15,671

Caroline County, MD Homes

Section Image Section Image
    • 26302 Sennett Rd, Denton, MD 21629
      26302 Sennett Rd, Denton, MD 21629
      26302 Sennett Rd, Denton, MD 21629
      /5

      Est $47,073 Not Listed For Sale

      26302 Sennett Rd, Denton, MD 21629

      26302 Sennett Rd, Denton, MD 21629
  • 208 N Main St, Federalsburg, MD 21632
    208 N Main St, Federalsburg, MD 21632
    208 N Main St, Federalsburg, MD 21632
    /22

    $150,000

    • 4 Beds
    • 1.5 Baths
    • 2,668 Sq Ft

    208 N Main St, Federalsburg, MD 21632

    Traditional Victorian. 4 bedrooms, 1 1/2 baths, basement, attic, wraparound porch.Sold as is. Cash or conventional financing. Estate of Bonnie Jefferson.

    Barton Johnson/not int Marshy Hope Realty LLC

    208 N Main St, Federalsburg, MD 21632
  • 123 Briarwood Cir, Denton, MD 21629
    123 Briarwood Cir, Denton, MD 21629
    123 Briarwood Cir, Denton, MD 21629
    /30

    $340,000 Sold Aug 20, 2025

    123 Briarwood Cir, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Built 2015

    Last Sold Summary

    • $170/SF
    • 64 Days On Market

    Current Estimated Value $349,368

    Last Listing Agent Lou Chirgott Core Maryland Real Estate LLC

    123 Briarwood Cir, Denton, MD 21629
    • 13056 Hog Lot Rd, Ridgely, MD 21660
      13056 Hog Lot Rd, Ridgely, MD 21660
      13056 Hog Lot Rd, Ridgely, MD 21660
      /79

      Est $557,049 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft

      13056 Hog Lot Rd, Ridgely, MD 21660

      13056 Hog Lot Rd, Ridgely, MD 21660
  • 504 Pintail St, Greensboro, MD 21639
    504 Pintail St, Greensboro, MD 21639
    504 Pintail St, Greensboro, MD 21639
    /26

    $299,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    504 Pintail St, Greensboro, MD 21639

    Practically New Home in Greensboro, MD — Built in 2024!Why wait to build when you can move right into this stunning, barely lived-in home? Built in 2024 and meticulously maintained, this property offers the perfect blend of modern style and low-maintenance living.Step inside to an inviting open floor plan filled with natural light. The spacious kitchen features sleek granite countertops,

    Kaitlyn Collins Benson & Mangold, LLC

    504 Pintail St, Greensboro, MD 21639
  • 0 Temple Rd Unit MDCM2006034, Marydel, MD 21649
    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649
    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649
    /18

    $475,000 Sold Dec 22, 2025

    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649

    • Land
    • 53.01 Acres
    • $8,961 per Acre

    Last Sold Summary

    • 140 Days On Market

    Last Listing Agent Benjamin Alder The Land Group

    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649
    • 106 Noble Ave, Preston, MD 21655
      106 Noble Ave, Preston, MD 21655
      106 Noble Ave, Preston, MD 21655
      /23

      Est $325,700 Not Listed For Sale

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

      106 Noble Ave, Preston, MD 21655

      106 Noble Ave, Preston, MD 21655
  • 0 Quail Ct Unit MDCM2006644, Greensboro, MD 21639
    0 Quail Ct Unit MDCM2006644, Greensboro, MD 21639
    0 Quail Ct Unit MDCM2006644, Greensboro, MD 21639
    /14

    $399,000

    • 3 Beds
    • 2 Baths

    0 Quail Ct Unit MDCM2006644, Greensboro, MD 21639

    Quick Delivery – To Be Built Rancher!This beautifully designed rancher offers 3 bedrooms and 2 full baths with an open-concept floor plan and cathedral ceilings in the main living area. The builder includes a generous package of upgrades at no additional cost. Enjoy an oversized attached two-car garage and a rear deck perfect for outdoor living. Situated on a cleared 1-acre lot in a private

    Barbara Blosser Long & Foster Real Estate, Inc.

