5,236

Chaptico, MD Homes

Section Image
  • /43

    $359,900 Sold Feb 06, 2026

    20751 Wolftrap St, Lexington Park, MD 20653

    • 3 Beds
    • 3 Baths
    • 2,195 Sq Ft
    • Built 1996

    Last Sold Summary

    • $164/SF
    • 69 Days On Market

    Current Estimated Value $357,503

    Last Listing Agent Patrick Deighan CENTURY 21 New Millennium

    20751 Wolftrap St, Lexington Park, MD 20653
    • /80

      Est $591,205 Not Listed For Sale

      45475 Mount Olive Way, Valley Lee, MD 20692

      • 4 Beds
      • 3.5 Baths
      • 2,980 Sq Ft
      • Built 1994
      45475 Mount Olive Way, Valley Lee, MD 20692

      Last Sold Summary

      • 1% Below List Price
      • $201/SF
      • 28 Days On Market

      Last Sold Price $600,000

      Last Listing Agent Kelly Padgett Century 21 New Millennium

  • /40

    $444,900 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,964 Sq Ft

    45903 Burns Dr, Valley Lee, MD 20692

    Welcome home! Nestled on a this 2+ private lot framed by mature trees, this spacious rambler offers the perfect blend of comfort and style. Generous family room with a stunning bay window that flows into the dining area and a bright, well-lit kitchen featuring maple cabinets with cherry finish, Corian counters, and a center island. Designed with a thoughtful split-bedroom floor plan, the generous

    Tracey Summers CENTURY 21 New Millennium

    45903 Burns Dr, Valley Lee, MD 20692
  • /44

    $530,000 Sold May 19, 2025

    20785 Brook Mill Ct, Great Mills, MD 20634

    • 5 Beds
    • 3 Baths
    • 2,924 Sq Ft
    • Built 2006

    Last Sold Summary

    • $181/SF
    • 2 Days On Market

    Current Estimated Value $538,502

    Last Listing Agent Stewart Tellechea RE/MAX Realty Group

    20785 Brook Mill Ct, Great Mills, MD 20634
    • /78

      Est $464,629 Not Listed For Sale

      45860 Ketch Ct, Lexington Park, MD 20653

      • 4 Beds
      • 3.5 Baths
      • 3,532 Sq Ft
      • Built 2005
      45860 Ketch Ct, Lexington Park, MD 20653

      Last Sold Summary

      • 1% Below List Price
      • $133/SF
      • 11 Days On Market

      Last Sold Price $469,900

      Last Listing Agent Kelly Padgett Century 21 New Millennium

  • /13

    $170,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,026 Sq Ft

    20959 Redgate Ln, Leonardtown, MD 20650

    *Back on the market. A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland offers promising opportunities for both homebuyers and investors, driven by its growing real estate market and strategic economic initiatives over the years. This property may be best suited for an investor or seasoned buyer who has the vision and capacity to restore it with some

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
  • /95

    $835,000 Sold Mar 10, 2026

    45146 Andover Estates Rd, Valley Lee, MD 20692

    • Studio
    • 4,366 Sq Ft
    • Built 1971

    Last Sold Summary

    • $191/SF
    • 79 Days On Market

    Current Estimated Value $832,482

    Last Listing Agent Jan Barnes CENTURY 21 New Millennium

    45146 Andover Estates Rd, Valley Lee, MD 20692
    • /73

      Est $497,833 Not Listed For Sale

      19845 Fall Ct, Great Mills, MD 20634

      • 4 Beds
      • 3.5 Baths
      • 3,434 Sq Ft
      • Built 1998
      19845 Fall Ct, Great Mills, MD 20634

