Leonardtown MD Real Estate & Homes for Sale

Welcome to your new home! This impressive 5-bedroom, 3.5-bathroom residence is a masterpiece of design, offering a spacious and well-thought-out layout. Nestled in a prime location with access to top-rated schools, this property caters to both practicality and beauty. Both HVAC systems have been replaced, roof is only 5 years old, new paint throughout and a new BEAUTIFUL patio!! Key Features: **5 Bedrooms**: Generously sized bedrooms provide comfort and privacy for every family member or guest. **3.5 Bathrooms**: Stylishly designed bathrooms with modern fixtures and finishes add a touch of elegance. **Prime Location**: Conveniently located near essential amenities, shopping centers, and entertainment options. **Top-Rated Schools**: Enjoy the peace of mind that comes with residing in an excellent school district, ensuring a quality education for your children. **Spacious Dining Room**: Host memorable dinners in the large dining room, perfect for gatherings and celebrations. **Great Room**: The great room provides a cozy and inviting space for relaxation and entertainment. **Sunroom as Eat-in Kitchen**: The sunroom serves as a delightful eat-in kitchen, bringing in ample natural light for a refreshing dining experience. **Gourmet Kitchen**: The well-equipped gourmet kitchen boasts high-end appliances, generous counter space, and stylish cabinetry. **Private Outdoor Space**: Retreat to your fenced in backyard, an ideal spot for outdoor activities! **Wet bar in the Basement. Great additional entertaining area! Contact me today to schedule a viewing and envision the possibilities of making this house your home!

Lot 112 New Construction - Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft 4 Bedrooms 3.5 Baths 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 3095 sq ft home offers generous living areas, abundant natural light, and the perfect blend of functionality and style. The main level welcomes you with a finished rec room or optional 4th bedroom, complete with a full bath and access to your backyard-ideal for guests, a private office, or a second living space. The oversized one-car garage and wide driveway provide ample parking and storage options. Available end of March/early April 2026. Upstairs, you'll find 9 ceilings, luxury vinyl plank flooring, and a beautifully appointed kitchen with 42� upgraded maple cabinetry, slide-out dovetail drawers, soft-close features, and granite countertops. The large center island, walk-in pantry, stainless steel GE appliances, and open-concept layout make this a true entertainers dream. The adjoining dining and family rooms lead out to a 14x12 maintenance-free deck overlooking your vinyl-fenced backyard. The upper level includes a luxurious owners suite with a tray ceiling, walk-in closet, and ensuite bath featuring dual vanities and QBHIs signature deluxe tiled shower with bench, dual showerheads, and recessed lighting. Two additional bedrooms, a full hall bath, and a separate laundry room complete the top floor. Additional highlights include: finished and painted oversized garage, smart home technology with touchscreen IQ Pro command center, Skybell video doorbell, and smart thermostat, sodded and landscaped yard, stone-to-grade front (per elevation), concrete front porch, and seamless gutters, 6 vinyl fenced backyard with gate. Community amenities include clubhouse, pool, playground, tennis courts, and pickleball courts.

Homesite 100 Madison D1: *** Mid March Delivery***Builder Incentive $12,500 in Closing Help with use of Preferred Lender & Title. Welcome to Meadows at Town Run.... Leonardtowns Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level townhome offering 2,571 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus a versatile room that can function as a fourth bedroom, guest suite, or recreation room, complete with a full bath and closet. The main level boasts a spacious and open kitchen with white kitchen cabinets, Quartz countertops, subway tile backsplash, black fixtures, a center island, large walk-in pantry, and breakfast nook. The open-concept family room flows seamlessly from the kitchen to a 14x12 maintenance-free deck overlooking a fenced backyard, perfect for outdoor entertaining. Upstairs, retreat to the owners suite with tray ceiling, walk-in closet, and a luxurious Deluxe Signature Shower by QBHI featuring floor-to-ceiling tile, dual showerheads, a built-in seat, ledge, shelving niche, and recessed lighting. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the upper level. Community amenities include sidewalks, a swimming pool, recreation center, pickleball and tennis courts, and playgrounds-all located in the heart of charming Leonardtown, Maryland. Come experience the unmatched quality and thoughtful design that sets Quality Built Homes apart. Schedule your tour today! Photos shown are representative and intended to illustrate a similar finished townhouse.