    0 Quail Ct Unit MDCM2006644, Greensboro, MD 21639
  • 3069 Choptank Rd, Preston, MD 21655
    3069 Choptank Rd, Preston, MD 21655
    3069 Choptank Rd, Preston, MD 21655
    /88

    $930,000 Sold Sep 30, 2025

    3069 Choptank Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,512 Sq Ft
    • Built 2003

    Last Sold Summary

    • $370/SF
    • 11 Days On Market

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    3069 Choptank Rd, Preston, MD 21655
    • 230 Main St, Preston, MD 21655
      230 Main St, Preston, MD 21655
      230 Main St, Preston, MD 21655
      /53

      Est $433,183 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 3,208 Sq Ft

      230 Main St, Preston, MD 21655

      230 Main St, Preston, MD 21655
  • 3622 Choptank Rd, Preston, MD 21655
    3622 Choptank Rd, Preston, MD 21655
    3622 Choptank Rd, Preston, MD 21655
    /44

    $299,900 Pending

    • 2 Beds
    • 1.5 Baths
    • 1,700 Sq Ft

    3622 Choptank Rd, Preston, MD 21655

    Beautifully maintained and move-in ready 2BR/1.5BA expanded Rancher on a sprawling lot in the open landscape of Wright's Wharf. Pull into the long driveway that wraps around to the attached two-car garage, make your way past lush green lawns, adult trees and landscaping, on the way to the front door of your forever home. Step inside to a home with tons of natural light, recessed lighting, an open

    Brooke Tephabock VYBE Realty

    3622 Choptank Rd, Preston, MD 21655
  • 17 Greenridge Ave, Ridgely, MD 21660
    17 Greenridge Ave, Ridgely, MD 21660
    17 Greenridge Ave, Ridgely, MD 21660
    /16

    $265,000 Sold Jul 31, 2025

    17 Greenridge Ave, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,136 Sq Ft
    • Built 1991

    Last Sold Summary

    • $233/SF
    • 7 Days On Market

    Current Estimated Value $278,709

    Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

    17 Greenridge Ave, Ridgely, MD 21660
    • 104 Noble Ave, Preston, MD 21655
      104 Noble Ave, Preston, MD 21655
      104 Noble Ave, Preston, MD 21655
      /17

      Est $315,752 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,236 Sq Ft

      104 Noble Ave, Preston, MD 21655

      104 Noble Ave, Preston, MD 21655
  • 120 Julie Ln, Federalsburg, MD 21632
    120 Julie Ln, Federalsburg, MD 21632
    120 Julie Ln, Federalsburg, MD 21632
    /27

    $220,990 Pending

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

    120 Julie Ln, Federalsburg, MD 21632

    Explore 120 Julie Lane, a new home in the welcoming Riverwalk Terrace community of Federalsburg, MD. The Jefferson is an open-concept 1,365 square foot two-story interior townhome with three bedrooms, two and a half bathrooms, and on-street parking. The first floor is spacious with a large, thoughtfully designed kitchen with ample gray cabinet space, granite countertops, stainless steel

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

    120 Julie Ln, Federalsburg, MD 21632
  • 614 Market St, Denton, MD 21629
    614 Market St, Denton, MD 21629
    614 Market St, Denton, MD 21629
    /29

    $325,000 Sold Oct 06, 2025

    614 Market St, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,508 Sq Ft
    • Built 1890

    Last Sold Summary

    • $130/SF
    • 53 Days On Market

    Last Listing Agent Michael Bozek Michael J. Bozek

    614 Market St, Denton, MD 21629
    • 240 Main St, Preston, MD 21655
      240 Main St, Preston, MD 21655
      240 Main St, Preston, MD 21655
      /60

      Est $376,919 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,088 Sq Ft

      240 Main St, Preston, MD 21655

      240 Main St, Preston, MD 21655
  • 25999 Fox Grape Rd, Greensboro, MD 21639
    25999 Fox Grape Rd, Greensboro, MD 21639
    25999 Fox Grape Rd, Greensboro, MD 21639
    /27

