15,698

Caroline County, MD Homes

Section Image
  • 116 Maple Ave, Preston, MD 21655
    116 Maple Ave, Preston, MD 21655
    116 Maple Ave, Preston, MD 21655
    /5

    $238,000 Sold Sep 24, 2025

    116 Maple Ave, Preston, MD 21655

    • 2 Beds
    • 1.5 Baths
    • 1,458 Sq Ft
    • Built 1915

    Last Sold Summary

    • $163/SF
    • 69 Days On Market

    Current Estimated Value $234,692

    Last Listing Agent Mary Haddaway Benson & Mangold, LLC

    116 Maple Ave, Preston, MD 21655
    • 321 S University Ave, Federalsburg, MD 21632
      321 S University Ave, Federalsburg, MD 21632
      321 S University Ave, Federalsburg, MD 21632
      /28

      Est $178,466 Not Listed For Sale

      321 S University Ave, Federalsburg, MD 21632

      • 2 Beds
      • 1 Bath
      • 780 Sq Ft
      • Built 1951
      321 S University Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 2% Below List Price
      • $233/SF
      • 25 Days On Market

      Last Sold Price $182,000

      Last Listing Agent Blaine Williamson McClain-Williamson Realty, LLC

  • E/S MD RT480 Unknown, Hillsboro, MD 21641
    E/S MD RT480 Unknown, Hillsboro, MD 21641
    /2

    $55,000

    • Land
    • 4.17 Acres
    • $13,189 per Acre

    E/S MD RT480 Unknown, Hillsboro, MD 21641

    Seller is waiting for perk results from Caroline county health department

    Diane Wenk Wright Real Estate

    E/S MD RT480 Unknown, Hillsboro, MD 21641
  • 306 Kerr Ave, Denton, MD 21629
    306 Kerr Ave, Denton, MD 21629
    306 Kerr Ave, Denton, MD 21629
    /34

    $386,000 Sold Jun 27, 2025

    306 Kerr Ave, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,064 Sq Ft
    • Built 2005

    Last Sold Summary

    • $187/SF
    • 48 Days On Market

    Current Estimated Value $388,478

    Last Listing Agent Justin Pokrywka Taylor Properties

    306 Kerr Ave, Denton, MD 21629
    • 526 High St, Denton, MD 21629
      526 High St, Denton, MD 21629
      526 High St, Denton, MD 21629
      /17

      Est $207,804 Not Listed For Sale

      526 High St, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 1,232 Sq Ft
      • Built 1890
      526 High St, Denton, MD 21629

      Last Sold Summary

      • 2% Below List Price
      • $172/SF
      • 2 Days On Market

      Last Sold Price $212,000

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • 0 Laurel Grove Unit MDCM2004422, Federalsburg, MD 21632
    0 Laurel Grove Unit MDCM2004422, Federalsburg, MD 21632
    0 Laurel Grove Unit MDCM2004422, Federalsburg, MD 21632
    /8

    $125,100 Sold Jun 12, 2025

    0 Laurel Grove Unit MDCM2004422, Federalsburg, MD 21632

    • Land
    • 9.42 Acres
    • $13,280 per Acre

    Last Sold Summary

    • 291 Days On Market

    Last Listing Agent Diane Wenk Wright Real Estate

    0 Laurel Grove Unit MDCM2004422, Federalsburg, MD 21632
    • 11458 Reed Cir, Ridgely, MD 21660
      11458 Reed Cir, Ridgely, MD 21660
      11458 Reed Cir, Ridgely, MD 21660
      /19

      Est $401,831 Not Listed For Sale

      11458 Reed Cir, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1993
      11458 Reed Cir, Ridgely, MD 21660

      Last Sold Summary

      • 15% Above List Price
      • $243/SF
      • 5 Days On Market

      Last Sold Price $349,500

      Last Listing Agent Chris Rosendale CR Realty

  • 1110 Osprey Ln, Denton, MD 21629
    1110 Osprey Ln, Denton, MD 21629
    1110 Osprey Ln, Denton, MD 21629
    /70

    $398,000 Sold Jun 27, 2025

    1110 Osprey Ln, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,650 Sq Ft
    • Built 2005

    Last Sold Summary

    • $150/SF
    • 3 Days On Market

    Current Estimated Value $407,780

    Last Listing Agent Judith Germain Benson & Mangold, LLC

    1110 Osprey Ln, Denton, MD 21629
    • 23 Lister Ln, Ridgely, MD 21660
      23 Lister Ln, Ridgely, MD 21660
      23 Lister Ln, Ridgely, MD 21660
      /42

