5,236

Chaptico, MD Homes

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  • /16

    $776,220 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,253 Sq Ft

    19166 N Porto Bello Dr, Drayden, MD 20630

    The PARKER Model, Elevation One ** Please excuse our mess while construction is underway ** Wonderful Front Porch ** One Acre Plus WOODED Level Lot **FABULOUS KITCHEN w/Super Island & Granite Counters *** Huge PANTRY *** Upgraded STAINLESS Appliances *** First Floor Primary Bedroom complete with Custom Box Ceiling *** Master Bath with CUSTOM Walk in SHOWER w/Custom Seat ** Two Additional Main

    Lisa Riggleman RE/MAX One

    19166 N Porto Bello Dr, Drayden, MD 20630
  • /49

    $469,900 Sold Mar 27, 2026

    44913 Widgeon Place, Callaway, MD 20620

    • 4 Beds
    • 2.5 Baths
    • 2,430 Sq Ft
    • Built 2000

    Last Sold Summary

    • $193/SF
    • 67 Days On Market

    Current Estimated Value $471,979

    Last Listing Agent Jaye Hercules RE/MAX Realty Group

    44913 Widgeon Place, Callaway, MD 20620
    • /55

      Est $548,860 Not Listed For Sale

      22010 Victorian Dr, California, MD 20619

      • 3 Beds
      • 2.5 Baths
      • 2,282 Sq Ft
      • Built 2022
      22010 Victorian Dr, California, MD 20619

      Last Sold Summary

      • 16% Above List Price
      • $208/SF
      • 189 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Dawn Wood O'Brien Realty

  • /101

    $625,000

    • 5 Beds
    • 3.5 Baths
    • 5,270 Sq Ft

    45656 Edge Mill Ct, Great Mills, MD 20634

    If space, comfort, and entertaining are on your wish list, this 5-bedroom Colonial with over 5,600 finished square feet and a fully finished basement checks every box.Welcome to 45656 Edge Mill Court, an elegant Colonial tucked away on a quiet cul-de-sac in the sought-after Woodland Park community of Great Mills, Maryland. Offering more than 5,600 square feet of beautifully finished living

    Randell Dofat EXP Realty, LLC

    45656 Edge Mill Ct, Great Mills, MD 20634
  • /118

    $610,000 Sold Nov 28, 2025

    44906 Golden Eye Ct, Callaway, MD 20620

    • 6 Beds
    • 5 Baths
    • 6,006 Sq Ft
    • Built 2006

    Last Sold Summary

    • $102/SF
    • 57 Days On Market

    Current Estimated Value $618,533

    Last Listing Agent Kelly Padgett CENTURY 21 New Millennium

    44906 Golden Eye Ct, Callaway, MD 20620
    • /12

      Est $547,715 Not Listed For Sale

      22030 Victorian Dr, California, MD 20619

      • 4 Beds
      • 2.5 Baths
      • Built 2024
      22030 Victorian Dr, California, MD 20619

      Last Sold Summary

      • 2% Above List Price
      • 26 Days On Market

      Last Sold Price $536,000

      Last Listing Agent Florentina Killian Century 21 New Millennium

  • /2

    $750,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 2,936 Sq Ft

    20752 Penansey Ln, Leonardtown, MD 20650

    Multigenerationl suite is attached with a full kitchen, laundry room, living room, bedroom and full bathroom.

