406

Recently Sold Caroline County MD Homes

Section Image Section Image
  • /25

    $82,000

    Sold Jul 21, 2026

    28035 Possum Hill Rd, Federalsburg, MD 21632

    • 4 Beds
    • 30 Baths
    • 1,428 Sq Ft
    • Built 1990

    Last Sold Summary

    • $57/SF
    • 888 Days On Market

    Current Estimated Value $161,440

    Last Listing Agent Sam Benkirane Proplocate Realty, LLC

    28035 Possum Hill Rd, 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 $53,444

    Last Listing Agent Heather Brummell Keller Williams Realty

    307 Buena Vista Ave, Federalsburg, MD 21632
  • /42

    $465,000

    Sold Mar 30, 2026

    24749 Woods Dr, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,550 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Below List Price
    • $182/SF
    • 80 Days On Market

    Current Estimated Value $463,990

    Last Listing Agent Peter Stark Benson & Mangold, LLC

    24749 Woods Dr, Denton, MD 21629
  • /30

    $289,000

    Sold Jun 30, 2026

    14185 Drapers Mill Rd, Greensboro, MD 21639

    • 4 Beds
    • 1 Bath
    • 1,352 Sq Ft
    • Built 1910

    Last Sold Summary

    • 3% Below List Price
    • $214/SF
    • 56 Days On Market

    Current Estimated Value $284,002

    Last Listing Agent John Lyons Crown Homes Real Estate

    14185 Drapers Mill Rd, Greensboro, MD 21639
  • /37

    $205,000

    Sold Apr 09, 2026

    318 Carter Ave, Denton, MD 21629

    • 2 Beds
    • 2 Baths
    • 606 Sq Ft
    • Built 1950

    Last Sold Summary

    • $338/SF
    • 96 Days On Market

    Current Estimated Value $202,029

    Last Listing Agent Georgi Chauvin Benson & Mangold, LLC

    318 Carter Ave, Denton, MD 21629
  • /60

    $400,000

    Sold Jan 06, 2026

    106 Briarwood Cir, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,551 Sq Ft
    • Built 2021

    Last Sold Summary

    • $157/SF
    • 4 Days On Market

    Current Estimated Value $406,147

    Last Listing Agent Stephanie Smith Douglas Realty, LLC

    106 Briarwood Cir, Denton, MD 21629
  • /20

    $189,000

    Sold Dec 02, 2025

    301 Central Ave, Ridgely, MD 21660

    • 4 Beds
    • 1 Bath
    • 1,706 Sq Ft
    • Built 1860

    Last Sold Summary

    • $111/SF
    • 7 Days On Market

    Current Estimated Value $193,879

    Last Listing Agent Jim Corson Benson & Mangold, LLC

    301 Central Ave, Ridgely, MD 21660
  • /22

    $364,000

    Sold May 20, 2026

    3 Sunrise Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,292 Sq Ft
    • Built 2026

    Last Sold Summary

    • $282/SF
    • 134 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    3 Sunrise Ave, Ridgely, MD 21660
  • /21

    $249,500

    Sold Nov 10, 2025

    529 N 6th St, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,019 Sq Ft
    • Built 1930

    Last Sold Summary

    • $245/SF
    • 62 Days On Market

    Current Estimated Value $242,112

    Last Listing Agent Cody Weese Weese Properties, LLC

    529 N 6th St, Denton, MD 21629
  • /2

    $399,000

    Sold Jul 14, 2026

    24254 Mallow Dr, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • Built 1999

    Last Sold Summary

    • $242/SF
    • 7 Days On Market

    Current Estimated Value $397,642

    Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

    24254 Mallow Dr, Preston, MD 21655
  • /70

    $325,000

    Sold Mar 12, 2026

    25361 Calvert Dr, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft
    • Built 1989

    Last Sold Summary

    • $224/SF
    • 50 Days On Market

    Current Estimated Value $333,875

    Last Listing Agent Chris Rosendale CR Realty

    25361 Calvert Dr, Greensboro, MD 21639
  • /2

    $274,990

    Sold Aug 06, 2026

    125 Hobbs St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 4% Below List Price
    • $233/SF
    • 21 Days On Market

    D.R. Horton Kinnamon Meadows

    125 Hobbs St, Greensboro, MD 21639
  • /23

    $365,000

    Sold Dec 22, 2025

    8 Sunrise Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,292 Sq Ft
    • Built 2025

    Last Sold Summary

    • $283/SF
    • 6 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    8 Sunrise Ave, Ridgely, MD 21660
  • /26

