409

Recently Sold Caroline County MD Homes

Section Image Section Image
  • /67

    $410,000

    Sold Jul 31, 2026

    109 Briarwood Cir, Denton, MD 21629

    • 4 Beds
    • 3.5 Baths
    • 3,372 Sq Ft
    • Built 2007

    Last Sold Summary

    • 4% Below List Price
    • $122/SF
    • 32 Days On Market

    Current Estimated Value $423,597

    Last Listing Agent Anissa Hastings Keller Williams Flagship

    109 Briarwood Cir, Denton, MD 21629
  • /32

    $225,000

    Sold Oct 10, 2025

    11198 Maple Ave, Hillsboro, MD 21641

    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft
    • Built 1900

    Last Sold Summary

    • $133/SF
    • 6 Days On Market

    Current Estimated Value $228,779

    Last Listing Agent Keith Hensley Meredith Fine Properties

    11198 Maple Ave, Hillsboro, MD 21641
  • /39

    $370,000

    Sold Aug 08, 2025

    22776 Squire Ln, Queen Anne, MD 21657

    • 4 Beds
    • 2.5 Baths
    • 2,088 Sq Ft
    • Built 1997

    Last Sold Summary

    • $177/SF
    • 51 Days On Market

    Current Estimated Value $401,449

    Last Listing Agent Keith Sharp Northrop Realty

    22776 Squire Ln, Queen Anne, MD 21657
  • /28

    $360,000

    Sold Jul 10, 2026

    24383 Robins Creek Rd, Preston, MD 21655

    • 4 Beds
    • 2 Baths
    • 1,568 Sq Ft
    • Built 1979

    Last Sold Summary

    • 4% Below List Price
    • $230/SF
    • 145 Days On Market

    Current Estimated Value $364,108

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

    24383 Robins Creek Rd, Preston, MD 21655
  • /12

    $1,100,000

    Sold Jun 04, 2026

    0 Liberty Rd, Federalsburg, MD 21632

    • Land
    • 92.9 Acres
    • $11,841 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 44 Days On Market

    Last Listing Agent Benjamin Alder The Land Group

    0 Liberty Rd, Federalsburg, MD 21632
  • /37

    $262,000

    Sold Jul 24, 2026

    2697 Choptank Main St, Preston, MD 21655

    • 2 Beds
    • 2 Baths
    • 1,104 Sq Ft
    • Built 1855

    Last Sold Summary

    • $237/SF
    • 295 Days On Market

    Current Estimated Value $260,536

    Last Listing Agent Darlene Wheatley Benson & Mangold, LLC

    2697 Choptank Main St, Preston, MD 21655
  • /27

    $199,990

    Sold Sep 29, 2025

    155 Riverwalk Terrace, Federalsburg, MD 21632

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

    Last Sold Summary

    • $147/SF
    • 27 Days On Market

    Current Estimated Value $205,281

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

    155 Riverwalk Terrace, Federalsburg, MD 21632
  • /2

    $277,000

    Sold Jan 15, 2026

    8259 Haven St, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,392 Sq Ft
    • Built 1983

    Last Sold Summary

    • $199/SF
    • 13 Days On Market

    Current Estimated Value $312,897

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    8259 Haven St, Denton, MD 21629
  • /54

