15,698

Caroline County, MD Homes

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  • /35

    $239,900 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 1,756 Sq Ft

    515 Vaughn Ave, Greensboro, MD 21639

    This charming home in Cedar Run is set to shine with a major refresh in 2026, blending modern comforts with classic appeal. Spanning 1,756 sq. ft. , this end-of-row home offers a cozy atmosphere perfect for creating lasting memories. The spacious layout features an attached garage, providing convenience and ease. Nestled in a vibrant community, residents enjoy access to nearby parks, perfect for

    Chad Muse KD Realty Inc

    515 Vaughn Ave, Greensboro, MD 21639
  • /7

    $105,000 Sold Mar 23, 2026

    22691 Sawmill Rd, Ridgely, MD 21660

    • 2 Beds
    • 1 Bath
    • 1,088 Sq Ft
    • Built 1945

    Last Sold Summary

    • 16% Below List Price
    • $97/SF
    • 6 Days On Market

    Current Estimated Value $150,031

    Last Listing Agent Amanda Morgan Brenton Realty Group

    22691 Sawmill Rd, Ridgely, MD 21660
    • /19

      Est $347,166 Not Listed For Sale

      344 Meadow Vale Ln, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,580 Sq Ft
      • Built 2010
      344 Meadow Vale Ln, Denton, MD 21629

      Last Sold Summary

      • 2% Above List Price
      • $215/SF
      • 52 Days On Market

      Last Sold Price $339,000

      Last Listing Agent Bonnie Johnson Keller Williams Realty

  • /26

    $269,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,696 Sq Ft

    311 Holt St, Federalsburg, MD 21632

    Welcome to this beautifully renovated home in the heart of Federalsburg! Every detail has been thoughtfully updated, blending modern finishes with timeless charm. Enjoy a bright and inviting layout, a stylish kitchen with updated features, and refreshed living spaces perfect for both relaxing and entertaining. Recent improvements provide peace of mind, while the overall design offers

    Heather Brummell Keller Williams Realty

    311 Holt St, Federalsburg, MD 21632
  • /32

    $310,000 Sold Feb 20, 2026

    407 Wood Duck Dr, Greensboro, MD 21639

    • 4 Beds
    • 2.5 Baths
    • 1,624 Sq Ft
    • Built 2004

    Last Sold Summary

    • $191/SF
    • 149 Days On Market

    Current Estimated Value $316,767

    Last Listing Agent Kathryn Matic Patterson-Schwartz - Greenville

    407 Wood Duck Dr, Greensboro, MD 21639
    • /13

      Est $264,032 Not Listed For Sale

      12185 River Rd, Ridgely, MD 21660

      • 2 Beds
      • 1 Bath
      • 1,026 Sq Ft
      • Built 1990
      12185 River Rd, Ridgely, MD 21660

      Last Sold Summary

      • 2% Above List Price
      • $253/SF
      • 5 Days On Market

      Last Sold Price $260,000

      Last Listing Agent Kelly Dahle Benson & Mangold, LLC

  • /14

    $120,000 Pending

    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    26471 Three Bridges Rd, Federalsburg, MD 21632

    Opportunity awaits at 26471 Three Bridges Rd in Federalsburg, MD! This partially remodeled 2-bedroom, 2-bath home is ready for your finishing touch. Inside, the property has been taken down to the framing and subflooring, giving you a true blank canvas to bring your vision to life—whether you’re an investor looking for your next project or a buyer ready to customize every detail. Set on nearly a

    LEE MARLAND Keller Williams Realty

    26471 Three Bridges Rd, Federalsburg, MD 21632
  • /28

    $219,990 Sold Apr 25, 2025

    125 Riverwalk Terrace, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2024

    Last Sold Summary

    • $161/SF
    • 42 Days On Market

    Current Estimated Value $211,025

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

    125 Riverwalk Terrace, Federalsburg, MD 21632
    • /12

      Est $1,446,630 Not Listed For Sale

      12786 Holly Rd, Greensboro, MD 21639

      • 2 Beds
      • 1 Bath
      • 1,728 Sq Ft
      • Built 1870
      12786 Holly Rd, Greensboro, MD 21639

