15,718

Caroline County, MD Homes

Section Image
    • 1107 Ruddy Duck Ct, Denton, MD 21629
      1107 Ruddy Duck Ct, Denton, MD 21629
      1107 Ruddy Duck Ct, Denton, MD 21629
      /61

      Est $429,863

      Not Listed For Sale

      1107 Ruddy Duck Ct, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,914 Sq Ft
      • Built 2006
      1107 Ruddy Duck Ct, Denton, MD 21629

      Last Sold Summary

      • 7 Days On Market

  • 22005 Main St, Hillsboro, MD 21641
    22005 Main St, Hillsboro, MD 21641
    22005 Main St, Hillsboro, MD 21641
    /74

    $525,000

    • 3 Beds
    • 3 Baths
    • 3,088 Sq Ft

    22005 Main St, Hillsboro, MD 21641

    PLEASE NOTE that the Owner has listened to the current market, Price has been reduced to $525,000. It is a property of beautifully preserved quality on 3⁄4 of an acre in an urban setting. Most unusual! When compared to equivalent historic properties it is now very competitively priced! This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641
  • 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

    $230,000

    Sold Jan 30, 2026

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

    • Land
    • 3.4 Acres
    • $67,647 per Acre

    Last Sold Summary

    • 30% Below List Price
    • 631 Days On Market

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629
    • 6 Oak St, Ridgely, MD 21660
      6 Oak St, Ridgely, MD 21660
      6 Oak St, Ridgely, MD 21660
      /19

      Est $332,168

      Not Listed For Sale

      6 Oak St, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,480 Sq Ft
      • Built 1979
      6 Oak St, Ridgely, MD 21660

      Last Sold Summary

      • 2 Days On Market

  • 10440 Burrsville Branch Rd, Denton, MD 21629
    10440 Burrsville Branch Rd, Denton, MD 21629
    10440 Burrsville Branch Rd, Denton, MD 21629
    /9

    $79,000

    • Land
    • 3.05 Acres
    • $25,902 per Acre

    10440 Burrsville Branch Rd, Denton, MD 21629

    Rare opportunity to own over 3 acres in a peaceful rural setting just outside of Denton and approximately one mile from the Maryland/Delaware state line. Close to Delaware Beaches and Tax Free Shopping. This partially wooded homesite backs to open farmland, offering privacy and picturesque country views. The property provides an ideal setting for a custom home, subject to the installation of a

    Deborah Callahan Benson & Mangold, LLC

    10440 Burrsville Branch Rd, Denton, MD 21629
  • 14271 Cedar Ln, Greensboro, MD 21639
    14271 Cedar Ln, Greensboro, MD 21639
    14271 Cedar Ln, Greensboro, MD 21639
    /108

    $1,200,000

    Sold Jan 21, 2026

    14271 Cedar Ln, Greensboro, MD 21639

    • 6 Beds
    • 3 Baths
    • 3,756 Sq Ft
    • Built 1998

    Last Sold Summary

    • $319/SF
    • 245 Days On Market

    Current Estimated Value $1,160,048

    Last Listing Agent Travis Gray Engel & Völkers Annapolis

    14271 Cedar Ln, Greensboro, MD 21639
    • 11412 Cecil Ct, Greensboro, MD 21639
      11412 Cecil Ct, Greensboro, MD 21639
      11412 Cecil Ct, Greensboro, MD 21639
      /36

      Est $472,779

      Not Listed For Sale

      11412 Cecil Ct, Greensboro, MD 21639

      • 4 Beds
      • 2.5 Baths
      • 2,100 Sq Ft
      • Built 2005
      11412 Cecil Ct, Greensboro, MD 21639

      Last Sold Summary

      • 28 Days On Market

  • 313 Holt St, Federalsburg, MD 21632
    313 Holt St, Federalsburg, MD 21632
    313 Holt St, Federalsburg, MD 21632
    /21

    $215,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,008 Sq Ft

    313 Holt St, Federalsburg, MD 21632

    Welcome home to 313 Holt Street located in a quiet section of Federalsburg Maryland. This is a move-in ready home with new windows, new carpet and has been freshly painted inside.

