63 houses for sale in Oakley, District 7 Milestown St Mary's County Maryland

Instant Equity! 5 Bed 3.5 Bath Colonial w/ a fully finished basement and a 2-car garage, boasting over 4500SQFT located in Sought After Neighborhood of Leonard's Grant! Homes with this SQFT at this price point are almost non-existent. Similar homes have sold in this neighborhood for $625,000-$675,000! This home will need some cosmetic repair but is ready to shine again! From the street you are greeted by mature landscaping, a large concrete driveway and a sidewalk that takes you to the front porch. Upon entry you are greeted by a nicely sized 2-story foyer. To the right of the center hall, a living room with a formal dining room situated just in behind it. The kitchen, breakfast area, and large family room encompass the entire back portion of the main floor making this the perfect home for entertaining. A nicely finished hall bath and a large mudroom/laundry room complete the main floor. Upstairs, a very large primary suite is home to a huge walk-in closet and an en-suite bath. The bat

Priced below assessed value! Current VA Loan could be assumable at under 4%. Unique waterfront property wu002F guest house. New dock, wu002F marine grade lumber and stainless-steel fasteners was raised to be higher than the avg. High tide. Enjoy crabbing and sunset views from the dock in spring, summer and fall. Property has 69' of shoreline with 2' at low tide and 4-5' at high tide. Open concept floor plan wu002F lots of light and water views. 2 br, 1.5 bath and bonus roomu002Foffice. Upgraded modern kitchen with stainless appliances, new counter tops and farmhouse sink. Newer, 3–4-year-old wifi connected HVAC and solar panels that are owned and will be transferred at sale. Large, bug free screened porch. The electric bill is only $850u002Fyear (not per month! )for the current owners. The guest house has a spacious living, sleeping, kitchen area, a full bath, a large deck and a new metal roof. New wifi enabled minisplit for heating and cooling. Live a multigenerational lifestyle on th

Just reduced! This home is located in the tucked-away community of Longview Beach at 36797 Ricardo Drive, Bushwood, Maryland, and is currently priced at $340,000.00. Sitting on 10,500 sf. Is just under 1u002F4 acre. This recently updated home with great features for winter is the perfect location for the summer. A new metal roof with lighting rods was installed in 2019, including upgrading installation in the atticu002Fceiling and exterior walls. Home features a renovated eat-in kitchen with custom cabinets, a large kitchen counter area for breakfast, and new lighting that opens into the family room. The kitchen has access to the rear yard, and a covered carport or front porch area completes the living space. This gem is awaiting a new owner to enjoy all the benefits of just a short a quiet haven for all nature lovers to sip your morning coffee and watch the wildlife that passes by. In the early morning, you can take a walk down less than half a mile to the shoreline for some early mor

Priced below tax assessed value, this rare waterfront retreat on beautiful White’s Neck Creek offers a renovated guest house, private dock, and true Southern Maryland charm. Set on over half an acre in the established River Springs waterfront community, 37526 River Springs Road offers the kind of lifestyle buyers wait years to find: peaceful water views, navigable creek access, private outdoor space, and a move-in ready setting that feels tucked away while still being accessible. The main residence is warm, inviting, and tastefully updated with comfortable living spaces, natural light, and serene views of the water and surrounding trees. What truly sets this property apart is the renovated waterfront guest house, creating a rare two-residence setup ideal for visiting family, extended stays, a private office, studio, or flexible guest accommodations. Outdoor living is the centerpiece. Enjoy mornings by the creek, evenings on the deck, and weekends crabbing, fishing, kayaking, or relaxin

Price Improvement. Welcome Home to Colton's Point! Experience the rare beauty of true waterfront living at this exceptional point property, where panoramic water views surround you and create a breathtaking backdrop from nearly every room. Set on a private peninsula-like setting, this spacious 5 bedroom, 2.5 three-bath residence offers an unparalleled opportunity to own a serene retreat with endless potential. Designed for those who appreciate the water, the property features a private pier with electricperfect for boating, fishing, crabbing, or simply enjoying life on the shoreline. From sunrise over the water to spectacular evening sunsets, every day feels like a getaway. Inside, the home offers generous living spaces ideal for both everyday living and entertaining. The main level features beautiful hardwood floors, formal living and dining rooms, 3BD, 1.5 BA and sunroom. Upstairs features 2BD, 1BA and a sitting room looking onto the upper deck. This home presents the perfect opportu