      Est $448,011 Not Listed For Sale

      23 Lister Ln, Ridgely, MD 21660

      • 5 Beds
      • 4.5 Baths
      • 3,441 Sq Ft
      • Built 2005
      23 Lister Ln, Ridgely, MD 21660

      Last Sold Summary

      • 6% Above List Price
      • $123/SF
      • 59 Days On Market

      Last Sold Price $423,000

      Last Listing Agent Diane Donnelly Keller Williams Flagship

  • 3181 Gallagher Rd, Preston, MD 21655
    3181 Gallagher Rd, Preston, MD 21655
    3181 Gallagher Rd, Preston, MD 21655
    /15

    $265,000 Sold Aug 20, 2025

    3181 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1990

    Last Sold Summary

    • $237/SF
    • 23 Days On Market

    Current Estimated Value $271,893

    Last Listing Agent Andrew Beaven Wright Real Estate

    3181 Gallagher Rd, Preston, MD 21655
    • 27515 Anthony Mill Rd, Denton, MD 21629
      27515 Anthony Mill Rd, Denton, MD 21629
      27515 Anthony Mill Rd, Denton, MD 21629
      /15

      Est $62,532 Not Listed For Sale

      27515 Anthony Mill Rd, Denton, MD 21629

      27515 Anthony Mill Rd, Denton, MD 21629

      Last Sold Summary

      • 5% Above List Price
      • 14 Days On Market

      Last Sold Price $59,500

      Last Listing Agent Gretchen Wichlinski Compass

  • 123 Parkland Rd, Greensboro, MD 21639
    123 Parkland Rd, Greensboro, MD 21639
    /2

    $269,950 Sold Jan 23, 2026

    123 Parkland Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 2025

    Last Sold Summary

    • $228/SF
    • 85 Days On Market

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

    123 Parkland Rd, Greensboro, MD 21639
    • 304 Kerr Ave, Denton, MD 21629
      304 Kerr Ave, Denton, MD 21629
      304 Kerr Ave, Denton, MD 21629
      /15

      Est $344,174 Not Listed For Sale

      304 Kerr Ave, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,808 Sq Ft
      • Built 2005
      304 Kerr Ave, Denton, MD 21629

      Last Sold Summary

      • 4% Above List Price
      • $183/SF
      • 25 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Linda Moore Long & Foster

  • 205 New St, Goldsboro, MD 21636
    205 New St, Goldsboro, MD 21636
    205 New St, Goldsboro, MD 21636
    /7

    $55,000 Sold Mar 20, 2026

    205 New St, Goldsboro, MD 21636

    • Land
    • 0.58 Acre
    • $94,828 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $79,377

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    205 New St, Goldsboro, MD 21636
    • 22081 Dover Bridge Rd, Preston, MD 21655
      22081 Dover Bridge Rd, Preston, MD 21655
      22081 Dover Bridge Rd, Preston, MD 21655
      /15

      Est $211,798 Not Listed For Sale

      22081 Dover Bridge Rd, Preston, MD 21655

      • 3 Beds
      • 1 Bath
      • 1,252 Sq Ft
      • Built 1954
      22081 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • 6% Above List Price
      • $160/SF
      • 25 Days On Market

      Last Sold Price $200,000

      Last Listing Agent Pamela Price Berkshire Hathaway HomeServices PenFed Realty

  • 15 Ridgeway Dr, Ridgely, MD 21660
    15 Ridgeway Dr, Ridgely, MD 21660
    15 Ridgeway Dr, Ridgely, MD 21660
    /30

    $354,900 Sold Sep 12, 2025

    15 Ridgeway Dr, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 2009

    Last Sold Summary

    • $228/SF
    • 53 Days On Market

    Current Estimated Value $347,378

    Last Listing Agent Jarnell Foster Benson & Mangold, LLC

    15 Ridgeway Dr, Ridgely, MD 21660
    • 5577 Harmony Woods Dr, Preston, MD 21655
      5577 Harmony Woods Dr, Preston, MD 21655
      5577 Harmony Woods Dr, Preston, MD 21655
      /47

