15,577

Caroline County, MD Homes

Section Image
  • /8

    $79,900

    Pending
    • Land
    • 4.31 Acres
    • $18,538 per Acre

    Lot 1 E Sunset Ave, Greensboro, MD 21639

    Large wooded lot on the outside of town. Perc approved for a 2' mound system. Located at the corner of Sunset Ave and River Rds. 4.3 acres Some forest conservation area. Only four lots in this subdivision and only three lots available.

    Marcia Rostien Long & Foster Real Estate, Inc.

    Lot 1 E Sunset Ave, Greensboro, MD 21639
  • /2

    $100,000

    Sold Feb 20, 2026

    3471 Laurel Grove Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 888 Sq Ft
    • Built 1965

    Last Sold Summary

    • 9% Below List Price
    • $113/SF
    • 31 Days On Market

    Current Estimated Value $165,099

    Last Listing Agent Heather Brummell Keller Williams Realty

    3471 Laurel Grove Rd, Federalsburg, MD 21632
    • /5

      Est $103,469

      Not Listed For Sale

      21373 Dover Bridge Rd, Preston, MD 21655

      • Built 1890
      21373 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  • /32

    $419,000

    Open Sat 2PM - 4PM
    • 5 Beds
    • 2.5 Baths
    • 2,250 Sq Ft

    109 Walnut St, Ridgely, MD 21660

    5 BEDROOMS — 2,250 SQ FT — MOVE-IN READY — 2-CAR GARAGE — ESTABLISHED LISTER ESTATES Looking for the space of a larger home without the wait, construction process, or uncertainty of new construction? Why wait for new construction when you can enjoy the space, comfort and established charm of a beautifully maintained Colonial in desirable Lister Estates? Offering 5 bedrooms, 2.5 baths and

    Camille Bullard Coldwell Banker Realty

    109 Walnut St, Ridgely, MD 21660
  • /26

    $269,000

    Sold Apr 23, 2026

    311 Holt St, Federalsburg, MD 21632

    • 3 Beds
    • 1.5 Baths
    • 1,696 Sq Ft
    • Built 1895

    Last Sold Summary

    • $159/SF
    • 5 Days On Market

    Current Estimated Value $249,532

    Last Listing Agent Heather Brummell Keller Williams Realty

    311 Holt St, Federalsburg, MD 21632
    • /39

      Est $534,574

      Not Listed For Sale

      21303 Dover Bridge Rd, Preston, MD 21655

      • 3 Beds
      • 3 Baths
      • 2,607 Sq Ft
      • Built 1998
      21303 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  • /2

    $87,500

    Under Contract
    • Land
    • 2 Acres
    • $43,750 per Acre

    15441 Cutoff Rd, Henderson, MD 21640

    Discover the perfect canvas for your dream home on this expansive 2-acre parcel of land, where possibilities abound! Nestled in a serene setting, this property offers ample space to create a sanctuary tailored to your lifestyle. This generous lot provides the ideal backdrop for your vision, whether you envision a sprawling estate, a cozy retreat, or a vibrant garden oasis. The location offers a

    Amanda Morgan Brenton Realty Group

    15441 Cutoff Rd, Henderson, MD 21640
  • /10

    $125,000

    Sold Jan 15, 2026

    311 Maple Ave, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 1,230 Sq Ft
    • Built 1940

    Last Sold Summary

    • 7% Below List Price
    • $102/SF
    • 4 Days On Market

    Current Estimated Value $246,217

    Last Listing Agent Melissa Tippett TTR Sotheby's International Realty

    311 Maple Ave, Federalsburg, MD 21632
    • /23

      Est $317,187

      Not Listed For Sale

      106 Noble Ave, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1995
      106 Noble Ave, Preston, MD 21655

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Sid Campen Charles C. Powell, Inc. Realtors

  • /12

    $575,000

    • Land
    • 61.88 Acres
    • $9,292 per Acre

    17619 Melville Rd, Henderson, MD 21640

    The Melville Rd Farm is located on the east side of Melville Road and is bordered to the north by Trunk Line Road. The property includes approximately 51± acres of tillable ground along with 11± acres of wooded areas primarily situated around drainage ditches, providing natural transitions and wildlife cover. Two transmission lines run through the center of the farm, offering access corridors and

    Benjamin Alder The Land Group

    17619 Melville Rd, Henderson, MD 21640
  • /29

    $275,000

    Sold Oct 21, 2025

    104 Roe St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • Built 1948

    Last Sold Summary

    • $228/SF
    • 3 Days On Market

    Current Estimated Value $271,171

    Last Listing Agent Nora Turner Long & Foster Real Estate, Inc.

