6,693

St Marys, MD Homes

Section Image
  • /59

    $612,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,946 Sq Ft

    43571 Bayberry Ct, Leonardtown, MD 20650

    Gorgeous Colonial on a Beautifully Landscaped 4.26 Acre Premium Lot in the Sought After, Well-Established Neighborhood of Chestnut Ridge. A Welcoming Covered Front Porch leads to an Open Floor Plan with 9 Foot Ceilings and New Luxury Vinyl Plank (LVP) Flooring. Stylish Large Living Room with a Wood Burning Fireplace. Bright Kitchen with 48” Cabinetry, Gleaming Granite, and a Large Pantry. The

    Jenny Norris EXP Realty, LLC

    43571 Bayberry Ct, Leonardtown, MD 20650
  • /42

    $740,000 Sold Feb 03, 2025

    • 5,716 Sq Ft
    • $129/SF
    • 13 Days On Market
    • 6 Beds
    • 5 Baths
    • Built 2006

    41041 Knight Rd, Leonardtown, MD 20650

    This stunning estate is a true masterpiece, set on multiple acres of lush, meticulously landscaped grounds in one of the most sought-after neighborhoods. Boasting expansive living spaces both inside and out, this home offers unparalleled luxury and privacy. The sprawling property provides a sense of serenity and seclusion, yet remains conveniently close to top-tier schools, local beaches, and

    Connie Gunn CENTURY 21 New Millennium

    41041 Knight Rd, Leonardtown, MD 20650
    • /54

      Est $583,865 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,982 Sq Ft

      23285 Jenifer Ct, Leonardtown, MD 20650

      23285 Jenifer Ct, Leonardtown, MD 20650
  • /40

    $615,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 3,061 Sq Ft

    20591 Chestnut Ridge Dr, Leonardtown, MD 20650

    Welcome to this well-built colonial in the picturesque Chestnut Ridge neighborhood!With over 3,000 finished square feet, 5 bedrooms, and 3.5 bathrooms, this home is full of charm, character, and thoughtful craftsmanship.Situated on 2.11 acres, the home features a classic brick exterior, a welcoming front porch, and a spacious two-car garage. Inside on the main level, you'll find two

    Lauren Garner EXP Realty, LLC

    20591 Chestnut Ridge Dr, Leonardtown, MD 20650
  • /47

    $375,000 Sold Jan 30, 2025

    • 2,286 Sq Ft
    • $164/SF
    • 10 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1989

    40459 Breton View Dr, Leonardtown, MD 20650

    Welcome to this charming 3-level end-unit townhouse in Breton Bay! Step inside to an open floor plan and unwind by the cozy wood-burning fireplace. Enjoy the screened-in porch or host a BBQ on the deck. The home features two primary bedrooms, a dining area, and an island kitchen with a pantry. The lower level, currently used as a recreational room with a closet and full bath, could easily serve

    Chris Norris JR. Topside Realty

    40459 Breton View Dr, Leonardtown, MD 20650
    • /51

      Est $494,490 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,652 Sq Ft

      22152 Breton Woods Ct, Leonardtown, MD 20650

      22152 Breton Woods Ct, Leonardtown, MD 20650
  • /66

    $529,900 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,328 Sq Ft

    22338 White Oak Rd, Leonardtown, MD 20650

    COMING SOON! Beautiful 4 bedroom, 2 1/2 bathroom colonial on over half an acre lot in Breton Bay! This home has has everything you could want with formal living & dining rooms, kitchen w/upgraded counter tops and appliances. The kitchen has bar style seating, a breakfast nook with built in bench and a seating area perfect for morning coffee and enjoying views of the back yard and pool. The

    Kelly Padgett CENTURY 21 New Millennium

    22338 White Oak Rd, Leonardtown, MD 20650
  • /45

    $260,000 Sold Jan 24, 2025

    • 768 Sq Ft
    • $339/SF
    • 19 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1930

    22321 Leonard St, Leonardtown, MD 20650

    Charming Cottage in Water-Privileged St. Clements Bay Discover the serenity of life in this bright and airy cottage, nestled in the sought-after St. Clements Bay community. The home features tasteful updates to the kitchen and bath, blending modern convenience with cozy charm. The level lot includes a fully fenced backyard, perfect for relaxing or entertaining, with a handy shed for extra

    Lesa Clark Redfin Corp

    22321 Leonard St, Leonardtown, MD 20650
    • /72

      Est $578,931 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,520 Sq Ft

      23564 Gunnell Dr, Leonardtown, MD 20650

      23564 Gunnell Dr, Leonardtown, MD 20650
  • /26

    $249,900 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,212 Sq Ft

    21749 Point Lookout Rd, Leonardtown, MD 20650

    Charming Mid-Century Rambler Near St. Mary’s LakeStep into classic mid-century style with this well-maintained rambler, offering timeless charm and solid construction. Featuring hardwood floors throughout, this home boasts larger-than-average bedrooms for its era—providing extra comfort and space rarely found in similar homes.Enjoy morning coffee on the welcoming front porch and

