15,577

Caroline County, MD Homes

Section Image
  • /16

    $130,500

    Sold Jun 15, 2026

    4310 Bethlehem Rd, Preston, MD 21655

    • 2 Beds
    • 1 Bath
    • 696 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Above List Price
    • $188/SF
    • 10 Days On Market

    Current Estimated Value $130,619

    Last Listing Agent James Bent Benson & Mangold, LLC

    4310 Bethlehem Rd, Preston, MD 21655
    • /24

      Est $359,539

      Not Listed For Sale

      5 Seward Rd, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,538 Sq Ft
      • Built 2017
      5 Seward Rd, Ridgely, MD 21660

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Amanda Morgan Brenton Realty Group

  • /47

    $425,000

    • 3 Beds
    • 1.5 Baths
    • 1,356 Sq Ft

    21370 Skeleton Creek Rd, Preston, MD 21655

    Very rustic and private 3 bedroom, 1 and a 1/2 bath log cabin on 15 private wooded acres. There is a large building and a sun porch overlooking a stream running through the property. Excellent hunting property for whitetail deer and turkey!

    Henry Gibbons-Neff Meredith Fine Properties

    21370 Skeleton Creek Rd, Preston, MD 21655
  • /22

    $115,000

    Sold Feb 27, 2026

    208 N Main St, Federalsburg, MD 21632

    • 4 Beds
    • 1.5 Baths
    • 2,668 Sq Ft
    • Built 1913

    Last Sold Summary

    • $43/SF
    • 106 Days On Market

    Current Estimated Value $205,993

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

    208 N Main St, Federalsburg, MD 21632
    • /3

      Not Listed For Sale

      0 River Rd, Greensboro, MD 21639

      0 River Rd, Greensboro, MD 21639

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Linda Moore Long & Foster Real Estate, Inc.

  • /83

    $779,000

    Under Contract
    • 5 Beds
    • 5 Baths
    • 3,816 Sq Ft

    8821 Dorothy Ln, Denton, MD 21629

    " Diamond in the Rough" This property is being sold to settle an estate and no repairs will be made. Offering considerable upside potential, this well built, private, 5 bedroom, 5 bath home is tucked away on the Choptank River in the community of Asbury. Featuring a large, open kitchen/living area with fireplace, first floor primary suite, inground pool and private pier.

    Andrew Beaven Wright Real Estate

    8821 Dorothy Ln, Denton, MD 21629
  • /34

    $469,000

    Sold Oct 10, 2025

    25790 Herring Ln, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 2,132 Sq Ft
    • Built 1989

    Last Sold Summary

    • $220/SF
    • 18 Days On Market

    Current Estimated Value $468,207

    Last Listing Agent Elizabeth Tryon Coldwell Banker Realty

    25790 Herring Ln, Denton, MD 21629
    • /27

      Est $218,928

      Not Listed For Sale

      149 Riverwalk Terrace, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2025
      149 Riverwalk Terrace, Federalsburg, MD 21632

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

  • /38

    $99,000

    • Land
    • 9,147 Sq Ft
    • $471,429 per Acre

    504 Central Ave, Ridgely, MD 21660

    UPDATE: The New Ridgely Comprehensive Plan draft will designate this lot for future commercial growth alongside the adjoining property—making this a strong investment opportunity. Call to request the documentation. This .21-acre vacant lot is ideally located in the heart of Ridgely. Currently zoned residential, yet future commercial allowance almost finalized - it offers access to public water

    Allie Harris Taylor Properties

    504 Central Ave, Ridgely, MD 21660
  • /25

    $465,000

    Sold May 20, 2026

    22889 Hog Creek Rd, Preston, MD 21655

    • 4 Beds
    • 2.5 Baths
    • 1,872 Sq Ft
    • Built 1990

    Last Sold Summary

    • $248/SF
    • 3 Days On Market

    Current Estimated Value $460,672

    Last Listing Agent Katie Moore Coldwell Banker Chesapeake Real Estate Company

    22889 Hog Creek Rd, Preston, MD 21655
    • /27

      Est $219,597

      Not Listed For Sale

      143 Riverwalk Terrace, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2025
      143 Riverwalk Terrace, Federalsburg, MD 21632

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

  • /44

    $499,900

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

    12384 River Rd, Ridgely, MD 21660

    Move Right In! METICULOUSLY MAINTAINED home in a rural setting just outside of Downtown Ridgely. This 4 bedroom, 2.5 bath home is the perfect combination of modern and laid back, with two additional flex space rooms for a potential of two more bedrooms. Upgrades are too many to name all of them. Just a few being insulated garage and doors, two zone gas and electric heat pumps, tankless hot water

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    12384 River Rd, Ridgely, MD 21660
  • /26

    $402,000

    Sold Dec 09, 2025

    1111 Daylily Ln, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 3,838 Sq Ft
    • Built 2007

    Last Sold Summary

    • $105/SF
    • 7 Days On Market

    Current Estimated Value $415,278

    Last Listing Agent Terri Murray RE/MAX Executive

    1111 Daylily Ln, Denton, MD 21629
    • /5

      Est $48,112

      Not Listed For Sale

      26302 Sennett Rd, Denton, MD 21629

      • Built 1977
      26302 Sennett Rd, Denton, MD 21629

      Last Sold Summary

      • 233 Days On Market

      Last Listing Agent Michelle Anderson Coldwell Banker Premier - Seaford

  • /32

    $599,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    28402 Liden School Rd, Denton, MD 21629

    This is the one! Approx. 16.77 acres with an owner built 3 bedroom home. One acre with home plus additional acreage. Some acreage is wooded with wild life including, but not limited to, rabbit, deer, and turkey. This home has magnificent kitchen with custom cabinetry and SS appliances, including a 5 burner stove and double wall oven. Pellet stove is included for those cool evenings and damp days.