    $310,000

    Sold Jun 12, 2026

    1 Oakview Ct, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,104 Sq Ft
    • Built 1998

    Last Sold Summary

    • 2% Below List Price
    • $281/SF
    • 129 Days On Market

    Current Estimated Value $306,614

    Last Listing Agent Peter Stark Benson & Mangold, LLC

    1 Oakview Ct, Ridgely, MD 21660
  • /2

    $700,000

    Sold Jun 16, 2026

    11745 Eveland Rd, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 924 Sq Ft
    • Built 1992

    Last Sold Summary

    • $758/SF

    Last Listing Agent Michael Doyle Taylor Properties

    11745 Eveland Rd, Ridgely, MD 21660
  • /20

    $55,000

    Sold Apr 13, 2026

    21182 Marsh Creek Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 2006

    Last Sold Summary

    • 8% Below List Price
    • $57/SF
    • 26 Days On Market

    Last Listing Agent Shane Slacum LPT Realty, LLC

    21182 Marsh Creek Rd, Preston, MD 21655
  • /28

    $399,000

    Sold Sep 18, 2026

    1 Sunrise Ave, Ridgely, MD 21660

    • 4 Beds
    • 2.5 Baths
    • 1,768 Sq Ft
    • Built 2026

    Last Sold Summary

    • $226/SF
    • 312 Days On Market

    Current Estimated Value $410,061

    Last Listing Agent Crystal Smith RE/MAX Executive

    1 Sunrise Ave, Ridgely, MD 21660
  • /25

    $240,000

    Sold Nov 12, 2025

    317 W Central Ave, Federalsburg, MD 21632

    • 4 Beds
    • 1.5 Baths
    • 1,670 Sq Ft
    • Built 1931

    Last Sold Summary

    • $144/SF
    • 56 Days On Market

    Current Estimated Value $238,100

    Last Listing Agent Kelly Sharpless Kelstar Properties

    317 W Central Ave, Federalsburg, MD 21632
  • /3

    $130,000

    Sold May 26, 2026

    1005 Market St, Denton, MD 21629

    • Land
    • 30,056 Sq Ft
    • $188,406 per Acre

    Last Sold Summary

    • 159 Days On Market

    Current Estimated Value $130,000

    Last Listing Agent Barbara Beaudet Brenton Realty Group

    1005 Market St, Denton, MD 21629
  • /37

    $230,000

    Sold Jun 18, 2026

    121 E Central Ave, Federalsburg, MD 21632

    • 4 Beds
    • 2 Baths
    • 2,320 Sq Ft
    • Built 1910

    Last Sold Summary

    • 8% Below List Price
    • $99/SF
    • 26 Days On Market

    Current Estimated Value $241,909

    Last Listing Agent LEE MARLAND Keller Williams Realty

    121 E Central Ave, Federalsburg, MD 21632
  • /28

    $150,000

    Sold Jul 24, 2026

    Parcels #82 & #96 Drapers Mill Rd, Goldsboro, MD 21636

    • Land
    • 7.99 Acres
    • $18,773 per Acre

    Last Sold Summary

    • 21% Below List Price
    • 71 Days On Market

    Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

    Parcels #82 & #96 Drapers Mill Rd, Goldsboro, MD 21636
  • /41

    $399,900

    Sold Jul 23, 2026

    103 Elmor Ct, Greensboro, MD 21639

    • 5 Beds
    • 3 Baths
    • 2,232 Sq Ft
    • Built 2006

    Last Sold Summary

    • $179/SF
    • 11 Days On Market

    Current Estimated Value $397,892

    Last Listing Agent BJ Kilby Eastern Shore Real Estate, LLC

    103 Elmor Ct, Greensboro, MD 21639
  • /2

    $292,990

    Sold Jan 15, 2026

    131 Hobbs St, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $201/SF
    • 76 Days On Market

    D.R. Horton Kinnamon Meadows

    131 Hobbs St, Greensboro, MD 21639
  • /15

    $409,000

    Sold Jul 10, 2026

    0 Quail Ct Unit MDCM2006742, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths

    Last Sold Summary

    • 18 Days On Market

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

    0 Quail Ct Unit MDCM2006742, Greensboro, MD 21639
  • /50

    $465,000

    Sold Jul 02, 2026

    11421 Maplewood Dr, Ridgely, MD 21660

    • 3 Beds
    • 2.5 Baths
    • 1,840 Sq Ft
    • Built 2020

    Last Sold Summary

    • $253/SF
    • 7 Days On Market

    Current Estimated Value $457,420

    Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

    11421 Maplewood Dr, Ridgely, MD 21660
  • /2

    $200,000

    Sold Apr 14, 2026

    302 W Railroad St, Ridgely, MD 21660

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft
    • Built 1927

    Last Sold Summary

    • 2% Below List Price
    • $278/SF
    • 19 Days On Market

    Current Estimated Value $194,248

    Last Listing Agent Michael Shipley Benson & Mangold, LLC.

