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$60,000
Now is your opportunity to build equity and the home that's just for you in the quiet, water-access community of Longview Beach. Whether you are looking to build for investment or simply plant roots locally, this property offers exceptional versatility. Key highlights of this listing include: - Expansion Potential: This single lot is accompanied by an adjacent perc-approved lot for sale, ( 36913 VIEWRIVER DR) allowing you to build two homes or combine the lots for a larger primary residence with an accessory dwelling. - Permit Ready: A building permit is already on file for Lot 18. - Negotiable Extras: Potential home plans can be included as part of the sale negotiations. All buyers are encouraged to perform their due diligence with the local planning office and Health Department to confirm specific project requirements.

36919 Viewriver Dr, Bushwood

Listing courtesy of RE/MAX One. Contact: 4437718009

$3,500,000
3 Beds ⋅ 2 Baths
Welcome to Timerity, a natural sanctuary tucked away on an 189-acre waterfront estate where Southern Maryland history, productive farmland, mature woods and protected tidal waters come together in one extraordinary property. Documented by the Maryland Historical Trust as Timerity Farm, the property reflects the agricultural and maritime heritage of the Drayden area and the historic St. George’s Hundred landscape of St. Mary’s County. The Trust identifies the residence as a mid-19th-century historic resource, while an earlier survey records an owner tradition suggesting 1790. At the heart of the farm stands a distinctive one-and-one-half-story frame residence with a traditional side-passage/double-parlor plan, hardwood floors, separate fireplaces, painted moldings and a rare historic brick pent chimney. The home offers three bedrooms, including one on the main level and two upstairs, along with two full baths. A working country kitchen opens to a generous gathering space, while the side porch provides a relaxed setting for entertaining, crab feasts and enjoying the surrounding waterfront views. The property unfolds across approximately 189 acres of open farmland, mature woodland and secluded shoreline, creating an exceptional sense of privacy. Roughly rectangular in shape, the land occupies the end of a peninsula and is surrounded on three sides by water, with the public road coming to an end at the entrance to the property. The 189 acres have approximately 1/3 open farmland and 2/3 mature woodland and secluded shoreline. The agricultural fields are presently leased to a local farmer, while the wooded portions provide habitat for the abundant wildlife for which Southern Maryland’s tidewater country is known. Approximately 5,000 linear feet of protected shoreline extend along School House Creek, with boating access through St. George Creek to the Potomac River. A private pier and a grandfathered previous pier depicted by the remaining pilings serves the residence with water depth estimated at approximately 6 feet at Mean Low Water further up School House Creek. The Schoolhouse Creek shore is historically protected waterfront sheltered from severe storms and is well suited for boating, fishing, kayaking and paddleboarding. In addition to the historic residence, the property includes three modest cottages and three barns/outbuildings, adding flexibility for agricultural use, storage, workshops, guest accommodations or future restoration. Transferable Development Rights “TDR” have not been exercised and remain available. Few properties combine this degree of acreage, waterfront, privacy and documented history in one setting. Whether envisioned as a private family estate, working farm, sporting retreat, waterfront sanctuary or legacy property to be preserved for generations, Timerity, offers a rare opportunity to own an exceptional piece of Southern Maryland’s Chesapeake tidewater landscape. This estate has seen a diverse history. Ownership allows you to write the next chapter adding to the growing legacy of this waterfront retreat.

45776 Boothe Rd, Drayden

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279

$699,900
3 Beds ⋅ 2 Baths
If you've been dreaming of waterfront living, now is your chance. Whether you enjoy boating, fishing, crabbing, or simply relaxing while taking in breathtaking water views, this beautifully renovated home has it all. Step inside to discover a spacious, open-concept kitchen and family room designed for gathering and everyday living. The stunning backyard provides the perfect setting for entertaining guests or creating lasting memories with family and friends. This move-in-ready home features a new HVAC system, beautifully updated bathrooms, brand-new flooring throughout, an encapsulated crawl space, and countless additional upgrades that offer both comfort and peace of mind. Opportunities like this don't come around often—schedule your showing today before it's gone!

