34

Chaptico, MD Houses for Sale

Section Image
  • 20098 Piney Point Rd, Callaway, MD 20620
    20098 Piney Point Rd, Callaway, MD 20620
    20098 Piney Point Rd, Callaway, MD 20620
    /67

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 5,939 Sq Ft

    20098 Piney Point Rd, Callaway, MD 20620

    Want to live near your business?! This beautiful and classic 3 bedroom, 2 and half bathroom rancher has well-maintained curb appeal and the interior to match, beginning with the flower bed enriched porch. From the front door you are greeted with a spacious living room great for relaxing and enjoying the view from the large picturesque windows. This area also includes a separate kitchen/dining

    Shanita Kelley Samson Properties

    20098 Piney Point Rd, Callaway, MD 20620
  • 46461 Porto Bello Ct, Drayden, MD 20630
    46461 Porto Bello Ct, Drayden, MD 20630
    46461 Porto Bello Ct, Drayden, MD 20630
    /75

    $680,000

    Open Sat 1PM - 3PM
    • 5 Beds
    • 3 Baths
    • 3,430 Sq Ft

    46461 Porto Bello Ct, Drayden, MD 20630

    Welcome to Porto Bello Court, tucked away on a quiet cul-de-sac in the sought after Porto Bello Estates community of Drayden. This beautifully designed two-story home offers an abundance of natural light, creating a warm and inviting atmosphere throughout its spacious floor plan. Thoughtfully designed with versatility in mind, the expansive layout provides endless possibilities for today’s

    Diana Washabaugh CENTURY 21 New Millennium

    46461 Porto Bello Ct, Drayden, MD 20630
  • 18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    /74

    $699,900

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    18937 Hodges Ln, Leonardtown, MD 20650

    If you've been dreaming of waterfront living, now is your chance. Whether you enjoy boating, fishing, crabbing, or simply relaxing while taking in breathtaking water views, this beautifully renovated home has it all. Step inside to discover a spacious, open-concept kitchen and family room designed for gathering and everyday living. The stunning backyard provides the perfect setting for

    Ingrid Butler CENTURY 21 New Millennium

    18937 Hodges Ln, Leonardtown, MD 20650
  • 20846 Autumn Mill Ct, Great Mills, MD 20634
    20846 Autumn Mill Ct, Great Mills, MD 20634
    20846 Autumn Mill Ct, Great Mills, MD 20634
    /58

    $499,990

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

    20846 Autumn Mill Ct, Great Mills, MD 20634

    Welcome to 20846 Autumn Mill Court! This inviting home features a welcoming brick and siding exterior, spacious living areas, and plenty of natural light throughout. The main level offers beautiful hardwood flooring, a cozy fireplace, and an open flow between the living and dining areas. The kitchen features ample cabinetry, stainless steel appliances, and a convenient layout for everyday living.

    James Archie Own Real Estate

    20846 Autumn Mill Ct, Great Mills, MD 20634
  • 44911 Buck Redman Rd, Callaway, MD 20620
    44911 Buck Redman Rd, Callaway, MD 20620
    /2

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft

    44911 Buck Redman Rd, Callaway, MD 20620

    Nestled on a serene 2.17-acre lot, this charming ranch-style home offers a perfect blend of comfort and nature. Surrounded by lush trees and partly wooded areas, the property provides a tranquil retreat, ideal for those seeking peace and privacy. Imagine sipping your morning coffee while enjoying views of the garden and woods from your rear yard, where you can create your own outdoor oasis.

