15,718

Caroline County, MD Homes

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  • /2

    $30,000

    • Land
    • 23,522 Sq Ft
    • $55,556 per Acre

    26519 3 Bridges Rd, Federalsburg, MD 21632

    Previous building is a complete tear down. Do not enter the building. Half acre lot zoned R1, one property. Buyer must contact Caroline County for any more information. There could be a private community septic on the property. Seller will consider holding a 2 year note with $15,000 down payment.

    Charles Hajjar Smart Realty, LLC

    26519 3 Bridges Rd, Federalsburg, MD 21632
  • /43

    $315,000

    Sold Sep 15, 2025

    25266 Smith Landing Rd, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 1,256 Sq Ft
    • Built 1953

    Last Sold Summary

    • $251/SF
    • 2 Days On Market

    Last Listing Agent Megan Rosendale Rosendale Realty

    25266 Smith Landing Rd, Denton, MD 21629
    • /18

      Est $393,019

      Not Listed For Sale

      1308 Trice Meadows Cir, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,505 Sq Ft
      • Built 2007
      1308 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 264 Days On Market

  • /8

    $17,000

    • Land
    • 8,712 Sq Ft
    • $85,000 per Acre

    0 Brooklyn Ave, Federalsburg, MD 21632

    Opportunity awaits in Federalsburg! This residential lot offers the convenience of public water and sewer connections, making it a great option for your next build or investment project. Located close to local shops, dining, schools, and everyday amenities, this property provides both accessibility and potential. The lot next door is also available for sale, creating an opportunity to purchase

    Aubrey Campbell Keller Williams Realty Delmarva

    0 Brooklyn Ave, Federalsburg, MD 21632
  • /2

    $286,990

    Sold Sep 24, 2025

    114 Parkland Rd, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    Last Sold Summary

    • $197/SF
    • 9 Days On Market

    Last Listing Agent Justin Wood D.R. Horton Realty of Virginia, LLC

    114 Parkland Rd, Greensboro, MD 21639
    • /27

      Est $414,352

      Not Listed For Sale

      6 W Liberty St, Ridgely, MD 21660

      • 3 Beds
      • 3.5 Baths
      • 2,184 Sq Ft
      • Built 2005
      6 W Liberty St, Ridgely, MD 21660

      Last Sold Summary

      • 2 Days On Market

  • /20

    $265,790

    New Construction $3K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft

    132 Hobbs St, Greensboro, MD 21639

    **Red Tag Sales Event now through January 25, 2026! Was $268,490 Now: $265,790! Home must close on or before 3/31/2026.** Discover the Perry in Kinnamon Meadows, a 1,059 square foot open concept cottage-style ranch home, offering two bedrooms and two bathrooms at 132 Hobbs Street in Greensboro, MD. A welcoming front porch leads you into the spacious living room that seamlessly flows into the

    Justin Wood D.R. Horton Realty of Virginia, LLC

    132 Hobbs St, Greensboro, MD 21639
  • /52

    $320,000

    Sold Nov 19, 2025

    17635 Cool Spring Rd, Marydel, MD 21649

    • 3 Beds
    • 2 Baths
    • 1,782 Sq Ft
    • Built 1992

    Last Sold Summary

    • $180/SF
    • 18 Days On Market

    Last Listing Agent Daphne Reeve Keller Williams Flagship

    17635 Cool Spring Rd, Marydel, MD 21649
    • /25

      Est $352,059

      Not Listed For Sale

      24636 Williston Rd, Denton, MD 21629

      • 3 Beds
      • 1.5 Baths
      • 1,472 Sq Ft
      • Built 1959
      24636 Williston Rd, Denton, MD 21629

      Last Sold Summary

      • 320 Days On Market

  • /62

    $519,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,805 Sq Ft

    8047 Laurel Ln, Denton, MD 21629

    Welcome to 8047 Laurel Lane in Denton, Md. First time ever offered on the market! Tucked away on 1.4 private, wooded acres in Denton’s sought-after Forest Landing community, this custom-built 3BR/2BA home features a pristine inground pool, a brand-new roof, and water-privileged community access just minutes from the Tuckahoe Creek, leading into the Choptank River. Property Highlights:Move-In

