15,577

Caroline County, MD Homes

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    • /62

      Est $743,374

      Not Listed For Sale

      23079 Tuckahoe Springs Dr, Denton, MD 21629

      • 3 Beds
      • 4 Baths
      • 3,737 Sq Ft
      • Built 1974
      23079 Tuckahoe Springs Dr, Denton, MD 21629

      Last Sold Summary

      • 112 Days On Market

      Last Listing Agent Melanie Hopkins Coldwell Banker Chesapeake Real Estate Company

  • /4

    $1,200,000

    $400K PRICE DROP
    • Land
    • 11 Acres
    • $109,091 per Acre

    0 Liberty (Rifkin Village) Rd Unit MDCM2007390, Federalsburg, MD 21632

    Ready for Development! Owner financing possible with down payment. Terms negotiable. 43 lots within the Town limits of Federalsburg, Maryland. Total lot space as currently platted is 478,596 sq ft or 11 acres, according to public records. Total property area including the unbuilt road space is roughly 13 acres. Right-of-ways to the property are currently platted from Liberty Rd, Bernard Ave, and

    Aaron Dixon Berkshire Hathaway HomeServices PenFed Realty

    0 Liberty (Rifkin Village) Rd Unit MDCM2007390, Federalsburg, MD 21632
  • /30

    $289,000

    Sold Jun 30, 2026

    14185 Drapers Mill Rd, Greensboro, MD 21639

    • 4 Beds
    • 1 Bath
    • 1,352 Sq Ft
    • Built 1910

    Last Sold Summary

    • 3% Below List Price
    • $214/SF
    • 56 Days On Market

    Current Estimated Value $284,002

    Last Listing Agent John Lyons Crown Homes Real Estate

    14185 Drapers Mill Rd, Greensboro, MD 21639
    • /10

      Est $190,021

      Not Listed For Sale

      208 N Academy St, Greensboro, MD 21639

      • 2 Beds
      • 1 Bath
      • 1,236 Sq Ft
      • Built 1925
      208 N Academy St, Greensboro, MD 21639

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Pamela Geib Long & Foster Real Estate, Inc.

  • /2

    $2,500

    Pending
    • Land
    • 20,037 Sq Ft
    • $5,435 per Acre

    0 Houston Branch Rd Unit MDCM2007756, Federalsburg, MD 21632

    ONLINE REAL ESTATE AUCTION TO THE HIGHEST BIDDER OVER $2,500!! Online Bidding Opens - Tuesday, September 15, 2026. Bidding Closes - Thursday, September 17, 2026 at 12:00 PM. List price is opening bid only. Unimproved parcel comprising 0.459 ± acres in Federalsburg, Caroline County. The parcel is primarily surrounded by the State owned Idylwild State Wildlife Management Area. The secluded lot is

    Charles Billig A.J. Billig & Company

    0 Houston Branch Rd Unit MDCM2007756, Federalsburg, MD 21632
  • /37

    $205,000

    Sold Apr 09, 2026

    318 Carter Ave, Denton, MD 21629

    • 2 Beds
    • 2 Baths
    • 606 Sq Ft
    • Built 1950

    Last Sold Summary

    • $338/SF
    • 96 Days On Market

    Current Estimated Value $202,029

    Last Listing Agent Georgi Chauvin Benson & Mangold, LLC

    318 Carter Ave, Denton, MD 21629
    • /32

      Est $234,430

      Not Listed For Sale

      1303 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,816 Sq Ft
      • Built 2004
      1303 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Justin Pokrywka Taylor Properties

  • /57

    $955,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,468 Sq Ft

    8851 New Bridge Rd, Denton, MD 21629

    Private Waterfront Retreat on the Choptank River.Experience the best of Eastern Shore waterfront living in this exceptional home built in 2021, where modern luxury, privacy, and serene views come together on one remarkable property. Situated on 8.15± private acres with approximately 600 feet of Choptank River frontage and deep water access, this stunning retreat offers the perfect balance of