    Joseph Hawkins Hawkins Real Estate Company

    313 Holt St, Federalsburg, MD 21632
  • 14418 Poplar St, Goldsboro, MD 21636
    14418 Poplar St, Goldsboro, MD 21636
    14418 Poplar St, Goldsboro, MD 21636
    /52

    $465,000

    Sold Jun 16, 2026

    14418 Poplar St, Goldsboro, MD 21636

    • 2 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1989

    Last Sold Summary

    • 5% Above List Price
    • $252/SF
    • 6 Days On Market

    Current Estimated Value $445,152

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    14418 Poplar St, Goldsboro, MD 21636
    • 203 Greenridge Rd, Federalsburg, MD 21632
      203 Greenridge Rd, Federalsburg, MD 21632
      203 Greenridge Rd, Federalsburg, MD 21632
      /32

      Est $231,784

      Not Listed For Sale

      203 Greenridge Rd, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,479 Sq Ft
      • Built 1938
      203 Greenridge Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 29 Days On Market

  • 305 Old Denton Rd, Federalsburg, MD 21632
    305 Old Denton Rd, Federalsburg, MD 21632
    305 Old Denton Rd, Federalsburg, MD 21632
    /5

    $89,900

    Pending
    • 2 Beds
    • 1 Bath
    • 600 Sq Ft

    305 Old Denton Rd, Federalsburg, MD 21632

    ** BEST AND FINAL OFFERS DUE 6/12/26 AT NOON ** Investor Alert!! This rancher, situated on over half an acre, is packed with value-add potential! With some TLC and the right vision, this property could be transformed into a strong income-producing asset or profitable flip in no time. Whether you’re looking to renovate and rent or resell, the opportunity here is undeniable—especially with a

    Aubrey Campbell Keller Williams Realty Delmarva

    305 Old Denton Rd, Federalsburg, MD 21632
  • 111 Parkland Rd, Greensboro, MD 21639
    111 Parkland Rd, Greensboro, MD 21639
    /2

    $289,990

    Sold Sep 25, 2025

    111 Parkland Rd, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    Last Sold Summary

    • $199/SF
    • 13 Days On Market

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

    111 Parkland Rd, Greensboro, MD 21639
    • 108 Liberty Rd, Federalsburg, MD 21632
      108 Liberty Rd, Federalsburg, MD 21632
      108 Liberty Rd, Federalsburg, MD 21632
      /24

      Est $232,335

      Not Listed For Sale

      108 Liberty Rd, Federalsburg, MD 21632

      • 3 Beds
      • 1.5 Baths
      • 1,756 Sq Ft
      • Built 1890
      108 Liberty Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 177 Days On Market

  • 311 Maple Ave, Federalsburg, MD 21632
    311 Maple Ave, Federalsburg, MD 21632
    311 Maple Ave, Federalsburg, MD 21632
    /41

    $261,500

    $8K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    311 Maple Ave, Federalsburg, MD 21632

    Coming Soon! Prepare to be impressed by this stunning, top-to-bottom transformation. This home has been thoughtfully expanded with a brand-new second floor featuring a private primary suite, a dedicated laundry room, and a total of 3 spacious bedrooms and 2 modern baths. The main level shines with all-new LVP flooring, a modern kitchen boasting sleek new cabinetry, granite countertops, and

    Valerie Brown Coldwell Banker Realty

    311 Maple Ave, Federalsburg, MD 21632
  • 3485 Gallagher Rd, Preston, MD 21655
    3485 Gallagher Rd, Preston, MD 21655
    3485 Gallagher Rd, Preston, MD 21655
    /74

    $740,000

    Sold Jan 20, 2026

    3485 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 3,326 Sq Ft
    • Built 2003

    Last Sold Summary

    • $222/SF
    • 5 Days On Market

    Current Estimated Value $723,377

    Last Listing Agent Alicia Gannon Dulin Benson & Mangold, LLC

    3485 Gallagher Rd, Preston, MD 21655
    • 505 S 2nd St, Denton, MD 21629
      505 S 2nd St, Denton, MD 21629
      505 S 2nd St, Denton, MD 21629
      /11

      Est $303,287

      Not Listed For Sale

      505 S 2nd St, Denton, MD 21629

      • 3 Beds
      • 1.5 Baths
      • 2,058 Sq Ft
      • Built 1941
      505 S 2nd St, Denton, MD 21629

      Last Sold Summary

      • 12 Days On Market

  • 12087 Wayman St, Ridgely, MD 21660
    12087 Wayman St, Ridgely, MD 21660
    /2

    $25,000

    • Land
    • 12,196 Sq Ft
    • $89,286 per Acre

    12087 Wayman St, Ridgely, MD 21660

    Double lot . There are the remains of a house on the property; please leave the remains "as is". Well and septic unknown.

