5,199

Chaptico, MD Homes

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  • /49

    $591,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,918 Sq Ft

    44195 Jessica Ln, Leonardtown, MD 20650

    Stunning Cape Cod on 3+ Acres in Leonardtown!Welcome to this beautifully maintained 4-bedroom, 2.5-bath Colonial offering 2,918 sq ft of spacious living, nestled on 3.13 acres in the heart of Leonardtown. From the moment you arrive, you’ll feel the charm—this home stands out with its impressive curb appeal and serene setting.The wide, well-manicured driveway leads to a side-load

    Mark Frisco CENTURY 21 New Millennium

    44195 Jessica Ln, Leonardtown, MD 20650
  • /30

    $410,000 Sold Mar 12, 2025

    • 1,634 Sq Ft
    • $251/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1998

    19680 Ellis Statesman Ln, Valley Lee, MD 20692

    Meticulously maintained rambler in Valley Lee, MD This rambler sits on 3 private acres of land with room for your imagination to make the lot your own. It has three large bedrooms, 2 full baths, an eat-in kitchen, large living room and stepdown family room that goes out to a deck. Roof is under a year old annd home is ready for occupancy . Owner is in the process of getting new appliances

    Heather Heath RE/MAX One

    19680 Ellis Statesman Ln, Valley Lee, MD 20692
    • /4

      Est $279,192 Not Listed For Sale

      19220 Eliff Ln, Valley Lee, MD 20692

      19220 Eliff Ln, Valley Lee, MD 20692
  • /9

    $580,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,628 Sq Ft

    17485 Lighthouse Commons Dr, Piney Point, MD 20674

    Ready June 2025, a brand-new custom construction home with four bedrooms and a two-car garage offers modern living at its finest. At 2628 square feet, there's plenty of room for the whole family to spread out comfortably. The gourmet kitchen is a highlight, perfect for cooking up delicious meals and entertaining guests. The deluxe master bath adds a touch of luxury, providing a spa-like retreat

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    17485 Lighthouse Commons Dr, Piney Point, MD 20674
  • /40

    $610,000 Sold Mar 07, 2025

    • 2,950 Sq Ft
    • $207/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2004

    19292 Vanderhoof Ln, Valley Lee, MD 20692

    If you're looking for privacy, and room to grow, you got it with this home! Sitting on just over 6 private, wooded acres, this spacious home boasts almost 3000 square feet of one level living space, along with with a huge unfinished basement to create even more living area with plenty of left over room for storage. With 4 bedrooms and 2.5 baths, there is room for everyone. The owner

    Janet Weaver RE/MAX One

    19292 Vanderhoof Ln, Valley Lee, MD 20692
    • /55

      Est $528,833 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,282 Sq Ft

      22010 Victorian Dr, California, MD 20619

      22010 Victorian Dr, California, MD 20619
  • /2

    $615,000 Open House 5/24

    • 5 Beds
    • 3.5 Baths
    • 3,635 Sq Ft

    44114 Woodmont Dr, Leonardtown, MD 20650

    NO SHOWINGS UNTILL THE OPEN HOUSE MAY 24, SAT 11-2. PHOTOS WILL BE IN THE WEEK BEFOREGorgeous 5-bedroom home with 3.5 baths on 2 acres . All five bedrooms are conveniently located on the upper level. The main floor features a versatile flex den/office, a formal dining room, a parlor, and an open-concept kitchen and family room. The stunning kitchen features a center island with an eat-at

    Lori Jean Buongiovanni (Hethmon) RE/MAX Realty Group

    44114 Woodmont Dr, Leonardtown, MD 20650
  • /23

    $385,000 Sold Feb 26, 2025

    • 1,838 Sq Ft
    • $209/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1984

    46030 Bates Rd, Great Mills, MD 20634

    Discover your dream home in the highly desirable Southern Maryland area! This spacious 3-bedroom, 2-bathroom rambler with an oversized garage boasts over 1,800 square feet of inviting living space, perfect for families or entertaining.Imagine cozy evenings gathered around the newly installed pellet-burning fireplace in the family room, or hosting friends in the airy kitchen and dining

    Thomas Pilkerton EXP Realty, LLC

    46030 Bates Rd, Great Mills, MD 20634
    • /76

      Est $547,259 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,342 Sq Ft

      19661 Hickory Hills Ln, Leonardtown, MD 20650

      19661 Hickory Hills Ln, Leonardtown, MD 20650
  • /75

    $599,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,646 Sq Ft

    46080 N Greens Rest Dr, Great Mills, MD 20634

    Spacious 4-Bedroom Home on 2 Acres – Close to PAX River with Water Access!Welcome to this well maintained 4-bedroom, 3.5-bath home situated on a level 2-acre lot, offering the perfect blend of space, privacy, and charm. The fully finished basement boasts an office and a versatile flex room that can easily serve as a home gym, 5th bedroom, or second home office—tailored to suit your needs.Enjoy