Homesite 102 Oakley D1*** Late March Delivery***Builder Incentive $12,500 in Closing Help with use of preferred lender and title company. New Construction - Oakley D1 End Unit at Meadows at Town Run II 2,966 Sq Ft 4 Bedrooms 3.5 Baths 1-Car Garage. Discover the spacious Oakley D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 2,966 sq ft home offers generous living areas, abundant natural light, and the perfect blend of functionality and style. The first floor level welcomes you with a finished rec room or optional 4th bedroom, complete with a full bath and access to your fenced backyard, ideal for guests, a private office, or a second living space. The oversized one-car garage and wide driveway provide ample parking and storage options. Upstairs, you'll find 9 ceilings, luxury vinyl plank flooring, and a beautifully appointed kitchen with 42� upgraded maple cabinetry, slide-out dovetail drawers, soft-close features, and quartz countertops. The large center island, walk-in pantry, stainless steel GE appliances, and open-concept layout make this a true entertainers dream. The adjoining dining and family rooms lead out to a 14x12 maintenance-free deck overlooking your vinyl-fenced backyard. The upper level includes a luxurious owners suite with a tray ceiling, walk-in closet, and ensuite bath featuring dual vanities and QBHIs signature deluxe tiled shower with bench, dual showerheads, and recessed lighting. Two additional bedrooms, a full hall bath, and a separate laundry room complete the top floor. Additional highlights include: finished and painted oversized garage, smart home technology with touchscreen IQ Pro command center, Skybell video doorbell, and smart thermostat, sodded and landscaped yard, stone-to-grade front, concrete front porch, and seamless gutters, 6 vinyl fenced backyard with gate. Community amenities include clubhouse, pool, playground, tennis courts, and pickleball courts. Photos shown are representative and intended to illustrate a similar finished townhouse.

Live in this lovely waterfront community. Enjoy Kayaking, Paddle boarding whatever your hobbies are. There is even yoga on the wharf, You can walk to weekend concerts on the square. Leonardtown is a wonderful place to live. How about an elevator? This home has one. Send your groceries up in the elevator. Send you laundry down in the elevator, 5 decks/porches to enjoy outdoor living. Walk to the community park. Everything is right where you need it in this lovely home. A must see.

Experience refined waterfront living in this completely renovated rancher overlooking Saint Clements Bay. Originally built in 1966, this residence has been thoughtfully reimagined from top to bottom with extensive structural, electrical, and plumbing upgrades, blending modern luxury with effortless coastal charm. Situated on a waterfront lot, the property offers its own private L-shaped pier-perfect for boating, fishing, or simply enjoying peaceful bay views. The pier measures 91 x 5 with a 26 x 10 extension and approximately 7 feet of water depth to the decking, complete with a pier shed and brand new stairs leading from the home. The open-concept design welcomes you with sweeping water views the moment you step inside, creating a seamless connection between indoor and outdoor living. This home features 4 bedrooms, 2 full bathrooms, and 2 half bathrooms, offering both comfort and versatility. The primary suite serves as a private retreat with two closets and a spa-inspired bathroom featuring an oversized walk-in shower and double-sink vanity. High-end finishes flow throughout, including brand new engineered hardwood flooring in the main living areas, plush carpet in three bedrooms, and porcelain tile in three bathrooms. The designer kitchen is equipped with brand new quartz countertops, a gas stove with vent hood, refrigerator, dishwasher, wine cooler, and a dedicated coffee and wine bar area-ideal for entertaining or everyday enjoyment. Sliding glass doors and expansive windows frame stunning water views and fill the home with natural light. Outdoor living is elevated with a brand new waterfront deck, fresh siding on the sides and rear, a painted brick front, and a new front door, all enhancing curb appeal and durability. Major system updates include a brand new central AC and heating system, brand new gas water heater, an original heat pump serving the den addition, oil heat, and a fully improved crawl space with a new vapor barrier. The roof was replaced in 2009, along with new double-pane vinyl windows that fold in for easy cleaning. Additional highlights include two sheds, ample interior storage, and two on-property parking spaces. An optional, low-annual civic association fee provides access to picnic and swimming areas, boat ramps, and a playground. Conveniently located just an 11-minute drive to Leonardtown Square, offering a vibrant mix of shopping, dining, waterfront parks, historic charm, and year-round community events. This exceptional waterfront property offers a rare opportunity to enjoy modern luxury, private pier access, serene bayfront living, and close proximity to one of Southern Marylands town centers.

