15,675

Caroline County, MD Homes

Section Image
    • 23116 Gilpin Point Rd, Preston, MD 21655
      23116 Gilpin Point Rd, Preston, MD 21655
      23116 Gilpin Point Rd, Preston, MD 21655
      /24

      Est $449,671 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,880 Sq Ft

      23116 Gilpin Point Rd, Preston, MD 21655

      23116 Gilpin Point Rd, Preston, MD 21655
  • 21269 Dover Bridge Rd, Preston, MD 21655
    21269 Dover Bridge Rd, Preston, MD 21655
    21269 Dover Bridge Rd, Preston, MD 21655
    /12

    $60,000

    • 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
  • 11489 Reed Cir, Ridgely, MD 21660
    11489 Reed Cir, Ridgely, MD 21660
    11489 Reed Cir, Ridgely, MD 21660
    /46

    $439,500 Sold May 21, 2025

    11489 Reed Cir, Ridgely, MD 21660

    • 4 Beds
    • 2.5 Baths
    • 1,923 Sq Ft
    • Built 1995

    Last Sold Summary

    • $229/SF
    • 31 Days On Market

    Current Estimated Value $476,513

    Last Listing Agent Carol Delayo Chaney Homes, LLC

    11489 Reed Cir, Ridgely, MD 21660
    • 6 W Liberty St, Ridgely, MD 21660
      6 W Liberty St, Ridgely, MD 21660
      6 W Liberty St, Ridgely, MD 21660
      /27

      Est $407,762 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,184 Sq Ft

      6 W Liberty St, Ridgely, MD 21660

      6 W Liberty St, Ridgely, MD 21660
  • 1202 Blue Heron Dr, Denton, MD 21629
    1202 Blue Heron Dr, Denton, MD 21629
    1202 Blue Heron Dr, Denton, MD 21629
    /13

    $235,000 Under Contract

    • 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
  • 116 Stonesifer Dr, Greensboro, MD 21639
    116 Stonesifer Dr, Greensboro, MD 21639
    116 Stonesifer Dr, Greensboro, MD 21639
    /19

    $189,900 Sold Dec 29, 2025

    116 Stonesifer Dr, Greensboro, MD 21639

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft
    • Built 1954

    Last Sold Summary

    • $226/SF
    • 2 Days On Market

    Last Listing Agent Brett Schrader Taylor Properties

    116 Stonesifer Dr, Greensboro, MD 21639
    • 10961 Greensboro Rd, Denton, MD 21629
      10961 Greensboro Rd, Denton, MD 21629
      10961 Greensboro Rd, Denton, MD 21629
      /4

      Est $450,002 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,064 Sq Ft

      10961 Greensboro Rd, Denton, MD 21629

      10961 Greensboro Rd, Denton, MD 21629
  • 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
  • 207 Caroline Ave, Ridgely, MD 21660
    207 Caroline Ave, Ridgely, MD 21660
    207 Caroline Ave, Ridgely, MD 21660
    /17

    $150,000 Sold Apr 30, 2025

    207 Caroline Ave, Ridgely, MD 21660

    • 3 Beds
    • 1.5 Baths
    • 1,008 Sq Ft
    • Built 1890

    Last Sold Summary

    • $149/SF
    • 6 Days On Market

    Current Estimated Value $178,005

    Last Listing Agent Timothy Caropreso Keller Williams Flagship

    207 Caroline Ave, Ridgely, MD 21660
    • 308 Park Ave, Federalsburg, MD 21632
      308 Park Ave, Federalsburg, MD 21632
      308 Park Ave, Federalsburg, MD 21632
      /27

      Est $167,873 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 952 Sq Ft

      308 Park Ave, Federalsburg, MD 21632

      308 Park Ave, Federalsburg, MD 21632
  • 14418 Poplar St, Goldsboro, MD 21636
    14418 Poplar St, Goldsboro, MD 21636
    14418 Poplar St, Goldsboro, MD 21636
    /52

