5,217

Chaptico, MD Homes

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  • /75

    $599,000 Sold May 23, 2025

    • 3,646 Sq Ft
    • $164/SF
    • 1 Day On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2004

    46080 N Greens Rest Dr, Great Mills, MD 20634

    Spacious 4-Bedroom Home on 2 Acres – Close to PAX River with Water Access!Welcome to this well maintained 4-bedroom, 3.5-bath home situated on a level 2-acre lot, offering the perfect blend of space, privacy, and charm. The fully finished basement boasts an office and a versatile flex room that can easily serve as a home gym, 5th bedroom, or second home office—tailored to suit your needs.Enjoy

    Mary-Blake Summerlin CENTURY 21 New Millennium

    46080 N Greens Rest Dr, Great Mills, MD 20634
    • /32

      Est $528,522 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,681 Sq Ft

      20823 Flour Mill Ct, Great Mills, MD 20634

      20823 Flour Mill Ct, Great Mills, MD 20634
  • /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
  • /49

    $591,000 Sold May 22, 2025

    • 2,918 Sq Ft
    • $203/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1998

    44195 Jessica Ln, Leonardtown, MD 20650

    Stunning Cape Cod on 3+ Acres in Leonardtown!Welcome to this beautifully maintained 4-bedroom, 2.5-bath Colonial offering 2,918 sq ft of spacious living, nestled on 3.13 acres in the heart of Leonardtown. From the moment you arrive, you’ll feel the charm—this home stands out with its impressive curb appeal and serene setting.The wide, well-manicured driveway leads to a side-load garage, providing

    Mark Frisco CENTURY 21 New Millennium

    44195 Jessica Ln, Leonardtown, MD 20650
    • /27

      Est $287,924 Not Listed For Sale

      • Studio
      • 1,700 Sq Ft

      44938 Canvas Back Dr, Callaway, MD 20620

      44938 Canvas Back Dr, Callaway, MD 20620
  • /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
  • /22

    $300,000 Sold May 20, 2025

    • 1,160 Sq Ft
    • $259/SF
    • 3 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1953

    20483 White Point Rd, Leonardtown, MD 20650

    Welcome to 20483 White Point Road!Nestled on a beautiful 1-acre lot in Leonardtown, this charming 3-bedroom, 1-bath cottage-style rambler offers the perfect blend of comfort and character. Built in 1953, the home features a cozy, single-level layout that’s easy to maintain and full of potential. Enjoy peaceful country living surrounded by nature, all while being just a short drive to the heart of

    Theresa Shoptaw Redfin Corp

    20483 White Point Rd, Leonardtown, MD 20650
    • /22

      Est $417,807 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,388 Sq Ft

      42454 Wilderness Rd, Leonardtown, MD 20650

      42454 Wilderness Rd, Leonardtown, MD 20650
  • /2

    $40,000

    • Land
    • 0.18 Acre
    • $222,222 per Acre

    17852 3rd St, Tall Timbers, MD 20690

    Discover the perfect canvas for your dream home with this vacant residential lot, ideally situated just blocks away from the serene Saint Mary's River. Spanning approximately 8,000 square feet, this prime piece of real estate is located in the desirable St. George's Beach Subdivision, Lot 500-14, Block 18, as per Plat 59/55. Benefit from the convenience of an EDU from Metcom, ensuring public

    Samara Dinnius JPAR Real Estate Professionals

    17852 3rd St, Tall Timbers, MD 20690
  • /39

    $405,000 Sold May 20, 2025

    • 2,112 Sq Ft
    • $192/SF
    • 10 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1996

    17877 Saint Georges Park Rd, Tall Timbers, MD 20690

    Welcome to this inviting Cape Cod home, move-in ready and just a block from the scenic St. Mary's River, offering community fishing and boat access. Known for its picturesque tall pines, the area provides a serene backdrop to this 5-bedroom, 2.5-bathroom residence, which offers over two thousand square feet of living space on an 11,600 square foot fully fenced lot.The main section of the home

    Ekaterina Mikhaylova Compass

    17877 Saint Georges Park Rd, Tall Timbers, MD 20690
    • /35

      Est $405,187 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,288 Sq Ft

      17320 Potomac Sands Dr, Piney Point, MD 20674

      17320 Potomac Sands Dr, Piney Point, MD 20674
  • /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
  • /44

    $530,000 Sold May 19, 2025

    • 2,924 Sq Ft
    • $181/SF
    • 2 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2006

    20785 Brook Mill Ct, Great Mills, MD 20634

    Welcome to a home with lots of warmth and character. Simply stunning describes this wonderful quality-built Marrick home. This well-maintained property is in a desirable neighborhood on one third of an acre. This amazing home has lots to offer, presenting a designed layout with you in mind. Located in a cul-de-sac with an attached two car garage and a large driveway for additional vehicle