    Michael Shipley Benson & Mangold, LLC.

    28402 Liden School Rd, Denton, MD 21629
  • /10

    $215,000

    Sold May 28, 2026

    7922 Detour Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,286 Sq Ft
    • Built 1990

    Last Sold Summary

    • 16% Below List Price
    • $167/SF
    • 24 Days On Market

    Current Estimated Value $228,520

    Last Listing Agent Barbara Blosser Long & Foster Real Estate, Inc.

    7922 Detour Rd, Denton, MD 21629
    • /24

      Est $352,244

      Not Listed For Sale

      5540 American Corner Rd, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 2025
      5540 American Corner Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • /73

    $385,000

    • 3 Beds
    • 1 Bath
    • 1,370 Sq Ft

    506 Central Ave, Ridgely, MD 21660

    Historic Home + Separate Buildable Parcel with Investment Potential!Step back in time while enjoying the flexibility and possibilities this unique Main Street property offers. Built in 1880, this 3-bedroom, 1-bath home offers approximately 1,370 sq. ft. and retains original character throughout, including original hardwood flooring beneath carpeting in portions of the home.The

    Allie Harris Taylor Properties

    506 Central Ave, Ridgely, MD 21660
  • /26

    $295,000

    Sold Dec 30, 2025

    504 Pintail St, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft
    • Built 2024

    Last Sold Summary

    • $177/SF
    • 133 Days On Market

    Current Estimated Value $317,674

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    504 Pintail St, Greensboro, MD 21639
    • /17

      Not Listed For Sale

      223 Old Denton Rd, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,488 Sq Ft
      • Built 1900
      223 Old Denton Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Benjamin Smith Real Broker, LLC

  • /2

    $190,000

    $70K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,280 Sq Ft

    27944 Possum Hill Rd, Federalsburg, MD 21632

    Lovely two bedroom one bath rancher with spacious living room and dining room plus kitchen **1 car garage plus 30 x 30 storage area ** Heating is oil furnace 3 years old** Hot water tank is 3 years old **1.42 acres ** very flat usable lot

    Bev Langley Coldwell Banker Realty

    27944 Possum Hill Rd, Federalsburg, MD 21632
  • /18

    $475,000

    Sold Dec 22, 2025

    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649

    • Land
    • 53.01 Acres
    • $8,961 per Acre

    Last Sold Summary

    • 140 Days On Market

    Last Listing Agent Benjamin Alder The Land Group

    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649
    • /28

      Est $232,489

      Not Listed For Sale

      151 Riverwalk Terrace, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2025
      151 Riverwalk Terrace, Federalsburg, MD 21632

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

  • /85

    $769,000

    $106K PRICE DROP Pending
    • 3 Beds
    • 3 Baths
    • 3,149 Sq Ft

    3547 Prchal Rd, Preston, MD 21655

    **Don't Miss This Rare Opportunity**Pride of ownership shines throughout this beautifully appointed home, featuring 3 bedrooms, a bonus room, 3 full bathrooms, a dedicated office space and much more- set on over 4 serene acres. This property includes approximately 2.5 wooded acres with private walking trails and an abundance of wildlife. Major 2025 home improvements including a brand new

    Amy Endzel Keller Williams Select Realtors of Annapolis

    3547 Prchal Rd, Preston, MD 21655
  • /88

    $930,000

    Sold Sep 30, 2025

    3069 Choptank Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,512 Sq Ft
    • Built 2003

    Last Sold Summary

    • $370/SF
    • 11 Days On Market

    Current Estimated Value $912,056

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    3069 Choptank Rd, Preston, MD 21655
    • /27

      Est $221,970

      Not Listed For Sale

      147 Riverwalk Terrace, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2025
      147 Riverwalk Terrace, Federalsburg, MD 21632

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

  • /27

    $225,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 1,096 Sq Ft

    215 N Main St, Federalsburg, MD 21632

    Welcome to this charming 3BR/2BA classic Craftsman. Pull into the driveway and make your way to the covered front porch and the door to your forever home. Step inside to discover a home filled with original character, including beautiful original hardwood floors throughout. The main level showcases the traditional layout and timeless charm of a Craftsman, featuring a spacious living room that

    Jordan Larigan LPT Realty, LLC

    215 N Main St, Federalsburg, MD 21632
  • /14

    $399,000

    Sold Apr 07, 2026

    13920 Quail Ct, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • Built 2026

    Last Sold Summary

    • 26 Days On Market

    Last Listing Agent Barbara Blosser Long & Foster Real Estate, Inc.

