15,718

Caroline County, MD Homes

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  • /16

    $260,000

    • 3 Beds
    • 2 Baths
    • 1,192 Sq Ft

    508 N 6th St, Denton, MD 21629

    Enjoy convenient one-level living on the north side of Denton, just a stone's throw from Bullock's and with easy access to Route 404 for commuting. Built in 2002, this charming 3-bedroom, 2-bath cottage offers a comfortable and functional layout. Enter from the side porch into a welcoming foyer that opens to the spacious living room, featuring a vaulted ceiling and cozy gas fireplace. Upgraded

    Traci Jordan Meredith Fine Properties

    508 N 6th St, Denton, MD 21629
  • /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 $151,850

    Last Listing Agent James Bent Benson & Mangold, LLC

    4310 Bethlehem Rd, Preston, MD 21655
    • /55

      Est $412,519

      Not Listed For Sale

      305 Morning Glory Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,646 Sq Ft
      • Built 2021
      305 Morning Glory Dr, Denton, MD 21629

      Last Sold Summary

      • 37 Days On Market

  • /15

    $118,000

    • 3 Beds
    • 1.5 Baths
    • 1,664 Sq Ft

    501 Lincoln St, Denton, MD 21629

    Property is being sold As/ Is. Located on a corner lot. Owner has completed some work to the property, but additional work will be required. Please contact Denton Planning and Codes to verify remaining requirements to obtain an occupancy permit.

    Diane Wenk Wright Real Estate

    501 Lincoln St, Denton, MD 21629
  • /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 $205,289

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

    208 N Main St, Federalsburg, MD 21632
    • /41

      Est $385,113

      Not Listed For Sale

      106 Morning Glory Dr, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,664 Sq Ft
      • Built 2022
      106 Morning Glory Dr, Denton, MD 21629

      Last Sold Summary

      • 254 Days On Market

  • /22

    $467,900

    Coming Soon
    • 3 Beds
    • 4 Baths
    • 2,713 Sq Ft

    202 N Central Ave, Ridgely, MD 21660

    Charming Victorian home in the heart of Ridgely, ideally situated on a picturesque, tree-shaded corner lot. This timeless property offers classic character, curb appeal, and a prime location close to local amenities. An expansive wraparound front porch sets the stage for this beautiful home, featuring a gracious entryway, stunning columned foyer, and gleaming hardwood floors that enhance its

    Marcia Rostien Long & Foster Real Estate, Inc.

    202 N Central Ave, Ridgely, MD 21660
  • /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 $453,382

    Last Listing Agent Elizabeth Tryon Coldwell Banker Realty

    25790 Herring Ln, Denton, MD 21629
    • /17

      Not Listed For Sale

      9810 Corkell Rd, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,092 Sq Ft
      • Built 1974
      9810 Corkell Rd, Denton, MD 21629

      Last Sold Summary

      • 37 Days On Market

  • /5

    $305,000

    New Construction Pending
    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    3390 Jefferson Pond Rd, Federalsburg, MD 21632

    Beautiful new construction in a charming, up-and-coming community! This 3-bedroom, 2-bath home features an open-concept layout with luxury vinyl plank flooring throughout the main living areas. The spacious kitchen offers granite countertops, modern finishes, and seamless flow into the living and dining spaces—perfect for entertaining. Built for peace of mind with 30-year architectural shingles

    Amy Herr Keller Williams Realty

    3390 Jefferson Pond Rd, Federalsburg, MD 21632
  • /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 $461,906

    Last Listing Agent Katie Moore Coldwell Banker Chesapeake Real Estate Company

    22889 Hog Creek Rd, Preston, MD 21655
    • /9

      Est $222,438

      Not Listed For Sale

      19 S 8th St, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 1981
      19 S 8th St, Denton, MD 21629

      Last Sold Summary

      • 9 Days On Market

  • /25

    $230,000

    $50K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft

    28241 Hickman Cannery Rd, Denton, MD 21629

    Welcome to 28241 Hickman Cannery Road, a refreshed two-story home in Denton, MD, blending classic charm with modern, low-maintenance updates. Luxury vinyl plank flooring runs throughout both levels, creating a cohesive, move-in-ready feel. The main level offers a bright living room, a flexible den ideal for a home office or family room, a spacious kitchen, dedicated laundry room, and a full

    Billy Mister Keller Williams Realty

    28241 Hickman Cannery Rd, Denton, MD 21629
  • /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 $402,010

    Last Listing Agent Terri Murray RE/MAX Executive

    1111 Daylily Ln, Denton, MD 21629
    • /4

      Not Listed For Sale

      0 Rte 313 Rd Unit 1001900376, Federalsburg, MD 21632

      0 Rte 313 Rd Unit 1001900376, Federalsburg, MD 21632

      Last Sold Summary

      • 1,412 Days On Market

  • /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
  • /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 $259,287

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

    7922 Detour Rd, Denton, MD 21629
    • /26

      Est $486,487

      Not Listed For Sale

      11490 Maplewood Dr, Ridgely, MD 21660

      • 4 Beds
      • 3 Baths
      • 2,346 Sq Ft
      • Built 2019
      11490 Maplewood Dr, Ridgely, MD 21660

