46,895

St Marys County, MD Homes

Section Image
  • /94

    $680,000

    • 4 Beds
    • 2 Baths
    • 2,388 Sq Ft

    25375 Loveville Rd, Leonardtown, MD 20650

    Nestled on a generous 3.8-acre corner lot, this charming Cape Cod-style home, built in 2017, offers a perfect blend of comfort and timeless appeal. With its excellent condition and thoughtful design, this residence is ready to welcome you home. Step inside to discover a warm and inviting interior that features a traditional floor plan, ideal for everyday living and entertaining. The home offers

    Kandy Moore RMG Realty

    25375 Loveville Rd, Leonardtown, MD 20650
  • /29

    $435,000

    Sold Aug 10, 2026

    23609 Crosswinds Way, California, MD 20619

    • 4 Beds
    • 3.5 Baths
    • 2,452 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $177/SF
    • 119 Days On Market

    Current Estimated Value $434,178

    Last Listing Agent Boyd Grainger Pearson Smith Realty, LLC

    23609 Crosswinds Way, California, MD 20619
    • /42

      Est $637,412

      Not Listed For Sale

      23641 Belmar Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,236 Sq Ft
      • Built 2012
      23641 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Heather Foster RE/MAX One

  • /10

    $1,999,999

    $500K PRICE DROP Under Contract
    • 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
  • /26

    $465,000

    Sold May 14, 2026

    22480 Olde Hewitt Rd, Lexington Park, MD 20653

    • 4 Beds
    • 2.5 Baths
    • 3,260 Sq Ft
    • Built 2005

    Last Sold Summary

    • $143/SF
    • 4 Days On Market

    Current Estimated Value $466,165

    Last Listing Agent Ross Simone RE/MAX One

    22480 Olde Hewitt Rd, Lexington Park, MD 20653
    • /18

      Est $113,016

      Not Listed For Sale

      48595 Sea Side View Rd, Ridge, MD 20680

      48595 Sea Side View Rd, Ridge, MD 20680

      Last Sold Summary

      • 303 Days On Market

      Last Listing Agent Leonard Parrish Irene B Parrish Realty

  • /3

    $375,000

    Coming Soon Oct 1
    • 4 Beds
    • 4 Baths
    • 2,116 Sq Ft

    48383 Sunburst Dr, Lexington Park, MD 20653

    Bring your beach chairs and leave the long commute behind! Just 200 yards from the Chesapeake Bay and less than five minutes from Pax River Naval Air Station, this beautifully maintained four-bedroom, three-and-a-half-bath townhome puts beach walks, bike rides, and evenings on the deck right outside your door. Situated on a corner lot near the neighborhood beach and walking and biking trails,

    Sarah Mulford-Martin EXP Realty, LLC

    48383 Sunburst Dr, Lexington Park, MD 20653
  • /84

    $1,300,000

    Sold May 11, 2026

    44850 Joy Chapel Rd, Hollywood, MD 20636

    • 3 Beds
    • 3.5 Baths
    • 4,241 Sq Ft
    • Built 1973

    Last Sold Summary

    • 13% Below List Price
    • $307/SF
    • 38 Days On Market

    Current Estimated Value $1,349,185

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    44850 Joy Chapel Rd, Hollywood, MD 20636
    • /30

      Not Listed For Sale

      23254 Chestnut Oak Ct, California, MD 20619

      • 1 Bed
      • 1 Bath
      • 759 Sq Ft
      • Built 1988
      23254 Chestnut Oak Ct, California, MD 20619

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Andrew Shemeta CENTURY 21 New Millennium

  • /77

    $524,900

    $15K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    NEW PRICE — $524,900! If you’ve been waiting for the right opportunity to make your move to Breton Bay, this could be the one.There’s something special about living in Breton Bay. It’s the kind of neighborhood where you can come home at the end of the day, leave the traffic behind, and actually enjoy where you live. Tucked away on a quiet cul-de-sac with virtually no through traffic, this

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, Leonardtown, MD 20650
  • /2

    $460,000

    Sold Aug 14, 2026

    16114 Thomas Rd, Piney Point, MD 20674

    • 4 Beds
    • 2.5 Baths
    • 2,262 Sq Ft
    • Built 1994

    Last Sold Summary

    • 2% Above List Price
    • $203/SF

    Current Estimated Value $531,375

    Last Listing Agent Jenny Norris EXP Realty, LLC

    16114 Thomas Rd, Piney Point, MD 20674
    • /54

      Est $390,483

      Not Listed For Sale

      23170 Longview Blvd, Bushwood, MD 20618

      • 3 Beds
      • 2.5 Baths
      • 2,016 Sq Ft
      • Built 1977
      23170 Longview Blvd, Bushwood, MD 20618

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Amy Gallo RE/MAX One

  • /20

    $45,000

    • Land
    • 10,018 Sq Ft
    • $195,652 per Acre

    36685 Owens Dr, Maddox, MD 20621

    Build your forever home or have a second home here in this quiet community. The Seller is willing to pay for a boundary survey within reason. He has already gotten a quote. Neatly tucked away. Minutes walk to the private pier, boating and fishing. Beautiful views of the Wicomico River. Come see the possibilities.

