15,675

Caroline County, MD Homes

Section Image
  • 24749 Woods Dr, Denton, MD 21629
    24749 Woods Dr, Denton, MD 21629
    24749 Woods Dr, Denton, MD 21629
    /42

    $469,900

    • 4 Beds
    • 2.5 Baths
    • 2,550 Sq Ft

    24749 Woods Dr, Denton, MD 21629

    Beautifully maintained 4 bedroom, 2.5 bath Colonial set on a spacious lot just minutes from Denton and the newly opened Caroline Country Club. This inviting home features a comfortable, flowing layout featuring a gas fireplace, perfect for relaxing evenings or gatherings. The kitchen is conveniently located right off the main living area. The space showcases granite counter tops, stainless steel

    Peter Stark Benson & Mangold, LLC

    24749 Woods Dr, Denton, MD 21629
  • 24742 Tribbett Cir, Ridgely, MD 21660
    24742 Tribbett Cir, Ridgely, MD 21660
    24742 Tribbett Cir, Ridgely, MD 21660
    /38

    $565,000 Sold Mar 25, 2025

    24742 Tribbett Cir, Ridgely, MD 21660

    • 4 Beds
    • 2.5 Baths
    • 2,373 Sq Ft
    • Built 2025

    Last Sold Summary

    • $238/SF

    Current Estimated Value $597,285

    Last Listing Agent Kimberly Utz RE/MAX Executive

    24742 Tribbett Cir, Ridgely, MD 21660
    • 25766 Beauchamp Branch Rd, Denton, MD 21629
      25766 Beauchamp Branch Rd, Denton, MD 21629
      25766 Beauchamp Branch Rd, Denton, MD 21629
      /95

      Est $550,477 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,932 Sq Ft

      25766 Beauchamp Branch Rd, Denton, MD 21629

      25766 Beauchamp Branch Rd, Denton, MD 21629
  • 517 W Sunset Ave, Greensboro, MD 21639
    517 W Sunset Ave, Greensboro, MD 21639
    517 W Sunset Ave, Greensboro, MD 21639
    /4

    $345,000

    • Studio
    • 2,260 Sq Ft

    517 W Sunset Ave, Greensboro, MD 21639

    Three unit apartment building. Two 1bedroom apartments, one 2 bedroom. Fully leased with positive income to support expense and debt service

    Randy Staats Benson & Mangold, LLC

    517 W Sunset Ave, Greensboro, MD 21639
  • 333 Morning Glory Dr, Denton, MD 21629
    333 Morning Glory Dr, Denton, MD 21629
    333 Morning Glory Dr, Denton, MD 21629
    /30

    $390,000 Sold Jul 21, 2025

    333 Morning Glory Dr, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,475 Sq Ft
    • Built 2021

    Last Sold Summary

    • $158/SF
    • 21 Days On Market

    Current Estimated Value $417,490

    Last Listing Agent Danny Martin Keller Williams Flagship

    333 Morning Glory Dr, Denton, MD 21629
    • 6293 Statum Rd, Preston, MD 21655
      6293 Statum Rd, Preston, MD 21655
      6293 Statum Rd, Preston, MD 21655
      /52

      Est $637,386 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,429 Sq Ft

      6293 Statum Rd, Preston, MD 21655

      6293 Statum Rd, Preston, MD 21655
  • 318 Carter Ave, Denton, MD 21629
    318 Carter Ave, Denton, MD 21629
    318 Carter Ave, Denton, MD 21629
    /38

    $214,900

    • 2 Beds
    • 2 Baths
    • 606 Sq Ft

    318 Carter Ave, Denton, MD 21629

    This charming bungalow, fully renovated in 2020 and move-in ready, blends modern comfort with timeless appeal. Behind the classic covered front porch, an open layout offers two bedrooms and two full bathrooms on a single level. The living and kitchen area features a vaulted ceiling with recessed lighting, enhancing the sense of space and adding a clean, modern feel to this efficient floor

    Georgi Chauvin Benson & Mangold, LLC

    318 Carter Ave, Denton, MD 21629
  • 3 Oak St, Ridgely, MD 21660
    3 Oak St, Ridgely, MD 21660
    3 Oak St, Ridgely, MD 21660
    /45