    13920 Quail Ct, Greensboro, MD 21639
    • /6

      Not Listed For Sale

      3449 Jefferson Pond Rd, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 2025
      3449 Jefferson Pond Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Amy Herr Keller Williams Realty

  • /25

    $235,000

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    158 Wright St, Preston, MD 21655

    Bring your vision and make this spacious Preston home your own! Offering more than 1,800 square feet, this property features three bedrooms, two full bathrooms, and plenty of room to create a home that fits your style. While the interior is ready for updates, the generous floor plan provides a great foundation for renovation and personalization. Located in the Colonel Richardson School District,

    Heather Brummell Keller Williams Realty

    158 Wright St, Preston, MD 21655
  • /44

    $295,900

    Sold Dec 31, 2025

    3622 Choptank Rd, Preston, MD 21655

    • 2 Beds
    • 1.5 Baths
    • 1,700 Sq Ft
    • Built 1961

    Last Sold Summary

    • $174/SF
    • 2 Days On Market

    Current Estimated Value $323,739

    Last Listing Agent Brooke Tephabock LPT Realty, LLC

    3622 Choptank Rd, Preston, MD 21655
    • /7

      Not Listed For Sale

      0 Burnt Mill Rd Unit MDCM2005304, Ridgely, MD 21660

      0 Burnt Mill Rd Unit MDCM2005304, Ridgely, MD 21660

      Last Sold Summary

      Last Listing Agent Gretchen Wichlinski Compass

  • /57

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft

    15078 Drapers Mill Rd, Greensboro, MD 21639

    A truly unique property offering multiple dwellings, abundant storage, and exceptional flexibility! The property features multiple residential structures, providing a variety of possibilities for extended family, guests, home offices, hobbies, or additional living space, three separate lots to make a total 7.944 acres.Car enthusiasts, contractors, and hobbyists will appreciate the spacious

    Kat Thompson Benson & Mangold, LLC.

    15078 Drapers Mill Rd, Greensboro, MD 21639
  • /27

    $209,990

    Sold Feb 24, 2026

    120 Julie Ln, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Last Sold Summary

    • $154/SF
    • 13 Days On Market

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

    120 Julie Ln, Federalsburg, MD 21632
    • /7

      Not Listed For Sale

      0 Burnt Mill Rd Unit MDCM2005302, Ridgely, MD 21660

      0 Burnt Mill Rd Unit MDCM2005302, Ridgely, MD 21660

      Last Sold Summary

      Last Listing Agent Gretchen Wichlinski Compass

  • /26

    $390,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    25519 Linhard Ln, Greensboro, MD 21639

    Enjoy the peace and privacy of country living on this lovely 4.68-acre property. This well-maintained one-level rancher features durable luxury vinyl plank (LVP) flooring and an upgraded kitchen with elegant quartz countertops, ample cabinetry with soft close feature plus under cabinet lighting.This home offers 3 bedrooms and 2 full baths, providing comfortable living space for family and

    Jimmy White Long & Foster Real Estate, Inc.

    25519 Linhard Ln, Greensboro, MD 21639
  • /29

    $325,000

    Sold Oct 06, 2025

    614 Market St, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,508 Sq Ft
    • Built 1890

    Last Sold Summary

    • $130/SF
    • 53 Days On Market

    Current Estimated Value $334,719

    Last Listing Agent Michael Bozek Michael J. Bozek

    614 Market St, Denton, MD 21629
    • /68

      Est $535,599

      Not Listed For Sale

      25879 Brookwood Rd, Greensboro, MD 21639

      • 4 Beds
      • 3.5 Baths
      • 3,788 Sq Ft
      • Built 2023
      25879 Brookwood Rd, Greensboro, MD 21639

      Last Sold Summary

      • 127 Days On Market

      Last Listing Agent Brett Schrader Taylor Properties

  • /25

    $325,000

    • 4 Beds
    • 2 Baths
    • 1,539 Sq Ft

    306 Sunrise Ave, Ridgely, MD 21660

    Nestled on a charming corner lot, this delightful ranch-style home offers a perfect blend of comfort and community. Built in 1955, this residence boasts a spacious layout with 1,539 square feet of living space, featuring four inviting bedrooms and two full bathrooms. The warm ambiance is enhanced by a mix of hardwood and carpet flooring, creating a cozy atmosphere throughout. The exterior,

    Vincent De Lorenzo Samson Properties

    306 Sunrise Ave, Ridgely, MD 21660
  • /2

    $670,000

    Sold May 22, 2026

    12820 Porters Landing Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 2,676 Sq Ft
    • Built 1989

    Last Sold Summary

    • 11% Below List Price
    • $250/SF
    • 86 Days On Market

    Current Estimated Value $679,064

    Last Listing Agent Penny Hollis Samson Properties

    12820 Porters Landing Rd, Greensboro, MD 21639

Showing Results 81 - 120, Page 3 of 18

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