15,718

Caroline County, MD Homes

Section Image Section Image
    • 8614 Andersontown Rd, Denton, MD 21629
      8614 Andersontown Rd, Denton, MD 21629
      8614 Andersontown Rd, Denton, MD 21629
      /37

      Est $424,150

      Not Listed For Sale

      8614 Andersontown Rd, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 2,300 Sq Ft
      • Built 1880
      8614 Andersontown Rd, Denton, MD 21629

      Last Sold Summary

      • 132 Days On Market

  • 5 Seward Rd, Ridgely, MD 21660
    5 Seward Rd, Ridgely, MD 21660
    5 Seward Rd, Ridgely, MD 21660
    /28

    $359,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,538 Sq Ft

    5 Seward Rd, Ridgely, MD 21660

    Welcome to this beautifully updated 3-bedroom, 2-bath contemporary home offering the perfect blend of modern style and everyday comfort. From the moment you step inside, you'll appreciate the open-concept layout,, abundant natural light, and thoughtfully renovated finishes throughout. The spacious living areas flow seamlessly into the updated kitchen featuring nice cabinetry, modern countertops,

    James DiPietro Keller Williams Select Realtors of Annapolis

    5 Seward Rd, Ridgely, MD 21660
  • 318 S 5th Ave, Denton, MD 21629
    318 S 5th Ave, Denton, MD 21629
    /2

    $258,000

    Sold Aug 18, 2025

    318 S 5th Ave, Denton, MD 21629

    • 2 Beds
    • 1.5 Baths
    • 1,326 Sq Ft
    • Built 1953

    Last Sold Summary

    • $195/SF
    • 1 Day On Market

    Current Estimated Value $250,237

    Last Listing Agent Barbara Beaudet Brenton Realty Group

    318 S 5th Ave, Denton, MD 21629
    • 309 S University Ave, Federalsburg, MD 21632
      309 S University Ave, Federalsburg, MD 21632
      309 S University Ave, Federalsburg, MD 21632
      /9

      Est $165,102

      Not Listed For Sale

      309 S University Ave, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,296 Sq Ft
      • Built 1925
      309 S University Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 507 Days On Market

  • 103 Park Ave Unit 36203273, Greensboro, MD 21639
    103 Park Ave Unit 36203273, Greensboro, MD 21639
    103 Park Ave Unit 36203273, Greensboro, MD 21639
    /22

    $269,990

    New Construction
    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft

    Perry Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Perry, a 1,059 square foot open concept cottage-style ranch home, offers two bedrooms and two bathrooms. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests or enjoying family time. The well-equipped kitchen is complete with modern cabinetry, stainless steel appliances, a spacious peninsula

    D.R. Horton Builder
    103 Park Ave Unit 36203273, Greensboro, MD 21639
  • 1208 Painted Fern Rd, Denton, MD 21629
    1208 Painted Fern Rd, Denton, MD 21629
    1208 Painted Fern Rd, Denton, MD 21629
    /39

    $400,000

    Sold Dec 12, 2025

    1208 Painted Fern Rd, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,994 Sq Ft
    • Built 2006

    Last Sold Summary

    • $134/SF
    • 8 Days On Market

    Current Estimated Value $397,984

    Last Listing Agent Janet Powers Berkshire Hathaway Homeservice Homesale Realty

    1208 Painted Fern Rd, Denton, MD 21629
    • 4925 Edmondson Creek Rd, Preston, MD 21655
      4925 Edmondson Creek Rd, Preston, MD 21655
      4925 Edmondson Creek Rd, Preston, MD 21655
      /58

      Est $487,321

      Not Listed For Sale

      4925 Edmondson Creek Rd, Preston, MD 21655

      • 4 Beds
      • 3 Baths
      • 1,988 Sq Ft
      • Built 1981
      4925 Edmondson Creek Rd, Preston, MD 21655

      Last Sold Summary

      • 27 Days On Market

  • 27202 Sandtown Rd, Goldsboro, MD 21636
    27202 Sandtown Rd, Goldsboro, MD 21636
    27202 Sandtown Rd, Goldsboro, MD 21636
    /18

    $115,000

    $5K PRICE DROP
    • Land
    • 1.89 Acres
    • $60,847 per Acre

    27202 Sandtown Rd, Goldsboro, MD 21636

    Discover the perfect blend of tranquility and convenience with this perc-approved 1.88-acre homesite, ready for your dream build. Overlooking a scenic tributary of the Upper Choptank River, this property offers breathtaking natural views and a serene setting that wildlife enthusiasts will truly appreciate. Ducks and geese are common visitors on the water with fishing right in your back yard.