    Bev Langley Coldwell Banker Realty

    12087 Wayman St, Ridgely, MD 21660
  • 8556 Tuckahoe Rd, Denton, MD 21629
    8556 Tuckahoe Rd, Denton, MD 21629
    8556 Tuckahoe Rd, Denton, MD 21629
    /52

    $390,000

    Sold Oct 23, 2025

    8556 Tuckahoe Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2001

    Last Sold Summary

    • $290/SF
    • 42 Days On Market

    Current Estimated Value $382,252

    Last Listing Agent Kathleen Armiger Coldwell Banker Realty

    8556 Tuckahoe Rd, Denton, MD 21629
    • 217 Greenridge Rd, Federalsburg, MD 21632
      217 Greenridge Rd, Federalsburg, MD 21632
      217 Greenridge Rd, Federalsburg, MD 21632
      /20

      Est $223,779

      Not Listed For Sale

      217 Greenridge Rd, Federalsburg, MD 21632

      • 2 Beds
      • 1.5 Baths
      • 1,276 Sq Ft
      • Built 1950
      217 Greenridge Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 2 Days On Market

  • 222 S 2nd St, Denton, MD 21629
    222 S 2nd St, Denton, MD 21629
    222 S 2nd St, Denton, MD 21629
    /41

    $349,000

    $10K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,800 Sq Ft

    222 S 2nd St, Denton, MD 21629

    Welcome to this Charming Colonial Home located on one of the best streets in Denton! Home Features 5 Bedrooms and 2 Full Baths. Home has SO many upgrades!! Main floor has Cozy Living Room, Separate Dining Room, Kitchen that is Bright has lots of Cabinets and tons of Storage. First Floor Primary Bedroom with Access to spacious laundry room and The Outdoors. Upstairs features 3 More Bedrooms and a

    Kathleen Brenton Brenton Realty Group

    222 S 2nd St, Denton, MD 21629
  • 26042 Line Rd, Denton, MD 21629
    26042 Line Rd, Denton, MD 21629
    26042 Line Rd, Denton, MD 21629
    /3

    $80,000

    Sold Sep 02, 2025

    26042 Line Rd, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1970

    Last Sold Summary

    • $111/SF
    • 9 Days On Market

    Last Listing Agent Bonnie Duley Long & Foster Real Estate, Inc.

    26042 Line Rd, Denton, MD 21629
    • 26280 Hobbs Rd, Denton, MD 21629
      26280 Hobbs Rd, Denton, MD 21629
      26280 Hobbs Rd, Denton, MD 21629
      /25

      Est $262,823

      Not Listed For Sale

      26280 Hobbs Rd, Denton, MD 21629

      • 2 Beds
      • 1.5 Baths
      • 960 Sq Ft
      • Built 1983
      26280 Hobbs Rd, Denton, MD 21629

      Last Sold Summary

      • 6 Days On Market

  • 309 N Main St, Greensboro, MD 21639
    309 N Main St, Greensboro, MD 21639
    309 N Main St, Greensboro, MD 21639
    /30

    $299,900

    $20K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,791 Sq Ft

    309 N Main St, Greensboro, MD 21639

    This exquisite Colonial-style home, thoughtfully renovated in 2019, seamlessly blends classic charm with modern luxury. Spanning 1,791 square feet, this residence offers a warm and inviting atmosphere, perfect for creating lasting memories. Step inside to discover a beautifully designed interior featuring engineered luxury vinyl plank flooring that exudes elegance and durability. The heart of the

    Eddie Matthews Benson & Mangold, LLC

    309 N Main St, Greensboro, MD 21639
  • 13800 Cedar Ln, Greensboro, MD 21639
    13800 Cedar Ln, Greensboro, MD 21639
    13800 Cedar Ln, Greensboro, MD 21639
    /104

    $478,000

    Sold Aug 19, 2025

    13800 Cedar Ln, Greensboro, MD 21639

    • 2 Beds
    • 1 Bath
    • 1,372 Sq Ft
    • Built 1920

    Last Sold Summary

    • $348/SF
    • 10 Days On Market

    Current Estimated Value $474,157

    Last Listing Agent Lona Todd Taylor Properties

    13800 Cedar Ln, Greensboro, MD 21639
    • 1104 Ruddy Duck Ct, Denton, MD 21629
      1104 Ruddy Duck Ct, Denton, MD 21629
      1104 Ruddy Duck Ct, Denton, MD 21629
      /50