    Myra Wallace Samson Properties

    36685 Owens Dr, Maddox, MD 20621
  • /12

    $580,000

    Sold Oct 24, 2025

    20411 Monte Carlo Ln, Lexington Park, MD 20653

    • 5 Beds
    • 3.5 Baths
    • 3,768 Sq Ft
    • Built 2001

    Last Sold Summary

    • $154/SF
    • 42 Days On Market

    Current Estimated Value $598,109

    Last Listing Agent Thomas Hennerty NetRealtyNow.com, LLC

    20411 Monte Carlo Ln, Lexington Park, MD 20653
    • /30

      Est $311,698

      Not Listed For Sale

      23520 F D R Blvd Unit 302, California, MD 20619

      • 2 Beds
      • 2 Baths
      • 1,470 Sq Ft
      • Built 2013
      23520 F D R Blvd Unit 302, California, MD 20619

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Anne Carter CENTURY 21 New Millennium

  • /58

    $499,990

    • 4 Beds
    • 3 Baths
    • 2,010 Sq Ft

    20846 Autumn Mill Ct, Great Mills, MD 20634

    Welcome to 20846 Autumn Mill Court! This inviting home features a welcoming brick and siding exterior, spacious living areas, and plenty of natural light throughout. The main level offers beautiful hardwood flooring, a cozy fireplace, and an open flow between the living and dining areas. The kitchen features ample cabinetry, stainless steel appliances, and a convenient layout for everyday living.

    James Archie Own Real Estate

    20846 Autumn Mill Ct, Great Mills, MD 20634
  • /2

    $400,000

    Sold Jun 15, 2026

    39944 Lady Baltimore Ave, Leonardtown, MD 20650

    • 5 Beds
    • 2.5 Baths
    • 2,169 Sq Ft
    • Built 1997

    Last Sold Summary

    • 1% Above List Price
    • $184/SF
    • 7 Days On Market

    Current Estimated Value $403,646

    Last Listing Agent Kimberly Hayes CENTURY 21 New Millennium

    39944 Lady Baltimore Ave, Leonardtown, MD 20650
    • /28

      Est $330,034

      Not Listed For Sale

      22458 Dark Star Way, Lexington Park, MD 20653

      • 3 Beds
      • 3.5 Baths
      • 2,180 Sq Ft
      • Built 2013
      22458 Dark Star Way, Lexington Park, MD 20653

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Natalya Ford RE/MAX One

  • /59

    $399,000

    $1K PRICE DROP Under Contract
    • 4 Beds
    • 3 Baths
    • 1,792 Sq Ft

    42205 Ridge Rd, Mechanicsville, MD 20659

    Welcome to 42205 Ridge Road in Mechanicsville, a move-in ready Colonial located in the established St. Mary's Beach community.Fully renovated in 2018, this 4 bedroom, 3 full bathroom home offers a comfortable and functional layout. The main level features a welcoming foyer, kitchen and dining area, breakfast nook, crown molding, and a full bathroom. Upstairs, you'll find all four

    Ashley Frazier Five Star Real Estate

    42205 Ridge Rd, Mechanicsville, MD 20659
  • /130

    $1,250,000

    Sold May 22, 2026

    49730 Schoolhouse Ln, Dameron, MD 20628

    • 5 Beds
    • 3 Baths
    • 4,476 Sq Ft
    • Built 2006

    Last Sold Summary

    • 9% Above List Price
    • $279/SF
    • 2 Days On Market

    Current Estimated Value $1,169,709

    Last Listing Agent Helen Mattingly Wernecke Berkshire Hathaway HomeServices PenFed Realty

    49730 Schoolhouse Ln, Dameron, MD 20628
    • /8

      Est $202,000

      Not Listed For Sale

      36641 Knotts Ln, Mechanicsville, MD 20659

      36641 Knotts Ln, Mechanicsville, MD 20659

      Last Sold Summary

      • 130 Days On Market

      Last Listing Agent adrian abramson The Southside Group Real Estate

  • /8

    $550,000

    • Land
    • 5.96 Acres
    • $92,282 per Acre

    0 Mechanicsville Rd Unit MDSM2020678, Mechanicsville, MD 20659

    ****looking for a spot for your new business . . . 5.96 Acres of Commercial property. This was perked in 2010 but is expired. The property has many possibilities. There was a feasibility study done in the past and is now expired. I will be obtaining this information and any other past information and providing it online in the document section. ****ASK ABOUT OWNER FINANCING Available with down

    Stella Barbour NOVA Brokers, LLC.