18937 Hodges Ln, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

$499,900
4 Beds ⋅ 3 Baths
********Priced Below Appraised Value****** Welcome to one-level living at its finest in this beautiful, brand-new 4-bedroom, 2.5-bath rancher located in Lexington Park. Thoughtfully designed with comfort and functionality in mind, this home is ideal for anyone seeking easy living without stairs. Step inside to discover a bright, open floor plan featuring luxury vinyl plank flooring, a spacious living area, and a stylish kitchen outfitted with stainless steel appliances, granite countertops, and a large center island—perfect for cooking, entertaining, and everyday living. The owner’s suite offers a peaceful retreat with a walk-in closet and private en suite bath. Three additional bedrooms and a full hall bath provide plenty of space for guests, family, or a home office. A convenient half bath and dedicated laundry room complete the layout. Situated just minutes from NAS Patuxent River, shopping, dining, and schools, with easy access to commuter route, this home offers both style and convenience.

23195 Esperanza Dr, Lexington Park

Listing courtesy of RE/MAX One. Contact: 4437718009

$350,000
5 Beds ⋅ 2 Baths
All forms of financing are available for this property. Attention Developers or Land Loving Owner Occupants!! Welcome to 23011 Newtowne Neck Road in Leonardtown, Maryland. Situated on more than four acres, this spacious five-bedroom, manufactered two-bath rambler offers a rare combination of comfortable one-level living, privacy and future possibilities. he generous homesite provides abundant room for outdoor recreation, gardening, equipment storage, animals or creating your own private retreat. The property may also appeal to builders, investors or buyers exploring potential subdivision or development opportunities, subject to county zoning, approvals, utilities and feasibility studies. Inside, the home offers a flexible five-bedroom layout with space for home offices, guest rooms, multigenerational living or hobby areas. Its rambler-style design provides convenient everyday living with minimal stairs. Located near historic Leonardtown, local shopping, dining, schools, medical facilities and Southern Maryland commuter routes, this property is ideal for buyers seeking acreage without sacrificing access to nearby amenities. Bring your vision and discover the potential of this distinctive Leonardtown property.

23011 Newtowne Neck Rd, Leonardtown

Listing courtesy of Samson Properties. Contact: (703) 378-8810

$680,000
4 Beds ⋅ 2 Baths
Nestled on a generous 3.8-acre corner lot, this charming Cape Cod-style home, built in 2017, offers a perfect blend of comfort and timeless appeal. With its excellent condition and thoughtful design, this residence is ready to welcome you home. Step inside to discover a warm and inviting interior that features a traditional floor plan, ideal for everyday living and entertaining. The home offers four well-appointed bedrooms, including a convenient entry-level bedroom, perfect for guests or those seeking single-level living. The primary suite features a walk-in closet and a spa-like bathroom complete with a soaking tub and a walk-in shower, providing a serene retreat at the end of the day. Additional interior highlights include plush carpeting, elegant hardwood floors, and ceiling fans that enhance comfort throughout the seasons. For those who appreciate technology, the home is equipped with a sound system, ensuring that your favorite tunes accompany you in every room. Outside, the property features a screened in porch, perfect for outdoor relaxation while enjoying the tranquility of your surroundings. The oversized detached garage offers ample space for vehicles and storage and has heat/ac, electricity and plumbing while complemented by a paved driveway for easy access. There is ample parking space for vehicles, campers, and more! Enjoy the peace of country living while being just a short drive from local amenities, shopping, and dining options. Don't miss the opportunity to make this beautiful residence your forever home!

25375 Loveville Rd, Leonardtown

Listing courtesy of RMG Realty. Contact: 5407091011

$309,000
3 Beds ⋅ 2 Baths
Welcome to 21508 Forest Run Drive in Lexington Park, MD��a beautifully renovated, move-in-ready home updated in 2025! This charming property features 3 bedrooms, 2 full bathrooms, convenient one-level living, and an expansive yard with plenty of space to relax, entertain, or play. Best of all, there is no HOA! Located just minutes from NAS Patuxent River, this home is perfect for first-time buyers, those looking to downsize, or anyone seeking modern updates and comfortable living in a convenient location. Recent Updates & Improvements worth approx $10,000! This property has been thoughtfully refreshed and prepared for its next owner. Recent improvements include a brand new electric oven, new air filter, and deep cleaning throughout the home. The deck has been thoroughly cleaned, and stained, the shed has been freshly painted, and additional concrete has been added to the parking area for improved functionality. Manicured outdoor landscaping was added for a curb appeal. Move-in ready and well cared for, this home offers a clean and refreshed setting both inside and out. Schedule your showing today to see the recent improvements in person!

