4,343

St Marys, MD Homes

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  • /33

    $450,000

    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft

    20798 Waterside Dr, Leonardtown, MD 20650

    Investor Alert! Stunning Waterfront Opportunity on the Potomac River. Discover the perfect 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 living—whether it’s

    Agent Photo

    Connie Fitzgerald

    RE/MAX Closers

    (240) 376-2980

    20798 Waterside Dr, Leonardtown, MD 20650
  • /13

    $2,300 per month

    • 3 Beds
    • 2 Baths
    • 1,176 Sq Ft
    • House for Rent

    18145 Piedmont Dr, Cobb Island, MD 20625

    Property Id: 19441643 bedrooms, 2 baths. Detached 24x24 garage, LVT flooring throughout, laundry room with w/d included, new appliances, back deck, fresh paint throughout interior/exterior. Quiet location on dead end street. Water-oriented community. One year lease. Tenant responsible for all utilities. NO smoking. One small/medium pet subject to approval by landlord, and non-refundable

    18145 Piedmont Dr, Cobb Island, MD 20625
  • /10

    $143,500 Sold Aug 01, 2025

    • Land
    • 1.60 Acres
    • $89,688 per Acre
    • 4 Days On Market

    20668 Abell Rd, Abell, MD 20606

    Discover your own slice of coastal serenity with this rare raw land offering nestled along the tranquil waters of the bay. Whether you're a builder, visionary, or nature enthusiast, this bayfront gem offers a blank canvas with endless possibilities. Don't miss the chance to bring your vision to life in one of the area's most peaceful waterfront settings.

    Amy Scott OE Realty

    20668 Abell Rd, Abell, MD 20606
    • /3

      Not Listed For Sale

      23104 Upland Dr, Bushwood, MD 20618

      23104 Upland Dr, Bushwood, MD 20618
  • /2

    $35,000

    • Land
    • 0.23 Acre
    • $152,174 per Acre

    36764 Roberto Dr, Bushwood, MD 20618

    Raw Land only - Comes with community amenities, utilize for temporary Rv site with water access, additional lot conveys

    Agent Photo

    Rhonda Darden

    Cooperative Real Estate Maryland, LLC

    (240) 226-3669

    36764 Roberto Dr, Bushwood, MD 20618
  • /65

    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    18216 Piedmont Dr, Cobb Island, MD 20625

    REAL ISLAND LIVING.right here in Southern Maryland. Turn Off of Major Highway passing corn and soybean fields, Historic Mount Republic, Swan Point Golf Course & Club and then Cross the Bridge to the Isle of Cobb surrounded by the Potomac River on One Side and Neale Sound on the Other. Both Bodies Merge at the Wicomico River. This Modern Rambler features Extraordinary Outdoor Living Spaces

    Mary C Stokely CENTURY 21 New Millennium

    18216 Piedmont Dr, Cobb Island, MD 20625
  • /76

    $1,037,500 Sold Jul 31, 2025

    • 2,296 Sq Ft
    • $452/SF
    • 13 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2004

    13450 Hill Rd, Newburg, MD 20664

    Check out the aerial drone video attached to this listing. A one of a kind waterfront home with breath taking views all around and over 731 linear feet of waterfront! This Spectacular 1.82 acre waterfront property is surrounded by water on 3 sides with 3 private piers . Sit out on the (low maintenance trex) 8 foot deep covered porch that wraps around the entire home to take in the expansive

    Mike Petras Veterans USA Realty

    13450 Hill Rd, Newburg, MD 20664
    • /46

      Est $467,234 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,184 Sq Ft

      40077 Big Chestnut Rd, Clements, MD 20624

      40077 Big Chestnut Rd, Clements, MD 20624
  • /67

    $577,000

    • 2 Beds
    • 1.5 Baths
    • 2,112 Sq Ft

    37420 River Springs Rd, Avenue, MD 20609

    Unique waterfront property w/ guest house. New dock, w/ 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 w/ lots of light and water views. 2 BR, 1.5 bath and bonus

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (240) 896-3491

    37420 River Springs Rd, Avenue, MD 20609
  • /14

    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft
    • House for Rent

    17469 Audrey Rd, Cobb Island, MD 20625

    Beautiful one level living on Cobb Island. Home boasts 3 bedrooms with 2 full baths. Has an extra room that can be a bedroom or office. New Carpet, Fresh Paint, New kitchen cabinets. Fully fenced in yard. Tenants are responsible for all utilities and lawn maintenance. Pets are a case by case. Security Deposit 2200.00 and first months rent are due at lease signing.

