33

Chaptico, MD Houses for Sale

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  • /5

    $500,000

    • 4 Beds
    • 2.5 Baths
    • 3,268 Sq Ft

    19809 Point Lookout Rd, Lexington Park, MD 20653

    HUGE Price Reduction on an already good deal. All room sizes are estimates. Step inside to a large home that needs your finishing touches. The sale is AS IS. Most of the repairs needed are cosmetic, ie. flooring, painting, appliances, etc. This home has 2 main level bedrooms, sunroom, HUGE family room, large kitchen and dining area, laundry closet, and more. On the outside there is a HUGE 2

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (240) 261-5827

    19809 Point Lookout Rd, Lexington Park, MD 20653
  • /43

    $495,000

    • 6 Beds
    • 4 Baths
    • 3,536 Sq Ft

    45673 Cecil Mill Ct, Great Mills, MD 20634

    $10,000 SELLER CREDIT with an accepted offer! Pond View and Access! This home is located on a premium lot within the Cecil's Mill Community. Enjoy the panoramic views from this beautiful Colonial home featuring 6-bedroom, 4-bathroom. As you enter your home, Brazilian Cherry hardwood floors lead you into a formal sitting room with custom trim, chair-rail and crown molding throughout. The first

    Farrah Fuchs Redfin Corp

    45673 Cecil Mill Ct, Great Mills, MD 20634
  • /65

    $699,900

    • 4 Beds
    • 2.5 Baths
    • 2,724 Sq Ft

    17660 Driftwood Dr, Tall Timbers, MD 20690

    Welcome to your gateway to a life well-lived. Discover waterfront living in the prestigious Landings at Piney Point. This exquisite property offers tranquil views of Piney Point Creek, providing a serene backdrop for your daily life. Featuring high-quality finishes, including hardwood floors and crown molding, the interior speaks sophistication and warmth. Equipped with modern appliances, ample

    Michelle Camaioni RE/MAX One

    17660 Driftwood Dr, Tall Timbers, MD 20690
  • /55

    $640,000

    • 5 Beds
    • 3.5 Baths
    • 3,830 Sq Ft

    45656 Edge Mill Ct, Great Mills, MD 20634

    From the moment you step through the grand 2-story foyer, this home will take your breath away. Sunlight pours through Palladian windows and skylights, highlighting the rich hardwood floors, crown molding, and detailed craftsmanship throughout.The heart of the home is the chef’s kitchen—complete with stainless steel appliances, a spacious island, and a bright breakfast room with a

    Gianni Cavero-Aponte Coldwell Banker Realty

    45656 Edge Mill Ct, Great Mills, MD 20634
  • /64

    $610,000

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

    20411 Monte Carlo Ln, Lexington Park, MD 20653

    Welcome to your private retreat! This spacious 5-bedroom, 3.5-bath home sits at the end of a quiet private road on 2.29 beautifully manicured acres. With over 3,700 sq ft of finished living space across three levels, this home offers room to grow, entertain, and relax.The fully finished lower level includes a complete **in-law suite** with an updated kitchen, new flooring, bar seating,

    Thomas Hennerty NetRealtyNow.com, LLC

    20411 Monte Carlo Ln, Lexington Park, MD 20653
  • /118

    $639,000

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

    44906 Golden Eye Ct, Callaway, MD 20620

    You've heard it before but this time it's really true. You won't believe this custom built two story Colonial home has two finished basements and is all you could ever want in a home. As you enter the main level of the home, you are greeted with a grand foyer and hardwood floors that lead to the formal dining room and formal den/office/library. Moving to the rear of the home, the Tuscan style

    Kelly Padgett CENTURY 21 New Millennium

    44906 Golden Eye Ct, Callaway, MD 20620
  • /56

    $574,900

    • 4 Beds
    • 3.5 Baths
    • 3,465 Sq Ft

    20919 Ridge Path Way, Leonardtown, MD 20650

    Nestled on a serene and private 3.29-acre lot—plus an additional 0.5-acre parcel—20919 Ridge Path Way offers the perfect balance of seclusion and convenience in the heart of Leonardtown. This professionally upgraded 4-bedroom, 3.5-bath home delivers both peace of mind and high-end comfort with all major systems and appliances less than 5 years old.Step inside and experience a beautifully

    Matthew Burgan Infinitas Realty Group

    20919 Ridge Path Way, Leonardtown, MD 20650
  • /48

    $850,000

    • 4 Beds
    • 3 Baths
    • 1,900 Sq Ft

    924 Blackbeard Pond Rd, Hague, VA 22469

    New Beginnings! - Charming shoreline beach house located in the Ragged Point subdivision, less than a mile from Coles Point Marina and RV Resort! This property features your very own sandy beach, boasting over 100 feet of water frontage and a panoramic view of the lower Potomac River. This is a perfect beach for volleyball! You can enjoy your own private dock for fishing, crabbing, swimming,