    $585,000

    Sold Oct 10, 2025

    22109 Tanyard Rd, Preston, MD 21655

    • 4 Beds
    • 3 Baths
    • 2,640 Sq Ft
    • Built 1995

    Last Sold Summary

    • $222/SF
    • 8 Days On Market

    Current Estimated Value $598,456

    Last Listing Agent Henry Gibbons-Neff Meredith Fine Properties

    22109 Tanyard Rd, Preston, MD 21655
  • /42

    $510,000

    Sold Jul 16, 2026

    3720 Payne Rd, Preston, MD 21655

    • 4 Beds
    • 2.5 Baths
    • 2,304 Sq Ft
    • Built 1977

    Last Sold Summary

    • 7% Below List Price
    • $221/SF
    • 41 Days On Market

    Current Estimated Value $531,729

    Last Listing Agent Heather Brummell Keller Williams Realty

    3720 Payne Rd, Preston, MD 21655
  • /2

    $299,990

    Sold Jul 28, 2026

    111 Hobbs St, Greensboro, MD 21639

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

    Move in Ready Sold Summary

    • 2% Below List Price
    • $205/SF
    • 17 Days On Market

    D.R. Horton Kinnamon Meadows

    111 Hobbs St, Greensboro, MD 21639
  • /19

    $50,000

    Sold May 20, 2026

    2 N Main St, Greensboro, MD 21639

    • Land
    • 16,117 Sq Ft
    • $135,135 per Acre

    Last Sold Summary

    • 100 Days On Market

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    2 N Main St, Greensboro, MD 21639
  • /21

    $420,000

    Sold Sep 16, 2025

    24711 Pealiquor Rd, Denton, MD 21629

    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft
    • Built 1996

    Last Sold Summary

    • $206/SF
    • 5 Days On Market

    Current Estimated Value $422,240

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    24711 Pealiquor Rd, Denton, MD 21629
  • /9

    $130,000

    Sold Jul 31, 2026

    106 S 6th St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 2,776 Sq Ft
    • Built 1908

    Last Sold Summary

    • $47/SF
    • 182 Days On Market

    Current Estimated Value $167,619

    Last Listing Agent Amy Betts Coldwell Banker Realty

    106 S 6th St, Denton, MD 21629
  • /2

    $2,500,000

    Sold Jun 19, 2026

    28219 Bridgeville Rd, Federalsburg, MD 21632

    • 4 Beds
    • 4.5 Baths
    • 6,520 Sq Ft
    • Built 2007

    Last Sold Summary

    • 9% Below List Price
    • $383/SF
    • 37 Days On Market

    Current Estimated Value $2,591,787

    Last Listing Agent Jim Corson Benson & Mangold, LLC

    28219 Bridgeville Rd, Federalsburg, MD 21632
  • /2

    $325,000

    Sold Apr 17, 2026

    1203 Tuckahoe Ct, Denton, MD 21629

    • 4 Beds
    • 2 Baths
    • 1,326 Sq Ft
    • Built 1991

    Last Sold Summary

    • $245/SF
    • 39 Days On Market

    Current Estimated Value $317,484

    Last Listing Agent Alicia Gannon Dulin Benson & Mangold, LLC

    1203 Tuckahoe Ct, Denton, MD 21629
  • /27

    $219,990

    Sold Sep 05, 2025

    149 Riverwalk Terrace, Federalsburg, MD 21632

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

    Last Sold Summary

    • $161/SF
    • 4 Days On Market

    Current Estimated Value $218,928

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

    149 Riverwalk Terrace, Federalsburg, MD 21632
  • /24

    $260,000

    Sold Jul 14, 2026

    26351 Anthony Mill Rd, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 1,092 Sq Ft
    • Built 1977

    Last Sold Summary

    • 2% Below List Price
    • $238/SF
    • 1 Day On Market

    Current Estimated Value $262,873

    Last Listing Agent Linda Moore Long & Foster Real Estate, Inc.

