5,217

Chaptico, MD Homes

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  • /35

    $329,000 Sold Aug 08, 2025

    • 1,242 Sq Ft
    • $265/SF
    • 60 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 2012

    44964 Hewitt Rd, Callaway, MD 20620

    This 3 bedroom 1 bath rambler is located on a 2.01 acre lot. It backs to woods and also on the right side. There is a open feeling when standing in the front yard that also gives privacy due to the distance. The house is handicap equipped with a nice ramp on the side entrance as well as rails and handles in the bathroom tub and large shower.

    Alan Smith CENTURY 21 New Millennium

    44964 Hewitt Rd, Callaway, MD 20620
    • /55

      Est $572,685 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
  • /56

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 2,205 Sq Ft

    21056 Woodmere Dr, Leonardtown, MD 20650

    Nice Colonial with Covered Front Porch with concrete, Brick paver sidewalk and step, front load two car garage with exterior door to back yard. Storm Front Door with Side lights, Formal Living Room with Crown Molding, Dining Room Crown and Chair Molding, Hardwood Flooring in Foyer, Hall and Powder Room. Nice Kitchen with Center Island granite countertops, ceramic backsplash, Ceiling Light, New

    Kathryn Mausen Coldwell Banker Jay Lilly Real Estate

    21056 Woodmere Dr, Leonardtown, MD 20650
  • /46

    $410,000 Sold Aug 05, 2025

    • 2,505 Sq Ft
    • $164/SF
    • 4 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1984

    19960 Flat Iron Rd, Great Mills, MD 20634

    This distinctive contemporary home offers a rare departure from the ordinary. Nicely renovated between 2018 and 2023, nestled on a lush landscaped 1-acre lot, the home blends modern updates with a peaceful retreat type setting.With over 2,500 square feet, this 2-story home includes a full-size bonus attic (third floor), providing flexibility of a 5th bedroom. Two fully updated

    Tracey Summers CENTURY 21 New Millennium

    19960 Flat Iron Rd, Great Mills, MD 20634
    • /12

      Est $441,367 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths

      22030 Victorian Dr, California, MD 20619

      22030 Victorian Dr, California, MD 20619
  • /41

    $615,000

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

    20591 Chestnut Ridge Dr, Leonardtown, MD 20650

    Welcome to this well-built colonial on a corner lot in the picturesque corner 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

    Lauren Garner EXP Realty, LLC

    20591 Chestnut Ridge Dr, Leonardtown, MD 20650
  • /17

    $699,900 Sold Jul 31, 2025

    • 2,489 Sq Ft
    • $281/SF
    • 0 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2025

    17470 Lighthouse Commons Dr, Piney Point, MD 20674

    Custom Home with Main-Level Master SuiteThis stunning custom home features an open floor plan with 9' ceilings and a dramatic two-story great room. Enjoy luxurious touches throughout, including ceramic tiled shower and beautiful finishes. The main level has durable LVP flooring, while outdoor living is enhanced with both a charming front porch and a spacious, screened back porch. Upper

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    17470 Lighthouse Commons Dr, Piney Point, MD 20674
    • /76

      Est $568,455 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
  • /45

    $589,000

    • 4 Beds
    • 2.5 Baths
    • 3,412 Sq Ft

    20814 Deer Wood Park Dr, Leonardtown, MD 20650

    This spacious 4-bedroom Colonial offers the perfect blend of charm, comfort, and privacy on a beautifully treed 4 acre lot. The first floor features a private office/den, formal living room, and elegant dining room. The large kitchen includes a cozy breakfast nook and opens to a step-down family room with a slider leading to a screened-in porch—ideal for indoor-outdoor living.Upstairs,

    Cynthia Crispell CENTURY 21 New Millennium

    20814 Deer Wood Park Dr, Leonardtown, MD 20650
  • /74

    $682,000 Sold Jul 30, 2025

    • 3,031 Sq Ft
    • $225/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2003

