15,577

Caroline County, MD Homes

Section Image Section Image
  • /36

    $325,000

    Sold Sep 26, 2025

    6315 Harmony Rd, Preston, MD 21655

    • 3 Beds
    • 3 Baths
    • 2,016 Sq Ft
    • Built 1994

    Last Sold Summary

    • $161/SF
    • 28 Days On Market

    Current Estimated Value $337,847

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    6315 Harmony Rd, Preston, MD 21655
    • /33

      Est $323,309

      Not Listed For Sale

      7881 Dyer Rd, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 1,961 Sq Ft
      • Built 1972
      7881 Dyer Rd, Denton, MD 21629

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Douglas Reyes Smart Realty, LLC

  • /28

    $419,000

    • 4 Beds
    • 2.5 Baths
    • 2,256 Sq Ft

    1101 Trice Meadows Cir, Denton, MD 21629

    Almost new and absolutely gorgeous! Built in 2023, this beautiful 4-bedroom, 2.5-bath home offers a fabulous floor plan designed for comfortable everyday living and easy entertaining.Lovely luxury vinyl tile flooring flows throughout the main level and leads to the heart of the home—the family room, open to the kitchen. The kitchen is upgraded and features granite countertops, stainless

    Jimmy White Long & Foster Real Estate, Inc.

    1101 Trice Meadows Cir, Denton, MD 21629
  • /20

    $272,490

    Sold Jun 10, 2026

    127 Hobbs St, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $257/SF
    • 83 Days On Market

    D.R. Horton Kinnamon Meadows

    127 Hobbs St, Greensboro, MD 21639
    • /38

      Est $277,326

      Not Listed For Sale

      1606 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 3.5 Baths
      • 2,268 Sq Ft
      • Built 2006
      1606 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

  • /19

    $850,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 2,320 Sq Ft

    6401 Laurel Grove Rd, Denton, MD 21629

    Nestled on an expansive 52.08-acre estate, this stunning ranch-style farm offers a harmonious blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle in a serene rural setting. The property boasts a traditional architectural design, complemented by aluminum siding that enhances its timeless appeal. Step inside to discover a thoughtfully designed interior that exudes

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    6401 Laurel Grove Rd, Denton, MD 21629
  • /5

    $201,000

    Sold Dec 19, 2025

    6561 Bell Creek Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1915

    Last Sold Summary

    • $149/SF
    • 14 Days On Market

    Current Estimated Value $226,318

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

    6561 Bell Creek Rd, Preston, MD 21655
    • /38

      Est $244,002

      Not Listed For Sale

      26875 Barclay Rd, Marydel, MD 21649

      • 3 Beds
      • 1 Bath
      • 1,404 Sq Ft
      • Built 1951
      26875 Barclay Rd, Marydel, MD 21649

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

  • /2

    $32,500

    • Land
    • 30,056 Sq Ft
    • $47,101 per Acre

    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660

    Just next to the quaint town of Ridgely, this .69 acre lot also comes with a bonus lot highlighted in photos. Buy and hold as an investment or see if you can perc.

    Michael Rosendale Rosendale Realty

    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660
  • /2

    $273,990

    Sold Jan 15, 2026

    129 Hobbs St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 1% Below List Price
    • $232/SF
    • 14 Days On Market

    D.R. Horton Kinnamon Meadows

    129 Hobbs St, Greensboro, MD 21639
    • /73

      Est $670,746

      Not Listed For Sale

      20810 Frazier Point Ln, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 2,226 Sq Ft
      • Built 1970
      20810 Frazier Point Ln, Preston, MD 21655

      Last Sold Summary

      • 229 Days On Market

      Last Listing Agent Barbara McCaffrey Redfin Corp

  • /7

    $749,900

    Coming Soon Sep 30
    • 4 Beds
    • 3.5 Baths
    • 5,303 Sq Ft

    4517 Smithville Rd, Federalsburg, MD 21632

    Professional photos and detailed description coming soon!

    Shane Slacum LPT Realty, LLC

    4517 Smithville Rd, Federalsburg, MD 21632
  • /66

    $549,000

    Sold Aug 12, 2026

    3410 Seaman Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 1,988 Sq Ft
    • Built 1989

    Last Sold Summary

    • 2% Above List Price
    • $276/SF
    • 4 Days On Market

    Current Estimated Value $497,580

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

    3410 Seaman Rd, Preston, MD 21655
    • /28

      Est $284,395

      Not Listed For Sale

      1614 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,244 Sq Ft
      • Built 2006
      1614 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Marcy Gaines CENTURY 21 New Millennium

  • /20

    $329,900

    • 3 Beds
    • 2.5 Baths
    • 1,890 Sq Ft

    117 Sunset Blvd, Preston, MD 21655

    Welcome to 117 Sunset, a spacious one-level ranch offering 1,890 square feet, three bedrooms, two and a half baths, and plenty of character inside and out. The standout living area immediately draws your eye with its soaring vaulted wood-plank ceiling, exposed beams, abundant natural light, and impressive full brick fireplace wall, creating a warm gathering space unlike the typical