      Last Sold Summary

      • 16% Above List Price
      • $125/SF
      • 77 Days On Market

      Last Sold Price $428,000

      Last Listing Agent James Sapia Century 21 Downtown

  • /8

    $269,700

    • Land
    • 1.63 Acres
    • $165,460 per Acre

    46175 N Greens Rest Dr, Great Mills, MD 20634

    One of the few remaining pristine lots left in Riverside Farms! 1.63 acre lot with permits, approved site plan, grading, and foundation in for 4BR, 3-4 BA 3500+ sq. ft. custom rambler with basement. Handicap accessible! This desirable neighborhood offers a community park, ball fields, walking trails, picnic areas, and community pier.Conveniently, located close to Leonardtown and Pax River

    Joe and Judi Limerick CENTURY 21 New Millennium

    46175 N Greens Rest Dr, Great Mills, MD 20634
  • /27

    $515,000 Sold Aug 15, 2025

    20755 Deer Wood Park Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,538 Sq Ft
    • Built 1996

    Last Sold Summary

    • $203/SF
    • 10 Days On Market

    Current Estimated Value $548,438

    Last Listing Agent Ebon Jackson EbonAries Realty Group, LLC.

    20755 Deer Wood Park Dr, Leonardtown, MD 20650
    • /81

      Est $471,062 Not Listed For Sale

      45844 Ketch Ct, Lexington Park, MD 20653

      • 6 Beds
      • 3.5 Baths
      • 4,530 Sq Ft
      • Built 2006
      45844 Ketch Ct, Lexington Park, MD 20653

      Last Sold Summary

      • 4% Above List Price
      • $100/SF
      • 19 Days On Market

      Last Sold Price $455,000

      Last Listing Agent Jessica Raley Century 21 New Millennium

  • /50

    $1,495,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,713 Sq Ft

    46502 Glen Mary Farm Rd, Park Hall, MD 20667

    Your Own Private Island; A 90-Minute Drive from Washington DC Even if our own experience was different, most of us can envision care-free summer days at the shore. Games on the beach, hiking in the forest; only coming back to the house at sunset when it was obvious that we were late for dinner. Now you and your family can create your own summer wonderland with the purchase of an idyllic island

    David DeSantis TTR Sotheby's International Realty

    46502 Glen Mary Farm Rd, Park Hall, MD 20667
  • /48

    $475,000 Sold Feb 16, 2026

    44892 Golden Eye Ct, Callaway, MD 20620

    • 4 Beds
    • 2.5 Baths
    • 2,536 Sq Ft
    • Built 2002

    Last Sold Summary

    • $187/SF
    • 103 Days On Market

    Current Estimated Value $483,069

    Last Listing Agent Dawn Riley RE/MAX One

    44892 Golden Eye Ct, Callaway, MD 20620
    • /16

      Est $1,019,012 Not Listed For Sale

      44477 Tall Timbers Rd, Tall Timbers, MD 20690

      • 8 Beds
      • 4.5 Baths
      • 5,513 Sq Ft
      • Built 1927
      44477 Tall Timbers Rd, Tall Timbers, MD 20690

      Last Sold Summary

      • 19% Above List Price
      • $155/SF
      • 20 Days On Market

      Last Sold Price $854,000

      Last Listing Agent Christopher Guldi Keller Williams Flagship

  • /45

    $335,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    23311 Point Lookout Rd, Leonardtown, MD 20650

    Charming Leonardtown Rambler on a Full Acre. Move-In Ready! Welcome home to the house you've been waiting for. Whether you're buying your first home or rightsizing into something smarter, this meticulously maintained 2-bedroom, 2-bath rambler delivers the Leonardtown lifestyle without the big-house headaches. Freshly painted throughout, walls and ceilings, the home features luxury vinyl plank