    104 Roe St, Greensboro, MD 21639
    • /53

      Est $437,767

      Not Listed For Sale

      230 Main St, Preston, MD 21655

      • 5 Beds
      • 5 Baths
      • 3,208 Sq Ft
      • Built 1890
      230 Main St, Preston, MD 21655

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Shane Slacum LPT Realty, LLC

  • /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
  • /26

    $185,000

    Sold Nov 10, 2025

    311 Reliance Ave, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 1,224 Sq Ft
    • Built 1950

    Last Sold Summary

    • $151/SF
    • 7 Days On Market

    Current Estimated Value $195,027

    Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    311 Reliance Ave, Federalsburg, MD 21632
    • /17

      Est $299,272

      Not Listed For Sale

      104 Noble Ave, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,236 Sq Ft
      • Built 1995
      104 Noble Ave, Preston, MD 21655

      Last Sold Summary

      • 76 Days On Market

      Last Listing Agent Amy Endzel Keller Williams Select Realtors of Annapolis

  • /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
  • /5

    $46,000

    Sold Dec 10, 2025

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

    • Land
    • 11,761 Sq Ft
    • $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
    • /14

      Est $389,798

      Not Listed For Sale

      111 Fooks Ave, Preston, MD 21655

      • 4 Beds
      • 2 Baths
      • 2,072 Sq Ft
      • Built 1974
      111 Fooks Ave, Preston, MD 21655

      Last Sold Summary

      • 323 Days On Market

      Last Listing Agent Barbara Nichols Results Realty Inc.

  • /40

    $280,000

    $25K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,884 Sq Ft

    407 W Sunset Ave, Greensboro, MD 21639

    Charming 5BR detached home, located in a quiet neighborhood in Greensboro. Experience the great outdoors in your own backyard on a nearly 1/2 acre lot, adjacent to 140 acres of farmland. Enjoy the 'Sunset' from the 320 sf sunroom with sliding glass doors, or sit outside to watch the sunrise on the new 230 sf wooden front porch. Several updates include replacement windows, upgraded plumbing &

    Raphael Szendro R&R Executive Realty

    407 W Sunset 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 $118,696

    Last Listing Agent Amanda Morgan Brenton Realty Group

    22691 Sawmill Rd, Ridgely, MD 21660
    • /14

      Est $404,416

      Not Listed For Sale

      107 Fooks Ave, Preston, MD 21655

      • 4 Beds
      • 2.5 Baths
      • 1,950 Sq Ft
      • Built 2023
      107 Fooks Ave, Preston, MD 21655

      Last Sold Summary

      • 154 Days On Market

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /10

    $345,000

    • 4 Beds
    • 3 Baths
    • 3,258 Sq Ft

    14671 Fox Chase Cir, Ridgely, MD 21660

    Welcome to this spacious ranch-style home situated on approximately 1.98 private, wooded acres, offering an exceptional combination of space, privacy, and versatility.With approximately 3,258 square feet of living space, including two additions to the original home, this expansive property features 4 bedrooms and 3 full bathrooms, along with flexible living areas that can accommodate a home

    Keaton OTTLEY Conway Real Estate

    14671 Fox Chase Cir, Ridgely, MD 21660
  • /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 $323,790

    Last Listing Agent Kathryn Matic Patterson-Schwartz - Greenville

    407 Wood Duck Dr, Greensboro, MD 21639
    • /37

      Est $398,675

      Not Listed For Sale

      1103 Trice Meadows Cir, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 2,816 Sq Ft
      • Built 2010
      1103 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

  • /15

    $99,000

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,100 Sq Ft

    101 S University Ave, Federalsburg, MD 21632

    AS IS! GREAT INVESTMENT PROPERTY! This charming 3-bedroom, 1-bathroom traditional home, built in 1944, offers a solid investment opportunity with its AS IS condition gives you a blank slate to modernize this home to fit your needs! The traditional floor plan maximizes space, creating a warm and inviting atmosphere perfect for comfortable living. With a manageable lot size of 0.09 acres,

