15,625

Caroline County, MD Homes

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  • /16

    $299,900

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,892 Sq Ft

    11502 Greensboro Rd, Greensboro, MD 21639

    This is an auction property.This property has been placed in an upcoming event. Please reach out to the listing agent on where the bids are to be submitted. Please submit any pre-auction offer received through the property details page, please reach out to the listing agent. Any post-auction offers will need to be submitted directly to the listing agent. Response within 3 business days. All

    Pamela Geib Long & Foster Real Estate, Inc.

    11502 Greensboro Rd, Greensboro, MD 21639
  • /4

    $225,000

    Sold Jul 30, 2026

    12191 Knife Box Rd, Greensboro, MD 21639

    • Land
    • 8.7 Acres
    • $25,862 per Acre

    Last Sold Summary

    • 8 Days On Market

    Current Estimated Value $569,742

    Last Listing Agent Todd McGill ExecuHome Realty

    12191 Knife Box Rd, Greensboro, MD 21639
    • /22

      Est $410,752

      Not Listed For Sale

      24771 Woods Dr, Denton, MD 21629

      • 3 Beds
      • 3 Baths
      • 1,816 Sq Ft
      • Built 1991
      24771 Woods Dr, Denton, MD 21629

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Brian Gearhart Benson & Mangold, LLC

  • /123

    $679,000

    • 3 Beds
    • 4 Baths
    • 2,756 Sq Ft

    4 S 1st St, Denton, MD 21629

    Outstanding Business Opportunity! Rare Find with-in Downtown Denton! Property would make an excellent Restaurant, Bar, great Venue , or a Large Victorian Home! Features include but not limited to Residential, Commerical or Mixed Use. Large Wrap around Porch for entertaining, Patio with plenty of room for seating with Firepit. Park like setting with Open Space and Large Pond! Town ERU's are

    Kathleen Brenton Brenton Realty Group

    4 S 1st St, Denton, MD 21629
  • /20

    $294,000

    Sold Oct 24, 2025

    512 Lincoln St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft
    • Built 2024

    Last Sold Summary

    • $207/SF
    • 28 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    512 Lincoln St, Denton, MD 21629
    • /30

      Est $280,138

      Not Listed For Sale

      1622 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 4 Baths
      • 2,244 Sq Ft
      • Built 2006
      1622 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Jason Dey Kevin Dey Realty

  • /18

    $340,000

    $35K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,286 Sq Ft

    27279 Jenny Hye Ln, Marydel, MD 21649

    Welcome to Your Peaceful Retreat!This 3-bedroom, 2.5-bath split-foyer home offers 1,488 sq. ft. of comfortable living space, plus a full basement and an attached one-car garage. With its classic brick-and-siding exterior, inviting front patio, and serene surroundings, this property blends warmth, character, and endless potential.Step inside and imagine the possibilities—a bright, open

    Hudson Post Keller Williams Select Realtors of Easton

    27279 Jenny Hye Ln, Marydel, MD 21649
  • /41

    $325,000

    Sold Feb 27, 2026

    406 Wood Duck Dr, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,364 Sq Ft
    • Built 2003

    Last Sold Summary

    • $238/SF
    • 114 Days On Market

    Current Estimated Value $331,452

    Last Listing Agent Brittany Gough Samson Properties

    406 Wood Duck Dr, Greensboro, MD 21639
    • /25

      Est $339,298

      Not Listed For Sale

      407 Maryland Ave, Ridgely, MD 21660

      • 4 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 1902
      407 Maryland Ave, Ridgely, MD 21660

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent Eric Haro The Parker Group

  • /23

    $294,990

    New Construction Pending
    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    119 Hobbs St, Greensboro, MD 21639

    Welcome to 119 Hobbs Street where a to-be-built new home can be yours in Kinnamon Meadows in Greensboro, MD. This home is not currently under construction but is one of the floorplans you can choose to build within this community. Prices vary based on selected upgrades, and prices shown generally refer to the base house without optional features. You’ll work with the builder to select from the

