15,671

Caroline County, MD Homes

Section Image Section Image
  • 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 $592,435

    Last Listing Agent Kimberly Utz RE/MAX Executive

    24742 Tribbett Cir, Ridgely, MD 21660
    • 319 Kerr Ave, Denton, MD 21629
      319 Kerr Ave, Denton, MD 21629
      319 Kerr Ave, Denton, MD 21629
      /27

      Est $278,534 Not Listed For Sale

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

      319 Kerr Ave, Denton, MD 21629

      319 Kerr Ave, Denton, MD 21629
  • 129 Hobbs St, Greensboro, MD 21639

    $276,990 New Construction

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

    129 Hobbs St, Greensboro, MD 21639

    Discover 129 Hobbs Street, a new home under-construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms, two bathrooms, and a two-car driveway. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the

    D.R. Horton Builder
    129 Hobbs St, 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 $406,949

    Last Listing Agent Danny Martin Keller Williams Flagship

    333 Morning Glory Dr, Denton, MD 21629
    • 111 Maple Ave, Goldsboro, MD 21636
      111 Maple Ave, Goldsboro, MD 21636
      111 Maple Ave, Goldsboro, MD 21636
      /19

      Est $290,896 Not Listed For Sale

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

      111 Maple Ave, Goldsboro, MD 21636

      111 Maple Ave, Goldsboro, MD 21636
  • 208 Oriole Ave, Ridgely, MD 21660
    208 Oriole Ave, Ridgely, MD 21660
    208 Oriole Ave, Ridgely, MD 21660
    /28

    $339,000

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

    208 Oriole Ave, Ridgely, MD 21660

    Come see this Beautiful well maintained Ranch home in the heart of Ridgely. The house is a block away from the local park. The house has had many upgrades including an addition in 2020. New siding in 2020. New deck after 2020. New windows in 2017. There are solar panels on the roof. Spacious back yard with a patio. Many other upgrades to come and see.

    Rachel Penska Long & Foster Real Estate, Inc.

    208 Oriole Ave, Ridgely, MD 21660
  • 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 $324,846

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    3 Oak St, Ridgely, MD 21660
    • 139 Smugglers Way, Greensboro, MD 21639
      139 Smugglers Way, Greensboro, MD 21639
      139 Smugglers Way, Greensboro, MD 21639
      /26

      Est $277,324 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft

      139 Smugglers Way, Greensboro, MD 21639

      139 Smugglers Way, Greensboro, MD 21639
  • 3675 Seaman Rd, Preston, MD 21655
    3675 Seaman Rd, Preston, MD 21655
    3675 Seaman Rd, Preston, MD 21655
    /35

    $310,000

    • 3 Beds
    • 2 Baths
    • 1,787 Sq Ft

    3675 Seaman Rd, Preston, MD 21655

    Charming Eastern Shore property set on a peaceful stretch of Seaman’s Road in Preston, MD. Enjoy the tranquility of country living with convenient access to nearby towns, outdoor recreation, and local amenities. A great opportunity for those seeking space, privacy, and small-town charm.

    Brian Jones Keller Williams Select Realtors of Annapolis

    3675 Seaman Rd, Preston, MD 21655
  • 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 $338,332

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

    3880 Laurel Grove Rd, Federalsburg, MD 21632
    • 110 Sharp Rd, Denton, MD 21629
      110 Sharp Rd, Denton, MD 21629
      110 Sharp Rd, Denton, MD 21629
      /30

      Est $382,850 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,851 Sq Ft

      110 Sharp Rd, Denton, MD 21629

      110 Sharp Rd, Denton, MD 21629
  • 3376 Jefferson Pond Rd, Federalsburg, MD 21632
    3376 Jefferson Pond Rd, Federalsburg, MD 21632
    3376 Jefferson Pond Rd, Federalsburg, MD 21632
    /5

    $300,000 Pending

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

    3376 Jefferson Pond Rd, Federalsburg, MD 21632

    This beautifully crafted 3 bedroom, 2 bathroom home offers modern living in a sought-after community with a low annual HOA fee of just $200. Step inside to find luxury vinyl plank flooring throughout the main living areas, a spacious open-concept layout, and a stunning kitchen featuring granite countertops, stainless steel appliances, and plenty of cabinet space. Enjoy peace of mind with a

    Amy Herr Keller Williams Realty

    3376 Jefferson Pond Rd, Federalsburg, MD 21632
  • 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
    • 27701 Burrsville Rd, Denton, MD 21629
      27701 Burrsville Rd, Denton, MD 21629
      27701 Burrsville Rd, Denton, MD 21629
      /14

      Est $301,358 Not Listed For Sale

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

      27701 Burrsville Rd, Denton, MD 21629

      27701 Burrsville Rd, Denton, MD 21629
  • 320 N Main St, Greensboro, MD 21639
    320 N Main St, Greensboro, MD 21639
    320 N Main St, Greensboro, MD 21639
    /40