    Sheila Milburn Coldwell Banker Premier

    44911 Buck Redman Rd, Callaway, MD 20620
  • 19166 N Porto Bello Dr, Drayden, MD 20630
    19166 N Porto Bello Dr, Drayden, MD 20630
    19166 N Porto Bello Dr, Drayden, MD 20630
    /50

    $776,220

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,253 Sq Ft

    19166 N Porto Bello Dr, Drayden, MD 20630

    The PARKER Model, Elevation One ** Move in Ready** 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 Floor Bedrooms with private Bath *** OPEN

    Lisa Riggleman RE/MAX One

    19166 N Porto Bello Dr, Drayden, MD 20630
  • 43954 Main Way Rd, Leonardtown, MD 20650
    43954 Main Way Rd, Leonardtown, MD 20650
    43954 Main Way Rd, Leonardtown, MD 20650
    /28

    $469,900

    • 3 Beds
    • 3 Baths
    • 1,691 Sq Ft

    43954 Main Way Rd, Leonardtown, MD 20650

    Set on a level, open corner lot with a small view of the Potomac River—and best of all, **NO HOA**—this well-maintained split-foyer offers comfortable living, thoughtful updates, and a backyard designed for entertaining. A blacktop driveway provides a clean, finished approach to the oversized two-car garage, which accommodates two vehicles with plenty of additional room. The main level features

    Danny Martin Keller Williams Flagship

    43954 Main Way Rd, Leonardtown, MD 20650
  • 46234 Stasha Ct, Drayden, MD 20630
    46234 Stasha Ct, Drayden, MD 20630
    46234 Stasha Ct, Drayden, MD 20630
    /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
  • 19103 Windsor Ct, Drayden, MD 20630
    19103 Windsor Ct, Drayden, MD 20630
    19103 Windsor Ct, 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
  • 45210 Blue Water Ln, Piney Point, MD 20674
    45210 Blue Water Ln, Piney Point, MD 20674
    45210 Blue Water Ln, Piney Point, MD 20674
    /7

    $499,900

    Coming Soon Sep 23
    • 4 Beds
    • 2.5 Baths
    • 2,184 Sq Ft

    45210 Blue Water Ln, Piney Point, MD 20674

    Kimberly St. Laurent RE/MAX One

    45210 Blue Water Ln, Piney Point, MD 20674
  • 44450 Schumann Way, Leonardtown, MD 20650
    44450 Schumann Way, Leonardtown, MD 20650
    44450 Schumann Way, Leonardtown, MD 20650
    /77

    $695,000

    • 5 Beds
    • 2.5 Baths
    • 2,953 Sq Ft

    44450 Schumann Way, Leonardtown, MD 20650

    Welcome to this beautiful custom-built home situated on over 4 acres, offering an incredible combination of space, privacy, and versatility. A welcoming covered front porch and mature landscaping create beautiful curb appeal and the perfect place to sit back and enjoy the peaceful surroundings. Inside, you’ll find a thoughtfully designed floor plan featuring a main-level primary suite, spacious

    Jesieryl Hartzer CENTURY 21 New Millennium

    44450 Schumann Way, Leonardtown, MD 20650
  • 45776 Boothe Rd, Drayden, MD 20630
    45776 Boothe Rd, Drayden, MD 20630
    45776 Boothe Rd, Drayden, MD 20630
    /94

    $3,500,000

    • 3 Beds
    • 2 Baths
    • 4,541 Sq Ft

    45776 Boothe Rd, Drayden, MD 20630

    Welcome to Timerity, a natural sanctuary tucked away on an 189-acre waterfront estate where Southern Maryland history, productive farmland, mature woods and protected tidal waters come together in one extraordinary property.Documented by the Maryland Historical Trust as Timerity Farm, the property reflects the agricultural and maritime heritage of the Drayden area and the historic St.

    Sharon Cox Century 21 Redwood Realty

    45776 Boothe Rd, Drayden, MD 20630
  • 45846 Kingfisher Ct, Lexington Park, MD 20653
    45846 Kingfisher Ct, Lexington Park, MD 20653
    45846 Kingfisher Ct, Lexington Park, MD 20653
    /42

    $589,000

    $14K PRICE INCREASE
    • 6 Beds
    • 3.5 Baths
    • 4,496 Sq Ft

    45846 Kingfisher Ct, Lexington Park, MD 20653

    Welcome to nearly 5,000 sq. ft. of finished living space offering an exceptional blend of comfort, versatility, and entertainment. This spacious home features 6 bedrooms, 3.5 bathrooms, a dedicated office with French doors, and an impressive 600 sq. ft. primary suite with cathedral ceilings, a walk-in closet, and a large en-suite bathroom featuring dual sinks and a luxurious sunken Jacuzzi tub.