21508 Forest Run Dr, Lexington Park

Listing courtesy of JPAR Real Estate Professionals. Contact: 3016844895

$430,000
4 Beds ⋅ 4 Baths
Welcome home... this stunning end unit townhome located in the Orchid Park neighborhood of Wildewood. This beautiful home is move-in ready and perfectly situated just minutes from NAS Pax River, offering easy access to local schools, shopping, dining, and entertainment. Key Features: Versatile Entry Level Suite: Perfect for guests or multi-generational living, this level features a spacious fourth bedroom (flex space) paired with a full bathroom. Enjoy seamless indoor-outdoor living with direct access to a private walk-out patio. This area includes a large storage closet and is complete with a one-car garage and foyer. Gourmet Kitchen: The main level features an open-concept layout with a large sit-down island, upgraded cabinetry, quartz countertops, gas range, double oven, stainless steel appliances, and under-cabinet lighting. Thoughtful Upgrades: Enjoy abundant natural light and a modern feel with recessed lighting throughout, luxury vinyl plank (LVP) flooring on the entry and main levels and upgraded carpeting on the upper level. Primary Suite: Unwind in the spacious upper-level primary suite, which features a walk-in closet and a private en-suite bath boasting quartz countertops, a double vanity, upgraded cabinetry, tile flooring, and an upgraded tiled shower with a glass door. Main Level Entertaining: The open-concept design flows from the kitchen into the living room and dining area, complete with a convenient half bath and oversized sliding glass doors which open onto a deck. Quality Finishes: Throughout the home, you’ll find upgraded custom blinds, tile in all full bathrooms and an upgraded washer and dryer set.

23080 Vanda Way, California

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4103940990

$490,000
4 Beds ⋅ 3 Baths
Built in 2023, this beautifully maintained 4-bedroom, 2.5-bath colonial offers over 2,500 square feet of thoughtfully designed living space. The open-concept main level features luxury vinyl plank flooring, a spacious family room with a shiplap accent wall, and a stunning kitchen with a large center island, quartz countertops, black stainless appliances, and ample cabinetry. A dedicated office provides the flexibility for remote work or a potential main-level guest room. Upstairs, the spacious primary suite boasts a large walk-in closet and an en-suite bath with a walk-in shower and double vanity, along with three additional generously sized bedrooms and a convenient second-floor laundry room. The unfinished basement includes a full bath rough-in, offering endless possibilities for future expansion. Situated on a quiet cul-de-sac with a private, tree-lined backyard, this home also features a 2-car garage, paved driveway, public water and public sewer, and a Tesla EV charger already installed. Enjoy the peace of mind that comes with newer construction—without the wait!

22621 Woods Ln, Lexington Park

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636

$420,000
4 Beds ⋅ 2 Baths
Must-See Turn-Key Home on a Private 1-Acre Lot Backing to Trees! Welcome home to this beautifully maintained, turn-key 4-bedroom, 2-bathroom home offering approximately 2,100 square feet of comfortable living space. Situated on a private 1-acre lot backing to mature trees, this home offers plenty of space both inside and out. The inviting interior features new carpeting throughout the spacious and functional layout that has plenty of room for everyday living and entertaining. The kitchen is equipped with stainless steel appliances and offers ample workspace for preparing meals. The adjacent dining room features a sliding glass door leading directly to the spacious deck, creating an ideal flow for indoor-outdoor entertaining. Four comfortable bedrooms provide flexibility for family, guests, a home office, or hobby space. The fourth bedroom is a special bonus, featuring its own sliding glass door providing direct access to the backyard—perfect for a guest suite. Step outside and enjoy the peaceful, tree-lined setting from the large deck. The expansive backyard also features a large storage shed and cozy fire pit, creating the perfect space for summer gatherings, outdoor activities, and relaxing evenings around the fire. With a spacious lot, desirable outdoor amenities, a versatile interior layout, and easy access to major commuter routes, this property offers the perfect combination of privacy and convenience. Turn-key, move-in ready, and ready to welcome its next owners—don’t miss this one!