    Joni Barrow Coldwell Banker Realty

    101 S University Ave, 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 $167,397

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    9709 Foy Rd, Denton, MD 21629
    • /31

      Est $359,899

      Not Listed For Sale

      1109 Trice Meadows Cir, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,772 Sq Ft
      • Built 2010
      1109 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Laura Anderson Coldwell Banker Realty

  • /23

    $215,000

    Pending
    • Studio
    • 2,532 Sq Ft

    1 Central Ave, Ridgely, MD 21660

    Welcome to 1 Central Ave, perfectly positioned in the heart of downtown Ridgely! This versatile mixed‑use building offers endless potential with both commercial and residential spaces under one roof.The first‑floor commercial unit features an inviting open foyer/reception area, four private office spaces, a half bathroom, and a spacious office/conference room toward the rear—ideal for

    Amanda Morgan Brenton Realty Group

    1 Central Ave, Ridgely, MD 21660
  • /37

    $295,000

    Sold Apr 10, 2026

    1106 Osprey Ln, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,752 Sq Ft
    • Built 2004

    Last Sold Summary

    • $168/SF
    • 15 Days On Market

    Current Estimated Value $293,104

    Last Listing Agent Barbara McCaffrey Redfin Corp

    1106 Osprey Ln, Denton, MD 21629
    • /49

      Est $380,996

      Not Listed For Sale

      1111 Trice Meadows Cir, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,138 Sq Ft
      • Built 2009
      1111 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Dan Foster Long & Foster Real Estate, Inc.

  • /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
  • /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
    • /19

      Est $363,187

      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

      • 52 Days On Market

      Last Listing Agent Bonnie Johnson Keller Williams Realty

  • /50

    $225,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 891 Sq Ft

    6149 Bethlehem Rd, Preston, MD 21655

    Charming and full of potential, this 2-bedroom, 1-bath home offers an excellent opportunity in Preston! Set on approximately 0.55 acres, this 891-square-foot single-level home features a spacious deck and a practical layout ready for its next chapter. Whether you're searching for an affordable primary residence, a weekend getaway, or an investment opportunity, this property is worth a look. Enjoy

    Heather Brummell Keller Williams Realty

    6149 Bethlehem Rd, Preston, MD 21655
  • /21

    $319,000

    Sold Jul 17, 2026

    1308 Chesapeake Dr, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 2004

    Last Sold Summary

    • 9% Below List Price
    • $218/SF
    • 30 Days On Market

    Current Estimated Value $315,542

    Last Listing Agent Bonnie Johnson Keller Williams Realty

    1308 Chesapeake Dr, Denton, MD 21629
    • /13

      Est $270,695

      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

      • 5 Days On Market

      Last Listing Agent Kelly Dahle Benson & Mangold, LLC

  • /2

    $499,999

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,613 Sq Ft

    25660 Cherry Blossom Ln, Denton, MD 21629

    Beautiful to be built new construction on 1.8 acres just outside Denton. This home offers 4 bedrooms, 2 full baths, great open kitchen with island, pantry, separate laundry room, large family room plus dining area. The crawl space will be conditioned for total peace of mind. The garage is huge measuring 32x22 and will be fully insulated with R19 Batts insulation. There will be a slider leading to

    Bonnie Johnson Keller Williams Realty

    25660 Cherry Blossom Ln, Denton, MD 21629
  • /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 $352,458

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    24316 Auction Rd, Preston, MD 21655
    • /12

      Est $1,423,030

      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

      • 60 Days On Market

      Last Listing Agent Benjamin Alder The Land Group

  • /2

    $180,000

    $95K PRICE DROP
    • Land
    • 0 Sq Ft

    11920 Central Ave, Ridgely, MD 21660

    Huge Price Drop – Act Fast Before It’s Gone! (Serious Buyers Only)This exceptional property features over 16 acres of level land with frontage on three roads: Central Avenue, Henry Road, and Holly Plains Drive. Zoned R-1, it offers outstanding potential—perfect for holding, subdividing, or developing.Located just outside the Ridgely city limits and close to the town center, the property

    Sam Benkirane Proplocate Realty, LLC

    11920 Central Ave, Ridgely, MD 21660

Showing Results 161 - 200, Page 5 of 18

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