    $444,500 Under Contract

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

    14418 Poplar St, Goldsboro, MD 21636

    This Log cabin rests on over 12 acres of open and wooded land that backs to the Choptank River. Access canoes, kayaks or prepare for waterfowl and deer seasons. The private lane leads to the large White Cedar Cabin with cathedral ceiling in the Great Room that offers an open floor plan. Home features hardwood floors and a separate loft for a bedroom or construction to make more. Spacious Primary

    Roger Boyce Chesapeake Real Estate Associates, LLC

    14418 Poplar St, Goldsboro, MD 21636
  • 8 N Maple Ave, Ridgely, MD 21660
    8 N Maple Ave, Ridgely, MD 21660
    8 N Maple Ave, Ridgely, MD 21660
    /22

    $226,000 Sold May 07, 2025

    8 N Maple Ave, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1977

    Last Sold Summary

    • $214/SF
    • 7 Days On Market

    Current Estimated Value $242,725

    Last Listing Agent Blaine Williamson McClain-Williamson Realty, LLC

    8 N Maple Ave, Ridgely, MD 21660
    • 12141 Greensboro Rd, Greensboro, MD 21639
      12141 Greensboro Rd, Greensboro, MD 21639
      12141 Greensboro Rd, Greensboro, MD 21639
      /3

      Est $484,453 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft

      12141 Greensboro Rd, Greensboro, MD 21639

      12141 Greensboro Rd, Greensboro, MD 21639
  • 207 Bloomingdale Ave, Federalsburg, MD 21632
    207 Bloomingdale Ave, Federalsburg, MD 21632
    207 Bloomingdale Ave, Federalsburg, MD 21632
    /43

    $239,900

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

    207 Bloomingdale Ave, Federalsburg, MD 21632

    Discover this inviting 3-bedroom, 2-bath home on a 0.27-acre lot in the heart of Federalsburg. Enter to a spacious living room filled with natural light and a cozy fireplace, perfect for relaxing or entertaining. Adjacent, the family room features stunning wood-paneled walls, built-in shelving, a second fireplace, and access to both the outdoors and the kitchen and dining areas, creating a

    Dustin Parker The Parker Group

    207 Bloomingdale Ave, Federalsburg, MD 21632
  • 15885 Meeks Rd, Goldsboro, MD 21636
    15885 Meeks Rd, Goldsboro, MD 21636
    15885 Meeks Rd, Goldsboro, MD 21636
    /59

    $389,900 Sold Feb 13, 2025

    15885 Meeks Rd, Goldsboro, MD 21636

    • 3 Beds
    • 1.5 Baths
    • 1,744 Sq Ft
    • Built 1900

    Last Sold Summary

    • $224/SF
    • 200 Days On Market

    Current Estimated Value $407,837

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

    15885 Meeks Rd, Goldsboro, MD 21636
    • 350 Deep Shore Rd, Denton, MD 21629
      350 Deep Shore Rd, Denton, MD 21629
      350 Deep Shore Rd, Denton, MD 21629
      /22

      Est $285,906 Not Listed For Sale

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

      350 Deep Shore Rd, Denton, MD 21629

      350 Deep Shore Rd, Denton, MD 21629
  • 132 Hobbs St, Greensboro, MD 21639
    132 Hobbs St, Greensboro, MD 21639
    132 Hobbs St, Greensboro, MD 21639
    /20

    $265,790 Pending

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

    132 Hobbs St, Greensboro, MD 21639

    **Red Tag Sales Event now through January 25, 2026! Was $268,490 Now: $265,790! Home must close on or before 3/31/2026.** Discover the Perry in Kinnamon Meadows, a 1,059 square foot open concept cottage-style ranch home, offering two bedrooms and two bathrooms at 132 Hobbs Street in Greensboro, MD. A welcoming front porch leads you into the spacious living room that seamlessly flows into the

    Justin K Wood D.R. Horton Realty of Virginia, LLC

    132 Hobbs St, Greensboro, MD 21639
  • 14990 Greensboro Rd, Goldsboro, MD 21636
    14990 Greensboro Rd, Goldsboro, MD 21636
    14990 Greensboro Rd, Goldsboro, MD 21636
    /51

