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

Exceptional Woodridge model in Grandview Haven available for quick occupancy. This very-well kept home sits further back from the neighboring homes and offers a large front lawn and excellent fully fenced back yard space. 3 car attached garage PLUS 1 car detached garage and shed. Enjoy the remainder of the summer heat while cooling off in the 30x15 in-ground pool w/ diving board. An thoughtful addition, the enclosed/screened poolside cabana can be enjoyed mostly year round, whether to seek the shade in the summer, or enjoy the outdoors in the fall. Inside you'll find a gourmet kitchen with stainless steel appliances, Advantium microwave & wall oven, 6 burner gas cook top, pantry and island with seating space. The light-filled sunroom is 16X16 and adjacent to the kitchen and family room, creating plenty of space to move around with ease while also providing easy access to the back yard. There is a true mudroom off of the garage and a separate office on the main level that is just right

Coming Soon! Nestled on over 3 private acres in the heart of Hollywood, Maryland, this beautifully maintained 4-bedroom, 3-bath rambler offers the perfect combination of peaceful country living and modern convenience. Enjoy the ease of one-level living with a thoughtfully designed floor plan featuring main-level laundry, a spacious open-concept layout, and a large kitchen complete with granite countertops, stainless steel appliances, and abundant cabinet space. The fully finished basement significantly expands the home's living space and has been recently updated with new luxury vinyl plank flooring and fresh paint, creating the perfect area for entertaining, a recreation room, home office, or guest accommodations. Recent updates throughout the home, combined with the exceptional level of care it has received over the years, make this property truly move-in ready. Outside, you'll appreciate the expansive yard, mature trees, and private setting that provide plenty of space to relax, ent

Discover the charm of this beautifully maintained split foyer home in the desirable Gillens Grove community. Built in 1978, this residence offers a perfect blend of classic design and modern comfort, featuring 1,664 sq. Ft. of finished living space. With three spacious bedrooms and two full bathrooms, this home is designed for both relaxation and functionality. The fully finished basement provides additional living space, ideal for a family room, home office, or recreational area. The brick and combination exterior not only enhances curb appeal but also ensures durability. Enjoy the convenience of an attached front-entry garage with space for two vehicles, complemented by a paved driveway that accommodates up to four additional cars. Set on a generous 0.72-acre lot, the property offers ample outdoor space for gardening, entertaining, or simply enjoying the tranquility of your surroundings. This home is perfect for those seeking a peaceful retreat while remaining close to local convenie

Situated on just over 2 wooded acres in Hollywood MD. Top off with a well cared for home featuring three bedrooms, 2 full bathrooms on main floor with living room and dining room plus a huge deck for entertaining and enjoying wildlife. This home meets buyer's main concern-location, location, location plus a turn key move in house! No HOA or fees. Just professionally prepared for a new owner. Could be you do not delay your new home awaits!

Welcome home to this beautifully refreshed home in the sought-after Leonards Grant community! Ideally located on Leonards 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 homes incredible value are solar panels, allowing the current owners to enjoy a minimal electric billan exceptional benefit that provides long-term energy savings. Step outside to your fully fenced backyard, where youll 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 Leonardtowns most desirable neighborhoods, Leonards Grant offers outstanding communit

Welcome to waterfront living, right off Saint Clements Bay. Where beautiful views from every room, over an acre of land and direct water access create the perfect Southern Maryland home. Surrounded by water and designed to take full advantage of its incredible setting, this three-bedroom, two-and-a-half-bath home offers the lifestyle waterfront buyers are searching for. Spend your mornings taking in the peaceful views, your afternoons out on the water crabbing, and your evenings relaxing at home surrounded by the scenery. Water lovers will appreciate the private pier with water and electric, approximately 6 to 8 feet of water at high tide, and a concrete boat ramp, making it easy to enjoy boating, fishing, crabbing, kayaking, and everything that comes with life on the water. A composite deck, open front porch, and massive sunroom provide even more places to sit back and enjoy the lifestyle this home will give. Inside, over 2,500 sqft of space is warm and inviting with new flooring, new

Welcome home to this solid, well-maintained detached Ranch/Rambler nestled on a spacious, level lot in Bushwood. Offering 3 bedrooms and 1 full bath, this home features a newer roof and an upgraded heat pump with central air, providing comfort and peace of mind while leaving room for your personal style and updates. With the major improvements already completed, it's the perfect opportunity to create the home you've been dreaming of. Don't miss your chance to make this charming property your own!