    $379,000

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft

    25999 Fox Grape Rd, Greensboro, MD 21639

    Welcome to this beautifully updated 4-bedroom, 2-bath home nestled in the peaceful Fox Grape Farms community. This move-in-ready property features a recently remodeled kitchen and bathrooms, along with refinished hardwood floors that add warmth and charm throughout. Set on a serene half-acre wooded lot, the home offers wonderful outdoor living with an 8' x 14' enclosed porch, a rear deck with a

    Amy Betts Coldwell Banker Realty

    25999 Fox Grape Rd, Greensboro, MD 21639
  • 517 Franklin St, Denton, MD 21629
    517 Franklin St, Denton, MD 21629
    517 Franklin St, Denton, MD 21629
    /22

    $275,000 Sold Mar 11, 2025

    517 Franklin St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft
    • Built 1900

    Last Sold Summary

    • $255/SF
    • 108 Days On Market

    Current Estimated Value $290,906

    Last Listing Agent Amanda Morgan Brenton Realty Group

    517 Franklin St, Denton, MD 21629
    • 111 Fooks Ave, Preston, MD 21655
      111 Fooks Ave, Preston, MD 21655
      111 Fooks Ave, Preston, MD 21655
      /14

      Est $392,427 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,072 Sq Ft

      111 Fooks Ave, Preston, MD 21655

      111 Fooks Ave, Preston, MD 21655
  • 103 Chamber St, Preston, MD 21655
    103 Chamber St, Preston, MD 21655
    103 Chamber St, Preston, MD 21655
    /12

    $135,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    103 Chamber St, Preston, MD 21655

    This Colonial home features timeless architecture and thoughtful design. The property offers solid construction and classic appeal, making it an excellent opportunity for discerning buyers. This distinctive property presents an outstanding opportunity for transformation and value creation. The established neighborhood setting combines small-town charm with practical accessibility to essential

    Pamela Geib Long & Foster Real Estate, Inc.

    103 Chamber St, Preston, MD 21655
  • 22490 Ash Blvd, Preston, MD 21655
    22490 Ash Blvd, Preston, MD 21655
    22490 Ash Blvd, Preston, MD 21655
    /46

    $348,000 Sold Oct 14, 2025

    22490 Ash Blvd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 2001

    Last Sold Summary

    • $188/SF
    • 22 Days On Market

    Last Listing Agent Kathryn Tennant Douglas Realty, LLC

    22490 Ash Blvd, Preston, MD 21655
    • 113 Noble Ave, Preston, MD 21655
      113 Noble Ave, Preston, MD 21655
      113 Noble Ave, Preston, MD 21655
      /38

      Est $262,323 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,314 Sq Ft

      113 Noble Ave, Preston, MD 21655

      113 Noble Ave, Preston, MD 21655
  • 1105 Market St, Denton, MD 21629
    1105 Market St, Denton, MD 21629
    1105 Market St, Denton, MD 21629
    /29

    $259,000 Under Contract

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

    1105 Market St, Denton, MD 21629

    Back Active- Buyer financing fell thru!!!!!One Level Living! Nothing to do but Move-in! Home built in 2022. Home features Large Open Floor Plan, Kitchen Dining Combo with Breakfast Bar. Spacious Family Room. Primary Bedroom has two nice size closets an additional walk-in closet inside primary Bathroom w/ Double sinks and a Walk-in Shower! 2 other bedrooms are nice size. Full Bath in the Hall

    Kathleen Brenton Brenton Realty Group

    1105 Market St, Denton, MD 21629
  • 3457 Jefferson Pond Rd, Federalsburg, MD 21632
    3457 Jefferson Pond Rd, Federalsburg, MD 21632
    3457 Jefferson Pond Rd, Federalsburg, MD 21632
    /21

    $297,500 Sold Apr 07, 2025

    3457 Jefferson Pond Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2024

    Last Sold Summary

    • $221/SF
    • 145 Days On Market

    Last Listing Agent Amy Herr Keller Williams Realty

    3457 Jefferson Pond Rd, Federalsburg, MD 21632
    • 107 Fooks Ave, Preston, MD 21655
      107 Fooks Ave, Preston, MD 21655
      107 Fooks Ave, Preston, MD 21655
      /14