    Heather Foster RE/MAX One

    20752 Penansey Ln, Leonardtown, MD 20650
  • /43

    $420,000 Sold Nov 21, 2025

    20966 Black Duck Ct, Callaway, MD 20620

    • 3 Beds
    • 3.5 Baths
    • 2,264 Sq Ft
    • Built 1998

    Last Sold Summary

    • $186/SF
    • 88 Days On Market

    Current Estimated Value $426,764

    Last Listing Agent Farrah Fuchs Redfin Corp

    20966 Black Duck Ct, Callaway, MD 20620
    • /76

      Est $547,333 Not Listed For Sale

      19661 Hickory Hills Ln, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 2,342 Sq Ft
      • Built 1987
      19661 Hickory Hills Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 4% Above List Price
      • $224/SF
      • 8 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Katy Galloway Century 21 New Millennium

  • /68

    $590,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 3,526 Sq Ft

    21117 Catnip Ct, Leonardtown, MD 20650

    Seller is offering a $4,000 concession with an accepted full-price offer!Use it for an interest-rate buy-down, closing costs, or to add your own personal touches. Get ready to fall in love with this wonderful 5BR/3.5BA home in the Leonardtown's Kingston Estates! Set on a peaceful, no-through street and perched on a gentle hill, this home offers great privacy with mature trees, plenty of open

    Melissa Rodriguez RE/MAX One

    21117 Catnip Ct, Leonardtown, MD 20650
  • /12

    $135,000 Sold May 09, 2025

    42500 Saint Margarets Dr, Leonardtown, MD 20650

    • Land
    • 4.8 Acres
    • $28,125 per Acre

    Last Sold Summary

    • 76 Days On Market

    Current Estimated Value $133,863

    Last Listing Agent Kalee Kelly Infinitas Realty Group

    42500 Saint Margarets Dr, Leonardtown, MD 20650
    • /27

      Est $253,554 Not Listed For Sale

      45317 Leahy Dr, Piney Point, MD 20674

      • 2 Beds
      • 1 Bath
      • 700 Sq Ft
      • Built 1942
      45317 Leahy Dr, Piney Point, MD 20674

      Last Sold Summary

      • 4% Above List Price
      • $349/SF
      • 22 Days On Market

      Last Sold Price $244,100

      Last Listing Agent Charlotte Long EXP Realty, LLC

  • /31

    $599,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,343 Sq Ft

    19163 N Porto Bello Ln, Drayden, MD 20630

    *** To Be Built *** ONE ACRE Plus Wooded Level LOT *** THE ARUNDEL Model, Elevation II*** 2 CAR GARAGE ****FABULOUS KITCHEN w/Super Island & GRANITE Counters *** Pantry *** STAINLESS appliances *** Open Concept ** 1st Floor FAMILY ROOM open to the Kitchen *** full BASEMENT w/Rough in for a FULL BATH ** Optional REC ROOM and DEN *** INTERNET Available *** Street LIGHTS ** WARRANTY *** Pick this

    Lisa Riggleman RE/MAX One

    19163 N Porto Bello Ln, Drayden, MD 20630
  • /56

    $476,000 Sold Oct 15, 2025

    20898 Governors Mill Ct, Great Mills, MD 20634

    • 4 Beds
    • 3.5 Baths
    • 3,052 Sq Ft
    • Built 2011

    Last Sold Summary

    • $156/SF
    • 11 Days On Market

    Current Estimated Value $484,435

    Last Listing Agent Karen Simmons RE/MAX Realty Group

    20898 Governors Mill Ct, Great Mills, MD 20634
    • /24

      Est $373,246 Not Listed For Sale

      17849 4th St, Tall Timbers, MD 20690

      • 3 Beds
      • 2.5 Baths
      • 1,650 Sq Ft
      • Built 2013
      17849 4th St, Tall Timbers, MD 20690

      Last Sold Summary

      • 9% Above List Price
      • $208/SF
      • 0 Days On Market

      Last Sold Price $343,500

      Last Listing Agent Carol Kalmus-Choporis Century 21 New Millennium

  • /51

    $639,900

    • 4 Beds
    • 3 Baths
    • 2,486 Sq Ft

    46210 Lisa Marie Ct, Drayden, MD 20630

    Located in the desirable Porto Bello Estates community and thoughtfully designed with space, function, and style in mind. Built in 2021, this home offers 2,486 sqft above grade plus 1,087 sqft below, featuring an open concept layout with LVP flooring, a bright kitchen with granite countertops, center island, stainless appliances, and farmhouse sink. The main living areas flow seamlessly for