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

    119 Hobbs St, Greensboro, MD 21639
  • /33

    $435,000

    Sold Aug 29, 2025

    22716 Havercamp Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,192 Sq Ft
    • Built 2007

    Last Sold Summary

    • $198/SF
    • 72 Days On Market

    Current Estimated Value $461,075

    Last Listing Agent Chuck Mangold Benson & Mangold, LLC

    22716 Havercamp Rd, Preston, MD 21655
    • /44

      Est $324,961

      Not Listed For Sale

      618 Liberty Rd, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 1957
      618 Liberty Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 251 Days On Market

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

  • /5

    $130,000

    • Land
    • 8.85 Acres
    • $14,689 per Acre

    15589 Union Rd, Goldsboro, MD 21636

    25309 Golt farm Ln has an old vacant double-wide on it . PLEASE DO NOT GO INSIDE THE FLOORS ARE NOT SAFE TO GO IN.

    Diane Wenk Wright Real Estate

    15589 Union Rd, Goldsboro, MD 21636
  • /41

    $270,000

    Sold Apr 15, 2026

    306 S Main St, Federalsburg, MD 21632

    • 4 Beds
    • 1.5 Baths
    • 2,820 Sq Ft
    • Built 1908

    Last Sold Summary

    • $96/SF
    • 139 Days On Market

    Current Estimated Value $266,476

    Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

    306 S Main St, Federalsburg, MD 21632
    • /65

      Est $870,152

      Not Listed For Sale

      25292 Sandy Point Rd, Greensboro, MD 21639

      • 3 Beds
      • 3 Baths
      • 3,334 Sq Ft
      • Built 1966
      25292 Sandy Point Rd, Greensboro, MD 21639

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Kathy Christensen TTR Sotheby's International Realty

  • /10

    $275,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,128 Sq Ft

    21245 Tanyard Rd, Preston, MD 21655

    Charming Country Living with Room to Make It Your Own! Welcome to 21245 Tanyard Road, a spacious rancher with 3 bedrooms and 2 full baths nestled on a peaceful 0.62-acre lot in Preston. Built in 1987, this single-level home offers a solid foundation and a functional layout, ready for your personal touch and updates.Whether you're looking for a primary residence or an investment opportunity,

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    21245 Tanyard Rd, Preston, MD 21655
  • /2

    $286,990

    Sold Aug 15, 2025

    110 Parkland Rd, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 2025

    Last Sold Summary

    • $197/SF
    • 7 Days On Market

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

    110 Parkland Rd, Greensboro, MD 21639
    • /3

      Est $102,333

      Not Listed For Sale

      326 E Central Ave, Federalsburg, MD 21632

      326 E Central Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 125 Days On Market

      Last Listing Agent Barton Johnson/not int Marshy Hope Realty LLC

  • /36

    $380,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 936 Sq Ft

    4455 Smithville Rd, Federalsburg, MD 21632

    This charming ranch-style home, built in 2004, offers a cozy retreat on over 11 acres of serene land, adjoining the picturesque Marshyhope Creek with 3800 acres of Idlewild WMA just across the creek. Inside, discover a traditional floor plan featuring three inviting bedrooms and a country-style kitchen perfect for gatherings. Enjoy the warmth of luxury vinyl plank and carpet flooring throughout.

