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$625,000
3 Beds ⋅ 3 Baths
Welcome to 20890 Aster Drive, where privacy, efficiency, and timeless charm come together on more than 4 peaceful acres in the heart of Callaway. This inviting Cape Cod offers the freedom of country living with no HOA, while providing exceptional value through major system upgrades that make homeownership both comfortable and economical. Step inside to discover a light-filled family room with soaring cathedral ceilings, abundant windows, and a cozy wood-burning fireplace that creates the perfect gathering space. The thoughtfully designed floor plan features a desirable main-level primary suite, spacious laundry room complete with cabinetry and a utility sink, and an upgraded kitchen equipped with a new refrigerator and induction range. Outside, the established landscaping and attractive hardscaping create a beautiful setting to enjoy from the welcoming wraparound front porch. A two-car attached garage and unfinished basement provide abundant storage and future possibilities. Woodworking enthusiasts will especially appreciate the basement's built-in dust collection system, making it an ideal workshop. The true value of this home lies in its extensive recent improvements. A brand-new geothermal HVAC system (2025), new 50-year architectural shingle roof (2025), and owned solar panels combine to deliver remarkably low utility costs for years to come. While a few cosmetic updates could further personalize the home, all the major investments have already been made, and the property has been meticulously maintained throughout ownership. If you've been searching for acreage, privacy, low operating costs, and a solid home with incredible potential, 20890 Aster Drive is a rare opportunity to make your own while enjoying peace of mind from day one.

20980 Aster Dr, Callaway

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$399,900
2 Beds ⋅ 1 Baths
Opportunity meets waterfront potential at 16102 Piney Point Road. Set in a distinctive coastal location, this property offers buyers the chance to create something truly special along the water. The existing structure is in need of substantial renovation and may also be considered a candidate for removal and replacement. This is not a cosmetic project. Buyers should expect a serious undertaking and conduct their own due diligence regarding the home’s condition, renovation feasibility, permitting, utilities, and future building plans. What makes this property compelling is the setting. With waterfront or water views, an established homesite, existing improvements, and access to utilities, the groundwork is already here for a buyer with vision. Renovate the existing home, reimagine the site, or explore the possibility of building a new waterfront retreat tailored to the way you want to live. Properties with this combination of location, water, land, and future potential are increasingly difficult to find. Bring your contractor, architect, and imagination. The next chapter of 16102 Piney Point Road is ready to be written.

16102 Piney Point, Piney Point

Listing courtesy of RE/MAX One. Contact: 4102244400
$750,000
3 Beds ⋅ 3 Baths
Experience breathtaking panoramic views of Breton Bay and unforgettable sunsets! Cape Cod-style home featuring 3 bedrooms plus a spacious loft. Designed to maximize the water views, the home offers hardwood floors throughout and an inviting floor plan with a living room, family room, dining room, and breakfast room—all overlooking the bay. Enjoy the expansive 37' x 8' front porch or the equally generous 37' x 8' rear porch, where you can relax and take in the peaceful waterfront scenery. Recent updates include new siding, a new roof, and a new gutter system. The side-load garage includes a staircase leading to a large upper-level storage area. Perfectly situated next to the neighborhood beach and pier, this property offers easy access to the waterfront and outdoor recreation. It's also within walking distance of the Breton Bay Golf & Country Club, where memberships are available for golf, swimming, and dining at the clubhouse restaurant. Whether you're looking for a year-round residence or a weekend retreat, this exceptional home combines stunning views, thoughtful updates, and an unbeatable location in one of Breton Bay's most desirable settings.

40579 Port Pl, Leonardtown

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279
$529,000
3 Beds ⋅ 2 Baths
Welcome to 47558 Lucas Cove Lane, where peaceful waterfront living meets endless potential. Tucked away on a private, wooded double lot overlooking scenic Lucas Cove, just off the beautiful St. Mary's River, this charming 3-bedroom, 2-bath home offers a rare opportunity to enjoy the best of Southern Maryland's waterfront lifestyle. Designed to maximize its exceptional setting, the home is surrounded by expansive water views and boasts an impressive amount of linear shoreline, creating a tranquil backdrop for everyday living. Whether you're sipping your morning coffee while watching the sunrise over the cove, entertaining family and friends, or simply enjoying the serenity of nature, this property delivers the privacy and waterfront experience you've been searching for. Inside, the home offers comfortable living spaces filled with natural light, while the unfinished second story presents an incredible opportunity to expand. Create additional bedrooms, a luxurious primary suite, a home office, or a recreation space—the possibilities are limited only by your imagination. The oversized double lot provides room to relax, garden, or further enhance the property, all while enjoying the peaceful surroundings and abundant wildlife. Conveniently located just minutes from marinas, restaurants, historic St. Mary's City, and Leonardtown, this waterfront retreat offers the perfect blend of seclusion and accessibility. Whether you're looking for a full-time residence, a weekend getaway, or a waterfront property with room to grow, 47558 Lucas Cove Lane is a rare opportunity to own a slice of paradise on the St. Mary's River. Schedule your private showing today and discover everything this exceptional waterfront property has to offer.