    John Gatton CENTURY 21 New Millennium

    21749 Point Lookout Rd, Leonardtown, MD 20650
  • /73

    $579,900 Sold Jan 14, 2025

    • 3,726 Sq Ft
    • $156/SF
    • 27 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2018

    41431 Osborne Ln, Leonardtown, MD 20650

    Clark's Rest in Leonardtown offers a fantastic blend of convenience, recreation, and elegant living! This vibrant community is centrally located near local shops and dining, and residents enjoy access to impressive amenities, including a clubhouse, a spacious pool with water features and a dedicated kiddie pool, basketball and tennis courts, a tot lot, and playgrounds. Walking and biking trails

    Kimberly Page EXP Realty, LLC

    41431 Osborne Ln, Leonardtown, MD 20650
    • /6

      Est $746,092 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,222 Sq Ft

      41985 White Point Beach Rd, Leonardtown, MD 20650

      41985 White Point Beach Rd, Leonardtown, MD 20650
  • /50

    $540,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,686 Sq Ft

    41412 Doctors Crossing Rd, Leonardtown, MD 20650

    Welcome to your dream home in highly sought-after Clarks Rest, just minutes from all the charm and dining of Leonardtown Square. This vibrant community features sidewalks, a community pool, and that perfect neighborhood feel you’ve been looking for. Step inside to find real hardwood floors in the entryway and luxury vinyl plank flooring throughout the main living areas, including the spacious

    Delaney Burgess RE/MAX United Real Estate

    41412 Doctors Crossing Rd, Leonardtown, MD 20650
  • /44

    $639,900 Sold Jan 10, 2025

    • 3,080 Sq Ft
    • $208/SF
    • 24 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2024

    41541 Fairwood Ct, Leonardtown, MD 20650

    $20,000 SELLER CONCESSIONS TO BUYER!! MARRICK HOMES' PINEHURST IN CLARKS REST! MOVE IN NOW! Includes: Quartz Kitchen Countertops, Luxury Vinyl Planks, Stainless Steel Appliances, UPGRADED Cabinets throughout Kitchen & Baths, Separate Owner's Shower & Soaking Tub in Owner's Bath, and MUCH MORE! Clarks Rest community features an Outdoor Swimming Pool, Tennis Court, Basket Ball Court,

    Lynn Smithburger CENTURY 21 New Millennium

    41541 Fairwood Ct, Leonardtown, MD 20650
    • /28

      Est $348,625 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,292 Sq Ft

      22340 Gore St, Leonardtown, MD 20650

      22340 Gore St, Leonardtown, MD 20650
  • /140

    $775,000 Under Contract

    • 4 Beds
    • 5.5 Baths
    • 6,116 Sq Ft

    41115 Paw Hollow Ln, Leonardtown, MD 20650

    Stunning Brick Front Colonial in Paw Paw Hollow - 1.8 Acres of Private LuxuryWelcome to this well maintained and beautifully designed brick front Colonial in the highly sought-after Paw Paw Hollow. This spacious 4-bedroom, 5.5-bathroom home offers over 5,000 square feet of living space on a generous 1.8-acre lot, providing the perfect blend of comfort, elegance, and privacy.Main Level

    Jennifer Goddard CENTURY 21 New Millennium

    41115 Paw Hollow Ln, Leonardtown, MD 20650
  • /79

    $625,000 Sold Jan 09, 2025

    • 3,129 Sq Ft
    • $200/SF
    • 151 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2010

    23636 Hansel Ct, Leonardtown, MD 20650

    Welcome to your dream home, where modern elegance meets everyday comfort in the highly sought-after community of Leonard's Grant, Leonardtown, MD. This stunning 4-bedroom, 2.5-bathroom home offers an exceptional lifestyle with thoughtfully designed spaces and premium finishes.Step inside to discover gleaming hardwood floors that flow seamlessly through a welcoming and versatile floor

    Chris Hill CENTURY 21 New Millennium

    23636 Hansel Ct, Leonardtown, MD 20650
    • /37

      Est $642,547 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,524 Sq Ft

      41625 Ferber Ct, Leonardtown, MD 20650

      41625 Ferber Ct, Leonardtown, MD 20650
  • /33

    $599,900 Under Contract

    • 5 Beds
    • 4 Baths
    • 3,540 Sq Ft

    23348 Lindsay Dr, Leonardtown, MD 20650

    Seller is offering 3% closing help!Welcome to 23348 Lindsay Drive — where space, style, and comfort come together in the heart of Leonardtown’s sought-after Clark’s Rest community. This nearly new 5-bedroom, 4-bath home offers over 3,500 sq ft of beautifully designed living space with thoughtful upgrades and a flexible floor plan perfect for modern living.Step inside to a