    Mary-Blake Summerlin CENTURY 21 New Millennium

    46080 N Greens Rest Dr, Great Mills, MD 20634
  • /24

    $343,500 Sold Feb 21, 2025

    • 1,650 Sq Ft
    • $208/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2013

    17849 4th St, Tall Timbers, MD 20690

    Well maintained home featuring an open floor plan with hardwood floors on the main level. The kitchen boasts cherry cabinets, while the outdoor spaces include a patio perfect for grilling and a covered front porch ideal for morning coffee. Additional highlights include an oversized garage, a concrete parking pad, and a nicely landscaped yard. The heat pump is approximately 2 years old.

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    17849 4th St, Tall Timbers, MD 20690
    • /27

      Est $250,078 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 700 Sq Ft

      45317 Leahy Dr, Piney Point, MD 20674

      45317 Leahy Dr, Piney Point, MD 20674
  • /65

    $599,999 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 3,139 Sq Ft

    42279 Bird Haven Dr, Leonardtown, MD 20650

    Beautiful home located in the desirable Leonardtown neighborhood of Kingston, this home features 5 bedrooms and 3.5 Baths . The main level features a large kitchen with granite counter tops and stainless steel appliances, spacious family room with wood burning fireplace, a home office with built-in storage, and formal dining room. The primary suite located on the second level features a large

    Mike Jordan CENTURY 21 New Millennium

    42279 Bird Haven Dr, Leonardtown, MD 20650
  • /45

    $485,000 Sold Feb 14, 2025

    • 3,275 Sq Ft
    • $148/SF
    • 7 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2002

    45842 Kingfisher Ct, Lexington Park, MD 20653

    Welcome to this meticulously maintained 4-bedroom, 3.5-bathroom colonial that perfectly blends modern comfort with timeless charm. Step inside the open foyer with high ceilings that set the tone for the bright and airy interior. The main level offers a dedicated office space, a convenient laundry room, and a spacious living area featuring an electric fireplace. The kitchen is complete with an

    Cayleigh Gibbons RE/MAX One

    45842 Kingfisher Ct, Lexington Park, MD 20653
    • /34

      Est $651,642 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,657 Sq Ft

      182 Salisbury Park Rd, Hague, VA 22469

      182 Salisbury Park Rd, Hague, VA 22469
  • /39

    $549,900 Under Contract

    • 5 Beds
    • 3 Baths
    • 2,888 Sq Ft

    18111 River Rd, Tall Timbers, MD 20690

    Charming Waterfront Cottage in sought after Tall Timbers on the Potomac with Original Cedar Shake Siding. A Premium Waterfront Lot with Rip Rap, Pier Pilings, and Sunset Views! Original Hardwood Floors throughout. Bright Kitchen and Dining Room with Water Views are perfect for Entertaining. Large Living Room with a Cozy Wood Burning Fireplace. Three (3) Lovely Little Bedrooms on the Main

    Jenny Norris EXP Realty, LLC

    18111 River Rd, Tall Timbers, MD 20690
  • /58

    $480,000 Sold Feb 14, 2025

    • 2,888 Sq Ft
    • $166/SF
    • 25 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    45672 Edge Mill Ct, Great Mills, MD 20634

    Beautiful home with covered front porch. Main level is open and spacious. Generous size family room. Kitchen has lots of counter space with a breakfast area. Panty, Laundry room, This home meets all your needs. The backyard has a raised bed for a garden. The backyard is fenced and private with a lovely large concrete patio . Need more, there is a sturdy coordinating shed. The lower

    Trish Brow EXP Realty, LLC

    45672 Edge Mill Ct, Great Mills, MD 20634
    • /53

      Est $350,762 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,380 Sq Ft

      21177 Lizmill Way, California, MD 20619

      21177 Lizmill Way, California, MD 20619
  • /56

    $395,000

    • 2 Beds
    • 2 Baths
    • 1,661 Sq Ft

    20161 Tower Hill Rd, Leonardtown, MD 20650

    This contemporary cape cod style home is it's own private retreat on over 3 acres. The main floor gives you a formal living room with vaulted celing and 2 sided woodstove/fireplace while also providing an additional family room that could easily be converted to a 3rd bedroom. The kitchen has been updated with granite counter tops, subway tiled backsplash, new appliances and more. Dining room