    Nathan Murray RE/MAX Executive

    4455 Smithville Rd, Federalsburg, MD 21632
  • /2

    $70,000

    Sold Jan 09, 2026

    22415 Hillsboro Rd, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1910

    Last Sold Summary

    • $61/SF
    • 17 Days On Market

    Current Estimated Value $109,265

    Last Listing Agent TAMMY GREEN Samson Properties

    22415 Hillsboro Rd, Denton, MD 21629
    • /12

      Est $259,822

      Not Listed For Sale

      27030 Stafford Rd, Marydel, MD 21649

      • 3 Beds
      • 1 Bath
      • 1,368 Sq Ft
      • Built 1972
      27030 Stafford Rd, Marydel, MD 21649

      Last Sold Summary

      • 352 Days On Market

      Last Listing Agent Myisha Walker EXP Realty, LLC

  • /19

    $435,000

    • 3 Beds
    • 2 Baths
    • 2,408 Sq Ft

    13166 Oakland Rd, Ridgely, MD 21660

    Possibilities! This Caroline County 3-bedroom 2 bath Victorian sitting on almost 4 acres with fencing and plenty of usable buildings in a country setting. Nearby points of interest include Tuckahoe state park with equestrian trails, hiking trails, even a lake to paddle or fish. Gooden Airpark is just down the road along with a few boat ramps to the Choptank River. The property offers several

    BRIAN MORRIS The Land Group

    13166 Oakland Rd, Ridgely, MD 21660
  • /19

    $200,000

    Sold Mar 27, 2026

    409 Main St, Goldsboro, MD 21636

    • 2 Beds
    • 1.5 Baths
    • 1,252 Sq Ft
    • Built 1955

    Last Sold Summary

    • $160/SF
    • 134 Days On Market

    Current Estimated Value $201,292

    Last Listing Agent Amy Betts Coldwell Banker Realty

    409 Main St, Goldsboro, MD 21636
    • /3

      Est $291,997

      Not Listed For Sale

      524 N 6th St, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,348 Sq Ft
      • Built 1994
      524 N 6th St, Denton, MD 21629

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton

  • /8

    $130,000

    • Land
    • 1.01 Acres
    • $128,713 per Acre

    707 W Sunset Ave, Greensboro, MD 21639

    Several individual parcels on Sunset, Cosden and Harold Streets. One parcel has a large 50' x 70' Morton style building, town water is on site and sewer is available. Any interested buyer should perform their own suitable level of due diligence.

    BRIAN MORRIS The Land Group

    707 W Sunset Ave, Greensboro, MD 21639
  • /2

    $274,990

    Sold Dec 16, 2025

    123 Park Ave, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $233/SF
    • 27 Days On Market

    Current Estimated Value $294,243

    D.R. Horton Kinnamon Meadows

    123 Park Ave, Greensboro, MD 21639
    • /13

      Est $318,906

      Not Listed For Sale

      9347 Double Hills Rd, Denton, MD 21629

      • 3 Beds
      • 1.5 Baths
      • 2,080 Sq Ft
      • Built 1900
      9347 Double Hills Rd, Denton, MD 21629

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Andrew Beaven Wright Real Estate

  • /75

    $1,150,000

    • 4,368 Sq Ft

    6354 Statum Rd, Preston, MD 21655

    This wonderful 20 acre property is a horse person’s dream facility. Located in a rural setting, northeast of Preston Maryland. The farm is highlighted by a well-constructed and maintained 75’ x 225’ indoor riding arena, and an 8 stall concrete center aisle horse barn. The barn includes a heated tack room, wash stall with hot water, grooming stall, loft, and overhangs for great ventilation.

    A. John Price Patterson-Schwartz-Middletown

    6354 Statum Rd, Preston, MD 21655
  • /43

    $245,000

    Sold Mar 18, 2026

    511 Bernard Ave, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,385 Sq Ft
    • Built 1950

    Last Sold Summary

    • $177/SF
    • 118 Days On Market

    Current Estimated Value $252,565

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    511 Bernard Ave, Greensboro, MD 21639
    • /12

      Est $333,715

      Not Listed For Sale

      2 Greenridge Ave, Ridgely, MD 21660

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1991
      2 Greenridge Ave, Ridgely, MD 21660

      Last Sold Summary

      • 101 Days On Market

      Last Listing Agent Sebastian Martinez Samson Properties

  • /62

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    1010 S 2nd St, Denton, MD 21629

