15,675

Caroline County, MD Homes

Section Image
  • 6 N Central Ave, Ridgely, MD 21660
    6 N Central Ave, Ridgely, MD 21660
    /2

    $79,900

    • Land
    • 0.21 Acre
    • $380,476 per Acre

    6 N Central Ave, Ridgely, MD 21660

    Zoned commercial is this prime lot in the heart of Ridgely and next to the Town Office. Convenient street parking fronting the lot.

    Chuck Jr. Benson and Mangold

    6 N Central Ave, Ridgely, MD 21660
  • 5 Maryland Ave Unit 5A, Ridgely, MD 21660
    5 Maryland Ave Unit 5A, Ridgely, MD 21660
    5 Maryland Ave Unit 5A, Ridgely, MD 21660
    /9

    $1,275 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    5 Maryland Ave Unit 5A, Ridgely, MD 21660

    Apartment 2nd Floor, 1Br/1Ba, Electric Heat, no pets, no smoking, 1275. per month water/sewer/trash included. tenant pays electric. Approved Application (29.00 Fee), First Months rent and Security of 1275.00 to move in.

    5 Maryland Ave Unit 5A, Ridgely, MD 21660
  • 111 Riverton Ave, Denton, MD 21629
    111 Riverton Ave, Denton, MD 21629
    111 Riverton Ave, Denton, MD 21629
    /46

    $219,000 Sold Feb 13, 2025

    111 Riverton Ave, Denton, MD 21629

    • 4 Beds
    • 1.5 Baths
    • 1,868 Sq Ft
    • Built 1916

    Last Sold Summary

    • $117/SF
    • 32 Days On Market

    Current Estimated Value $255,137

    Last Listing Agent Megan Rosendale Rosendale Realty

    111 Riverton Ave, Denton, MD 21629
    • 204 Horsey St, Greensboro, MD 21639
      204 Horsey St, Greensboro, MD 21639
      204 Horsey St, Greensboro, MD 21639
      /38

      Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,024 Sq Ft

      204 Horsey St, Greensboro, MD 21639

      204 Horsey St, Greensboro, MD 21639
  • 11305 River Rd, Ridgely, MD 21660
    11305 River Rd, Ridgely, MD 21660
    11305 River Rd, Ridgely, MD 21660
    /14

    $345,000

    • 3 Beds
    • 1 Bath
    • 1,533 Sq Ft

    11305 River Rd, Ridgely, MD 21660

    Charming 3-bedroom, 1-bath rancher offers over 1500 SF of comfortable living space. Several updates have already been completed, making this home move in ready with room to add your own touches. Enjoy peaceful mornings and evenings on the screened-in rear porch, perfect for relaxing while taking in the surrounding wildlife. A great blend of comfort, space and natural serenity.

    Pamela Geib Long & Foster Real Estate, Inc.

    11305 River Rd, Ridgely, MD 21660
  • 26056 Fox Grape Rd, Greensboro, MD 21639
    26056 Fox Grape Rd, Greensboro, MD 21639
    26056 Fox Grape Rd, Greensboro, MD 21639
    /24

    $290,000 Sold Jan 15, 2026

    26056 Fox Grape Rd, Greensboro, MD 21639

    • 3 Beds
    • 1.5 Baths
    • 1,215 Sq Ft
    • Built 1981

    Last Sold Summary

    • $239/SF
    • 2 Days On Market

    Last Listing Agent Amanda Morgan Brenton Realty Group

    26056 Fox Grape Rd, Greensboro, MD 21639
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /10

      Est $558,144 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,300 Sq Ft

      Unlisted Address

      Unlisted Address
  • 15184 Jarrell Rd, Goldsboro, MD 21636
    15184 Jarrell Rd, Goldsboro, MD 21636
    15184 Jarrell Rd, Goldsboro, MD 21636
    /80

    $749,900 Pending

    • 6 Beds
    • 4.5 Baths
    • 5,000 Sq Ft

    15184 Jarrell Rd, Goldsboro, MD 21636

    BACK ON THE MARKET AND READY TO GO.....Buyers Financing fell through. All inspections (Home, Septic & Well) are completed and any issues have been addressed. Seller says "COME ON DOWN AND LETS MAKE A DEAL". Gorgeous 12.12 acre tree lined property. This privately built home has features one could only dream of...consisting of 5,000 plus sq. ft. , this home has a total of 6bd &4.5ba. It is perfect

    Leslie Fulford Mann & Sons, Inc.