    $308,000 Sold Apr 11, 2025

    3 Oak St, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,168 Sq Ft
    • Built 1995

    Last Sold Summary

    • $264/SF
    • 47 Days On Market

    Current Estimated Value $323,894

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    3 Oak St, Ridgely, MD 21660
    • 1150 Canvasback Ln, Denton, MD 21629
      1150 Canvasback Ln, Denton, MD 21629
      1150 Canvasback Ln, Denton, MD 21629
      /30

      Est $284,603 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,640 Sq Ft

      1150 Canvasback Ln, Denton, MD 21629

      1150 Canvasback Ln, Denton, MD 21629
  • 1005 Market St, Denton, MD 21629
    1005 Market St, Denton, MD 21629
    1005 Market St, Denton, MD 21629
    /3

    $135,000

    • Land
    • 0.69 Acre
    • $195,652 per Acre

    1005 Market St, Denton, MD 21629

    A Rare Opportunity to Purchase a General Commercial Lot located in Denton off the High Visibility Corners of Market & Gay St. A Multitude of permissible uses. Water and Sewer hook ups are available for additional fee. There are not any structures on this cleared .69 ac lot. A wonderful Opportunity for the Entrepreneur with a Vision....Hurry to snag this one...

    Barbara Beaudet Brenton Realty Group

    1005 Market St, Denton, MD 21629
  • 3880 Laurel Grove Rd, Federalsburg, MD 21632
    3880 Laurel Grove Rd, Federalsburg, MD 21632
    3880 Laurel Grove Rd, Federalsburg, MD 21632
    /33

    $320,000 Sold Jul 07, 2025

    3880 Laurel Grove Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft
    • Built 1940

    Last Sold Summary

    • $293/SF
    • 4 Days On Market

    Current Estimated Value $335,704

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

    3880 Laurel Grove Rd, Federalsburg, MD 21632
    • 24541 Hynson Rd, Federalsburg, MD 21632
      24541 Hynson Rd, Federalsburg, MD 21632
      24541 Hynson Rd, Federalsburg, MD 21632
      /15

      Est $249,158 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft

      24541 Hynson Rd, Federalsburg, MD 21632

      24541 Hynson Rd, Federalsburg, MD 21632
  • 26355 Marydel Rd, Marydel, MD 21649
    26355 Marydel Rd, Marydel, MD 21649
    26355 Marydel Rd, Marydel, MD 21649
    /4

    $155,000

    • 1 Bed
    • 1 Bath
    • 512 Sq Ft

    26355 Marydel Rd, Marydel, MD 21649

    House is of little to no value, existing well and septic. This house includes an additional parcel of 7 acres, tax id, 0601012428 for a total of 7.27 acres. Property being SOLD AS IS.

    George Thompson Long & Foster Real Estate, Inc.

    26355 Marydel Rd, Marydel, MD 21649
  • 0 Burnt Mill Rd Unit MDCM2005302, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2005302, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2005302, Ridgely, MD 21660
    /7

    $132,500 Sold Mar 19, 2025

    0 Burnt Mill Rd Unit MDCM2005302, Ridgely, MD 21660

    • Land
    • 3.62 Acres
    • $36,602 per Acre

    Last Sold Summary

    Last Listing Agent Gretchen Wichlinski Compass

    0 Burnt Mill Rd Unit MDCM2005302, Ridgely, MD 21660
    • 13389 Mason Branch Rd, Ridgely, MD 21660
      13389 Mason Branch Rd, Ridgely, MD 21660
      13389 Mason Branch Rd, Ridgely, MD 21660
      /49

      Est $805,768 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,244 Sq Ft

      13389 Mason Branch Rd, Ridgely, MD 21660

      13389 Mason Branch Rd, Ridgely, MD 21660
  • 0 Quail Ct Unit MDCM2006742, Greensboro, MD 21639
    0 Quail Ct Unit MDCM2006742, Greensboro, MD 21639
    0 Quail Ct Unit MDCM2006742, Greensboro, MD 21639
    /15

    $409,000 New Construction

    • 3 Beds
    • 2 Baths

    0 Quail Ct Unit MDCM2006742, Greensboro, MD 21639

    TBB....This beautifully designed rancher offers 3 bedrooms and 2 full baths with an open-concept floor plan and cathedral ceilings in the main living area. The builder includes a generous package of upgrades at no additional cost. Enjoy an oversized attached two-car garage and a rear deck perfect for outdoor living. Situated on a cleared 1-acre lot in a private rural setting, this home offers the

    Barbara Blosser Long & Foster Real Estate, Inc.

