5,236

Chaptico, MD Homes

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  • /18

    $589,000 Under Contract

    • 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
  • /18

    $2,800 per month

    • 4 Beds
    • 2.5 Baths
    • 2,434 Sq Ft
    • House for Rent

    20670 Bloombury Ln, Leonardtown, MD 20650

    Secluded home in Leonardtown area. Wrap around porch, garage, and plenty of area to spread out. 3 bedrooms on upper level one bedroom or office on main level. Unfinished basement and garage. Lots of outside room to roam and explore nature.

    Agent Photo

    Jimmy Hayden

    RE/MAX One

    (227) 234-0617

    20670 Bloombury Ln, Leonardtown, MD 20650
  • /22

    $300,000 Sold May 20, 2025

    20483 White Point Rd, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,160 Sq Ft
    • Built 1953

    Last Sold Summary

    • $259/SF
    • 3 Days On Market

    Current Estimated Value $308,745

    Last Listing Agent Theresa Shoptaw Keller Williams Realty

    20483 White Point Rd, Leonardtown, MD 20650
    • /44

      Est $580,136 Not Listed For Sale

      19435 S Greens Rest Dr, Great Mills, MD 20634

      • 3 Beds
      • 2.5 Baths
      • 3,086 Sq Ft
      • Built 2004
      19435 S Greens Rest Dr, Great Mills, MD 20634

      Last Sold Summary

      • 6% Above List Price
      • $177/SF
      • 0 Days On Market

      Last Sold Price $545,000

      Last Listing Agent Ron Lord Home Towne Real Estate

  • /3

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,128 Sq Ft

    18866 Russell Rd, Leonardtown, MD 20650

    ***Rare Waterfront Opportunity*** Welcome to 18866 Russell Rd, Valley Lee /Leonardtown, MD, a truly exceptional waterfront property offering a private, peaceful setting on a premium lot with stunning views of the water. Currently a 3-bedroom, 1.5-bath home, this property presents the perfect opportunity to reimagine, renovate, or rebuild into your dream waterfront retreat. Surrounded by natural

    Agent Photo

    Shelly Hibbert

    KW Metro Center

    (227) 997-7054

    18866 Russell Rd, Leonardtown, MD 20650
  • /11

    $2,300 total monthly price

    • 2 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Condo for Rent

    45146 Andover Estates Rd Unit 4, Valley Lee, MD 20692

    *Electric, water, sewer, and propane included in rent*Spacious 2 bed/2bath apartment available in beautiful Valley Lee, Unit 4. This multi-floor apartment is approx. 2000 square feet and has multiple custom wood cabinets built in. Includes living room, kitchen with dishwasher and eat-in space, 2 spacious bedrooms, 2 large bathrooms (one tub/shower combo and one shower only), cedar-lined

    45146 Andover Estates Rd Unit 4, Valley Lee, MD 20692
  • /37

    $485,000 Sold Jan 02, 2026

    17850 4th St, Tall Timbers, MD 20690

    • 4 Beds
    • 3.5 Baths
    • 2,495 Sq Ft
    • Built 2012

    Last Sold Summary

    • $194/SF
    • 102 Days On Market

    Current Estimated Value $486,549

    Last Listing Agent Charlotte Long EXP Realty, LLC

    17850 4th St, Tall Timbers, MD 20690
    • /36

      Est $633,638 Not Listed For Sale

      45597 Bethson St, California, MD 20619

      • 5 Beds
      • 3.5 Baths
      • 3,914 Sq Ft
      • Built 2017
      45597 Bethson St, California, MD 20619

      Last Sold Summary

      • 3% Above List Price
      • $157/SF
      • 15 Days On Market

      Last Sold Price $615,000

      Last Listing Agent Billy Rabbitt The Southside Group Real Estate

  • /13

    $130,000 Under Contract

    • Land
    • 5.09 Acres
    • $25,540 per Acre

    19921 Tower Hill Rd, Leonardtown, MD 20650

    Water access on this 5+ acre lot in sought after Leonardtown buildable, wooded, and perc'd lot. Build your dream home or purchase for access for kayaking. Covenants and Restrictions for neighborhood.