    Brett Schrader Taylor Properties

    27202 Sandtown Rd, Goldsboro, MD 21636
  • 25612 Auction Rd, Federalsburg, MD 21632
    25612 Auction Rd, Federalsburg, MD 21632
    25612 Auction Rd, Federalsburg, MD 21632
    /71

    $429,000

    Sold Jul 07, 2025

    25612 Auction Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,648 Sq Ft
    • Built 1984

    Last Sold Summary

    • $260/SF
    • 29 Days On Market

    Current Estimated Value $443,707

    Last Listing Agent Megan Rosendale Rosendale Realty

    25612 Auction Rd, Federalsburg, MD 21632
    • 25698 Caroline St, Greensboro, MD 21639
      25698 Caroline St, Greensboro, MD 21639
      25698 Caroline St, Greensboro, MD 21639
      /26

      Est $391,328

      Not Listed For Sale

      25698 Caroline St, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 2008
      25698 Caroline St, Greensboro, MD 21639

      Last Sold Summary

      • 50 Days On Market

  • 26606 Idlewild Rd, Federalsburg, MD 21632
    26606 Idlewild Rd, Federalsburg, MD 21632
    26606 Idlewild Rd, Federalsburg, MD 21632
    /24

    $249,900

    • 3 Beds
    • 1.5 Baths
    • 864 Sq Ft

    26606 Idlewild Rd, Federalsburg, MD 21632

    Three Bedroom, 1 and a half bathrooms, located on a quiet county road. This house has been freshly painted inside and outside, new LVP flooring installed throughout the house, all interior doors have been replaced with white six panel doors and new light fixtures in each room. New washer/dryer and refrigerator installed, heat pump is 1 year old, and there is a 22 kw Generac generator as a backup

    Robert Bringman Long & Foster Real Estate, Inc.

    26606 Idlewild Rd, Federalsburg, MD 21632
  • 417 N Academy St, Greensboro, MD 21639
    417 N Academy St, Greensboro, MD 21639
    417 N Academy St, Greensboro, MD 21639
    /29

    $209,000

    Sold May 15, 2026

    417 N Academy St, Greensboro, MD 21639

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft
    • Built 1993

    Last Sold Summary

    • 5% Below List Price
    • $223/SF
    • 8 Days On Market

    Current Estimated Value $221,248

    Last Listing Agent Lawrence Doyle Long & Foster Real Estate, Inc.

    417 N Academy St, Greensboro, MD 21639
    • 8157 Arch Dr, Denton, MD 21629
      8157 Arch Dr, Denton, MD 21629
      8157 Arch Dr, Denton, MD 21629
      /34

      Est $332,422

      Not Listed For Sale

      8157 Arch Dr, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,232 Sq Ft
      • Built 1985
      8157 Arch Dr, Denton, MD 21629

      Last Sold Summary

      • 80 Days On Market

  • 410 Wood Duck Dr, Greensboro, MD 21639
    410 Wood Duck Dr, Greensboro, MD 21639
    410 Wood Duck Dr, Greensboro, MD 21639
    /42

    $379,000

    • 4 Beds
    • 3.5 Baths
    • 2,712 Sq Ft

    410 Wood Duck Dr, Greensboro, MD 21639

    Welcome to this spacious three-level home offering flexible living space and a functional floor plan! The main level features a bright living room that flows in the open kitchen. Separate dining room for those family gatherings. Also, on this level is a half bath and a small guest bedroom or turn into your reading area or an office space. Upstairs, you'll find three additional bedrooms and the

    Pamela Geib Long & Foster Real Estate, Inc.

