15,709

Caroline County, MD Homes

Section Image Section Image
  • /69

    $740,000

    • 5 Beds
    • 4 Baths
    • 5,286 Sq Ft

    24764 Pealiquor Rd, Denton, MD 21629

    Welcome to Timeless Elegance Meets Modern Comfort. Step inside this stunning Cape Cod residence and immediately feel at home. A gracious foyer framed by classic columns invites you into a luminous interior that effortlessly blends traditional charm with modern open‐concept living. To your right, a versatile flex room offers the perfect space for a home office, formal dining, or private study.

    Dustin Parker The Parker Group

    24764 Pealiquor Rd, Denton, MD 21629
  • /29

    $380,000 Sold Nov 14, 2025

    24887 Holsinger Ln, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 2015

    Last Sold Summary

    • $264/SF
    • 120 Days On Market

    Current Estimated Value $385,734

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    24887 Holsinger Ln, Ridgely, MD 21660
    • /48

      Est $279,368 Not Listed For Sale

      219 Briarwood Cir, Denton, MD 21629

      • 4 Beds
      • 4 Baths
      • 2,088 Sq Ft
      • Built 2006
      219 Briarwood Cir, Denton, MD 21629

      Last Sold Summary

      • 2% Below List Price
      • $136/SF
      • 4 Days On Market
      • Last Sold Price $285,000
      • Nov 12, 2024

      Last Listing Agent Kimberly Dixson Coldwell Banker (NRT-Southeast-MidAtlantic)

  • /10

    $184,900

    • 3 Beds
    • 1 Bath
    • 716 Sq Ft

    406 Lincoln St, Denton, MD 21629

    This adorable home is ready and waiting for you to move in and make it your own. The home was renovated just 2 years ago. Updated items include windows, HVAC, cabinets, flooring, carpet, plumbing, electrical, roof & new insulation in the crawl space. Enjoy being close to local restaurants, shops, parks, schools, boat ramps, and MD/DE beaches. This property was most recently used as an

    Lisa Andrews Chesapeake Real Estate Associates, LLC

    406 Lincoln St, Denton, MD 21629
  • /11

    $245,000 Sold Sep 09, 2025

    210 Denton Rd, Federalsburg, MD 21632

    • 4 Beds
    • 3 Baths
    • 1,190 Sq Ft
    • Built 1935

    Last Sold Summary

    • $206/SF
    • 127 Days On Market

    Current Estimated Value $193,480

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    210 Denton Rd, Federalsburg, MD 21632
    • /9

      Est $107,855 Not Listed For Sale

      25782 Goldsboro Rd, Goldsboro, MD 21636

      • 2 Beds
      • 1 Bath
      • 1,386 Sq Ft
      • Built 1910
      25782 Goldsboro Rd, Goldsboro, MD 21636

      Last Sold Summary

      • 3% Above List Price
      • $76/SF
      • 46 Days On Market
      • Last Sold Price $105,000
      • Apr 22, 2025

      Last Listing Agent Pamela Geib Long & Foster

  • /26

    $340,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft

    25550 Linhard Ln, Greensboro, MD 21639

    Welcome to your own charming private retreat! This beautifully remodeled property truly has it all. Step inside this open‐concept rancher filled with natural light, where the living, dining, and kitchen spaces flow seamlessly together. The kitchen is a showstopper—brand‐new cabinets, granite countertops, stainless steel appliances, and a large island perfect for the chef of the house or for

    Amanda Morgan Brenton Realty Group

    25550 Linhard Ln, Greensboro, MD 21639
  • /34

    $332,000 Sold Sep 05, 2025

    22329 Tanyard Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,058 Sq Ft
    • Built 1972

    Last Sold Summary

    • $314/SF
    • 29 Days On Market

    Current Estimated Value $330,951

    Last Listing Agent Laura Anderson Coldwell Banker Realty

    22329 Tanyard Rd, Preston, MD 21655
    • /11

      Est $282,188 Not Listed For Sale

      408 Maple Ave, Ridgely, MD 21660

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1978
      408 Maple Ave, Ridgely, MD 21660

      Last Sold Summary

      • 3% Above List Price
      • $260/SF
      • 62 Days On Market
      • Last Sold Price $275,000
      • Jun 05, 2024

      Last Listing Agent Bonnie Duley Long & Foster

  • /30

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,932 Sq Ft

    7844 Shore Dr, Preston, MD 21655

    Unplug from the hustle and bustle in this well maintained one floor home on the banks of the Choptank River. The views of the native wetlands and its wildlife are unique and beautiful in a way only mother nature can create. The spacious and quiet yard receives abundant sunlight and could provide for amazing gardening opportunities. An old dock remains in need of extensive repair but the next