    Christi Turman-Rojas Fairfax Realty Premier

    23348 Lindsay Dr, Leonardtown, MD 20650
  • /52

    $425,000 Sold Jan 08, 2025

    • 2,280 Sq Ft
    • $186/SF
    • 66 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1961

    20400 Chingville Rd, Leonardtown, MD 20650

    Buyer got cold feet! BACK ON THE MARKET! Discover your future at this picturesque property, set on a stunning 2 acre lot that feels like your own private park. With a freshly paved driveway and a beautiful stamped concrete walkway, this home is perfect for outdoor entertaining, relaxing with a good book, or hosting gatherings. Inside, this adorable two-level home has been completely updated from

    Delaney Burgess RE/MAX United Real Estate

    20400 Chingville Rd, Leonardtown, MD 20650
    • /11

      Est $337,025 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,232 Sq Ft

      22249 Archer St, Leonardtown, MD 20650

      22249 Archer St, Leonardtown, MD 20650
  • /5

    $497,500 Under Contract

    • 3 Beds
    • 3 Baths
    • 2,952 Sq Ft

    25365 Point Lookout Rd, Leonardtown, MD 20650

    Unique property : Residential AND Commercial !!! Both are presently rented. The two story home has 3 bedrooms, one bath, replaced furnace, window AC units, storage, partial unfinished basement. Needs updating. The former Doctor's office has had some updating recently. New heat pump last year. Both are on separate electric meters, heating and cooling systems. Ample parking behind building for both

    Jan Barnes CENTURY 21 New Millennium

    25365 Point Lookout Rd, Leonardtown, MD 20650
  • /63

    $420,000 Sold Jan 07, 2025

    • 2,896 Sq Ft
    • $145/SF
    • 11 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2014

    23255 Lindsay Dr, Leonardtown, MD 20650

    Discover modern living at its finest in this stunning, fully finished three-level townhouse in the heart of Leonardtown! This meticulously maintained home features a bright, open floor plan with the main level designed for easy gatherings. Enjoy beautiful hardwood floors throughout the main level, along with a sleek kitchen showcasing granite countertops, stainless steel appliances, and upgraded

    Jessica Raley CENTURY 21 New Millennium

    23255 Lindsay Dr, Leonardtown, MD 20650
    • /67

      Est $600,145 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,916 Sq Ft

      23626 Abraham Dr, Leonardtown, MD 20650

      23626 Abraham Dr, Leonardtown, MD 20650
  • /7

    $772,000 Under Contract

    • 4 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    44798 Medleys Neck Rd, Leonardtown, MD 20650

    Other lots in the area, call us to discussTBB - Custom Home - Many other floor plans and locations - call to discuss

    Marie Jozwik RE/MAX Realty Group

    44798 Medleys Neck Rd, Leonardtown, MD 20650
  • /24

    $440,000 Sold Dec 30, 2024

    • 2,242 Sq Ft
    • $196/SF
    • 0 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1972

    40808 S 40 Dr, Leonardtown, MD 20650

    Charming contemporary rambler with a full basement, offering seasonal views of Breton Bay. The main level boasts an open living/dining area, a remodeled kitchen with new granite countertops (2024), and luxury vinyl plank flooring throughout. Recent updates include a new roof (2019), HVAC (2021), oil tank (2018), and gutters with leaf guards (2021). The home features replacement windows and added

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    40808 S 40 Dr, Leonardtown, MD 20650
    • /88

      Est $607,977 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,828 Sq Ft

      23689 Jm Gough Ct, Leonardtown, MD 20650

      23689 Jm Gough Ct, Leonardtown, MD 20650
  • /2

    $1,740,000 Under Contract

    • Land
    • 3.85 Acres
    • $451,948 per Acre

    25845 Point Lookout Rd, Leonardtown, MD 20650

    This listing is 3.85 acres of a total 6-acre commercial property in Leonardtown, Maryland. Don't miss the chance to invest in this thriving and picturesque community. Whether you're looking to create a retail haven, upscale office space, or a dining destination, this property has all the ingredients for success. With its size and location near Patuxent Naval Air Station, this property is a blank

    Anne Davis CENTURY 21 Commercial New Millennium

    25845 Point Lookout Rd, Leonardtown, MD 20650
  • /91

    $525,000 Sold Dec 20, 2024

    • 3,602 Sq Ft
    • $146/SF
    • 1 Day On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1990

    21733 Pinehurst Ct, Leonardtown, MD 20650

    Delightful, comfortable home with lots of upgrades, situated on a nice corner lot in a great neighborhood! All the spaces you need: living and family rooms, both with handsome stone fireplaces (one wood, one propane); remodeled kitchen with white cabinetry, gorgeous Brazilian granite countertops, and eating area; separate dining room with bay window. Hardwood flooring & ceramic tile, ceiling