      Est $488,503 Not Listed For Sale

      5577 Harmony Woods Dr, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 2,526 Sq Ft
      • Built 2006
      5577 Harmony Woods Dr, Preston, MD 21655

      Last Sold Summary

      • 6% Above List Price
      • $182/SF
      • 21 Days On Market

      Last Sold Price $459,000

      Last Listing Agent Ed Quidas Long & Foster

  • 15551 Wharton Rd, Goldsboro, MD 21636
    15551 Wharton Rd, Goldsboro, MD 21636
    15551 Wharton Rd, Goldsboro, MD 21636
    /80

    $804,000 Sold Nov 26, 2025

    15551 Wharton Rd, Goldsboro, MD 21636

    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft
    • Built 1850

    Last Sold Summary

    • $372/SF
    • 40 Days On Market

    Current Estimated Value $778,713

    Last Listing Agent Heather Branham The Parker Group

    15551 Wharton Rd, Goldsboro, MD 21636
    • 109 Sunset Blvd, Preston, MD 21655
      109 Sunset Blvd, Preston, MD 21655
      109 Sunset Blvd, Preston, MD 21655
      /46

      Est $359,509 Not Listed For Sale

      109 Sunset Blvd, Preston, MD 21655

      • 3 Beds
      • 1.5 Baths
      • 1,632 Sq Ft
      • Built 1965
      109 Sunset Blvd, Preston, MD 21655

      Last Sold Summary

      • 12% Above List Price
      • $196/SF
      • 3 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Josh Rose LAIRD & ASSOCIATES

  • 23792 Bridgetown Rd, Henderson, MD 21640
    23792 Bridgetown Rd, Henderson, MD 21640
    23792 Bridgetown Rd, Henderson, MD 21640
    /70

    $500,000 Sold Apr 23, 2025

    23792 Bridgetown Rd, Henderson, MD 21640

    • 3 Beds
    • 3.5 Baths
    • 2,375 Sq Ft
    • Built 1987

    Last Sold Summary

    • $211/SF
    • 6 Days On Market

    Current Estimated Value $505,247

    Last Listing Agent Chris Rosendale CR Realty

    23792 Bridgetown Rd, Henderson, MD 21640
    • 1311 Fairfield Ct, Denton, MD 21629
      1311 Fairfield Ct, Denton, MD 21629
      1311 Fairfield Ct, Denton, MD 21629
      /15

      Est $305,973 Not Listed For Sale

      1311 Fairfield Ct, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,360 Sq Ft
      • Built 2003
      1311 Fairfield Ct, Denton, MD 21629

      Last Sold Summary

      • 1% Above List Price
      • $224/SF
      • 6 Days On Market

      Last Sold Price $304,000

      Last Listing Agent Chad Robertson Compass

  • 24656 White Dogwood Dr, Denton, MD 21629
    24656 White Dogwood Dr, Denton, MD 21629
    24656 White Dogwood Dr, Denton, MD 21629
    /46

    $637,000 Sold May 30, 2025

    24656 White Dogwood Dr, Denton, MD 21629

    • 6 Beds
    • 3 Baths
    • 4,064 Sq Ft
    • Built 1999

    Last Sold Summary

    • $157/SF
    • 40 Days On Market

    Current Estimated Value $649,912

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    24656 White Dogwood Dr, Denton, MD 21629
    • 1208 Blue Heron Dr, Denton, MD 21629
      1208 Blue Heron Dr, Denton, MD 21629
      1208 Blue Heron Dr, Denton, MD 21629
      /30

      Est $227,570 Not Listed For Sale

      1208 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,560 Sq Ft
      • Built 2004
      1208 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 12% Above List Price
      • $131/SF

      Last Sold Price $204,000

      Last Listing Agent Judith Germain Benson & Mangold, LLC

  • 122 Julie Ln, Federalsburg, MD 21632
    122 Julie Ln, Federalsburg, MD 21632
    122 Julie Ln, Federalsburg, MD 21632
    /28

    $214,990 Sold Sep 12, 2025

    122 Julie Ln, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Last Sold Summary

    • $158/SF
    • 19 Days On Market

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

    122 Julie Ln, Federalsburg, MD 21632
    • 23079 Tuckahoe Springs Dr, Denton, MD 21629
      23079 Tuckahoe Springs Dr, Denton, MD 21629
      23079 Tuckahoe Springs Dr, Denton, MD 21629
      /62