    Agent Photo

    Jimmy Hayden

    RE/MAX One

    (227) 888-6903

    19921 Tower Hill Rd, Leonardtown, MD 20650
  • /12

    $1,390 per month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    17476 Piney Point Rd Unit 5, Piney Point, MD 20674

    A MUST SEE! Charming efficiency apartment featuring one bedroom and one bathroom, complete with white kitchen cabinetry, granite countertops, and durable vinyl plank flooring throughout. Pets are welcome on a case-by-case basis with a $50 monthly pet rent. A $60 monthly utility fee includes water, sewer, trash, internet, parking, and lawn care for added convenience. The property is conveniently

    Florentina Killian CENTURY 21 New Millennium

    17476 Piney Point Rd Unit 5, Piney Point, MD 20674
  • /117

    $725,000 Sold Apr 17, 2025

    20503 Deer Wood Park Dr, Leonardtown, MD 20650

    • 5 Beds
    • 5 Baths
    • 5,862 Sq Ft
    • Built 1997

    Last Sold Summary

    • $124/SF
    • 19 Days On Market

    Current Estimated Value $756,396

    Last Listing Agent Tracey Summers CENTURY 21 New Millennium

    20503 Deer Wood Park Dr, Leonardtown, MD 20650
    • /3

      Est $1,274,015 Not Listed For Sale

      19710 Tower Hill Rd, Leonardtown, MD 20650

      • 5 Beds
      • 6.5 Baths
      • 5,690 Sq Ft
      • Built 1984
      19710 Tower Hill Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 4% Above List Price
      • $215/SF

      Last Sold Price $1,225,000

      Last Listing Agent Jennifer Goddard Century 21 New Millennium

  • /2

    $225,000

    • Land
    • 72.84 Acres
    • $3,089 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
  • /34

    $2,800 per month

    • 4 Beds
    • 2.5 Baths
    • 2,322 Sq Ft
    • House for Rent

    44886 Mallard Place, Callaway, MD 20620

    Spacious 4 bedroom, 2.5 bathroom home for rent in Callaway. Features hardwood floors throughout the main level, a large remodeled kitchen, and a spacious family room with a cozy wood-burning fireplace. Enjoy outdoor living with a large front porch and rear deck. Available April 1.

    Rayann Choporis CENTURY 21 New Millennium

    44886 Mallard Place, Callaway, MD 20620
  • /49

    $591,000 Sold May 22, 2025

    44195 Jessica Ln, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,918 Sq Ft
    • Built 1998

    Last Sold Summary

    • $203/SF
    • 5 Days On Market

    Current Estimated Value $596,465

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    44195 Jessica Ln, Leonardtown, MD 20650
    • /56

      Est $454,786 Not Listed For Sale

      20835 Flour Mill Ct, Great Mills, MD 20634

      • 5 Beds
      • 3.5 Baths
      • 3,140 Sq Ft
      • Built 2011
      20835 Flour Mill Ct, Great Mills, MD 20634

      Last Sold Summary

      • 3% Above List Price
      • $140/SF
      • 41 Days On Market

      Last Sold Price $440,000

      Last Listing Agent Theresa Shoptaw Keller Williams Realty

  • /50

    $1,850,000

    • 5 Beds
    • 6 Baths
    • 7,376 Sq Ft

    46369 Hattons Rest Ln, Lexington Park, MD 20653

    Welcome to The Retreat at Hattons Rest! A truly exceptional private waterfront estate set on a secluded 5.26-acre peninsula with an impressive 1,100 feet of pristine shoreline along the historic St. Mary's River. This magnificent 7,376-square-foot custom all-brick colonial home offers stunning water views from the kitchen and family room, where expansive windows perfectly capture the river's

    Agent Photo

    Gil Poudrier

    TTR Sotheby's International Realty

    (240) 655-8402

    46369 Hattons Rest Ln, Lexington Park, MD 20653
  • /36

    $2,600 per month

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft
    • House for Rent

    20503 Chestnut Ridge Dr, Leonardtown, MD 20650

    Nestled in the serene enclave of Chestnut Ridge, this exquisite Cape Cod-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. With a generous 3.04-acre lot, this home provides ample space for relaxation and outdoor enjoyment, all while maintaining a sense of privacy and tranquility. Freshly Painted and New Carpet in the Bedrooms. Step

    Jay Camp Coldwell Banker Premier

    20503 Chestnut Ridge Dr, Leonardtown, MD 20650
  • /58

    $549,900 Sold Apr 04, 2025

    46025 N Greens Rest Dr, Great Mills, MD 20634

    • 4 Beds
    • 3.5 Baths
    • 2,891 Sq Ft
    • Built 2000

    Last Sold Summary

    • $190/SF
    • 39 Days On Market

    Current Estimated Value $557,169

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    46025 N Greens Rest Dr, Great Mills, MD 20634
    • /36

