35

Chaptico, MD Homes for Sale with Acreage

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  • /4

    $549,900 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,924 Sq Ft

    21481 Indian Bridge Rd, California, MD 20619

    No HOA here. 1 acre home that backs to trees. Large deck off the back of the house with private setting. The home has been extremely well kept. Almost 3000 sq ft of living area with 4 bedrooms, 2.5 baths, and large 2 car garage. Propane fireplace insert. Paved driveway with ample parking and turn around area. Extra RV outlet from garage. These types of gems are hard to find so act quickly.

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (240) 684-8235

    21481 Indian Bridge Rd, California, MD 20619
  • /43

    $687,900

    • 5 Beds
    • 3 Baths
    • 3,500 Sq Ft

    20620 Laurel Ct, Leonardtown, MD 20650

    Move Right In and Start Living the Leonardtown Lifestyle!Welcome to 20620 Laurel Court — where modern luxury meets small town charm on nearly 5 private acres in sought-after Leonardtown, Maryland. Nestled in a peaceful cul-de-sac, this thoughtfully reimagined home offers over 3,000 sq ft of exceptional living space with 5 bedrooms and 3 full baths — including a convenient main level bedroom and

    Amy Gallo RE/MAX One

    20620 Laurel Ct, Leonardtown, MD 20650
  • /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
  • /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
  • /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
  • /41

    $540,000

    • 4 Beds
    • 2.5 Baths
    • 2,356 Sq Ft

    20955 Aster Dr, Callaway, MD 20620

    Well maintained by the original owners, this beautiful home sits on a private, 2-acre lot. Recent updates include a roof (8 years old), Heat pump & AC coil (2020), and a hot water heater (2025). The interior has been freshly painted, and new carpet on the main level. Enjoy outdoor living on the maintenance-free deck, replaced in 2012, or relax on the charming front porch. The family room features

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    20955 Aster Dr, Callaway, MD 20620
  • /91

    $599,999

    • 4 Beds
    • 3 Baths
    • 3,502 Sq Ft

    21946 Short Bow Ct, California, MD 20619

    Classic Single-Story Elegance on Quiet Cul-de-Sac | Near State Park, NAS Pax River & SolomonsWelcome to this timeless single-story residence, gracefully nestled at the end of a quiet cul-de-sac. Located just minutes from the natural beauty of a nearby state park offering scenic trails and a tranquil lake, this home also enjoys convenient access to NAS Patuxent River (less than 10 miles), a

    John Gatton CENTURY 21 New Millennium

    21946 Short Bow Ct, California, MD 20619
  • /123

    $2,100,000

    • 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 moment

    Natalya Ford EXP Realty, LLC

    46369 Hattons Rest Ln, Lexington Park, MD 20653
  • /25

    $1,125,000

    • Studio
    • 5,760 Sq Ft

    19645 Point Lookout Rd, Lexington Park, MD 20653

    Investment Opportunity in the Heart of Lexington Park!Don’t miss this rare opportunity to own a fully leased, cash-flowing quadplex just minutes from Pax River Naval Air Station, shopping, dining, and major employers. Generating over $7,700/month in rental income, this well-maintained asset offers strong cash flow and long-term upside.Each unit features 3 bedrooms, 2.5 baths, in-unit

    Haris Javaid O'Brien Realty ERA Powered

    19645 Point Lookout Rd, Lexington Park, MD 20653
  • /4

    $110,000

    • Land
    • 1.72 Acres
    • $63,953 per Acre

    19400 Brandon Way, Great Mills, MD 20634

    Last lot available in this very desirable neighborhood. Perc was performed last year in 2023 and passed. Build your dream home. 1.72 acres of land waiting for you. Nice location close to everything yet private. Got questions please ask.

    Melanie Montague EXP Realty, LLC

    19400 Brandon Way, Great Mills, MD 20634
  • /7

    $140,000

    • Land
    • 4.24 Acres
    • $33,019 per Acre

    Lot 28- 19285 Vanderhoof Ln, Valley Lee, MD 20692

    Lot 28 containing 4.239 private acres. If you're looking for privacy, come and build your dream home here in Valley Lee. Conveniently located yet still private. Approved perc and recorded plat is available in the documents. Contact me today for more details about this private homesite.

