22

Chaptico, MD Homes for Sale with Acreage

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  • 43641 Redmond Rd, Leonardtown, MD 20650
    43641 Redmond Rd, Leonardtown, MD 20650
    43641 Redmond Rd, Leonardtown, MD 20650
    /18

    $589,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 2,184 Sq Ft

    43641 Redmond Rd, Leonardtown, MD 20650

    This great 8+ acre property with scenic pasture views. Solid 4 bedroom rambler on full basement. So many possibilities.

    Agent Photo

    Jimmy Hayden

    RE/MAX One

    (227) 231-3115

    43641 Redmond Rd, Leonardtown, MD 20650
  • 0 Greens Crossing Way, Great Mills, MD 20634
    0 Greens Crossing Way, Great Mills, MD 20634
    /2

    $275,000

    • Land
    • 72.84 Acres
    • $3,775 per Acre

    0 Greens Crossing Way, Great Mills, MD 20634

    73.30 total acres consisting of 2 lots. All wooded. Great for hunting or exploring nature as it gets very close to the St. Mary's River. This is an Open Space parcel so no building permitted. Great price for a LOT of land.

    Agent Photo

    Jimmy Hayden

    RE/MAX One

    (240) 262-0566

    0 Greens Crossing Way, Great Mills, MD 20634
  • 42520 Riverwinds Dr, Leonardtown, MD 20650
    42520 Riverwinds Dr, Leonardtown, MD 20650
    42520 Riverwinds Dr, Leonardtown, MD 20650
    /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
  • 46118 Edgemore Way, Great Mills, MD 20634
    46118 Edgemore Way, Great Mills, MD 20634
    46118 Edgemore Way, Great Mills, MD 20634
    /87

    $1,110,000 Open Sun 10AM - 12PM

    • 5 Beds
    • 4 Baths
    • 3,912 Sq Ft

    46118 Edgemore Way, Great Mills, MD 20634

    Tucked behind the trees in the heart of Southern Maryland, this remarkable 63-acre homestead offers privacy, natural beauty, and endless possibilities with no HOA! The main 15-acre estate features a spacious 5-bedroom, 4-bath home with flex room in the basement, has a two-car garage and is surrounded by the additional 48 acres of wooded land. Enjoy miles of ATV and riding trails, multiple

    Laura Holley O'Brien Realty ERA Powered

    46118 Edgemore Way, Great Mills, MD 20634
  • 46080 Usher Ln, Valley Lee, MD 20692
    46080 Usher Ln, Valley Lee, MD 20692
    /2

    $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
  • 46234 Stasha Ct, Drayden, MD 20630
    46234 Stasha Ct, Drayden, MD 20630
    46234 Stasha Ct, Drayden, MD 20630
    /32

    $679,900 New Construction

    • 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

    • 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
  • 20959 Redgate Ln, Leonardtown, MD 20650
    20959 Redgate Ln, Leonardtown, MD 20650
    20959 Redgate Ln, Leonardtown, MD 20650
    /13

    $189,000

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

    20959 Redgate Ln, Leonardtown, MD 20650

    *Back on the market. 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

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
  • 19166 N Porto Bello Dr, Drayden, MD 20630
    19166 N Porto Bello Dr, Drayden, MD 20630
    19166 N Porto Bello Dr, Drayden, MD 20630
    /30

    $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
  • 18688 Hebb Rd, Valley Lee, MD 0
    18688 Hebb Rd, Valley Lee, MD 0
    18688 Hebb Rd, Valley Lee, MD 0
    /58

    $859,900 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,127 Sq Ft

    18688 Hebb Rd, Valley Lee, MD 0

    Are you searching for a custom home. Look no further! This stunning custom-built residence, to be constructed by the highly acclaimed Litz Custom Homes, is designed for modern living in a serene setting. Situated on a spacious 2.5-acre lot in Drayden, this exquisite property comes with no HOA, offering you the freedom to enjoy your space. The Jackson floor plan seamlessly blends the charm of a

    Michele Posey RE/MAX Realty Group

    18688 Hebb Rd, Valley Lee, MD 0
  • 19830 Fall Ct, Great Mills, MD 20634
    19830 Fall Ct, Great Mills, MD 20634
    19830 Fall Ct, Great Mills, MD 20634
    /47

    $374,900

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    19830 Fall Ct, Great Mills, MD 20634

    GREAT Starter Home with 2 Car Garage and no HOA. Split Bedroom Floorplan - Primary on one side and 2 other bedrooms on the other. Open kitchen area with granite countertops, center island, pantry, SS Appliances, Primary Bedroom with Walk In Closet and Large Shower in Primary Bath. Exterior features Front Porch, Paved Driveway, Deck and woods all around. Don't Wait on this one!!