    $400,000 Sold Jan 14, 2026

    14990 Greensboro Rd, Goldsboro, MD 21636

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft
    • Built 1994

    Last Sold Summary

    • $198/SF
    • 58 Days On Market

    Last Listing Agent Andrew Beaven Wright Real Estate

    14990 Greensboro Rd, Goldsboro, MD 21636
    • 319 Kerr Ave, Denton, MD 21629
      319 Kerr Ave, Denton, MD 21629
      319 Kerr Ave, Denton, MD 21629
      /27

      Est $288,975 Not Listed For Sale

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

      319 Kerr Ave, Denton, MD 21629

      319 Kerr Ave, Denton, MD 21629
  • 4218 Harmony Rd, Preston, MD 21655
    4218 Harmony Rd, Preston, MD 21655
    4218 Harmony Rd, Preston, MD 21655
    /127

    $2,999,000

    • 8 Beds
    • 16 Baths
    • 9,364 Sq Ft

    4218 Harmony Rd, Preston, MD 21655

    A truly rare offering for the discerning auto enthusiast, this exceptional 58.48-acre Eastern Shore estate is a masterfully designed luxury compound where architectural elegance meets world-class automotive accommodations. Introduced by a private gated entrance and tree-lined circular drive, the stately brick home immediately conveys the scale, privacy, and prestige of this one-of-a-kind

    Donna Harrington Coldwell Banker Realty

    4218 Harmony Rd, Preston, MD 21655
  • 25266 Smith Landing Rd, Denton, MD 21629
    25266 Smith Landing Rd, Denton, MD 21629
    25266 Smith Landing Rd, Denton, MD 21629
    /43

    $315,000 Sold Sep 15, 2025

    25266 Smith Landing Rd, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 1,256 Sq Ft
    • Built 1953

    Last Sold Summary

    • $251/SF
    • 2 Days On Market

    Last Listing Agent Megan Rosendale Rosendale Realty

    25266 Smith Landing Rd, Denton, MD 21629
    • 111 Maple Ave, Goldsboro, MD 21636
      111 Maple Ave, Goldsboro, MD 21636
      111 Maple Ave, Goldsboro, MD 21636
      /19

      Est $284,746 Not Listed For Sale

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

      111 Maple Ave, Goldsboro, MD 21636

      111 Maple Ave, Goldsboro, MD 21636
  • 4 S 1st St, Denton, MD 21629
    4 S 1st St, Denton, MD 21629
    4 S 1st St, Denton, MD 21629
    /91

    $699,000

    • 3 Beds
    • 4 Baths
    • 2,756 Sq Ft

    4 S 1st St, Denton, MD 21629

    Outstanding Business Opportunity! Rare Find with-in Downtown Denton! Property would make an excellent Restaurant, Bar, great Venue , or a Large Victorian Home! Features include but not limited to Residential, Commerical or Mixed Use. Large Wrap around Porch for entertaining, Patio with plenty of room for seating with Firepit. Park like setting with Open Space and Large Pond! Town ERU's are

    Kathleen Brenton Brenton Realty Group

    4 S 1st St, Denton, MD 21629
  • 25329 Calvert Dr, Greensboro, MD 21639
    25329 Calvert Dr, Greensboro, MD 21639
    25329 Calvert Dr, Greensboro, MD 21639
    /39

    $355,000 Sold Apr 18, 2025

    25329 Calvert Dr, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,688 Sq Ft
    • Built 1990

    Last Sold Summary

    • $210/SF
    • 13 Days On Market

    Current Estimated Value $392,874

    Last Listing Agent Nick Waldner Keller Williams Realty Centre

    25329 Calvert Dr, Greensboro, MD 21639
    • 139 Smugglers Way, Greensboro, MD 21639
      139 Smugglers Way, Greensboro, MD 21639
      139 Smugglers Way, Greensboro, MD 21639
      /26

      Est $277,105 Not Listed For Sale

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

      139 Smugglers Way, Greensboro, MD 21639

      139 Smugglers Way, Greensboro, MD 21639
  • 21245 Tanyard Rd, Preston, MD 21655
    21245 Tanyard Rd, Preston, MD 21655
    21245 Tanyard Rd, Preston, MD 21655
    /10