    19272 Vanderhoof Ln, Valley Lee, MD 20692

    Welcome to 19272 Vanderhoof Lane, an elegant and expansive 4-bedroom, 2.5-bath rambler nestled on 7.845 peaceful acres in beautiful Valley Lee. With over 3,000 finished square feet, this custom home blends luxury features with a serene, private setting—perfect for those seeking space, comfort, and style.Step inside to soaring 10’ ceilings, 8’ doors, and walls of large windows that flood the

    Janet Weaver RE/MAX One

    19272 Vanderhoof Ln, Valley Lee, MD 20692
    • /27

      Est $257,218 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
  • /59

    $624,900

    • 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
  • /41

    $541,000 Sold Jul 25, 2025

    • 2,356 Sq Ft
    • $230/SF
    • 17 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1996

    20955 Aster Dr, Callaway, MD 20620

    Well maintained by the original owners, this beautiful home sits on a private, 2-acre lot. Recent updates include a roof (8 years old), Heat pump & AC coil (2020), and a hot water heater (2025). The interior has been freshly painted, and new carpet on the main level. Enjoy outdoor living on the maintenance-free deck, replaced in 2012, or relax on the charming front porch. The family room features

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    20955 Aster Dr, Callaway, MD 20620
    • /53

      Est $365,428 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
  • /32

    $679,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,643 Sq Ft

    46234 Stasha Ct, Drayden, MD 20630

    *** To Be Built *** ONE ACRE Plus Wooded Level LOT *** THE CANTERBURY II Model *** 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 CANTERBURY II

    Lisa Riggleman RE/MAX One

    46234 Stasha Ct, Drayden, MD 20630
  • /55

    $495,000 Sold Jul 24, 2025

    • 3,290 Sq Ft
    • $150/SF
    • 1 Day On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2002

    45877 Skipjack Dr, Lexington Park, MD 20653

    Less than ten minutes from the PAX River gate, this home was built for real life, not just pictures. It’s spacious without feeling oversized, updated where it counts, and gives everyone the room they need.There are four bedrooms upstairs, a dedicated office on the main level, and a finished walk-out basement with a full bath, flexible living space, and actual storage, so you’re not

    Neil Smith Blackwell Real Estate, LLC

    45877 Skipjack Dr, Lexington Park, MD 20653
    • /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
  • /35

    $559,900 New Construction

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

    17490 Lighthouse Commons Dr, Piney Point, MD 20674

    Lighthouse Commons | Piney PointNew Construction | Ready July 2025This popular 4-bedroom home, thoughtfully upgraded for modern living. Highlights include granite countertops, stainless steel appliances, and luxury vinyl plank flooring throughout the main level. The master suite features a custom-tiled shower, while 9' ceilings add an airy feel. Exterior upgrades include a sodded lawn

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    17490 Lighthouse Commons Dr, Piney Point, MD 20674
  • /43

    $710,000 Sold Jul 24, 2025

    • 3,153 Sq Ft
    • $225/SF
    • 6 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2001

    21549 Point Lookout Rd, Leonardtown, MD 20650

    Contemporary Farmhouse Living on over 24 acres! Drive down the lane past some of your pasture acreage on the left to your 3,000+ sf home backing to mature trees and wooded trails. A small pond is also located on the property. Possibilities abound with the level acreage in front! The property is located between Leonardtown and Callaway close to the Saint Mary's Rive State Park area. Close to

    MaryAnne Crewse O'Brien Realty ERA Powered

    21549 Point Lookout Rd, Leonardtown, MD 20650
    • /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
  • /45

    $635,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    19103 Windsor Ct, Drayden, MD 20630

    ** ONE ACRE Plus Wooded Level LOT *** The Stella Model or Select from one of our other Plans ** To Be Built ** Still time to Customize Selections and upgrades *** FABULOUS KITCHEN w/Super Island & Granite Counters *** Huge Pantry *** STAINLESS Appliances *** First Floor Primary Bedroom complete with walk in Closet *** Master Bath with Soak Tub and Walk in Shower *** Tow Additional Main Floor

    Lisa Riggleman RE/MAX One

    19103 Windsor Ct, Drayden, MD 20630
  • /24

    $247,000 Sold Jul 24, 2025

    • 700 Sq Ft
    • $353/SF
    • 32 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1942