    Donna Lacey CENTURY 21 New Millennium

    19830 Fall Ct, Great Mills, MD 20634
  • 45252 Happyland Rd, Valley Lee, MD 20692
    45252 Happyland Rd, Valley Lee, MD 20692
    45252 Happyland Rd, Valley Lee, MD 20692
    /5

    $150,000

    • Land
    • 1.75 Acres
    • $85,714 per Acre

    45252 Happyland Rd, Valley Lee, MD 20692

    1.75 cleared acres zoned commercial. The address of 45252 Happyland Rd was assigned afterCommercial Outparcel C had an approved Perc. St. Mary’s County zoning is Rural Commercial Limited(RCL). Find information on uses of an RCL lot online at St. Mary's County comprehensive zoning ordinance. Excerpt from ordinance (RCL Jul 24, 2007... By the enactment of County Commissioners Ordinance No.

    Lawrence Lessin Save 6, Incorporated

    45252 Happyland Rd, Valley Lee, MD 20692
  • 0 Piney Point Rd, Callaway, MD 20620
    0 Piney Point Rd, Callaway, MD 20620
    /2

    $85,000

    • Land
    • 1.5 Acres
    • $56,667 per Acre

    0 Piney Point Rd, Callaway, MD 20620

    Discover the perfect canvas for your dream home on this 1.5-acre parcel of land, nestled in a vibrant community that offers both tranquility and convenience. Imagine waking up each day surrounded by nature, with ample space to create your own private oasis while still being just moments away from local amenities. This prime piece of land is situated in an area known for its friendly atmosphere

    Jessica Raley CENTURY 21 New Millennium

    0 Piney Point Rd, Callaway, MD 20620
  • Lot 6 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
    Lot 6 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
    /2

    $160,000

    • Land
    • 2.37 Acres
    • $67,511 per Acre

    Lot 6 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630

    Lot 6 of Mount Pleasant Farms Minor Subdivision off Drayden Road on Hebb Road. Build your dream home on this beautiful, lot and enjoy the peaceful tranquility of nature and the beauty of Southern Maryland sunsets at their finest. Ap5proved perc for septic, utilities to be installed underground, call with any questions.

    Charlotte Long EXP Realty, LLC

    Lot 6 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
  • 19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    /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
  • Lot 2 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
    Lot 2 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
    /2

    $175,000

    • Land
    • 2.45 Acres
    • $71,429 per Acre

    Lot 2 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630

    Lot 2 of Mount Pleasant Farms Minor Subdivision off Drayden Road on Hebb Road. Build your dream home on this beautiful, private, partially wooded lot and enjoy the peaceful tranquility of nature and the beauty of Southern Maryland sunsets at their finest. This lot has mostly woods and slopes down in the back, perfect for a home with a walk out basement. Approved perc for septic, utilities to be

    Charlotte Long EXP Realty, LLC

    Lot 2 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
  • 43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    /10

    $205,000

    • Land
    • 5 Acres
    • $41,000 per Acre

    43488 Medleys Neck Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!Discover the potential of this beautiful parcel in the heart of Southern Maryland. Located on Medleys Neck Road in Leonardtown, this property offers the perfect opportunity to build your dream home or investment project in a highly desirable location. The lot features three active perc approvals, making it an attractive option for builders, developers, or anyone seeking

    Bill Oosterink CENTURY 21 New Millennium

    43488 Medleys Neck Rd, Leonardtown, MD 20650
  • 46175 N Greens Rest Dr, Great Mills, MD 20634
    46175 N Greens Rest Dr, Great Mills, MD 20634
    46175 N Greens Rest Dr, Great Mills, MD 20634
    /8

    $750,000 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 River

    Joe and Judi Limerick CENTURY 21 New Millennium

    46175 N Greens Rest Dr, Great Mills, MD 20634
  • 21117 Catnip Ct, Leonardtown, MD 20650
    21117 Catnip Ct, Leonardtown, MD 20650
    21117 Catnip Ct, Leonardtown, MD 20650
    /68

    $590,000

    • 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
  • 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
  • 19285 Vanderhoof Ln, Valley Lee, MD 20692
    19285 Vanderhoof Ln, Valley Lee, MD 20692
    19285 Vanderhoof Ln, Valley Lee, MD 20692
    /3

    $135,000

    • Land
    • 4.24 Acres
    • $31,840 per Acre

    19285 Vanderhoof Ln, Valley Lee, MD 20692

    Rare 4.239-acre wooded sanctuary with approved perc in Valley Lee, the perfect canvas for your dream retirement home or development opportunity. This pristine parcel combines natural serenity with practical build-ready advantages. Mature trees provide exceptional privacy and natural cooling, ideal for a one-level custom home designed for comfortable retirement living. The approved percolation

    Robert Gauger EXP Realty, LLC

    19285 Vanderhoof Ln, Valley Lee, MD 20692
  • 44545 Brewer Ln, Leonardtown, MD 20650
    44545 Brewer Ln, Leonardtown, MD 20650
    44545 Brewer Ln, Leonardtown, MD 20650
    /69

    $674,900

    • 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
Maryland St Marys County Chaptico

Homes for Sale with Acreage in Chaptico, MD

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In Chaptico, there are currently 22 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Chaptico, MD offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Chaptico and discover the potential and freedom that comes with owning your own piece of property.

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