    JW Abney RE/MAX One

    23311 Point Lookout Rd, Leonardtown, MD 20650
  • /41

    $541,000 Sold Jul 25, 2025

    20955 Aster Dr, Callaway, MD 20620

    • 4 Beds
    • 2.5 Baths
    • 2,356 Sq Ft
    • Built 1996

    Last Sold Summary

    • $230/SF
    • 17 Days On Market

    Current Estimated Value $553,079

    Last Listing Agent Carol Kalmus-Choporis CENTURY 21 New Millennium

    20955 Aster Dr, Callaway, MD 20620
    • /68

      Est $669,415 Not Listed For Sale

      42990 Baywood Place, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,724 Sq Ft
      • Built 2009
      42990 Baywood Place, Leonardtown, MD 20650

      Last Sold Summary

      • 1% Above List Price
      • $242/SF
      • 2 Days On Market

      Last Sold Price $660,000

      Last Listing Agent Farrah Fuchs Redfin Corp

  • /2

    $99,000

    • Land
    • 0.52 Acre
    • $190,385 per Acre

    17377 Piney Point Rd, Piney Point, MD 20674

    Discover the opportunity to create your ideal home on this 22,782 square foot parcel (just over half an acre) located on Piney Point in scenic St. Mary's County. Identified as Adjusted Parcel 174, this property offers a peaceful setting with convenient access to the waterfront lifestyle that makes Piney Point such a desirable destination. With no existing improvements, the lot provides a blank

    Matthew Burgan Infinitas Realty Group

    17377 Piney Point Rd, Piney Point, MD 20674
  • /91

    $589,000 Sold Jul 18, 2025

    21946 Short Bow Ct, California, MD 20619

    • 4 Beds
    • 3 Baths
    • 3,502 Sq Ft
    • Built 2003

    Last Sold Summary

    • $168/SF
    • 13 Days On Market

    Current Estimated Value $597,099

    Last Listing Agent John Gatton CENTURY 21 New Millennium

    21946 Short Bow Ct, California, MD 20619
    • /20

      Est $523,564 Not Listed For Sale

      45192 Loblolly Ct, Tall Timbers, MD 20690

      • 4 Beds
      • 2.5 Baths
      • 2,950 Sq Ft
      • Built 2003
      45192 Loblolly Ct, Tall Timbers, MD 20690

      Last Sold Summary

      • 64% Above List Price
      • $108/SF
      • 8 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Jennifer Goddard Century 21 New Millennium

  • /44

    $324,900 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,330 Sq Ft

    17262 Larimer St, Piney Point, MD 20674

    Welcome home to your beautiful move in ready home with WATER ACCESS! This home features 3 bedrooms and 2 full bathrooms. As you enter, you will love the open concept feel of the kitchen, dining, and living room. The kitchen features concrete countertops and a new stove (2025). The living room features a built in electric fireplace. The large primary bedroom features a walk in closet and a

    Kristen Willets RE/MAX One

    17262 Larimer St, Piney Point, MD 20674
  • /23

    $295,000 Sold May 14, 2025

    20235 Big Oak Ln, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,036 Sq Ft
    • Built 1934

    Last Sold Summary

    • $285/SF
    • 4 Days On Market

    Current Estimated Value $296,983

    Last Listing Agent Jan Kleponis O'Brien Realty ERA Powered

    20235 Big Oak Ln, Leonardtown, MD 20650
    • /58

      Est $484,735 Not Listed For Sale

      45672 Edge Mill Ct, Great Mills, MD 20634

      • 4 Beds
      • 2.5 Baths
      • 2,888 Sq Ft
      • Built 2005
      45672 Edge Mill Ct, Great Mills, MD 20634

      Last Sold Summary

      • 1% Above List Price
      • $166/SF
      • 25 Days On Market

      Last Sold Price $480,000

      Last Listing Agent Trish Brow EXP Realty, LLC

  • /52

    $505,000 Pending

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

    21027 Hunting Quarter Dr, Callaway, MD 20620

    Situated on a spacious corner lot in Callaway, this pristine two-level home offers both immediate readiness and long-term flexibility. Recently painted in multiple interior spaces and professionally cleaned throughout, the property has been thoughtfully prepared for its next chapter. It presents beautifully and is ready for immediate occupancy.The home features four bedrooms and two and a