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    7844 Shore Dr, Preston, MD 21655
  • /33

    $415,000 Sold Sep 30, 2025

    12 Sunrise Ave, Ridgely, MD 21660

    • 4 Beds
    • 2 Baths
    • 1,628 Sq Ft
    • Built 2025

    Last Sold Summary

    • $255/SF
    • 187 Days On Market

    Last Listing Agent Crystal Smith RE/MAX Executive

    12 Sunrise Ave, Ridgely, MD 21660
    • /20

      Est $244,298 Not Listed For Sale

      411 N 6th St, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,364 Sq Ft
      • Built 1900
      411 N 6th St, Denton, MD 21629

      Last Sold Summary

      • 6% Below List Price
      • $191/SF
      • 115 Days On Market
      • Last Sold Price $260,000
      • Jul 15, 2024

      Last Listing Agent Kat Thompson Benson & Mangold, LLC.

  • /4

    $24,500

    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft

    204 Academy Ave, Federalsburg, MD 21632

    Investor special! This property is being sold AS-IS and is priced for land value or a full renovation. The existing structure requires extensive repairs or complete tear-down—ideal for experienced builders, contractors, or savvy investors looking for a project. Buyer to verify zoning, permits, potential use. Buyer Broker/Agent and/or Buyer must do their own due diligence to verify if the existing

    Mike Dunn Keller Williams Realty Delmarva

    204 Academy Ave, Federalsburg, MD 21632
  • /2

    $43,000 Sold May 23, 2025

    0 Harmony Rd Unit MDCM2003730, Preston, MD 21655

    • Land
    • 1.21 Acres
    • $35,537 per Acre

    Last Sold Summary

    • 497 Days On Market

    Last Listing Agent Gary Lucks Keller Williams Realty

    0 Harmony Rd Unit MDCM2003730, Preston, MD 21655
    • /13

      Est $196,639 Not Listed For Sale

      101 Vaughn Ave, Greensboro, MD 21639

      • 2 Beds
      • 1 Bath
      • 1,004 Sq Ft
      • Built 1950
      101 Vaughn Ave, Greensboro, MD 21639

      Last Sold Summary

      • 3% Above List Price
      • $189/SF
      • 7 Days On Market
      • Last Sold Price $190,000
      • Feb 19, 2025

      Last Listing Agent Kat Thompson Benson & Mangold, LLC.

  • /36

    $250,000

    • 2 Baths
    • 3,028 Sq Ft

    130 Halltown Rd, Marydel, MD 21649

    Can you turn this space into a home? It’s the kind of opportunity that doesn’t come around often here in Marydel. This former church turned community hall sits on just under an acre and offers over 3,000 square feet to work with, including a wide open event space and a surprisingly large kitchen at just over 515 square feet. The subflooring and joists in the main hall have already been replaced

    Micheal Vakas EXP Realty, LLC

    130 Halltown Rd, Marydel, MD 21649
  • /17

    $67,000 Sold Sep 19, 2025

    21182 Marsh Creek Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,116 Sq Ft
    • Built 2020

    Last Sold Summary

    • $60/SF
    • 25 Days On Market

    Last Listing Agent Toni McDowell Keller Williams Select Realtors of Annapolis

    21182 Marsh Creek Rd, Preston, MD 21655
    • /32

      Est $410,562 Not Listed For Sale

      288 Tidewater Cir, Preston, MD 21655

      • 4 Beds
      • 2.5 Baths
      • 2,842 Sq Ft
      • Built 2006
      288 Tidewater Cir, Preston, MD 21655

      Last Sold Summary

      • 3% Above List Price
      • $141/SF
      • 56 Days On Market
      • Last Sold Price $400,000
      • Dec 09, 2024

      Last Listing Agent Richard Pullin Weichert Corporate

  • /23

    $200,000

    • 3 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    1507 Blue Heron Dr, Denton, MD 21629

    3-Story Townhome Ready for Its New Owners!Home offers 3 bedrooms and 2.5 baths with a functional layout and comfortable living spaces. The spacious first floor features an open living area and convenient half bath for guests.The second floor includes two bedrooms, a full bath, and laundry area, providing everyday convenience. The third-floor primary suite offers a private retreat with a