    Patrick Deighan CENTURY 21 New Millennium

    21733 Pinehurst Ct, Leonardtown, MD 20650
    • /43

      Est $557,533 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,100 Sq Ft

      21081 Rosebay St, Leonardtown, MD 20650

      21081 Rosebay St, Leonardtown, MD 20650
  • /37

    $510,000 Sold Dec 20, 2024

    • 2,764 Sq Ft
    • $185/SF
    • 2 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2005

    22540 Landing Way, Leonardtown, MD 20650

    Walk ability in Saint Marys Count how amazing! This home is right next to Leonardtown Wharf. Walk to the restaurants, festivals, and Santa sightings in Leonardtown. The beautiful home has 3 decks and 2 balconies. It has an elevator. Freshly professionally painted. New light fixtures. New Flooring. It has a newer roof.

    Trish Brow EXP Realty, LLC

    22540 Landing Way, Leonardtown, MD 20650
    • /82

      Est $575,555 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,475 Sq Ft

      22030 Cartwright Rd, Leonardtown, MD 20650

      22030 Cartwright Rd, Leonardtown, MD 20650
  • /64

    $625,000 Sold Dec 20, 2024

    • 1,144 Sq Ft
    • $546/SF
    • 21 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1961

    40481 Old Breton Beach Rd, Leonardtown, MD 20650

    Price included TWO Separate deeded LOTS! TWO PIERS!!! One New Sectic. This Dream Waterfront Home is being sold as a Turn-Key Home. Upgraded, Updated, new A/C and Ready for You. Did I mention TWO PIERS!!! The additional lot includes electric and septic, & utilities, as it previously had a home on it. The lot is being sold as is. Total acreage for both lots is 1.66. House = 1.32 acres and the lot

    Dawn Riley RE/MAX One

    40481 Old Breton Beach Rd, Leonardtown, MD 20650
    • /50

      Est $467,786 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,019 Sq Ft

      21807 Potomac View Dr, Leonardtown, MD 20650

      21807 Potomac View Dr, Leonardtown, MD 20650
  • /56

    $450,000 Sold Dec 20, 2024

    • 2,226 Sq Ft
    • $202/SF
    • 81 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1984

    40907 Cooper Dr, Leonardtown, MD 20650

    Nestled in one of the most sought-after neighborhoods, this charming residence offers an inviting blend of warmth, comfort and cozy. Boasting 3 bedrooms and 2.5 baths, this home is perfect for both families and those who love to entertain. New Roof just installed! The moment you step inside, you're greeted by beautiful hardwood floors that flow throughout the main living areas, enhancing the

    Barbara Blades CENTURY 21 New Millennium

    40907 Cooper Dr, Leonardtown, MD 20650
    • /30

      Est $319,904 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,344 Sq Ft

      39790 Lady Baltimore Ave, Leonardtown, MD 20650

      39790 Lady Baltimore Ave, Leonardtown, MD 20650
  • /25

    $279,000 Sold Dec 18, 2024

    • 1,056 Sq Ft
    • $264/SF
    • 5 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 2008

    41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650

    Experience the blend of comfort and convenience of the sought after "Foxwell Community" at this beautifully upgraded 2-bedroom, 1-bathroom condo located at 41800 Eastwick Lane #1303. With 1,056 square feet of living space, this one-owner home beams with pride of ownership. The interior features new hardwood flooring throughout and a full suite of new stainless steel appliances, complemented by an

    Kelly Niland Home Towne Real Estate

    41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650
    • /57

      Est $528,159 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,689 Sq Ft

      41898 Jenkins Ct, Leonardtown, MD 20650

      41898 Jenkins Ct, Leonardtown, MD 20650
  • /52

    $549,900 Sold Dec 17, 2024

    • 4,832 Sq Ft
    • $114/SF
    • 14 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2004

    23585 Abraham Dr, Leonardtown, MD 20650

    IMMACULATE! Beautiful 5-bedroom, 3.5-bath 4832 SQFT Colonial with a 2-car garage is ready to welcome you!As you arrive, the lovely landscaping and inviting front elevation immediately catch your eye. The architectural roof is just a few years old, and the fully fenced backyard sits on a generous 0.38-acre lot in Leonardtown.The charming front porch is perfect for enjoying quiet

    Mark Frisco CENTURY 21 New Millennium

    23585 Abraham Dr, Leonardtown, MD 20650
    • /21

      Est $494,149 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,092 Sq Ft

      22318 Armstrong Dr, Leonardtown, MD 20650

      22318 Armstrong Dr, Leonardtown, MD 20650

Showing Results 241 - 280, Page 7 of 18

How to Buy a Home How to Finance a Home How to Sell a Home