    17253 Larimer St, Piney Point, MD 20674

    The seller is showing motivation with this most recent price reduction. Come and see nice finishing 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 more. Explore many opportunities

    Juan Aranda CENTURY 21 New Millennium

    17253 Larimer St, Piney Point, MD 20674
    • /79

      Est $695,922 Not Listed For Sale

      • 2 Beds
      • 3 Baths
      • 1,962 Sq Ft

      18822 McKays Beach Rd, Leonardtown, MD 20650

      18822 McKays Beach Rd, Leonardtown, MD 20650
  • /8

    $700,000 New Construction

    • 4 Beds
    • 3.5 Baths

    46175 N Greens Rest Dr, Great Mills, MD 20634

    One of the few remaining pristine lots left in Riverside Farms! 1.63 acre lot . 3500+ sq. ft. custom rambler with 4BR, 3-4 BA, basement with 9 ft. ceilings, 3 car sideload garage, and much more! This desirable neighborhood offers a community park, ball fields, walking trails, picnic areas, and community pier. A perfect place for your family! Conveniently located close to Leonardtown and Pax

    Joe and Judi Limerick CENTURY 21 New Millennium

    46175 N Greens Rest Dr, Great Mills, MD 20634
  • /69

    $622,500 Sold Jul 21, 2025

    • 2,642 Sq Ft
    • $236/SF
    • 16 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2003

    21143 Catnip Ct, Leonardtown, MD 20650

    Welcome to this stunning 4-bedroom, 2.5-bath home in the desirable Kingston Estatesneighborhood of Leonardtown. Lovingly maintained by the original owners, this homesits on a beautifully landscaped lot of nearly an acre, and is nestled in a quiet cul-de-sacthat offers both privacy and convenience.As you step inside, you’ll be greeted by the stunning Acacia wood floors that

    Melissa Rodriguez RE/MAX One

    21143 Catnip Ct, Leonardtown, MD 20650
    • /37

      Est $298,387 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft

      44874 Buck Redman Rd, Callaway, MD 20620

      44874 Buck Redman Rd, Callaway, MD 20620
  • /59

    $612,000 Pending

    • 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

    $906,500 Sold Jul 18, 2025

    • 2,167 Sq Ft
    • $418/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1980

    42239 Riverwinds Dr, Leonardtown, MD 20650

    Welcome to your waterfront retreat on the Potomac River! This well-maintained 3-bedroom, 2.5-bath rambler is perfectly situated on a level 1-acre lot with stunning panoramic water views from every rear-facing room, including all bedrooms. The spacious kitchen opens to a cozy family room with a wood-burning fireplace, ideal for relaxing or entertaining. Step out to the screened-in porch or

    Connie Fitzgerald RE/MAX One

    42239 Riverwinds Dr, Leonardtown, MD 20650
    • /37

      Est $502,795 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,026 Sq Ft

      45154 Lighthouse Rd, Piney Point, MD 20674

      45154 Lighthouse Rd, Piney Point, MD 20674
  • /24

    $575,000 Coming Soon

    • 4 Beds
    • 3 Baths
    • 3,094 Sq Ft

    20413 Scarlet Tanager Way, Leonardtown, MD 20650

    Spacious 4-Bedroom, 3-Bath Home on Private 7-Acre Setting!Welcome to your peaceful retreat! This home sits on a secluded 7-acre lot and offers room to relax, entertain, and enjoy nature.Inside, the living room features an arched ceiling, while the remodeled kitchen (2013) has granite countertops and new stainless steel appliances (2024). The cozy family room includes a fireplace with

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    20413 Scarlet Tanager Way, Leonardtown, MD 20650
  • /91

    $589,000 Sold Jul 18, 2025

    • 3,502 Sq Ft
    • $168/SF
    • 13 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2003

    21946 Short Bow Ct, California, MD 20619

    Classic Single-Story Elegance on Quiet Cul-de-Sac | Near State Park, NAS Pax River & SolomonsWelcome to this timeless single-story residence, gracefully nestled at the end of a quiet cul-de-sac. Located just minutes from the natural beauty of a nearby state park offering scenic trails and a tranquil lake, this home also enjoys convenient access to NAS Patuxent River (less than 10 miles),