    KL Harris Keller Williams Select Realtors of Cambridge

    1507 Blue Heron Dr, Denton, MD 21629
  • /54

    $499,500 Sold Sep 22, 2025

    11575 Maplewood Dr, Ridgely, MD 21660

    • 4 Beds
    • 3 Baths
    • 1,900 Sq Ft
    • Built 2020

    Last Sold Summary

    • $263/SF
    • 4 Days On Market

    Current Estimated Value $508,633

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    11575 Maplewood Dr, Ridgely, MD 21660
    • /61

      Est $430,429 Not Listed For Sale

      1107 Ruddy Duck Ct, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,914 Sq Ft
      • Built 2006
      1107 Ruddy Duck Ct, Denton, MD 21629

      Last Sold Summary

      • 2% Above List Price
      • $144/SF
      • 7 Days On Market
      • Last Sold Price $420,000
      • Jul 17, 2023

      Last Listing Agent Andrea Geppi Coldwell Banker Realty

  • /40

    $275,000

    • 2 Beds
    • 1 Bath
    • 1,056 Sq Ft

    12 N Maple Ave, Ridgely, MD 21660

    Welcome home to this charming 2-bedroom, 1-bath gem nestled in a quiet, established neighborhood. Perfect for first-time buyers, downsizers, or anyone looking for comfortable, low-maintenance living, this home offers both warmth and functionality. Step inside to find beautiful new wood flooring flowing through the living room, kitchen, and hallway, creating a fresh and modern feel throughout the

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    12 N Maple Ave, Ridgely, MD 21660
  • /25

    $350,000 Sold May 29, 2025

    24636 Williston Rd, Denton, MD 21629

    • 3 Beds
    • 1.5 Baths
    • 1,472 Sq Ft
    • Built 1959

    Last Sold Summary

    • $238/SF
    • 320 Days On Market

    Current Estimated Value $366,690

    Last Listing Agent Andrew Beaven Wright Real Estate

    24636 Williston Rd, Denton, MD 21629
    • /19

      Est $329,219 Not Listed For Sale

      6 Oak St, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,480 Sq Ft
      • Built 1979
      6 Oak St, Ridgely, MD 21660

      Last Sold Summary

      • 5% Above List Price
      • $213/SF
      • 2 Days On Market
      • Last Sold Price $315,000
      • May 17, 2024

      Last Listing Agent Heather Brummell Keller Williams Realty

  • /33

    $339,900

    • 4 Beds
    • 2 Baths
    • 1,440 Sq Ft

    147 Mill St, Preston, MD 21655

    Well Maintained 4 Bed 2 Full Bath Cape Cod. Large Eat-in Kitchen w/ Stainless Steel Appliances, Granite Countertops and Center Island!Nice Size Family Room. Outdoors feature a Large Shed with Heat and Air (currently used as a very nice office) , Separate Shed for storage at the back of Spacious level Lot. Patio for entertaining and more... Home is less than 1 Mile to Choptank River Landing!

    Kathleen Brenton Brenton Realty Group

    147 Mill St, Preston, MD 21655
  • /8

    $129,000 Sold Apr 01, 2026

    0 Burnt Mill Rd Unit MDCM2005292, Ridgely, MD 21660

    • Land
    • 3.51 Acres
    • $36,752 per Acre

    Last Sold Summary

    • 381 Days On Market

    Last Listing Agent Gretchen Wichlinski Compass

    0 Burnt Mill Rd Unit MDCM2005292, Ridgely, MD 21660
    • /10

      Est $151,472 Not Listed For Sale

      112 Vernon Ave, Federalsburg, MD 21632

      • 2 Beds
      • 2 Baths
      • 884 Sq Ft
      • Built 1938
      112 Vernon Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 32% Above List Price
      • $130/SF
      • 7 Days On Market
      • Last Sold Price $115,000
      • Jun 21, 2024

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • /3

    $282,990 New Construction

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

    Curtis Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms and two bathrooms. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the right, a long, main hallway allows for the two guest bedrooms and guest bathroom to be separate from the living areas of the home. Along

    D.R. Horton Builder
    103 Park Ave Unit 36203276, Greensboro, MD 21639
  • /36

    $325,000 Sold Sep 26, 2025

    6315 Harmony Rd, Preston, MD 21655

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

    Last Sold Summary

    • $161/SF
    • 28 Days On Market

    Current Estimated Value $329,921

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    6315 Harmony Rd, Preston, MD 21655
    • /32

      Est $259,432 Not Listed For Sale

      203 Greenridge Rd, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,479 Sq Ft
      • Built 1938
      203 Greenridge Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 4% Below List Price
      • $183/SF
      • 29 Days On Market
      • Last Sold Price $270,000
      • Mar 14, 2025