    15184 Jarrell Rd, Goldsboro, MD 21636
  • 23993 E Cherry Ln, Goldsboro, MD 21636
    23993 E Cherry Ln, Goldsboro, MD 21636
    23993 E Cherry Ln, Goldsboro, MD 21636
    /17

    $110,000 Sold Apr 11, 2025

    23993 E Cherry Ln, Goldsboro, MD 21636

    • Land
    • 2.2 Acres
    • $50,000 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $117,016

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    23993 E Cherry Ln, Goldsboro, MD 21636
    • 323 Mallard Dr, Greensboro, MD 21639
      323 Mallard Dr, Greensboro, MD 21639
      323 Mallard Dr, Greensboro, MD 21639
      /23

      Est $326,771 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,632 Sq Ft

      323 Mallard Dr, Greensboro, MD 21639

      323 Mallard Dr, Greensboro, MD 21639
  • 0 Quail Ct Unit MDCM2006644, Greensboro, MD 21639
    0 Quail Ct Unit MDCM2006644, Greensboro, MD 21639
    0 Quail Ct Unit MDCM2006644, Greensboro, MD 21639
    /14

    $399,000 Under Contract

    • 3 Beds
    • 2 Baths

    0 Quail Ct Unit MDCM2006644, Greensboro, MD 21639

    Quick Delivery – To Be Built Rancher!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

    Barbara Blosser Long & Foster Real Estate, Inc.

    0 Quail Ct Unit MDCM2006644, Greensboro, MD 21639
  • 403 Gay St, Denton, MD 21629
    403 Gay St, Denton, MD 21629
    403 Gay St, Denton, MD 21629
    /25

    $420,000 Sold Feb 11, 2025

    403 Gay St, Denton, MD 21629

    • Studio
    • 1,280 Sq Ft
    • Built 1880

    Last Sold Summary

    • $328/SF
    • 93 Days On Market

    Last Listing Agent Andrew Beaven Wright Real Estate

    403 Gay St, Denton, MD 21629
    • 319 Mallard Dr, Greensboro, MD 21639
      319 Mallard Dr, Greensboro, MD 21639
      319 Mallard Dr, Greensboro, MD 21639
      /30

      Est $313,501 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,468 Sq Ft

      319 Mallard Dr, Greensboro, MD 21639

      319 Mallard Dr, Greensboro, MD 21639
  • 25999 Fox Grape Rd, Greensboro, MD 21639
    25999 Fox Grape Rd, Greensboro, MD 21639
    25999 Fox Grape Rd, Greensboro, MD 21639
    /27

    $379,000

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

    25999 Fox Grape Rd, Greensboro, MD 21639

    Welcome to this beautifully updated 4-bedroom, 2-bath home nestled in the peaceful Fox Grape Farms community. This move-in-ready property features a recently remodeled kitchen and bathrooms, along with refinished hardwood floors that add warmth and charm throughout. Set on a serene half-acre wooded lot, the home offers wonderful outdoor living with an 8' x 14' enclosed porch, a rear deck with a

    Amy Betts Coldwell Banker Realty

    25999 Fox Grape Rd, Greensboro, MD 21639
  • 28471 Kinder Rd, Federalsburg, MD 21632
    28471 Kinder Rd, Federalsburg, MD 21632
    28471 Kinder Rd, Federalsburg, MD 21632
    /5

