15,718

Caroline County, MD Homes

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  • /57

    $479,900

    $15K PRICE DROP Pending
    • 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
  • /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 $374,559

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    24887 Holsinger Ln, Ridgely, MD 21660
    • /12

      Est $327,891

      Not Listed For Sale

      2 Greenridge Ave, Ridgely, MD 21660

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1991
      2 Greenridge Ave, Ridgely, MD 21660

      Last Sold Summary

      • 101 Days On Market

  • /10

    $159,900

    $19K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 968 Sq Ft

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

    Big reduction! 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

    Kat Thompson Benson & Mangold, LLC.

    107 N School St Unit 3B, Greensboro, MD 21639
  • /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 $187,444

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    210 Denton Rd, Federalsburg, MD 21632
    • /25

      Est $301,692

      Not Listed For Sale

      9585 Legion Rd, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 1,291 Sq Ft
      • Built 1956
      9585 Legion Rd, Denton, MD 21629

      Last Sold Summary

      • 64 Days On Market

  • /20

    $950,000

    $150K PRICE DROP
    • 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
  • /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 $325,267

    Last Listing Agent Laura Anderson Coldwell Banker Realty

    22329 Tanyard Rd, Preston, MD 21655
    • /19

      Est $282,686

      Not Listed For Sale

      11401 Greensboro Rd, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,036 Sq Ft
      • Built 1940
      11401 Greensboro Rd, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

  • /6

    $360,000

    $40K PRICE DROP
    • 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
  • /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
    • /50

      Est $404,225

      Not Listed For Sale

      294 Tidewater Cir, Preston, MD 21655

      • 5 Beds
      • 2.5 Baths
      • 2,886 Sq Ft
      • Built 2006
      294 Tidewater Cir, Preston, MD 21655

      Last Sold Summary

      • 84 Days On Market

  • /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
  • /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
    • /8

      Est $472,268

      Not Listed For Sale

      23209 Gilpin Point Rd, Preston, MD 21655

      • 2 Beds
      • 1 Bath
      • 1,560 Sq Ft
      • Built 1965
      23209 Gilpin Point Rd, Preston, MD 21655

      Last Sold Summary

      • 127 Days On Market

  • /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
  • /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 $506,572

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    11575 Maplewood Dr, Ridgely, MD 21660
    • /17

      Est $219,478

      Not Listed For Sale

      1115 Market St, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 788 Sq Ft
      • Built 1950
      1115 Market St, Denton, MD 21629

      Last Sold Summary

      • 7 Days On Market

  • /3

    $49,000

    $6K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $144,118 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
  • /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
    • /33

      Est $315,728

      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

      • 40 Days On Market

  • /69

    $740,000

    Under Contract
    • 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
  • /2

    $50,000

    Sold May 29, 2026

    17485 Henderson Rd, Marydel, MD 21649

    • Land
    • 3,049 Sq Ft
    • $714,286 per Acre

    Last Sold Summary

    • 7 Days On Market

    Current Estimated Value $95,000

    Last Listing Agent Andrew Beaven Wright Real Estate

    17485 Henderson Rd, Marydel, MD 21649
    • /61

      Est $430,554

      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

      • 2 Days On Market

  • /10

    $175,000

    $10K PRICE DROP Under Contract
    • 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
  • /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 $327,907

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    6315 Harmony Rd, Preston, MD 21655
    • /30

      Est $272,484

      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

      • 3 Days On Market

  • /61

    $630,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 3,725 Sq Ft

    26927 Boyce Mill Rd, Greensboro, MD 21639

    Nestled on 5 beautiful acres, this spacious 4-bedroom, 3.5-bath home offers the perfect blend of privacy, comfort, and country living. Approximately 1.8 acres are wooded, providing a peaceful backdrop and frequent visits from local wildlife, while the remaining acreage is cleared and ideal for outdoor enjoyment. The inviting front porch overlooks the private rural setting, while the interior

    Barbara Blosser Long & Foster Real Estate, Inc.

    26927 Boyce Mill Rd, Greensboro, MD 21639
  • /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 $198,334

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

    6561 Bell Creek Rd, Preston, MD 21655
    • /38

      Est $264,859

      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

      • 2 Days On Market

  • /4

    $21,000

    $14K PRICE DROP
    • 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

    $273,990

    Sold Jan 15, 2026

    129 Hobbs St, Greensboro, MD 21639

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

    Move in Ready Sold Summary

    • 1% Below List Price
    • $232/SF
    • 14 Days On Market

    D.R. Horton Kinnamon Meadows

    129 Hobbs St, Greensboro, MD 21639
    • /38

      Est $235,838

      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

      • 47 Days On Market

  • /23

    $190,000

    $10K PRICE DROP Under Contract
    • 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
  • /13

    $235,000

    Sold Jul 31, 2025

    513 Vaughn Ave, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1996

    Last Sold Summary

    • $204/SF
    • 8 Days On Market

    Current Estimated Value $236,343

    Last Listing Agent Chad Muse KD Realty Inc

    513 Vaughn Ave, Greensboro, MD 21639
    • /73

      Est $617,822

      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

      • 229 Days On Market

  • /34

    $269,999

    $20K PRICE DROP Under Contract
    • 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
  • /59

    $385,000

    Sold Nov 07, 2025

    502 N Academy St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 2,378 Sq Ft
    • Built 1960

    Last Sold Summary

    • $162/SF
    • 105 Days On Market

    Current Estimated Value $366,756

    Last Listing Agent Chris Rosendale CR Realty

    502 N Academy St, Greensboro, MD 21639
    • /28

      Est $277,788

      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

      • 2 Days On Market

  • /30

    $355,000

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    8140 Haven St, Denton, MD 21629

    This charming ranch-style home, built in 1986, offers a perfect blend of comfort and functionality. Minutes to Tuckahoe Creek boat ramp! With 1,300 sq. ft. of well-designed space, it features three inviting bedrooms and two full bathrooms, including a primary suite with a walk-in closet and a tub/shower. The traditional floor plan is enhanced by built-ins and ceiling fans, creating a cozy

    Mary Haddaway Benson & Mangold, LLC

    8140 Haven St, Denton, MD 21629

Showing Results 441 - 480, Page 12 of 18

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