    0 Mechanicsville Rd Unit MDSM2020678, Mechanicsville, MD 20659
  • /43

    $342,000

    Sold Oct 08, 2025

    22703 Ventura Way, California, MD 20619

    • 3 Beds
    • 2.5 Baths
    • 2,476 Sq Ft
    • Built 2008

    Last Sold Summary

    • $138/SF
    • 53 Days On Market

    Current Estimated Value $349,993

    Last Listing Agent Connie Gunn CENTURY 21 New Millennium

    22703 Ventura Way, California, MD 20619
    • /63

      Est $399,354

      Not Listed For Sale

      23200 Longview Blvd, Bushwood, MD 20618

      • 3 Beds
      • 3 Baths
      • 2,215 Sq Ft
      • Built 2005
      23200 Longview Blvd, Bushwood, MD 20618

      Last Sold Summary

      • 102 Days On Market

      Last Listing Agent Alan Smith CENTURY 21 New Millennium

  • /2

    $20,000

    $5K PRICE DROP
    • Land
    • 18,730 Sq Ft
    • $46,512 per Acre

    23253 Maddox Rd, Bushwood, MD 20618

    Build your dream coastal retreat on this beautiful 0.43-acre vacant lot located at 23253 Maddox Road in the desirable, water-oriented community of Bushwood, MD.Positioned in scenic St. Mary’s County, this lot offers the perfect foundation for a custom single-family home or vacation getaway. The critical site prep legwork is already underway—the property is approved for 2 mound septic systems,

    Billy Rabbitt The Southside Group Real Estate

    23253 Maddox Rd, Bushwood, MD 20618
  • /71

    $524,900

    Sold Apr 28, 2026

    23321 Dianthus Way, California, MD 20619

    • 5 Beds
    • 3.5 Baths
    • 2,909 Sq Ft
    • Built 2008

    Last Sold Summary

    • $180/SF
    • 3 Days On Market

    Current Estimated Value $525,266

    Last Listing Agent Jessica Abad CENTURY 21 New Millennium

    23321 Dianthus Way, California, MD 20619
    • /71

      Est $1,140,108

      Not Listed For Sale

      49005 Harry James Rd, Ridge, MD 20680

      • 4 Beds
      • 3.5 Baths
      • 1,827 Sq Ft
      • Built 2017
      49005 Harry James Rd, Ridge, MD 20680

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

  • /2

    $350,000

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft

    25991 Sotterley Rd, Hollywood, MD 20636

    Opportunity awaits at **25991 Sotterley Road**! This 1987 rambler offers approximately 1,400 sq. ft. with 3 bedrooms, 1 bath and a full walk-out unfinished basement, all situated on **11 wooded and private acres**. Ready for a new owner with the vision to renovate and transform it into their own. Electric heat pump and plenty of room to expand. Conveniently located near historic Sotterley.

    Conor Loughran CENTURY 21 New Millennium

    25991 Sotterley Rd, Hollywood, MD 20636
  • /59

    $825,000

    Sold Jun 12, 2026

    23395 Esperanza Cir, Lexington Park, MD 20653

    • 5 Beds
    • 3 Baths
    • 2,483 Sq Ft
    • Built 1972

    Last Sold Summary

    • 8% Below List Price
    • $332/SF
    • 16 Days On Market

    Current Estimated Value $866,792

    Last Listing Agent Chris McNelis Berkshire Hathaway HomeServices PenFed Realty

    23395 Esperanza Cir, Lexington Park, MD 20653
    • /31

      Est $234,845

      Not Listed For Sale

      24385 Macarthur Dr, Maddox, MD 20621

      • 2 Beds
      • 2 Baths
      • 916 Sq Ft
      • Built 1954
      24385 Macarthur Dr, Maddox, MD 20621

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Frank McKnew RE/MAX Realty Group