    Dale Brandon Samson Properties

    924 Blackbeard Pond Rd, Hague, VA 22469
  • /40

    $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
  • /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
  • /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
  • /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
  • /22

    $729,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,456 Sq Ft

    18665 Hebb Way, Drayden, MD 20630

    TO BE BUILT; this pictured beautiful custom home on over 5 acres nestled in the Drayden countryside offers tranquility and expansive sunset skies, while still being within 15 minutes of schools and shopping! A Mednick Construction Home which includes 3 bedroom/2.5 baths, 9' ceilings, upgraded finishes, utilities, well, septic, permits and everything you need to have a move in ready beautiful

    Charlotte Long EXP Realty, LLC

    18665 Hebb Way, Drayden, MD 20630
  • /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
  • /68

    $794,905 New Construction

    • 4 Beds
    • 3.5 Baths

    19106 Windsor Ct, Valley Lee, MD 20692

    Immediate OCCUPANCY ** One ACRE Plus WOODED Level LOT ** THREE CAR GARAGE ** STUDY w/Accent Wall ** GOURMET Kitchen w/level 4 QUARTZ ** Custom BOX Ceiling above ISLAND ** FRENCH Door Refrigerator ** DOUBLE Wall Oven ** Custom PANTRY ** Upgraded LUXURY Vinyl Flooring** MASTER Suite w/ BOX Ceiling ** Walk in Closet W/CUSTOM Shelving ** MASTER Walk in SHOWER w/ Nitches & Accent Tile ** STONE

    Lisa Riggleman RE/MAX One

    19106 Windsor Ct, Valley Lee, MD 20692
  • /62

    $660,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 2,635 Sq Ft

    44591 Shallow Ford Ct, Tall Timbers, MD 20690

    Located in the desirable Landings at Piney Point, this waterfront property is a private retreat on a serene, wooded 1.5-acre lot. Surrounded by mature trees and a lush canopy-lined driveway, the home offers a rare sense of seclusion and immersion in nature, setting it apart from others in the community. Enjoy your own peaceful paradise with an assigned boat slip and boat lift at the

    Gabriela Agostinelli RE/MAX Realty Group

    44591 Shallow Ford Ct, Tall Timbers, MD 20690
  • /30

    $520,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 2,495 Sq Ft

    17850 4th St, Tall Timbers, MD 20690

    Coastal Charm in Tall Timbers!! Welcome to 17850 4th Street, a beautifully designed 4-bedroom, 3.5-bath coastal-style home offering over 2,450 square feet of living space just minutes from Saint George Island, public boat ramps, beaches, and parks. Step inside and be greeted by gleaming hardwood floors, soaring 9 ft ceilings, and an abundance of natural light that enhances the home’s

    Charlotte Long EXP Realty, LLC

    17850 4th St, Tall Timbers, MD 20690
  • /13

    $239,000

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

    20959 Redgate Ln, Leonardtown, MD 20650

    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 well-deserved TLC.This

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
  • /69

    $520,000

    • 4 Beds
    • 3.5 Baths
    • 2,802 Sq Ft

    17838 4th St, Tall Timbers, MD 20690

    Step into this beautifully upgraded and thoughtfully designed coastal-style home offering nearly 2,500 square feet of elevated living space and exceptional outdoor living. This home is located at the end of a dead end street and backs to a peaceful farm for added privacy and tranquility. This home is loaded with features that make everyday living feel like a retreat. The main level greets you

    Kimberly Scott RE/MAX Realty Group

    17838 4th St, Tall Timbers, MD 20690
  • /41

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,483 Sq Ft

    17309 Piney Point Rd, Piney Point, MD 20674

    Welcome to your dream coastal retreat, where luxury and convenience meet unparalleled natural beauty. This charming three-bedroom, two-bathroom home offers a perfect blend of modern comforts and serene surroundings, making it an ideal escape for those seeking both relaxation and adventure.Step inside to discover stunning luxury vinyl plank flooring throughout, paired with pristine tile

    John Gatton CENTURY 21 New Millennium

    17309 Piney Point Rd, Piney Point, MD 20674
  • /61

    $494,900

    • 4 Beds
    • 3.5 Baths
    • 3,592 Sq Ft

    20813 Skipjack Ct, Lexington Park, MD 20653

    Welcome to this beautifully updated 4-bedroom, 3.5-bath home offering the perfect blend of comfort, function, and flexibility. The main level features rich hardwood floors and a bright, open layout, with ceramic tile kitchen floors, quartz countertops, 42in cabinets and glass tiled backsplash . Home has 2-inch blinds throughout. A dedicated home office provides the ideal space for remote work,