    Lisa Riggleman RE/MAX One

    46210 Lisa Marie Ct, Drayden, MD 20630
  • /71

    $599,900 Sold Jun 25, 2025

    42261 Bird Haven Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,233 Sq Ft
    • Built 2002

    Last Sold Summary

    • $186/SF
    • 18 Days On Market

    Current Estimated Value $604,254

    Last Listing Agent Melissa Rodriguez RE/MAX One

    42261 Bird Haven Dr, Leonardtown, MD 20650
    • /53

      Est $360,425 Not Listed For Sale

      21177 Lizmill Way, California, MD 20619

      • 3 Beds
      • 2.5 Baths
      • 2,380 Sq Ft
      • Built 2014
      21177 Lizmill Way, California, MD 20619

      Last Sold Summary

      • 11% Above List Price
      • $137/SF
      • 3 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Barbara Blades Century 21 New Millennium

  • /32

    $599,900

    • 4 Beds
    • 2.5 Baths
    • 3,428 Sq Ft

    43552 Bayberry Ct, Leonardtown, MD 20650

    Nestled on 2.2 private acres in Chestnut Ridge, this beautiful 4-bedroom home offers space, comfort, and functionality for modern living. The home features generously sized bedrooms and a thoughtfully designed layout perfect for both everyday life and entertaining. The main level includes a spacious kitchen and family room combination—ideal for gatherings—complete with a cozy brick gas fireplace

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    43552 Bayberry Ct, Leonardtown, MD 20650
  • /16

    $281,650 Sold Sep 30, 2025

    43658 Redmond Rd, Leonardtown, MD 20650

    • 4 Beds
    • 1.5 Baths
    • 2,078 Sq Ft
    • Built 1959

    Last Sold Summary

    • $136/SF
    • 12 Days On Market

    Current Estimated Value $320,437

    Last Listing Agent Candide Rayle CENTURY 21 New Millennium

    43658 Redmond Rd, Leonardtown, MD 20650
    • /21

      Not Listed For Sale

      19920 Piney Point Rd, Piney Point, MD 20674

      • Built 1960
      19920 Piney Point Rd, Piney Point, MD 20674

      Last Sold Summary

      • $163/SF
      • 1,902 Days On Market

      Last Sold Price $85,000

      Last Listing Agent Ellie Stommel Hyatt & Company Real Estate LLC

  • /69

    $674,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,243 Sq Ft

    44545 Brewer Ln, Leonardtown, MD 20650

    This beautiful custom rambler sits on over 2.5 peaceful acres, offering plenty of privacy and space. A welcoming circular driveway and a covered front porch greet you as you arrive, setting a relaxed tone right from the start.Inside, you’ll find thoughtful details throughout: 6-inch custom trim, wide 36-inch doorways, lots of natural light, and 9-foot ceilings that give the home an open,

    Tracey Summers CENTURY 21 New Millennium

    44545 Brewer Ln, Leonardtown, MD 20650
  • /45

    $380,000 Sold May 27, 2025

    18631 Cherryfield Rd, Drayden, MD 20630

    • 3 Beds
    • 2 Baths
    • 1,864 Sq Ft
    • Built 1978

    Last Sold Summary

    • $204/SF
    • 5 Days On Market

    Current Estimated Value $385,856

    Last Listing Agent Cynthia Cartwright CENTURY 21 New Millennium

    18631 Cherryfield Rd, Drayden, MD 20630
    • /79

      Est $627,533 Not Listed For Sale

      18822 McKays Beach Rd, Leonardtown, MD 20650

      • 2 Beds
      • 3 Baths
      • 1,962 Sq Ft
      • Built 1998
      18822 McKays Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 9% Below List Price
      • $352/SF
      • 9 Days On Market

      Last Sold Price $690,000

      Last Listing Agent Ron Leonard Leonard Realty, Inc.