    26351 Anthony Mill Rd, Denton, MD 21629
  • /14

    $220,000

    Sold Jun 11, 2026

    1304 Blue Heron Dr, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,560 Sq Ft
    • Built 2004

    Last Sold Summary

    • $141/SF
    • 18 Days On Market

    Current Estimated Value $218,492

    Last Listing Agent Heather Brummell Keller Williams Realty

    1304 Blue Heron Dr, Denton, MD 21629
  • /21

    $270,000

    Sold Nov 14, 2025

    515 Franklin St, Denton, MD 21629

    • 3 Beds
    • 1.5 Baths
    • 1,409 Sq Ft
    • Built 1890

    Last Sold Summary

    • $192/SF
    • 6 Days On Market

    Current Estimated Value $268,923

    Last Listing Agent Janet Powers Berkshire Hathaway Homeservice Homesale Realty

    515 Franklin St, Denton, MD 21629
  • /39

    $399,000

    Sold Aug 19, 2025

    8912 Osterman Ct, Denton, MD 21629

    • 4 Beds
    • 3.5 Baths
    • 2,780 Sq Ft
    • Built 1993

    Last Sold Summary

    • $144/SF
    • 19 Days On Market

    Current Estimated Value $416,405

    Last Listing Agent Nanci Gardner Meredith Fine Properties

    8912 Osterman Ct, Denton, MD 21629
  • /23

    $137,400

    Sold Dec 29, 2025

    109 Buena Vista Ave, Federalsburg, MD 21632

    • 3 Beds
    • 1.5 Baths
    • 1,393 Sq Ft
    • Built 1932

    Last Sold Summary

    • $99/SF
    • 14 Days On Market

    Current Estimated Value $150,942

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

    109 Buena Vista Ave, Federalsburg, MD 21632
  • /40

    $360,000

    Sold Dec 23, 2025

    13070 Ridgely Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1982

    Last Sold Summary

    • $268/SF
    • 47 Days On Market

    Current Estimated Value $366,164

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    13070 Ridgely Rd, Greensboro, MD 21639
  • /53

    $175,000

    Sold May 21, 2026

    22060 Main St, Hillsboro, MD 21641

    • 3 Beds
    • 1.5 Baths
    • 2,817 Sq Ft
    • Built 1900

    Last Sold Summary

    • 22% Below List Price
    • $62/SF
    • 138 Days On Market

    Current Estimated Value $268,194

    Last Listing Agent Keith Brooks Thurston Wyatt Real Estate, LLC

    22060 Main St, Hillsboro, MD 21641
  • /36

    $295,000

    Sold Jul 20, 2026

    6101 Bethlehem Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,392 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Above List Price
    • $212/SF
    • 25 Days On Market

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    6101 Bethlehem Rd, Preston, MD 21655
  • /128

    $1,150,000

    Sold Mar 27, 2026

    24800 Pealiquor Rd, Denton, MD 21629

    • 4 Beds
    • 3.5 Baths
    • 4,496 Sq Ft
    • Built 1945

    Last Sold Summary

    • $256/SF
    • 87 Days On Market

    Current Estimated Value $1,150,653

    Last Listing Agent Christina Ginn Fathom Realty LLC

    24800 Pealiquor Rd, Denton, MD 21629
  • /12

    $295,000

    Sold Jul 23, 2026

    5 7th St, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft
    • Built 1992

    Last Sold Summary

    • 2% Below List Price
    • $288/SF
    • 70 Days On Market

    Current Estimated Value $295,163

    Last Listing Agent Marcia Rostien Long & Foster Real Estate, Inc.