47558 Lucas Cove Ln, Lexington Park

Listing courtesy of Infinitas Realty Group. Contact: 2409252224
$609,900
3 Beds ⋅ 3 Baths
Wake up to breathtaking, mile long views of the St. Mary’s River, the Potomac River, and St. George’s Creek from this beautiful three-level waterfront home. Designed with a bright, open floor plan, this residence offers a great floorplan for everyday living and effortless entertaining. Step outside onto the expansive 42-foot Trex deck overlooking the water — an ideal setting for gatherings, sunsets, and peaceful mornings. Inside, the light-filled kitchen features white cabinetry, granite countertops, stainless steel appliances, and a large center island perfect for cooking and conversation. The spacious main-level primary suite provides a private retreat with an upgraded tile bath, soaking tub, oversized tile shower, and double vanities. Hardwood floors enhance the main living areas, while the upper level offers two generously sized bedrooms and a full bath. The lower level includes a two-car garage with abundant workshop and storage space. Outdoors, enjoy your private beach on parcel 175 that conveys with the sale and offers the ideal location to build your private pier.

16386 Ball Point Rd, Piney Point

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169
$760,000
5 Beds ⋅ 4 Baths
Here is your chance! Available for showing starting on 7/31/26! This expansive Cape Cod style home is a once in a lifetime find. Perfect for a farmette or luxurious retreat on 4.51 acres and no HOA. Enjoy a delicious nectarine from one of the many fruit trees while relaxing by your inground pool. The back yard features extensive hardscaping, mature landscaping and a fully fenced in yard. A gas fire feature and full shaded pergola set the scene for a perfect backyard get together. No need for a portable propane tank for your grill either. There is a built in hook up. Watch storms roll in from your wrap around porch complete with outdoor ceiling fans. Do you have a boat or camper? The extra tall garage with workshop and storage can accommodate both. This is a multigenerational home as it features a full in-law suite upstairs with a separate entrance/ exit through the garage. There is a renovated kitchen with updated appliances and beautiful counter top. One full room could be used as a bedroom or office. This space is perfect for a home business as well. Upstairs you will find three large bedrooms and another that could be used as a bedroom or pass through to the office area. For your convenience, there is a stackable laundry upstairs and one located on the main level as well. Both upstairs bathrooms are tastefully renovated one featuring quartz vanity tops and high end fixtures with custom cabinetry and builtins. On the main level the star of the show is the beautifully refreshed kitchen complete with a extra large fridge, sleek custom microwave, extra large, deep sink, granite countertops, huge gas range and additional custom cabinetry/ bar area in the dining area. Check out the sunroom complete with custom sliding Pella doors, new casement and sliding windows from the Simonton Platinum series, featuring special UV tinting. Since all the windows and most doors have been updated you will enjoy an energy efficiency that not every home has. Additionally, there is a ceramic-coated, iron, ventless, woodstove-style fireplace with a remote control on the sunroom. The carpet in the living room is new and the custom built ins elevate your living space. Last but certainly not least is the first floor primary bedroom featuring an ensuite super luxury bath. The master bath features large custom illuminated mirror with remote, oversized walk-in 2-person shower with dual showerheads, custom cherry cabinets with his and hers vanity, private water closet with Toto bidet autoflush toilet. Tile flooring is installed throughout the bathroom and closet area. Motorized shades included as well as the porch swing and pool furniture. Schedule your showing now!