    Bevia Patrick Keller Williams Flagship

    117 Sunset Blvd, Preston, MD 21655
  • /59

    $385,000

    Sold Nov 07, 2025

    502 N Academy St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 2,378 Sq Ft
    • Built 1960

    Last Sold Summary

    • $162/SF
    • 105 Days On Market

    Current Estimated Value $379,766

    Last Listing Agent Chris Rosendale CR Realty

    502 N Academy St, Greensboro, MD 21639
    • /31

      Est $230,567

      Not Listed For Sale

      3427 Holland Dr, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,091 Sq Ft
      • Built 1994
      3427 Holland Dr, Federalsburg, MD 21632

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Matthew Olson EXP Realty, LLC

  • /69

    $740,000

    Under Contract
    • 5 Beds
    • 4 Baths
    • 5,286 Sq Ft

    24764 Pealiquor Rd, Denton, MD 21629

    Back on the Market at No Fault of the Seller! Welcome to Timeless Elegance Meets Modern Comfort. Step inside this stunning Cape Cod residence and immediately feel at home. A gracious foyer framed by classic columns invites you into a luminous interior that effortlessly blends traditional charm with modern open‑concept living. To your right, a versatile flex room offers the perfect space for a

    Dustin Parker The Parker Group

    24764 Pealiquor Rd, Denton, MD 21629
  • /2

    $90,000

    Sold Apr 07, 2026

    103 S Main St, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 2,116 Sq Ft
    • Built 1890

    Last Sold Summary

    • 5% Below List Price
    • $43/SF
    • 18 Days On Market

    Last Listing Agent Valerie Brown Coldwell Banker Realty

    103 S Main St, Federalsburg, MD 21632
    • /13

      Est $273,544

      Not Listed For Sale

      25 Greenridge Ave, Ridgely, MD 21660

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1993
      25 Greenridge Ave, Ridgely, MD 21660

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Marti McGinty Chesapeake Real Estate Associates, LLC

  • /62

    $630,000

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,725 Sq Ft

    26927 Boyce Mill Rd, Greensboro, MD 21639

    Nestled on 5 beautiful acres, this spacious 4-bedroom, 3.5-bath home offers the perfect blend of privacy, comfort, and country living. Approximately 1.8 acres are wooded, providing a peaceful backdrop and frequent visits from local wildlife, while the remaining acreage is cleared and ideal for outdoor enjoyment.The inviting front porch overlooks the private rural setting, while the interior

    Barbara Blosser Long & Foster Real Estate, Inc.

    26927 Boyce Mill Rd, Greensboro, MD 21639
  • /18

    $75,000

    Sold Jun 01, 2026

    215 Academy Ave, Federalsburg, MD 21632

    • 2 Beds
    • 2 Baths
    • 1,520 Sq Ft
    • Built 1903

    Last Sold Summary

    • 21% Below List Price
    • $49/SF
    • 40 Days On Market

    Current Estimated Value $125,667

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

    215 Academy Ave, Federalsburg, MD 21632
    • /56

      Est $403,156

      Not Listed For Sale

      12710 Greensboro Rd, Greensboro, MD 21639

      • 3 Beds
      • 2.5 Baths
      • 1,472 Sq Ft
      • Built 1950
      12710 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Scott Judy Coldwell Banker Waterman Realty

  • /4

    $21,000

    $14K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft

    204 Academy Ave, Federalsburg, MD 21632

    Investor special! This property is being sold AS-IS and is priced for land value or a full renovation. The existing structure requires extensive repairs or complete tear-down—ideal for experienced builders, contractors, or savvy investors looking for a project. Buyer to verify zoning, permits, potential use. Buyer Broker/Agent and/or Buyer must do their own due diligence to verify if the existing

    Mike Dunn Keller Williams Realty Delmarva

    204 Academy Ave, Federalsburg, MD 21632
  • /4

    $235,000

    Sold Aug 25, 2026

    21579 Tanyard Rd, Preston, MD 21655

    • 4 Beds
    • 2 Baths
    • 1,816 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Above List Price
    • $129/SF
    • 4 Days On Market

    Current Estimated Value $335,771

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    21579 Tanyard Rd, Preston, MD 21655
    • /41

      Est $282,122

      Not Listed For Sale

      1915 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,640 Sq Ft
      • Built 2006
      1915 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

  • /2

    $59,900

    • Land
    • 1 Acre
    • $59,900 per Acre

    27286 Willin Ln, Federalsburg, MD 21632

    Private 1-acre wooded lot with deeded access via a dirt road. Enjoy a secluded setting surrounded by nature, perfect for those looking to get away from it all. Great opportunity for a future homesite or recreational use (subject to county approvals). Motivated seller—bring all reasonable offers!

    Janet Todd Harlan C. Williams Co.

