15,709

Caroline County, MD Homes

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  • /25

    $465,000 Under Contract

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

    22889 Hog Creek Rd, Preston, MD 21655

    Spacious 4-bedroom, 2 full and 1 half bath home located in desirable Preston, MD. This property offers the perfect blend of comfort and functionality, featuring a 3-car heated garage, central air, and a heat pump for year-round efficiency. Enjoy outdoor living with a deck complete with awning, a large yard supported by an underground irrigation system, and an additional shed for storage. Inside,

    Katie Moore Coldwell Banker Chesapeake Real Estate Company

    22889 Hog Creek Rd, Preston, MD 21655
  • /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 $309,288

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    504 Pintail St, Greensboro, MD 21639
    • /5

      Est $48,273 Not Listed For Sale

      26302 Sennett Rd, Denton, MD 21629

      26302 Sennett Rd, Denton, MD 21629

      Last Sold Summary

      • 29% Above List Price
      • 233 Days On Market
      • Last Sold Price $37,500
      • Oct 26, 2023

      Last Listing Agent Michelle Anderson Coldwell Banker Premier - Seaford

  • /25

    $350,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,160 Sq Ft

    22650 Tanyard Rd, Preston, MD 21655

    Looking for room to breathe and space for your projects? This charming brick rancher offers exactly that! Over 3 acres close to Preston, Easton and all mid-shore locations. The home features hardwood floors, updated kitchen, drywalled ceilings, new lighting and a new HVAC system providing heat and air. The full basement offers room to expand and more living space. Fantastic yard - mostly fenced.

    Valerie Brown Coldwell Banker Realty

    22650 Tanyard 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
    • /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 Sold Price $132,500
      • Mar 19, 2025

      Last Listing Agent Gretchen Wichlinski Compass

  • /18

    $350,000

    • 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
  • /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 $929,441

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    3069 Choptank Rd, Preston, MD 21655
    • /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 Sold Price $132,500
      • Mar 19, 2025

      Last Listing Agent Gretchen Wichlinski Compass

  • /47

    $674,999

    • 4 Beds
    • 2.5 Baths
    • 2,576 Sq Ft

    4757 Long Swamp Rd, Federalsburg, MD 21632

    Welcome to 4757 Long Swamp Rd, a truly unique property in Federalsburg, MD, offering the perfect blend of equestrian facilities and comfortable country living on 7.04 acres. This well-maintained estate is ready for you and your horses, with no restrictions on property use and the added flexibility for the land to be subdivided. The grounds feature expansive pastures secured by electric fencing, a

    Billy Mister Keller Williams Realty

    4757 Long Swamp Rd, 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
    • /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 Sold Price $249,900
      • Mar 06, 2025

      Last Listing Agent William Norris Select Land & Homes, LLC

  • /28

    $368,999 New Construction

    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft

    210 W 2nd St, Ridgely, MD 21660

    Brand new. Zero honey-do list. Full peace of mind. Welcome to this newly constructed 4-bedroom, 2-bath home in Ridgely, where modern design meets small-town charm. If you’ve been waiting for that fresh-start feeling — this is it. Step inside to a bright, open layout designed for real life. The spacious living area flows seamlessly into the kitchen and dining space, creating the perfect setup for

    Kenneth Jester Coldwell Banker Realty

    210 W 2nd St, Ridgely, MD 21660
  • /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 $315,342

    Last Listing Agent Brooke Tephabock LPT Realty, LLC

    3622 Choptank Rd, Preston, MD 21655
    • /27

      Est $224,259 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

      • 7% Above List Price
      • $154/SF
      • 49 Days On Market
      • Last Sold Price $209,990
      • Mar 26, 2025

      Last Listing Agent Kathleen Cassidy DRH Realty Capital, LLC.

  • /55

    $635,000

    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    11142 Log Cabin Rd, Denton, MD 21629

    Welcome to 11142 Log Cabin Road! This unique property offers the perfect combination of residential living and valuable commercial space, all on one expansive, 4.53 acre lot. This beautiful colonial-style home has great curb appeal with its classic look, neatly trimmed landscaping, and a spacious front yard shaded by mature trees. The main home spans over 2,700 square feet and features four

    Courtney Gallagher Keller Williams Realty Central-Delaware

    11142 Log Cabin Rd, Denton, MD 21629
  • /2

    $20,500 Sold Apr 24, 2026

    205 Park Ave, Federalsburg, MD 21632

    • Land
    • 6,534 Sq Ft
    • $136,667 per Acre

    Last Sold Summary

    • 25% Below List Price
    • 18 Days On Market

    Current Estimated Value $108,398

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

    205 Park Ave, Federalsburg, MD 21632
    • /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

      • $1,055/SF
      • 7 Days On Market
      • Last Sold Price $2,000,000
      • Mar 21, 2025