    410 Wood Duck Dr, Greensboro, MD 21639
  • 5213A Bethlehem Rd, Preston, MD 21655
    5213A Bethlehem Rd, Preston, MD 21655
    5213A Bethlehem Rd, Preston, MD 21655
    /50

    $875,000

    Sold Jul 11, 2025

    5213A Bethlehem Rd, Preston, MD 21655

    • 4 Beds
    • 3.5 Baths
    • 2,993 Sq Ft
    • Built 2014

    Last Sold Summary

    • $292/SF
    • 3 Days On Market

    Current Estimated Value $901,565

    Last Listing Agent Amanda Morgan Brenton Realty Group

    5213A Bethlehem Rd, Preston, MD 21655
    • 113 N Main St, Greensboro, MD 21639
      113 N Main St, Greensboro, MD 21639
      113 N Main St, Greensboro, MD 21639
      /24

      Est $244,046

      Not Listed For Sale

      113 N Main St, Greensboro, MD 21639

      • 4 Beds
      • 1.5 Baths
      • 3,540 Sq Ft
      • Built 1926
      113 N Main St, Greensboro, MD 21639

      Last Sold Summary

      • 54 Days On Market

  • 9472 Quail Run Rd, Denton, MD 21629
    9472 Quail Run Rd, Denton, MD 21629
    9472 Quail Run Rd, Denton, MD 21629
    /24

    $490,000

    $8K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,720 Sq Ft

    9472 Quail Run Rd, Denton, MD 21629

    Welcome Home!! Lots of upsides on this 4 bedroom, 2.5 bath home. Harwood floors throughout, new roof in 2024, 8-mini splits for comfort and efficiency. Enjoy the summer evenings on the screened-in deck with fans and lights. Enjoy the summer days with the family making trails through the woods and dip your toes in the creek running through the back of the property. Approx. 24' x 28' work shop or

    J D Fisher Hostetter Realty

    9472 Quail Run Rd, Denton, MD 21629
  • 534 N N 6th St, Denton, MD 21629
    534 N N 6th St, Denton, MD 21629
    /2

    $11,000

    Sold Jul 02, 2025

    534 N N 6th St, Denton, MD 21629

    • Land
    • 22,215 Sq Ft
    • $21,569 per Acre

    Last Sold Summary

    • 370 Days On Market

    Current Estimated Value $171,500

    Last Listing Agent Heather Brummell Keller Williams Realty

    534 N N 6th St, Denton, MD 21629
    • 22818 Marsh Creek Rd, Preston, MD 21655
      22818 Marsh Creek Rd, Preston, MD 21655
      22818 Marsh Creek Rd, Preston, MD 21655
      /15

      Est $223,887

      Not Listed For Sale

      22818 Marsh Creek Rd, Preston, MD 21655

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1976
      22818 Marsh Creek Rd, Preston, MD 21655

      Last Sold Summary

      • 12 Days On Market

  • 608 Market St, Denton, MD 21629
    608 Market St, Denton, MD 21629
    608 Market St, Denton, MD 21629
    /40

    $350,000

    Open Sat 11AM - 1PM $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,056 Sq Ft

    608 Market St, Denton, MD 21629

    Full Re-Hab 2023! Home shows well. The best of Downtown Living! This refurbished Farmhouse, has all the feels of intown country living with all the new modern ammenties! Large Eat- in Kitchen with Tons of Storage! Family Room with Fireplace, leads to a side yard Patio for entertaining! Upstairs you will find three nice size Bedrooms, 2 Full Baths, and a Loft area. Attic has finished space

    Kathleen Brenton Brenton Realty Group

    608 Market St, Denton, MD 21629
  • 2570 Guard Rd, Federalsburg, MD 21632
    2570 Guard Rd, Federalsburg, MD 21632
    2570 Guard Rd, Federalsburg, MD 21632
    /66

    $470,000

    Sold Dec 30, 2025

    2570 Guard Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Built 2020

    Last Sold Summary

    • $196/SF
    • 96 Days On Market

    Current Estimated Value $485,594

    Last Listing Agent Thomas Burdett Keller Williams Realty

    2570 Guard Rd, Federalsburg, MD 21632
    • 505 Teal Cir, Greensboro, MD 21639
      505 Teal Cir, Greensboro, MD 21639
      505 Teal Cir, Greensboro, MD 21639
      /43