    $460,000

    • 3 Beds
    • 2.5 Baths
    • 1,816 Sq Ft

    320 N Main St, Greensboro, MD 21639

    Welcome to 320 N Main St in the quaint town of Greensboro, where you'll find a home that invites you to kick off your shoes and stay a while. This residence sits on a half-acre lot and features three bedrooms and 2.5 baths, offering an ideal balance of space, comfort, and style. The beautifully updated kitchen is ready for all your culinary adventures, boasting a five-burner gas range, stainless

    Karen Clark Clark & Co Realty, LLC

    320 N Main St, 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 $209,310

    Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

    22038 Church St, Hillsboro, MD 21641
    • 504 Liberty Rd, Federalsburg, MD 21632
      504 Liberty Rd, Federalsburg, MD 21632
      504 Liberty Rd, Federalsburg, MD 21632
      /36

      Est $268,336 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,620 Sq Ft

      504 Liberty Rd, Federalsburg, MD 21632

      504 Liberty Rd, Federalsburg, MD 21632
  • 25548 Hill Rd, Greensboro, MD 21639
    25548 Hill Rd, Greensboro, MD 21639
    25548 Hill Rd, Greensboro, MD 21639
    /13

    $435,000

    • Studio
    • 7,260 Sq Ft

    25548 Hill Rd, Greensboro, MD 21639

    HUGE POTENTIAL. Residential/commercial property combined. 4 residential units available. Two units occupied with annual leases (one at $700.00 and the other at $725.00). Two units vacant (one needs some work and the other needs extensive work. All 4 units are Certified Lead Free. Large main section is gutted and has excellent potential for apartments, etc. Buyer and or Buyer's agent to

    Rosa Tyre Kelark Real Estate

    25548 Hill Rd, Greensboro, MD 21639
  • 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 $484,866

    Last Listing Agent Peter Mellor Wright Real Estate

    14462 Poplar St, Goldsboro, MD 21636
    • 103 Elmor Ct, Greensboro, MD 21639
      103 Elmor Ct, Greensboro, MD 21639
      103 Elmor Ct, Greensboro, MD 21639
      /20

      Est $405,883 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,232 Sq Ft

      103 Elmor Ct, Greensboro, MD 21639

      103 Elmor Ct, Greensboro, MD 21639
  • 21269 Dover Bridge Rd, Preston, MD 21655
    21269 Dover Bridge Rd, Preston, MD 21655
    /2

    $80,000 Coming Soon

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

    21269 Dover Bridge Rd, Preston, MD 21655

    Nestled in Dover Bridge Mobile Home Park—formerly Prettyman Manor—this double-wide manufactured home sits on one of the largest lots in this peaceful community. The property offers plenty of space and potential, with a few upcoming improvements to help set the stage for its next owner. While it could use a bit of attention, it’s a wonderful opportunity to make this home your own in a quiet,

    Kelly Howard Coldwell Banker Realty

    21269 Dover Bridge Rd, Preston, MD 21655
  • 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 $267,536

    Last Listing Agent Jennifer Chaney Chaney Homes, LLC

    11204 Academy St, Hillsboro, MD 21641
    • 312 Buena Vista Ave, Federalsburg, MD 21632
      312 Buena Vista Ave, Federalsburg, MD 21632
      312 Buena Vista Ave, Federalsburg, MD 21632
      /19

      Est $211,369 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,308 Sq Ft

      312 Buena Vista Ave, Federalsburg, MD 21632

      312 Buena Vista Ave, Federalsburg, MD 21632
  • 1202 Blue Heron Dr, Denton, MD 21629
    1202 Blue Heron Dr, Denton, MD 21629
    1202 Blue Heron Dr, Denton, MD 21629
    /13

    $235,000

    • 3 Beds
    • 2.5 Baths
    • 1,753 Sq Ft

    1202 Blue Heron Dr, Denton, MD 21629

    WELCOME HOME!!! 1753 SQ FT OF COMFORT...... 3 FLOORS, 3 SPACIOUS BEDROOMS, 3 BATHROOMS, WHITE WOOD CABINETS, MARBLE COUNTERTOPS, STAINLESS STEEL APPLIANCES, LUXURY VINYL FLOORING DOWNSTAIRS, FULLY CARPETED UPSTAIRS, LAUNDRY ROOM, PANTRY AND MORE. CORNER LOT/ QUICK ENTRY & EXIT/ PLAYGROUND/ POOL / CLUBHOUSE/ PET FRIENDLY NEIGHBORHOOD/ HOA / CLOSE DRIVE TO SCHOOLS, STORES, OCEAN CITY, CHESAPEAKE

    SHANTA PHILLIPS EXP Realty, LLC

    1202 Blue Heron Dr, Denton, MD 21629
  • 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
    • 25766 Beauchamp Branch Rd, Denton, MD 21629
      25766 Beauchamp Branch Rd, Denton, MD 21629
      25766 Beauchamp Branch Rd, Denton, MD 21629
      /95

      Est $554,896 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
  • 245 Briarwood Cir, Denton, MD 21629
    245 Briarwood Cir, Denton, MD 21629
    245 Briarwood Cir, Denton, MD 21629
    /10