Beautiful 2 story home situated on a professionally landscaped level lot with fully fenced back yard. Home is freshly painted and has newly installed carpet throughout main and upper levels. Roof and gutters were recently replaced in 2025. HVAC has been serviced annually. Upper level has 4bedrooms; 2 full bathrooms and laundry room. Main level consists of living room, dining room, family room with propane fireplace, kitchen with pantry and eating area, half bath, direct access to the 2-car garage, and access to backyard. Lower-level basement is accessed from inside and also has 6-foot-wide areaway leading to the level fully fenced backyard. Backyard is accessible from right side via 4-foot gate and on the left side via 8-foot gate Home is located on cul-de-sac with easy short walk to all restaurants and shops in downtown Leonardtown, College of Southern Maryland, Saint Mary's Hospital and Leonardtown wharf. Excellent condition and ready to move-in. Basement currently has numerous weightlifting gear exercise caution during all showings.

Beautiful Clarks Rest townhome offering three finished levels, a two-car garage, and over 2,300 square feet of living space. The main level features hardwood floors, a gourmet kitchen with granite countertops and 42-inch cabinetry, a separate formal dining space, and a large family room-ideal for both everyday living and entertaining. The fully finished lower level includes a spacious recreation room and a full bathroom, perfect for guests, a home office, or additional living space. Upstairs, the expansive primary suite boasts an en-suite bath with a tiled shower, soaking tub, double sinks, and two generous closets. Two additional bedrooms, a full hall bath, and a conveniently located laundry room complete the upper level. Enjoy outdoor living on the large rear deck with a motorized awning, ideal for relaxing or entertaining.

IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new construction home situated on 1.34 flat acres in rural Leonardtown. This 4-bedroom, 2.5-bath residence showcases a modern design with thoughtful details and high-end finishes throughout. The main level features luxury vinyl plank flooring and a bright, open-concept layout perfect for both everyday living and entertaining. The gourmet kitchen is the heart of the home, boasting quartz countertops, stainless steel appliances, and stunning two-tone shaker cabinetry that combines warmth and sophistication. A spacious center island offers additional prep space and seating, all overlooking the expansive living and dining areas. Upstairs, the oversized primary suite offers a peaceful retreat with a generous walk-in closet and a spa-like en-suite bath featuring dual vanities, a custom tile shower, and sleek black fixtures. Two additional bedrooms, a full bath, and a convenient laundry room complete the upper level. With a two-car garage, no HOA, and a private, wooded setting just minutes from Leonardtowns charming town square, waterfront attractions, shops, and restaurants, this home offers the best of Southern Maryland living. Dont miss the opportunity to make this stunning new home your own.