    0 Quail Ct Unit MDCM2006742, Greensboro, MD 21639
  • 22038 Church St, Hillsboro, MD 21641
    22038 Church St, Hillsboro, MD 21641
    22038 Church St, Hillsboro, MD 21641
    /33

    $191,000 Sold May 20, 2025

    22038 Church St, Hillsboro, MD 21641

    • Studio
    • 1,792 Sq Ft
    • Built 1950

    Last Sold Summary

    • $107/SF
    • 5 Days On Market

    Current Estimated Value $206,198

    Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

    22038 Church St, Hillsboro, MD 21641
    • 24251 Willow Pond Rd, Denton, MD 21629
      24251 Willow Pond Rd, Denton, MD 21629
      24251 Willow Pond Rd, Denton, MD 21629
      /71

      Est $621,970 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,813 Sq Ft

      24251 Willow Pond Rd, Denton, MD 21629

      24251 Willow Pond Rd, Denton, MD 21629
  • 24276 Asbury Dr, Denton, MD 21629
    24276 Asbury Dr, Denton, MD 21629
    24276 Asbury Dr, Denton, MD 21629
    /50

    $642,900

    • 4 Beds
    • 2.5 Baths
    • 2,920 Sq Ft

    24276 Asbury Dr, Denton, MD 21629

    Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Expansive lot sizes give you the privacy needed within a walkable neighborhood. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A large rear screened-in porch to watch the local wildlife opens onto extensive

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    24276 Asbury Dr, Denton, MD 21629
  • 14462 Poplar St, Goldsboro, MD 21636
    14462 Poplar St, Goldsboro, MD 21636
    14462 Poplar St, Goldsboro, MD 21636
    /48

    $460,000 Sold Jul 22, 2025

    14462 Poplar St, Goldsboro, MD 21636

    • 3 Beds
    • 2.5 Baths
    • 2,131 Sq Ft
    • Built 2003

    Last Sold Summary

    • $216/SF
    • 5 Days On Market

    Current Estimated Value $486,959

    Last Listing Agent Peter Mellor Wright Real Estate

    14462 Poplar St, Goldsboro, MD 21636
    • 1702 Cattail Commons Way, Denton, MD 21629
      1702 Cattail Commons Way, Denton, MD 21629
      1702 Cattail Commons Way, Denton, MD 21629
      /22

      Est $447,328 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,096 Sq Ft

      1702 Cattail Commons Way, Denton, MD 21629

      1702 Cattail Commons Way, Denton, MD 21629
  • 9571 Legion Rd, Denton, MD 21629
    9571 Legion Rd, Denton, MD 21629
    9571 Legion Rd, Denton, MD 21629
    /26

    $174,900 Under Contract

    • Land
    • 1.19 Acres
    • $146,975 per Acre

    9571 Legion Rd, Denton, MD 21629

    Rare 1.19-acre opportunity in the sought-after town of Denton. Zoned TR with newly expanded permitted uses, this versatile property offers the potential to subdivide into up to three lots, with connection fees already established for one lot. The property may also be suitable for a single residential homesite while maintaining a generous lot size. Permitted uses include two-family unit, duplex,

    Sharon Fisher RE/MAX Advantage Realty

    9571 Legion Rd, Denton, MD 21629
  • 11204 Academy St, Hillsboro, MD 21641
    11204 Academy St, Hillsboro, MD 21641
    11204 Academy St, Hillsboro, MD 21641
    /42

    $250,000 Sold Jun 06, 2025

    11204 Academy St, Hillsboro, MD 21641

    • 4 Beds
    • 1 Bath
    • 1,328 Sq Ft
    • Built 1800

    Last Sold Summary

    • $188/SF
    • 16 Days On Market

    Current Estimated Value $260,982

    Last Listing Agent Jennifer Chaney Chaney Homes, LLC

    11204 Academy St, Hillsboro, MD 21641
    • 120 Denton Rd, Federalsburg, MD 21632
      120 Denton Rd, Federalsburg, MD 21632
      120 Denton Rd, Federalsburg, MD 21632
      /5

