15,709

Caroline County, MD Homes

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    • /12

      Est $371,929 Not Listed For Sale

      1108 Trice Meadows Cir, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 2023
      1108 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 6% Above List Price
      • $233/SF
      • 147 Days On Market
      • Last Sold Price $349,900
      • Mar 01, 2024

      Last Listing Agent Michelle DiDonato Island Realty, LLC

  • /16

    $129,000

    • 2 Beds
    • 1 Bath
    • 696 Sq Ft

    4310 Bethlehem Rd, Preston, MD 21655

    Investment opportunity or enjoy a very private (1) one acre country location to develop and enjoy. Oportities to improve and / or expand this small cottage home. Included is a solid (2) two car detached garage. Septic system may need replacement and well is original to 1976.

    James Bent Benson & Mangold, LLC

    4310 Bethlehem Rd, Preston, MD 21655
  • /30

    $435,000 Sold Aug 11, 2025

    4808 Frazier Neck Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • Built 1920

    Last Sold Summary

    • $275/SF
    • 88 Days On Market

    Current Estimated Value $431,529

    Last Listing Agent Brenda Fornos Taylor Properties

    4808 Frazier Neck Rd, Preston, MD 21655
    • /74

      Not Listed For Sale

      4439 Bethlehem Rd, Preston, MD 21655

      • 5 Beds
      • 2.5 Baths
      • 2,560 Sq Ft
      • Built 1900
      4439 Bethlehem Rd, Preston, MD 21655

      Last Sold Summary

      • 33% Below List Price
      • $326/SF
      • 106 Days On Market
      • Last Sold Price $835,000
      • Dec 03, 2024

      Last Listing Agent Mickey Hayward Sunset Properties

  • /10

    $239,999

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

    7922 Detour Rd, Denton, MD 21629

    Investor Alert! Great opportunity for a handyman or savvy investor. This 3-bedroom, 2-bath home is situated in a great, private location and offers plenty of potential for the right buyer. The property features a 1-car garage, a spacious backyard perfect for outdoor activities or play, and a deck off the back—ideal for relaxing or entertaining. While the home does require renovations, it presents

    Barbara Blosser Long & Foster Real Estate, Inc.

    7922 Detour Rd, Denton, MD 21629
  • /5

    $46,000 Sold Dec 10, 2025

    402 Lot 3 N S Sunset Ave, Greensboro, MD 21639

    • Land
    • 11,761 Sq Ft
    • $170,370 per Acre

    Last Sold Summary

    • 195 Days On Market

    Last Listing Agent Lisa Knotts Coldwell Banker Realty

    402 Lot 3 N S Sunset Ave, Greensboro, MD 21639
    • /48

      Est $329,629 Not Listed For Sale

      6 Maple Ave, Ridgely, MD 21660

      • 4 Beds
      • 2 Baths
      • 2,492 Sq Ft
      • Built 1957
      6 Maple Ave, Ridgely, MD 21660

      Last Sold Summary

      • 18% Above List Price
      • $112/SF
      • 11 Days On Market
      • Last Sold Price $280,000
      • Mar 08, 2024

      Last Listing Agent Phill Whitby Long & Foster

  • /76

    $875,000

    • 4 Beds
    • 3 Baths
    • 3,149 Sq Ft

    3547 Prchal Rd, Preston, MD 21655

    Pride of ownership shines throughout this beautifully appointed home set on over 4 acres, including approximately 2.5 wooded acres with peaceful walking trails —or a great spot for hunting already equipped with a deer stand.A major renovation in 2006 nearly doubled the living space, transforming the property into a spacious 4-bedroom, 3-bathroom residence designed for both comfortable living

    Amy Endzel Keller Williams Select Realtors of Annapolis

    3547 Prchal Rd, Preston, MD 21655
  • /28

    $209,990 Sold Sep 15, 2025

    116 Julie Ln, Federalsburg, MD 21632

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

    Move in Ready Sold Summary

    • $154/SF
    • 12 Days On Market

    116 Julie Ln, Federalsburg, MD 21632
    • /15

      Est $160,305 Not Listed For Sale

      128 Bloomingdale Ave, Federalsburg, MD 21632

      • 5 Beds
      • 3.5 Baths
      • 4,316 Sq Ft
      • Built 1860
      128 Bloomingdale Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 8% Below List Price
      • $41/SF
      • 245 Days On Market
      • Last Sold Price $175,000
      • Jul 21, 2023