      Last Sold Summary

      • 6 Days On Market

  • /26

    $310,000

    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft

    25389 Kent St, Greensboro, MD 21639

    This charming one-level home is situated on a spacious 0.58-acre lot in the desirable Passapae Landing community. Offering 1,152 square feet of living space, this home features comfortable living areas, an attached garage, a large deck perfect for outdoor entertaining, and a gazebo for relaxing and enjoying the outdoors. Residents of Passapae Landing enjoy community access to the beautiful

    Heather Brummell Keller Williams Realty

    25389 Kent St, Greensboro, MD 21639
  • /30

    $340,000

    Sold Aug 20, 2025

    123 Briarwood Cir, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Built 2015

    Last Sold Summary

    • $170/SF
    • 64 Days On Market

    Current Estimated Value $335,206

    Last Listing Agent Lou Chirgott Core Maryland Real Estate LLC

    123 Briarwood Cir, Denton, MD 21629
    • /23

      Est $330,089

      Not Listed For Sale

      323 Mallard Dr, Greensboro, MD 21639

      • 3 Beds
      • 2.5 Baths
      • 1,632 Sq Ft
      • Built 2023
      323 Mallard Dr, Greensboro, MD 21639

      Last Sold Summary

      • 10 Days On Market

  • /32

    $625,000

    • 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
  • /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 $309,089

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    504 Pintail St, Greensboro, MD 21639
    • /30

      Est $313,739

      Not Listed For Sale

      319 Mallard Dr, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,468 Sq Ft
      • Built 2023
      319 Mallard Dr, Greensboro, MD 21639

      Last Sold Summary

      • 35 Days On Market

  • /2

    $210,000

    $50K 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
    • /66

      Est $318,771

      Not Listed For Sale

      25970 Three Bridges Rd, Federalsburg, MD 21632

      • 4 Beds
      • 2 Baths
      • 1,844 Sq Ft
      • Built 1996
      25970 Three Bridges Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 71 Days On Market

  • /85

    $799,000

    $76K PRICE DROP
    • 4 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 property set on over 4 serene acres, including approximately 2.5 wooded acres with private walking trails and an abundance of wildlife. Major 2025 home improvements including a brand new roof, siding and 10 Velux skylights, along with a new Bosch heat pump installed in 2024. This one-of-a-kind

    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 $899,211

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    3069 Choptank Rd, Preston, MD 21655
    • /19

      Est $241,243

      Not Listed For Sale

      206 Maple Ave, Ridgely, MD 21660

      • 2 Beds
      • 1.5 Baths
      • 1,248 Sq Ft
      • Built 1890
      206 Maple Ave, Ridgely, MD 21660

      Last Sold Summary

      • 17 Days On Market

  • /18

    $325,000

    $25K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 2,302 Sq Ft

    25865 Brookwood Rd, Greensboro, MD 21639

    Sold as-is. Spacious 3 bedroom 2 full bathroom rancher located in sought-after Fox Grape neighborhood. Home is situated on private, wooded 1.23+/- acre lot. Included in the sale is an additional, adjacent .60+/- acre wooded lot for a total of 1.83+/- acres of land. Newer kitchen cabinets. Nice concrete patio, paved driveway and detached two car garage with additional workshop with power and

    Brian Petzold Benson & Mangold, LLC

    25865 Brookwood Rd, Greensboro, MD 21639
  • /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
    • /5

      Est $518,604

      Not Listed For Sale

      24776 Tribbett Cir, Ridgely, MD 21660

      • Built 2025
      24776 Tribbett Cir, Ridgely, MD 21660

      Last Sold Summary

      • 261 Days On Market

  • /12

    $82,500

    $53K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    103 Chambers St, Preston, MD 21655

    This Colonial home features timeless architecture and thoughtful design. The property offers solid construction and classic appeal, making it an excellent opportunity for discerning buyers. This distinctive property presents an outstanding opportunity for transformation and value creation. The established neighborhood setting combines small-town charm with practical accessibility to essential

    Pamela Geib Long & Foster Real Estate, Inc.

    103 Chambers 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 $308,050

    Last Listing Agent Brooke Tephabock LPT Realty, LLC

    3622 Choptank Rd, Preston, MD 21655
    • /27

      Est $360,650

      Not Listed For Sale

      1202 Trice Meadows Cir, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,540 Sq Ft
      • Built 2010
      1202 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 25 Days On Market

  • /23

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,646 Sq Ft

    130 Charlotte Ave, Federalsburg, MD 21632

    Welcome to 130 Charlotte Avenue in Federalsburg, Maryland—a well-appointed home offering three bedrooms, two full baths, and an attached two-car garage with a versatile bonus room above, ideal for a home office, gym, or guest space. Tucked away at the end of a quiet cul-de-sac, this property provides private outdoor enjoyment while remaining conveniently located for an easy commute to Seaford and

    FRANK LITTLE Berkshire Hathaway HomeServices PenFed Realty

    130 Charlotte Ave, Federalsburg, MD 21632
  • /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
    • /10

      Est $402,206

      Not Listed For Sale

      1101 Trice Meadows Cir, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,300 Sq Ft
      • Built 2023
      1101 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 95 Days On Market

  • /2

    $390,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    25519 Linhard Ln, Greensboro, MD 21639

    Coming Soon! 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.This home offers 3 bedrooms and 2 full baths, providing comfortable living space for family and guests. Exterior features include

    Jimmy White Long & Foster Real Estate, Inc.

    25519 Linhard Ln, Greensboro, MD 21639

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