    $275,000

    • 3 Beds
    • 3 Baths
    • 2,128 Sq Ft

    21245 Tanyard Rd, Preston, MD 21655

    Charming Country Living with Room to Make It Your Own! Welcome to 21245 Tanyard Road, a spacious rancher with 3 bedrooms and 2 full baths nestled on a peaceful 0.62-acre lot in Preston. Built in 1987, this single-level home offers a solid foundation and a functional layout, ready for your personal touch and updates.Whether you're looking for a primary residence or an investment opportunity,

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    21245 Tanyard Rd, Preston, MD 21655
  • 114 Parkland Rd, Greensboro, MD 21639
    114 Parkland Rd, Greensboro, MD 21639
    /2

    $286,990 Sold Sep 24, 2025

    114 Parkland Rd, Greensboro, MD 21639

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

    Last Sold Summary

    • $197/SF
    • 9 Days On Market

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

    114 Parkland Rd, Greensboro, MD 21639
    • 110 Sharp Rd, Denton, MD 21629
      110 Sharp Rd, Denton, MD 21629
      110 Sharp Rd, Denton, MD 21629
      /30

      Est $391,164 Not Listed For Sale

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

      110 Sharp Rd, Denton, MD 21629

      110 Sharp Rd, Denton, MD 21629
  • 28035 Possum Hill Rd, Federalsburg, MD 21632
    28035 Possum Hill Rd, Federalsburg, MD 21632
    28035 Possum Hill Rd, Federalsburg, MD 21632
    /25

    $125,000

    • 2,168 Sq Ft

    28035 Possum Hill Rd, Federalsburg, MD 21632

    Prime Half-Acre Lot Near Smithville Lake – Cleared, with Well and Oversized Garage BayThis unique 0.48-acre property on Possum Hill Rd is ideally situated less than a mile west of the Maryland-Delaware state line, offering a rare combination of open space, infrastructure, and development potential.Property Highlights:Cleared Lot with Existing Well – The land has already been cleared

    Sam Benkirane Proplocate Realty, LLC

    28035 Possum Hill Rd, Federalsburg, MD 21632
  • 27030 Stafford Rd, Marydel, MD 21649
    27030 Stafford Rd, Marydel, MD 21649
    27030 Stafford Rd, Marydel, MD 21649
    /12

    $236,000 Sold Apr 10, 2025

    27030 Stafford Rd, Marydel, MD 21649

    • 3 Beds
    • 1 Bath
    • 1,368 Sq Ft
    • Built 1972

    Last Sold Summary

    • $173/SF
    • 352 Days On Market

    Current Estimated Value $257,824

    Last Listing Agent Myisha Walker Long & Foster Real Estate, Inc.

    27030 Stafford Rd, Marydel, MD 21649
    • 27701 Burrsville Rd, Denton, MD 21629
      27701 Burrsville Rd, Denton, MD 21629
      27701 Burrsville Rd, Denton, MD 21629
      /14

      Est $301,676 Not Listed For Sale

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

      27701 Burrsville Rd, Denton, MD 21629

      27701 Burrsville Rd, Denton, MD 21629
  • 20915 Dover Bridge Rd, Preston, MD 21655
    20915 Dover Bridge Rd, Preston, MD 21655
    20915 Dover Bridge Rd, Preston, MD 21655
    /56

    $497,000

    • 3 Beds
    • 2 Baths
    • 1,904 Sq Ft

    20915 Dover Bridge Rd, Preston, MD 21655

    Set on 8.6 private, fully fenced acres just across the Dover Bridge, this Eastern Shore property offers endless possibilities with scenic surroundings, expansive land, and close proximity to the Choptank River and minutes to Easton. The single-level home features 3 bedrooms and 2 full bathrooms, a country kitchen, and an open-concept layouthighlighted by a massive brick fireplace with insert and

    Alex Martinez The Agency DC

    20915 Dover Bridge Rd, Preston, MD 21655
  • 21596 Dover Bridge Rd, Preston, MD 21655
    21596 Dover Bridge Rd, Preston, MD 21655
    /2