      Est $58,667 Not Listed For Sale

      120 Denton Rd, Federalsburg, MD 21632

      120 Denton Rd, Federalsburg, MD 21632
  • 21405 Tanyard Rd, Preston, MD 21655
    21405 Tanyard Rd, Preston, MD 21655
    21405 Tanyard Rd, Preston, MD 21655
    /43

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 3,212 Sq Ft

    21405 Tanyard Rd, Preston, MD 21655

    Peaceful Country Living on 3.2 Acres – Recently Renovated Home with Expansive Pole Barn! Welcome to 21405 Tanyard Rd in Preston, MD – where modern updates meet serene country living. This beautifully renovated 3-bedroom, 3-bath home sits on 3.2 acres—perfect for gardening, raising animals, or simply enjoying wide-open space and quiet surroundings. Step inside to find a bright, freshly updated

    Justin Pokrywka Taylor Properties

    21405 Tanyard Rd, Preston, MD 21655
  • 122 Mill St, Greensboro, MD 21639
    122 Mill St, Greensboro, MD 21639
    122 Mill St, Greensboro, MD 21639
    /57

    $280,000 Sold Nov 26, 2025

    122 Mill St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,104 Sq Ft
    • Built 2002

    Last Sold Summary

    • $254/SF
    • 48 Days On Market

    Last Listing Agent Carolyn Buchleitner Berkshire Hathaway HomeServices PenFed Realty

    122 Mill St, Greensboro, MD 21639
    • 4191 Harmony Rd, Preston, MD 21655
      4191 Harmony Rd, Preston, MD 21655
      4191 Harmony Rd, Preston, MD 21655
      /18

      Est $535,097 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,196 Sq Ft

      4191 Harmony Rd, Preston, MD 21655

      4191 Harmony Rd, Preston, MD 21655
  • 5940 Noble Rd, Federalsburg, MD 21632
    5940 Noble Rd, Federalsburg, MD 21632
    /2

    $249,900

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    5940 Noble Rd, Federalsburg, MD 21632

    Welcome to peaceful rural living just minutes from town conveniences in Federalsburg, MD. This well-situated single-story ranch home offers functional and accessible living across one level, perfectly suited for first-time buyers, downsizers, or those seeking country comfort with ample outdoor space. You'll have nearly 3 acres of land — great for gardening, recreation, or possbly a future

    Holly Anderson Long & Foster Real Estate, Inc.

    5940 Noble Rd, Federalsburg, MD 21632
  • 524 Denton Rd, Federalsburg, MD 21632
    524 Denton Rd, Federalsburg, MD 21632
    524 Denton Rd, Federalsburg, MD 21632
    /24

    $212,000 Sold Jul 09, 2025

    524 Denton Rd, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1920

    Last Sold Summary

    • $245/SF
    • 9 Days On Market

    Current Estimated Value $212,361

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

    524 Denton Rd, Federalsburg, MD 21632
    • 1306 Chesapeake Dr, Denton, MD 21629
      1306 Chesapeake Dr, Denton, MD 21629
      1306 Chesapeake Dr, Denton, MD 21629
      /13

      Est $351,928 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,654 Sq Ft

      1306 Chesapeake Dr, Denton, MD 21629

      1306 Chesapeake Dr, Denton, MD 21629
  • 7904 Clark Rd, Denton, MD 21629
    7904 Clark Rd, Denton, MD 21629
    7904 Clark Rd, Denton, MD 21629
    /71

    $1,099,999 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 3,242 Sq Ft

    7904 Clark Rd, Denton, MD 21629

    This ±45-acre previously certified organic farm is located just south of Denton and offers a well-rounded combination of productive farmland, agricultural infrastructure, and residential living. The property includes approximately ±41 acres of tillable ground equipped with a subsurface irrigation system fed by six on-site wells, providing efficient and reliable water delivery for a wide range of

    Jesse Highling The Land Group

    7904 Clark Rd, Denton, MD 21629
  • 502 W Sunset Ave, Greensboro, MD 21639
    502 W Sunset Ave, Greensboro, MD 21639
    502 W Sunset Ave, Greensboro, MD 21639
    /12

    $176,400 Sold May 23, 2025

    502 W Sunset Ave, Greensboro, MD 21639

    • 3 Beds
    • 1.5 Baths
    • 1,155 Sq Ft
    • Built 1948

    Last Sold Summary

    • $153/SF
    • 223 Days On Market

    Current Estimated Value $209,887

    Last Listing Agent Pamela Geib Long & Foster Real Estate, Inc.