    Shawn Moore Meredith Fine Properties

    8851 New Bridge Rd, Denton, MD 21629
  • /60

    $400,000

    Sold Jan 06, 2026

    106 Briarwood Cir, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,551 Sq Ft
    • Built 2021

    Last Sold Summary

    • $157/SF
    • 4 Days On Market

    Current Estimated Value $406,147

    Last Listing Agent Stephanie Smith Douglas Realty, LLC

    106 Briarwood Cir, Denton, MD 21629
    • /26

      Est $621,637

      Not Listed For Sale

      6105 Laurel Grove Rd, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 1988
      6105 Laurel Grove Rd, Denton, MD 21629

      Last Sold Summary

      • 301 Days On Market

      Last Listing Agent Mickey Hayward Sunset Properties

  • /41

    $579,900

    • 4 Beds
    • 2.5 Baths
    • 2,643 Sq Ft

    24766 Tribbett Cir, Ridgely, MD 21660

    Welcome to this meticulously crafted 2023 contemporary farmhouse, perfectly positioned on a spacious .85-acre lot in the established community of Ashworth. Offering 3,168 square feet, 4 bedrooms, and 2.5 baths, this beautifully designed home blends timeless farmhouse charm with modern finishes and thoughtful upgrades throughout. The striking exterior showcases classic white siding, bold black

    Barbara McCaffrey Redfin Corp

    24766 Tribbett Cir, Ridgely, MD 21660
  • /20

    $189,000

    Sold Dec 02, 2025

    301 Central Ave, Ridgely, MD 21660

    • 4 Beds
    • 1 Bath
    • 1,706 Sq Ft
    • Built 1860

    Last Sold Summary

    • $111/SF
    • 7 Days On Market

    Current Estimated Value $193,879

    Last Listing Agent Jim Corson Benson & Mangold, LLC

    301 Central Ave, Ridgely, MD 21660
    • /24

      Est $240,502

      Not Listed For Sale

      1706 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,560 Sq Ft
      • Built 2005
      1706 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Mark McGuire Benson & Mangold, LLC

  • /55

    $340,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    306 Caroline Ave, Ridgely, MD 21660

    Charming updated Farmhouse style home with hardwood floors throughout and tiled bathrooms. The open kitchen features quartz countertops, a center island for extra prep space and casual dining, stainless steel appliances, and a tile backsplash. The first floor includes a full bath with a tiled walk-in stall shower, plus a separate laundry/mud room. Dual-zone heating and air for year-round comfort.

    Roger Boyce Chesapeake Real Estate Associates, LLC

    306 Caroline Ave, Ridgely, MD 21660
  • /22

    $364,000

    Sold May 20, 2026

    3 Sunrise Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,292 Sq Ft
    • Built 2026

    Last Sold Summary

    • $282/SF
    • 134 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    3 Sunrise Ave, Ridgely, MD 21660
    • /59

      Est $313,809

      Not Listed For Sale

      403 Mallard Dr, Greensboro, MD 21639

      • 3 Beds
      • 2.5 Baths
      • 1,456 Sq Ft
      • Built 2005
      403 Mallard Dr, Greensboro, MD 21639

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Angela Demattia Berkshire Hathaway HomeServices PenFed Realty

  • /8

    $69,000

    $16K PRICE DROP
    • Land
    • 32,234 Sq Ft
    • $93,243 per Acre

    0 Mill & Lincoln St, Greensboro, MD 21639

    With LAND becoming less and less available, here is your opportunity to own 3 PARCELS in the Town of Greensboro!! At least one of which has a hooked up Water/Sewer account, so INSTANT SAVINGS on no tap fee!! AND WITH THIS NEW PRICE, DON'T HESITATE -- GREAT PRICE & GREAT OPPORTUNITY! Parcels are believed to total approximately 0.74 Acres, more or less. Abandoned dwelling exists in the center of

    Erin Anderson Chesapeake Real Estate Associates, LLC

    0 Mill & Lincoln St, Greensboro, MD 21639
  • /21

    $249,500

    Sold Nov 10, 2025

    529 N 6th St, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,019 Sq Ft
    • Built 1930

    Last Sold Summary

    • $245/SF
    • 62 Days On Market

    Current Estimated Value $242,112

    Last Listing Agent Cody Weese Weese Properties, LLC

    529 N 6th St, Denton, MD 21629
    • /11

      Est $292,446

      Not Listed For Sale

      112 Carolin Ct, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1977
      112 Carolin Ct, Preston, MD 21655

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Andrew Beaven Wright Real Estate