    Michelle Snider OE Realty

    17469 Audrey Rd, Cobb Island, MD 20625
  • /50

    $406,000 Sold Jul 25, 2025

    • 984 Sq Ft
    • $413/SF
    • 19 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1978

    23745 Hicks Dr, Leonardtown, MD 20650

    Welcome to 23745 Hicks Drive, a thoughtfully updated rambler on over half an acre in the quiet Holly Oaks neighborhood of Leonardtown. With a spacious detached garage, a finished basement, and recent renovations throughout, this home offers comfort, functionality, and a great location—all with no HOA.Inside, you’ll find a bright and open layout featuring wide plank flooring, recessed

    Neil Smith Blackwell Real Estate, LLC

    23745 Hicks Dr, Leonardtown, MD 20650
    • /31

      Est $491,470 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,400 Sq Ft

      24220 Victory Ln, Clements, MD 20624

      24220 Victory Ln, Clements, MD 20624
  • /96

    $1,300,000

    • 6 Beds
    • 3.5 Baths
    • 5,888 Sq Ft

    23155 Greenstone Dr, 3, Leonardtown, MD 20650

    Luxury, Space, and Sophistication – All in One Remarkable Property! Prepare to be impressed by this meticulously maintained almost 7,000 sq ft estate—a rare gem that blends luxury, comfort, and functionality in every detail. If your current home lacks character or space, this extraordinary residence will exceed all your expectations! Interior Highlights: • Gourmet Kitchen with oversized island,

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (240) 387-9601

    23155 Greenstone Dr, 3, Leonardtown, MD 20650
  • /15

    $2,350 per month

    • 4 Beds
    • 2.5 Baths
    • 1,380 Sq Ft
    • House for Rent

    39870 Lady Baltimore Ave, Leonardtown, MD 20650

    Charming Rambler in Water-Access Community – Available Now!Enjoy easy one-level living in this adorable 4-bedroom, 2.5-bath rambler nestled in the St. Clements Shores community. With access to St. Clements Bay, you'll love spending time outdoors in the spacious yard with mature trees, a large deck, and peaceful surroundings.Inside, the open-concept layout offers great flow for

    Lesa Clark Redfin Corp

    39870 Lady Baltimore Ave, Leonardtown, MD 20650
  • /85

    $439,000 Sold Jul 11, 2025

    • 3,466 Sq Ft
    • $127/SF
    • 54 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1967

    18855 Wicomico River Dr, Cobb Island, MD 20625

    Looking for coastal living and small town charm? This home is nestled in the serene beauty of Cobb Island, this charming Cape Cod boasts nearly 3,500 sq. ft. of finished living space, offering a perfect blend of comfort and style. Relax on the expansive front porch and take in the stunning water views visible from many rooms throughout the home. Ideal for entertaining, the open floor plan

    Christy Gartland CENTURY 21 New Millennium

    18855 Wicomico River Dr, Cobb Island, MD 20625
    • /28

      Est $508,760 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,368 Sq Ft

      22301 Bayside Rd, Leonardtown, MD 20650

      22301 Bayside Rd, Leonardtown, MD 20650
  • /39

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,326 Sq Ft

    22801 Pleasant Ln, Maddox, MD 20621

    ALMOST like a new build with this completed renovation. New interior walls, new plumbing, new electric, new appliances, new HVAC, new siding, and new floors all in the last year. New floor joists and crawl space moisture barriers. AND one of the highlights is the WATER ACCESS via the community water access point. Its a 3bedroom 2bath, open floor concept, in the Longview Beach Association. Come

    Agent Photo

    Amanda Scott

    Real Broker, LLC

    (240) 693-3429

    22801 Pleasant Ln, Maddox, MD 20621
  • /37

    $410,000 Sold Jul 03, 2025

    • 1,438 Sq Ft
    • $285/SF
    • 61 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2006

    13595 Hayden Flick Place, Newburg, MD 20664

    Waterfront Retreat with Private Pier, Boat Slips & Boathouse – Turnkey & ReadySpacious and serene, this waterfront property on Neale’s Creek offers direct access to the Potomac River and an exceptional lifestyle for boaters and nature lovers alike. Enjoy 4 deep water slips, a 10,000 lb boat lift, and a private boathouse with a 200-amp panel and separate meter—perfect for serious maritime

    Tanya Redding CENTURY 21 New Millennium

    13595 Hayden Flick Place, Newburg, MD 20664
    • /30

      Est $768,423 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,736 Sq Ft

      40630 Breton Oaks Ln, Leonardtown, MD 20650

      40630 Breton Oaks Ln, Leonardtown, MD 20650
  • /38

    $640,000

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft

    12498 Neale Sound Dr, Cobb Island, MD 20625

    Expansive panoramic views of the Neale Sound and Wicomico River. Almost 2000 sq ft cottage in Cobb Island located in a secluded area with lots of privacy. House is much bigger inside and NOT IN FLOOD ZONE. House features 4 bedrooms, 2 full bathrooms and many recent upgrades! Main level has Kitchen, Living room, and Dining Room with an open concept design, 2 bedrooms, 1 full bath and laundry