    5 7th St, Ridgely, MD 21660
  • /7

    $137,000

    Sold Apr 28, 2026

    305 Maple Ave, Ridgely, MD 21660

    • 2 Beds
    • 1 Bath
    • 504 Sq Ft
    • Built 1945

    Last Sold Summary

    • 6% Below List Price
    • $272/SF
    • 67 Days On Market

    Current Estimated Value $136,937

    Last Listing Agent Andrew Beaven Wright Real Estate

    305 Maple Ave, Ridgely, MD 21660
  • /51

    $619,000

    Sold Mar 24, 2026

    24324 Asbury Dr, Denton, MD 21629

    • 4 Beds
    • 4 Baths
    • 3,484 Sq Ft
    • Built 2002

    Last Sold Summary

    • $178/SF
    • 154 Days On Market

    Current Estimated Value $618,552

    Last Listing Agent Bonnie Johnson Keller Williams Realty

    24324 Asbury Dr, Denton, MD 21629
  • /20

    $271,500

    Sold Dec 15, 2025

    22991 Westview Dr, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,032 Sq Ft
    • Built 1975

    Last Sold Summary

    • $263/SF
    • 29 Days On Market

    Current Estimated Value $268,472

    Last Listing Agent Jennifer Norfolk Coldwell Banker Waterman Realty

    22991 Westview Dr, Preston, MD 21655
  • /55

    $370,000

    Sold Dec 30, 2025

    26722 Sandtown Rd, Goldsboro, MD 21636

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2006

    Last Sold Summary

    • $300/SF
    • 68 Days On Market

    Current Estimated Value $373,706

    Last Listing Agent Megan Rosendale Rosendale Realty

    26722 Sandtown Rd, Goldsboro, MD 21636
  • /36

    $375,000

    Sold Jul 08, 2026

    6326 Statum Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2002

    Last Sold Summary

    • $279/SF
    • 2 Days On Market

    Current Estimated Value $370,196

    Last Listing Agent Sean O'Connor Coldwell Banker Realty

    6326 Statum Rd, Preston, MD 21655
  • /2

    $50,000

    Sold Dec 10, 2025

    402 LOT 2 W Sunset Ave, Greensboro, MD 21639

    • Land
    • 10,018 Sq Ft
    • $217,391 per Acre

    Last Sold Summary

    • 195 Days On Market

    Last Listing Agent Lisa Knotts Coldwell Banker Realty

    402 LOT 2 W Sunset Ave, Greensboro, MD 21639
  • /3

    $292,990

    Sold Jan 28, 2026

    125 Parkland Rd, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 2025

    Last Sold Summary

    • $201/SF
    • 39 Days On Market

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

    125 Parkland Rd, Greensboro, MD 21639
  • /4

    $88,000

    Sold Dec 15, 2025

    Lot 1 Clark Canning House Rd, Federalsburg, MD 21632

    • Land
    • 2 Acres
    • $44,000 per Acre

    Last Sold Summary

    • 253 Days On Market

    Last Listing Agent Mickey Hayward Sunset Properties

    Lot 1 Clark Canning House Rd, Federalsburg, MD 21632
  • /38

    $220,000

    Sold Feb 25, 2026

    1403 Blue Heron Dr, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft
    • Built 2004

    Last Sold Summary

    • $131/SF
    • 83 Days On Market

    Current Estimated Value $227,543

    Last Listing Agent Dale Hunter Bayside Realty

    1403 Blue Heron Dr, Denton, MD 21629
  • /33

    $250,000

    Sold Jul 13, 2026

    4 N Maple Ave, Ridgely, MD 21660

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1977

    Last Sold Summary

    • 6% Below List Price
    • $289/SF
    • 46 Days On Market

    Current Estimated Value $242,209

    Last Listing Agent Crystal Smith RE/MAX Executive

    4 N Maple Ave, Ridgely, MD 21660
  • /8

    $35,000

    Sold Oct 31, 2025

    3680 Houston Branch Rd, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 528 Sq Ft
    • Built 1948

    Last Sold Summary

    • $66/SF
    • 19 Days On Market

    Current Estimated Value $107,764

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

    3680 Houston Branch Rd, Federalsburg, MD 21632
  • /60

    $435,000

    Sold Jun 05, 2026

    20915 Dover Bridge Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,904 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Below List Price
    • $228/SF
    • 5 Days On Market

    Current Estimated Value $431,838

    Last Listing Agent Alex Martinez The Agency DC

    20915 Dover Bridge Rd, Preston, MD 21655
  • /28

    $275,000

    Sold Oct 22, 2025

    113 Chambers St, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1995

    Last Sold Summary

    • $229/SF
    • 22 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    113 Chambers St, Preston, MD 21655

Showing Results 321 - 360, Page 9 of 11

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