  • /9

    $45,000 Under Contract

    • Land
    • 0.38 Acre
    • $118,421 per Acre

    0 Saint Georges Park Rd, Piney Point, MD 20690

    You don't want to miss this! This lot has many features including a flat lot in a small quiet neighborhood and a short walking distance to water views. This lot includes 1 public EDU for sewer connection and a well will be required. Clear this lot and it is ready to be built on! There are two lots available next to each other- Buy 1 lot or buy them both! This parcel includes lot 12, 14, and 16.

    Brittany Russell CENTURY 21 New Millennium

    0 Saint Georges Park Rd, Piney Point, MD 20690
  • /6

    $320,500 Sold Jun 13, 2025

    44662 Blake Creek Rd, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft
    • Built 1963

    Last Sold Summary

    • $238/SF
    • 5 Days On Market

    Current Estimated Value $327,779

    Last Listing Agent Ruth Mudd RE/MAX One

    44662 Blake Creek Rd, Leonardtown, MD 20650
    • /47

      Est $552,983 Not Listed For Sale

      20860 Autumn Mill Ct, Great Mills, MD 20634

      • 4 Beds
      • 3.5 Baths
      • 5,056 Sq Ft
      • Built 2011
      20860 Autumn Mill Ct, Great Mills, MD 20634

      Last Sold Summary

      • 1% Above List Price
      • $109/SF
      • 74 Days On Market

      Last Sold Price $550,000

      Last Listing Agent James Willard Keller Williams Preferred Properties

  • /7

    $79,900

    • Land
    • 3.57 Acres
    • $22,381 per Acre

    18832 Piney Point Rd, Valley Lee, MD 20692

    Welcome to 18832 Piney Point Road! This property spans 3.57 acres and includes two lots within one parcel. Build your dream home in the peaceful waterfront community of Piney Point, Maryland. This exceptional parcel offers a rare opportunity to create a custom residence surrounded by natural beauty, privacy, and coastal charm. Nestled near the Potomac River, the property provides a serene setting

    Jonathan Benya EXP Realty, LLC

    18832 Piney Point Rd, Valley Lee, MD 20692
  • /42

    $555,000 Sold Sep 26, 2025

    21137 Marigold St, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,382 Sq Ft
    • Built 2003

    Last Sold Summary

    • $233/SF
    • 6 Days On Market

    Current Estimated Value $560,749

    Last Listing Agent Shem varhaftik District Pro Realty

    21137 Marigold St, Leonardtown, MD 20650
    • /37

      Est $288,010 Not Listed For Sale

      44874 Buck Redman Rd, Callaway, MD 20620

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1987
      44874 Buck Redman Rd, Callaway, MD 20620

      Last Sold Summary

      • 1% Below List Price
      • $289/SF
      • 4 Days On Market

      Last Sold Price $291,000

      Last Listing Agent Lesa Clark Redfin Corp

  • /2

    $399,900

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    17863 2nd St, Tall Timbers, MD 20690

    Freshly painted and ready for it's next chapter! This delightful 3-bedroom home in Tall Timbers offers comfortable living with plenty of potential to make it your own. Featuring a light and bright interior with new paint throughout, it’s the perfect canvas for your personal style. Enjoy the peaceful surroundings of this sought-after community while still being just minutes from local

    Robin Cavallaro RE/MAX Realty Group

    17863 2nd St, Tall Timbers, MD 20690
  • /12

    $580,000 Sold Oct 24, 2025

    20411 Monte Carlo Ln, Lexington Park, MD 20653

    • 5 Beds
    • 3.5 Baths
    • 3,768 Sq Ft
    • Built 2001

    Last Sold Summary

    • $154/SF
    • 42 Days On Market

    Current Estimated Value $600,603

    Last Listing Agent Thomas Hennerty NetRealtyNow.com, LLC

    20411 Monte Carlo Ln, Lexington Park, MD 20653
    • /37

      Est $453,437 Not Listed For Sale

      45154 Lighthouse Rd, Piney Point, MD 20674

      • 2 Beds
      • 1.5 Baths
      • 1,026 Sq Ft
      • Built 1945
      45154 Lighthouse Rd, Piney Point, MD 20674