    $99,900 Sold Feb 14, 2025

    21596 Dover Bridge Rd, Preston, MD 21655

    • Land
    • 2.13 Acres
    • $46,901 per Acre

    Last Sold Summary

    • 4 Days On Market

    Current Estimated Value $212,995

    Last Listing Agent Liz Kirkland Iron Valley Real Estate of Central PA

    21596 Dover Bridge Rd, Preston, MD 21655
    • 504 Liberty Rd, Federalsburg, MD 21632
      504 Liberty Rd, Federalsburg, MD 21632
      504 Liberty Rd, Federalsburg, MD 21632
      /36

      Est $265,480 Not Listed For Sale

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

      504 Liberty Rd, Federalsburg, MD 21632

      504 Liberty Rd, Federalsburg, MD 21632
  • 307 Buena Vista Ave, Federalsburg, MD 21632
    307 Buena Vista Ave, Federalsburg, MD 21632
    /2

    $65,000

    • Land
    • 1.75 Acres
    • $37,143 per Acre

    307 Buena Vista Ave, Federalsburg, MD 21632

    Build Your Dream in Federalsburg!Rare opportunity to own a 1.75-acre buildable lot located within the town limits of Federalsburg. This spacious parcel offers the perfect blend of small-town charm and room to breathe—plenty of space for your custom home, garage, and outdoor living without feeling boxed in. Conveniently located near local amenities, schools, and major routes, yet tucked away

    Heather Brummell Keller Williams Realty

    307 Buena Vista Ave, Federalsburg, MD 21632
  • 123 Bloomingdale Ave, Federalsburg, MD 21632
    123 Bloomingdale Ave, Federalsburg, MD 21632
    123 Bloomingdale Ave, Federalsburg, MD 21632
    /31

    $292,900 Sold May 16, 2025

    123 Bloomingdale Ave, Federalsburg, MD 21632

    • 3 Beds
    • 1.5 Baths
    • 1,584 Sq Ft
    • Built 1900

    Last Sold Summary

    • $185/SF
    • 369 Days On Market

    Current Estimated Value $302,534

    Last Listing Agent Marla Baines Meredith Fine Properties

    123 Bloomingdale Ave, Federalsburg, MD 21632
    • 103 Elmor Ct, Greensboro, MD 21639
      103 Elmor Ct, Greensboro, MD 21639
      103 Elmor Ct, Greensboro, MD 21639
      /20

      Est $392,705 Not Listed For Sale

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

      103 Elmor Ct, Greensboro, MD 21639

      103 Elmor Ct, Greensboro, MD 21639
  • 0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660
    /5

    $140,000

    • Land
    • 3.75 Acres
    • $37,333 per Acre

    0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660

    Discover the ideal blend of tranquil nature and prime location! 3.75 acres with mature trees, offering unparalleled privacy and peaceful country living in one of the area's most scenic subdivisions -- all just minutes away from Ridgely and Denton, and less than 1 mile from North Caroline High School. Build your dream home on this beautiful level building lot, providing an even terrain throughout

    Stephan Strothe Washington Fine Properties, LLC

    0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660
  • 17635 Cool Spring Rd, Marydel, MD 21649
    17635 Cool Spring Rd, Marydel, MD 21649
    17635 Cool Spring Rd, Marydel, MD 21649
    /52

    $320,000 Sold Nov 19, 2025

    17635 Cool Spring Rd, Marydel, MD 21649

    • 3 Beds
    • 2 Baths
    • 1,782 Sq Ft
    • Built 1992

    Last Sold Summary

    • $180/SF
    • 18 Days On Market

    Last Listing Agent Daphne Reeve Keller Williams Flagship

    17635 Cool Spring Rd, Marydel, MD 21649
    • 312 Buena Vista Ave, Federalsburg, MD 21632
      312 Buena Vista Ave, Federalsburg, MD 21632
      312 Buena Vista Ave, Federalsburg, MD 21632
      /19

      Est $211,478 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

Showing Results 281 - 320, Page 8 of 18

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