400

Recently Sold Caroline County MD Homes

Section Image Section Image
  • 23678 Willow Pond Rd, Denton, MD 21629
    23678 Willow Pond Rd, Denton, MD 21629
    23678 Willow Pond Rd, Denton, MD 21629
    /51

    $480,000 Sold Nov 17, 2025

    23678 Willow Pond Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2004

    Last Sold Summary

    • $390/SF
    • 38 Days On Market

    Current Estimated Value $486,556

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    23678 Willow Pond Rd, Denton, MD 21629
  • 24771 Woods Dr, Denton, MD 21629
    24771 Woods Dr, Denton, MD 21629
    24771 Woods Dr, Denton, MD 21629
    /22

    $399,900 Sold Jun 27, 2025

    24771 Woods Dr, Denton, MD 21629

    • 3 Beds
    • 3 Baths
    • 1,816 Sq Ft
    • Built 1991

    Last Sold Summary

    • $220/SF
    • 2 Days On Market

    Current Estimated Value $404,093

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    24771 Woods Dr, Denton, MD 21629
  • 1208 Painted Fern Rd, Denton, MD 21629
    1208 Painted Fern Rd, Denton, MD 21629
    1208 Painted Fern Rd, Denton, MD 21629
    /57

    $405,000 Sold Jul 25, 2025

    1208 Painted Fern Rd, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,994 Sq Ft
    • Built 2006

    Last Sold Summary

    • $135/SF
    • 20 Days On Market

    Current Estimated Value $404,907

    Last Listing Agent Barbara McCaffrey Redfin Corp

    1208 Painted Fern Rd, Denton, MD 21629
  • 307 Academy Ave, Denton, MD 21629
    307 Academy Ave, Denton, MD 21629
    307 Academy Ave, Denton, MD 21629
    /11

    $130,000 Sold Jan 23, 2026

    307 Academy Ave, Denton, MD 21629

    • 2 Beds
    • 1.5 Baths
    • 1,196 Sq Ft
    • Built 1989

    Last Sold Summary

    • 7% Below List Price
    • $109/SF
    • 11 Days On Market

    Current Estimated Value $156,912

    Last Listing Agent Karla Wieland-Cherry Meredith Fine Properties

    307 Academy Ave, Denton, MD 21629
  • 10803 Greensboro Rd, Denton, MD 21629
    10803 Greensboro Rd, Denton, MD 21629
    10803 Greensboro Rd, Denton, MD 21629
    /44

    $390,000 Sold Jul 31, 2025

    10803 Greensboro Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,228 Sq Ft
    • Built 2014

    Last Sold Summary

    • $318/SF
    • 13 Days On Market

    Current Estimated Value $386,129

    Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    10803 Greensboro Rd, Denton, MD 21629
  • 105 Liberty Rd, Federalsburg, MD 21632
    105 Liberty Rd, Federalsburg, MD 21632
    105 Liberty Rd, Federalsburg, MD 21632
    /52

    $230,000 Sold Jun 04, 2025

    105 Liberty Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,988 Sq Ft
    • Built 1900

    Last Sold Summary

    • $116/SF
    • 15 Days On Market

    Current Estimated Value $237,417

    Last Listing Agent Brooke Tephabock LPT Realty, LLC

    105 Liberty Rd, Federalsburg, MD 21632
  • 278 Wood Duck Dr, Greensboro, MD 21639
    278 Wood Duck Dr, Greensboro, MD 21639
    278 Wood Duck Dr, Greensboro, MD 21639
    /31

    $290,000 Sold Jul 25, 2025

    278 Wood Duck Dr, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,265 Sq Ft
    • Built 2024

    Last Sold Summary

    • $229/SF
    • 102 Days On Market

    Last Listing Agent Crystal Smith RE/MAX Executive

    278 Wood Duck Dr, Greensboro, MD 21639
  • 213 W Central Ave, Federalsburg, MD 21632
    213 W Central Ave, Federalsburg, MD 21632
    213 W Central Ave, Federalsburg, MD 21632
    /28

