15,709

Caroline County, MD Homes

Section Image
    • /33

      Est $323,107 Not Listed For Sale

      7881 Dyer Rd, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 1,961 Sq Ft
      • Built 1972
      7881 Dyer Rd, Denton, MD 21629

      Last Sold Summary

      • 11% Above List Price
      • $148/SF
      • 40 Days On Market
      • Last Sold Price $289,900
      • Oct 20, 2023

      Last Listing Agent Douglas Reyes Smart Realty, LLC

  • /11

    $3,700,000

    8019 Patten Rd, Denton, MD 21629

    Poultry farm features a total of 60.57 acres (40 acres tillable, 8.5 acres wooded, 1.5-acre retention pond) and a 40x72 shop that has garage parking and a separate space that could be finished for permanent living. Located approx. 5 miles from the DE line. Expired site evaluation-no septic on property.

    Tambra Reagan CALLAWAY FARNELL AND MOORE

    8019 Patten Rd, Denton, MD 21629
  • /64

    $565,000 Sold Oct 08, 2025

    6074 Newton Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft
    • Built 1993

    Last Sold Summary

    • $274/SF
    • 64 Days On Market

    Current Estimated Value $559,022

    Last Listing Agent James Bent Benson & Mangold, LLC

    6074 Newton Rd, Preston, MD 21655
    • /61

      Est $435,475 Not Listed For Sale

      1146 Osprey Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,082 Sq Ft
      • Built 2006
      1146 Osprey Ln, Denton, MD 21629

      Last Sold Summary

      • 8% Above List Price
      • $131/SF
      • 2 Days On Market
      • Last Sold Price $403,000
      • Jul 21, 2023

      Last Listing Agent Whitney Westover First Coast Realty LLC

  • /50

    $629,000

    • 5 Beds
    • 2.5 Baths
    • 2,920 Sq Ft

    24276 Asbury Dr, Denton, MD 21629

    Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Expansive lot sizes give you the privacy needed within a walkable neighborhood. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A large rear screened-in porch to watch the local wildlife opens onto extensive

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    24276 Asbury Dr, Denton, MD 21629
  • /18

    $250,000 Sold Oct 14, 2025

    508 W Sunset Ave, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1975

    Last Sold Summary

    • $223/SF
    • 8 Days On Market

    Current Estimated Value $247,232

    Last Listing Agent Erene Katris Coldwell Banker Realty

    508 W Sunset Ave, Greensboro, MD 21639
    • /30

      Est $277,585 Not Listed For Sale

      1612 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,244 Sq Ft
      • Built 2006
      1612 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 8% Above List Price
      • $115/SF
      • 3 Days On Market
      • Last Sold Price $258,000
      • Aug 28, 2023

      Last Listing Agent Mary Wagner Cummings & Co. Realtors

  • /111

    $939,000

    • 4 Beds
    • 3.5 Baths
    • 2,520 Sq Ft

    8416 Harmony Rd, Denton, MD 21629

    Discover a truly rare opportunity where lifestyle, income potential, and homeownership come together on this expansive 12.7-acre, two-parcel property zoned rural—offering unmatched flexibility and endless possibilities.Currently operating as a productive orchard, greenhouse operation, and microgreens business, this property is thoughtfully equipped for both personal enjoyment and

    Casey Neves The Parker Group

    8416 Harmony Rd, Denton, MD 21629
  • /21

    $309,000 Sold Nov 03, 2025

    27381 Greenwood Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,922 Sq Ft
    • Built 1900

    Last Sold Summary

    • $161/SF
    • 66 Days On Market

    Current Estimated Value $313,653

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

    27381 Greenwood Rd, Denton, MD 21629
    • /38

      Est $269,653 Not Listed For Sale

      1606 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 3.5 Baths
      • 2,268 Sq Ft
      • Built 2006
      1606 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 6% Above List Price
      • $112/SF
      • 2 Days On Market
      • Last Sold Price $255,000
      • Feb 20, 2024

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

  • /53

    $445,000

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

    23283 Magnolia Hills Rd, Denton, MD 21629

    This charming ranch-style home in the desirable Magnolia Hill community offers a perfect blend of comfort and modern living. With 3 spacious bedrooms and 2 full bathrooms, the open floor plan with cathedral ceilings invites natural light, creating a warm and welcoming atmosphere. The eat-in kitchen features an island, ideal for casual meals, while the adjoining dining area is perfect for