    Yeewen Chang Evergreen Properties

    12498 Neale Sound Dr, Cobb Island, MD 20625
  • /70

    $625,000 Sold Jul 02, 2025

    • 3,664 Sq Ft
    • $171/SF
    • 69 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1997

    21897 Fairway Dr, Leonardtown, MD 20650

    Qualified VA buyers using their own entitlement can assume the current 2.25% VA loan.Custom-Built Beauty Overlooking Breton Bay Golf Course! Welcome to 21897 Fairway Drive, Leonardtown, MD—a stunning 5-bedroom, 2.5-bath custom-built home in the desirable Breton Bay community. This home is in impeccable condition with numerous upgrades—simply move right in and start enjoying luxury

    Matthew Burgan Infinitas Realty Group

    21897 Fairway Dr, Leonardtown, MD 20650
    • /24

      Est $314,546 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,502 Sq Ft

      20284 Park Place, Coltons Point, MD 20626

      20284 Park Place, Coltons Point, MD 20626
  • /80

    $825,000

    • 4 Beds
    • 3.5 Baths
    • 2,442 Sq Ft

    39825 Sweetpea Ln, Leonardtown, MD 20650

    Waterfront serenity awaits! Nestled on 3.59 private acres along Tennyson Creek with 300 feet of water frontage, this 4-bedroom, 3.5-bath home offers peace, privacy, and panoramic views. Inside, you'll find 2,408 square feet of comfortable living space featuring a cozy fireplace, wood stove, and large windows that invite the beauty of the outdoors in. The expansive deck is perfect for entertaining

    Mary Helen Wiley Daly RE/MAX One

    39825 Sweetpea Ln, Leonardtown, MD 20650
  • /11

    $340,000 Sold Jun 27, 2025

    • 2,059 Sq Ft
    • $165/SF
    • 6 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2004

    38897 Viewriver Dr, Bushwood, MD 20618

    Welcome to your dream home! This beautifully maintained rambler features 4 spacious bedrooms and 2 full bathrooms, great for families seeking additional space. The kitchen has been updated with stainless steel appliances and granite countertops. It is located within the Longview Beach community, which is a water access community with features such as a boat ramp, pier, beach, playground,

    Sabrina Reed Coldwell Banker Realty

    38897 Viewriver Dr, Bushwood, MD 20618
    • /41

      Est $880,055 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,021 Sq Ft

      23160 Greenstone Dr, Leonardtown, MD 20650

      23160 Greenstone Dr, Leonardtown, MD 20650
  • /82

    $505,000

    • 2 Beds
    • 2 Baths
    • 1,376 Sq Ft

    20395 Bowles Rd, Coltons Point, MD 20626

    Welcome to Bowles Road Your Private Waterfront Retreat!Nestled on .85 acres of serene, natural beauty, this special property offers a rare opportunity to enjoy a true beachfront lifestyle. From the moment you arrive, you’re surrounded by nature and tranquility. Throughout the seasons, you’ll witness an abundance of wildlife right in your backyard – from graceful bald eagles and osprey to

    Jessica Raley CENTURY 21 New Millennium

    20395 Bowles Rd, Coltons Point, MD 20626
  • /17

    $685,000 Sold Jun 20, 2025

    • 2,748 Sq Ft
    • $249/SF
    • 2 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 1967

    21821 Cove Ln, Leonardtown, MD 20650

    Choice location, private point on Cherry Cove with outstanding views of Cherry Cove & Breton Bay. Solid brick rambler with lots of options; generous office could easily be converted into 3rd bedroom....sun room, family room and formal living room with fireplace. Home needs updating. A stunning, private, convenient location!

    Barbara Stellway KW Metro Center

    21821 Cove Ln, Leonardtown, MD 20650
    • /4

      Est $139,909 Not Listed For Sale

      36724 Vaughn Dr, Bushwood, MD 20618

      36724 Vaughn Dr, Bushwood, MD 20618
  • /38

    $435,000

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft

    12350 Neale Sound Dr, Cobb Island, MD 20625

    Charming single-family residence offering 1,444 square feet, 3 bedrooms, and 2 full bathrooms with water views of Neale Sound on picturesque Cobb Island. Step inside to a spacious and open main level, where vaulted ceilings and dual ceiling fans enhance the bright and airy combined living and dining room. This inviting space flows into a cozy sunroom with views of the garden and the water, along

    Bob Lucido Keller Williams Lucido Agency

    12350 Neale Sound Dr, Cobb Island, MD 20625
  • /25

    $281,000 Sold Jun 18, 2025

    • 818 Sq Ft
    • $344/SF
    • 31 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1957

