27

Chaptico, MD Homes for Sale with Garage

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  • 44905 Widgeon Place, Callaway, MD 20620
    44905 Widgeon Place, Callaway, MD 20620
    44905 Widgeon Place, Callaway, MD 20620
    /31

    $499,000

    • 5 Beds
    • 3.5 Baths
    • 3,257 Sq Ft

    44905 Widgeon Place, Callaway, MD 20620

    Welcome home to this well-maintained, beautifully landscaped property offering the perfect blend of convenience, comfort, and functionality! Ideally located just minutes from shopping, dining, and Patuxent River Naval Air Station (PAX NAS), this home makes daily commuting and errands a breeze. Inside, you'll find a spacious floor plan featuring a large primary suite with a private ensuite

    Agent Photo

    Amy Scott

    OE Realty

    44905 Widgeon Place, Callaway, MD 20620
  • 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
  • 18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    /19

    $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
  • 20980 Aster Dr, Callaway, MD 20620
    20980 Aster Dr, Callaway, MD 20620
    20980 Aster Dr, Callaway, MD 20620
    /3

    $625,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,052 Sq Ft

    20980 Aster Dr, Callaway, MD 20620

    Welcome to 20890 Aster Drive, where privacy, efficiency, and timeless charm come together on more than 4 peaceful acres in the heart of Callaway. This inviting Cape Cod offers the freedom of country living with no HOA, while providing exceptional value through major system upgrades that make homeownership both comfortable and economical. Step inside to discover a light-filled family room with

    Charlotte Long EXP Realty, LLC

    20980 Aster Dr, Callaway, MD 20620
  • 21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    /64

    $700,000

    Open Wed 5PM - 7PM
    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    21395 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21395 Fairwood Ct., an exceptional home offering over 3,500 square feet of finished living space on 0.85 acres in one of Leonardtown's most sought-after neighborhoods. Perfect for those looking to spread out and lay down roots. This spacious 4-bedroom, 3.5-bath home combines generous living areas, thoughtful updates, and a picturesque setting at the end of a quiet street near the

    Lauren Garner EXP Realty, LLC

    21395 Fairwood Ct, Leonardtown, MD 20650
  • 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
  • 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
  • 45776 Boothe Rd, Drayden, MD 20630
    45776 Boothe Rd, Drayden, MD 20630
    45776 Boothe Rd, Drayden, MD 20630
    /50

    $3,500,000

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

    45776 Boothe Rd, Drayden, MD 20630

    Welcome to a rare opportunity to acquire one of Southern Maryland's truly exceptional waterfront estates.Steeped in history that dates back to the mid-19th century, this remarkable property, historically known as Timerity Farm (also referred to as Westbury Farm), encompasses approximately 189 acres of farmland, mature woodland, and protected waterfront along School House Branch, with direct

    Sharon Cox Century 21 Redwood Realty

    45776 Boothe Rd, Drayden, MD 20630
  • 19166 N Porto Bello Dr, Drayden, MD 20630
    19166 N Porto Bello Dr, Drayden, MD 20630
    19166 N Porto Bello Dr, Drayden, MD 20630
    /25

    $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
  • 17480 Lighthouse Commons Dr, Piney Point, MD 20674
    17480 Lighthouse Commons Dr, Piney Point, MD 20674
    17480 Lighthouse Commons Dr, Piney Point, MD 20674
    /36

    $629,900

    New Construction $70K PRICE DROP
    • 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
  • 21983 Point Lookout Rd, Leonardtown, MD 20650
    21983 Point Lookout Rd, Leonardtown, MD 20650
    21983 Point Lookout Rd, Leonardtown, MD 20650
    /30

    $369,900

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21983 Point Lookout Rd, Leonardtown, MD 20650

    OWNER FINANCING AVAILABLE, no banks, call for details. Beautifully renovated rambler located in the highly desirable Leonardtown School District, offering the perfect blend of modern updates and peaceful living on almost 1-acre lot.This move-in ready home features 3 bedrooms and 2 full bathrooms, along with a 1-car garage as well as man cave, workshop, or bonus space. The home has been