    $132,000 Sold Sep 25, 2025

    28471 Kinder Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1963

    Last Sold Summary

    • $206/SF
    • 71 Days On Market

    Current Estimated Value $150,990

    Last Listing Agent Gillian Walsh Keller Williams Realty

    28471 Kinder Rd, Federalsburg, MD 21632
    • 25970 Three Bridges Rd, Federalsburg, MD 21632
      25970 Three Bridges Rd, Federalsburg, MD 21632
      25970 Three Bridges Rd, Federalsburg, MD 21632
      /66

      Est $307,096 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,844 Sq Ft

      25970 Three Bridges Rd, Federalsburg, MD 21632

      25970 Three Bridges Rd, Federalsburg, MD 21632
  • 130 Charlotte Ave, Federalsburg, MD 21632
    130 Charlotte Ave, Federalsburg, MD 21632
    130 Charlotte Ave, Federalsburg, MD 21632
    /23

    $310,000

    • 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
  • 6238 Bethlehem Rd, Preston, MD 21655
    6238 Bethlehem Rd, Preston, MD 21655
    6238 Bethlehem Rd, Preston, MD 21655
    /37

    $238,000 Sold Oct 07, 2025

    6238 Bethlehem Rd, Preston, MD 21655

    • 2 Beds
    • 1 Bath
    • 1,234 Sq Ft
    • Built 1875

    Last Sold Summary

    • $193/SF
    • 34 Days On Market

    Current Estimated Value $361,620

    Last Listing Agent Amy Betts Coldwell Banker Realty

    6238 Bethlehem Rd, Preston, MD 21655
    • 206 Maple Ave, Ridgely, MD 21660
      206 Maple Ave, Ridgely, MD 21660
      206 Maple Ave, Ridgely, MD 21660
      /19

      Est $240,047 Not Listed For Sale

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

      206 Maple Ave, Ridgely, MD 21660

      206 Maple Ave, Ridgely, MD 21660
  • 24029 Meadows Dr, Ridgely, MD 21660
    24029 Meadows Dr, Ridgely, MD 21660
    24029 Meadows Dr, Ridgely, MD 21660
    /39

    $384,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft

    24029 Meadows Dr, Ridgely, MD 21660

    Enjoy the best of Eastern Shore living with the tranquility of a quiet, country setting while remaining conveniently located just outside of the quaint little town of Ridgely. This nanticoke rancher features a nice family room addition off the kitchen and is located on a private 2 acre lot on the end of a cul-de-sac. Featuring 3 bedrooms and 2 full baths and a two car garage. This property also

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    24029 Meadows Dr, Ridgely, MD 21660
  • 3590 Choptank Rd, Preston, MD 21655
    3590 Choptank Rd, Preston, MD 21655
    3590 Choptank Rd, Preston, MD 21655
    /44

    $355,000 Sold Aug 29, 2025

    3590 Choptank Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,476 Sq Ft
    • Built 1994

    Last Sold Summary

    • $241/SF
    • 32 Days On Market

    Current Estimated Value $377,560

    Last Listing Agent Dawn O'Day Samson Properties

    3590 Choptank Rd, Preston, MD 21655
    • 24776 Tribbett Cir, Ridgely, MD 21660
      24776 Tribbett Cir, Ridgely, MD 21660
      24776 Tribbett Cir, Ridgely, MD 21660
      /5

      Est $511,660 Not Listed For Sale

      24776 Tribbett Cir, Ridgely, MD 21660

      24776 Tribbett Cir, Ridgely, MD 21660
  • 407 Wood Duck Dr, Greensboro, MD 21639
    407 Wood Duck Dr, Greensboro, MD 21639
    407 Wood Duck Dr, Greensboro, MD 21639
    /32

    $315,000 Pending

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

    407 Wood Duck Dr, Greensboro, MD 21639

    SELLERS ARE OFFERING A $2,500 CREDIT toward refinishing hardwood floors with a reasonable offer, an amazing opportunity to customize the look to your taste. TOP 10 FEATURES you will love about this home: 1) FOUR spacious bedrooms for under $320,000 with the primary bedroom having its on en-suite. 2) Built in 2004, offering modern construction, efficient systems, and a solid layout. 3) Backs to