    Josh Dill Home Towne Real Estate

    45846 Kingfisher Ct, Lexington Park, MD 20653
  • 46200 Greens Rest Way, Great Mills, MD 20634
    46200 Greens Rest Way, Great Mills, MD 20634
    46200 Greens Rest Way, Great Mills, MD 20634
    /92

    $970,000

    • 3 Beds
    • 2.5 Baths
    • 2,590 Sq Ft

    46200 Greens Rest Way, Great Mills, MD 20634

    Welcome to 46200 Greens Rest Way, a truly special waterfront retreat tucked away on more than 13 acres with approximately 200 feet of frontage along the beautiful St. Mary’s River. Surrounded by mature woodland, tidal marsh and meandering creeks, this peaceful setting offers exceptional privacy, abundant wildlife and a rare connection to nature.Inside, extensive windows and skylights fill

    Robin Errington CENTURY 21 New Millennium

    46200 Greens Rest Way, Great Mills, MD 20634
  • 17597 Whitestone Dr, Tall Timbers, MD 20690
    17597 Whitestone Dr, Tall Timbers, MD 20690
    17597 Whitestone Dr, Tall Timbers, MD 20690
    /91

    $875,000

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

    17597 Whitestone Dr, Tall Timbers, MD 20690

    The Landings at Piney Point is a highly sought-after waterfront community offering exceptional amenities and a true coastal lifestyle. Residents enjoy one of the most beautiful private beaches in Southern Maryland, along with a community pool, tennis court, playground, harbor with boat slips, boat trailer storage, and more.Whether you enjoy boating, fishing, kayaking, or simply relaxing by

    Dawn Wood O'Brien Realty ERA Powered

    17597 Whitestone Dr, Tall Timbers, MD 20690
  • 19335 Greens Crossing Ct, Great Mills, MD 20634
    19335 Greens Crossing Ct, Great Mills, MD 20634
    19335 Greens Crossing Ct, Great Mills, MD 20634
    /62

    $585,000

    $15K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,436 Sq Ft

    19335 Greens Crossing Ct, Great Mills, MD 20634

    **SELLER OFFERING $10,000 FLOORING CREDIT WITH ACCEPTABLE OFFER** Classic colonial in desirable The Crossing at Riverside Farms neighborhood. Feel like you're in the country on this 1+ acre lot but only minutes to shopping, schools, parks and Pax River Base. Nice open floor plan features a generous open floor plan with spacious kitchen that has ample cabinet and counter space, walk-in pantry,

    Jennifer Mullennix CENTURY 21 New Millennium

    19335 Greens Crossing Ct, Great Mills, MD 20634
  • 21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    /74

    $690,000

    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    21395 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21395 Fairwood Ct., where space, comfort, and community come together on 0.85 acres in one of Leonardtown’s most desirable neighborhoods. Tucked near the end of a quiet street by the cul-de-sac, this 4-bedroom, 3.5-bath home offers more than 3,500 square feet of finished living space, a finished basement, and a large, level backyard with room to truly enjoy.Inside, a bright and

    Lauren Garner EXP Realty, LLC

    21395 Fairwood Ct, Leonardtown, MD 20650
  • 45703 Tennyhill St, California, MD 20619
    45703 Tennyhill St, California, MD 20619
    45703 Tennyhill St, California, MD 20619
    /60

    $649,900

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

    45703 Tennyhill St, California, MD 20619

    Nestled in the prestigious Elizabeth Hills Phase 4, this exquisite Colonial residence redefines luxury living. Built in 2020, this stunning home boasts 3,526 square feet of meticulously designed space, offering an unparalleled blend of elegance and modern comfort. Step inside to discover a harmonious layout featuring five spacious bedrooms and three and a half opulent bathrooms, perfect for both