    Natalya Ford RE/MAX One

    21983 Point Lookout Rd, Leonardtown, MD 20650
  • 17265 Crab Pot Ln, Piney Point, MD 20674
    17265 Crab Pot Ln, Piney Point, MD 20674
    17265 Crab Pot Ln, Piney Point, MD 20674
    /56

    $474,900

    • 4 Beds
    • 3 Baths
    • 2,112 Sq Ft

    17265 Crab Pot Ln, Piney Point, MD 20674

    Welcome to 17265 Crab Pot Lane, Piney Point, MD, a breathtaking 4-bedroom, 3-bathroom haven that exemplifies the perfect blend of luxury and tranquility. This home has undergone a complete professional renovation, offering the utmost in modern amenities and stylish finishes. Step inside to discover the allure of all-new high-end LVP flooring that spans throughout the entire home, providing a

    Matthew Burgan Infinitas Realty Group

    17265 Crab Pot Ln, Piney Point, MD 20674
  • 17295 Oakwood Lodge Ln Unit 6, Piney Point, MD 20674
    17295 Oakwood Lodge Ln Unit 6, Piney Point, MD 20674
    17295 Oakwood Lodge Ln Unit 6, Piney Point, MD 20674
    /84

    $775,000

    $45K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,507 Sq Ft

    17295 Oakwood Lodge Ln Unit 6, Piney Point, MD 20674

    Enjoy effortless waterfront living in Southern Maryland from this premier end-unit condominium on Oakwood Lodge Lane in Piney Point, offering expansive views across the Potomac River to Virginia and a white sandy beach just steps from your door. Nestled within an exclusive 6-unit condominium community, this maintenance-free waterfront retreat offers over 3,500 square feet of beautifully designed

    Jennifer Goddard CENTURY 21 New Millennium

    17295 Oakwood Lodge Ln Unit 6, Piney Point, MD 20674
  • 42195 White Point Beach Rd, Leonardtown, MD 20650
    42195 White Point Beach Rd, Leonardtown, MD 20650
    42195 White Point Beach Rd, Leonardtown, MD 20650
    /57

    $699,900

    • 3 Beds
    • 2 Baths
    • 1,636 Sq Ft

    42195 White Point Beach Rd, Leonardtown, MD 20650

    Enjoy peaceful mornings in the 11’ x 26’ sunroom with wall of windows offering unobstructed views of the Potomac River from Piney Point, Virginia shoreline and west to St. Clements Island. End your day with majestic sunsets. A perfect waterfront escape but minutes to Leonardtown! Vintage 1920’s Cottage with all mechanicals, roof, windows, doors updated within the last 10 years but still

    Carl Franzen Franzen Realtors, Inc.

    42195 White Point Beach Rd, Leonardtown, MD 20650
  • 20894 Governors Mill Ct, Great Mills, MD 20634
    20894 Governors Mill Ct, Great Mills, MD 20634
    20894 Governors Mill Ct, Great Mills, MD 20634
    /46

    $469,000

    • 4 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    20894 Governors Mill Ct, Great Mills, MD 20634

    This spacious 4-bedroom, 3.5-bath home offers the perfect blend of comfort, functionality, and outdoor living. Move in ready, featuring hardwood flooring on the main level and new carpet in the family room and throughout the upper level. This home boasts a warm and inviting family room with a gas fireplace, ideal for gathering with family and friends.The generous owner's suite serves as a

    Janet Weaver RE/MAX One

    20894 Governors Mill Ct, 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

    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, large island and sun room overlooking the fenced backyard. All flow

    Jennifer Mullennix CENTURY 21 New Millennium

    19335 Greens Crossing Ct, 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 offers the

    Robin Cavallaro RE/MAX Realty Group

    17863 2nd St, Tall Timbers, MD 20690
  • 20824 Flour Mill Ct, Great Mills, MD 20634
    20824 Flour Mill Ct, Great Mills, MD 20634
    20824 Flour Mill Ct, Great Mills, MD 20634
    /7