  • /6

    $49,900

    • Land
    • 2.55 Acres
    • $19,569 per Acre

    0 Havercamp Rd, 4, Preston, MD 21655

    If you’ve been searching for a private, wooded homesite without feeling too far removed from everyday conveniences, this is it. Offering over 2.5 acres, this property provides the perfect blend of seclusion and accessibility—ideal for building your dream home exactly the way you envision it. Located on Havercamp Rd, you’ll enjoy a peaceful, tucked-away setting while still being just minutes from

    Aubrey Campbell Keller Williams Realty Delmarva

    0 Havercamp Rd, 4, Preston, MD 21655
  • /2

    $399,000

    Sold Jul 14, 2026

    24254 Mallow Dr, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • Built 1999

    Last Sold Summary

    • $242/SF
    • 7 Days On Market

    Current Estimated Value $397,642

    Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

    24254 Mallow Dr, Preston, MD 21655
    • /30

      Est $478,256

      Not Listed For Sale

      25778 Herring Ln, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,608 Sq Ft
      • Built 1989
      25778 Herring Ln, Denton, MD 21629

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Bonnie Johnson Keller Williams Realty

  • /31

    $269,000

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

    108 N Academy St, Greensboro, MD 21639

    This charming cape cod home is waiting for your creative touches! Lots of room on three floors. The main floor boasts a large living room with new vinyl flooring. A separate dining room, large kitchen, full bath and mudroom with washer and dryer. The second floor has four spacious bedrooms and a charming vintage bath with claw foot tub! The basement is a perfect place for crafts, hobbies and

    Marcia Rostien Long & Foster Real Estate, Inc.

    108 N Academy St, Greensboro, MD 21639
  • /70

    $325,000

    Sold Mar 12, 2026

    25361 Calvert Dr, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft
    • Built 1989

    Last Sold Summary

    • $224/SF
    • 50 Days On Market

    Current Estimated Value $333,875

    Last Listing Agent Chris Rosendale CR Realty

    25361 Calvert Dr, Greensboro, MD 21639
    • /30

      Est $283,057

      Not Listed For Sale

      429 N 6th St, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,336 Sq Ft
      • Built 1890
      429 N 6th St, Denton, MD 21629

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Robert Bringman Long & Foster Real Estate, Inc.

  • /50

    $469,900

    • 4 Beds
    • 2.5 Baths
    • 2,488 Sq Ft

    9472 Quail Run Rd, Denton, MD 21629

    Discover relaxed country living at 9472 Quail Run Road! This move-in-ready 4-bedroom home features a classic layout designed for both quiet days and easy entertaining. Highlights include an updated kitchen with a central island, a cozy den with a woodstove, and a full basement perfect for projects or extra storage. Brand-new roof and new HVAC system let you move in with confidence. Step outside

    Valerie Brown Coldwell Banker Realty

    9472 Quail Run Rd, Denton, MD 21629
  • /2

    $274,990

    Sold Aug 06, 2026

    125 Hobbs St, Greensboro, MD 21639

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

    Move in Ready Sold Summary

    • 4% Below List Price
    • $233/SF
    • 21 Days On Market

    D.R. Horton Kinnamon Meadows

    125 Hobbs St, Greensboro, MD 21639
    • /28

      Est $204,748

      Not Listed For Sale

      1020 Market St, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 806 Sq Ft
      • Built 1940
      1020 Market St, Denton, MD 21629

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

  • /53

    $525,000

    • 2 Beds
    • 1 Bath
    • 1,292 Sq Ft

    5820 Bell Creek Rd, Preston, MD 21655

    Don’t miss this exceptional 20+/- acre working horse farm thoughtfully designed for both functionality and country living. This well-equipped equestrian property offers everything needed for training, boarding, riding, and daily farm operations. The property features a 36’ x 40’ center-aisle barn with 9 stalls, water, electric, and an insulated tack room, along with a 77’ x 36’ metal barn

    Colleen Smith EXP Realty, LLC

    5820 Bell Creek Rd, Preston, MD 21655
  • /23

    $365,000

    Sold Dec 22, 2025

    8 Sunrise Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,292 Sq Ft
    • Built 2025

    Last Sold Summary

    • $283/SF
    • 6 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    8 Sunrise Ave, Ridgely, MD 21660
    • /7