    John Gatton CENTURY 21 New Millennium

    21946 Short Bow Ct, California, MD 20619
    • /11

      Est $298,489 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
  • /2

    $649,900 Open House 10/11

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

    21117 Catnip Ct, Leonardtown, MD 20650

    Absolutely stunning home in Leonardtown’s sought-after Kingston Subdivision! Perched on a hill with mature trees, beautiful landscaping, and plenty of open yard space, this 5BR/3.5BA home boasts over $165K in upgrades. Enjoy new high-efficiency HVAC systems (2023 & 2025), architectural roof (2018), luxury vinyl plank flooring, gourmet kitchen with granite countertops, tile backsplash, Kraus sink

    James Marcum CENTURY 21 New Millennium

    21117 Catnip Ct, Leonardtown, MD 20650
  • /39

    $404,990 Sold Jul 18, 2025

    • 2,332 Sq Ft
    • $174/SF
    • 55 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1998

    20880 Ark Ct, Lexington Park, MD 20653

    Price Reduction!!! Move in Ready!! Motivated Seller!! Come take a look at this lovely well cared for colonial in the sought after Bay Ridge Estates community! Home boasts large open sun-filled rooms with big picture windows throughout. House qualifies for USDA Zero Down Payment Loan. Check with your lender for loan qualification. There's 3 spacious bedrooms upstairs, 2 full updated baths, and a

    Christina Proctor HomeSmart

    20880 Ark Ct, Lexington Park, MD 20653
    • /56

      Est $673,211 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
  • /42

    $544,999 Under Contract

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

    21137 Marigold St, Leonardtown, MD 20650

    Imagine this: a spacious, thoughtfully designed home where bright natural light fills oversized rooms while still offering the privacy you crave. Hardwood floors, crown molding, and 9-foot ceilings creating an inviting atmosphere, and a full walk-out basement plus a laundry room with built-in cabinetry add practical living space. The master suite features a soaking tub and separate shower, and

    Shem varhaftik District Pro Realty

    21137 Marigold St, Leonardtown, MD 20650
  • /42

    $385,000 Sold Jul 17, 2025

    • 1,664 Sq Ft
    • $231/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1975

    45975 Bates Rd, Great Mills, MD 20634

    Welcome to this charming 3-bedroom, 2-bath rambler located in a quiet neighborhood with no HOA. Sitting on a spacious, flat corner lot, this home is ideal for outdoor living and entertaining. Enjoy the expansive 20x10 deck, inviting front porch, and a large paved driveway with plenty of room for multiple vehicles, an RV, or even a boat. A detached one-car garage and shed offer excellent storage

    Karen Taylor JPAR Real Estate Professionals

    45975 Bates Rd, Great Mills, MD 20634
    • /80

      Est $604,067 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,980 Sq Ft

      45475 Mount Olive Way, Valley Lee, MD 20692

      45475 Mount Olive Way, Valley Lee, MD 20692
  • /68

    $649,500 Under Contract

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

    21987 Short Bow Ct, California, MD 20619

    Welcome Home to 21987 Short Bow Ct in the sought-after Arrowhead Subdivision in California, MD! This beautifully updated move-in-ready 4-bed, 2.5-bath home offers approximately 3,500+ sq ft of living space on 2+ acres. Recent upgrades include a 600+ sq ft family room addition with wood burning fireplace, 29'x12' screened-in porch, 36'x20' concrete patio, renovated kitchen with granite countertops

    Jessica Licurgo Real Estate Made Simple, LLC

    21987 Short Bow Ct, California, MD 20619
  • /8

    $53,000 Sold Jul 17, 2025

    • Land
    • 0.20 Acre
    • $265,000 per Acre
    • 41 Days On Market

    45095 Blackwell Ct, Piney Point, MD 20674

    Tear down. Value in the lot. Aproximately $20,000 back fees for sewer to be paid by purchaser.SOLD AS IS, DO NOT Enter house.

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    45095 Blackwell Ct, Piney Point, MD 20674

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