    Janet Weaver RE/MAX One

    Lot 28- 19285 Vanderhoof Ln, Valley Lee, MD 20692
  • /9

    $125,000

    • Land
    • 2.58 Acres
    • $48,450 per Acre

    Lot 27 Vanderhoof Ln, Valley Lee, MD 20692

    Lot 27 containing 2.58 private acres. If you're looking for privacy, come and build your dream home here in Valley Lee. Conveniently located yet still private. Approved perc and recorded plat is available in the documents. Contact me today for more details about this private homesite.

    Janet Weaver RE/MAX One

    Lot 27 Vanderhoof Ln, Valley Lee, MD 20692
  • /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
  • /13

    $315,000

    • 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 single-family ranch-style home features 3 bedrooms and 1 bathroom. Built in 1961, it offers approximately 1,026 square feet of living space and is

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, 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 island

    David DeSantis TTR Sotheby's International Realty

    46502 Glen Mary Farm Rd, Park Hall, MD 20667
  • /4

    $129,000

    • Land
    • 3.31 Acres
    • $38,973 per Acre

    19241 Pristine Way Ct, Drayden, MD 20630

    **THREE PERC SITES RECORDED***Discover the Perfect Setting for Your Dream Home!This beautiful, 3.31-acre buildable lot offers the peace and serenity you've been searching for, tucked away in the quiet community of Drayden. With **three perc sites recorded**, you’re ready to bring your vision to life and construct your dream home in this tranquil setting.Located just 10.5 miles

    Jessica Raley CENTURY 21 New Millennium

    19241 Pristine Way Ct, Drayden, MD 20630
  • /4

    $169,000

    • Land
    • 3.80 Acres
    • $44,474 per Acre

    46490 Frogs Marsh Rd, Drayden, MD 20630

    **THREE PERC SITES RECORDED**Discover the Perfect Setting for Your Dream Home!This beautiful, 3.80-acre buildable lot offers the peace and serenity you've been searching for, tucked away in the quiet community of Drayden. With **three perc sites recorded**, you’re ready to bring your vision to life and construct your dream home in this tranquil setting.Located just 10.5 miles from

    Jessica Raley CENTURY 21 New Millennium

    46490 Frogs Marsh Rd, Drayden, MD 20630
  • /4

    $129,000

    • Land
    • 2.53 Acres
    • $50,988 per Acre

    46530 Frogs Marsh Rd, Drayden, MD 20630

    **THREE PERC SITES RECORDED**Discover the Perfect Setting for Your Dream Home!This beautiful, 2.53-acre buildable lot offers the peace and serenity you've been searching for, tucked away in the quiet community of Drayden. With **three perc sites recorded**, you’re ready to bring your vision to life and construct your dream home in this tranquil setting.Located just 10.5 miles from the

    Jessica Raley CENTURY 21 New Millennium

    46530 Frogs Marsh Rd, Drayden, MD 20630
  • /3

    $59,000

    • Land
    • 3.57 Acres
    • $16,527 per Acre

    0 Piney Point Rd, Valley Lee, MD

    DISCOVER THIS 3.57 ACRE LOT AVAILABLE IN SOUGHT AFTER LEE VALLEY COMMUNITY WITHIN SAINT MARY'S COUNTY. ZONING RPD. DRIVE BY TODAY TO DETERMINE FOR YOURSELF HOW IT CAN WORK FOR YOUR NEEDS! OWNER FINANCING AVAILABLE.

    Jennifer Drennan Taylor Properties

    0 Piney Point Rd, Valley Lee, MD
  • /2

    $86,900

    • Land
    • 1.68 Acres
    • $51,726 per Acre

    22020 Victorian Dr, California, MD 20619

    Build you own home on this 1.677 acre lot in a great location!! No HOA in this community. The property has been perced and it's ready for your plans. Plat is available showing the perc location.

    Dawn Wood O'Brien Realty ERA Powered

    22020 Victorian Dr, California, MD 20619
  • /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
  • /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
  • /2

    $99,999

    • 3 Beds
    • 1 Bath
    • 924 Sq Ft

    44646 Medleys Neck Rd, Leonardtown, MD 20650

    Presenting an opportunity for creative redevelopment: a level lot equipped with a septic system and a driveway easement, along with a trailer that has microbiological growth. The property will require the removal of the existing trailer, with the option to proceed with new construction or secure a trailer replacement. Qualified buyers looking to customize and reimagine the site are encouraged to

    Ron Lord Home Towne Real Estate

    44646 Medleys Neck Rd, Leonardtown, MD 20650
  • /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
  • /2

    $155,000

    • Land
    • 2.09 Acres
    • $74,163 per Acre

    Lot 5 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630

    Lot 5 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 5 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
  • /2

    $160,000

    • Land
    • 2.49 Acres
    • $64,257 per Acre

    Lot 4 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630

    Lot 4 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. Approved perc for septic, utilities to be installed underground, call with any questions.