      Last Listing Agent Pamela Geib Long & Foster

  • /12

    $89,900

    • 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
  • /7

    $105,000 Sold Mar 23, 2026

    22691 Sawmill Rd, Ridgely, MD 21660

    • 2 Beds
    • 1 Bath
    • 1,088 Sq Ft
    • Built 1945

    Last Sold Summary

    • 16% Below List Price
    • $97/SF
    • 6 Days On Market

    Current Estimated Value $150,031

    Last Listing Agent Amanda Morgan Brenton Realty Group

    22691 Sawmill Rd, Ridgely, MD 21660
    • /31

      Est $521,580 Not Listed For Sale

      5132 Clark Canning House Rd, Federalsburg, MD 21632

      • 4 Beds
      • 2.5 Baths
      • 2,200 Sq Ft
      • Built 1930
      5132 Clark Canning House Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 4% Above List Price
      • $227/SF
      • 353 Days On Market
      • Last Sold Price $500,000
      • Jan 08, 2024

      Last Listing Agent Bobby Gorski The Land Group

  • /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
  • /32

    $310,000 Sold Feb 20, 2026

    407 Wood Duck Dr, Greensboro, MD 21639

    • 4 Beds
    • 2.5 Baths
    • 1,624 Sq Ft
    • Built 2004

    Last Sold Summary

    • $191/SF
    • 149 Days On Market

    Current Estimated Value $315,678

    Last Listing Agent Kathryn Matic Patterson-Schwartz - Greenville

    407 Wood Duck Dr, Greensboro, MD 21639
    • /20

      Est $270,080 Not Listed For Sale

      306 N Academy St, Greensboro, MD 21639

      • 2 Beds
      • 1 Bath
      • 1,440 Sq Ft
      • Built 1948
      306 N Academy St, Greensboro, MD 21639

      Last Sold Summary

      • 13% Above List Price
      • $167/SF
      • 169 Days On Market
      • Last Sold Price $240,000
      • May 16, 2023

      Last Listing Agent Stacie Luhrman Benson & Mangold, LLC

  • /14

    $120,000

    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    26471 Three Bridges Rd, Federalsburg, MD 21632

    **Back Active at no fault of the seller**Opportunity awaits at 26471 Three Bridges Rd in Federalsburg, MD! This partially remodeled 2-bedroom, 2-bath home is ready for your finishing touch. Inside, the property has been taken down to the framing and subflooring, giving you a true blank canvas to bring your vision to life—whether you’re an investor looking for your next project or a buyer ready to

    LEE MARLAND Keller Williams Realty

    26471 Three Bridges Rd, Federalsburg, MD 21632
  • /28

    $229,990 Sold Aug 05, 2025

    141 Riverwalk Terrace, Federalsburg, MD 21632

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

    Move in Ready Sold Summary

    • $168/SF
    • 21 Days On Market

    141 Riverwalk Terrace, Federalsburg, MD 21632
    • /7

      Est $281,360 Not Listed For Sale

      128 Mill St, Greensboro, MD 21639

      • 3 Beds
      • 1 Bath
      • 1,890 Sq Ft
      • Built 1981
      128 Mill St, Greensboro, MD 21639

      Last Sold Summary

      • 6% Above List Price
      • $140/SF
      • 18 Days On Market
      • Last Sold Price $265,000
      • Mar 05, 2025

      Last Listing Agent Phill Whitby Long & Foster

  • /21

    $238,900

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    103 Riverwalk Terrace, Federalsburg, MD 21632

    This is an opportunity to buy in the sold out community of Riverwalk Terrace. The owner stayed at the home a few times some of the appliances never used. Open floor plan 1365 square feet , 3 bedrooms and 2.5 baths easy living. Only 2 years young this unit feels like new, was never a rental barley lived in. also backs up to the woods the private side of the community. Another perk to this location

    Kat Thompson Benson & Mangold, LLC.