Welcome to the Longview Beach community! This single-level ranch home sits on approximately 0.23 acres and offers a great opportunity for buyers looking to renovate and make it their own. Enjoy access to the Potomac River with nearby community amenities including beach, pier, and boat ramp. Property being sold as is

Nestled in the coveted waterfront community of Breton Bay, this beautifully maintained 4-bedroom, 3-bath split foyer offers space and comfort, and is move-in ready! The main level showcases stunning hardwood floors and a bright, inviting layout perfect for everyday living. The fully finished walk-out lower level features a spacious family room with a cozy fireplace, creating the ideal space for relaxing or entertaining. A large mudroom and laundry area provides excellent functionality and storage. Mudroom has epoxy flooring, laundry sink and oversized washer; washer & dryer are 1 year old. Kitchen & all 3 baths have tiled flooring. Set on a private half-acre lot, the home also offers a rear deck, two-car garage, and generous storage throughout. Leaf Filter brand gutter guards have transferable warranty. Residents enjoy optional membership to the Breton Bay Golf Course, pool, and tennis facilities, along with access to the community beach park and piermaking it easy to embrace the best

Beautiful 4 bedroom, 2 1/2 bathroom colonial located in Leonardtown. Just mins from downtown Leonardtown amenities, shopping, restaurants, schools and more. This home has hardwood floors throughout. Spacious formal living and dining rooms. Kitchen with lots of cabinets and island with seating. Breakfast area and sliding doors that open to the back yard and patio. Family room w/gas fireplace off kitchen. The second level has an owners suite with walk in closet. Owners bathroom complete with soaking tub, separate and dual vanities. 3 additional bedrooms and a full bathroom complete the top floor. Unfinished basement w/laundry area. Back yard is flat with plenty of room to spread out and enjoy outdoor activities. Gazebo and firepit are perfect for summer entertaining. Schedule your online appointment today

Great value! Reduced well below appraisal for quick sale! Welcome to your cozy water view escape without the waterfront price! Step into luxury and comfort with this newly renovated rambler. As you approach, the meticulously landscaped front yard welcomes you to a home that has been thoughtfully transformed for comfortable living. Upon entering, you'll enjoy warmth of the luxary vinyl plank floors that flow seamlessly throughout the open-concept living space. The vaulted ceiling adds an airy and open feel, creating an inviting atmosphere for both relaxation and entertainment. Nicely designed custom kitchen, a chef's delight featuring a butcher block center island, granite counters, soft close cabinetry, and stainless steel appliances, designer lighting, beverage cooler, and loads of natural light. Enjoy the beauty of the outdoors without stepping out. The expansive sunroom has numerous windows, providing breathtaking views of the waterfront surroundings. For a touch of luxury, indulge

Back on the market and now financing available! Imagine waking up each day to breathtaking sunrises over Saint Clements Bay! This delightful cottage offers a tranquil, vacation-like lifestyle with no HOA and prime waterfront access. It also presents income potential as it can sleep six. Meticulous planning has crafted this stunning home, which exudes the elegance of a high-end interior designer. Inside, you'll find a bright and airy living area that effortlessly merges indoor and outdoor spaces, showcasing captivating water views. The cottage boasts 12-foot ceilings, unique metal roof with cupola and weathervane, an upgraded well pressure tank, robust 200-amp service, full-sized washer and dryer, and a beautifully tiled bathroom with walk-in shower. Designer-inspired kitchen is adorned with quartz countertops, Verona gas range, stainless steel appliances, and a stunning tiled backsplash that frames amazing river views. The loft offers a 5-foot clearance at the center, a closet, and add

New Construction in Chaptico! Adorable Cape Cod situation on over one acre, surrounded by mature trees, creek, gorgeous pastoral views and beautiful Chaptico Sunsets! This Cape Cod welcomes you home from your hectic day to a serene surrounding with a convenient location to all amenities. You are only minutes away from Leonardtown shopping /entertainment and Pax River /Dalgren. The main level boasts a large open kitchen, dining area, and huge open den. The main level also offers an office that could be utilized as a 4th bedroom. Upstairs there are 3 large bedrooms, 2 full baths, and a sitting/flex area with stunning views! Luxury vinyl plank flooring flows through every room in this bright home. The back deck is off the heart of the home, kitchen, and is tucked in between mature woods with creek. The front porch is the place to be for'cocktail hour' to catch stunning Chaptico sunsets! This is a must see, one of kind home located in the best hidden gem of St. Mary's County; a rare opport