    Tricia Wilson Wilson Realty & Staging LLC

    23283 Magnolia Hills Rd, Denton, MD 21629
  • /20

    $280,000 Sold Apr 17, 2026

    1303 Fairfield Ct, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 1,426 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $196/SF
    • 30 Days On Market

    Current Estimated Value $288,551

    Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

    1303 Fairfield Ct, Denton, MD 21629
    • /38

      Est $232,239 Not Listed For Sale

      26875 Barclay Rd, Marydel, MD 21649

      • 3 Beds
      • 1 Bath
      • 1,404 Sq Ft
      • Built 1951
      26875 Barclay Rd, Marydel, MD 21649

      Last Sold Summary

      • 2% Above List Price
      • $162/SF
      • 47 Days On Market
      • Last Sold Price $228,000
      • Aug 14, 2024

      Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

  • /57

    $479,900

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

    7837 Shore Dr, Preston, MD 21655

    Two Johns – Charming Home in a Sought-After Waterfront Community Nestled between Preston and Denton in the desirable Two Johns subdivision, this beautifully maintained 4-bedroom, 2.5-bath home offers a rare blend of comfort, style, and location. Just a few houses away from the public boat landing, residents enjoy easy water access for boating, kayaking, or fishing. Take in serene water views from

    Eddie Matthews Benson & Mangold, LLC

    7837 Shore Dr, Preston, MD 21655
  • /99

    $420,000 Sold Aug 29, 2025

    208 Bloomingdale Ave, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 3,734 Sq Ft
    • Built 1930

    Last Sold Summary

    • $112/SF
    • 16 Days On Market

    Current Estimated Value $430,559

    Last Listing Agent Blaine Williamson McClain-Williamson Realty, LLC

    208 Bloomingdale Ave, Federalsburg, MD 21632
    • /73

      Est $636,735 Not Listed For Sale

      20810 Frazier Point Ln, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 2,226 Sq Ft
      • Built 1970
      20810 Frazier Point Ln, Preston, MD 21655

      Last Sold Summary

      • 2% Below List Price
      • $292/SF
      • 229 Days On Market
      • Last Sold Price $650,000
      • Feb 13, 2025

      Last Listing Agent Barbara McCaffrey Redfin Corp

  • /71

    $1,099,999 Under Contract

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

    7904 Clark Rd, Denton, MD 21629

    This ±45-acre previously certified organic farm is located just south of Denton and offers a well-rounded combination of productive farmland, agricultural infrastructure, and residential living. The property includes approximately ±41 acres of tillable ground equipped with a subsurface irrigation system fed by six on-site wells, providing efficient and reliable water delivery for a wide range of

    Jesse Highling The Land Group

    7904 Clark Rd, Denton, MD 21629
  • /31

    $227,000 Sold Jun 09, 2025

    326 N Main St, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,592 Sq Ft
    • Built 1915

    Last Sold Summary

    • $143/SF
    • 188 Days On Market

    Current Estimated Value $233,352

    Last Listing Agent Billy Mister Keller Williams Realty

    326 N Main St, Federalsburg, MD 21632
    • /28

      Est $280,659 Not Listed For Sale

      1614 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,244 Sq Ft
      • Built 2006
      1614 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 4% Above List Price
      • $121/SF
      • 2 Days On Market
      • Last Sold Price $270,500
      • Jan 22, 2024

      Last Listing Agent Marcy Gaines Century 21 New Millennium

  • /2

    $179,000

    • 2 Beds
    • 2 Baths
    • 968 Sq Ft

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

    Rare Opportunity ! Built 1922 as a school and converted into condo units. Many of the original elements make each building unique. With massive windows different architectural elements makes each unit distinctive. Open floor plan with updated appliances make this turn key for its next resident.. This unit has Two comfortable size bedrooms, two full baths, washer and dryer. There is an owner

    Kat Thompson Benson & Mangold, LLC.

    107 N School St Unit 3B, Greensboro, MD 21639
  • /28

    $285,000 Sold May 09, 2025

    21959 Main St, Hillsboro, MD 21641

    • 4 Beds
    • 2 Baths
    • 2,168 Sq Ft
    • Built 1885

    Last Sold Summary

    • $131/SF
    • 9 Days On Market

    Current Estimated Value $312,473

    Last Listing Agent Jimmy White Long & Foster Real Estate, Inc.