27075 Widow Ln, Mechanicsville

Listing courtesy of JPAR Real Estate Professionals. Contact: 3016844895
$1,700,000
5 Beds ⋅ 4 Baths
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. Mary’s County’s 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 and entertaining. The saltwater pool is finished with premium Wet Edge Premier Stone and Artistic Paver tiles, (featuring embedded seashells sourced from Miami). The tanning ledge measures approximately 8x16' providing the perfect place to lounge and enjoy waterfront views, while a diving board adds to the fun. A dedicated pool pump house and separate dual pool storage unit with its own half bath supports the pool operation. Water enthusiasts will appreciate the exceptional marine amenities. Walking down the hill from the residence leads to a private boathouse and pier system designed with serious boaters in mind. The pier features new stringers, updated power and water service, two slips including the boathouse, and one open slip, a fish cleaning station, and kayak launch area. Low water depth at the end of the pier averages approximately eight feet, making this deep-water location highly desirable for larger vessels and year-round boating. The boathouse, along with the pier, pool house, and detached garage, are all serviced through a dedicated electrical panel system. Water is also available on the pier. Inside, the home has undergone substantial improvements over the years, including a complete transformation of the kitchen and dining areas, creating a stunning gourmet gathering space that serves as the heart of the home. Updated Andersen windows, updated flooring, fresh interior paint, and a beautifully finished laundry and utility room further enhance the home’s appeal. The impressive enclosed sunroom, encompassing approximately 440 square feet, offers year-round enjoyment and flexible living space while showcasing the property’s incredible waterfront views in all seasons. Additional improvements include HardiePlank fiber cement siding, a whole-house generator capable of operating the kitchen and well systems during outages, and a detached 2.5-car garage with a raised floor to improve site grading. The garage offers exceptional storage and future potential for additional finished space should a buyer desire to build up. The well is approximately eight years old. When drilled, the well and pump were upgraded to provide for the additional water needs of the pool, pier and future lawn irrigation. The laundry and utility area features a Navien boiler installed in 2016, providing domestic hot water as well as support for the home’s heating systems. For added value and future convenience, the sellers are in the process of connecting the property to public sewer, which is available within the property. We cannot wait for you to come see the lifestyle that Combs Creek Way has to offer you.

40115 Combs Creek Way, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169
$550,000
3 Beds ⋅ 2 Baths
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 relaxing by the water. The property also features a private dock, crab/oyster shack, and a large storage/workshop building near the front of the property, offering excellent space for tools, equipment, hobbies, waterfront gear, or future possibilities. Located near St. Catherine Island and Bullock Island, this property combines renovated living space, guest accommodations, usable land, private dockage, and memorable water views in one truly special creekside setting. Schedule your showing and experience the waterfront lifestyle for yourself.

37526 River Springs Rd, Avenue

Listing courtesy of Innovation Properties, LLC. Contact: 7037824422
$609,000
3 Beds ⋅ 3 Baths
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 and less than two miles from the breathtaking Chaptico Warf! 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! You will have peace of mind living in this NEW home and all it offers, including: completely conditioned & sealed crawl space; new septic; and new well pump just installed! This is a must see, one of kind home located in the best hidden gem of St. Mary's County; a rare opportunity to own new construction in Chaptico. Final touches are being completed over the next couple of weeks and E&O, septic certification and water certification forthcoming. Do NOT miss this one!

23690 Maddox Rd, Chaptico

Listing courtesy of RE/MAX Realty Group. Contact:

$369,900
3 Beds ⋅ 2 Baths
OWNER FINANCING AVAILABLE, no banks, call for details. Beautifully renovated rambler located in the highly desirable Leonardtown School District, offering the perfect blend of modern updates and peaceful living on almost 1-acre lot. This move-in ready home features 3 bedrooms and 2 full bathrooms, along with a 1-car garage as well as man cave, workshop, or bonus space. The home has been thoughtfully updated with a brand new roof, new windows, new flooring throughout, a fully renovated kitchen with new appliances, and beautifully updated bathrooms, new water heater providing both style and peace of mind. Additional improvements include a new HVAC system to be installed, ensuring comfort and efficiency for the new owner. Enjoy easy single-level living with plenty of outdoor space, ideal for relaxing, entertaining, or future expansion. No HOA. Conveniently located near Leonardtown amenities, shopping, dining, and schools.

21983 Point Lookout Rd, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009
$649,900
5 Beds ⋅ 2 Baths
Welcome to your waterfront escape on the point of St. George Island, where the Potomac River meets the Chesapeake Bay. This home was built by the local Amish community for this family. This rare offering features 154 feet of riprapped shoreline, delivering sweeping water views and front-row seats to breathtaking sunrises, passing boats, and endless coastal serenity. The main home offers 4 bedrooms and 1.5 baths, with water views from both the kitchen and living room, creating a daily backdrop that never gets old. The updated kitchen features granite countertops and an eat-in area, perfect for casual dining while overlooking the water. A wraparound screened porch invites you to relax, entertain, and enjoy the bay breeze in every season. For boating enthusiasts, the property is fully equipped with a private pier, electric, and boat lift, making it easy to get out on the water at a moment’s notice. Additional features include: Detached garage with apartment above and full bath – ideal for guests, rental income, or private workspace Carport and shed for added storage and functionality New HVAC systems in both the main home and garage Public sewer recently installed (approx. $48,000 investment) Deep well .36-acre lot with mature fruit trees Whether you're looking for a full-time residence, weekend retreat, or income-producing opportunity, this property offers the perfect blend of waterfront living, versatility, and long-term value. Opportunities like this—on the point, with this much frontage—don’t come around often.