    Diana Washabaugh CENTURY 21 New Millennium

    21027 Hunting Quarter Dr, Callaway, MD 20620
  • /2

    $75,000 Sold Mar 13, 2026

    22020 Victorian Dr, California, MD 20619

    • Land
    • 1.68 Acres
    • $44,643 per Acre

    Last Sold Summary

    • 25% Below List Price
    • 968 Days On Market

    Current Estimated Value $87,500

    Last Listing Agent Dawn Wood O'Brien Realty ERA Powered

    22020 Victorian Dr, California, MD 20619
    • /30

      Est $489,609 Not Listed For Sale

      20861 Harvest Mill Ct, Great Mills, MD 20634

      • 4 Beds
      • 3.5 Baths
      • 3,130 Sq Ft
      • Built 2008
      20861 Harvest Mill Ct, Great Mills, MD 20634

      Last Sold Summary

      • 7% Above List Price
      • $147/SF
      • 5 Days On Market

      Last Sold Price $459,000

      Last Listing Agent Sonia Roy Century 21 New Millennium

  • /2

    $60,000

    • Land
    • 0.28 Acre
    • $214,286 per Acre

    0 Holly St, Piney Point, MD 20674

    Build a new home on this 12000 Sg ft lot located in Piney Point. Maryland. Public sewer available for hookup.

    Mike Jordan CENTURY 21 New Millennium

    0 Holly St, Piney Point, MD 20674
  • /2

    $345,000 Sold Feb 03, 2026

    20314 Brent Ln, Callaway, MD 20620

    • 3 Beds
    • 2 Baths
    • 1,580 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Above List Price
    • $218/SF
    • 9 Days On Market

    Current Estimated Value $339,441

    Last Listing Agent Steven Carroll Berkshire Hathaway HomeServices PenFed Realty

    20314 Brent Ln, Callaway, MD 20620
    • /41

      Est $565,089 Not Listed For Sale

      19370 Greens Crossing Ct, Great Mills, MD 20634

      • 5 Beds
      • 3.5 Baths
      • 3,044 Sq Ft
      • Built 2008
      19370 Greens Crossing Ct, Great Mills, MD 20634

      Last Sold Summary

      • 4% Above List Price
      • $179/SF
      • 23 Days On Market

      Last Sold Price $545,000

      Last Listing Agent Mitchell Seifert RE/MAX

  • /2

    $365,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,644 Sq Ft

    44731 Blake Creek Rd, Leonardtown, MD 20650

    Welcome to 44731 Blake Creek Road in the sought-after Leonardtown. This beautifully updated single-story rambler sits on over an acre of private land, offering the best of Southern Maryland country living with easy access to everything you need. Step inside to find a home that has been thoughtfully refreshed and updated for today's buyer. With 1,644 square feet of single-level living, this

    Sarah Mulford-Martin EXP Realty, LLC

    44731 Blake Creek Rd, Leonardtown, MD 20650
  • /69

    $622,500 Sold Jul 21, 2025

    21143 Catnip Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,642 Sq Ft
    • Built 2003

    Last Sold Summary

    • $236/SF
    • 16 Days On Market

    Current Estimated Value $625,355

    Last Listing Agent Melissa Rodriguez RE/MAX One

    21143 Catnip Ct, Leonardtown, MD 20650
    • /31

      Est $588,500 Not Listed For Sale

      21084 Rosebay St, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,505 Sq Ft
      • Built 2003
      21084 Rosebay St, Leonardtown, MD 20650

      Last Sold Summary

      • 15% Above List Price
      • $146/SF
      • 30 Days On Market

      Last Sold Price $510,000

      Last Listing Agent Josh Yowell EXP Realty, LLC

  • /59

    $549,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,945 Sq Ft

    17615 Driftwood Dr, Tall Timbers, MD 20690

    If you've been waiting for a great house to hit the market, here's your chance. Located in The Landings at Piney Point, this sought-after location offers a desirable waterfront location and unparalleled community amenities. Enjoy the private, deep water marina with your own deeded boat slip (#58) that has a 10,000 lbs boat lift and direct access to the Potomac River. Soak up the sun at the