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    8047 Laurel Ln, Denton, MD 21629
  • /19

    $300,000

    Sold Dec 23, 2025

    14 N Maple Ave, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Below List Price
    • $284/SF
    • 46 Days On Market

    Current Estimated Value $288,576

    Last Listing Agent Joshua Clark Clark & Co Realty, LLC

    14 N Maple Ave, Ridgely, MD 21660
    • /27

      Est $171,195

      Not Listed For Sale

      308 Park Ave, Federalsburg, MD 21632

      • 2 Beds
      • 2 Baths
      • 952 Sq Ft
      • Built 1904
      308 Park Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 36 Days On Market

  • /47

    $395,000

    • 4 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    502 Kathryn Ct, Denton, MD 21629

    Updated + Upgraded - Turn-key 4BR/2.5BA contemporary 2-story home on a culdesac lot backing to trees, near historic downtown Denton - a true gem of an Eastern Shore town, perchec on the banks of the Choptank River - but tucked away on a residential court. New flooring + paint throughout, new granite counters, new kitchen appliances, new fixtures. Wide open floorplan boasts tall ceilings, spacious

    Charlene Reaser EXP Realty, LLC

    502 Kathryn Ct, Denton, MD 21629
  • /30

    $390,000

    Sold Jul 21, 2025

    333 Morning Glory Dr, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,475 Sq Ft
    • Built 2021

    Last Sold Summary

    • $158/SF
    • 21 Days On Market

    Current Estimated Value $392,722

    Last Listing Agent Danny Martin Keller Williams Flagship

    333 Morning Glory Dr, Denton, MD 21629
    • /3

      Est $431,929

      Not Listed For Sale

      12141 Greensboro Rd, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1950
      12141 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 0 Days On Market

  • /37

    $309,900

    • 4 Beds
    • 3.5 Baths
    • 2,280 Sq Ft

    1624 Blue Heron Dr, Denton, MD 21629

    Move-in ready and thoughtfully updated—this is one you won’t want to miss. Step inside this newly renovated 2,200 sq. ft. townhome located in the heart of Denton, MD. Featuring four spacious bedrooms and 3.5 bathrooms, this home offers a perfect blend of comfort, functionality, and modern design. The entry level includes a versatile first-floor bedroom with a walk-in closet—ideal for guests, a

    Michelle DiDonato Island Realty, LLC

    1624 Blue Heron Dr, Denton, MD 21629
  • /34

    $280,000

    Sold Mar 30, 2026

    2451 Guard Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 2006

    Last Sold Summary

    • 12% Above List Price
    • $199/SF
    • 7 Days On Market

    Current Estimated Value $276,257

    Last Listing Agent Alicia Gannon Dulin Benson & Mangold, LLC

    2451 Guard Rd, Federalsburg, MD 21632
    • /22

      Est $260,081

      Not Listed For Sale

      350 Deep Shore Rd, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,350 Sq Ft
      • Built 1965
      350 Deep Shore Rd, Denton, MD 21629

      Last Sold Summary

      • 11 Days On Market

  • /2

    $155,000

    $34K PRICE DROP Under Contract
    • 3 Beds
    • 1 Bath
    • 1,015 Sq Ft

    208 W 2nd St, Ridgely, MD 21660

    Fixer up in town!!! New hot water 2025. More pictures coming. (Agent Owner)

    Dawn Williams Berkshire Hathaway Homeservice Homesale Realty

    208 W 2nd St, Ridgely, MD 21660
  • /33

    $320,000

    Sold Jul 07, 2025

    3880 Laurel Grove Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft
    • Built 1940

    Last Sold Summary

    • $293/SF
    • 4 Days On Market

    Current Estimated Value $322,740

    Last Listing Agent Barton Johnson/not int Marshy Hope Realty LLC

    3880 Laurel Grove Rd, Federalsburg, MD 21632
    • /27

      Est $269,874

      Not Listed For Sale

      319 Kerr Ave, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1975
      319 Kerr Ave, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