Welcome to 21345 Fairwood Court! Thoughtfully updated and meticulously maintained, this move-in-ready home in the desirable Leonardtown Farms community offers space, layout, and functionality. With 5 bedrooms on the upper level, 3.5 bathrooms, and generous living spaces on every level, there is room to grow, gather, and truly settle in. Beautiful landscaping welcomes you to the covered front porch and into an open foyer, flanked by a formal sitting room and dining room. A dedicated office provides an ideal work-from-home space and flows into the large family room. The updated kitchen features new Zellige tile backsplash, granite countertops, updated stainless steel appliances, an island with sink, cooktop, built-in microwave, wall oven, and a dinette area. New LVP tile flooring, refinished hardwood floors enhances the main level, and new carpeting has been installed on main level and stairs. The spacious family room with gas fireplace is perfect for cozy evenings. The kitchen opens to an updated patio and fire pit, creating an inviting backyard space for entertaining family and friends. The primary suite offers two walk-in closets, a soaking tub, separate shower, dual vanities, and a private bathroom. The finished lower level provides exceptional flexibility, featuring a large open sitting area, a room currently used as a gym (previously a theater room), an additional flexible room suitable for a bedroom, guest space, or hobby room, two storage rooms and a full bathroom. A covered exterior stairwell provides convenient access to the basement. This one won't last long!

Rare Multigenerational Home in Breton Bay - Two Homes in One! Experience the perfect blend of contemporary design and flexibility in the highly sought-after Breton Bay community. This sprawling 3,464 sq. ft. residence has been thoughtfully reimagined to offer two distinct living experiences under one roof-perfect for multigenerational families, a premium home office suite, or a high-end guest wing. The Main Residence is light, airy, and modern. Step into the main level featuring with hardwoods, vaulted ceilings, and an open-concept living and dining area anchored by a cozy fireplace. The "cottage-core" gourmet kitchen is a chefs delight with custom cabinetry and a charming storage closet the owner's have used for wine storage. The entire top level is the owner's sanctuary as a private retreat featuring an ensuite bath, deep walk-in closet, and an architectural overlook that captures the homes unique character. You'll have room to breathe with the two additional spacious bedrooms and a full bath that occupy their own dedicated level, providing perfect separation for children or guests. The guest suite / secondary residence allows for absolute privacy. With its own private exterior entrance, this fully equipped 2-bedroom, 1-bath wing is far more than an "apartment." It features its own kitchen, living area with a private deck, and dedicated laundry. Whether its for long-term family stay or a premium rental, the versatility is unmatched. There is also value-added peace of mind as the owner's installed a brand new septic system in the fall 2025, which save tens of thousands in future costs. The owner's have freshly updated the home and guest suite / secondary residence with new carpet and paint throughout most of the home and secondary residence. Enjoy access to the community beach, pier, and playground just moments away. There is also a beautiful golf course available to homeowners for an additional membership fee. This isn't just a house; it's a solution for the modern family. Ditch the cramped quarters and discover the space, privacy, and community youve been searching for. Schedule your private tour today-homes with this much versatility are a rare find!

Price Reduced on this beautiful colonial home in the Meadows of Town Run neighborhood in Leonardtown. This home has large 6 ft. windows on the entire main level to allow tons of natural light! A beautiful front porch is a great place to sit and chat with your neighbors and enjoy the peaceful community. The upstairs has 4 large bedrooms, the laundry room, and two bathrooms. The main bedroom suite features a large walk-in closet and a luxury bathroom featuring a soaking tub, huge shower, and two vanities featuring gorgeous decorative tile. The kitchen and family room on the main floor offer a large welcoming space for family and friends with a sliding glass door that goes out to the patio to enjoy the firepit and fenced in back yard. The additional dining room and living room spaces allow you to spread out for large family gatherings. The mudroom joins the garage and is a great space to welcome you home. The basement has a finished studio room for your crafts or hobbies and a large unfinished area for you finish and make it your own.