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

Stunning Custom Home with Spacious Living, Energy Savings & Room to Grow Welcome to this beautifully maintained 3,800-square-foot home in the desirable Grand View Haven community. Thoughtfully designed for comfortable everyday living and effortless entertaining, this home offers generous living spaces, quality finishes, and exceptional value. The bright, open floor plan features spacious gathering areas, a kitchen with double ovens, granite countertops, abundant cabinetry and workspace, and large windows that fill the home with natural light. Whether hosting family and friends or enjoying a quiet evening at home, this layout offers the perfect balance of openness and comfort. One of the homes standout upgrades is the beautiful hardwood flooring throughout the entire 4-bedroom upper level, adding warmth, elegance, and lasting value while providing a carpet-free living space thats both stylish and easy to maintain. This is a definite plus for allergy sufferers. The finished lower level p

New 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, multi

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 deckperfect 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 c

Unlock the potential in this 4-bedroom, 2-bath handyman special located in the highly desirable Brenton Bay community of Leonardtown! Perfect for investors, renovators, or buyers looking to create their dream home while building instant equity. The main level features a functional layout with a kitchen, separate dining room, spacious living room, two bedrooms, and a full bathroom. The finished lower level expands the living space with an additional family room, two more bedrooms, and a second full bathroomideal for guests, a home office, or multi-generational living. With great bones and endless possibilities, this home is ready for your personal touches and updates. Fantastic location just minutes from shops, restaurants, schools, and waterfront amenities on Brenton Bay. Don't miss this rare opportunity to invest in one of Leonardtown's most desirable neighborhoods and create lasting value. Property is being sold strictly as-is. Schedule a showing today!

Nestled in the charming sought after Clearfields community, this stunning Colonial blends modern luxury with everyday comfort. Set on a beautifully landscaped 1.22-acre lot, this 4-bedroom, 2.5-bathroom home provides ample space for both relaxation and entertaining. At the heart of the home is a chef's dream kitchen, featuring custom cabinetry, gorgeous quartz countertops, a designer backsplash, stunning lighting, and stainless steel appliances. Loads of natural light flood the cozy two story family room with a floor to ceiling stone gas fireplace, a flex room, formal dining room, powder room, and mudroom complete the main level. Upper level fresh new carpet, primary suite w/ gas fp, large walk in closet, deluxe bath with dual vanities, soaking tub, and ceramic tiled shower. Additional 3 bedrooms and shared full bath Full unfinished basement with rough in for future bath Step outside to your private outdoor oasiscomplete with a refreshing inground pool surrounded by lush greenery, a ba

Experience waterfront living at its best with this beautifully maintained 2-bedroom, 2.5-bath home with a loft, perfectly positioned along the Potomac River just minutes from historic Leonardtown. Whether youre looking for a full-time residence or a relaxing getaway, this property delivers the ideal blend of comfort, functionality, and breathtaking views. Designed for those who truly enjoy life on the water, the home features a private pier equipped with a boat lift and fish cleaning stationperfect for boating, fishing, crabbing, or simply enjoying peaceful days on the river. Inside, youre welcomed by a bright and open layout filled with natural light. The spacious sunroom showcases sweeping water views and creates the perfect space to unwind, entertain, or take in unforgettable sunsets year-round. The open-concept living, kitchen, and dining areas flow seamlessly, making everyday living and hosting effortless. The versatile loft offers additional space that can easily serve as a guest

From its inviting curb appeal to its spacious, thoughtfully designed interior, this stunning brick-front Colonial offers nearly 4,500 square feet of finished living space and is perfectly situated on a private 1-acre corner lot in the sought-after Forrest Farm community. Featuring 5 bedrooms and 3.5 baths, this exceptional home is designed for both comfortable everyday living and effortless entertaining. The main level welcomes you with an inviting foyer, elegant formal dining room, spacious sitting room/formal living room, and a private home office. The impressive two-story great room features a cozy gas fireplace and flows seamlessly into the gourmet kitchen, complete with recently replaced stainless steel appliances, abundant cabinetry, and generous prep space. Upstairs, you'll find spacious bedrooms, including a luxurious primary suite with vaulted ceilings designed as a private retreat. The fully finished lower level adds incredible versatility with a large recreation room, fifth

Stunning Waterfront Opportunity on the Potomac River. Discover the perfect cottage waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront livingwhether its crabbing, fishing, kayaking, or canoeing, this location is an outdoor enthusiasts paradise. Enjoy the sights and sounds of ospreys, fish, and abundant wildlife right from your doorstep. Key features include: Approximate water depth: 2.5 ft at low tide, 4.5 ft at high tide Seawall refurbished in 2020 for added shoreline protection Private pier with an electric boat liftperfect for boating adventures Dont miss this rare chance to own a piece of paradise with endless potential. Whether youre looking for an investment, vacation retreat, or future dream home, this waterfront gem is a must-see! Currently listed on

Welcome to your own private paradise in the highly sought-after Hollywood area, tucked away off peaceful McIntosh Road. Set on nearly 16 scenic acres, this exceptional property offers the perfect blend of luxury, privacy, recreation, and modern convenience. A beautifully landscaped entrance welcomes you home with River Birch, Japanese maples, butterfly bushes, roses, azaleas, hostas, and manicured boxwoods, creating breathtaking curb appeal from the moment you arrive. A spacious paved circular driveway provides effortless access for RVs, boats, trailers, and additional vehicles, making entertaining and everyday living equally convenient. The 3,196-square-foot home features 4 bedrooms, 3.5 bathrooms, an attached two-car garage, and a thoughtfully designed open floor plan enhanced with extensive Apple HomeKit smart home automation. Ring security cameras, lighting, HVAC controls, and garage doors can all be monitored and controlled remotely from your smartphone, offering exceptional comfo