  • /28

    $669,000

    $131K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,880 Sq Ft

    1108 Camp Rd, Denton, MD 21629

    Price Reduction! Motivated Seller. Welcome to 1108 Camp Street, sits on over 14 acres of land where modern comfort meets elegant design through an extensive list of upgrades that enhance both functionality and style. This home features stunning stone work on both the front and back, framing the house in natural beauty and providing a warm welcome. The meticulously crafted stone walls create an

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    1108 Camp Rd, Denton, MD 21629
  • /48

    $460,000

    Sold Jul 22, 2025

    14462 Poplar St, Goldsboro, MD 21636

    • 3 Beds
    • 2.5 Baths
    • 2,131 Sq Ft
    • Built 2003

    Last Sold Summary

    • $216/SF
    • 5 Days On Market

    Current Estimated Value $472,216

    Last Listing Agent Peter Mellor Wright Real Estate

    14462 Poplar St, Goldsboro, MD 21636
    • /40

      Est $625,623

      Not Listed For Sale

      8291 Clearfield Rd, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 2,800 Sq Ft
      • Built 2005
      8291 Clearfield Rd, Denton, MD 21629

      Last Sold Summary

      • 14 Days On Market

  • /31

    $399,000

    $70K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 2,885 Sq Ft

    112 S 5th Ave, Denton, MD 21629

    Reduced, sellers are ready to move on! Homes like this is what they use for Christmas cards, large wrap around porch, entry foyer, detailed fireplaces, hard wood floors, and so much more. This is waiting for the right owner to continue the 126 years this home has stood. Everything in this home is in grand size. Large rooms, make this an easy home for a large family . The house current owners have

    Kat Thompson Benson & Mangold, LLC.

    112 S 5th Ave, Denton, MD 21629
  • /57

    $280,000

    Sold Nov 26, 2025

    122 Mill St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,104 Sq Ft
    • Built 2002

    Last Sold Summary

    • $254/SF
    • 48 Days On Market

    Current Estimated Value $271,068

    Last Listing Agent Carolyn Buchleitner Berkshire Hathaway HomeServices PenFed Realty

    122 Mill St, Greensboro, MD 21639
    • /30

      Est $370,186

      Not Listed For Sale

      110 Sharp Rd, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,851 Sq Ft
      • Built 1968
      110 Sharp Rd, Denton, MD 21629

      Last Sold Summary

      • 4 Days On Market

  • /139

    $750,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,432 Sq Ft

    12136 Holly Rd, Ridgely, MD 21660

    PLEASE NOTE THIS IS A RELOCATION SALE SO OFFERS MUST BE WRITTEN PER THE DISCLOSURE DOCUMENTS UPLOADED WITH ALLEGIANCE GOVERNMENT RELOCATION AS THE SELLER. CONTACT LISTING TEAM MEMBER (WHITNEY) WITH ANY QUESTIONS. Set in a peaceful pastural setting , this impeccably maintained horse farm offers the perfect blend of country living and thoughtfully designed equestrian amenities. The beautifully

    Donna Harrington Coldwell Banker Realty

    12136 Holly Rd, Ridgely, MD 21660
  • /24

    $212,000

    Sold Jul 09, 2025

    524 Denton Rd, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1920

    Last Sold Summary

    • $245/SF
    • 9 Days On Market

    Current Estimated Value $211,330

    Last Listing Agent Nora Turner Long & Foster Real Estate, Inc.

    524 Denton Rd, Federalsburg, MD 21632
    • /14

      Est $281,541

      Not Listed For Sale

      27701 Burrsville Rd, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,092 Sq Ft
      • Built 1980
      27701 Burrsville Rd, Denton, MD 21629

      Last Sold Summary

      • 15 Days On Market

  • /35

    $379,900

    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft

    22403 Marsh Creek Rd, Preston, MD 21655

    Custom Brick rancher, close to town on large lot. Open floor plan, spacious kitchen, stainless steel appliances, large island. 3 bedrooms, 2 baths, sunroom overlooking yard. Upgrades include new windows, CAC, new roof new electric service and plumbing New Septic and Well, Closing help will be considered

    Barbara Nichols Results Realty Inc.