ð??° Seller is offering a $4,000 concession with an accepted full-price offer! Use it for an interest-rate buy-down, closing costs, or to add your own personal touches. Get ready to fall in love with this wonderful 5BR/3.5BA home in the Leonardtown's Kingston Estates! Set on a peaceful, no-through street and perched on a gentle hill, this home offers great privacy with mature trees and plenty of open yard space. Inside, the two-story foyer opens to a main level with newer flooring, real hardwood floors in the living room, and fresh paint throughout the home. A flexible room with French doors at the front of the house works perfectly as a home office or formal dining room. The eat-in kitchen features granite countertops, a tile backsplash, stainless GE appliances, a Kraus sink, center island, and a spacious pantry. It opens directly to a cozy family room with a wood-burning fireplace-great for gathering. Upstairs, youll find four generously sized bedrooms. The primary suite offers wooded views, a soaking tub, dual sinks, walk-in shower, and a large linen closet. Three additional bedrooms and a second full bathroom complete the upstairs. The fully finished walkout basement adds even more versatility with a fifth bedroom, full bath, wet bar, laundry area, and a fantastic flex room ideal for a gym, playroom, office, or media space. Outdoor living is another highlight. Enjoy the composite screened deck that overlooks a private backyard backing to a Forest Conservation Area. A small fenced section is perfect for pets, and the property includes two great sheds-one heated and cooled, ideal for hobbies or studio use, and a 20â?²Ã?24â?² Amish-built structure with electric and lofts for storage or a workshop. Lovingly maintained by its original owners, the home also includes valuable big-ticket updates such as two high-efficiency HVAC systems (2023 & 2025), an architectural roof (2018), a rebuilt driveway, whole-home filtration system, sump pump with backup, chimney improvements, and updated bath fixtures. With more than 3,500 sq ft of finished space and a welcoming, flexible layout, this home offers comfort, privacy, and long-term value-just minutes to historic Leonardtown, dining, shopping, and an easy commute to PAX River Naval Base. Youll feel right at home the moment you arrive. Come and take a look!

Discover waterfront living at its finest with this charming 2-bedroom, 2.5-bath home with a loft on the Potomac River just minutes from historic Leonardtown. Perfectly designed for those who love life on the water, this property features its own private dock complete with a boat lift and fish cleaning station, making it a dream come true for boaters and anglers alike. Inside, youll find a spacious and inviting layout filled with natural light throughout. The highlight of the home is the Florida room with panoramic river views, offering the perfect spot to relax, entertain, or simply take in stunning sunsets over the water. The open loft adds flexible living space-ideal for a guest area, office, or hobby room. The kitchen and dining areas flow seamlessly for easy living, while two comfortable bedrooms provide restful retreats. With 2.5 baths, convenience is never in short supply. An oversized 3-car garage provides ample storage for your vehicles, water toys, tools, and more-making it easy to enjoy every aspect of the riverfront lifestyle. Whether youre searching for a weekend getaway or a year-round residence, this home blends comfort, charm, and direct river access. Enjoy peaceful mornings, afternoons on the water, and evenings watching the river roll by-all from the comfort of your own home. Dont miss this rare opportunity to own a piece of Potomac River paradise!