      Last Sold Summary

      • 24% Below List Price
      • $1,100/SF
      • 60 Days On Market

      Last Sold Price $1,900,000

      Last Listing Agent Benjamin Alder The Land Group

  • /22

    $499,000 Pending

    • Land
    • 63.16 Acres
    • $7,901 per Acre

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655

    Dover Bridge Road | Preston, MarylandThis 63 ± acre parcel on Dover Bridge Road offers a rare opportunity to own a sizeable tract of woodland conveniently located just four miles from Preston, seven and a half miles from Easton, and about fifteen minutes from Route 50.The property is perc-approved for residential use and includes a forestry management plan documenting that roughly 58

    Coard Benson Benson & Mangold, LLC

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
  • /28

    $229,990 Sold Aug 05, 2025

    141 Riverwalk Terrace, Federalsburg, MD 21632

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

    Move in Ready Sold Summary

    • $168/SF
    • 21 Days On Market

    141 Riverwalk Terrace, Federalsburg, MD 21632
    • /36

      Est $746,202 Not Listed For Sale

      24638 Tribbett Cir, Ridgely, MD 21660

      • 5 Beds
      • 3 Baths
      • 4,521 Sq Ft
      • Built 2010
      24638 Tribbett Cir, Ridgely, MD 21660

      Last Sold Summary

      • 19% Above List Price
      • $138/SF
      • 19 Days On Market

      Last Sold Price $625,000

      Last Listing Agent John Currence BHHS PenFed (actual)

  • /21

    $238,900

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    103 Riverwalk Terrace, Federalsburg, MD 21632

    This is an opportunity to buy in the sold out community of Riverwalk Terrace. The owner stayed at the home a few times some of the appliances never used. Open floor plan 1365 square feet , 3 bedrooms and 2.5 baths easy living. Only 2 years young this unit feels like new, was never a rental barley lived in. also backs up to the woods the private side of the community. Another perk to this location

    Kat Thompson Benson & Mangold, LLC.

    103 Riverwalk Terrace, Federalsburg, MD 21632
  • /3

    $94,900 Sold Oct 03, 2025

    9709 Foy Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 2,312 Sq Ft
    • Built 1900

    Last Sold Summary

    • $41/SF
    • 13 Days On Market

    Current Estimated Value $165,000

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    9709 Foy Rd, Denton, MD 21629
    • /12

      Est $372,472 Not Listed For Sale

      1108 Trice Meadows Cir, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 2023
      1108 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 6% Above List Price
      • $233/SF
      • 147 Days On Market

      Last Sold Price $349,900

      Last Listing Agent Michelle DiDonato Island Realty, LLC

  • /3

    $265,000

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

    10819 Greensboro Rd, Denton, MD 21629

    This home will be a Total Renovation in 2026. Consisting of 2 BR and 1 Bath. Situated on almost a half ac. Lovely back yard, and new Well.

    Barbara Beaudet Brenton Realty Group

    10819 Greensboro Rd, Denton, MD 21629
  • /31

    $260,000 Sold Aug 01, 2025

    213 S 6th St, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1983

    Last Sold Summary

    • $232/SF
    • 5 Days On Market

    Current Estimated Value $256,625

    Last Listing Agent Christian Schou TTR Sotheby's International Realty

    213 S 6th St, Denton, MD 21629
    • /74

      Not Listed For Sale

      4439 Bethlehem Rd, Preston, MD 21655

      • 5 Beds
      • 2.5 Baths
      • 2,560 Sq Ft
      • Built 1900
      4439 Bethlehem Rd, Preston, MD 21655

      Last Sold Summary

      • 33% Below List Price
      • $326/SF
      • 106 Days On Market

      Last Sold Price $835,000

      Last Listing Agent Mickey Hayward Sunset Properties

  • /16

    $230,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,920 Sq Ft

    204 Maple Ave, Greensboro, MD 21639

    Classic victorian with all of the historic charm on a quiet street in the beautiful town of Greensboro. Renovated in 2024. Beautiful hardwood floors, an updated kitchen and main bathroom. Lovely front porch, outdoor shed and carport in the back. Central air conditioning system. Beautiful lifestyle centrally located close to all that the Eastern Shore offers. Nearby shopping and restaurant options

    Ursula Encarnacion Long & Foster Real Estate, Inc.