    Trish Wallmark RE/MAX One

    20161 Tower Hill Rd, Leonardtown, MD 20650
  • /51

    $400,000 Sold Feb 03, 2025

    • 2,464 Sq Ft
    • $162/SF
    • 11 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1974

    45798 Guenther Dr, Great Mills, MD 20634

    Charming Split-Foyer Home in Great Mills, MD – Ideal Location and Modern Upgrades! This beautifully updated 4-bedroom, 2-bathroom split-foyer home offers the perfect blend of comfort, style, and convenience. Located in the heart of St. Mary’s County, it provides a serene retreat on a private, half-acre wooded lot while maintaining easy access to nearby amenities. The property is ideally situated

    Adam Carpenter Keller Williams Flagship

    45798 Guenther Dr, Great Mills, MD 20634
    • /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft

      17555 Piney Point Rd, Piney Point, MD 20674

      17555 Piney Point Rd, Piney Point, MD 20674
  • /2

    $45,000

    • Land
    • 0.28 Acre
    • $160,714 per Acre

    0 Unknown Unit MDSM2023836, Tall Timbers, MD 20690

    12000Sqft lot to build a new home on. Close to water. In a Water access community

    Debbie Buckingham Samson Properties

    0 Unknown Unit MDSM2023836, Tall Timbers, MD 20690
  • /40

    $331,900 Sold Jan 31, 2025

    • 1,150 Sq Ft
    • $289/SF
    • 14 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1980

    45967 Boothe Farm Ln, Great Mills, MD 20634

    Newly renovated home on a sizable secluded lot ready for you to call home for the cozy season! Fresh paint, new carpet, luxury vinyl plank flooring, LED lighting throughout accentuates the rest of the updates in the house. The kitchen features new stainless steel appliances and gleaming granite countertops. The kitchen sinks sits under a double window perfectly placed to look out to the back

    Emily Watts Exit Landmark Realty

    45967 Boothe Farm Ln, Great Mills, MD 20634
    • /2

      Not Listed For Sale

      • Studio
      • 520 Sq Ft

      19920 Piney Point Rd, Piney Point, MD 20674

      19920 Piney Point Rd, Piney Point, MD 20674
  • /47

    $459,900

    • 3 Beds
    • 3 Baths
    • 1,892 Sq Ft

    20521 Old Gravel Ln, Lexington Park, MD 20653

    This beautifully cared-for home on 0.7 acres. This lot is just minutes from Patuxent River Naval Base—with no HOA and so much to love.Recent upgrades include a new roof, porch, and siding in 2023, giving this home fresh curb appeal and peace of mind. Upstairs, you’ll find a spacious primary suite with skylights overlooking the backyard —it is your own private space to relax and recharge.Step out

    Steph Rivers The Southside Group Real Estate

    20521 Old Gravel Ln, Lexington Park, MD 20653
  • /76

    $689,000 Sold Jan 31, 2025

    • 3,462 Sq Ft
    • $199/SF
    • 3 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2006

    46461 Porto Bello Ct, Drayden, MD 20630

    Welcome to this beautifully remodeled 5-bedroom, 3 full bathroom home that seamlessly blends modern upgrades with classic charm. Located in the desirable neighborhood of Porto Bello Estates, this spacious home boasts all-new landscaping that enhances the curb appeal and invites you in. Step inside to find fresh paint throughout, new carpets, and refinished hardwood floors that add warmth and

    Jessica Abad CENTURY 21 New Millennium

    46461 Porto Bello Ct, Drayden, MD 20630
    • /17

      Est $370,225 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,180 Sq Ft

      45747 Bethfield Way, California, MD 20619

      45747 Bethfield Way, California, MD 20619
  • /24

    $260,000 Open Sat 12PM - 3PM

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    17253 Larimer St, Piney Point, MD 20674

    Check out our upcoming OPEN HOUSE and ACTIVE listing 5-3-2025 from 12-3 PM. Get ready to visit soon as the seller completes a few final touches to this lovely home. A quiet neighborhood, but situated next to St Georges Island with public boat launch, sandy recreation galore for the whole family and all your friends. Experience the local and fun businesses for dining, pizza, fishing and so much

    Juan Aranda CENTURY 21 New Millennium

    17253 Larimer St, Piney Point, MD 20674
  • /111

    $1,475,000 Sold Jan 28, 2025

    • 6,470 Sq Ft
    • $228/SF
    • 37 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2005

    19540 Pristine Way, Drayden, MD 20630

    Nestled within the serene St. Mary's River waterside community of Christmas Hill in Drayden, this exquisite 6,300 sq ft Italian villa-inspired residence at 19540 Pristine's Way offers a harmonious blend of luxury and comfort just in time for the Holidays! The spacious formal Dining room & Living room is ready for your family gatherings! Cook up the feast in the gourmet kitchen with new granite