      Last Sold Summary

      • 6% Below List Price
      • $468/SF
      • 13 Days On Market

      Last Sold Price $480,200

      Last Listing Agent Matthew Burgan Infinitas Realty Group

  • /10

    $1,999,999

    • 4 Beds
    • 2 Baths
    • 2,744 Sq Ft

    42520 Riverwinds Dr, Leonardtown, MD 20650

    Seller is entertaining offers now. Looking for elbow room? Look no further—this property offers plenty of land! It borders the Potomac River and Poplar Hill Creek, featuring expansive farmland and forested areas. Ideal for outdoor enthusiasts and nature lovers, this unique property offers breathtaking sunsets. Correct acreage is 165 acres. Don't miss out on this unique opportunity.

    John Gatton CENTURY 21 New Millennium

    42520 Riverwinds Dr, Leonardtown, MD 20650
  • /43

    $710,000 Sold Jul 24, 2025

    21549 Point Lookout Rd, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 3,153 Sq Ft
    • Built 2001

    Last Sold Summary

    • $225/SF
    • 6 Days On Market

    Current Estimated Value $718,670

    Last Listing Agent MaryAnne Crewse O'Brien Realty ERA Powered

    21549 Point Lookout Rd, Leonardtown, MD 20650
    • /11

      Est $325,950 Not Listed For Sale

      17854 Saint Georges Park Rd, Tall Timbers, MD 20690

      • 3 Beds
      • 2 Baths
      • 1,392 Sq Ft
      • Built 1925
      17854 Saint Georges Park Rd, Tall Timbers, MD 20690

      Last Sold Summary

      • 16% Above List Price
      • $201/SF
      • 159 Days On Market

      Last Sold Price $280,000

      Last Listing Agent Daniel Demers Sell Your Home Services

  • /6

    $290,000

    • Land
    • 0.57 Acre
    • $508,772 per Acre

    20225 Point Lookout Rd, Great Mills, MD 20634

    Bring your vision to life with this unique opportunity in Great Mills! This offering includes four separate parcels, all zoned commercial—ideal for a wide range of business ventures. Access to public water and sewer. With access on both Route 5 and Flat Iron Road, the property offers exceptional visibility and access in a high-traffic area. Don’t miss the chance to invest in a prime location with

    Billy Rabbitt The Southside Group Real Estate

    20225 Point Lookout Rd, Great Mills, MD 20634
  • /2

    $150,000 Sold Mar 18, 2026

    Lot 5 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630

    • Land
    • 2.09 Acres
    • $71,770 per Acre

    Last Sold Summary

    • 1,263 Days On Market

    Last Listing Agent Charlotte Long EXP Realty, LLC

    Lot 5 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
    • /56

      Est $642,434 Not Listed For Sale

      21147 Catnip Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,296 Sq Ft
      • Built 2002
      21147 Catnip Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 9% Below List Price
      • $164/SF

      Last Sold Price $705,000

      Last Listing Agent MaryAnne Crewse O'Brien Realty

  • /3

    $125,000

    • Land
    • 2.58 Acres
    • $48,450 per Acre

    46080 Usher Ln, Valley Lee, MD 20692

    If you’re looking for a manageable homesite that still gives you breathing room, this 2.58-acre wooded lot in Valley Lee is a standout. Tucked into a quiet, natural setting, it offers the kind of privacy and space that’s getting harder to find—without feeling overwhelming. The parcel is partially cleared, making it easier to visualize your future home placement, driveway approach, and outdoor

    Robert Gauger EXP Realty, LLC

    46080 Usher Ln, Valley Lee, MD 20692

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