    Matthew Burgan Infinitas Realty Group

    45703 Tennyhill St, California, MD 20619
  • 20893 Dry Mill St, Great Mills, MD 20634
    20893 Dry Mill St, Great Mills, MD 20634
    20893 Dry Mill St, Great Mills, MD 20634
    /66

    $455,000

    • 4 Beds
    • 3 Baths
    • 2,414 Sq Ft

    20893 Dry Mill St, Great Mills, MD 20634

    This 4 bedroom, 3 bath colonial in Cecil's Mill has been updated and improved, and is ready for new owners! The property includes brand new stainless steel appliances in the kitchen, new light fixtures, and an open layout for gathering on either the upper or lower levels.As you enter the home, there is an upper floor and a lower floor immediately available from the foyer. The upper level

    Danny Morris O'Brien Realty ERA Powered

    20893 Dry Mill St, Great Mills, MD 20634
  • 17863 2nd St, Tall Timbers, MD 20690
    17863 2nd St, Tall Timbers, MD 20690
    17863 2nd St, Tall Timbers, MD 20690
    /21

    $349,900

    $45K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    17863 2nd St, Tall Timbers, MD 20690

    Welcome to life in Tall Timbers — where peaceful surroundings, waterfront charm, and everyday comfort come together beautifully.This freshly updated 3-bedroom home is completely move-in ready with brand new carpet, newly refinished hardwood floors, and fresh paint throughout. The light-filled interior creates a warm and inviting feel from the moment you walk in.The spacious layout

    Robin Cavallaro RE/MAX Realty Group

    17863 2nd St, Tall Timbers, MD 20690
  • 17480 Lighthouse Commons Dr, Piney Point, MD 20674
    17480 Lighthouse Commons Dr, Piney Point, MD 20674
    17480 Lighthouse Commons Dr, Piney Point, MD 20674
    /44

    $629,900

    New Construction Open Sat 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 2,465 Sq Ft

    17480 Lighthouse Commons Dr, Piney Point, MD 20674

    Brand-New Rambler Near Piney Point Lighthouse! Experience the perfect blend of modern comfort and coastal charm in this beautifully crafted new construction rambler. Featuring luxury vinyl plank flooring, quartz counters, two tone cabinets, stainless appliances & custom tiled shower. This thoughtfully designed home offers a spacious family room, separate dining room, and a large eat-in kitchen

    Carol Kalmus-Choporis Century 21 Redwood Realty

    17480 Lighthouse Commons Dr, Piney Point, MD 20674
  • 17266 Larimer St, Piney Point, MD 20674
    17266 Larimer St, Piney Point, MD 20674
    17266 Larimer St, Piney Point, MD 20674
    /7

    $165,000

    $70K PRICE INCREASE
    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft

    17266 Larimer St, Piney Point, MD 20674

    Opportunity knocks in Piney Point at 17266 Larimer St! This 2bd/1ba rancher offers a blank slate for investors or handy homeowners to customize. Since utilities are already in place, the renovation is mostly cosmetic and allows for multiple exit strategies. This water-oriented community has a history of strong sales with properties moving quickly! Bring your contractor and vision to make this

    Ben Garner Cummings & Co. Realtors

    17266 Larimer St, Piney Point, MD 20674
  • 17320 Potomac Sands Dr, Piney Point, MD 20674
    17320 Potomac Sands Dr, Piney Point, MD 20674
    17320 Potomac Sands Dr, Piney Point, MD 20674
    /47

    $549,900

    Open Sat 11AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 2,288 Sq Ft

    17320 Potomac Sands Dr, Piney Point, MD 20674

    Nestled in the charming Potomac Sands community, and within walking distance of the Potomac River, sandy beaches, and scenic walking trails, this exquisite Colonial-style home offers a perfect blend of comfort and modern living. Step inside to discover a warm and inviting interior, highlighted by beautiful wood floors and an abundance of natural light. The heart of the home is the gourmet

    Deborah Radvany EXP Realty, LLC

    17320 Potomac Sands Dr, Piney Point, MD 20674
  • 20824 Flour Mill Ct, Great Mills, MD 20634
    20824 Flour Mill Ct, Great Mills, MD 20634
    20824 Flour Mill Ct, Great Mills, MD 20634
    /68