    204 Maple Ave, Greensboro, MD 21639
  • /18

    $195,000 Sold Jun 27, 2025

    7 S 7th St, Denton, MD 21629

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 1880

    Last Sold Summary

    • $162/SF
    • 33 Days On Market

    Current Estimated Value $203,059

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    7 S 7th St, Denton, MD 21629
    • /48

      Est $333,105 Not Listed For Sale

      6 Maple Ave, Ridgely, MD 21660

      • 4 Beds
      • 2 Baths
      • 2,492 Sq Ft
      • Built 1957
      6 Maple Ave, Ridgely, MD 21660

      Last Sold Summary

      • 19% Above List Price
      • $112/SF
      • 11 Days On Market

      Last Sold Price $280,000

      Last Listing Agent Phill Whitby Long & Foster

  • /29

    $219,000

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft

    417 N Academy St, Greensboro, MD 21639

    Discover the charm of this delightful ranch-style home, perfectly nestled on a generous 0.26-acre lot. Built in 1993, this well-maintained residence boasts a warm and inviting atmosphere, ideal for creating lasting memories. With 936 square feet of thoughtfully designed living space, this home features two cozy bedrooms and a full bathroom, providing comfort and convenience for everyday living.

    Lawrence Doyle Long & Foster Real Estate, Inc.

    417 N Academy St, Greensboro, MD 21639
  • /23

    $286,990 Sold Feb 06, 2026

    133 Hobbs St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft
    • Built 2025

    Last Sold Summary

    • $235/SF
    • 36 Days On Market

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

    133 Hobbs St, Greensboro, MD 21639
    • /15

      Est $148,639 Not Listed For Sale

      128 Bloomingdale Ave, Federalsburg, MD 21632

      • 5 Beds
      • 3.5 Baths
      • 4,316 Sq Ft
      • Built 1860
      128 Bloomingdale Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 15% Below List Price
      • $41/SF
      • 245 Days On Market

      Last Sold Price $175,000

      Last Listing Agent Pamela Geib Long & Foster

  • /7

    $127,000

    • Land
    • 4.14 Acres
    • $30,676 per Acre

    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660

    Discover the ideal blend of tranquil nature and prime location! 4.14 acres with mature trees, offering unparalleled privacy and peaceful country living in one of the area's most scenic subdivisions -- all just minutes away from Ridgely and Denton, and less than 1 mile from North Caroline High School. Build your dream home on this beautiful level building lot, providing an even terrain

    Stephan Strothe Washington Fine Properties, LLC

    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660
  • /14

    $95,000 Sold May 22, 2025

    8320 Detour Rd, Denton, MD 21629

    • Land
    • 2.09 Acres
    • $45,455 per Acre

    Last Sold Summary

    • 135 Days On Market

    Current Estimated Value $97,965

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    8320 Detour Rd, Denton, MD 21629
    • /25

      Est $359,176 Not Listed For Sale

      25095 Trunk Line Rd, Henderson, MD 21640

      • 3 Beds
      • 2 Baths
      • 1,520 Sq Ft
      • Built 2003
      25095 Trunk Line Rd, Henderson, MD 21640

      Last Sold Summary

      • 14% Above List Price
      • $207/SF
      • 3 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Melissa Murray Compass

  • /6

    $375,000

    • Land
    • 5.3 Acres
    • $70,755 per Acre

    0 Bloomingdale Ave Unit MDCM2006762, Federalsburg, MD 21632

    5.3 acre site on Bloomingdale Avenue, Federalsburg. Situated next to Dollar General, across from ProvidentState Bank and very near Royal Farm Store and McDonalds. Contains 3 parcels sold as a package. Publicutilities to the property. Shared access with Dollar General. C1 Commercial zoning allows a wide variety ofuses including: office, general business and professional uses, banks,

    Florence Adams SVN |Miller Commercial Real Estate

    0 Bloomingdale Ave Unit MDCM2006762, Federalsburg, MD 21632
  • /33

    $350,000 Sold Sep 26, 2025

    24316 Auction Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,438 Sq Ft
    • Built 1975

    Last Sold Summary

    • $243/SF
    • 19 Days On Market

    Current Estimated Value $358,517

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    24316 Auction Rd, Preston, MD 21655
    • /31

      Est $432,051 Not Listed For Sale

      5132 Clark Canning House Rd, Federalsburg, MD 21632

      • 4 Beds
      • 2.5 Baths
      • 2,200 Sq Ft
      • Built 1930
      5132 Clark Canning House Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 14% Below List Price
      • $227/SF
      • 353 Days On Market

      Last Sold Price $500,000

      Last Listing Agent Bobby Gorski The Land Group

  • /46

    $75,000 Under Contract

    • Land
    • 8.43 Acres
    • $8,897 per Acre

    0 Iron Gate Rd Unit MDCM2004762, Federalsburg, MD 21632

    Bring your imagination to this gorgeous 8.43 wooded acreage in Federalsburg! No current permits pulled! No builder tie in! This property was perc approved back in the 1980's & owner hasn't done anything with it since. No well or septic currently on property.