    Stewart Tellechea RE/MAX Realty Group

    20785 Brook Mill Ct, Great Mills, MD 20634
    • /54

      Est $590,145 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,538 Sq Ft

      20370 Chingville Rd, Leonardtown, MD 20650

      20370 Chingville Rd, Leonardtown, MD 20650
  • /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
  • /23

    $295,000 Sold May 14, 2025

    • 1,036 Sq Ft
    • $285/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1934

    20235 Big Oak Ln, Leonardtown, MD 20650

    Water access home with 3 bedrooms and 1 bath with laundry closet. Laminate flooring for easy of cleaning and pet friendly throughout much of the home. Level yard with big shed in back with 2 sides to store kayaks or other fun equipment for warm weather use. Patio in back and large clear side yard for volleyball or bocce ball or even corn hole. Make your plans now to come and see and make it your

    Jan Kleponis O'Brien Realty ERA Powered

    20235 Big Oak Ln, Leonardtown, MD 20650
    • /51

      Est $407,133 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,680 Sq Ft

      45193 Dory Ln, Piney Point, MD 20674

      45193 Dory Ln, Piney Point, MD 20674
  • /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
  • /63

    $724,900 Sold May 13, 2025

    • 2,635 Sq Ft
    • $275/SF
    • 9 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1998

    44634 Bellview Ct, Tall Timbers, MD 20690

    Welcome to 44634 Bellview Court, a stunning 4-bedroom, 2.5-bath waterfront home nestled in the highly desirable Landings at Piney Point community. This exceptional property offers breathtaking water views, a deeded boat slip, and access to top-tier amenities, making it the perfect retreat for water and outdoor enthusiasts alike.Brand New Roof on this amazing waterfront home. Step inside to find a

    Matthew Burgan Infinitas Realty Group

    44634 Bellview Ct, Tall Timbers, MD 20690
    • /69

      Est $717,038 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,448 Sq Ft

      46441 Porto Bello Ct, Drayden, MD 20630

      46441 Porto Bello Ct, 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
  • /12

    $135,000 Sold May 09, 2025

    • Land
    • 4.80 Acres
    • $28,125 per Acre
    • 76 Days On Market

    42500 Saint Margarets Dr, Leonardtown, MD 20650

    Expansive 4.8-Acre lot in highly sought after location.RECORDED PERC! Ready to build! Located just minutes outside the heart of Leonardtown, MD, this beautiful 4.8-acre lot offers a rare opportunity to bring your dream home to life on almost 5 private acres. Please be advised lot lines drawn on listing photo are not exact; just approximate and for visual purposes only.

    Kalee Kelly Infinitas Realty Group

    42500 Saint Margarets Dr, Leonardtown, MD 20650
    • /35

      Est $619,720 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,484 Sq Ft

      19380 Old Craney Creek Ln, Great Mills, MD 20634

      19380 Old Craney Creek Ln, Great Mills, MD 20634
  • /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
  • /97

    $600,000 Sold May 06, 2025

    • 3,605 Sq Ft
    • $166/SF
    • 253 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1955

    21500 Point Lookout Rd, Callaway, MD 20620

    All-Brick Rambler on a 6.11 acre lot along with a 9.58 acre separate lot with potential for additional homesite. This price includes both lots Welcome to 21500 Point Lookout Road, Leonardtown! This all-brick rambler sits on a large extensively landscaped lot and offers over 3,600 sq. ft. on the main level, plus 1,200 sq. ft. in the partially finished lower level. The home features 3 bedrooms

    Jennifer Goddard CENTURY 21 New Millennium

    21500 Point Lookout Rd, Callaway, MD 20620
    • /56

      Est $519,315 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,014 Sq Ft

      45674 Cecil Mill Ct, Great Mills, MD 20634

      45674 Cecil Mill Ct, Great Mills, MD 20634
  • /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
  • /6

    $74,200 Sold May 02, 2025

    • Land
    • 1.00 Acre
    • $74,200 per Acre
    • 13 Days On Market

    44968 Hewitt Rd, Callaway, MD 20620

    List price is Opening Bid at the Online auction to be conducted on Auctioneers website.- Auction ends Monday, March 10, 2025 at 11:00AM. 1± Acre of Land + Manufactured Home in "Calloway" of St. Mary's County zoned Rural Preservation District (RPD) - The regulations of Rural Preservation Districts are intended to foster agricultural, forestry, mineral resource extraction, and aquacultural uses and

    Carley Cooper Alex Cooper Auctioneers, Inc.