    302 W Railroad St, Ridgely, MD 21660
  • /20

    $345,000

    Sold Jul 15, 2026

    114 Wothers Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft
    • Built 1972

    Last Sold Summary

    • $228/SF
    • 37 Days On Market

    Current Estimated Value $341,568

    Last Listing Agent Anthony MacDonald Iron Valley Real Estate Ocean City

    114 Wothers Rd, Greensboro, MD 21639
  • /26

    $165,000

    Sold Feb 27, 2026

    9571 Legion Rd, Denton, MD 21629

    • Land
    • 1.19 Acres
    • $138,655 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 11 Days On Market

    Current Estimated Value $167,975

    Last Listing Agent Sharon Fisher Coldwell Banker Realty

    9571 Legion Rd, Denton, MD 21629
  • /9

    $185,000

    Sold Feb 05, 2026

    306 Bernard Ave, Greensboro, MD 21639

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 2002

    Last Sold Summary

    • $241/SF
    • 145 Days On Market

    Current Estimated Value $206,550

    Last Listing Agent Amanda Morgan Brenton Realty Group

    306 Bernard Ave, Greensboro, MD 21639
  • /54

    $435,000

    Sold Jul 16, 2026

    23283 Magnolia Hills Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 2,044 Sq Ft
    • Built 2016

    Last Sold Summary

    • 2% Below List Price
    • $213/SF
    • 44 Days On Market

    Current Estimated Value $435,235

    Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

    23283 Magnolia Hills Rd, Denton, MD 21629
  • /41

    $245,000

    Sold Jul 06, 2026

    3675 Seaman Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,787 Sq Ft
    • Built 1973

    Last Sold Summary

    • 5% Below List Price
    • $137/SF
    • 15 Days On Market

    Current Estimated Value $261,436

    Last Listing Agent Andrew Beaven Wright Real Estate

    3675 Seaman Rd, Preston, MD 21655
  • /57

    $474,000

    Sold Jul 16, 2026

    7837 Shore Dr, Preston, MD 21655

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft
    • Built 2005

    Last Sold Summary

    • 4% Below List Price
    • $247/SF
    • 75 Days On Market

    Current Estimated Value $474,936

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    7837 Shore Dr, Preston, MD 21655
  • /43

    $375,000

    Sold Mar 12, 2026

    21405 Tanyard Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 3,212 Sq Ft
    • Built 1974

    Last Sold Summary

    • $117/SF
    • 102 Days On Market

    Current Estimated Value $381,836

    Last Listing Agent Justin Pokrywka Taylor Properties

    21405 Tanyard Rd, Preston, MD 21655
  • /71

    $1,099,999

    Sold Jun 09, 2026

    7904 Clark Rd, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 3,242 Sq Ft
    • Built 1998

    Last Sold Summary

    • $339/SF
    • 29 Days On Market

    Current Estimated Value $1,074,538

    Last Listing Agent Jesse Highling The Land Group

    7904 Clark 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 $481,868

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    23678 Willow Pond Rd, Denton, MD 21629
  • /40

    $260,000

    Sold Sep 21, 2026

    103 Williamson St, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft
    • Built 1900

    Last Sold Summary

    • 9% Below List Price
    • $155/SF
    • 47 Days On Market

    Current Estimated Value $281,497

    Last Listing Agent Dawn Hubbard Mabry Real Estate LLC

    103 Williamson St, Preston, MD 21655
  • /10

    $140,000

    Sold Jul 10, 2026

    107 N School St Unit 3B, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 968 Sq Ft
    • Built 1922

    Last Sold Summary

    • 22% Below List Price
    • $145/SF
    • 60 Days On Market

    Current Estimated Value $158,324

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    107 N School St Unit 3B, Greensboro, MD 21639
  • /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 $145,566

    Last Listing Agent Karla Wieland-Cherry Meredith Fine Properties

    307 Academy Ave, Denton, MD 21629
  • /24

    $399,900

    Sold Sep 11, 2026

    11139 Central Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1979

    Last Sold Summary

    • $357/SF
    • 9 Days On Market

    Current Estimated Value $344,219

    Last Listing Agent BJ Kilby Eastern Shore Real Estate, LLC

    11139 Central Ave, Ridgely, MD 21660
  • /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 $199,739

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

    213 W Central Ave, Federalsburg, MD 21632

Showing Results 201 - 240, Page 6 of 11

How to Buy a Home How to Finance a Home How to Sell a Home