    $225,000 Under Contract

    • Studio

    245 Briarwood Cir, Denton, MD 21629

    Improved 4 adjoining townhouse parcels with concrete slab that needs to be replaced.)Beginning of the Sandy Meadows community that is its own block offering privacy outside of crowded downtown for you to Build and sell or rent.Listing shows one lotLots 55, 56, 57 & 58 This is a unique opportunity for small project in a nice setting.Easy access to Route 404, shopping, dining and

    Phil Riordan Meredith Fine Properties

    245 Briarwood Cir, Denton, MD 21629
  • 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 $218,778

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

    524 Denton Rd, Federalsburg, MD 21632
    • 6293 Statum Rd, Preston, MD 21655
      6293 Statum Rd, Preston, MD 21655
      6293 Statum Rd, Preston, MD 21655
      /52

      Est $612,888 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
  • 26519 3 Bridges Rd, Federalsburg, MD 21632
    26519 3 Bridges Rd, Federalsburg, MD 21632
    /2

    $30,000

    • Land
    • 0.54 Acre
    • $55,556 per Acre

    26519 3 Bridges Rd, Federalsburg, MD 21632

    Previous building is a complete tear down. Do not enter the building. Half acre lot zoned R1, one property. Buyer must contact Caroline County for any more information. There could be a private community septic on the property. Seller will consider holding a 2 year note with $15,000 down payment.

    Charles Hajjar Smart Realty, LLC

    26519 3 Bridges Rd, Federalsburg, MD 21632
  • 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 $212,864

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

    502 W Sunset Ave, Greensboro, MD 21639
    • 1150 Canvasback Ln, Denton, MD 21629
      1150 Canvasback Ln, Denton, MD 21629
      1150 Canvasback Ln, Denton, MD 21629
      /30

      Est $302,951 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
  • 25607 Garey Rd, Denton, MD 21629
    25607 Garey Rd, Denton, MD 21629
    25607 Garey Rd, Denton, MD 21629
    /19

    $315,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 920 Sq Ft

    25607 Garey Rd, Denton, MD 21629

    This inviting 3-bedroom, 2-bath rancher sits on 1.25 peaceful acres and is full of thoughtful updates and outdoor features you'll love. Step inside to find fresh paint, new carpet, durable LVP flooring, and newer appliances—all in a comfortable, move-in ready layout. The exterior offers just as much to enjoy: a large backyard, spacious deck, patio, and a storage shed for all your tools or toys. A

    Kaitlyn Collins Benson & Mangold, LLC

    25607 Garey 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
    • 24541 Hynson Rd, Federalsburg, MD 21632
      24541 Hynson Rd, Federalsburg, MD 21632
      24541 Hynson Rd, Federalsburg, MD 21632
      /15

      Est $252,624 Not Listed For Sale

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

      24541 Hynson Rd, Federalsburg, MD 21632

      24541 Hynson Rd, Federalsburg, MD 21632
  • 0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629
    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629
    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629
    /16

    $249,900 Under Contract

    • Land
    • 3.4 Acres
    • $73,500 per Acre

    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629

    Farm land or a Home site. Convenient to Denton and 404. 3 parcels totaling 21.11 acres are included in the offering. Tillable land and wooded. Great spot for someone with horses or that wants to hunt. Perk approval on Parcel 83. Approx. 3.7 tillable acreage.

    Eddie Matthews Benson & Mangold, LLC

    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629
  • 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

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    113 Boyce Mill Rd, Greensboro, MD 21639
    • 13389 Mason Branch Rd, Ridgely, MD 21660
      13389 Mason Branch Rd, Ridgely, MD 21660
      13389 Mason Branch Rd, Ridgely, MD 21660
      /49

      Est $819,970 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
  • 3485 Gallagher Rd, Preston, MD 21655
    3485 Gallagher Rd, Preston, MD 21655
    3485 Gallagher Rd, Preston, MD 21655
    /74

    $740,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 3,326 Sq Ft

    3485 Gallagher Rd, Preston, MD 21655

    **Accepting other offers** Situated on 4.14± private acres, this 3-bedroom, 2.5-bath home couples serene country living with exceptional craftsmanship. Inside, the first floor offers a formal dining room, large eat in kitchen with stainless steel appliances, vaulted ceiling living room with two story stone fireplace, first floor primary with walk in closet and Whirlpool tub, office with built

    Alicia Gannon Dulin Benson & Mangold, LLC

    3485 Gallagher Rd, Preston, MD 21655
  • 203 Bernard Ave, Federalsburg, MD 21632
    203 Bernard Ave, Federalsburg, MD 21632
    203 Bernard Ave, Federalsburg, MD 21632
    /22

    $225,000 Sold Jun 18, 2025

    203 Bernard Ave, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1972

    Last Sold Summary

    • $213/SF
    • 31 Days On Market

    Current Estimated Value $234,480

    Last Listing Agent Valerie Brown Charles C. Powell, Inc. Realtors

    203 Bernard Ave, Federalsburg, MD 21632

Showing Results 281 - 320, Page 8 of 18

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