    44968 Hewitt Rd, Callaway, MD 20620
    • /45

      Est $565,541 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,716 Sq Ft

      20801 Brook Mill Ct, Great Mills, MD 20634

      20801 Brook Mill Ct, Great Mills, MD 20634
  • /68

    $794,905 Open Sat 12PM - 3PM

    • 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
  • /51

    $410,000 Sold May 01, 2025

    • 1,848 Sq Ft
    • $222/SF
    • 56 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1998

    17364 Potomac Sands Dr, Piney Point, MD 20674

    UPDATE: New Roof being installed, bring your best customers to see this gem!! Charming Cape Cod Retreat in Piney PointThis delightful 4 bedroom and 3 bath Cape Cod-style home offers the perfect blend of warmth and tranquility. A spacious patio, inviting deck, and cozy fire pit set the stage for peaceful mornings and starlit evenings, where the whispers of nature create a serene escape.Just a

    Kim Gosnell Redfin Corp

    17364 Potomac Sands Dr, Piney Point, MD 20674
    • /80

      Est $497,677 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,596 Sq Ft

      45686 Cecil Mill Ct, Great Mills, MD 20634

      45686 Cecil Mill Ct, Great Mills, MD 20634
  • /56

    $469,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,052 Sq Ft

    20898 Governors Mill Ct, Great Mills, MD 20634

    Come check out this great 4 bedroom, 3 1/2 bath home in the desirable Cecil's Mill development. The home features and updated kitchen, formal dining room, eat in kitchen, upstairs laundry, primary en suite, finished basement and great outdoor living space. There are many new features in the home- new HVAC in 2023, new water heater in 2024, and new sump with battery back up in 2022. The home is

    Karen Simmons RE/MAX Realty Group

    20898 Governors Mill Ct, Great Mills, MD 20634
  • /70

    $630,000 Sold Apr 25, 2025

    • 3,308 Sq Ft
    • $190/SF
    • 1 Day On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2014

    46180 Edgewood Ln, Great Mills, MD 20634

    Dive into Summer fun! Your personal oasis awaits at this cul-de-sac Colonial with inviting saltwater pool! Located in the desirable Crossing at Riverside Farm community, this gorgeous 4-bedroom, 3.5 bath home has something for everyone. Love to entertain? The formal living and dining rooms afford upscale dining and socializing, while the open-concept eat-in kitchen and family room lead out to

    Patrick Deighan CENTURY 21 New Millennium

    46180 Edgewood Ln, Great Mills, MD 20634
    • /68

      Est $580,851 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,504 Sq Ft

      20450 Piney Point Rd, Callaway, MD 20620

      20450 Piney Point Rd, Callaway, MD 20620
  • /29

    $289,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    20903 Jo Marie Way, Callaway, MD 20620

    Welcome home to this stunning 3 bedroom, 2.5 bath end unit townhome that has been thoughtfully updated throughout. Step inside to find brand-new LVP flooring throughout, fresh paint, and a recently upgraded master bath. The kitchen shines with new granite countertops, stainless steel appliances, and plenty of space for cooking. Other updates include a newer roof for peace of mind and much

    DJ Brady EXP Realty, LLC

    20903 Jo Marie Way, Callaway, MD 20620
  • /117

    $725,000 Sold Apr 17, 2025

    • 5,862 Sq Ft
    • $124/SF
    • 19 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1997

    20503 Deer Wood Park Dr, Leonardtown, MD 20650

    Discover this expansive, custom-designed brick Colonial situated on 2 pristine acres in the highly sought-after Chestnut Hills subdivision. Meticulously maintained, this stunning home offers a grand 2-story foyer and a soaring family room with a cozy propane fireplace, all complemented by 9-foot ceilings throughout the main level.The open-concept kitchen is a chef’s dream, featuring a center

    Tracey Summers CENTURY 21 New Millennium

    20503 Deer Wood Park Dr, Leonardtown, MD 20650
    • /64

      Est $485,978 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,243 Sq Ft

      42705 Redgate Farm Ln, Leonardtown, MD 20650

      42705 Redgate Farm Ln, Leonardtown, MD 20650
  • /40

    $364,900 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,300 Sq Ft

    21851 Peters Ct, California, MD 20619

    Nestled away on a quiet cul-de-sac in California, this 1.5 acre well maintained rambler can be yours to start your new adventure! New septic and well '21, new roof '23, hvac in Dec '24, hot water heater '25 and appliances less than 5 years old all taking the worry out of this purchase. The full bath was more recently renovated and fresh paint throughout most of the home provide a clean updated

    Robin Errington CENTURY 21 New Millennium

    21851 Peters Ct, California, MD 20619
  • /39

    $465,000 Sold Apr 14, 2025

    • 2,876 Sq Ft
    • $162/SF
    • 164 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1999

    20889 Ark Ct, Lexington Park, MD 20653

    This spacious home features 3 bedrooms and 3.5 bathrooms, providing ample space for comfortable living. The kitchen, complete with a center island, granite countertops and breakfast area, opens to the family room, making it perfect for entertaining. A separate living room and dining room provide additional space for hosting. The primary suite, with a vaulted ceiling, a spacious walk-in closets,

    Florentina Killian CENTURY 21 New Millennium

    20889 Ark Ct, Lexington Park, MD 20653

Showing Results 161 - 200, Page 5 of 18

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