    $559,000

    $10K PRICE INCREASE
    • 5 Beds
    • 4.5 Baths
    • 2,968 Sq Ft

    20824 Flour Mill Ct, Great Mills, MD 20634

    Welcome to 20824 Flour Mill Ct., in the sought-after neighborhood of Cecil's Mill in St. Mary's County! With over 4,300 square feet, this traditional 5-bedroom, 4.5-bath home is sure to meet your needs and exceed your expectations. Located on a premium lot, enjoy a direct view of the community pond and the green space beyond. From the inviting front porch, you enter a bright interior with

    Brooke Matthews RE/MAX One

    20824 Flour Mill Ct, Great Mills, MD 20634
  • 19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    /140

    $15,000,000

    • 6 Beds
    • 4.5 Baths
    • 5,500 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    OPEN HOUSES BY APPOINTMENT. PLEASE COME AND TAKE A LOOK AT THIS MAGNIFICENT 500 ACRE ESTATE WHERE THE FOUNDING FATHER'S ONCE MINGLED!Mulberry Fields is one of those rare places where the land itself tells the story. The mile-long cedar avenue announces the approach, its rows planted at an ever-widening angle to draw the eye toward the Potomac below, a feat of 18th-century landscape design

    Kornelia Stuphan Long & Foster Real Estate, Inc.

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • 20851 Autumn Mill Ct, Lexington Park, MD 20653
    20851 Autumn Mill Ct, Lexington Park, MD 20653
    20851 Autumn Mill Ct, Lexington Park, MD 20653
    /41

    $479,000

    Open Sun 10AM - 12PM $20K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,413 Sq Ft

    20851 Autumn Mill Ct, Lexington Park, MD 20653

    Welcome to this spacious split-foyer home in the desirable Cecil’s Mill community. Offering approximately 2,413 square feet of living space, this home features five bedrooms and three full bathrooms with plenty of room to spread out. The main level offers a comfortable, open layout filled with natural light and an inviting kitchen featuring stainless steel appliances, plenty of workspace, and an

    Laura Holley O'Brien Realty ERA Powered

    20851 Autumn Mill Ct, Lexington Park, MD 20653
  • 44971 Shore Dr, Tall Timbers, MD 20690
    44971 Shore Dr, Tall Timbers, MD 20690
    44971 Shore Dr, Tall Timbers, MD 20690
    /90

    $399,900

    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft

    44971 Shore Dr, Tall Timbers, MD 20690

    **Instant equity! Priced below comps.**Room for everyone, all on one level! Completely renovated in 2026, this spacious 4-bedroom, 3-full-bath home offers 2,280 square feet of thoughtfully updated living space on a generous 30,000-square-foot lot in the water-oriented community of Tall Timbers.Step inside to soaring vaulted ceilings and a bright, open main living space where

    Emily Watts Real Broker, LLC

    44971 Shore Dr, Tall Timbers, MD 20690
  • 19495 Point Lookout Rd, Lexington Park, MD 20653
    19495 Point Lookout Rd, Lexington Park, MD 20653
    19495 Point Lookout Rd, Lexington Park, MD 20653
    /28

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    19495 Point Lookout Rd, Lexington Park, MD 20653

    Nestled on a 0.69-acre lot, this charming ranch-style home offers a perfect blend of comfort and community in the centrally located Park Hall location near PAX River NAS. . New paint throughout and an added beautiful family room with fireplace hearth just waiting for your woodstove addition. Ample deck outback for entertaining and large, private backyard. Woodfloors throughout and dedicated

    Charlotte Long EXP Realty, LLC

    19495 Point Lookout Rd, Lexington Park, MD 20653
  • 19163 N Porto Bello Ln, Drayden, MD 20630
    19163 N Porto Bello Ln, Drayden, MD 20630
    19163 N Porto Bello Ln, Drayden, MD 20630
    /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
  • 45433 Drayden Rd, Valley Lee, MD 20692
    45433 Drayden Rd, Valley Lee, MD 20692
    45433 Drayden Rd, Valley Lee, MD 20692
    /28