    27286 Willin Ln, Federalsburg, MD 21632
  • /5

    $295,000

    Sold Jan 30, 2026

    3376 Jefferson Pond Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2025

    Last Sold Summary

    • $219/SF
    • 182 Days On Market

    Last Listing Agent Amy Herr Keller Williams Realty

    3376 Jefferson Pond Rd, Federalsburg, MD 21632
    • /15

      Est $328,013

      Not Listed For Sale

      8888 Harmony Rd, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1910
      8888 Harmony Rd, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Preda Mendez-Lopez Realty One Group Performance, LLC

  • /13

    $102,500

    $7K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    4471 Harmony Rd, Preston, MD 21655

    Discover the potential in this ranch-style home situated on a spacious lot in Caroline County. This property is ready for renovation and offers a great opportunity to update and customize to your vision. Major improvements have already been completed, including a newer roof and updated windows, providing a solid starting point for your renovation plans. The home is served by a private well and

    Norman Domingo XRealty.NET LLC

    4471 Harmony Rd, Preston, MD 21655
  • /2

    $269,990

    Sold Oct 13, 2025

    113 Parkland Rd, Greensboro, MD 21639

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

    Move in Ready Sold Summary

    • $221/SF
    • 19 Days On Market

    D.R. Horton Kinnamon Meadows

    113 Parkland Rd, Greensboro, MD 21639
    • /31

      Est $382,435

      Not Listed For Sale

      25797 Spring Branch Dr, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 1998
      25797 Spring Branch Dr, Greensboro, MD 21639

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Rick Parreco RE/MAX Executive

  • /47

    $755,000

    • 3 Beds
    • 2 Baths
    • 2,504 Sq Ft

    3769 Bradley Rd, Federalsburg, MD 21632

    This is your farmette dream come true! This beautiful 3 bed, 2 full bath home is situated on 6+ acres of partially fenced in land, has a barn with a tack room, a large screened-in back porch, a 2 car garage and an in-ground saltwater pool. The barn features 3 stalls, a hay loft with elevator, washroom, a tack room with a closet and shelves for storage. The water to the barn is sourced from a 290

    Sarah Robins Coldwell Banker Realty

    3769 Bradley Rd, Federalsburg, MD 21632
  • /25

    $260,000

    Sold Oct 30, 2025

    1904 Blue Heron Dr, Denton, MD 21629

    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft
    • Built 2007

    Last Sold Summary

    • $98/SF
    • 61 Days On Market

    Current Estimated Value $265,311

    Last Listing Agent Ralph Harvey ListWithFreedom.com

    1904 Blue Heron Dr, Denton, MD 21629
    • /26

      Est $230,483

      Not Listed For Sale

      1510 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,692 Sq Ft
      • Built 2004
      1510 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Dan Foster Long & Foster Real Estate, Inc.

  • /30

    $299,000

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

    101 Parkland Rd, Greensboro, MD 21639

    Just a few months old and ready for you to move right in! This beautifully maintained 3-bedroom, 2-bath rancher offers the ease of one-level living with a bright, open layout and the benefits of a nearly brand-new home—without the wait.The spacious kitchen and living areas flow seamlessly together, creating an inviting space for everyday living and entertaining. The seller even added a

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    101 Parkland Rd, Greensboro, MD 21639
  • /28

    $215,990

    Sold Nov 26, 2025

    100 Riverwalk Terrace, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2024

    Last Sold Summary

    • $158/SF
    • 34 Days On Market

    Current Estimated Value $215,667

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

    100 Riverwalk Terrace, Federalsburg, MD 21632
    • /80

      Est $400,633

      Not Listed For Sale

      24300 Robins Creek Rd, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,624 Sq Ft
      • Built 1979
      24300 Robins Creek Rd, Preston, MD 21655

      Last Sold Summary

      • 127 Days On Market

      Last Listing Agent Cheryl Jersey-Lecourt Long & Foster Real Estate, Inc.

  • /25

    $74,900

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    21182 March Creek Road E-10 Rd, Preston, MD 21655

    The home is located in between Easton and Preston, very close to Easton major shopping centers. This home offers 3 bedroom 2 full baths, and a large living room, Very private setting. For an application go to tenantrelationships@rentstackhouse.com, For question call 855-548-3642. You will get an AI recepticent , ask for Cecelia for billing questions and Brandis for application questions

    Denis Gasper Benson & Mangold, LLC

    21182 March Creek Road E-10 Rd, Preston, MD 21655
  • /57

    $950,000

    Sold Jul 10, 2026

    7805 Dyer Rd, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Built 2022

    Last Sold Summary

    • $528/SF
    • 2 Days On Market

    Current Estimated Value $518,415

    Last Listing Agent Brody Sergent Northrop Realty

    7805 Dyer Rd, Denton, MD 21629

Showing Results 441 - 480, Page 12 of 18

How to Buy a Home How to Finance a Home How to Sell a Home