41012 Oakville Rd, Mechanicsville

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

$850,000
REDEVELOPMENT, LAND AND INVESTMENT OPPORTUNITY near the intersection of MD Route 235/Three Notch Road and MD Route 247/Loveville Road. Approximately 5.6 acres offer a distinctive combination of open usable land, a former community baseball field, expansive gravel parking and circulation areas, and mature wooded buffers. The property also includes an approximately 3,200-square-foot former restaurant/bar building with significant fire damage. The land, property and all existing improvements are being conveyed strictly AS IS. The value is primarily in the land, location, existing site layout and future redevelopment potential. This unique property may appeal to small builders, local developers, land investors, recreation or sports operators, community and faith-based organizations, agri-business or agri-tourism entrepreneurs, and owner-users seeking acreage with convenient access to major area roadways. The property is presently identified as RPD. Seller reports a history of commercial use; however, buyers must independently verify permitted uses, any legal nonconforming-use status, restoration or redevelopment rights, subdivision potential, access, utilities, environmental conditions and all required governmental approvals. Bring your builder, land-use professional, engineer and architect—and explore the possibilities for this well-known community property’s next chapter. Conceptual renderings are provided solely to illustrate possible uses and are not engineered site plans, approvals, representations or guarantees. Buyers must independently verify zoning, permitted uses, development potential, utilities, access and all governmental requirements. Interested buyers should consult St. Mary’s County Land Use & Growth Management and their professional advisors regarding their proposed use.

26511 Loveville Rd, Mechanicsville

Listing courtesy of Real Broker, LLC. Contact: 8504500442

$475,000
5 Beds ⋅ 3 Baths
Welcome to 30160 Curtiss Road in Mechanicsville! Set on a level 0.73-acre corner lot, this spacious 5-bedroom, 3-bath home offers 2,204 finished square feet and a flexible layout with room for guests, a home office, hobbies, or everyday living. The fully finished lower level features a ground-level side entrance and a full bath with a walk-in tub, adding convenience and versatility. A newer HVAC system provides added peace of mind. Outside, enjoy the above-ground pool, expansive flat backyard, attached carport, generous driveway parking, and two storage sheds—plenty of space for entertaining, gardening, projects, and storage. Located in northern St. Mary’s County, the home offers convenient commuting access to NAS Patuxent River, Joint Base Andrews, and Naval Support Facility Indian Head, along with shopping, dining, and Southern Maryland attractions, including Historic St. Mary’s City. Schedule your showing and discover all the space and flexibility this property has to offer!

30160 Curtiss Rd, Mechanicsville

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636

$309,900
3 Beds ⋅ 4 Baths
Welcome to this beautifully maintained 3-bedroom, 3.5-bath townhome offering nearly 2,000 square feet of comfortable living space. This Move in ready home has a new roof, fresh paint, and carpets just steam cleaned! Designed with both functionality and style in mind, this home features a spacious, open-concept main level that seamlessly connects the living, dining, and kitchen areas, perfect for everyday living and entertaining. The upper level offers a generous primary suite with a private bath, along with two additional bedrooms and another full bathroom. The finished lower level provides flexible living space with a full bath, making it ideal for a theater room, den, guest suite, home office, or recreation area. Conveniently located near shopping, dining, schools, and NAS Patuxent River, this home offers the perfect combination of space, comfort, and convenience. Whether you're a first-time homebuyer, downsizing, simplifying, or looking for an investment opportunity, this townhome is ready to welcome you home.

22416 Dark Star Way, Lexington Park

Listing courtesy of Topside Realty. Contact:

$550,000
5 Beds ⋅ 4 Baths
Welcome to 45962 Blue Jay Ct in Great Mills! This beautifully maintained 5-bedroom home has been thoughtfully upgraded throughout, offering a perfect blend of comfort, functionality, and entertaining space. The updated kitchen features modern finishes and flows seamlessly into the living areas, while the fully finished basement provides additional living space complete with a full downstairs kitchen—ideal for guests, multigenerational living, a home office, or recreation. Outside, enjoy your own private backyard retreat featuring a fully fenced-in yard, outdoor kitchen, firepit, and an expansive screened-in rear deck perfect for relaxing or entertaining year-round. The property also includes both an attached and detached garage, providing exceptional storage, parking, and workspace options. This home offers the space, upgrades, and outdoor amenities you've been looking for in a desirable Great Mills location.

45962 Blue Jay Ct, Great Mills

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636

$799,000
5 Beds ⋅ 3 Baths
17.5 Acres on Cuckold Creek. Rare large waterfront property of 17.5+ acres to provide you peace, quiet and privacy on highly desired Cuckold Creek. The 17.5 acres are mostly level and heavily wooded with walnut, Cypress, Maple, Oak and pine . Wildlife abounds. The Hickory Landing community dock on the property will have your own boat slip. A large garden plot is right on Hickory Landing Way, but tucked way down a beautiful long and winding driveway, you find the house on the water. Originally built in 1983, the house takes full advantage of the extraordinary water view of Cuckold creek with soaring cathedral ceilings of exposed beams and 2"x4" tongue and groove. The addition from mid 90's also takes full advantage of the extraordinary water views with dozens of Anderson window casement windows in excellent condition. The property contains a solid one room cabin with wood stove for you to use your imagination with. New standing seam metal roof put on the cabin in 2022. New 10'x14' outbuilding with 8'doors placed on the property this summer. Property sold as-is, however numerous improvements made this year, You could be waiting a very long time before another property like this comes to market. Please call listing agent for more information.

44908 Hickory Landing Way, Hollywood

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4103940990

$20,000
Build your dream coastal retreat on this beautiful 0.43-acre vacant lot located at 23253 Maddox Road in the desirable, water-oriented community of Bushwood, MD. Positioned in scenic St. Mary’s County, this lot offers the perfect foundation for a custom single-family home or vacation getaway. The critical site prep legwork is already underway—the property is approved for 2 mound septic systems, saving you valuable time and uncertainty during the planning phase. Engineered drawings and mound plans are available directly upon request from the listing agent. Enjoy proximity to local waterways, boat launches, fresh seafood dining, and peaceful Southern Maryland living—all while staying within easy driving distance to Lexington Park, PAX River, and Washington D.C. Bring your builder, bring your blueprints, and start living the waterfront-lifestyle dream today!

23253 Maddox Rd, Bushwood

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636

$395,000
2 Beds ⋅ 3 Baths
This house comes with a REDUCED RATE as low as 5.875% (APR 6.313%) as of 08/21/2026 through List & Lock™. This is a seller paid rate-buydown that reduces the buyer’s interest rate and monthly payment. Terms apply, see disclosures for more information. Pride of ownership is evident from the moment you arrive. Step inside to a warm and inviting interior featuring bamboo flooring, tasteful finishes, abundant natural light, and a soothing color palette throughout. The kitchen is both stylish and functional, offering granite countertops, stainless steel appliances, soft-close cabinetry, and ample countertop space. The adjoining dining area comfortably accommodates a table for six and flows seamlessly into the bright and welcoming living room. Just off the living room, enjoy easy access to a beautifully hardscaped rear yard, including a seating bench and fire pit, as well as a fully vinyl privacy-fenced backyard. Beyond the fence, a peaceful retention pond creates a tranquil backdrop where turtles, herons, and other local wildlife are frequent visitors. The main-level owner's suite is spacious with large windows and a convenient en-suite bath. A second bedroom and an additional full bathroom complete the main level, providing comfortable accommodations for family or guests. The large 3rd Bedroom is non-egress and located in the lower level with a very large walk-in closet, adjacent to the very spacious lower-level family room. The oversized front-load garage offers flexibility for two compact vehicles or one full-size vehicle with additional room for storage, a workshop, or hobby space. Additional updates and features include a new roof (2020) and a Tesla-managed solar energy system. The solar system helps keep utility costs exceptionally low. Winters months ($20-50), higher summer months ($60-$80) average. This home offers a convenient location with easy access to NAS PAX River and the Lexington Park/Pax River employment corridor; an important advantage for military, DoD, and contractor households looking to keep their day-to-day routine manageable. Beyond the commute, the surrounding area offers the conveniences families need when settling into a new neighborhood. For time outdoors, nearby recreation options include parks, athletic fields, playgrounds, trails, beaches, fishing, kayaking, and access to the waterways that make Southern Maryland such a distinctive place to live. Chancellor’s Run Regional Park provides sports and recreation close to home, while destinations such as Myrtle Point Waterfront Park and St. Mary’s River State Park offer opportunities to hike, fish, picnic, paddle, and enjoy the water. And while at home, the property continues that lifestyle with a privacy-fenced backyard, extensive hardscaping, fire-pit area, pond setting, and outdoor space designed to actually be enjoyed.

45525 Coosan Ct, Great Mills

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

$169,000
3 Beds ⋅ 2 Baths
This may be the opportunity you've been waiting for. Imagine coming home to a place that's truly yours. This inviting 3-bedroom, 1.5-bath townhome offers the space, comfort, and affordability today's buyers have been searching for. Whether you're purchasing your first home, relocating to the area, or adding to your investment portfolio, this home delivers exceptional value in a convenient location. Step inside to a spacious living area that's perfect for relaxing after a long day or gathering with family and friends. The eat-in kitchen offers plenty of cabinet space and room to cook, dine, and create memories. Upstairs, you'll find three comfortable bedrooms and a full bath, while the main level features a convenient half bath for guests. Outside, enjoy a fenced rear yard with space for entertaining, gardening, pets, or simply unwinding. Central air conditioning, a heat pump, public water and sewer, and off-street parking provide the convenience and low-maintenance lifestyle today's buyers appreciate. Location matters, and this home delivers. Just minutes from NAS Patuxent River, shopping, restaurants, schools, parks, and everyday conveniences, you'll spend less time commuting and more time enjoying life. Affordable homes in this price range don't stay available for long. If you've been waiting for the right combination of value, location, and opportunity, this is your chance. Schedule your private showing today and discover why homeownership could be closer than you think.

46842 Patuxent Rd, Lexington Park

Listing courtesy of Expect Results Realty. Contact: 2408443318

$17,500
Rare ½-Acre Double Lot in Peaceful Water-Oriented Community – Ready for Your Custom Build! Bring your builder and your vision to 36784 Ricardo Drive! Situated in a quiet, water-oriented neighborhood in historic Bushwood, Maryland, this unique offering includes two adjacent parcels combined to form a spacious 0.5-acre lot. Whether you're dreaming of a sprawling full-time residence, a relaxed weekend getaway, or a custom home with extra space for a pole barn, garden, or boat storage, this level, versatile lot gives you the flexibility and privacy rarely found on single community lots. Enjoy the ultimate Southern Maryland coastal lifestyle! Located just minutes from public water access, local marinas, and the nearby Bushwood Wharf boat ramp, you'll have easy access to the scenic Wicomico and Potomac Rivers for boating, crabbing, fishing, and kayaking.

36784 Ricardo Dr, Bushwood

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636

$599,900
3 Beds ⋅ 1 Baths
Some properties are purchased for the house. Others are purchased for the place. Set on a narrow finger of land between two bodies of water, 16101 Piney Point Road offers an extraordinary waterfront setting with sunrise light on one side and spectacular sunset views on the other. The existing cottage provides an immediate place to enjoy life, watch the sky change, enjoy the water, and begin imagining what might come next. Inside, the home is modest, comfortable, and full of personality, with water visible from several rooms, a spacious primary bedroom, two additional bedrooms, an updated full bath, central heating and air conditioning, laundry, and a simple kitchen with cooktop. Enjoy the property as your full-time residence or weekend retreat and explore the potential for future expansion designed to take fuller advantage of the remarkable setting and views, and over 492 linear feet of shoreline! Any future construction, expansion, elevation, or redevelopment is subject to governmental approvals and buyer verification. The neighboring properties at 16102 and 16104 Piney Point Road are also separately offered for sale, creating the rare possibility of acquiring the entire residential tip of Piney Point Road for a private family estate or multi-generational waterfront retreat. Each property is separately owned, listed, and offered for sale. ***PUBLIC SEWER ALREADY INSTALLED***

16101 Piney Point Rd, Piney Point

Listing courtesy of RE/MAX One. Contact: 4102244400

$575,000
4 Beds ⋅ 3 Baths
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 multiple closets, a dressing area, and an ensuite bathroom that was also renovated in 2024 with a sleek, modern motif. The owners suite features a private covered deck overlooking the back yard and farm land, making it a quiet retreat for relaxing after a long day. The lower level is partially finished with a 4th bedroom, 3rd full bathroom, and spacious second family room. The family room enjoys a bar for entertaining, as well as access to the two car garage. The remaining lower level contains laundry, built-in storage cabinets, and tons of storage space! The heat pump was replaced in 2024, and the roof was replaced with 40 year shingles in 2010. A Mini Fridge in the basement bar and a refrigerator in the garage convey. This home is uniquely located in Breton Bay, and enjoys views of the golf course, and views of the farmland behind the home. It's also within walking distance to the Breton Bay Clubhouse, and a mere 7 minutes to downtown Leonardtown. The community enjoys a beach area and playground for a minimal annual fee. Membership to the Breton Bay Country Club grants access to the pool and tennis courts. Welcome Home!

22010 Society Hill Rd, Leonardtown

Listing courtesy of Compass. Contact: (703) 229-8935

$615,000
5 Beds ⋅ 4 Baths
Welcome to 23620 Gunnell Dr., a beautiful, large colonial style home built by Marrick Homes in 2005. Pride of ownership shows with this home as it has been wonderfully maintained and upgraded since it was built. This home features 5 bedrooms, 4 full bathrooms, a fully finished basement, multiple bump outs, multiple entertaining areas, an oversize double car garage, a bar in the basement and so much more just inside the walls! Outside the walls of the home, features a shed, fenced in backyard, a beautifully manicured lawn watered by an in-ground irrigation system and several flower beds for all a plant enthusiast could ever ask for! Situated in the subdivision known as The Villages at Leonardtown, we are only minutes from all the shops, dining, and attractions Leonardtown has to offer, with a further drive to all the shops, attractions, dining near Pax River Naval Base and the surrounding area offers. Come take a look at this home today!

23620 Gunnell Dr, Leonardtown

Listing courtesy of Coldwell Banker Premier. Contact: 5406624500

$2,250,000
4 Beds ⋅ 4 Baths
Welcome to Mount Olive Farm! A breathtaking 39-acre horse farm featuring a beautifully restored manor home originally built in 1880. Rich in history and thoughtfully updated over the years, this exceptional estate seamlessly blends timeless character with modern amenities. The home features a stunning gourmet kitchen addition equipped with a commercial-grade range, Viking double ovens, a wood-burning fireplace, and French doors leading to a spacious 30' x 20' screened porch overlooking the picturesque farm. Additional living spaces include a library, private office, art studio, family room, sitting room, and an inviting grand front porch. Hardwood and brick flooring add warmth and charm throughout. The upper level offers three bedrooms and two beautifully remodeled bathrooms. Exterior improvements include maintenance-free siding, replacement windows, and updated gutters for worry-free ownership. Formerly operated as a successful equestrian center and event venue, the property is ideally suited for horse enthusiasts, boarding, training, competitions, or continued event use. The farm includes five fenced pastures and paddocks, a professionally designed 100' x 200' dressage arena, scenic riding trails, and two tranquil ponds. The impressive 135' x 75' main barn features six horse stalls, a large indoor riding arena with a temporary dividing wall for events, office, tack room, viewing room, wash stall, and bathroom. A second barn offers six additional stalls with rubber mat flooring, tack room, ample storage, and a full apartment on the upper level—perfect for a caretaker, trainer, or guests. Additional structures include multiple storage buildings one that serves as a three-car garage, equipment shed, formal gardens, and a beautiful in-ground swimming pool, creating an extraordinary blend of country living and recreational amenities. The property was previously approved for the Maryland Agricultural Land Preservation Foundation (MALPF) program, although the easement was never initiated, providing future owners with valuable options. An additional approved 3-acre building lot is included in the sale, adding even more value and potential. This one-of-a-kind estate offers endless possibilities as a private equestrian retreat, income-producing horse facility, event venue, or exceptional country residence. A rare opportunity to own one of the area's most versatile and picturesque horse properties.

45433 Drayden Rd, Valley Lee

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279