      Est $704,066 Not Listed For Sale

      23079 Tuckahoe Springs Dr, Denton, MD 21629

      • 3 Beds
      • 4 Baths
      • 3,737 Sq Ft
      • Built 1974
      23079 Tuckahoe Springs Dr, Denton, MD 21629

      Last Sold Summary

      • 8% Above List Price
      • $174/SF
      • 112 Days On Market

      Last Sold Price $650,000

      Last Listing Agent Melanie Hopkins Coldwell Banker Chesapeake Real Estate Company

  • 314 Kerr Ave, Denton, MD 21629
    314 Kerr Ave, Denton, MD 21629
    314 Kerr Ave, Denton, MD 21629
    /19

    $340,000 Sold Dec 05, 2025

    314 Kerr Ave, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,764 Sq Ft
    • Built 1984

    Last Sold Summary

    • $193/SF
    • 4 Days On Market

    Current Estimated Value $350,584

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

    314 Kerr Ave, Denton, MD 21629
    • 208 N Academy St, Greensboro, MD 21639
      208 N Academy St, Greensboro, MD 21639
      208 N Academy St, Greensboro, MD 21639
      /10

      Est $170,694 Not Listed For Sale

      208 N Academy St, Greensboro, MD 21639

      • 2 Beds
      • 1 Bath
      • 1,236 Sq Ft
      • Built 1925
      208 N Academy St, Greensboro, MD 21639

      Last Sold Summary

      • 171% Above List Price
      • $51/SF
      • 18 Days On Market

      Last Sold Price $63,000

      Last Listing Agent Pamela Geib Long & Foster

  • 112 Riverwalk Terrace, Federalsburg, MD 21632
    112 Riverwalk Terrace, Federalsburg, MD 21632
    112 Riverwalk Terrace, Federalsburg, MD 21632
    /27

    $209,990 Sold May 05, 2025

    112 Riverwalk Terrace, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2024

    Last Sold Summary

    • $154/SF
    • 84 Days On Market

    Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

    112 Riverwalk Terrace, Federalsburg, MD 21632
    • 26220 Shore Hwy, Denton, MD 21629
      26220 Shore Hwy, Denton, MD 21629
      26220 Shore Hwy, Denton, MD 21629
      /3

      Est $283,408 Not Listed For Sale

      26220 Shore Hwy, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,104 Sq Ft
      • Built 1977
      26220 Shore Hwy, Denton, MD 21629

      Last Sold Summary

      • 16% Above List Price
      • $222/SF
      • 7 Days On Market

      Last Sold Price $245,000

      Last Listing Agent Sheila Washburn Benson & Mangold, LLC

  • 8548 Dogwood Blossom Ln, Denton, MD 21629
    8548 Dogwood Blossom Ln, Denton, MD 21629
    8548 Dogwood Blossom Ln, Denton, MD 21629
    /46

    $365,000 Sold Jan 27, 2026

    8548 Dogwood Blossom Ln, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,176 Sq Ft
    • Built 1988

    Last Sold Summary

    • $168/SF
    • 63 Days On Market

    Current Estimated Value $387,548

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    8548 Dogwood Blossom Ln, Denton, MD 21629
    • 6105 Laurel Grove Rd, Denton, MD 21629
      6105 Laurel Grove Rd, Denton, MD 21629
      6105 Laurel Grove Rd, Denton, MD 21629
      /26

      Est $639,756 Not Listed For Sale

      6105 Laurel Grove Rd, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 1988
      6105 Laurel Grove Rd, Denton, MD 21629

      Last Sold Summary

      • 21% Above List Price
      • $351/SF
      • 301 Days On Market

      Last Sold Price $530,000

      Last Listing Agent Mickey Hayward Sunset Properties

  • 115 Parkland Rd, Greensboro, MD 21639
    115 Parkland Rd, Greensboro, MD 21639
    /2

    $276,990 Sold Oct 17, 2025

    115 Parkland Rd, Greensboro, MD 21639

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

    Last Sold Summary

    • $234/SF
    • 22 Days On Market

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

    115 Parkland Rd, Greensboro, MD 21639
    • 1706 Blue Heron Dr, Denton, MD 21629
      1706 Blue Heron Dr, Denton, MD 21629
      1706 Blue Heron Dr, Denton, MD 21629
      /24