Beautiful inside and out, this impeccably maintained home offers exceptional curb appeal with professionally landscaped grounds, a fenced backyard, and a partially covered paver patioan ideal space for outdoor dining, relaxing, and entertaining. Inside, the thoughtfully designed floor plan includes a private home office and a dedicated dining room, perfect for both everyday living and special gatherings. The upgraded kitchen features quality finishes, an eat-in dining area, and opens seamlessly to a spacious great room, creating a warm and inviting hub of the home. Upstairs youll find four well-appointed bedrooms, including a spacious and beautifully designed primary suite highlighted by a stylish barn door detail and plenty of room to unwind. Convenient upper-level laundry adds to the homes functional layout. The finished lower level offers incredible flexibility with a large playroom, theater area, full bathroom, and an additional bedroom currently used as a workout room, along with

Welcome to 41389 Holiday Court, a stunning QBH Sotterley model located in the highly sought-after QBH community of Leonards Grant! Perfectly positioned on a desirable corner lot, this beautifully maintained 5-bedroom, 3.5-bath home offers the ideal blend of space, functionality, and thoughtful upgrades throughout. Step inside to find gorgeous hardwood floors flowing through the main level, complemented by a private home office, perfect for todays work-from-home lifestyle. The heart of the home is the grand kitchen, featuring an upgraded oversized island, butlers pantry, abundant cabinetry, and ample space for gathering, entertaining, and everyday living. Just off the kitchen, unwind in the screened-in porch or step outside to the paver patio, creating a seamless indoor-outdoor living experience. The backyard also includes a shed for additional storage and plenty of room to enjoy. Upstairs, retreat to the spacious primary suite complete with a luxurious QBH deluxe shower, offering a spa

Instant Equity! 5 Bed 3.5 Bath Colonial wu002F a fully finished basement and a 2-car garage, boasting over 4500SQFT located in Sought After Neighborhood of Leonard's Grant! Homes with this SQFT at this price point are almost non-existent. Similar homes have sold in this neighborhood for $625,000-$675,000! This home will need some cosmetic repair but is ready to shine again! From the street you are greeted by mature landscaping, a large concrete driveway and a sidewalk that takes you to the front porch. Upon entry you are greeted by a nicely sized 2-story foyer. To the right of the center hall, a living room with a formal dining room situated just in behind it. The kitchen, breakfast area, and large family room encompass the entire back portion of the main floor making this the perfect home for entertaining. A nicely finished hall bath and a large mudroomu002Flaundry room complete the main floor. Upstairs, a very large primary suite is home to a huge walk-in closet and an en-suite bath.

Price Improvement! Now Offered at $815,000 Welcome to this exceptional waterfront all-brick rambler, thoughtfully updated and ready for immediate enjoyment! A true waterfront property on 1.19 acres with an impressive 262 feet of shoreline, this property delivers sweeping, panoramic water views from sunrise to sunset in a serene, tree-lined setting filled with natural beauty and wildlife. It's a rare find to have a home in this great condition on the water at this price. Inside, youll find 3 generously sized bedrooms, 2.5 updated baths, and an inviting open-concept layout ideal for both everyday living and entertaining. The living and family rooms are anchored by a striking double-sided brick fireplace with gas logsperfect for cozy gatherings. A spacious 20 x 20 bonus room offers endless possibilities as a recreation space, home office, or media room. The kitchen has been beautifully refreshed with quartz countertops, solid wood cabinetry, and stainless steel appliances. New luxury viny

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, communit

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!