      Last Listing Agent Meme ELLIS Keller Williams Realty

  • /23

    $298,990 Pending

    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    123 Hobbs St, Greensboro, MD 21639

    Welcome to 123 Hobbs Street where a soon to be built new home can be yours in Kinnamon Meadows in Greensboro, MD. The Sullivan is a charming 1,219-square-foot, cottage-style ranch home featuring three bedrooms, two bathrooms, and a one-car garage. Just off the foyer, two spacious guest bedrooms and a shared full bathroom offer comfort and privacy for family or visitors. The open-concept kitchen

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

    123 Hobbs St, Greensboro, MD 21639
  • /59

    $385,000 Sold May 12, 2025

    25820 Dogwood Rd, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft
    • Built 1979

    Last Sold Summary

    • $246/SF
    • 203 Days On Market

    Current Estimated Value $412,347

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

    25820 Dogwood Rd, Greensboro, MD 21639
    • /24

      Est $217,724 Not Listed For Sale

      108 Liberty Rd, Federalsburg, MD 21632

      • 3 Beds
      • 1.5 Baths
      • 1,756 Sq Ft
      • Built 1890
      108 Liberty Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 6% Above List Price
      • $117/SF
      • 177 Days On Market
      • Last Sold Price $204,900
      • Jan 18, 2024

      Last Listing Agent Carolina Mosquera Weichert Corporate

  • /23

    $749,000 Under Contract

    21682 Dover Bridge Rd, Preston, MD 21655

    Beautiful farm outside of Preston. 2 parcels included in the sale totaling 95+/- acres improved with a 4 bay run in shed with power and an additional storage shed. Incredible hunting and there was a perc on the property however would need to be re-evaluated.

    Jim Corson Benson & Mangold, LLC

    21682 Dover Bridge Rd, Preston, MD 21655
  • /42

    $1,550,000 Sold Jun 13, 2025

    28268 Bridgeville Rd, Federalsburg, MD 21632

    • 4 Beds
    • 2 Baths
    • 1,888 Sq Ft
    • Built 1900

    Last Sold Summary

    • $821/SF
    • 11 Days On Market

    Current Estimated Value $1,465,770

    Last Listing Agent Nick Campanaro The Land Group

    28268 Bridgeville Rd, Federalsburg, MD 21632
    • /11

      Est $300,459 Not Listed For Sale

      505 S 2nd St, Denton, MD 21629

      • 3 Beds
      • 1.5 Baths
      • 2,058 Sq Ft
      • Built 1941
      505 S 2nd St, Denton, MD 21629

      Last Sold Summary

      • 8% Above List Price
      • $135/SF
      • 12 Days On Market
      • Last Sold Price $278,501
      • Sep 13, 2024

      Last Listing Agent Pamela Geib Long & Foster

  • /19

    $89,900

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    27980 Ruritan Rd, Denton, MD 21629

    CALLING ALL INVESTORS! This property in Denton is the one you have been waiting for! This one will not last! This Property is being sold As-Is condition. Buyer is responsible for all certifications. Seller never occupied. Neither the seller or listing agent make any representation as to the accuracy of any information contained herein. Buyer must conduct their own due diligence, verification,

    Simran Dheer Tesla Realty Group, LLC

    27980 Ruritan Rd, Denton, MD 21629
  • /5

    $201,000 Sold Dec 19, 2025

    6561 Bell Creek Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1915

    Last Sold Summary

    • $149/SF
    • 14 Days On Market

    Current Estimated Value $200,282

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

    6561 Bell Creek Rd, Preston, MD 21655
    • /20

      Est $217,482 Not Listed For Sale

      217 Greenridge Rd, Federalsburg, MD 21632

      • 2 Beds
      • 1.5 Baths
      • 1,276 Sq Ft
      • Built 1950
      217 Greenridge Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 2% Below List Price
      • $174/SF
      • 2 Days On Market
      • Last Sold Price $222,000
      • May 29, 2024

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /2

    $270,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    325 Carter Ave, Denton, MD 21629

    Excellent cozy home just waiting for you in the town of Denton with the small town atmosphere and a lot of amenities. Affordably priced, close to shopping, easy commute to the Western Shore and close enough to Delaware and Maryland beaches. Come see today because this home will not last long.

    George Thompson Long & Foster Real Estate, Inc.

    325 Carter Ave, Denton, MD 21629

Showing Results 441 - 480, Page 12 of 18

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