    103 Riverwalk Terrace, Federalsburg, MD 21632
  • /3

    $94,900 Sold Oct 03, 2025

    9709 Foy Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 2,312 Sq Ft
    • Built 1900

    Last Sold Summary

    • $41/SF
    • 13 Days On Market

    Current Estimated Value $154,667

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    9709 Foy Rd, Denton, MD 21629
    • /26

      Est $347,174 Not Listed For Sale

      13274 Greensboro Rd, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft
      • Built 1925
      13274 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 34% Above List Price
      • $139/SF
      • 18 Days On Market
      • Last Sold Price $260,000
      • Jun 06, 2023

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • /22

    $189,000

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    107 Smith St, Federalsburg, MD 21632

    Move-In Ready & Beautifully Remodeled!This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort and convenience. Enjoy a spacious living room, separate dining area, and a dedicated laundry room for added functionality.The kitchen is designed for both everyday living and entertaining, featuring dual bar seating areas with open views to the living and dining spaces. One

    Dawn Hubbard Keller Williams Select Realtors of Cambridge

    107 Smith St, Federalsburg, MD 21632
  • /31

    $260,000 Sold Aug 01, 2025

    213 S 6th St, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1983

    Last Sold Summary

    • $232/SF
    • 5 Days On Market

    Current Estimated Value $264,606

    Last Listing Agent Christian Schou TTR Sotheby's International Realty

    213 S 6th St, Denton, MD 21629
    • /6

      Est $267,537 Not Listed For Sale

      105 Chamber St, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,140 Sq Ft
      • Built 2024
      105 Chamber St, Preston, MD 21655

      Last Sold Summary

      • 1% Below List Price
      • $237/SF
      • Last Sold Price $269,900
      • Aug 16, 2024

      Last Listing Agent Sean Steward Century 21 Home Team Realty

  • /65

    $555,555 Pending

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

    17753 Marvel Rd, Marydel, MD 21649

    2021 Built Colonial Home on 4.41 Private Acres Near Delaware Beaches This modern 4-bedroom, 3-bath Colonial built in 2021 sits on 4.41 private acres and offers the rare combination of new construction, usable land, and convenient access to the Delaware beaches and tax-free shopping. Designed for comfort and flexibility, the home features a main-level primary suite, making one-level living

    Vincent Payne Realty Navigator

    17753 Marvel Rd, Marydel, MD 21649
  • /18

    $195,000 Sold Jun 27, 2025

    7 S 7th St, Denton, MD 21629

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 1880

    Last Sold Summary

    • $162/SF
    • 33 Days On Market

    Current Estimated Value $211,594

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    7 S 7th St, Denton, MD 21629
    • /31

      Not Listed For Sale

      22510 Ash Blvd, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,612 Sq Ft
      • Built 1999
      22510 Ash Blvd, Preston, MD 21655

      Last Sold Summary

      • $129/SF
      • 4 Days On Market
      • Last Sold Price $208,250
      • Aug 29, 2023

      Last Listing Agent Brooke Tephabock LPT Realty, LLC

  • /3

    $265,000

    • 2 Beds
    • 1 Bath
    • 1,092 Sq Ft

    10819 Greensboro Rd, Denton, MD 21629

    This home will be a Total Renovation in 2026. Consisting of 2 BR and 1 Bath. Situated on almost a half ac. Lovely back yard, and new Well.

    Barbara Beaudet Brenton Realty Group

    10819 Greensboro Rd, Denton, MD 21629
  • /37

    $295,000 Sold Apr 10, 2026

    1106 Osprey Ln, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,752 Sq Ft
    • Built 2004

    Last Sold Summary

    • $168/SF
    • 15 Days On Market

    Current Estimated Value $297,594

    Last Listing Agent Barbara McCaffrey Redfin Corp

    1106 Osprey Ln, Denton, MD 21629
    • /14

      Est $153,283 Not Listed For Sale

      136 Halltown Rd, Marydel, MD 21649

      • 3 Beds
      • 1.5 Baths
      • 1,440 Sq Ft
      • Built 1900
      136 Halltown Rd, Marydel, MD 21649