    $175,000 Sold Oct 30, 2025

    213 W Central Ave, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Built 1920

    Last Sold Summary

    • $250/SF
    • 194 Days On Market

    Current Estimated Value $186,823

    Last Listing Agent Cheri Bruce-Phipps TTR Sotheby's International Realty

    213 W Central Ave, Federalsburg, MD 21632
  • 403 W 4th St, Ridgely, MD 21660
    403 W 4th St, Ridgely, MD 21660
    /2

    $450,000 Sold Apr 14, 2025

    403 W 4th St, Ridgely, MD 21660

    • Studio
    • 2,880 Sq Ft
    • Built 1988

    Last Sold Summary

    • $156/SF
    • 87 Days On Market

    Last Listing Agent BJ Kilby Eastern Shore Real Estate, LLC

    403 W 4th St, Ridgely, MD 21660
  • 24905 Holsinger Ln, Ridgely, MD 21660
    24905 Holsinger Ln, Ridgely, MD 21660
    24905 Holsinger Ln, Ridgely, MD 21660
    /59

    $415,000 Sold May 23, 2025

    24905 Holsinger Ln, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2016

    Last Sold Summary

    • $277/SF
    • 46 Days On Market

    Current Estimated Value $409,807

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

    24905 Holsinger Ln, Ridgely, MD 21660
  • 14706 Cherry Ln, Ridgely, MD 21660
    14706 Cherry Ln, Ridgely, MD 21660
    14706 Cherry Ln, Ridgely, MD 21660
    /17

    $240,000 Sold Nov 14, 2025

    14706 Cherry Ln, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 2,546 Sq Ft
    • Built 1979

    Last Sold Summary

    • $94/SF
    • 218 Days On Market

    Current Estimated Value $287,916

    Last Listing Agent Ingrid Butler CENTURY 21 New Millennium

    14706 Cherry Ln, Ridgely, MD 21660
  • 1302 Blue Heron Dr, Denton, MD 21629
    1302 Blue Heron Dr, Denton, MD 21629
    1302 Blue Heron Dr, Denton, MD 21629
    /10

    $222,500 Sold Jul 18, 2025

    1302 Blue Heron Dr, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,753 Sq Ft
    • Built 2004

    Last Sold Summary

    • $127/SF
    • 114 Days On Market

    Current Estimated Value $230,085

    Last Listing Agent Mona Mohr Long & Foster Real Estate, Inc.

    1302 Blue Heron Dr, Denton, MD 21629
  • 306 S 2nd St, Denton, MD 21629
    306 S 2nd St, Denton, MD 21629
    306 S 2nd St, Denton, MD 21629
    /43

    $399,000 Sold Sep 26, 2025

    306 S 2nd St, Denton, MD 21629

    • 5 Beds
    • 2.5 Baths
    • 2,267 Sq Ft
    • Built 1962

    Last Sold Summary

    • $176/SF
    • 9 Days On Market

    Current Estimated Value $387,370

    Last Listing Agent Jana Meredith Meredith Fine Properties

    306 S 2nd St, Denton, MD 21629
  • 21710 Marsh Creek Rd, Preston, MD 21655
    21710 Marsh Creek Rd, Preston, MD 21655
    21710 Marsh Creek Rd, Preston, MD 21655
    /39

    $907,650 Sold Jun 23, 2025

    21710 Marsh Creek Rd, Preston, MD 21655

    • 4 Beds
    • 3 Baths
    • 3,648 Sq Ft
    • Built 1974

    Last Sold Summary

    • $249/SF
    • 12 Days On Market

    Current Estimated Value $880,303

    Last Listing Agent Ed Quidas Long & Foster Real Estate, Inc.

    21710 Marsh Creek Rd, Preston, MD 21655
  • 1706 Cattail Commons Way, Denton, MD 21629
    1706 Cattail Commons Way, Denton, MD 21629
    1706 Cattail Commons Way, Denton, MD 21629
    /46

    $373,000 Sold May 20, 2025

    1706 Cattail Commons Way, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 3,136 Sq Ft
    • Built 2007

    Last Sold Summary

    • $119/SF
    • 56 Days On Market

    Current Estimated Value $394,973

    Last Listing Agent Katie Revels Cummings & Co. Realtors

    1706 Cattail Commons Way, Denton, MD 21629
  • 103 Reliance Ave, Federalsburg, MD 21632
    103 Reliance Ave, Federalsburg, MD 21632
    103 Reliance Ave, Federalsburg, MD 21632
    /10