    22403 Marsh Creek Rd, Preston, MD 21655
  • /71

    $940,000

    Sold Nov 17, 2025

    8816 Dorothy Ln, Denton, MD 21629

    • 4 Beds
    • 3.5 Baths
    • 4,092 Sq Ft
    • Built 1989

    Last Sold Summary

    • $230/SF
    • 166 Days On Market

    Current Estimated Value $935,602

    Last Listing Agent Dustin Parker The Parker Group

    8816 Dorothy Ln, Denton, MD 21629
    • /19

      Est $206,291

      Not Listed For Sale

      312 Buena Vista Ave, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,308 Sq Ft
      • Built 1900
      312 Buena Vista Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 2 Days On Market

  • /16

    $323,000

    $17K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,892 Sq Ft

    11502 Greensboro Rd, Greensboro, MD 21639

    This is an auction property.This property has been placed in an upcoming event. Please reach out to the listing agent on where the bids are to be submitted. Please submit any pre-auction offer received through the property details page, please reach out to the listing agent. Any post-auction offers will need to be submitted directly to the listing agent. Response within 3 business days. All

    Pamela Geib Long & Foster Real Estate, Inc.

    11502 Greensboro Rd, Greensboro, MD 21639
  • /25

    $235,000

    Sold Oct 30, 2025

    113 Boyce Mill Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 2007

    Last Sold Summary

    • $196/SF
    • 18 Days On Market

    Current Estimated Value $244,583

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    113 Boyce Mill Rd, Greensboro, MD 21639
    • /95

      Est $440,662

      Not Listed For Sale

      25766 Beauchamp Branch Rd, Denton, MD 21629

      • 3 Beds
      • 1.5 Baths
      • 1,932 Sq Ft
      • Built 1915
      25766 Beauchamp Branch Rd, Denton, MD 21629

      Last Sold Summary

      • 4 Days On Market

  • /123

    $699,000

    • 3 Beds
    • 4 Baths
    • 2,756 Sq Ft

    4 S 1st St, Denton, MD 21629

    Outstanding Business Opportunity! Rare Find with-in Downtown Denton! Property would make an excellent Restaurant, Bar, great Venue , or a Large Victorian Home! Features include but not limited to Residential, Commerical or Mixed Use. Large Wrap around Porch for entertaining, Patio with plenty of room for seating with Firepit. Park like setting with Open Space and Large Pond! Town ERU's are

    Kathleen Brenton Brenton Realty Group

    4 S 1st St, Denton, MD 21629
  • /44

    $220,000

    Sold Oct 30, 2025

    148 Main St, Preston, MD 21655

    • 4 Beds
    • 2 Baths
    • 2,884 Sq Ft
    • Built 1880

    Last Sold Summary

    • $76/SF
    • 69 Days On Market

    Current Estimated Value $266,189

    Last Listing Agent Cheri Bruce-Phipps TTR Sotheby's International Realty

    148 Main St, Preston, MD 21655
    • /46

      Est $402,223

      Not Listed For Sale

      1706 Cattail Commons Way, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,136 Sq Ft
      • Built 2007
      1706 Cattail Commons Way, Denton, MD 21629

      Last Sold Summary

      • 56 Days On Market

  • /18

    $340,000

    $35K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,286 Sq Ft

    27279 Jenny Hye Ln, Marydel, MD 21649

    Welcome to Your Peaceful Retreat!This 3-bedroom, 2.5-bath split-foyer home offers 1,488 sq. ft. of comfortable living space, plus a full basement and an attached one-car garage. With its classic brick-and-siding exterior, inviting front patio, and serene surroundings, this property blends warmth, character, and endless potential.Step inside and imagine the possibilities—a bright, open

    Hudson Post Keller Williams Select Realtors of Easton

    27279 Jenny Hye Ln, Marydel, MD 21649

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