    502 W Sunset Ave, Greensboro, MD 21639
    • 5576 Harmony Woods Dr, Preston, MD 21655
      5576 Harmony Woods Dr, Preston, MD 21655
      5576 Harmony Woods Dr, Preston, MD 21655
      /27

      Est $427,325 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft

      5576 Harmony Woods Dr, Preston, MD 21655

      5576 Harmony Woods Dr, Preston, MD 21655
  • 6401 Laurel Grove Rd, Denton, MD 21629
    6401 Laurel Grove Rd, Denton, MD 21629
    6401 Laurel Grove Rd, Denton, MD 21629
    /23

    $1,200,000 Under Contract

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

    6401 Laurel Grove Rd, Denton, MD 21629

    52.08 acres with 3 bedroom 2 bath home and large Pole Barn 48 x 110 machine shed. More pictures will be added soon.

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    6401 Laurel Grove Rd, Denton, MD 21629
  • 8816 Dorothy Ln, Denton, MD 21629
    8816 Dorothy Ln, Denton, MD 21629
    8816 Dorothy Ln, Denton, MD 21629
    /71

    $940,000 Sold Nov 17, 2025

    8816 Dorothy Ln, Denton, MD 21629

    • 4 Beds
    • 3.5 Baths
    • 4,092 Sq Ft
    • Built 1989

    Last Sold Summary

    • $230/SF
    • 166 Days On Market

    Last Listing Agent Dustin Parker The Parker Group

    8816 Dorothy Ln, Denton, MD 21629
    • 27105 River Bridge Rd, Henderson, MD 21640
      27105 River Bridge Rd, Henderson, MD 21640
      27105 River Bridge Rd, Henderson, MD 21640
      /6

      Est $69,121 Not Listed For Sale

      27105 River Bridge Rd, Henderson, MD 21640

      27105 River Bridge Rd, Henderson, MD 21640
  • 0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660
    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660
    /2

    $32,500

    • Land
    • 0.69 Acre
    • $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
  • 113 Boyce Mill Rd, Greensboro, MD 21639
    113 Boyce Mill Rd, Greensboro, MD 21639
    113 Boyce Mill Rd, Greensboro, MD 21639
    /25

    $235,000 Sold Oct 30, 2025

    113 Boyce Mill Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 2007

    Last Sold Summary

    • $196/SF
    • 18 Days On Market

    Current Estimated Value $247,010

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    113 Boyce Mill Rd, Greensboro, MD 21639
    • 26062 Holly Ln, Greensboro, MD 21639
      26062 Holly Ln, Greensboro, MD 21639
      26062 Holly Ln, Greensboro, MD 21639
      /32

      Est $406,608 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,798 Sq Ft

      26062 Holly Ln, Greensboro, MD 21639

      26062 Holly Ln, Greensboro, MD 21639
  • 12618 Knife Box Rd, Greensboro, MD 21639
    12618 Knife Box Rd, Greensboro, MD 21639
    12618 Knife Box Rd, Greensboro, MD 21639
    /49

    $797,500 Under Contract

    • 3 Beds
    • 2 Baths
    • 2,342 Sq Ft

    12618 Knife Box Rd, Greensboro, MD 21639

    Custom home built in 2007, this home features a large eat in kitchen, a lovely screened porch over looking the park like property. Living room featuring a fireplace, and tray ceiling. to add another cozy feature. Hard wood flooring through out the living space gives that warm welcoming vibe. The property has the potential to be off the grid, the geothermal system is the basis., and a wood stove

    Kat Thompson Benson & Mangold, LLC.

    12618 Knife Box Rd, Greensboro, MD 21639

Showing Results 321 - 360, Page 9 of 18

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