    $100,000 Sold Aug 12, 2025

    103 Reliance Ave, Federalsburg, MD 21632

    • 3 Beds
    • 1.5 Baths
    • 1,423 Sq Ft
    • Built 1900

    Last Sold Summary

    • $70/SF
    • 61 Days On Market

    Current Estimated Value $132,803

    Last Listing Agent rachael harrison Coldwell Banker Realty

    103 Reliance Ave, Federalsburg, MD 21632
  • 2612 Meadowbrook Rd, Federalsburg, MD 21632
    2612 Meadowbrook Rd, Federalsburg, MD 21632
    2612 Meadowbrook Rd, Federalsburg, MD 21632
    /102

    $325,000 Sold Apr 11, 2025

    2612 Meadowbrook Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 3,476 Sq Ft
    • Built 1987

    Last Sold Summary

    • $93/SF
    • 174 Days On Market

    Current Estimated Value $317,909

    Last Listing Agent Blaine Williamson McClain-Williamson Realty, LLC

    2612 Meadowbrook Rd, Federalsburg, MD 21632
  • 11891 Central Ave, Ridgely, MD 21660
    11891 Central Ave, Ridgely, MD 21660
    11891 Central Ave, Ridgely, MD 21660
    /15

    $315,000 Sold Jun 19, 2025

    11891 Central Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • Built 1981

    Last Sold Summary

    • $192/SF
    • 26 Days On Market

    Current Estimated Value $324,024

    Last Listing Agent Andrew Beaven Wright Real Estate

    11891 Central Ave, Ridgely, MD 21660
  • 118 Parkland Rd, Greensboro, MD 21639

    $275,990 Sold Aug 15, 2025

    118 Parkland Rd, Greensboro, MD 21639

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

    Move in Ready Sold Summary

    • $233/SF
    • 10 Days On Market

    D.R. Horton Kinnamon Meadows

    118 Parkland Rd, Greensboro, MD 21639
  • 15229 Westbridge Ct, Henderson, MD 21640
    15229 Westbridge Ct, Henderson, MD 21640
    /2

    $355,000 Sold Sep 15, 2025

    15229 Westbridge Ct, Henderson, MD 21640

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • Built 2000

    Last Sold Summary

    • $269/SF

    Current Estimated Value $356,828

    Last Listing Agent Barbara Blosser Long & Foster Real Estate, Inc.

    15229 Westbridge Ct, Henderson, MD 21640
  • 104 Hobbs St, Greensboro, MD 21639
    104 Hobbs St, Greensboro, MD 21639
    104 Hobbs St, Greensboro, MD 21639
    /34

    $265,000 Sold Sep 30, 2025

    104 Hobbs St, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Built 2024

    Last Sold Summary

    • $212/SF
    • 14 Days On Market

    Current Estimated Value $265,462

    Last Listing Agent Brett Schrader Taylor Properties

    104 Hobbs St, Greensboro, MD 21639
  • 12680 Greensboro Rd, Greensboro, MD 21639
    12680 Greensboro Rd, Greensboro, MD 21639
    12680 Greensboro Rd, Greensboro, MD 21639
    /36

    $229,000 Sold Oct 30, 2025

    12680 Greensboro Rd, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1967

    Last Sold Summary

    • $318/SF
    • 4 Days On Market

    Current Estimated Value $227,118

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    12680 Greensboro Rd, Greensboro, MD 21639
  • 21498 Dover Bridge Rd, Preston, MD 21655
    21498 Dover Bridge Rd, Preston, MD 21655
    21498 Dover Bridge Rd, Preston, MD 21655
    /33

    $1,050,000 Sold Aug 15, 2025

    21498 Dover Bridge Rd, Preston, MD 21655

    • 3 Beds
    • 3 Baths
    • 2,748 Sq Ft
    • Built 1954

    Last Sold Summary

    • $382/SF
    • 162 Days On Market

    Current Estimated Value $1,140,183

    Last Listing Agent SCOTT REAGAN CALLAWAY FARNELL AND MOORE

    21498 Dover Bridge Rd, Preston, MD 21655
  • 21968 Main St, Hillsboro, MD 21641
    21968 Main St, Hillsboro, MD 21641
    21968 Main St, Hillsboro, MD 21641
    /40

    $325,000 Sold Jun 17, 2025

    21968 Main St, Hillsboro, MD 21641

    • 4 Beds
    • 2 Baths
    • 2,704 Sq Ft
    • Built 1900

    Last Sold Summary

    • $120/SF
    • 6 Days On Market

    Current Estimated Value $328,116

    Last Listing Agent Ross Hunsberger Coldwell Banker Realty

    21968 Main St, Hillsboro, MD 21641
  • 107 Butler Dr, Denton, MD 21629
    107 Butler Dr, Denton, MD 21629
    107 Butler Dr, Denton, MD 21629
    /59

