15,626

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
    • /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

    $149,900

    • Studio
    • 1,484 Sq Ft

    112 Noble Ave, Preston, MD 21655

    Investors! Subject to current month-to-month leases this duplex is located in the heart of Preston and close proximity to the school.

    Chuck Mangold Benson & Mangold, LLC

    112 Noble Ave, 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
    • /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

  • /28

    $405,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft

    25214 Smith Landing Rd, Denton, MD 21629

    Waterfront parcel on the Choptank River! 3 (possibly 4) bedroom, 2 full bath 2-story home on a 3.15 +/- acre fee simple parcel. Numerous shade trees and perennial plantings surround the home. Two (2) outbuildings await your vision. Located approximately 15 miles from the Harrington Raceway & Casino, 30 miles from the Bay Bridge and 50 miles from local beach resorts. Owner say to bring

    John Fifer Brokers Realty Group, LLC

    25214 Smith Landing Rd, 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 $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

  • /22

    $329,500

    $15K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft

    2691 Lorraine Ave, Federalsburg, MD 21632

    Discover 2691 Lorraine Ave, Federalsburg, MD 21632. This Cape Cod residence offers a spacious layout situated on over an acre of land at the end of a quiet cul-de-sac. The property features 4 beds, 2 baths, and a welcoming kitchen where all built in appliances stay. Enjoy a large living area with a fireplace and an entry-level bedroom for convenience. Step out onto the back deck to appreciate the

    Norman Domingo XRealty.NET LLC

    2691 Lorraine Ave, 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 $460,672

    Last Listing Agent Katie Moore Coldwell Banker Chesapeake Real Estate Company

    22889 Hog Creek Rd, Preston, MD 21655
    • /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

  • /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
  • /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
    • /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

  • /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
  • /28

    $223,660

    Sold Aug 21, 2025

    141 Riverwalk Terrace, Federalsburg, MD 21632

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

    Last Sold Summary

    • $164/SF
    • 96 Days On Market

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

    141 Riverwalk Terrace, 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

  • /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 $241,265

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

    7922 Detour Rd, Denton, MD 21629
    • /63

      Est $561,247

      Not Listed For Sale

      20735 Tammuxzena Dr, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 2,250 Sq Ft
      • Built 2025
      20735 Tammuxzena Dr, Preston, MD 21655

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Leo Kuneman Meredith Fine Properties

  • /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
  • /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 $342,024

    Last Listing Agent Lou Chirgott Core Maryland Real Estate LLC

    123 Briarwood Cir, Denton, MD 21629
    • /4

      Not Listed For Sale

      0 Bridgetown Rd Unit MDCM2005246, Goldsboro, MD 21636

      0 Bridgetown Rd Unit MDCM2005246, Goldsboro, MD 21636

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent William Norris Select Land & Homes, LLC

  • /2

    $199,900

    $60K 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
  • /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
    • /28

      Est $223,694

      Not Listed For Sale

      125 Riverwalk Terrace, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2024
      125 Riverwalk Terrace, Federalsburg, MD 21632

      Last Sold Summary

      • 42 Days On Market

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

  • /85

    $769,000

    $106K PRICE DROP
    • 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
  • /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
    • /27

      Est $217,249

      Not Listed For Sale

      119 Riverwalk Terrace, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2024
      119 Riverwalk Terrace, Federalsburg, MD 21632

      Last Sold Summary

      • 49 Days On Market

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

  • /4

    $200,000

    • 3 Beds
    • 1 Bath
    • 2,020 Sq Ft

    22971 Tuckahoe Springs Dr, Denton, MD 21629

    Ranch style home situated on a 1.18 acre lot. There is no access to the interior of the home. Priced below assessed value, home to be transferred occupied, as-is. Please do not disturb the occupants.

    Michael Johnson Marathon Real Estate

    22971 Tuckahoe Springs Dr, Denton, MD 21629
  • /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 $1,011,552

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    3069 Choptank Rd, Preston, MD 21655
    • /27

      Est $212,761

      Not Listed For Sale

      113 Riverwalk Terrace, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2024
      113 Riverwalk Terrace, Federalsburg, MD 21632

      Last Sold Summary

      • 0 Days On Market

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

  • /18

    $325,000

    $25K PRICE DROP Pending
    • 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
    • /14

      Not Listed For Sale

      12400 & 12316 Ridgely Rd, Greensboro, MD 21639

      • 3 Beds
      • 1 Bath
      • 1,896 Sq Ft
      • Built 1975
      12400 & 12316 Ridgely Rd, Greensboro, MD 21639

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent BRIAN MORRIS The Land Group

  • /23

    $295,000

    Under Contract
    • 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
  • /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
    • /27

      Est $222,891

      Not Listed For Sale

      117 Riverwalk Terrace, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2024
      117 Riverwalk Terrace, Federalsburg, MD 21632

      Last Sold Summary

      • 47 Days On Market

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

  • /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
  • /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

Showing Results 81 - 120, Page 3 of 18

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