  • /60

    $649,900

    • 4 Beds
    • 2.5 Baths
    • 3,314 Sq Ft

    22157 Monterey Place, Leonardtown, MD 20650

    Nestled in the charming sought after Clearfields community, this stunning Colonial blends modern luxury with everyday comfort. Set on a beautifully landscaped 1.22-acre lot, this 4-bedroom, 2.5-bathroom home provides ample space for both relaxation and entertaining.At the heart of the home is a chef's dream kitchen, featuring custom cabinetry, gorgeous quartz countertops, a designer

    Tracey Summers CENTURY 21 New Millennium

    22157 Monterey Place, Leonardtown, MD 20650
  • /19

    $217,000

    Sold Dec 31, 2025

    44759 Woodlake Ct Unit 726, California, MD 20619

    • 2 Beds
    • 1.5 Baths
    • 936 Sq Ft
    • Built 1984

    Last Sold Summary

    • 1% Below List Price
    • $232/SF
    • 128 Days On Market

    Current Estimated Value $214,383

    Last Listing Agent Mitchell Seifert RE/MAX One

    44759 Woodlake Ct Unit 726, California, MD 20619
    • /5

      Est $745,000

      Not Listed For Sale

      13957 Underwood Farms Way, Charlotte Hall, MD 20622

      • 3 Beds
      • 3.5 Baths
      • 2,616 Sq Ft
      • Built 2025
      13957 Underwood Farms Way, Charlotte Hall, MD 20622

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Kadie Gertz RE/MAX One

  • /60

    $300,000

    • 3 Beds
    • 1.5 Baths
    • 1,454 Sq Ft

    36672 Wilson Dr, Bushwood, MD 20618

    Discover nearly an acre in Longview Beach, a waterfront community along the Wicomico River. Set on four lots totaling approximately .92 acres, this well-maintained 3-bedroom, 1.5-bath home offers peaceful one-level living and flexibility as a full-time residence, second home, weekend retreat, or investment property.The interior includes a living room, dining room, kitchen, spacious family

    Angela Skipper Keller Williams Flagship

    36672 Wilson Dr, Bushwood, MD 20618
  • /2

    $150,000

    Sold Mar 18, 2026

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

    • Land
    • 2.09 Acres
    • $71,770 per Acre

    Last Sold Summary

    • 1,263 Days On Market

    Last Listing Agent Charlotte Long EXP Realty, LLC

    Lot 5 Mt Pleasant Fa Drayden Rd, Drayden, MD 20630
    • /10

      Not Listed For Sale

      20668 Abell Rd, Abell, MD 20606

      20668 Abell Rd, Abell, MD 20606

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Amy Scott OE Realty

  • /2

    $5,000

    • Land
    • 10,018 Sq Ft
    • $21,739 per Acre

    0 Lagoon Dr, Maddox, MD 20621

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/2/2026, 10:00 AM. Bidding ends 10/6/2026, 9:35 AM. The list price is the suggested opening bid. Deposit: $2,500.This lot of land is located in Chaptico, MD within St. Mary’s County. The property is in close proximity to Wicomico Shores Golf Course, Christ Episcopal Church,

    Adam Shpritz Ashland Auction Group LLC

    0 Lagoon Dr, Maddox, MD 20621
  • /51

    $950,000

    Sold Dec 12, 2025

    49850 Saint Jeromes Place, Dameron, MD 20628

    • 6 Beds
    • 5 Baths
    • 3,766 Sq Ft
    • Built 2013

    Last Sold Summary

    • $252/SF
    • 47 Days On Market

    Current Estimated Value $941,470

    Last Listing Agent Bradley Franzen/Retired Franzen Realtors, Inc.

    49850 Saint Jeromes Place, Dameron, MD 20628
    • /9

      Est $299,182

      Not Listed For Sale

      23240 Longview Blvd, Bushwood, MD 20618

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2007
      23240 Longview Blvd, Bushwood, MD 20618

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Chelsea Guy Keller Williams Flagship

  • /40

    $249,900

    • 2 Beds
    • 2.5 Baths
    • 1,588 Sq Ft

    20811 Harlequin Ln, Callaway, MD 20620

    *An already attractive sales price just got even better. The seller is offering a $7,500 credit toward the buyer’s closing costs at settlement.* Spacious townhome with plenty of room to make your own. The main level features an eat-in kitchen and a large living room that opens directly to the deck and private backyard. Upstairs, you’ll find two generously sized bedrooms, one with a private en

    Katy Galloway Century 21 Redwood Realty

    20811 Harlequin Ln, Callaway, MD 20620

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