67 properties for sale in Holly Oaks, District 3 Leonardtown St Mary's County Maryland

Welcome to this lovingly maintained 3-bedroom, 2-bath rambler with a full basement, where pride of ownership is evident from the moment you arrive. Built in 1962, this well-constructed home showcases the quality craftsmanship of its era and has been thoughtfully cared for over the years. Freshly painted and professionally cleaned, the home is move-in ready while offering the perfect opportunity to add your own personal style. The inviting living room opens to a bright sunroom, creating a peaceful space to enjoy your morning coffee, read a book, or simply take in the views. To ensure this space is ready for its next owners, an Andersen window in the sunroom is currently being replaced. The full basement adds valuable living and storage space, featuring a partially finished area that's perfect for a recreation room, home office, or home gym, while the unfinished utility section provides ample room for storage, projects, or a workshop. One of the property's standout features is the impres

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 butlers 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

Welcome to this beautifully updated home in popular Breton Bay! As you arrive, you'll appreciate the landscaping leading to the home, which was completed in the fall of 2025. Upon entering, you're greeted with wood floors and sunlight that floods the space thanks to the large windows across the front of the home. The open floor plan allows the living room to flow seamlessly into the dining area and into the kitchen. The kitchen was completely renovated in 2025 and features quartz counters, soft close cabinetry, tile floors, and stainless appliances. There's plenty of storage and counter space for easy meal prep and entertaining. For the grilling enthusiasts, a screened porch is a few steps away from the kitchen making it convenient for grilling and outdoor dining. As you progress down the hall, you're greeted with two spacious bedrooms, and a hall bathroom that was renovated in 2024 with a timeless design. At the end of the hall is the generous sized owners bedroom, complete with multi

December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! Homesite 157 Madison D1: 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

NEW CONSTRUCTION, ready and completed in desirable Mechanicsville! This beautiful home offers an open-concept floor plan with the living room, kitchen, and dining area flowing seamlessly together, making it perfect for everyday living and entertaining. The kitchen is a standout with a center island, gorgeous granite countertops, custom cabinetry with plenty of storage, and stainless steel appliances. Beautiful flooring flows throughout the home, paired with tasteful colors and finishes that give the space a fresh, modern feel. The home features 3 spacious bedrooms and 2 full bathrooms, including a primary suite with a private bathroom and beautiful tile work. The hall bathroom also offers stylish tile details, adding to the quality and charm throughout the home. Additional features include a charming front porch, a large 2-car garage, and an unfinished basement with endless possibilities. Whether you need extra storage, a home gym, future living space, or a recreation area, the basemen

Beautiful Southern Maryland Coastal Retreat. Gracious and sophisticated. Elegant details throughout this incredibly, well-appointed home. Custom barrel ceiling and stained glass make a beautiful statement in the grand entry foyer. Inviting Family Room with serene water views. Newly renovated gourmet chef's kitchen is a coastal lovers dream. Enjoy sub-zero Wolf and Cove stainless appliances throughout. Custom white Cabinets and a blueberry hued Island grace this light and bright kitchen. Creamy quartz counter-tops and backsplash w/ Kohler ceramic and cast-iron sinks. Custom lighting and hardware. So very pretty with island seating and prep sink, all with water views. Kitchen and casual dining access to the large waterside screened porch for that morning coffee or evening dinner. Enjoy the walk-in pantry and open sight lines from the kitchen through the casual dining spaces and into the expansive Family Room. Warm Brazilian Cherry hardwood flooring flows through most of this spectacular

Pending*. Homesite 154 Oakley D1 TO BE Built Builder Incentive $12,500 in Closing Help with use of preferred lender and title company. Photos shown are representative and intended to illustrate a similar finished townhouse. 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

The value is in the land. 1.36 Acres in a rural setting with onsite utilities (private well & septic, electric). The property boasts a level lot with mature trees. Live in the mobile home while you begin the process of building your dream home. Or continue to use the mobile home, currently under a month to month lease, as income potential. Note: Government backed loans may not support purchase of the mobile home as a residence

New price $524,900! If youve been waiting for the right opportunity to make your move to Breton Bay, this could be the one. Theres something special about living in Breton Bay. Its the kind of neighborhood where you can come home at the end of the day, leave the traffic behind, and actually enjoy where you live. Tucked away on a quiet cul-de-sac with virtually no through traffic, this home gives you that peaceful, established-neighborhood feel while keeping you close to everything that makes Leonardtown such a great place to call home. Imagine spending summer days near the community beach and pier, enjoying the waterfront, heading out for a round of golf, or meeting friends for dinner in Leonardtown Square. Restaurants, shops, local events and everyday conveniences are just minutes awayand for those working at PAX River Naval Air Station, you can enjoy the Breton Bay lifestyle without giving up a convenient commute. And when you get home? Theres plenty here to love. This beautifully ma