Welcome to a truly special offeringthis beautifully restored historic home, originally built in 1830, blends timeless character with thoughtful modern updates, all set on 1.75 private acres overlooking Whites Neck Creek. Ideally located, this property offers the perfect balance of privacy and convenienceapproximately 20 minutes to Leonardtown, 40 minutes to PAX River Naval Air Station, and just about 70 miles from Washington, D. C. With over 2,000 square feet of living space, this 3-bedroom, 2 full bathroom home has been lovingly maintained and extensively improved, preserving its charm while enhancing everyday comfort. Inside, youll find refinished original hardwood floors, fresh paint throughout, a new gas fireplace insert and upgraded recessed lighting that brightens each space while honoring the homes historic roots. The kitchen has been updated with a new gas cooktop and refrigerator, creating a functional and inviting space for everyday living. Major improvements have already bee

Welcome to this beautifully maintained contemporary home in the sought-after Society Hill section of Breton Bay, offering privacy, space, and timeless character on a generous. 60-acre lot. From the moment you step inside, youre greeted by soaring two-story ceilings in the great room, highlighted by rich hardwood floors and a striking stone gas fireplace that creates a warm and inviting focal point. The updated kitchen features granite countertops, distinctive wood ceilings, and seamless flow into the combined dining and living areas. A main-level bedroom and full bath provide flexible living options for guests or multigenerational needs. Upstairs, youll find two additional bedrooms and a full bath, while the finished basement expands the living space with another bedroom and full bath, perfect for a private suite, home office, or recreation area. The screened-in porch overlooks the peaceful, private backyard, offering the perfect setting to relax and enjoy the natural surroundings. Maj

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 you’re 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 station—perfect for boating, fishing, crabbing, or simply enjoying peaceful days on the river. Inside, you’re 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 gu

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

Instant Equity! 5 Bed 3.5 Bath Colonial w/ a fully finished basement and a 2-car garage, boasting over 4500SQFT located in Sought After Neighborhood of Leonard's Grant! Homes with this SQFT at this price point are almost non-existent. Similar homes have sold in this neighborhood for $625,000-$675,000! This home will need some cosmetic repair but is ready to shine again! From the street you are greeted by mature landscaping, a large concrete driveway and a sidewalk that takes you to the front porch. Upon entry you are greeted by a nicely sized 2-story foyer. To the right of the center hall, a living room with a formal dining room situated just in behind it. The kitchen, breakfast area, and large family room encompass the entire back portion of the main floor making this the perfect home for entertaining. A nicely finished hall bath and a large mudroom/laundry room complete the main floor. Upstairs, a very large primary suite is home to a huge walk-in closet and an en-suite bath. The bat

Experience waterfront living at its finest in this beautifully renovated home overlooking Saint Clements Bay. Designed to maximize the stunning bay views, the light-filled interior offers an open-concept layout that seamlessly blends comfortable everyday living with exceptional entertaining space. Featuring 4 bedrooms, 2 full baths, and 2 half baths, this home showcases modern finishes, coastal charm, and a highly functional floor plan. Expansive windows frame breathtaking views throughout much of the home, while the waterfront deck provides the perfect setting for outdoor dining, entertaining, or simply relaxing. Outside, the private L-shaped pier offers direct access to boating, fishing, kayaking, and all the recreational opportunities waterfront living has to offer. Ideally located just minutes from Leonardtown Square, this rare waterfront opportunity combines breathtaking views, modern updates, and convenient access to shopping, dining, and local amenities. Enjoy the best of coasta

Well if you blinked you did miss it BUT now you have a chance to get it again because buyers financing did not happen. Don't blink because this beauty will be swept up quickly. Property is in excellent condition and is ready for its new owner. House is kept in immaculate condition. No painting, flooring, etc. Needed. Just move right in. Less than half mile to Wicomico River

Just reduced! This home is located in the tucked-away community of Longview Beach at 36797 Ricardo Drive, Bushwood, Maryland, and is currently priced at $340,000.00. Sitting on 10,500 sf. Is just under 1/4 acre. This recently updated home with great features for winter is the perfect location for the summer. A new metal roof with lighting rods was installed in 2019, including upgrading installation in the attic/ceiling and exterior walls. Home features a renovated eat-in kitchen with custom cabinets, a large kitchen counter area for breakfast, and new lighting that opens into the family room. The kitchen has access to the rear yard, and a covered carport or front porch area completes the living space. This gem is awaiting a new owner to enjoy all the benefits of just a short a quiet haven for all nature lovers to sip your morning coffee and watch the wildlife that passes by. In the early morning, you can take a walk down less than half a mile to the shoreline for some early morning fis