    Charlotte Long EXP Realty, LLC

    Lot 4 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
  • /2

    $195,000

    • Land
    • 5 Acres
    • $36,044 per Acre

    Lot 1 Mt. Pleasant F Drayden Rd, Drayden, MD 20630

    Lot 1 of Mount Pleasant Farms Minor Subdivision off Drayden Road on Hebb Road. Build your dream home on this beautiful, private, flat 5.41 acre lot and enjoy the peaceful tranquility of nature and the beauty of Southern Maryland sunsets at their finest. Approved perc for septic, utilities to be installed underground, call with any questions.

    Charlotte Long EXP Realty, LLC

    Lot 1 Mt. Pleasant F Drayden Rd, Drayden, MD 20630
  • /45

    $615,900 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
  • /27

    $605,900 New Construction

    • 4 Beds
    • 2.5 Baths

    46210 Stasha Ct, Drayden, MD 20630

    *** To Be Built *** ONE ACRE Plus Wooded Level LOT *** The DEVONSHIRE II Model, Elevation III *** GARAGE ****FABULOUS KITCHEN w/ Island & GRANITE Counters *** Pantry *** STAINLESS appliances *** Open Concept ** 1st Floor FAMILY ROOM open to the Kitchen *** FLEX Room off Kitchen could be Separate DINING Rm or STUDY or ART Room ** 2ND Floor LAUNDRY ** full BASEMENT w/Rough in for a FULL BATH **

    Lisa Riggleman RE/MAX One

    46210 Stasha Ct, Drayden, MD 20630
  • /64

    $659,900 New Construction

    • 4 Beds
    • 2.5 Baths

    19163 N Porto Bello Dr, Drayden, MD 20630

    *** To Be Built *** ONE ACRE Plus Wooded Level LOT *** THE CANTERBURY II Model, Elevation II *** 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 ***

    Lisa Riggleman RE/MAX One

    19163 N Porto Bello Dr, Drayden, MD 20630
  • /68

    $633,000 Open Fri 4PM - 6PM

    • 4 Beds
    • 3.5 Baths
    • 2,953 Sq Ft

    19201 Nelson Ct, Valley Lee, MD 20692

    Tucked away on over 3 acres at the end of a quiet cul-de-sac, this beautifully maintained 4-bedroom, 3.5-bathroom home is a true retreat, offering total privacy, serene views, and the feeling of being immersed in nature, all while just minutes from everything.Situated on a conservation lot with no neighbors in sight, the home sits among mature trees and lush greenery, perfect for anyone craving

    Melissa Rodriguez RE/MAX One

    19201 Nelson Ct, Valley Lee, MD 20692
  • /5

    $515,000 Coming Soon

    • 5 Beds
    • 3 Baths
    • 3,672 Sq Ft

    19339 Saint Georges Church Rd, Valley Lee, MD 20692

    Coming Soon!Discover the perfect blend of space, comfort, and privacy in this expansive 5-bedroom, 3-full bath rancher nestled on 2 serene acres. Offering over 3,600 square feet of living space, this home provides room to spread out. You'll love the flexibility of the floor plan, with generous living areas, beautiful kitchen with ss appliances, spacious bedrooms, and abundant natural light

    Katherine Dean RE/MAX One

    19339 Saint Georges Church Rd, Valley Lee, MD 20692
  • /29

    $610,000 Coming Soon

    • 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, the

    Cynthia Crispell CENTURY 21 New Millennium

    20814 Deer Wood Park Dr, Leonardtown, MD 20650
  • /2

    $615,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 3,061 Sq Ft

    20591 Chestnut Ridge Dr, Leonardtown, MD 20650

    Welcome to this well-built colonial in the picturesque 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 serene acres, the home features a classic brick exterior, a welcoming front porch, and a spacious two-car garage. Inside on the main level, you'll find two

    Lauren Garner EXP Realty, LLC

    20591 Chestnut Ridge Dr, Leonardtown, MD 20650
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