      Est $422,203 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,950 Sq Ft

      107 Fooks Ave, Preston, MD 21655

      107 Fooks Ave, Preston, MD 21655
  • 334 Deep Shore Rd, Denton, MD 21629
    334 Deep Shore Rd, Denton, MD 21629
    334 Deep Shore Rd, Denton, MD 21629
    /48

    $359,500 Pending

    • 3 Beds
    • 2 Baths
    • 1,640 Sq Ft

    334 Deep Shore Rd, Denton, MD 21629

    Welcome to this adorable 3 bedroom, 2 bath home in the heart of Denton located on a generous 0.46 acre lot that backs up to trees. There is a short walk to Martinak State Park. Inside you will enjoy the recently updated home which includes a new roof, new HVAC, new water heater, water softener system. The bathroom and kitchen has been remodeled. You will see the beautifully refinished living room

    Laura Anthony Benson & Mangold, LLC

    334 Deep Shore Rd, Denton, MD 21629
  • 19 S 8th St, Denton, MD 21629
    19 S 8th St, Denton, MD 21629
    19 S 8th St, Denton, MD 21629
    /9

    $225,000 Sold Jun 11, 2025

    19 S 8th St, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1981

    Last Sold Summary

    • $260/SF
    • 9 Days On Market

    Current Estimated Value $241,201

    Last Listing Agent Myisha Walker Long & Foster Real Estate, Inc.

    19 S 8th St, Denton, MD 21629
    • 27518 Possum Hill Rd, Federalsburg, MD 21632
      27518 Possum Hill Rd, Federalsburg, MD 21632
      27518 Possum Hill Rd, Federalsburg, MD 21632
      /33

      Est $527,466 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,249 Sq Ft

      27518 Possum Hill Rd, Federalsburg, MD 21632

      27518 Possum Hill Rd, Federalsburg, MD 21632
  • 130 Charlotte Ave, Federalsburg, MD 21632
    130 Charlotte Ave, Federalsburg, MD 21632
    130 Charlotte Ave, Federalsburg, MD 21632
    /23

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,646 Sq Ft

    130 Charlotte Ave, Federalsburg, MD 21632

    Welcome to this well-maintained 3BR/2BA home offering convenient one-level living in a quiet Federalsburg neighborhood. Built in 2006, this home features a bright and functional layout with all bedrooms and baths located on the main floor. The brick-front exterior provides great curb appeal, and the spacious 0.43-acre lot offers plenty of outdoor enjoyment. An attached 2-car garage provides

    FRANK LITTLE Berkshire Hathaway HomeServices PenFed Realty

    130 Charlotte Ave, Federalsburg, MD 21632
  • 13061 Logan Ln, Greensboro, MD 21639
    13061 Logan Ln, Greensboro, MD 21639
    13061 Logan Ln, Greensboro, MD 21639
    /19

    $335,000 Sold May 27, 2025

    13061 Logan Ln, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Built 2004

    Last Sold Summary

    • $266/SF
    • 6 Days On Market

    Current Estimated Value $357,202

    Last Listing Agent Megan Carpenter Tesla Realty Group, LLC

    13061 Logan Ln, Greensboro, MD 21639
    • 1103 Trice Meadows Cir, Denton, MD 21629
      1103 Trice Meadows Cir, Denton, MD 21629
      1103 Trice Meadows Cir, Denton, MD 21629
      /37

      Est $405,637 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,816 Sq Ft

      1103 Trice Meadows Cir, Denton, MD 21629

      1103 Trice Meadows Cir, Denton, MD 21629
  • 24029 Meadows Dr, Ridgely, MD 21660
    24029 Meadows Dr, Ridgely, MD 21660
    24029 Meadows Dr, Ridgely, MD 21660
    /39

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft

    24029 Meadows Dr, Ridgely, MD 21660

    Enjoy the best of Eastern Shore living with the tranquility of a quiet, country setting while remaining conveniently located just outside of the quaint little town of Ridgely. This nanticoke rancher features a nice family room addition off the kitchen and is located on a private 2 acre lot on the end of a cul-de-sac. Featuring 3 bedrooms and 2 full baths and a two car garage. This property also