    Kathryn Matic Patterson-Schwartz - Greenville

    407 Wood Duck Dr, Greensboro, MD 21639
  • 13243 Greensboro Rd, Greensboro, MD 21639
    13243 Greensboro Rd, Greensboro, MD 21639
    /2

    $100,000 Sold Nov 21, 2025

    13243 Greensboro Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,092 Sq Ft
    • Built 1910

    Last Sold Summary

    • $92/SF
    • 5 Days On Market

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    13243 Greensboro Rd, Greensboro, MD 21639
    • 1202 Trice Meadows Cir, Denton, MD 21629
      1202 Trice Meadows Cir, Denton, MD 21629
      1202 Trice Meadows Cir, Denton, MD 21629
      /27

      Est $366,636 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,540 Sq Ft

      1202 Trice Meadows Cir, Denton, MD 21629

      1202 Trice Meadows Cir, Denton, MD 21629
  • 4757 Long Swamp Rd, Federalsburg, MD 21632
    4757 Long Swamp Rd, Federalsburg, MD 21632
    4757 Long Swamp Rd, Federalsburg, MD 21632
    /47

    $695,000

    • 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
  • 26067 Goldsboro Rd, Goldsboro, MD 21636
    26067 Goldsboro Rd, Goldsboro, MD 21636
    26067 Goldsboro Rd, Goldsboro, MD 21636
    /21

    $629,900 Sold Jan 12, 2026

    26067 Goldsboro Rd, Goldsboro, MD 21636

    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft
    • Built 2024

    Last Sold Summary

    • $303/SF
    • 7 Days On Market

    Last Listing Agent Scott Judy Coldwell Banker Waterman Realty

    26067 Goldsboro Rd, Goldsboro, MD 21636
    • 1101 Trice Meadows Cir, Denton, MD 21629
      1101 Trice Meadows Cir, Denton, MD 21629
      1101 Trice Meadows Cir, Denton, MD 21629
      /10

      Est $423,050 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,300 Sq Ft

      1101 Trice Meadows Cir, Denton, MD 21629

      1101 Trice Meadows Cir, Denton, MD 21629
  • 25749 Herring Ln, Denton, MD 21629
    25749 Herring Ln, Denton, MD 21629
    25749 Herring Ln, Denton, MD 21629
    /50

    $575,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,190 Sq Ft

    25749 Herring Ln, Denton, MD 21629

    Back on the market no fault of the seller. Welcome to your dream home! This beautifully maintained 3-bedroom, 2.5-bath rancher offers modern comfort and incredible outdoor amenities. Nestled on a spacious lot, just under 3 acres, this home boasts all-new stainless steel appliances, a newer HVAC system, and solar panels for energy efficiency bringing your electric bills down to $15-$50 a month!

    Justin Damadio Iron Valley Real Estate Ocean City

    25749 Herring Ln, Denton, MD 21629
  • 8602 Hickory Place, 3, Denton, MD 21629
    8602 Hickory Place, 3, Denton, MD 21629
    8602 Hickory Place, 3, Denton, MD 21629
    /3

    $20,000 Sold Apr 23, 2025

    8602 Hickory Place, 3, Denton, MD 21629

    • Land
    • 1.28 Acres
    • $15,625 per Acre

    Last Sold Summary

    • 11 Days On Market

    Current Estimated Value $31,667

    Last Listing Agent Amanda Morgan Brenton Realty Group

    8602 Hickory Place, 3, Denton, MD 21629
    • 204 Briarwood Cir, Denton, MD 21629
      204 Briarwood Cir, Denton, MD 21629
      204 Briarwood Cir, Denton, MD 21629
      /15

      Est $379,779 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      204 Briarwood Cir, Denton, MD 21629

      204 Briarwood Cir, Denton, MD 21629
  • 11142 Log Cabin Rd, Denton, MD 21629
    11142 Log Cabin Rd, Denton, MD 21629
    11142 Log Cabin Rd, Denton, MD 21629
    /55

