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Chaptico, MD Homes for Sale with Acreage

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  • 19305 Greens Crossing Ct, Great Mills, MD 20634
    19305 Greens Crossing Ct, Great Mills, MD 20634
    19305 Greens Crossing Ct, Great Mills, MD 20634
    /3

    $725,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 4,588 Sq Ft

    19305 Greens Crossing Ct, Great Mills, MD 20634

    Experience luxury and comfort in this stunning 4-bedroom, 3.5-bath home built in 2015, offering exceptional space, elegant upgrades, and resort-style outdoor living in beautiful Saint Mary's County. From the moment you enter, you’ll love the beautiful hardwood flooring, open-concept layout, and fresh new paint throughout. The heart of the home is the oversized gourmet kitchen featuring a gas

    Heather Heath Deep Roots Real Estate

    19305 Greens Crossing Ct, Great Mills, MD 20634
  • 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
  • 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

    Welcome to Ms. Piney Point! 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 room area

    Shanita Kelley Samson Properties

    20098 Piney Point Rd, Callaway, MD 20620
  • 18832 Piney Point Rd, Valley Lee, MD 20692
    18832 Piney Point Rd, Valley Lee, MD 20692
    18832 Piney Point Rd, Valley Lee, MD 20692
    /7

    $79,900

    • Land
    • 3.57 Acres
    • $22,381 per Acre

    18832 Piney Point Rd, Valley Lee, MD 20692

    Welcome to 18832 Piney Point Road! This property spans 3.57 acres and includes two lots within one parcel. Build your dream home in the peaceful waterfront community of Piney Point, Maryland. This exceptional parcel offers a rare opportunity to create a custom residence surrounded by natural beauty, privacy, and coastal charm. Nestled near the Potomac River, the property provides a serene setting

    Jonathan Benya EXP Realty, LLC

    18832 Piney Point Rd, Valley Lee, MD 20692
  • 46195 Kayak Ct, Great Mills, MD 20634
    46195 Kayak Ct, Great Mills, MD 20634
    46195 Kayak Ct, Great Mills, MD 20634
    /75

    $629,000

    • 5 Beds
    • 3.5 Baths
    • 3,380 Sq Ft

    46195 Kayak Ct, Great Mills, MD 20634

    Built in 2019 and perfectly situated on a large, private lot, this stunning 5-bedroom home offers the ideal blend of modern finishes and peaceful living. A long driveway leads to an oversized garage and sets the tone for the privacy this home provides. Inside, you'll find a bright and open layout designed for both everday living and entertaining. The spacious kitchen is the heart of the home,

    Jesieryl Hartzer CENTURY 21 New Millennium

    46195 Kayak Ct, 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

    $500K PRICE DROP
    • 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
  • 46080 Usher Ln, Valley Lee, MD 20692
    46080 Usher Ln, Valley Lee, MD 20692
    46080 Usher Ln, Valley Lee, MD 20692
    /3

    $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
    • 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
  • 0 Whirlwind Rd, Leonardtown, MD 20650
    0 Whirlwind Rd, Leonardtown, MD 20650
    /2

    $435,000

    • Land
    • 23.44 Acres
    • $18,558 per Acre

    0 Whirlwind Rd, Leonardtown, MD 20650

    23 acres with ability to build at least two homes

    Samara Dinnius JPAR Real Estate Professionals

    0 Whirlwind 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

    $269,700

    $29K PRICE DROP
    • Land
    • 1.63 Acres
    • $165,460 per Acre

    46175 N Greens Rest Dr, Great Mills, MD 20634

    One of the few remaining pristine lots left in Riverside Farms! 1.63 acre lot with permits, approved site plan, grading, and foundation in for 4BR, 3-4 BA 3500+ sq. ft. custom rambler with basement. Handicap accessible! This desirable neighborhood offers a community park, ball fields, walking trails, picnic areas, and community pier.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
  • 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

    $10K PRICE DROP
    • 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
  • 45954 Burns Dr, Valley Lee, MD 20692
    45954 Burns Dr, Valley Lee, MD 20692
    45954 Burns Dr, Valley Lee, MD 20692
    /44

    $574,900

    $20K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,430 Sq Ft

    45954 Burns Dr, Valley Lee, MD 20692

    PRICE IMPROVEMENT and SATURDAY, MAY 30th OPEN HOUSE! Welcome to a rare blend of privacy, efficiency, flexibility, and everyday comfort in the heart of Southern Maryland. Nestled on a quiet cul-de-sac and situated on TWO separate lots totaling over 2.8 acres, this beautifully maintained property offers the space and freedom today’s buyers are searching for — all within minutes of shopping, dining,

    Belinda Taylor EXP Realty, LLC

    45954 Burns Dr, Valley Lee, MD 20692
  • 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 ac of fertile land with a mile-long view of the Potomac River’s white sand shoreline, 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
  • 44939 Shore Dr, Tall Timbers, MD 20690
    44939 Shore Dr, Tall Timbers, MD 20690
    44939 Shore Dr, Tall Timbers, MD 20690
    /59

    $505,000

    $10K 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
  • 43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    /10

    $190,000

    • Land
    • 5 Acres
    • $38,000 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
  • 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
  • 0 Greens Crossing Way, Great Mills, MD 20634
    0 Greens Crossing Way, Great Mills, MD 20634
    /2

    $210,000

    $65K PRICE DROP
    • Land
    • 72.84 Acres
    • $2,883 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.

    Jimmy Hayden RE/MAX One

    0 Greens Crossing Way, Great Mills, MD 20634
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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