    17585 Oriole Dr, Cobb Island, MD 20625

    Welcome to 17585 Oriole Dr, nestled in the charming waterfront community of Cobb Island! This beautifully updated home sits on a spacious double lot and features stainless steel appliances, hardwood floors, granite countertops, and a custom tile shower. Enjoy energy-efficient windows and roofing, elegant crown molding, and a roomy utility space—all surrounded by mature pine trees. The paver

    William Rabbitt The Southside Group Real Estate

    17585 Oriole Dr, Cobb Island, MD 20625
    • /30

      Est $434,345 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,280 Sq Ft

      36789 Dannys Ln, Chaptico, MD 20621

      36789 Dannys Ln, Chaptico, MD 20621
  • /36

    $499,000

    • 1 Bed
    • 1 Bath
    • 392 Sq Ft

    39020 Sonnie Way, Clements, MD 20624

    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

    Julie Fuller EXP Realty, LLC

    39020 Sonnie Way, Clements, MD 20624
  • /51

    $415,000 Sold Jun 09, 2025

    • 1,348 Sq Ft
    • $308/SF
    • 48 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1994

    39880 Lady Baltimore Ave, Leonardtown, MD 20650

    Introducing this beautiful 3 Bedroom 2 Full Bath Rambler in Leonardtown. Some updates in this beautiful home include new vinyl flooring throughout, the Roof was replaced in 2019, the appliances are less than 2 years old, the Heat Pump was replaced in 2020, and much much more!This home features a huge pantry in the kitchen, a huge laundry room with even more cabinets for storage, a beautiful

    Matthew Burgan Infinitas Realty Group

    39880 Lady Baltimore Ave, Leonardtown, MD 20650
    • /8

      Est $126,500 Not Listed For Sale

      36724 Fielding Dr, Chaptico, MD 20621

      36724 Fielding Dr, Chaptico, MD 20621
  • /71

    $440,000

    • 3 Beds
    • 2.5 Baths
    • 2,105 Sq Ft

    36898 Bushwood Wharf Rd, Bushwood, MD 20618

    Embrace rural tranquility on this 1-acre St. Mary's County retreat, just moments from the Wicomico River's boating, fishing, and crabbing opportunities and , right at the Wharf, savor delicious meals at the restaurant . Enjoy the freedom of no HOA to craft your Baywise-certified paradise while staying conveniently close to Leonardtown’s amenities and major commuter routes to Pax River NAS,

    Beverly Aldridge Coldwell Banker Jay Lilly Real Estate

    36898 Bushwood Wharf Rd, Bushwood, MD 20618
  • /27

    $285,000 Sold Jun 06, 2025

    • 900 Sq Ft
    • $317/SF
    • 3 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1969

    36786 Wilson Dr, Bushwood, MD 20618

    Welcome to 36786 Wilson Dr. - your completely reimagined haven awaits. Nestled in a peaceful neighborhood, this turnkey home blends modern comforts with move-in readiness. Every major system has been thoughtfully upgraded so you can relax and enjoy. Brand New Kitchen cabinetry, countertops and fixtures and a completely updated bathroom offers buyers the style and function they crave. Beautiful

    Zachary Wyvill RE/MAX United Real Estate

    36786 Wilson Dr, Bushwood, MD 20618
    • /35

      Est $538,731 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,920 Sq Ft

      24520 Budds Creek Rd, Clements, MD 20624

      24520 Budds Creek Rd, Clements, MD 20624
  • /47

    $775,000

    • 4 Beds
    • 3.5 Baths
    • 1,962 Sq Ft

    20938 Olen Mattingly Rd, Avenue, MD 20609

    This Cape Cod is located on a 1-acre waterfront lot on Saint Patrick's Creek. Bring the boat! It's the perfect location for boosting in the sun, fishing, and crabbing. It has an extensive pier and floating dock that was recently resurfaced w/ marine pressure-treated timber. It spacious with 4 Bedrooms 3.5 Baths. The home features two main-level master bedrooms with ensuite bathrooms. The

    Thomas Hennerty NetRealtyNow.com, LLC

    20938 Olen Mattingly Rd, Avenue, MD 20609
  • /75

    $359,750 Sold Jun 02, 2025

    • 1,440 Sq Ft
    • $250/SF
    • 6 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2000

    17420 Audrey Rd, Cobb Island, MD 20625

    Discover the charm of island living at 17420 Audrey Rd, nestled in the heart of Cobb Island, MD. This well-kept home offers a perfect blend of comfort and convenience, just moments from local restaurants and water access. Inside, you'll find two spacious bedroom suites, each providing a private retreat with ample space and natural light. The outdoor space is just as inviting, featuring a large

    The Burks-Sutten Team CENTURY 21 New Millennium

    17420 Audrey Rd, Cobb Island, MD 20625
    • /54

      Est $357,333 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,016 Sq Ft

      23170 Longview Blvd, Bushwood, MD 20618

      23170 Longview Blvd, Bushwood, MD 20618

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