16104 Piney Point Rd, Piney Point

Listing courtesy of Samson Properties. Contact: 4439757555
$729,900
6 Beds ⋅ 3 Baths
Are you finding yourself longing for a peace and quiet that only life on the water can bring? Come home to stargazing without light pollution, dinner on the patio watching osprey, herons and geese in the creek. Spend your weekends boating, fishing, crabbing on the pier or taking long walks with both water and farm views. Invite your friends and family because this home has 6 bedrooms and 3 bathrooms with a floorplan perfect for a multi family living situation or even a vacation rental. The first floor living room is both cozy with the fireplace and also fun with the bar area and room to dance or game. You'll love the natural light coming into the kitchen with expansive windows bringing the creek views as close as you can get without stepping outside. So much granite counter space especially with the mobile island, newer appliances, an undermount sink, appliance garage and desk space might just make this your favorite room of the house. Whether you're having elaborate formal meals or casual fare, the dining room seats as many as you want and a fireplace and amazing views to top it off. Completing the main level are 2 spacious bedrooms, a full bath and laundry room with a 2nd shower. You'll also appreciate the side entrance of the home that open to a large entryway currently used as a library that can double as an office with access to the 2nd level leading to another primary bedroom, ensuite bathroom with soaking tub and separate shower. Plus 3 additional bedrooms, 3rd full bath and common space where you'll discover the spiral staircase taking you back to the lower living room. Plenty of parking with 2 paved driveways, a sideload attached garage and 2nd single car garage/shed plus another shed for storage. The covered front porch brings you panoramic views of a farm and woods where wildlife roam. The side and backyard have unobstructed views of St. Jerome Creek where you can dock your boat or launch your kayak with easy quick access to the Chesapeake Bay. Ridge is just far enough away from the hustle and bustle but still close enough to shopping and commuting. Locally you'll enjoy the waterfront restaurants, farmstands and state park. Just a few minutes to historic St. Marys City and St. Marys College.

49716 Airedele Rd, Ridge

Listing courtesy of RE/MAX One. Contact: 4105356291
$499,000
3 Beds ⋅ 3 Baths
PRICE IMPROVEMENT NEW 30 YEAR Roof Completely renovated 3BR/2.5BA Cape Cod with attached garage. This move-in ready home features engineered hardwood flooring, custom crown molding, and faux wood blinds throughout. The updated kitchen includes granite countertops and new stainless steel appliances. Bathrooms offer custom tiled, upgraded showers. Additional features include ceiling fans, high-end chandelier lighting, and upgraded ambient lighting. Functional layout with modern finishes throughout. Seller has a recent appraisal available indicating a value above the list price.

30150 Huntt Rd, Mechanicsville

Listing courtesy of RE/MAX One. Contact: 4437718009
$1,750,000
4 Beds ⋅ 2 Baths
Welcome to Bayside Road. Residents of Leonardtown believe this is THE place to live. This is a beautiful, well-maintained waterfront farm that is located a few minutes from historic Downtown Leonardtown. When you enter the property gates, you will see the most beautiful canopy of trees leading you through the whole farm. The Charming Cape Cod house is situated on 48.9 acres of gorgeous land. The house is well-kept with 4 Bedrooms and 2 Baths; a place-to-relax front porch; the master bedroom and the laundry room (washer and dryer included) are on the entry level. Also, a foundation for a 3,000+ square-foot house has been started near the water and has the electric meter installed. A pier on the farm is on the protected Cecil Creek where boaters and non-boaters can enjoy the tranquility and hours of fishing, crabbing, and just enjoying life. If it's hunting you want, many deer, turkeys, ducks and other waterfowls have been sighted on this sportsman's paradise. A 24-Hour Appointment Notice is necessary for all showings. To show/view the house, call the Listing Agent who will schedule an appointment for/with you.

Bayside Rd, Leonardtown

Listing courtesy of Haley Family Realty. Contact:

$499,000
3 Beds ⋅ 2 Baths
JUST REDUCED THIS IS A DEAL = THIS 3 BEDROM 1 1/2 BATH CAPE COD NEEDS A LITTLE WORK ITS WATERFRONT ON INDIAN CREEK WITH A PIER.

30087 Cross Woods Dr, Mechanicsville

Listing courtesy of Elrod & Associates Real Estate, Inc. Contact: