15,675

Caroline County, MD Homes

Section Image Section Image
    • 6 Maple Ave, Ridgely, MD 21660
      6 Maple Ave, Ridgely, MD 21660
      6 Maple Ave, Ridgely, MD 21660
      /48

      Est $330,934 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,492 Sq Ft

      6 Maple Ave, Ridgely, MD 21660

      6 Maple Ave, Ridgely, MD 21660
  • 121 Edenton Ln, Denton, MD 21629
    121 Edenton Ln, Denton, MD 21629
    121 Edenton Ln, Denton, MD 21629
    /29

    $299,000

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

    121 Edenton Ln, Denton, MD 21629

    This charming rancher offers 3 bedrooms and 2 full bathrooms, nestled on a spacious .5-acre lot. Recent updates include new LVP flooring throughout, a roof replacement in 2018, and newer HVAC, water heater, furnace, siding, and gutter guards (2017). Outside enjoy a new deck and walkways, patio, and large treelined backyard, offering privacy. Located just minutes from downtown Denton and major

    Alicia Gannon Dulin Benson & Mangold, LLC

    121 Edenton Ln, Denton, MD 21629
  • 402 Lot 3 N S Sunset Ave, Greensboro, MD 21639
    402 Lot 3 N S Sunset Ave, Greensboro, MD 21639
    402 Lot 3 N S Sunset Ave, Greensboro, MD 21639
    /5

    $46,000 Sold Dec 10, 2025

    402 Lot 3 N S Sunset Ave, Greensboro, MD 21639

    • Land
    • 0.27 Acre
    • $170,370 per Acre

    Last Sold Summary

    • 195 Days On Market

    Last Listing Agent Lisa Knotts Coldwell Banker Realty

    402 Lot 3 N S Sunset Ave, Greensboro, MD 21639
    • 128 Bloomingdale Ave, Federalsburg, MD 21632
      128 Bloomingdale Ave, Federalsburg, MD 21632
      128 Bloomingdale Ave, Federalsburg, MD 21632
      /15

      Est $177,021 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,316 Sq Ft

      128 Bloomingdale Ave, Federalsburg, MD 21632

      128 Bloomingdale Ave, Federalsburg, MD 21632
  • 0 Asbury Dr, Denton, MD 21629
    0 Asbury Dr, Denton, MD 21629
    0 Asbury Dr, Denton, MD 21629
    /24

    $153,000 Under Contract

    • Land
    • 3 Acres
    • $51,000 per Acre

    0 Asbury Dr, Denton, MD 21629

    Discover your ideal homesite in the scenic Asbury on the Choptank community, where peaceful living meets convenient access. This expansive 3-acre lot is perc approved for a three-bedroom septic system. Within this sought-after community, residents enjoy well-maintained roads, a private nature trail, and exclusive access to a community deepwater dock on the Choptank River. Ideal for boating

    Coard Benson Benson & Mangold, LLC

    0 Asbury Dr, Denton, MD 21629
  • 125 Riverwalk Terrace, Federalsburg, MD 21632
    125 Riverwalk Terrace, Federalsburg, MD 21632
    125 Riverwalk Terrace, 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 $232,052

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

    125 Riverwalk Terrace, Federalsburg, MD 21632
    • 25095 Trunk Line Rd, Henderson, MD 21640
      25095 Trunk Line Rd, Henderson, MD 21640
      25095 Trunk Line Rd, Henderson, MD 21640
      /25

      Est $363,033 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,520 Sq Ft

      25095 Trunk Line Rd, Henderson, MD 21640

      25095 Trunk Line Rd, Henderson, MD 21640
  • 26732 Idlewild Rd, Federalsburg, MD 21632
    26732 Idlewild Rd, Federalsburg, MD 21632
    26732 Idlewild Rd, Federalsburg, MD 21632
    /15

    $215,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft

    26732 Idlewild Rd, Federalsburg, MD 21632

    Cute 2 bedroom one story on quiet street. Metal roof. One car garage. Large room off of the kitchen has lots of possibilities, along with the closed in back porch. Updated bathroom. New Andersen windows 2024. New mini Split 2021. Night Owl security with six working cameras. Seamless gutter 2025. Septic cleaned and inspected 2025. Close to nature trails and not far from the boat ramp. Just enough

    Michael Shipley Benson & Mangold, LLC.

    26732 Idlewild Rd, Federalsburg, MD 21632
  • 141 Riverwalk Terrace, Federalsburg, MD 21632
    141 Riverwalk Terrace, Federalsburg, MD 21632
    141 Riverwalk Terrace, Federalsburg, MD 21632
    /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

    D.R. Horton Riverwalk Terrace

    141 Riverwalk Terrace, Federalsburg, MD 21632
    • 5132 Clark Canning House Rd, Federalsburg, MD 21632
      5132 Clark Canning House Rd, Federalsburg, MD 21632
      5132 Clark Canning House Rd, Federalsburg, MD 21632
      /31

      Est $628,534 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,200 Sq Ft

      5132 Clark Canning House Rd, Federalsburg, MD 21632

      5132 Clark Canning House Rd, Federalsburg, MD 21632
  • 129 Hobbs St, Greensboro, MD 21639
    129 Hobbs St, Greensboro, MD 21639
    /2

    $273,990 Pending

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

    129 Hobbs St, Greensboro, MD 21639

    **Red Tag Sales Event now through January 25, 2026! Was $276,990 Now: $273,990! Home must close on or before 3/31/2026.** Discover 129 Hobbs Street, a new home under-construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms, two bathrooms, and a two-car driveway. As you enter the home through the front

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

    129 Hobbs St, Greensboro, MD 21639
  • 9709 Foy Rd, Denton, MD 21629
    9709 Foy Rd, Denton, MD 21629
    9709 Foy Rd, Denton, MD 21629
    /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 $155,333

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    9709 Foy Rd, Denton, MD 21629
    • 306 N Academy St, Greensboro, MD 21639
      306 N Academy St, Greensboro, MD 21639
      306 N Academy St, Greensboro, MD 21639
      /20

      Est $277,263 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,440 Sq Ft

      306 N Academy St, Greensboro, MD 21639

      306 N Academy St, Greensboro, MD 21639
  • 0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660
    /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
  • 213 S 6th St, Denton, MD 21629
    213 S 6th St, Denton, MD 21629
    213 S 6th St, 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 $273,688

    Last Listing Agent Christian Schou Berkshire Hathaway HomeServices PenFed Realty

    213 S 6th St, Denton, MD 21629
    • 13274 Greensboro Rd, Greensboro, MD 21639
      13274 Greensboro Rd, Greensboro, MD 21639
      13274 Greensboro Rd, Greensboro, MD 21639
      /26

      Est $330,328 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft

      13274 Greensboro Rd, Greensboro, MD 21639

      13274 Greensboro Rd, Greensboro, MD 21639
  • 0 Bloomingdale Ave Unit MDCM2006762, Federalsburg, MD 21632
    0 Bloomingdale Ave Unit MDCM2006762, Federalsburg, MD 21632
    0 Bloomingdale Ave Unit MDCM2006762, Federalsburg, MD 21632
    /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
  • 7 S 7th St, Denton, MD 21629
    7 S 7th St, Denton, MD 21629
    7 S 7th St, Denton, MD 21629
    /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 $218,268

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    7 S 7th St, Denton, MD 21629
    • 105 Chamber St, Preston, MD 21655
      105 Chamber St, Preston, MD 21655
      105 Chamber St, Preston, MD 21655
      /6

      Est $289,548 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,140 Sq Ft

      105 Chamber St, Preston, MD 21655

      105 Chamber St, Preston, MD 21655
  • 0 Iron Gate Rd Unit MDCM2004762, Federalsburg, MD 21632
    0 Iron Gate Rd Unit MDCM2004762, Federalsburg, MD 21632
    0 Iron Gate Rd Unit MDCM2004762, Federalsburg, MD 21632
    /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
  • 133 Hobbs St, Greensboro, MD 21639
    133 Hobbs St, Greensboro, MD 21639
    133 Hobbs 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 K Wood D.R. Horton Realty of Virginia, LLC

    133 Hobbs St, Greensboro, MD 21639
    • 22510 Ash Blvd, Preston, MD 21655
      22510 Ash Blvd, Preston, MD 21655
      22510 Ash Blvd, Preston, MD 21655
      /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,612 Sq Ft

      22510 Ash Blvd, Preston, MD 21655

      22510 Ash Blvd, Preston, MD 21655
  • 158 Wright St, Preston, MD 21655
    158 Wright St, Preston, MD 21655
    158 Wright St, Preston, MD 21655
    /34

    $225,000

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    158 Wright St, Preston, MD 21655

    Step back in time with this charming 3-bedroom, 2-bathroom home built in 1890, located in the heart of Preston. Full of character and original details, this home offers a unique opportunity to restore and customize a piece of local history. The inviting living room features a cozy fireplace, perfect for relaxing evenings. A large laundry room and a separate den/office provide flexibility and

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    158 Wright St, Preston, MD 21655
  • 618 Liberty Rd, Federalsburg, MD 21632
    618 Liberty Rd, Federalsburg, MD 21632
    618 Liberty Rd, Federalsburg, MD 21632
    /44

    $329,900 Sold Feb 13, 2025

    618 Liberty Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Built 1957

    Last Sold Summary

    • $165/SF
    • 251 Days On Market

    Current Estimated Value $348,016

    Last Listing Agent Valerie Brown Charles C. Powell, Inc. Realtors

    618 Liberty Rd, Federalsburg, MD 21632
    • 3498 Pepper Rd, Federalsburg, MD 21632
      3498 Pepper Rd, Federalsburg, MD 21632
      3498 Pepper Rd, Federalsburg, MD 21632
      /17

      Est $460,326 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft

      3498 Pepper Rd, Federalsburg, MD 21632

      3498 Pepper Rd, Federalsburg, MD 21632
  • 0 Laurel Ln, Denton, MD 21629
    0 Laurel Ln, Denton, MD 21629
    0 Laurel Ln, Denton, MD 21629
    /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
  • 8320 Detour Rd, Denton, MD 21629
    8320 Detour Rd, Denton, MD 21629
    8320 Detour Rd, Denton, MD 21629
    /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 $103,906

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    8320 Detour Rd, Denton, MD 21629
    • 1211 Painted Fern Rd, Denton, MD 21629
      1211 Painted Fern Rd, Denton, MD 21629
      1211 Painted Fern Rd, Denton, MD 21629
      /14

      Est $428,238 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,238 Sq Ft

      1211 Painted Fern Rd, Denton, MD 21629

      1211 Painted Fern Rd, Denton, MD 21629
  • 113 Maple Ave, Goldsboro, MD 21636
    113 Maple Ave, Goldsboro, MD 21636
    113 Maple Ave, Goldsboro, MD 21636
    /17

    $230,000

    • 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
  • 12760 Cow Barn Rd, Ridgely, MD 21660
    12760 Cow Barn Rd, Ridgely, MD 21660
    12760 Cow Barn Rd, Ridgely, MD 21660
    /21

    $25,000 Sold Mar 18, 2025

    12760 Cow Barn Rd, Ridgely, MD 21660

    • Land
    • 3.55 Acres
    • $7,042 per Acre

    Last Sold Summary

    • 143 Days On Market

    Current Estimated Value $26,187

    Last Listing Agent Jennifer Young Keller Williams Realty

    12760 Cow Barn Rd, Ridgely, MD 21660
    • 28012 Bloomery Rd, Federalsburg, MD 21632
      28012 Bloomery Rd, Federalsburg, MD 21632
      28012 Bloomery Rd, Federalsburg, MD 21632
      /32

      Est $236,811 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,548 Sq Ft

      28012 Bloomery Rd, Federalsburg, MD 21632

      28012 Bloomery Rd, Federalsburg, MD 21632
  • 103 Park Ave Unit 36203275, Greensboro, MD 21639
    103 Park Ave Unit 36203275, Greensboro, MD 21639
    103 Park Ave Unit 36203275, Greensboro, MD 21639
    /24

    $286,990 New Construction

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

    SULLIVAN Plan at Kinnamon Meadows, Greensboro, MD 21639

    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 boasts stainless steel appliances, modern cabinetry, and an optional island with seating that is perfect for casual

    D.R. Horton Builder
    103 Park Ave Unit 36203275, Greensboro, MD 21639
  • 24316 Auction Rd, Preston, MD 21655
    24316 Auction Rd, Preston, MD 21655
    24316 Auction Rd, Preston, MD 21655
    /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 $372,843

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    24316 Auction Rd, Preston, MD 21655
    • 23904 Bridgetown Rd, Goldsboro, MD 21636
      23904 Bridgetown Rd, Goldsboro, MD 21636
      23904 Bridgetown Rd, Goldsboro, MD 21636
      /15

      Est $220,269 Not Listed For Sale

      • Studio
      • 1,608 Sq Ft

      23904 Bridgetown Rd, Goldsboro, MD 21636

      23904 Bridgetown Rd, Goldsboro, MD 21636
  • 7 W Belle St, Ridgely, MD 21660
    7 W Belle St, Ridgely, MD 21660
    7 W Belle St, Ridgely, MD 21660
    /18

    $445,000

    • 0.5 Baths
    • 3,321 Sq Ft

    7 W Belle St, Ridgely, MD 21660

    Over 3,300 sq. ft. two-story building, constructed in 2006, offers endless potential with a little imagination. Previously a pharmacy, gift shop, and ice cream parlor, it could easily be transformed into a fantastic four-bedroom, 2.5-bath residence or adapted for other mixed-use purposes. Both levels feature open, flexible layouts—ready to be reimagined to suit your vision. Located in the

    Traci Jordan Meredith Fine Properties

    7 W Belle St, Ridgely, MD 21660
  • 4631 Everlea Ct, Preston, MD 21655
    4631 Everlea Ct, Preston, MD 21655
    4631 Everlea Ct, Preston, MD 21655
    /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 $480,447

    Last Listing Agent Elizabeth Tryon Coldwell Banker Realty

    4631 Everlea Ct, Preston, MD 21655
    • 1901 Blue Heron Dr, Denton, MD 21629
      1901 Blue Heron Dr, Denton, MD 21629
      1901 Blue Heron Dr, Denton, MD 21629
      /33

      Est $278,510 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,640 Sq Ft

      1901 Blue Heron Dr, Denton, MD 21629

      1901 Blue Heron Dr, Denton, MD 21629
  • 505 Maryland Ave, Ridgely, MD 21660
    505 Maryland Ave, Ridgely, MD 21660
    505 Maryland Ave, Ridgely, MD 21660
    /23

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    505 Maryland Ave, Ridgely, MD 21660

    Welcome to this beautifully updated 3-bedroom, 2-bath rancher located in the charming town of Ridgely, Maryland. Renovated just about two years ago, this home has been lovingly maintained and offers stylish, move-in-ready living with modern finishes throughout. The open-concept kitchen features granite countertops, a spacious island perfect for entertaining, soft-close cabinetry, and

    Kaitlyn Collins Benson & Mangold, LLC

    505 Maryland Ave, Ridgely, MD 21660
  • 125 Bloomingdale Ave, Federalsburg, MD 21632
    125 Bloomingdale Ave, Federalsburg, MD 21632
    125 Bloomingdale Ave, Federalsburg, MD 21632
    /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

    Last Listing Agent Daniel Demers Sell Your Home Services

    125 Bloomingdale Ave, Federalsburg, MD 21632
    • 25938 Beauchamp Branch Rd, Denton, MD 21629
      25938 Beauchamp Branch Rd, Denton, MD 21629
      25938 Beauchamp Branch Rd, Denton, MD 21629
      /38

      Est $467,752 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,016 Sq Ft

      25938 Beauchamp Branch Rd, Denton, MD 21629

      25938 Beauchamp Branch Rd, Denton, MD 21629

Showing Results 161 - 200, Page 5 of 18

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