    Matthew Burgan Infinitas Realty Group

    17615 Driftwood Dr, Tall Timbers, MD 20690
  • /87

    $475,203 Sold Mar 02, 2026

    20697 Chingville Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,458 Sq Ft
    • Built 1948

    Last Sold Summary

    • $193/SF
    • 1 Day On Market

    Current Estimated Value $476,096

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    20697 Chingville Rd, Leonardtown, MD 20650
    • /47

      Est $279,866 Not Listed For Sale

      17254 Larimer St, Piney Point, MD 20674

      • 2 Beds
      • 1.5 Baths
      • 1,024 Sq Ft
      • Built 1944
      17254 Larimer St, Piney Point, MD 20674

      Last Sold Summary

      • 5% Below List Price
      • $288/SF
      • 4 Days On Market

      Last Sold Price $295,000

      Last Listing Agent Jessica Abad Century 21 New Millennium

  • /5

    $150,000

    • Land
    • 1.75 Acres
    • $85,714 per Acre

    45252 Happyland Rd, Valley Lee, MD 20692

    1.75 cleared acres zoned commercial. The address of 45252 Happyland Rd was assigned afterCommercial Outparcel C had an approved Perc. St. Mary’s County zoning is Rural Commercial Limited(RCL). Find information on uses of an RCL lot online at St. Mary's County comprehensive zoning ordinance. Excerpt from ordinance (RCL Jul 24, 2007... By the enactment of County Commissioners Ordinance No.

    Lawrence Lessin Save 6, Incorporated

    45252 Happyland Rd, Valley Lee, MD 20692
  • /51

    $410,000 Sold May 01, 2025

    17364 Potomac Sands Dr, Piney Point, MD 20674

    • 4 Beds
    • 3 Baths
    • 1,848 Sq Ft
    • Built 1998

    Last Sold Summary

    • $222/SF
    • 56 Days On Market

    Current Estimated Value $413,314

    Last Listing Agent Kim Gosnell Redfin Corp

    17364 Potomac Sands Dr, Piney Point, MD 20674
    • /36

      Est $356,838 Not Listed For Sale

      20725 Wolftrap St, Lexington Park, MD 20653

      • 3 Beds
      • 2.5 Baths
      • 1,776 Sq Ft
      • Built 1993
      20725 Wolftrap St, Lexington Park, MD 20653

      Last Sold Summary

      • 2% Above List Price
      • $197/SF
      • 36 Days On Market

      Last Sold Price $349,900

      Last Listing Agent Sandy Ludka Capps O'Brien Realty

  • /2

    $85,000

    • Land
    • 1.5 Acres
    • $56,667 per Acre

    0 Piney Point Rd, Callaway, MD 20620

    Discover the perfect canvas for your dream home on this 1.5-acre parcel of land, nestled in a vibrant community that offers both tranquility and convenience. Imagine waking up each day surrounded by nature, with ample space to create your own private oasis while still being just moments away from local amenities. This prime piece of land is situated in an area known for its friendly atmosphere

    Jessica Raley CENTURY 21 New Millennium

    0 Piney Point Rd, Callaway, MD 20620
  • /33

    $575,000 Sold Jan 09, 2026

    44968 Hewitt Rd, Callaway, MD 20620

    • 3 Beds
    • 2 Baths
    • 792 Sq Ft
    • Built 1975

    Last Sold Summary

    • $726/SF
    • 5 Days On Market

    Last Listing Agent Florentina Killian CENTURY 21 New Millennium

    44968 Hewitt Rd, Callaway, MD 20620

Showing Results 81 - 120, Page 3 of 18

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