Beautifully renovated and privately situated on 3 wooded acres, this move-in ready 5-bedroom, 3-bath home offers the perfect blend of modern updates, generous living space, and peaceful Southern Maryland living. Thoughtfully renovated from top to bottom, nearly every major component has been updated, allowing you to move in and simply enjoy your new home. The heart of the home is the beautifully renovated kitchen featuring modern finishes, stylish cabinetry, and functional workspace for everyday living and entertaining. Rich hardwood flooring flows throughout the main living areas, while the renovated bathrooms, fresh finishes, and thoughtfully designed spaces create a bright, welcoming atmosphere. The spacious floor plan offers room for everyone, with five bedrooms and multiple living areas that easily accommodate entertaining, working from home, hobbies, or multigenerational living. The finished lower level provides additional flexible space for a recreation room, media room, home gy

New Single-Family Home Opportunity in Meadows at Town Run II! Welcome to Lot 3, featuring Quality Built Homes Fenwick Model. A beautifully designed to-be-built home offering 3 bedrooms, 2.5 baths, and the chance to get in early and personalize select interior finishes, fixtures, and colors depending on construction timing. The Fenwick offers a smart, comfortable layout with a spacious family room, kitchen and breakfast area, 9-foot ceilings, granite/quartz countertops, 42-inch cabinets, stainless steel appliances, and Quality Built Homes signature craftsmanship throughout. Upstairs, the primary suite features a private en suite bath with dual vanities, soaking tub, and QBHIs Deluxe Shower. Two additional bedrooms, a full bath, and second-floor laundry complete the upper level. Meadows at Town Run II is one of Leonardtowns newest opportunities, with only 12 single-family homes planned in this section. Planned amenities include a Rec Center with game room, yoga studio, gym, common area,

Located in the highly sought-after Society Hill community, this home offers close proximity to the water with a partial view of Breton Bay. Just one street from the members-only beach access, you'll enjoy exclusive community amenities including a picnic pavilion, fishing pier, and playgroundperfect for embracing the waterfront lifestyle. The home was extensively remodeled in 2008 with quality upgrades that include new siding, double-hung windows, gutters with leaf guards, and a beautifully updated kitchen. The kitchen features custom wood cabinetry by Miller Cabinet Makers, granite countertops with a breakfast bar, making it ideal for both everyday living and entertaining. The roof was replaced in 2020 for added peace of mind. Inside, you'll find wood floors throughout much of the home, a warm and inviting family room highlighted by a brick fireplace with a gas insert, and custom built-in bookshelves in both the family room and dining area that coordinate perfectly with the kitchen cab

Limited New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 5, featuring Quality Built Homes Bell Floorplan. A 4-bedroom, 2.5-bath single-family home with a smart layout, rear-load garage, and flexible living space. This floorplan offers the convenience of a main-level primary bedroom with a private en suite bath, plus three additional bedrooms upstairs. The main level is designed for everyday living with comfortable gathering spaces, an open flow, and room to make the home your own. Meadows at Town Run II is one of Leonardtowns newest opportunities, with only 12 single-family homes planned in this section. Enjoy convenient access to Duke Elementary, the Leonardtown Library, Downtown Leonardtown, shopping, dining, parks, and commuter routes. Planned amenities include a Rec Center with game room, yoga studio, gym, common area, and pool to be built in 2027, plus tennis/pickleball courts and walking trails. Estimated delivery for early 2027. Final timing dependent on contr

New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 4, featuring Quality Built Homes Mattingly Model. A 4-bedroom, 2.5-bath single-family home with timeless curb appeal, smart design, and room to grow. The main level offers an open and comfortable layout with a spacious family room, kitchen, breakfast area, formal dining room, and living room. Upstairs, the owners suite includes generous closet space and a private bath, with three additional bedrooms, a full bath, and convenient second-floor laundry. Estimated delivery 2027. Final timing dependent on contract date, selections, permitting, and builder construction schedule. Builder incentive available! Quality Built Homes, Inc. Is offering $15,000 in closing help when buyers use QBHIs preferred lender and one of their trusted title companies. Quality Built Homes, Inc. S model home at Meadows at Town Run II is open Thursday through Sunday from 11 AM to 4 PM. Schedule an appointment today to learn more about Homesite 4, av

Welcome home to this beautifully maintained rambler that is truly move-in ready! From the moment you step inside, youll appreciate the bright, airy feel, neutral colors, and pride of ownership throughout. The open floor plan features a gorgeous gourmet kitchen with plenty of space to gather, plus a massive pantry that provides incredible storage. The thoughtfully designed split-bedroom layout offers privacy, with the spacious primary suite tucked away on one side of the home. The primary retreat features a large bedroom, beautiful bathroom, and an oversized walk-in closet. Conveniently located just off the primary suite is a laundry room that also functions as the perfect mudroom. The additional bedrooms are located on the opposite side of the home, creating a comfortable and functional layout. The finished lower level offers even more living space with a full bathroom and a large recreation/movie areaperfect for entertaining, relaxing, or hosting guests. There is also a big unfinished

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. Marys Countys 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 a

Pending. *. Homesite 159 Oakley D1 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