    21959 Main St, Hillsboro, MD 21641
    • /13

      Est $263,333 Not Listed For Sale

      25 Greenridge Ave, Ridgely, MD 21660

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1993
      25 Greenridge Ave, Ridgely, MD 21660

      Last Sold Summary

      • 7% Above List Price
      • $243/SF
      • 7 Days On Market
      • Last Sold Price $245,000
      • Mar 15, 2024

      Last Listing Agent Marti McGinty Chesapeake Real Estate Associates, LLC

  • /20

    $950,000

    • 3 Beds
    • 2 Baths
    • 2,320 Sq Ft

    6401 Laurel Grove Rd, Denton, MD 21629

    Nestled on an expansive 52.08-acre estate, this stunning ranch-style farm offers a harmonious blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle in a serene rural setting. The property boasts a traditional architectural design, complemented by aluminum siding that enhances its timeless appeal. Step inside to discover a thoughtfully designed interior that exudes

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    6401 Laurel Grove Rd, Denton, MD 21629
  • /19

    $325,000 Sold Aug 08, 2025

    1206 Trice Meadows Cir, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,470 Sq Ft
    • Built 2018

    Last Sold Summary

    • $221/SF
    • 86 Days On Market

    Current Estimated Value $346,684

    Last Listing Agent Bonnie Johnson Keller Williams Realty

    1206 Trice Meadows Cir, Denton, MD 21629
    • /56

      Est $386,983 Not Listed For Sale

      12710 Greensboro Rd, Greensboro, MD 21639

      • 3 Beds
      • 2.5 Baths
      • 1,472 Sq Ft
      • Built 1950
      12710 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 1% Below List Price
      • $265/SF
      • 5 Days On Market
      • Last Sold Price $389,900
      • Oct 23, 2024

      Last Listing Agent Scott Judy Coldwell Banker Waterman Realty

  • /6

    $400,000

    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft

    26784 Bilbrough Rd, Goldsboro, MD 21636

    Welcome to your private slice of Eastern Shore living in Goldsboro. Set on 4.7 secluded acres, this 2022-built home offers the space, comfort, and modern features today’s market demands. With over 2,100 square feet, 4 bedrooms, and 2 full baths, the layout is open, bright, and designed for seamless everyday living. Step inside to a spacious floor plan that flows effortlessly from room to

    Sandra Bradley Keller Williams Select Realtors of Easton

    26784 Bilbrough Rd, Goldsboro, MD 21636
  • /26

    $280,000 Sold Aug 25, 2025

    104 S 8th St, Denton, MD 21629

    • 2 Beds
    • 1.5 Baths
    • 1,055 Sq Ft
    • Built 1973

    Last Sold Summary

    • $265/SF
    • 7 Days On Market

    Current Estimated Value $280,190

    Last Listing Agent Tony Letizia VRA Realty

    104 S 8th St, Denton, MD 21629
    • /41

      Est $293,034 Not Listed For Sale

      1915 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,640 Sq Ft
      • Built 2006
      1915 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 9% Above List Price
      • $102/SF
      • 13 Days On Market
      • Last Sold Price $269,000
      • Mar 24, 2025

      Last Listing Agent Pamela Ackermann-Doll RE/MAX

  • /19

    $950,000

    • 3 Beds
    • 2 Baths
    • 2,320 Sq Ft

    6401 Laurel Grove Rd, Denton, MD 21629

    Nestled on an expansive 52.08-acre estate, this stunning ranch-style farm offers a harmonious blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle in a serene rural setting. The property boasts a traditional architectural design, complemented by aluminum siding that enhances its timeless appeal. Step inside to discover a thoughtfully designed interior that exudes

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    6401 Laurel Grove Rd, Denton, MD 21629
  • /106

    $540,000 Sold Sep 04, 2025

    8534 Briar Patch Dr, Denton, MD 21629

    • 4 Beds
    • 3 Baths
    • 3,039 Sq Ft
    • Built 1995

    Last Sold Summary

    • $178/SF
    • 68 Days On Market

    Current Estimated Value $550,034

    Last Listing Agent Alana Taylor Worthington Realty Group, LLC

    8534 Briar Patch Dr, Denton, MD 21629
    • /31

      Est $350,051 Not Listed For Sale

      25797 Spring Branch Dr, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 1998
      25797 Spring Branch Dr, Greensboro, MD 21639

      Last Sold Summary

      • $272/SF
      • 54 Days On Market
      • Last Sold Price $350,000
      • May 31, 2024

      Last Listing Agent Rick Parreco RE/MAX

  • /2

    $32,500

    • Land
    • 30,056 Sq Ft
    • $47,101 per Acre

    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660

    Just next to the quaint town of Ridgely, this .69 acre lot also comes with a bonus lot highlighted in photos. Buy and hold as an investment or see if you can perc.