      Est $382,041

      Not Listed For Sale

      1104 Ruddy Duck Ct, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,577 Sq Ft
      • Built 2005
      1104 Ruddy Duck Ct, Denton, MD 21629

      Last Sold Summary

      • 7 Days On Market

  • 12104 Holly Rd, Ridgely, MD 21660
    12104 Holly Rd, Ridgely, MD 21660
    12104 Holly Rd, Ridgely, MD 21660
    /44

    $595,000

    $30K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    12104 Holly Rd, Ridgely, MD 21660

    Bring your horses and enjoy beautiful, country living just minutes away from town! Conveniently located with easy access to everything the eastern shore has to offer. New kitchen, new bathrooms, and new floors makes this place truly turn-key. Sitting on just over five acres, there's plenty of room to make this place yours. Two spacious paddocks, small barn including two stalls, tack room, water,

    Keith Hensley Meredith Fine Properties

    12104 Holly Rd, Ridgely, MD 21660
  • 17990 Henderson Rd, Marydel, MD 21649
    17990 Henderson Rd, Marydel, MD 21649
    17990 Henderson Rd, Marydel, MD 21649
    /24

    $165,000

    Sold Nov 10, 2025

    17990 Henderson Rd, Marydel, MD 21649

    • 1 Bed
    • 1 Bath
    • 1,527 Sq Ft
    • Built 1973

    Last Sold Summary

    • $108/SF
    • 10 Days On Market

    Current Estimated Value $200,499

    Last Listing Agent Timothy Morgan Keller Williams Realty Delmarva

    17990 Henderson Rd, Marydel, MD 21649
    • 23060 Tuckahoe Springs Dr, Denton, MD 21629
      23060 Tuckahoe Springs Dr, Denton, MD 21629
      23060 Tuckahoe Springs Dr, Denton, MD 21629
      /54

      Est $430,840

      Not Listed For Sale

      23060 Tuckahoe Springs Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,820 Sq Ft
      • Built 1977
      23060 Tuckahoe Springs Dr, Denton, MD 21629

      Last Sold Summary

      • 7 Days On Market

  • 5258 Preston Rd, Federalsburg, MD 21632
    5258 Preston Rd, Federalsburg, MD 21632
    5258 Preston Rd, Federalsburg, MD 21632
    /20

    $225,000

    • 4 Beds
    • 1 Bath
    • 1,350 Sq Ft

    5258 Preston Rd, Federalsburg, MD 21632

    4 bedrooms 1 bathroom bungalow being sold "AS IS". 16,700 sq. ft. lot with detached garage. Priced to Sell.Updated 200. amp electric service.

    Barton Johnson/not int Marshy Hope Realty LLC

    5258 Preston Rd, Federalsburg, MD 21632
  • 26091 Hokum Dr, Greensboro, MD 21639
    26091 Hokum Dr, Greensboro, MD 21639
    26091 Hokum Dr, Greensboro, MD 21639
    /61

    $429,900

    Sold Jan 05, 2026

    26091 Hokum Dr, Greensboro, MD 21639

    • 4 Beds
    • 2.5 Baths
    • 2,248 Sq Ft
    • Built 2004

    Last Sold Summary

    • $191/SF
    • 24 Days On Market

    Current Estimated Value $440,349

    Last Listing Agent Lori Marino Long & Foster Real Estate, Inc.

    26091 Hokum Dr, Greensboro, MD 21639
    • 315 W Sunset Ave, Greensboro, MD 21639
      315 W Sunset Ave, Greensboro, MD 21639
      315 W Sunset Ave, Greensboro, MD 21639
      /50

      Est $355,807

      Not Listed For Sale

      315 W Sunset Ave, Greensboro, MD 21639

      • 4 Beds
      • 2.5 Baths
      • 2,416 Sq Ft
      • Built 1880
      315 W Sunset Ave, Greensboro, MD 21639

      Last Sold Summary

      • 31 Days On Market

  • 1302 Trice Meadows Cir, Denton, MD 21629
    1302 Trice Meadows Cir, Denton, MD 21629
    1302 Trice Meadows Cir, Denton, MD 21629
    /27

    $350,000

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

    1302 Trice Meadows Cir, Denton, MD 21629

    Welcome home to this warm and inviting Rancher situated on a 0.1950-acre lot, offering plenty of space for everyday living, relaxing, and entertaining. This charming home features three bedrooms, an office/den perfect for working from home or a guest space, and two full baths. The kitchen opens to the dining area and family room, creating a wonderful flow for gatherings with family and friends.