    Kelly Niland Home Towne Real Estate

    19540 Pristine Way, Drayden, MD 20630
    • /43

      Est $427,751 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,010 Sq Ft

      20846 Autumn Mill Ct, Great Mills, MD 20634

      20846 Autumn Mill Ct, Great Mills, MD 20634
  • /7

    $50,000

    • Land
    • 0.87 Acre
    • $57,471 per Acre

    11800 Point Lookout Rd, Scotland, MD 20687

    Check out this lot in Scotland just around the corner from the Point Lookout State Park. Use it to build a house, garage, or park your camper or boat. Views of one of Scotland's beloved farms in the back and woods in the front. Existing structure is not livable

    Trish Wallmark RE/MAX One

    11800 Point Lookout Rd, Scotland, MD 20687
  • /29

    $251,000 Sold Jan 17, 2025

    • 1,188 Sq Ft
    • $211/SF
    • 23 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1990

    44840 Wood Duck Ln, Callaway, MD 20620

    *New Roof is on the schedule!!*Welcome to this beautifully updated three-bedroom, one and a half bath townhouse! Step inside to find brand-new flooring throughout and freshly painted walls that make this home feel bright and inviting. The main floor offers a spacious layout, perfect for both relaxation and entertaining, and opens to a lovely rear deck overlooking a fenced backyard—ideal for

    Jessica Raley CENTURY 21 New Millennium

    44840 Wood Duck Ln, Callaway, MD 20620
    • /11

      Est $293,233 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,392 Sq Ft

      17854 Saint Georges Park Rd, Tall Timbers, MD 20690

      17854 Saint Georges Park Rd, Tall Timbers, MD 20690
  • /97

    $465,000

    • 3 Beds
    • 3 Baths
    • 3,605 Sq Ft

    21500 Point Lookout Rd, Callaway, MD 20620

    All-Brick Rambler on a 6.11, This does not include the additional parcel of 9.58 acres. This all-brick rambler sits on a large extensively landscaped lot and offers over 3,600 + sq. ft. on the main level, plus 1,200+ sq. ft. in the partially finished lower level. The home features 3 bedrooms (including 2 primary suites, one with fireplace), 2 full baths on main level, 4 wood burning

    Jennifer Goddard CENTURY 21 New Millennium

    21500 Point Lookout Rd, Callaway, MD 20620
  • /45

    $420,000 Sold Jan 10, 2025

    • 2,164 Sq Ft
    • $194/SF
    • 4 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1983

    21819 Magnolia Dr, California, MD 20619

    Charming 5-Bedroom Home with Spacious Lot and Detached Workshop!21819 Magnolia Dr, California, MD 20619Nestled on 1.51 acres of serene land, this beautiful 5-bedroom, 3-bathroom home offers the perfect blend of space, comfort, and versatility. With over 2,000 square feet of living space, this well-maintained property is ideal for growing families, hobbyists, or those seeking room to

    Conor Loughran CENTURY 21 New Millennium

    21819 Magnolia Dr, California, MD 20619
    • /56

      Est $659,397 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,296 Sq Ft

      21147 Catnip Ct, Leonardtown, MD 20650

      21147 Catnip Ct, Leonardtown, MD 20650
  • /37

    $469,900 Open Sun 1PM - 3PM

    • 4 Beds
    • 3 Baths
    • 2,154 Sq Ft

    44889 Mallard Place, Callaway, MD 20620

    Welcome to this stunning home in Callaway, Maryland, located in a cul-de-sac. This spacious 4-bedroom home offers an open floor plan filled with natural light and tons of character. The lower level features large bay windows that flood the living area with sunshine, creating a bright and inviting space for gatherings or quiet relaxation.The luxurious primary suite includes a beautiful primary

    Jesieryl Hartzer CENTURY 21 New Millennium

    44889 Mallard Place, Callaway, MD 20620
  • /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
    • /20

      Est $241,767 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,188 Sq Ft

      44834 Wood Duck Ln, Callaway, MD 20620

      44834 Wood Duck Ln, Callaway, MD 20620
  • /4

    $125,000

    • Land
    • 1.72 Acres
    • $72,674 per Acre

    19400 Brandon Way, Great Mills, MD 20634

    Last lot available in this very desirable neighborhood. Perc was performed last year in 2023 and passed. Build your dream home. 1.72 acres of land waiting for you. Nice location close to everything yet private. Got questions please ask.

    Melanie Montague EXP Realty, LLC

    19400 Brandon Way, Great Mills, MD 20634

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