      Last Listing Agent BRIAN MORRIS The Land Group

  • /65

    $599,000

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft

    322 Deep Shore Rd, Denton, MD 21629

    This home is anything but ordinary. Thoughtfully built by the current owners in 1982, the property showcases true craftsmanship with structural beams hewn from timber sourced right from the land itself. The main living space is situated on the second floor, offering a bright, airy layout and sweeping views across 13 picturesque acres. The first floor provides incredible flexibility—ideal for

    Connie Loveland Benson & Mangold, LLC

    322 Deep Shore Rd, Denton, MD 21629
  • /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
    • /27

      Est $232,029 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

      • 5% Above List Price
      • $161/SF
      • 47 Days On Market
      • Last Sold Price $219,990
      • Mar 13, 2025

      Last Listing Agent Kathleen Cassidy DRH Realty Capital, LLC.

  • /29

    $319,000

    • 2 Beds
    • 1.5 Baths
    • 2,017 Sq Ft

    211 Bloomingdale Ave, Federalsburg, MD 21632

    Welcome to 211 Bloomingdale Ave. This custom‐built Brick Williamsburg‐style colonial showcases true craftsmanship, featuring beautiful hardwood floors throughout, custom built‐ins, and detailed moldings. The spacious living room offers an inviting wood‐burning fireplace, while the large great room with its vaulted ceiling provides flexible living space and could easily be converted into a third

    Jana Meredith Meredith Fine Properties

    211 Bloomingdale Ave, Federalsburg, MD 21632
  • /16

    $265,000 Sold Jul 31, 2025

    17 Greenridge Ave, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,136 Sq Ft
    • Built 1991

    Last Sold Summary

    • $233/SF
    • 7 Days On Market

    Current Estimated Value $281,519

    Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

    17 Greenridge Ave, Ridgely, MD 21660
    • /28

      Est $231,319 Not Listed For Sale

      115 Riverwalk Terrace, Federalsburg, MD 21632

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

      Last Sold Summary

      • 5% Above List Price
      • $161/SF
      • 66 Days On Market
      • Last Sold Price $219,990
      • Mar 24, 2025

      Last Listing Agent Kathleen Cassidy DRH Realty Capital, LLC.

  • /27

    $334,000

    • 3 Beds
    • 1.5 Baths
    • 1,622 Sq Ft

    207 S 7th St, Denton, MD 21629

    3BR, 1.5BA home on LARGE in town lot featuring Corian countertops, hardwood floors and built-in bookshelves. Enjoy a welcoming front porch and screened breezeway connecting a 2 car attached garage with additional lean-to storage. Roof replaced 2021. Full Walkout Dry basement with French drain and sump pump. Convenient in town location close to local amenities, all that is missing is your car in

    Amy Betts Coldwell Banker Realty

    207 S 7th St, Denton, MD 21629
  • /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 $330,883

    Last Listing Agent Michael Bozek Michael J. Bozek

    614 Market St, Denton, MD 21629
    • /8

      Not Listed For Sale

      0 Houston Branch Rd Unit MDCM2005056, Federalsburg, MD 21632

      0 Houston Branch Rd Unit MDCM2005056, Federalsburg, MD 21632

      Last Sold Summary

      • 20 Days On Market
      • Last Sold Price $2,950,000
      • Mar 13, 2025

      Last Listing Agent Benjamin Alder The Land Group

  • /54

    $395,000

    • 4 Beds
    • 2 Baths
    • 1,692 Sq Ft

    12658 Oakland Rd, Ridgely, MD 21660

    Right on the outskirts of the Historic Town of Ridgely Maryland you will find this fully remodeled 4 bedroom rancher on a beautiful acre of land. A fenced backyard perfect for your pets and or your small farm animal dreams! Plenty of room for a kitchen garden too! Inside you will find a recently remodeled open concept kitchen with large island that makes for a great workspace & great gatherings!