      Est $654,718 Not Listed For Sale

      18914 Russell Rd, Valley Lee, MD 20692

      • 3 Beds
      • 2.5 Baths
      • 2,020 Sq Ft
      • Built 1999
      18914 Russell Rd, Valley Lee, MD 20692

      Last Sold Summary

      • 1% Below List Price
      • $327/SF
      • 66 Days On Market

      Last Sold Price $660,000

      Last Listing Agent Michelle Camaioni RE/MAX

  • /65

    $1,450,000 Under Contract

    • 5 Beds
    • 7 Baths
    • 7,376 Sq Ft

    20045 Tower Hill Rd, Leonardtown, MD 20650

    Set quietly within 12 picturesque acres overlooking a peaceful creek, Tower Hill Retreat offers an extraordinary opportunity to experience refined country living in a natural setting. This impressive estate features 5 bedrooms (with potential for a sixth) and 5 full and 2 half bathrooms in a thoughtfully designed and exceptionally versatile floor plan. Rich hardwood and tile flooring extend

    Barbara Stellway KW Metro Center

    20045 Tower Hill Rd, Leonardtown, MD 20650
  • /28

    $3,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,589 Sq Ft
    • House for Rent

    45325 Morgan Point Ln, Piney Point, MD 20674

    Enjoy a partial water view and your own private in-ground pool with a spacious patio surround—ideal for outdoor entertaining or relaxing in style. The main level features a luxurious primary suite, along with an open-concept layout that seamlessly connects the kitchen, dining area, and family room. You'll love the high ceilings, luxury vinyl plank (LVP) flooring throughout, granite countertops,

    Rayann Choporis CENTURY 21 New Millennium

    45325 Morgan Point Ln, Piney Point, MD 20674
  • /74

    $475,000 Sold Jul 15, 2025

    43985 Main Way Rd, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Built 1973

    Last Sold Summary

    • $198/SF
    • 1 Day On Market

    Current Estimated Value $483,898

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    43985 Main Way Rd, Leonardtown, MD 20650
    • /25

      Est $619,248 Not Listed For Sale

      21306 Fox Wood Ln, California, MD 20619

      • 5 Beds
      • 3.5 Baths
      • 3,673 Sq Ft
      • Built 2018
      21306 Fox Wood Ln, California, MD 20619

      Last Sold Summary

      • 10% Above List Price
      • $154/SF
      • 86 Days On Market

      Last Sold Price $565,000

      Last Listing Agent Jonathan Minerick Homecoin.com

  • /20

    $32,900

    • Land
    • 0.27 Acre
    • $121,852 per Acre

    0 Third St, Piney Point, MD 20690

    Looking for the perfect spot to build your dream home? This is a 0.27-acre (12,000 sq ft) lot in Tall Timbers, MD. Property is a buy-and-hold opportunity until sewer might become available with the Lighthouse development down the road. Enjoy the coastal charm, nestled in a quiet, near-the-water community, only minutes away from Piney Point Lighthouse & Beach and St. George Island Beach. The much

    Krista Depenthal Lands2Love

    0 Third St, Piney Point, MD 20690
  • /37

    $2,300 per month

    • 3 Beds
    • 1.5 Baths
    • 1,583 Sq Ft
    • House for Rent

    18937 McKays Cove Ln, Leonardtown, MD 20650

    Welcome to this charming water-access rambler! This inviting 3-bedroom, 1.5-bath home offers comfortable single-level living in a peaceful coastal setting.Inside, you’ll find an updated kitchen featuring granite countertops, stainless steel appliances, and ample cabinet space, perfect for everyday living and entertaining. The functional open floor plan provides bright living areas, well-sized

    Erika Yowell EXP Realty, LLC

    18937 McKays Cove Ln, Leonardtown, MD 20650
  • /34

    $470,000 Sold Feb 20, 2026

    20932 Sawgrass Dr, Lexington Park, MD 20653

    • 4 Beds
    • 3.5 Baths
    • 3,490 Sq Ft
    • Built 2003

    Last Sold Summary

    • $135/SF
    • 91 Days On Market

    Current Estimated Value $472,036

    Last Listing Agent James Barnes Home Towne Real Estate

    20932 Sawgrass Dr, Lexington Park, MD 20653
    • /62

      Est $568,448 Not Listed For Sale

      21311 Fox Wood Ln, California, MD 20619

      • 6 Beds
      • 4 Baths
      • 3,926 Sq Ft
      • Built 2018
      21311 Fox Wood Ln, California, MD 20619