    Olive Kelsey Paragon Real Estate Group, LLC

    20813 Skipjack Ct, Lexington Park, MD 20653
  • /42

    $445,000

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

    20966 Black Duck Ct, Callaway, MD 20620

    Hunting Quarter! Located in Callaway with current school zoning of Leonardtown HS, Leonardtown MS, and Piney Point ES. Quiet location within the community and situated near the end of a cul-de-sac with few cars driving by. 3 BR/3.5 BA with brand new finished basement that includes space for potential use as 4th BR and has a full bathroom! Kitchen located on the main level, has tons of counter

    Farrah Fuchs Redfin Corp

    20966 Black Duck Ct, Callaway, MD 20620
  • /31

    $540,000

    • 4 Beds
    • 2.5 Baths
    • 2,360 Sq Ft

    21312 Fox Wood Ln, California, MD 20619

    Welcome to 21312 Fox Wood Lane in the sought after Elizabeth Hills neighborhood, a charming 4-bedroom, 2-bath home nestled on a quiet cul-de-sac in California, MD. This beautifully maintained property features an updated kitchen, luxury vinyl plank flooring throughout, and a spacious primary suite with a private bath. The backyard is perfect for entertaining, with a beautiful deck with no

    William Rabbitt The Southside Group Real Estate

    21312 Fox Wood Ln, California, MD 20619
  • /64

    $429,999

    • 4 Beds
    • 3 Baths
    • 2,106 Sq Ft

    45044 Deagles Boatyard Rd, Tall Timbers, MD 20690

    Charming Cottage Home with Detached Workshop & Apartment in the St. Georges Beach Neighborhood.Welcome to this inviting 3-bedroom, 2-bath cottage nestled on a spacious corner lot in the St. Georges Beach neighborhood. Full of character and charm, this property offers a unique combination of comfortable living and versatile bonus spaces.The main home features a warm and functional

    Mike Jordan CENTURY 21 New Millennium

    45044 Deagles Boatyard Rd, Tall Timbers, MD 20690
  • /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
  • /123

    $1,999,000

    • 5 Beds
    • 6 Baths
    • 7,142 Sq Ft

    46369 Hattons Rest Ln, Lexington Park, MD 20653

    Welcome to 46369 Hattons Rest Ln – A Waterfront Masterpiece on the Historic St. Mary’s River!Experience timeless elegance and serene waterfront living in this exceptional all-brick colonial estate. Custom-built and thoughtfully designed, this 5-bedroom, 4 full/2 half-bath home boasts over 7,100 sq ft of refined living space and sits proudly along 1,100 feet of private shoreline.From the

    Natalya Ford EXP Realty, LLC

    46369 Hattons Rest Ln, Lexington Park, MD 20653
  • /139

    $20,000,000

    • 6 Beds
    • 4.5 Baths
    • 13,458 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    Welcome to Historic Mulberry Fields, situated on just under 500 acres of fertile land with a mile-long view of the Potomac River’s white sand shoreline, is truly one of a kind. As you drive along the cedar-lined driveway, you are transported back in time as the magnificent manor house appears in front of you. It is the only remaining Georgian manor house in St. Mary’s County today. From the south

    Kornelia Stuphan Long & Foster Real Estate, Inc.

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • /50

    $1,495,000

    • 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 DCEven 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

    David DeSantis TTR Sotheby's International Realty

    46502 Glen Mary Farm Rd, Park Hall, MD 20667
  • /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
  • /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
  • /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
  • /2

    $675,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,534 Sq Ft

    46442 Hyatt Ct, Drayden, MD 20630

    Welcome to 46442 Hyatt Court in Porto Bello Estates! This huge colonial is situated on over 3 acres of woods and nestled back off the cul-de-sac so you and your family can enjoy the serene privacy of the mature trees. Sellers have done a wonderful job maintaining this home and preparing it for its new owners. You will not be disappointed. Professional pics coming soon.

    Michele Hughes RE/MAX Realty Group

    46442 Hyatt Ct, Drayden, MD 20630
  • /2

    $400,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,988 Sq Ft

    20766 Wolftrap St, Lexington Park, MD 20653

    Charming Colonial with 3 bedrooms, 2 1/2 bathrooms and a 2 car garage. This home has a spacious living room with hardwood floors. The kitchen includes granite counters, backsplash, tile floors and updated appliances. The open concept kitchen and dining area have tile floors and create an opportunity to entertain and host guests with a flow throughout the main level of the home. The sliding

    Kelly Padgett CENTURY 21 New Millennium

    20766 Wolftrap St, Lexington Park, MD 20653
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