private lane in Avenmar; a water oriented community on Breton Bay. Its elegant facade overlooks the lovely landscaped yard. From the gourmet kitchen, wander on to the custom covered rear screened porch (almost 600 sq. ft.) where the morning sun dances across the private backyard and patio. Each spacious bedroom is filled with natural light and overlooks the lush woodland and peaceful yard. The main level welcomes you with gleaming hardwood floors that stretch throughout. Formal living and dining areas are perfect for entertaining plus a dedicated office for quiet work-time. The family room off of the kitchen features a cozy wood burning fireplace as the centerpiece while the gourmet kitchen impresses with its high-end appliances, quartz counters and spacious pantry. The walk-out basement offers a fantastic space for movie night, family fun and projects while ample storage keeps everything organized and out of sight. This home promises to delight the most discriminating buyer.

22856 White Swan Way, Leonardtown

Listing courtesy of KW Metro Center. Contact: (703) 535-3610

5 Beds ⋅ 4 Baths

Welcome to this exceptional home in the sought-after Leonard’s Grant community, where timeless design, quality finishes, and incredible indoor and outdoor living come together. From the inviting front porch to the private, tree-lined backyard, every space has been thoughtfully designed for comfortable living and effortless entertaining. Inside, stunning Tigerwood floors flow throughout much of the home, creating warmth and elegance. The main level features a private office, a spacious formal dining room, and a gourmet kitchen with abundant cabinetry, generous workspace, and a large walk-in pantry. The kitchen opens seamlessly to the bright, welcoming great room, while the spectacular sunroom is filled with natural light and overlooks the peaceful backyard. Step outside to the composite deck, which leads to a beautiful paver patio, offering multiple outdoor living spaces to relax, entertain, and enjoy the fenced backyard that backs to mature trees. Convenience continues with a main-level laundry room located just off the kitchen. Upstairs, the luxurious primary suite is a true retreat, complete with a spacious sitting area, an enormous walk-in closet, and a spa-inspired bath featuring a soaking tub and an oversized walk-in shower. Three additional bedrooms are located on the upper level, including a private guest suite with its own attached bathroom. The upper-level landing, accented by beautiful wood flooring, adds to the home’s open and elegant feel. The finished walk-out basement expands your living space with a large fifth bedroom, full bath, theater room, recreation room, and a wet bar—perfect for movie nights, entertaining, or hosting overnight guests. Walk directly out to the paver patio and enjoy the privacy of the backyard. Call for an appointment today!

23628 Belmar Dr, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009

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