    John Cary Rosendale Realty

    12658 Oakland Rd, Ridgely, MD 21660
  • /20

    $266,990 Sold Oct 10, 2025

    120 Parkland Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $252/SF
    • 24 Days On Market

    D.R. Horton Kinnamon Meadows

    120 Parkland Rd, Greensboro, MD 21639
    • /79

      Est $505,557 Not Listed For Sale

      13056 Hog Lot Rd, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 2008
      13056 Hog Lot Rd, Ridgely, MD 21660

      Last Sold Summary

      • 19% Below List Price
      • $413/SF
      • 0 Days On Market
      • Last Sold Price $625,000
      • Jul 31, 2024

      Last Listing Agent Michele Williams Redfin Corp

  • /31

    $329,900

    • 3 Beds
    • 2 Baths
    • 1,748 Sq Ft

    10280 Log Cabin Rd, Denton, MD 21629

    The Joy of One level Living! This Rancher comes with 3 Nice size Bedrooms and 2 Full Baths. Eat-in Kitchen with Plenty of Storage. Family Room with FirePlace, Living Room, Enclosed Sunroom and a Seperate Laundry Room. Outdoors features just over 2 Acres! Large Patio for entertaining, POND, with Gazebo, Shed and a nice level lot with Mature trees. Home could use some updating but offers good bones

    Kathleen Brenton Brenton Realty Group

    10280 Log Cabin Rd, Denton, MD 21629
  • 25999 Fox Grape Rd, Greensboro, MD 21639

    $379,000 Sold Mar 20, 2026

    25999 Fox Grape Rd, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 1987

    Last Sold Summary

    • $211/SF
    • 70 Days On Market

    Current Estimated Value $378,810

    Last Listing Agent Amy Betts Coldwell Banker Realty

    25999 Fox Grape Rd, Greensboro, MD 21639
    • /24

      Not Listed For Sale

      123/123A/125 123A/12 N Main St, Federalsburg, MD 21632

      • Studio
      • 3,926 Sq Ft
      • Built 1895
      123/123A/125 123A/12 N Main St, Federalsburg, MD 21632

      Last Sold Summary

      • $45/SF
      • 125 Days On Market
      • Last Sold Price $175,000
      • Apr 11, 2025

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

  • /27

    $339,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    208 Oriole Ave, Ridgely, MD 21660

    Charming 3-bedroom, 2-bath rancher located in Ridgely! Inside, you’ll find comfortable one-level living with a functional open layout connecting the living room and kitchen, complete with stainless steel appliances. The spacious primary suite features a large en-suite bath and private doors leading directly to the backyard deck. Two additional generously sized bedrooms provide plenty of space for

    Alicia Gannon Dulin Benson & Mangold, LLC

    208 Oriole Ave, Ridgely, MD 21660
  • /46

    $348,000 Sold Oct 14, 2025

    22490 Ash Blvd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 2001

    Last Sold Summary

    • $188/SF
    • 22 Days On Market

    Last Listing Agent Kathryn Tennant Douglas Realty, LLC

    22490 Ash Blvd, Preston, MD 21655
    • /7

      Not Listed For Sale

      0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660

      0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660

      Last Sold Summary

      • 124 Days On Market
      • Last Sold Price $120,000
      • Mar 20, 2025

      Last Listing Agent Stephan Strothe Washington Fine Properties, LLC

  • /64

    $399,000

    • 4 Beds
    • 3 Baths
    • 1,680 Sq Ft

    8578 Tuckahoe Rd, Denton, MD 21629

    This property boasts with a 4 bedroom 3 full bathroom cape cod on a 1 acre lot in a beautiful wide open country setting! Fresh paint throughout the entire house, new refrigerator, new oven, new dryer AND new HVAC! All of the hard work has been done! Minutes to Denton or Easton. Move in ready!

    Megan Rosendale Rosendale Realty

    8578 Tuckahoe Rd, Denton, MD 21629
  • /35

    $239,900 Sold Mar 31, 2026

    515 Vaughn Ave, Greensboro, MD 21639

    • 4 Beds
    • 2.5 Baths
    • 1,756 Sq Ft
    • Built 2004

    Last Sold Summary

    • 4% Below List Price
    • $137/SF
    • 27 Days On Market

    Current Estimated Value $242,591

    Last Listing Agent Chad Muse KD Realty Inc

    515 Vaughn Ave, Greensboro, MD 21639
    • /5

      Est $98,945 Not Listed For Sale

      21373 Dover Bridge Rd, Preston, MD 21655

      • Built 1890
      21373 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • $70/SF
      • 16 Days On Market
      • Last Sold Price $99,000
      • Dec 27, 2024

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  • /26

    $369,000

    • 3 Beds
    • 2 Baths
    • 2,412 Sq Ft

    1302 Trice Meadows Cir, Denton, MD 21629

    Lovely Raised Rancher consisting of 2,412 square feet of living with the main level having 3 bedrooms, 2 bathrooms, office/den, living room, kitchen and laundry area with a split floor plan of the bedrooms and the owner's suite on the opposite end of house. No worries about parking your vehicles with this nice 2 car attached garage and on street parking. Additionally, the second floor 52x15 bonus

    George Thompson Long & Foster Real Estate, Inc.

    1302 Trice Meadows Cir, Denton, MD 21629

Showing Results 81 - 120, Page 3 of 18

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