      Last Sold Summary

      • 5% Above List Price
      • $101/SF
      • 7 Days On Market
      • Last Sold Price $146,000
      • Mar 21, 2025

      Last Listing Agent Dawn Loeffler Thurston Wyatt Real Estate, LLC

  • /37

    $250,000 Pending

    • 2 Beds
    • 2 Baths
    • 2,024 Sq Ft

    705 S 2nd St, Denton, MD 21629

    Welcome to 705 S 2nd St, a spacious home set on a .46-acre corner lot in one of Denton’s most desirable areas. Offering approximately 2,000 square feet, this property presents a fantastic opportunity for buyers looking to personalize a home and add long-term value. The main level features a large living room, formal dining area, and an open kitchen layout, along with a bright rear sunroom that

    Kaitlyn Collins Benson & Mangold, LLC

    705 S 2nd St, Denton, MD 21629
  • /23

    $286,990 Sold Feb 06, 2026

    133 Hobbs St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft
    • Built 2025

    Last Sold Summary

    • $235/SF
    • 36 Days On Market

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

    133 Hobbs St, Greensboro, MD 21639
    • /17

      Est $444,184 Not Listed For Sale

      3498 Pepper Rd, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1996
      3498 Pepper Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 6% Above List Price
      • $250/SF
      • 49 Days On Market
      • Last Sold Price $420,000
      • Jul 25, 2023

      Last Listing Agent Barbara Nichols Results Realty Inc.

  • /12

    $575,000

    • Land
    • 61.88 Acres
    • $9,292 per Acre

    17619 Melville Rd, Henderson, MD 21640

    The Melville Rd Farm is located on the east side of Melville Road and is bordered to the north by Trunk Line Road. The property includes approximately 51± acres of tillable ground along with 11± acres of wooded areas primarily situated around drainage ditches, providing natural transitions and wildlife cover. Two transmission lines run through the center of the farm, offering access corridors and

    Benjamin Alder The Land Group

    17619 Melville Rd, Henderson, MD 21640
  • /14

    $95,000 Sold May 22, 2025

    8320 Detour Rd, Denton, MD 21629

    • Land
    • 2.09 Acres
    • $45,455 per Acre

    Last Sold Summary

    • 135 Days On Market

    Current Estimated Value $102,780

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    8320 Detour Rd, Denton, MD 21629
    • /14

      Est $397,458 Not Listed For Sale

      1211 Painted Fern Rd, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,238 Sq Ft
      • Built 2006
      1211 Painted Fern Rd, Denton, MD 21629

      Last Sold Summary

      • 2% Above List Price
      • $120/SF
      • 19 Days On Market
      • Last Sold Price $389,000
      • Sep 19, 2024

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /29

    $219,000 Pending

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft

    417 N Academy St, Greensboro, MD 21639

    Discover the charm of this delightful ranch-style home, perfectly nestled on a generous 0.26-acre lot. Built in 1993, this well-maintained residence boasts a warm and inviting atmosphere, ideal for creating lasting memories. With 936 square feet of thoughtfully designed living space, this home features two cozy bedrooms and a full bathroom, providing comfort and convenience for everyday living.

    Lawrence Doyle Long & Foster Real Estate, Inc.

    417 N Academy St, Greensboro, MD 21639
  • /33

    $350,000 Sold Sep 26, 2025

    24316 Auction Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,438 Sq Ft
    • Built 1975

    Last Sold Summary

    • $243/SF
    • 19 Days On Market

    Current Estimated Value $349,772

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    24316 Auction Rd, Preston, MD 21655
    • /42

      Est $368,298 Not Listed For Sale

      12041 Crouse Mill Rd, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,978 Sq Ft
      • Built 1994
      12041 Crouse Mill Rd, Ridgely, MD 21660

      Last Sold Summary

      • 9% Above List Price
      • $171/SF
      • 18 Days On Market
      • Last Sold Price $337,500
      • Apr 16, 2025

      Last Listing Agent Justin Brewer Baltimore Realty, LLC

Showing Results 161 - 200, Page 5 of 18

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