    Lori Guimond Keller Williams Select Realtors of Easton

    1302 Trice Meadows Cir, Denton, MD 21629
  • 207 Bloomingdale Ave, Federalsburg, MD 21632
    207 Bloomingdale Ave, Federalsburg, MD 21632
    207 Bloomingdale Ave, Federalsburg, MD 21632
    /43

    $240,000

    Sold May 06, 2026

    207 Bloomingdale Ave, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,684 Sq Ft
    • Built 1953

    Last Sold Summary

    • $143/SF
    • 202 Days On Market

    Current Estimated Value $240,976

    Last Listing Agent Dustin Parker The Parker Group

    207 Bloomingdale Ave, Federalsburg, MD 21632
    • 1211 Cattail Commons Way, Denton, MD 21629
      1211 Cattail Commons Way, Denton, MD 21629
      1211 Cattail Commons Way, Denton, MD 21629
      /44

      Est $422,556

      Not Listed For Sale

      1211 Cattail Commons Way, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,036 Sq Ft
      • Built 2006
      1211 Cattail Commons Way, Denton, MD 21629

      Last Sold Summary

      • 16 Days On Market

  • 412 N Main St, Greensboro, MD 21639
    412 N Main St, Greensboro, MD 21639
    412 N Main St, Greensboro, MD 21639
    /43

    $364,000

    $11K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft

    412 N Main St, Greensboro, MD 21639

    Rare Find! This 3-bedroom, 2-bath renovated rancher offers the perfect blend of space and charm on a sprawling 0.73 acre in-town lot. Spanning over 1,860 sq. ft. of updated living space, you’ll love the openess of the crisp, white kitchen that flows into the cozy light filled living-dining area, the versatile bonus room/office and the entertainment-ready basement with a unique custom bar.

    Karen Clark Clark & Co Realty, LLC

    412 N Main St, Greensboro, MD 21639
  • 610 Lincoln St, Denton, MD 21629
    610 Lincoln St, Denton, MD 21629
    610 Lincoln St, Denton, MD 21629
    /22

    $205,000

    Sold Jun 05, 2026

    610 Lincoln St, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 704 Sq Ft
    • Built 1915

    Last Sold Summary

    • 8% Above List Price
    • $291/SF
    • 14 Days On Market

    Current Estimated Value $185,355

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    610 Lincoln St, Denton, MD 21629
    • 118 Edenton Ln, Denton, MD 21629
      118 Edenton Ln, Denton, MD 21629
      118 Edenton Ln, Denton, MD 21629
      /41

      Est $307,911

      Not Listed For Sale

      118 Edenton Ln, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,479 Sq Ft
      • Built 1975
      118 Edenton Ln, Denton, MD 21629

      Last Sold Summary

      • 113 Days On Market

  • 12115 Lincoln St, Ridgely, MD 21660
    12115 Lincoln St, Ridgely, MD 21660
    /2

    $23,000

    • Land
    • 6,098 Sq Ft
    • $164,286 per Acre

    12115 Lincoln St, Ridgely, MD 21660

    Vacant lot, check with the county about putting a new house on this lot. There was previously a house on this lot.

    Pamela Geib Long & Foster Real Estate, Inc.

    12115 Lincoln St, Ridgely, MD 21660
  • 222 Denton Rd, Federalsburg, MD 21632
    222 Denton Rd, Federalsburg, MD 21632
    222 Denton Rd, Federalsburg, MD 21632
    /3

    $27,500

    Sold Dec 04, 2025

    222 Denton Rd, Federalsburg, MD 21632

    • Land
    • 10,018 Sq Ft
    • $119,565 per Acre

    Last Sold Summary

    • 589 Days On Market

    Current Estimated Value $81,965

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

    222 Denton Rd, Federalsburg, MD 21632
    • 1107 Canvasback Ln, Denton, MD 21629
      1107 Canvasback Ln, Denton, MD 21629
      1107 Canvasback Ln, Denton, MD 21629
      /29

      Est $393,276

      Not Listed For Sale

      1107 Canvasback Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,496 Sq Ft
      • Built 2005
      1107 Canvasback Ln, Denton, MD 21629

      Last Sold Summary

      • 24 Days On Market

Showing Results 521 - 560, Page 14 of 18

Maryland Caroline County

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