Welcome to Historic Mulberry Fields, situated on just under 500 acres of fertile land with a mile-long view of the Potomac Rivers white sand shoreline, is truly one of a kind. As you drive along the cedar-lined driveway, you are transported back in time as the magnificent manor house appears in front of you. It is the only remaining Georgian manor house in St. Marys County today. From the south façade, the magnificent mile-long â??Avenue Field,â? lined with trees stretching to the Potomac River provides a breathtaking panoramic view downhill to the white sandy riverbank. The interior of the manor house is of simple and educated taste. The grand center hall and the 2 front (south) rooms (the great room and dining room) have walls of rectangular raised panels to the ceiling, making it one of the most completely paneled 18th-century houses in Maryland. Throughout the house, many original moldings, doors, and mantels are intact. Air conditioning and heating were added to all rooms. The owners retained an architectural firm and have plans - approved by the Historic Trust - for a renovation that would enlarge the kitchen, the bathrooms and adding another wing to the house on the west side. Flanking each side of the north entrance are 2 historic dependencies, both similar in design. Each is of brick, 2-story in height. They were placed symmetrically north of the mansion, forming a rectangular court with the Kitchen Garden, Bowling Green and Orchard separated by a row of large boxwoods. These buildings were used as service buildings with the East dependency as â??The Kitchenâ? and the West dependency as the â??The Weaving House.â? These structures were used to house slaves, such as cooks, stable hands, waiters, and housekeepers who were tasked with running the household and gave the mansion and outbuildings the appearance of a busy village. â??The Kitchenâ? has been remodeled and now serves as a guest cottage, while the â??Weaving Houseâ? retains its original historic riven clapboard partition walls, floors, doors, and hardware. Next to the 2 dependencies flanking the Manor House are numerous other historic buildings, such as the â??Dairyâ? and the â??Meat/Smoke Houseâ? (both east of the Manor House). Other historic buildings include a Carriage House, a Garage/Tool Shed, an Art Studio, a Pole Barn, a Horse and Cattle Barn, a Tobacco Barn, a remodeled Sheep Barn, 2 Equipment Barns, a Farmhouse, and an old dwelling that could be remodeled and turned into a rental unit. Several buildings were added in the 1930s. These include 6 occupied rental units, incl. 3 units in what was previously the Sheep Barn, a 4-BR Farmhouse, a 1-BR Cottage in the renovated â??Kitchen" and a 1-BR Trailer. Taken together, these currently produce an income of $70,000. Add'l income is provided by leasing the fields for farming and from the U.S. Navy that keeps a navigation signal on the Potomac River. More income can be obtained by renovating some of the existing buildings. With that Mulberry Fields could have a total of twelve rental units. Mulberry Fields was added to the National Registry of Historic Places in 1973. The Maryland Historical Trust Deed of Easement ALLOWS LIMITED INDUSTRIAL OR COMMERCIAL activities to be conducted at Mulberry Fields if the external appearances of its buildings are not altered (please ask for more info). Owners of Mulberry Fields must abide by a Conservation Easement, a Historical Preservation Easement, and three Rd Easements. Appr. 100 acres of land is leased out for farming and 300 acres is forest. This unique historic property is close to Leonardtown, Lexington Park and Solomons Island with numerous historic sites, wineries, antique shops, art galleries and restaurants, Deerfield Airport (private jet) as well as St. Marys County Regional Airport. 1h15 min drive to Washington DC and its major airports - Dulles Intl Airport, and Reagan Natl Airport. MORE IN-DEPTH HISTORY AVAILABLE UPON REQUEST.

Spacious home in desirable Hollywood location. (Abell's Ridge) The main level greets you with hardwood flooring in the Foyer. Large owners suite with two walk in closets. The owner's full bath features tile flooring, a double jetted soaking tub, separate shower. Four car garage with work area of garage heated. New HVAC in 2023. Fireplace has wood stove insert. Unfinished basement . Over 7 acres. This property consists of two lots. You can build a family members house right next door. Contract Fell through, Motivated seller.

Welcome to Bayside Road. Residents of Leonardtown believe this is THE place to live. This is a beautiful, well-maintained waterfront farm that is located a few minutes from historic Downtown Leonardtown. When you enter the property gates, you will see the most beautiful canopy of trees leading you through the whole farm. The Charming Cape Cod house is situated on 48.9 acres of gorgeous land. The house is well-kept with 4 Bedrooms and 2 Baths; a place-to-relax front porch; the master bedroom and the laundry room (washer and dryer included) are on the entry level. Also, a foundation for a 3,000+ square-foot house has been started near the water and has the electric meter installed. A pier on the farm is on the protected Cecil Creek where boaters and non-boaters can enjoy the tranquility and hours of fishing, crabbing, and just enjoying life. If it's hunting you want, many deer, turkeys, ducks and other waterfowls have been sighted on this sportsman's paradise. A 24-Hour Appointment Notice is necessary for all showings. To show/view the house, call the Listing Agent who will schedule an appointment for/with you.

Seller is entertaining offers now. Looking for elbow room? Look no further-this property offers plenty of land! It borders the Potomac River and Poplar Hill Creek, featuring expansive farmland and forested areas. Ideal for outdoor enthusiasts and nature lovers, this unique property offers breathtaking sunsets. Correct acreage is 165 acres. Don't miss out on this unique opportunity.