    $359,000 Sold Oct 14, 2025

    107 Butler Dr, Denton, MD 21629

    • 4 Beds
    • 1.5 Baths
    • 2,974 Sq Ft
    • Built 1950

    Last Sold Summary

    • $121/SF
    • 61 Days On Market

    Current Estimated Value $346,223

    Last Listing Agent Justin Pokrywka Taylor Properties

    107 Butler Dr, Denton, MD 21629
  • 207 Gay St, Denton, MD 21629
    207 Gay St, Denton, MD 21629
    207 Gay St, Denton, MD 21629
    /25

    $240,000 Sold Dec 15, 2025

    207 Gay St, Denton, MD 21629

    • Studio
    • 1,820 Sq Ft
    • Built 1885

    Last Sold Summary

    • $132/SF
    • 35 Days On Market

    Last Listing Agent Andrew Beaven Wright Real Estate

    207 Gay St, Denton, MD 21629
  • 25035 Auction Rd, Denton, MD 21629
    25035 Auction Rd, Denton, MD 21629
    25035 Auction Rd, Denton, MD 21629
    /20

    $60,000 Sold Nov 25, 2025

    25035 Auction Rd, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1976

    Last Sold Summary

    • $78/SF
    • 216 Days On Market

    Last Listing Agent Michael Shipley Benson & Mangold, LLC.

    25035 Auction Rd, Denton, MD 21629
  • 14857 Oakland Rd, Ridgely, MD 21660
    14857 Oakland Rd, Ridgely, MD 21660
    14857 Oakland Rd, Ridgely, MD 21660
    /14

    $270,000 Sold Feb 27, 2026

    14857 Oakland Rd, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1967

    Last Sold Summary

    • $375/SF
    • 3 Days On Market

    Current Estimated Value $287,493

    Last Listing Agent VALENCIA BOYD Keller Williams Preferred Properties

    14857 Oakland Rd, Ridgely, MD 21660
  • 13870 Drapers Mill Rd, Greensboro, MD 21639
    13870 Drapers Mill Rd, Greensboro, MD 21639
    13870 Drapers Mill Rd, Greensboro, MD 21639
    /17

    $90,000 Sold Apr 30, 2025

    13870 Drapers Mill Rd, Greensboro, MD 21639

    • Land
    • 2.44 Acres
    • $36,885 per Acre

    Last Sold Summary

    • 3 Days On Market

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    13870 Drapers Mill Rd, Greensboro, MD 21639
  • 603 W Sunset Ave, Greensboro, MD 21639
    603 W Sunset Ave, Greensboro, MD 21639
    603 W Sunset Ave, Greensboro, MD 21639
    /14

    $175,950 Sold Nov 12, 2025

    603 W Sunset Ave, Greensboro, MD 21639

    • Studio
    • 1,983 Sq Ft
    • Built 1900

    Last Sold Summary

    • $89/SF
    • 183 Days On Market

    Current Estimated Value $192,876

    Last Listing Agent Scott Judy Coldwell Banker Waterman Realty

    603 W Sunset Ave, Greensboro, MD 21639
  • 25291 Calvert Dr, Greensboro, MD 21639
    25291 Calvert Dr, Greensboro, MD 21639
    25291 Calvert Dr, Greensboro, MD 21639
    /35

    $320,000 Sold Jan 30, 2026

    25291 Calvert Dr, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1990

    Last Sold Summary

    • $238/SF
    • 119 Days On Market

    Current Estimated Value $338,618

    Last Listing Agent Erene Katris Coldwell Banker Realty

    25291 Calvert Dr, Greensboro, MD 21639
  • 406 N Academy St, Greensboro, MD 21639
    406 N Academy St, Greensboro, MD 21639
    406 N Academy St, Greensboro, MD 21639
    /31

    $325,000 Sold Nov 14, 2025

    406 N Academy St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft
    • Built 1986

    Last Sold Summary

    • $213/SF
    • 157 Days On Market

    Current Estimated Value $326,113

    Last Listing Agent Preda Mendez-Lopez Realty One Group Performance, LLC

    406 N Academy St, Greensboro, MD 21639
  • 6999 Breeding Rd, Federalsburg, MD 21632
    6999 Breeding Rd, Federalsburg, MD 21632
    /2