    Michael Rosendale Rosendale Realty

    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660
  • /65

    $450,000 Sold Sep 12, 2025

    135 Walnut St, Ridgely, MD 21660

    • 4 Beds
    • 4 Baths
    • 3,408 Sq Ft
    • Built 2005

    Last Sold Summary

    • $132/SF
    • 4 Days On Market

    Current Estimated Value $459,861

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    135 Walnut St, Ridgely, MD 21660
    • /26

      Est $229,138 Not Listed For Sale

      1510 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,692 Sq Ft
      • Built 2004
      1510 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 2% Above List Price
      • $133/SF
      • 3 Days On Market
      • Last Sold Price $225,000
      • Dec 08, 2023

      Last Listing Agent Dan Foster Long & Foster

  • /3

    $55,000

    • Land
    • 14,810 Sq Ft
    • $161,765 per Acre

    507 W Central Ave, Federalsburg, MD 21632

    Discover a unique opportunity to create your dream home on this spacious 0.34-acre parcel of land, nestled in a serene suburban setting. This property offers a blank canvas for your vision, allowing you to design a residence that perfectly suits your lifestyle and preferences. Imagine waking up each day to the gentle sounds of nature, with the peaceful ambiance of a suburban neighborhood

    Joni Barrow Coldwell Banker Realty

    507 W Central Ave, Federalsburg, MD 21632
  • /48

    $471,500 Sold Apr 30, 2026

    111 Riverview Ln, Greensboro, MD 21639

    • 4 Beds
    • 1.5 Baths
    • 2,000 Sq Ft
    • Built 1977

    Last Sold Summary

    • 5% Above List Price
    • $236/SF

    Current Estimated Value $451,737

    Last Listing Agent John Howard Long & Foster Real Estate, Inc.

    111 Riverview Ln, Greensboro, MD 21639
    • /80

      Est $359,644 Not Listed For Sale

      24300 Robins Creek Rd, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,624 Sq Ft
      • Built 1979
      24300 Robins Creek Rd, Preston, MD 21655

      Last Sold Summary

      • 5% Below List Price
      • $234/SF
      • 127 Days On Market
      • Last Sold Price $379,900
      • Apr 25, 2024

      Last Listing Agent Cheryl Jersey-Lecourt Long & Foster

  • /38

    $479,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    11473 Holly Rd, Ridgely, MD 21660

    Welcome to modern country living with room to breathe. This nearly new rancher, only 6 months old, sits on 2.34 private acres with NO HOA, giving you the freedom to truly enjoy your property.Inside, the home features LVP flooring throughout, creating a seamless and durable living space. The stunning kitchen is the heart of the home with sleek cabinetry, gorgeous quartz countertops, and a

    Crystal Smith RE/MAX Executive

    11473 Holly Rd, Ridgely, MD 21660
  • /47

    $365,000 Sold May 22, 2025

    25782 Burrsville Rd, Denton, MD 21629

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

    Last Sold Summary

    • $272/SF
    • 68 Days On Market

    Current Estimated Value $403,728

    Last Listing Agent Brittany Gough RE/MAX One

    25782 Burrsville Rd, Denton, MD 21629
    • /17

      Est $386,986 Not Listed For Sale

      205 N Main St, Greensboro, MD 21639

      • 5 Beds
      • 3 Baths
      • 3,876 Sq Ft
      • Built 1890
      205 N Main St, Greensboro, MD 21639

      Last Sold Summary

      • 31% Above List Price
      • $76/SF
      • 301 Days On Market
      • Last Sold Price $295,000
      • Apr 10, 2024

      Last Listing Agent Pamela Geib Long & Foster

Showing Results 401 - 440, Page 11 of 18

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