    Nestled on the edge of town, 1010 S 2nd Street delivers the convenience of in-town living without in-town taxes. Situated on 1.06 beautifully landscaped acres with mature plantings, this 3-bedroom, 2-bath home offers a spacious feel inside and out. Interior features include hardwood, LVP, and tile flooring, along with a cozy pellet stove fireplace insert for efficient heating, complemented by hot

    Roger Boyce Chesapeake Real Estate Associates, LLC

    1010 S 2nd St, Denton, MD 21629
  • /18

    $300,000

    Sold Nov 20, 2025

    202 Maryland Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2000

    Last Sold Summary

    • $223/SF
    • 123 Days On Market

    Current Estimated Value $302,184

    Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    202 Maryland Ave, Ridgely, MD 21660
    • /25

      Est $299,761

      Not Listed For Sale

      9585 Legion Rd, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 1,291 Sq Ft
      • Built 1956
      9585 Legion Rd, Denton, MD 21629

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Ralph Harvey ListWithFreedom.com

  • /30

    $259,900

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    325 Carter Ave, Denton, MD 21629

    The joy of one level living!! This home is in Move-in ready condition. Nice size 2 Bedroom 1 Full Bath. Level lot with Patio for enetertaining. Conveniently located within town limits. Shop, parks, restuarants, Brewery.Public Boat ramp to the Choptank River less than a mile.

    Kathleen Brenton Brenton Realty Group

    325 Carter Ave, Denton, MD 21629
  • /43

    $500,000

    Sold May 20, 2026

    300 S 1st St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft
    • Built 1996

    Last Sold Summary

    • 20% Below List Price
    • $309/SF
    • 279 Days On Market

    Current Estimated Value $498,662

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    300 S 1st St, Denton, MD 21629
    • /19

      Est $299,315

      Not Listed For Sale

      11401 Greensboro Rd, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,036 Sq Ft
      • Built 1940
      11401 Greensboro Rd, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Dustin Parker The Parker Group

  • /15

    $450,000

    • 4 Beds
    • 2 Baths
    • 2,111 Sq Ft

    27329 Jenny Hye Ln, Marydel, MD 21649

    Situated on a 1.51 acre lot, backing to woods, this four Bedroom, 2 full bath home's interior has been completely renovated! Kitchen with eat -in area has been updated with new cabinetry, granite countertops & s/s appliances, Separate dining room for those wanting a more formalized area or can be used as a den, Living room with wood burning fireplace leads to expansive family room with access to

    Kathleen May Synergy Realty

    27329 Jenny Hye Ln, Marydel, MD 21649
  • /64

    $565,000

    Sold Oct 08, 2025

    6074 Newton Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft
    • Built 1993

    Last Sold Summary

    • $274/SF
    • 64 Days On Market

    Current Estimated Value $564,164

    Last Listing Agent James Bent Benson & Mangold, LLC

    6074 Newton Rd, Preston, MD 21655
    • /50

      Est $427,977

      Not Listed For Sale

      294 Tidewater Cir, Preston, MD 21655

      • 5 Beds
      • 2.5 Baths
      • 2,886 Sq Ft
      • Built 2006
      294 Tidewater Cir, Preston, MD 21655

      Last Sold Summary

      • 84 Days On Market

      Last Listing Agent Christina Smith Brenton Realty Group

  • /30

    $249,900

    $25K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    205 N Academy St, Greensboro, MD 21639

    Welcome to this fully remodeled ranch, perfectly situated on a level lot on a quiet street. The showstopper kitchen features white shaker cabinets with dovetailed soft-close drawers, white quartz countertops, tile backsplash, and stainless steel appliances. Every inch of this home has been thoughtfully updated with new LVP flooring, plush carpet, fresh paint, and new lighting throughout. The

    Lee Wolff FSBO Broker

    205 N Academy St, Greensboro, MD 21639

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