    $184,000 Sold Oct 07, 2025

    6999 Breeding Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1979

    Last Sold Summary

    • $123/SF
    • 3 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    6999 Breeding Rd, Federalsburg, MD 21632
  • 306 W Central Ave, Federalsburg, MD 21632
    306 W Central Ave, Federalsburg, MD 21632
    306 W Central Ave, Federalsburg, MD 21632
    /19

    $236,000 Sold Apr 14, 2025

    306 W Central Ave, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,712 Sq Ft
    • Built 1932

    Last Sold Summary

    • $138/SF
    • 3 Days On Market

    Current Estimated Value $223,809

    Last Listing Agent Heather Brummell Keller Williams Realty

    306 W Central Ave, Federalsburg, MD 21632
  • 105 Elmor Ct, Greensboro, MD 21639
    105 Elmor Ct, Greensboro, MD 21639
    105 Elmor Ct, Greensboro, MD 21639
    /23

    $280,000 Sold Jun 28, 2025

    105 Elmor Ct, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,192 Sq Ft
    • Built 2013

    Last Sold Summary

    • $235/SF
    • 35 Days On Market

    Current Estimated Value $289,362

    Last Listing Agent BJ Kilby Eastern Shore Real Estate, LLC

    105 Elmor Ct, Greensboro, MD 21639
  • 223 Old Denton Rd, Federalsburg, MD 21632
    223 Old Denton Rd, Federalsburg, MD 21632
    223 Old Denton Rd, Federalsburg, MD 21632
    /17

    $60,000 Sold May 30, 2025

    223 Old Denton Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,488 Sq Ft
    • Built 1900

    Last Sold Summary

    • $40/SF
    • 53 Days On Market

    Last Listing Agent Benjamin Smith Real Broker, LLC

    223 Old Denton Rd, Federalsburg, MD 21632
  • 1626 Blue Heron Dr, Denton, MD 21629
    1626 Blue Heron Dr, Denton, MD 21629
    1626 Blue Heron Dr, Denton, MD 21629
    /39

    $285,000 Sold Dec 18, 2025

    1626 Blue Heron Dr, Denton, MD 21629

    • 4 Beds
    • 3.5 Baths
    • 2,244 Sq Ft
    • Built 2006

    Last Sold Summary

    • $127/SF
    • 10 Days On Market

    Current Estimated Value $289,904

    Last Listing Agent Michelle DiDonato Island Realty, LLC

    1626 Blue Heron Dr, Denton, MD 21629
  • 113 Lednum Ave, Preston, MD 21655
    113 Lednum Ave, Preston, MD 21655
    113 Lednum Ave, Preston, MD 21655
    /43

    $324,900 Sold Oct 31, 2025

    113 Lednum Ave, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,240 Sq Ft
    • Built 2001

    Last Sold Summary

    • $262/SF
    • 14 Days On Market

    Current Estimated Value $314,462

    Last Listing Agent Chris Rosendale CR Realty

    113 Lednum Ave, Preston, MD 21655
  • 1233 Painted Fern Rd, Denton, MD 21629
    1233 Painted Fern Rd, Denton, MD 21629
    1233 Painted Fern Rd, Denton, MD 21629
    /4

    $435,000 Sold Feb 25, 2026

    1233 Painted Fern Rd, Denton, MD 21629

    • 5 Beds
    • 3.5 Baths
    • 4,222 Sq Ft
    • Built 2006

    Last Sold Summary

    • $103/SF
    • 10 Days On Market

    Current Estimated Value $460,020

    Last Listing Agent Lesley Jackson Sunshine Realty LLC

    1233 Painted Fern Rd, Denton, MD 21629
  • 536 Gay St, Denton, MD 21629
    536 Gay St, Denton, MD 21629
    536 Gay St, Denton, MD 21629
    /3

    $80,000 Sold Mar 13, 2026

    536 Gay St, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,032 Sq Ft
    • Built 1910

    Last Sold Summary

    • $78/SF
    • 1 Day On Market

    Current Estimated Value $113,721

    Last Listing Agent Diane Wenk Wright Real Estate

    536 Gay St, Denton, MD 21629

Showing Results 241 - 280, Page 7 of 10

Maryland Caroline County

Recently Sold Real Estate & Homes in Caroline County, MD

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