    $699,900

    • 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
  • 5569 Harmony Woods Dr, Preston, MD 21655
    5569 Harmony Woods Dr, Preston, MD 21655
    5569 Harmony Woods Dr, Preston, MD 21655
    /52

    $470,000 Sold Jun 11, 2025

    5569 Harmony Woods Dr, Preston, MD 21655

    • 4 Beds
    • 2.5 Baths
    • 2,909 Sq Ft
    • Built 2005

    Last Sold Summary

    • $162/SF
    • 185 Days On Market

    Current Estimated Value $513,963

    Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

    5569 Harmony Woods Dr, Preston, MD 21655
    • 613 Denton Rd, Federalsburg, MD 21632
      613 Denton Rd, Federalsburg, MD 21632
      613 Denton Rd, Federalsburg, MD 21632
      /21

      Est $235,014 Not Listed For Sale

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

      613 Denton Rd, Federalsburg, MD 21632

      613 Denton Rd, Federalsburg, MD 21632
  • 211 Bloomingdale Ave, Federalsburg, MD 21632
    211 Bloomingdale Ave, Federalsburg, MD 21632
    211 Bloomingdale Ave, Federalsburg, MD 21632
    /29

    $339,000

    • 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
  • 313 Reliance Ave, Federalsburg, MD 21632
    313 Reliance Ave, Federalsburg, MD 21632
    313 Reliance Ave, Federalsburg, MD 21632
    /31

    $158,000 Sold Feb 26, 2025

    313 Reliance Ave, Federalsburg, MD 21632

    • 1 Bed
    • 1 Bath
    • 988 Sq Ft
    • Built 1960

    Last Sold Summary

    • $160/SF
    • 8 Days On Market

    Current Estimated Value $172,692

    Last Listing Agent Mary Jameson Long & Foster Real Estate, Inc.

    313 Reliance Ave, Federalsburg, MD 21632
    • 510 Lincoln St, Denton, MD 21629
      510 Lincoln St, Denton, MD 21629
      510 Lincoln St, Denton, MD 21629
      /3

      Est $292,174 Not Listed For Sale

      510 Lincoln St, Denton, MD 21629

      510 Lincoln St, Denton, MD 21629
  • 282 Tidewater Cir, Preston, MD 21655
    282 Tidewater Cir, Preston, MD 21655
    282 Tidewater Cir, Preston, MD 21655
    /33

    $449,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,946 Sq Ft

    282 Tidewater Cir, Preston, MD 21655

    Step into this absolutely beautiful 2-story home with a basement, where pride of ownership shines from the moment you walk through the front door. Offering approximately 3,900 finished square feet, this home features stylish LVP flooring and cozy carpet throughout, with spacious bedrooms and a layout that’s both functional and inviting. The heart of the home is the large kitchen, complete with

    Heather Brummell Keller Williams Realty

    282 Tidewater Cir, Preston, MD 21655
  • 25790 Herring Ln, Denton, MD 21629
    25790 Herring Ln, Denton, MD 21629
    25790 Herring Ln, Denton, MD 21629
    /34

    $469,000 Sold Oct 10, 2025

    25790 Herring Ln, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 2,132 Sq Ft
    • Built 1989

    Last Sold Summary

    • $220/SF
    • 18 Days On Market

    Current Estimated Value $475,489

    Last Listing Agent Elizabeth Tryon Coldwell Banker Realty

    25790 Herring Ln, Denton, MD 21629
    • 13416 Greensboro Rd, Greensboro, MD 21639
      13416 Greensboro Rd, Greensboro, MD 21639
      13416 Greensboro Rd, Greensboro, MD 21639
      /26

      Est $128,735 Not Listed For Sale

      13416 Greensboro Rd, Greensboro, MD 21639

      13416 Greensboro Rd, Greensboro, MD 21639

Showing Results 41 - 80, Page 2 of 18

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