    $559,000

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

    20824 Flour Mill Ct, Great Mills, MD 20634

    Brooke Matthews RE/MAX One

    20824 Flour Mill Ct, Great Mills, MD 20634
  • 44939 Shore Dr, Tall Timbers, MD 20690
    44939 Shore Dr, Tall Timbers, MD 20690
    44939 Shore Dr, Tall Timbers, MD 20690
    /59

    $495,000

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,108 Sq Ft

    44939 Shore Dr, Tall Timbers, MD 20690

    One level living with waterfront views are ready for you to move right in! This one story home includes 4 bedrooms and 2 full bathrooms. The home was renovated in 2016. As you enter the home, the open concept kitchen and main living area are perfect for hosting gatherings or entertaining. The kitchen has quartz counters, upgraded cabinets, stainless appliances, tile backsplash, upgraded lighting,

    Kelly Padgett Century 21 Redwood Realty

    44939 Shore Dr, Tall Timbers, MD 20690
  • 20750 Deer Wood Park Dr, Leonardtown, MD 20650
    20750 Deer Wood Park Dr, Leonardtown, MD 20650
    20750 Deer Wood Park Dr, Leonardtown, MD 20650
    /107

    $674,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 3,381 Sq Ft

    20750 Deer Wood Park Dr, Leonardtown, MD 20650

    Nestled in the serene community of Chestnut Hills of Leonardtown, this charming Colonial-style home offers a perfect blend of comfort and privacy. With 4 spacious bedrooms and 3.5 bathrooms, this residence spans an impressive 3,381 square feet, providing ample space for both relaxation and entertaining. Step inside to discover a warm and inviting interior. The open floor plan seamlessly connects

    Cynthia Ballard Century 21 Redwood Realty

    20750 Deer Wood Park Dr, Leonardtown, MD 20650
  • 20275 Jackson Rd, Callaway, MD 20620
    20275 Jackson Rd, Callaway, MD 20620
    20275 Jackson Rd, Callaway, MD 20620
    /7

    $250,000

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    20275 Jackson Rd, Callaway, MD 20620

    Opportunity awaits on this beautiful 3.05-acre parcel tucked away on a quiet paved road in the heart of Callaway. Whether you're looking for a renovation project, a homesite to build your dream home or an investment property, this property offers incredible potential with existing infrastructure already in place.The current mobile home is in need of significant renovation or removal, making

    Charlotte Long EXP Realty, LLC

    20275 Jackson Rd, Callaway, MD 20620
  • 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
    /13

    $2,250,000

    Coming Soon
    • 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
  • 44637 Bellview Ct, Tall Timbers, MD 20690
    44637 Bellview Ct, Tall Timbers, MD 20690
    /2

    $949,000

    $50K PRICE INCREASE Coming Soon
    • 4 Beds
    • 5 Baths
    • 3,455 Sq Ft

    44637 Bellview Ct, Tall Timbers, MD 20690

    Welcome to 44637 Bellview Court, an extraordinary waterfront retreat nestled within the highly coveted Landings at Tall Timbers community. Perfectly positioned to capture breathtaking 180-degree panoramic water views, this exceptional 4-bedroom, 5-bathroom residence offers an unparalleled blend of luxury, comfort, and the Potomac River lifestyle Designed to maximize its stunning waterfront

    Matthew Burgan Infinitas Realty Group

    44637 Bellview Ct, Tall Timbers, MD 20690
Maryland St Marys County

Homes for Sale with Garage in Chaptico, MD

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In Chaptico, there are currently 27 homes for sale with a garage. Meeting the needs of buyers seeking secure parking and extra storage, these homes offer various garage options. Whether it's a property featuring a practical two-car garage or a larger residence with a sought-after three-car garage, these homes provide the convenience and flexibility desired by many homeowners. Additionally, some properties come with detached garages, offering ample space while ensuring privacy. Explore the selection of homes for sale with a garage in Chaptico, MD and find the perfect place to call home.

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