      Est $222,889

      Not Listed For Sale

      3477 Holland Dr, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,164 Sq Ft
      • Built 1994
      3477 Holland Dr, Federalsburg, MD 21632

      Last Sold Summary

      • 150 Days On Market

      Last Listing Agent KL Harris Mabry Real Estate LLC

  • /51

    $389,900

    • 3 Beds
    • 2 Baths
    • 1,816 Sq Ft

    320 N Main St, Greensboro, MD 21639

    Welcome to 320 N Main St in the charming town of Greensboro! Step inside and discover a home that immediately invites you to kick off your shoes and stay awhile. Situated on a spacious half-acre lot, this 3-bedroom, 2.5-bath home offers the perfect blend of comfort, functionality, and style. The beautifully updated kitchen is sure to impress, featuring a five-burner gas range, stainless steel

    Karen Clark Clark & Co Realty, LLC

    320 N Main St, Greensboro, MD 21639
  • /26

    $310,000

    Sold Jun 12, 2026

    1 Oakview Ct, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,104 Sq Ft
    • Built 1998

    Last Sold Summary

    • 2% Below List Price
    • $281/SF
    • 129 Days On Market

    Current Estimated Value $306,614

    Last Listing Agent Peter Stark Benson & Mangold, LLC

    1 Oakview Ct, Ridgely, MD 21660
    • /12

      Est $217,634

      Not Listed For Sale

      627 Camp Rd, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft
      • Built 1955
      627 Camp Rd, Denton, MD 21629

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Linda Moore Long & Foster Real Estate, Inc.

  • /13

    $65,000

    $10K PRICE DROP Pending
    • Land
    • 3.73 Acres
    • $17,426 per Acre

    2821 Meadowbrook Rd, Federalsburg, MD 21632

    This purchase includes two lots totaling 3.73 acres on the corner of Miles branch Rd and Meadowbrook Rd. Lot #1 is buildable and high (a perc approval was obtained in 2024) - 1.229 acres. Sellers cleared 3/4 of an acre on the buildable lot. Sellers had obtained a building permit that was approved through Caroline County for a 1650 sq ft one story home, plus garage with a well and an septic

    Jordan Larigan LPT Realty, LLC

    2821 Meadowbrook Rd, Federalsburg, MD 21632
  • /2

    $700,000

    Sold Jun 16, 2026

    11745 Eveland Rd, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 924 Sq Ft
    • Built 1992

    Last Sold Summary

    • $758/SF

    Last Listing Agent Michael Doyle Taylor Properties

    11745 Eveland Rd, Ridgely, MD 21660
    • /77

      Est $504,160

      Not Listed For Sale

      22959 Lyn Oaks Dr, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,904 Sq Ft
      • Built 2005
      22959 Lyn Oaks Dr, Preston, MD 21655

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Debbie Lipscomb Benson & Mangold, LLC

  • /28

    $649,997

    • 4 Beds
    • 3.5 Baths
    • 2,758 Sq Ft

    25722 Old Mill Ln, Greensboro, MD 21639

    Spacious, versatile, and made for both everyday living and entertaining, this 4-bedroom, 4.5-bath home offers an incredible amount of space inside and out. The heart of the home is the stunning kitchen, which opens to a large dining area and generous living space, creating an easy flow for gatherings of any size. Each bedroom is spacious and thoughtfully positioned, while the primary suite stands

    Alyson Anderson Allfirst Realty, Inc.

    25722 Old Mill Ln, Greensboro, MD 21639
  • /20

    $55,000

    Sold Apr 13, 2026

    21182 Marsh Creek Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 2006

    Last Sold Summary

    • 8% Below List Price
    • $57/SF
    • 26 Days On Market

    Last Listing Agent Shane Slacum LPT Realty, LLC

    21182 Marsh Creek Rd, Preston, MD 21655
    • /12

      Est $249,613

      Not Listed For Sale

      607 Academy Ave, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,148 Sq Ft
      • Built 1957
      607 Academy Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Lynette Bridges-Catha Hileman Real Estate Inc-Salisbury

Showing Results 601 - 640, Page 16 of 18

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