      Est $236,629 Not Listed For Sale

      1706 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,560 Sq Ft
      • Built 2005
      1706 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 3% Above List Price
      • $147/SF
      • 13 Days On Market

      Last Sold Price $230,000

      Last Listing Agent Mark McGuire Benson & Mangold, LLC

  • 206 Charles St, Federalsburg, MD 21632
    206 Charles St, Federalsburg, MD 21632
    206 Charles St, Federalsburg, MD 21632
    /35

    $335,000 Sold Feb 06, 2026

    206 Charles St, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,734 Sq Ft
    • Built 1995

    Last Sold Summary

    • $193/SF
    • 64 Days On Market

    Current Estimated Value $349,413

    Last Listing Agent Rosezette Dennis Coldwell Banker Realty

    206 Charles St, Federalsburg, MD 21632
    • 403 Mallard Dr, Greensboro, MD 21639
      403 Mallard Dr, Greensboro, MD 21639
      403 Mallard Dr, Greensboro, MD 21639
      /59

      Est $310,270 Not Listed For Sale

      403 Mallard Dr, Greensboro, MD 21639

      • 3 Beds
      • 2.5 Baths
      • 1,456 Sq Ft
      • Built 2005
      403 Mallard Dr, Greensboro, MD 21639

      Last Sold Summary

      • 13% Above List Price
      • $189/SF
      • 30 Days On Market

      Last Sold Price $274,990

      Last Listing Agent Angela Demattia BHHS PenFed (actual)

  • 23956 Willow Pond Rd, Denton, MD 21629
    23956 Willow Pond Rd, Denton, MD 21629
    23956 Willow Pond Rd, Denton, MD 21629
    /107

    $680,000 Sold Mar 31, 2025

    23956 Willow Pond Rd, Denton, MD 21629

    • 4 Beds
    • 2 Baths
    • 2,888 Sq Ft
    • Built 1955

    Last Sold Summary

    • $235/SF
    • 22 Days On Market

    Current Estimated Value $691,027

    Last Listing Agent Chris Rosendale CR Realty

    23956 Willow Pond Rd, Denton, MD 21629
    • 112 Carolin Ct, Preston, MD 21655
      112 Carolin Ct, Preston, MD 21655
      112 Carolin Ct, Preston, MD 21655
      /11

      Est $285,253 Not Listed For Sale

      112 Carolin Ct, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1977
      112 Carolin Ct, Preston, MD 21655

      Last Sold Summary

      • 12% Above List Price
      • $207/SF
      • 52 Days On Market

      Last Sold Price $255,000

      Last Listing Agent Andrew Beaven Wright Real Estate

  • 17840 Cool Spring Rd, Marydel, MD 21649
    17840 Cool Spring Rd, Marydel, MD 21649
    17840 Cool Spring Rd, Marydel, MD 21649
    /8

    $329,000 Sold Jun 23, 2025

    17840 Cool Spring Rd, Marydel, MD 21649

    • 4 Beds
    • 2 Baths
    • 1,568 Sq Ft
    • Built 1994

    Last Sold Summary

    • $210/SF
    • 0 Days On Market

    Current Estimated Value $338,154

    Last Listing Agent Amanda Morgan Brenton Realty Group

    17840 Cool Spring Rd, Marydel, MD 21649
    • 25778 Herring Ln, Denton, MD 21629
      25778 Herring Ln, Denton, MD 21629
      25778 Herring Ln, Denton, MD 21629
      /30

      Est $480,652 Not Listed For Sale

      25778 Herring Ln, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,608 Sq Ft
      • Built 1989
      25778 Herring Ln, Denton, MD 21629

      Last Sold Summary

      • 1% Below List Price
      • $302/SF
      • 19 Days On Market

      Last Sold Price $485,000

      Last Listing Agent Bonnie Johnson Keller Williams Realty

  • 307 Buena Vista Ave, Federalsburg, MD 21632
    307 Buena Vista Ave, Federalsburg, MD 21632
    /2

    $53,000 Sold Mar 16, 2026

    307 Buena Vista Ave, Federalsburg, MD 21632

    • Land
    • 1.75 Acres
    • $30,286 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 18 Days On Market

    Current Estimated Value $118,648

    Last Listing Agent Heather Brummell Keller Williams Realty

    307 Buena Vista Ave, Federalsburg, MD 21632

Showing Results 561 - 600, Page 15 of 18

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