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    24029 Meadows Dr, Ridgely, MD 21660
  • 124 Julie Ln, Federalsburg, MD 21632
    124 Julie Ln, Federalsburg, MD 21632
    124 Julie Ln, Federalsburg, MD 21632
    /28

    $233,990 Sold Aug 20, 2025

    • 1,365 Sq Ft
    • $171/SF
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    124 Julie Ln, Federalsburg, MD 21632

    Discover 124 Julie Lane, a new home in Riverwalk Terrace in Federalsburg, MD. The Jefferson is an open-concept 1,365 square foot two-story end-of-unit townhome with three bedrooms, two and a half bathrooms, and on-street parking. The first floor is spacious with a large, thoughtfully designed kitchen with stylish gray cabinet space, granite countertops, stainless steel appliances, a storage

    D.R. Horton

    124 Julie Ln, Federalsburg, MD 21632
  • 3471 Laurel Grove Rd, Federalsburg, MD 21632
    3471 Laurel Grove Rd, Federalsburg, MD 21632
    /2

    $110,000

    • 3 Beds
    • 1 Bath
    • 888 Sq Ft

    3471 Laurel Grove Rd, Federalsburg, MD 21632

    Looking for a project with potential? This 3-bedroom, 1-bath home in Federalsburg is ready for someone with vision. Offering solid bones and a large detached garage, it’s the perfect opportunity to renovate, customize, and build equity. Whether you’re an investor or a handy buyer wanting a fixer-upper, this property gives you room to make it your own. Great possibilities — bring your ideas and

    Heather Brummell Keller Williams Realty

    3471 Laurel Grove Rd, Federalsburg, MD 21632
  • 0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660
    /7

    $120,000 Sold Mar 20, 2025

    0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660

    • Land
    • 3.75 Acres
    • $32,000 per Acre

    Last Sold Summary

    • 124 Days On Market

    Last Listing Agent Stephan Strothe Washington Fine Properties, LLC

    0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660
    • 344 Meadow Vale Ln, Denton, MD 21629
      344 Meadow Vale Ln, Denton, MD 21629
      344 Meadow Vale Ln, Denton, MD 21629
      /19

      Est $381,933 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,580 Sq Ft

      344 Meadow Vale Ln, Denton, MD 21629

      344 Meadow Vale Ln, Denton, MD 21629
  • 311 Maple Ave, Federalsburg, MD 21632
    311 Maple Ave, Federalsburg, MD 21632
    311 Maple Ave, Federalsburg, MD 21632
    /10

    $135,000

    • 2 Beds
    • 1 Bath
    • 1,230 Sq Ft

    311 Maple Ave, Federalsburg, MD 21632

    This charming 1940 bungalow in the desirable Federalsburg area presents a unique investment opportunity. With a total finished area of 1,230 sq. ft. , this property features 2 bedrooms and 1 full bathroom, making it an attractive option for rental income or resale potential. Estate sale, property is being sold "as-is". No repairs, and contents included to be removed at the expense of the buyer.

    Melissa Tippett TTR Sotheby's International Realty

    311 Maple Ave, Federalsburg, MD 21632
  • 124 Parkland Rd, Greensboro, MD 21639
    124 Parkland Rd, Greensboro, MD 21639
    124 Parkland Rd, Greensboro, MD 21639
    /20

    $267,490 Sold Aug 12, 2025

    • 1,059 Sq Ft
    • $253/SF
    • 2 Beds
    • 2 Baths
    • Built 2025

    124 Parkland Rd, Greensboro, MD 21639

    Discover the Perry in Kinnamon Meadows, a soon-to-be-built 1,059 square foot open concept cottage-style ranch home, offering two bedrooms and two bathrooms at 124 Parkland Road in Greensboro, MD. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests or enjoying family time. The well-equipped kitchen

    D.R. Horton

    124 Parkland Rd, Greensboro, MD 21639
    • 12185 River Rd, Ridgely, MD 21660
      12185 River Rd, Ridgely, MD 21660
      12185 River Rd, Ridgely, MD 21660
      /13

      Est $278,264 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,026 Sq Ft

      12185 River Rd, Ridgely, MD 21660

      12185 River Rd, Ridgely, MD 21660

Showing Results 81 - 120, Page 3 of 18

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