Welcome to Avenmar, where this spacious home is situated on a beautiful lot of over two acres, offering privacy, mature trees, and a peaceful wooded setting. Built in 2002 and largely in its original condition, the home has been well maintained and is ready for its next owner to bring their own style and updates. The main level offers a spacious, open layout with a formal dining room, formal living room, private office, and full bath. The centerpiece of the home is the impressive two-story family room with a gas fireplace and floor-to-ceiling windows overlooking the trees and woods. The kitchen features Corian countertops, solid hardwood cabinetry, generous workspace, and an easy flow into the main living areas. Upstairs, front and rear staircases lead to a catwalk overlooking the family room below. The primary ensuite features a private bath and two generous walk-in closets. Three additional large bedrooms, a full bath, and convenient upper-level laundry complete this level. The fully

2.25% Assumable VA loan & one of the largest lots in Leonard's Grant at. 64 acres! This brilliant Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Lots of fruit trees (Fig, Apple, Mulberry, Dwarf Peach, Pear, Strawberry and Persimmon). Enter to find gorgeous exotic hardwood tigerwood floors flowing seamlessly across the main level into the Kitchen where you will be invited to Andura Max floors. Screened porch to enjoy beautiful sunsets. The finished basement is an entertainer's dream, featuring a dedicated theater area ready for your custom equipment, the spare guest bedroom and a walk-out basement. Enjoy peace of mind with tankless hot water heater. Outside, the premium, fully fenced backyard boasts a 5-foot elegant black aluminum fence, offering a pristine and secure oasis for pets, play or relaxing. Firepit with relaxing patio. Don't miss this one-of-a-kind home in a fantastic location! Situated in the highly sought after Leon

Welcome to this stunning QBHI Annapolis model, perfectly situated on a private 1+ acre homesite offering the ideal combination of space, comfort, and privacy. With 4 bedrooms, 2.5 baths, and an exceptional open floor plan, this home is designed for both everyday living and effortless entertaining. Step inside to find a dramatic two-story family room filled with natural light and anchored by a cozy gas fireplace. The heart of the home is the beautifully appointed kitchen featuring stainless steel appliances, granite countertops, a large center island, abundant cherry cabinetry, a walk-in pantry, and plenty of workspace. The kitchen opens seamlessly to the family room, creating the perfect gathering space for family and friends. Upgraded hardwood flooring flows throughout much of the main level, adding warmth and elegance. The main level also includes a convenient half bath and a versatile guest bedroom, offering flexibility for overnight guests, a private home office, or additional livi

Discover a serene retreat nestled on 15.61 acres of picturesque land, where luxury meets functionality in this stunning ranch-style home. This residence, thoughtfully renovated in 2013, boasts 4 spacious bedrooms and 2 full bathrooms, designed for both comfort and style. The open floor plan seamlessly connects the living and dining areas, enhanced with ceiling fans that create an inviting & farmhouse atmosphere. The heart of the home features a well-appointed kitchen equipped with modern appliances, including a built-in microwave, dishwasher, and icemaker, ensuring culinary convenience. The family room, conveniently located off the kitchen, is perfect for gatherings, while the entry-level bedroom offers flexibility for guests or a home office. Step outside to experience the expansive exterior, complete with multiple outbuildings, including a hay barn with stables, catering to equestrian enthusiasts. The property is fully equipped with horse amenities, including a riding ring and stable

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Discover the charm of this lovely waterfront ranch-style home, located in the Mulberrys on Breton Bay neighborhood. With 2,550 sq. ft. Of living space, this home features four spacious bedrooms and 2.5 bathrooms, ensuring comfort for all. Open concept living on the main floor includes spacious family/dining area, primary bedroom and updated kitchen with custom Woodburn soft close cabinetry, under cabinet lighting, stainless appliances, bar seating and large pantry. Step into the large and inviting main level primary bedroom, where panoramic bay sunrise views greet you each morning. The primary bath is updated with ceramic tiled walk-in shower and large walk-in closet. Enjoy cozy winter evenings by the gas fireplace in the open living area adorned with recessed lighting, custom built-in bench seat cabinetry and solid hardwood floors. Outside, the half-acre lot offers deep water direct access to your private dock with water, electric and boat lift, perfect for boating, fishing, crabbing,

Discover a luxurious lifestyle in this stunning 2023 Colonial home nestled in the desirable Clark's Rest community. This exquisite residence boasts four spacious bedrooms and three and a half elegantly appointed bathrooms, perfect for both relaxation and entertaining. The heart of the home features high-end appliances, including an ENERGY STAR refrigerator and built-in microwave, ensuring both style and efficiency in your culinary adventures. Experience the warmth of the cozy fireplace in the inviting living area, while the partially finished basement offers endless possibilities for customization. Step outside to enjoy the community amenities, including a sparkling outdoor pool and tennis courts, all maintained for your convenience. With a two-car attached garage and a beautifully landscaped lot, this home combines comfort and sophistication. Embrace the exclusive lifestyle that awaits you in this exceptional property, where every detail has been thoughtfully designed for modern livin