    Megan Rosendale Rosendale Realty

    0 Iron Gate Rd Unit MDCM2004762, Federalsburg, MD 21632
  • /26

    $475,000 Sold Oct 15, 2025

    4631 Everlea Ct, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 2,228 Sq Ft
    • Built 1997

    Last Sold Summary

    • $213/SF
    • 4 Days On Market

    Current Estimated Value $464,785

    Last Listing Agent Elizabeth Tryon Coldwell Banker Realty

    4631 Everlea Ct, Preston, MD 21655
    • /20

      Est $277,094 Not Listed For Sale

      306 N Academy St, Greensboro, MD 21639

      • 2 Beds
      • 1 Bath
      • 1,440 Sq Ft
      • Built 1948
      306 N Academy St, Greensboro, MD 21639

      Last Sold Summary

      • 15% Above List Price
      • $167/SF
      • 169 Days On Market

      Last Sold Price $240,000

      Last Listing Agent Stacie Luhrman Benson & Mangold, LLC

  • /2

    $225,000

    • Land
    • 0 Acre

    11920 Central Ave, Ridgely, MD 21660

    Priced for a quick sale! This great property offers over 16 acres of level land with frontage on three roads: Central Avenue, Henry Road, and Holly Plains Drive. Zoned R1, this lot presents endless possibilities—whether you're looking to hold, subdivide, or develop. Located just outside the Ridgely city limits and within close proximity to the town center, this property is ideally positioned for

    Sam Benkirane Proplocate Realty, LLC

    11920 Central Ave, Ridgely, MD 21660
  • /21

    $59,900 Sold Nov 24, 2025

    125 Bloomingdale Ave, Federalsburg, MD 21632

    • 4 Beds
    • 1 Bath
    • 1,696 Sq Ft
    • Built 1875

    Last Sold Summary

    • $35/SF
    • 22 Days On Market

    Current Estimated Value $124,333

    Last Listing Agent Daniel Demers Sell Your Home Services

    125 Bloomingdale Ave, Federalsburg, MD 21632
    • /7

      Est $289,380 Not Listed For Sale

      128 Mill St, Greensboro, MD 21639

      • 3 Beds
      • 1 Bath
      • 1,890 Sq Ft
      • Built 1981
      128 Mill St, Greensboro, MD 21639

      Last Sold Summary

      • 9% Above List Price
      • $140/SF
      • 18 Days On Market

      Last Sold Price $265,000

      Last Listing Agent Phill Whitby Long & Foster

  • /6

    $85,000

    • Land
    • 1.15 Acres
    • $73,913 per Acre

    0 Laurel Ln, Denton, MD 21629

    Beautiful, wooded lot ready to be built on available in established Forest Landing. Conveniently located between Denton and Easton. Lot has approved perc for a 4 bedroom mound system. Community offers a private beach area, picnic tables, great spot to launch your canoe or kayak or do a little fishing. Not many opportunities to build your next home in a mature neighborhood left around.

    Michael Bozek Michael J. Bozek

    0 Laurel Ln, Denton, MD 21629
  • /27

    $219,990 Sold Aug 29, 2025

    143 Riverwalk Terrace, Federalsburg, MD 21632

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

    Last Sold Summary

    • $161/SF
    • 6 Days On Market

    Current Estimated Value $215,272

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

    143 Riverwalk Terrace, Federalsburg, MD 21632
    • /26

      Est $330,267 Not Listed For Sale

      13274 Greensboro Rd, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft
      • Built 1925
      13274 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 27% Above List Price
      • $139/SF
      • 18 Days On Market

      Last Sold Price $260,000

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • /17

    $230,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft

    113 Maple Ave, Goldsboro, MD 21636

    Welcome to the pleasures of small town living in this updated Farmhouse. This 3 bed 2 bath home sits on a .23 acre lot with most of the land in the backyard for relaxing and entertaining. Plenty of room for gardens or playground area. Outbuilding for extra storage. Enjoy the evenings on the back deck overlooking the yard or enjoy the front porch with coffee and listen to the rain. Contract will

    Roger Boyce Chesapeake Real Estate Associates, LLC

    113 Maple Ave, Goldsboro, MD 21636

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