      Last Sold Summary

      • 1% Below List Price
      • $146/SF
      • 9 Days On Market

      Last Sold Price $575,000

      Last Listing Agent Trish Brow EXP Realty, LLC

  • /87

    $1,110,000 Pending

    • 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
  • /90

    $575,000 Sold Mar 05, 2026

    21060 Woodmere Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,075 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Above List Price
    • $187/SF
    • 18 Days On Market

    Current Estimated Value $567,820

    Last Listing Agent Sharon Cox CENTURY 21 New Millennium

    21060 Woodmere Dr, Leonardtown, MD 20650
    • /70

      Est $597,694 Not Listed For Sale

      45673 Tennyhill St, California, MD 20619

      • 6 Beds
      • 4 Baths
      • 3,778 Sq Ft
      • Built 2019
      45673 Tennyhill St, California, MD 20619

      Last Sold Summary

      • 9% Above List Price
      • $146/SF
      • 11 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Val Perez Century 21 New Millennium

  • /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
  • /63

    $724,900 Sold May 13, 2025

    44634 Bellview Ct, Tall Timbers, MD 20690

    • 4 Beds
    • 2.5 Baths
    • 2,635 Sq Ft
    • Built 1998

    Last Sold Summary

    • $275/SF
    • 9 Days On Market

    Current Estimated Value $738,432

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    44634 Bellview Ct, Tall Timbers, MD 20690
    • /32

      Not Listed For Sale

      45780 Calla Ln, Great Mills, MD 20634

      • 4 Beds
      • 3 Baths
      • 2,368 Sq Ft
      • Built 2007
      45780 Calla Ln, Great Mills, MD 20634

      Last Sold Summary

      • $160/SF
      • 11 Days On Market

      Last Sold Price $380,000

      Last Listing Agent George Zarecki Coldwell Banker Premier

  • /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
  • /59

    $600,000 Sold Oct 01, 2025

    43571 Bayberry Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,946 Sq Ft
    • Built 1993

    Last Sold Summary

    • $204/SF
    • 22 Days On Market

    Current Estimated Value $615,299

    Last Listing Agent Jenny Norris EXP Realty, LLC

    43571 Bayberry Ct, Leonardtown, MD 20650
    • /38

      Est $345,473 Not Listed For Sale

      45723 Bethfield Way, California, MD 20619

      • 3 Beds
      • 3.5 Baths
      • 2,036 Sq Ft
      • Built 2018
      45723 Bethfield Way, California, MD 20619

      Last Sold Summary

      • 1% Below List Price
      • $171/SF

      Last Sold Price $348,000

      Last Listing Agent Livia Brow Remax 100

  • /7

    $772,000 Under Contract

    • 4 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    44798 Medleys Neck Rd, Leonardtown, MD 20650

    Other lots in the area, call us to discussTBB - Custom Home - Many other floor plans and locations - call to discuss

    Marie Jozwik RE/MAX Realty Group

    44798 Medleys Neck Rd, Leonardtown, MD 20650
  • /4

    $249,500 Sold Oct 27, 2025

    20861 Harlequin Ln, Callaway, MD 20620

    • 2 Beds
    • 2.5 Baths
    • 1,693 Sq Ft
    • Built 1988

    Last Sold Summary

    • $147/SF
    • 0 Days On Market

    Current Estimated Value $254,226

    Last Listing Agent Cathy Rose RE/MAX One

    20861 Harlequin Ln, Callaway, MD 20620
    • /43

      Est $399,584 Not Listed For Sale

      20875 Autumn Mill Ct, Great Mills, MD 20634

      • 4 Beds
      • 3 Baths
      • 2,008 Sq Ft
      • Built 2011
      20875 Autumn Mill Ct, Great Mills, MD 20634

      Last Sold Summary

      • 3% Below List Price
      • $204/SF
      • 3 Days On Market

      Last Sold Price $410,000

      Last Listing Agent Theresa Shoptaw Keller Williams Realty

Showing Results 1 - 40, Page 1 of 18

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