    $2,250,000

    Coming Soon Sep 30
    • 4 Beds
    • 4 Baths
    • 4,228 Sq Ft

    45433 Drayden Rd, Valley Lee, MD 20692

    Welcome to Mount Olive Farm! A breathtaking 39-acre horse farm featuring a beautifully restored manor home originally built in 1880. Rich in history and thoughtfully updated over the years, this exceptional estate seamlessly blends timeless character with modern amenities.The home features a stunning gourmet kitchen addition equipped with a commercial-grade range, Viking double ovens, a

    Carol Kalmus-Choporis Century 21 Redwood Realty

    45433 Drayden Rd, Valley Lee, MD 20692
  • 20410 Chingville Rd, Leonardtown, MD 20650
    20410 Chingville Rd, Leonardtown, MD 20650
    20410 Chingville Rd, Leonardtown, MD 20650
    /4

    $450,000

    Coming Soon Sep 30
    • 4 Beds
    • 3 Baths
    • 2,604 Sq Ft

    20410 Chingville Rd, Leonardtown, MD 20650

    This well-maintained 2004 ranch-style home offers 2,604 square feet of functional living space on a private, non-HOA 2-acre lot. The interior features four spacious bedrooms, three full bathrooms, and an open-concept layout that seamlessly connects the main living and dining areas. A fully finished basement provides flexible additional square footage ideal for a home office, media room, or gym.

    Billy Rabbitt The Southside Group Real Estate

    20410 Chingville Rd, Leonardtown, MD 20650
  • 20953 Pintail Ct, Callaway, MD 20620
    20953 Pintail Ct, Callaway, MD 20620
    /2

    $515,000

    Coming Soon Oct 1
    • 4 Beds
    • 2.5 Baths
    • 2,731 Sq Ft

    20953 Pintail Ct, Callaway, MD 20620

    Welcome home to this beautifully maintained Colonial, lovingly cared for by its original owner and ideally located in a quiet cul-de-sac! From the moment you arrive, the professional landscaping, hardscaping, inviting front porch, and Rain Bird underground irrigation system set the tone for the pride of ownership found throughout. Inside, you'll find fresh paint, new light fixtures, recessed

    Kimberly Scott Century 21 Redwood Realty

    20953 Pintail Ct, Callaway, MD 20620
  • 45694 Tennyhill St, California, MD 20619
    45694 Tennyhill St, California, MD 20619
    45694 Tennyhill St, California, MD 20619
    /72

    $589,900

    • 5 Beds
    • 3.5 Baths
    • 3,792 Sq Ft

    45694 Tennyhill St, California, MD 20619

    Tucked away on a quiet street, this thoughtfully designed home delivers the kind of space and flexibility for your lifestyle. The open-concept main level makes everyday life easy, while the extended kitchen is built to be the gathering spot, featuring granite countertops, stainless steel appliances, a large center island, and a convenient butler’s pantry. A separate dining room adds the perfect

    Randall Utz EXP Realty, LLC

    45694 Tennyhill St, California, MD 20619
  • 20999 Black Duck Ct, Callaway, MD 20620
    20999 Black Duck Ct, Callaway, MD 20620
    20999 Black Duck Ct, Callaway, MD 20620
    /51

    $389,900

    • 3 Beds
    • 2.5 Baths
    • 1,588 Sq Ft

    20999 Black Duck Ct, Callaway, MD 20620

    Welcome to this beautifully maintained Colonial nestled at the end of a quiet cul-de-sac in the Hunting Quarters neighborhood. With 3 bedrooms, 2.5 baths, a front-loading garage, and a private fenced backyard, this home offers a comfortable blend of everyday living and easy entertaining.The main level features a spacious living room and a separate dining room with a door leading directly to

    Vicky Horsmon EXP Realty, LLC

    20999 Black Duck Ct, Callaway, MD 20620
Maryland St Marys County

Houses for Sale in Chaptico, MD

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group