      Est $331,303

      Not Listed For Sale

      505 Teal Cir, Greensboro, MD 21639

      • 4 Beds
      • 2.5 Baths
      • 1,952 Sq Ft
      • Built 2004
      505 Teal Cir, Greensboro, MD 21639

      Last Sold Summary

      • 20 Days On Market

  • 13926 Quail Ct, Greensboro, MD 21639
    13926 Quail Ct, Greensboro, MD 21639
    13926 Quail Ct, Greensboro, MD 21639
    /24

    $445,000

    New Construction $4K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,712 Sq Ft

    13926 Quail Ct, Greensboro, MD 21639

    Brand‐new construction in a peaceful country setting! Enjoy effortless one‐level living in this bright, open‐concept rancher designed for comfort and convenience. The spacious living, dining, and kitchen areas flow seamlessly together, creating an inviting space for everyday life and entertaining. The expansive primary suite sits privately on one side of the home and features a walk‐in closet and

    Amanda Morgan Brenton Realty Group

    13926 Quail Ct, Greensboro, MD 21639
  • 282 Tidewater Cir, Preston, MD 21655
    282 Tidewater Cir, Preston, MD 21655
    282 Tidewater Cir, Preston, MD 21655
    /33

    $449,000

    Sold Feb 27, 2026

    282 Tidewater Cir, Preston, MD 21655

    • 4 Beds
    • 2.5 Baths
    • 2,946 Sq Ft
    • Built 2006

    Last Sold Summary

    • $152/SF
    • 14 Days On Market

    Current Estimated Value $445,466

    Last Listing Agent Heather Brummell Keller Williams Realty

    282 Tidewater Cir, Preston, MD 21655
    • 316 N Main St, Greensboro, MD 21639
      316 N Main St, Greensboro, MD 21639
      316 N Main St, Greensboro, MD 21639
      /28

      Est $210,176

      Not Listed For Sale

      316 N Main St, Greensboro, MD 21639

      • 3 Beds
      • 1.5 Baths
      • 1,272 Sq Ft
      • Built 1910
      316 N Main St, Greensboro, MD 21639

      Last Sold Summary

      • 143 Days On Market

  • 0 Goldsboro Rd Unit MDCM2006720, Denton, MD 21629
    0 Goldsboro Rd Unit MDCM2006720, Denton, MD 21629
    0 Goldsboro Rd Unit MDCM2006720, Denton, MD 21629
    /3

    $69,000

    • Land
    • 2.08 Acres
    • $33,173 per Acre

    0 Goldsboro Rd Unit MDCM2006720, Denton, MD 21629

    Beautiful 2.08 acre flat lot. Was approved for a potential mound system in 1991. All paperwork is included in the disclosures. Buyer to verify well and septic approval before closing.

    Toni Lynne Advance Realty, Inc.

    0 Goldsboro Rd Unit MDCM2006720, Denton, MD 21629
  • 116 Stonesifer Dr, Greensboro, MD 21639
    116 Stonesifer Dr, Greensboro, MD 21639
    116 Stonesifer Dr, Greensboro, MD 21639
    /19

    $189,900

    Sold Dec 29, 2025

    116 Stonesifer Dr, Greensboro, MD 21639

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft
    • Built 1954

    Last Sold Summary

    • $226/SF
    • 2 Days On Market

    Current Estimated Value $183,517

    Last Listing Agent Brett Schrader Taylor Properties

    116 Stonesifer Dr, Greensboro, MD 21639
    • 25720 Burrsville Rd, Denton, MD 21629
      25720 Burrsville Rd, Denton, MD 21629
      25720 Burrsville Rd, Denton, MD 21629
      /51

      Est $320,981

      Not Listed For Sale

      25720 Burrsville Rd, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 936 Sq Ft
      • Built 1999
      25720 Burrsville Rd, Denton, MD 21629

      Last Sold Summary

      • 27 Days On Market

  • 11 9th St, Ridgely, MD 21660
    11 9th St, Ridgely, MD 21660
    11 9th St, Ridgely, MD 21660
    /53

    $265,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    11 9th St, Ridgely, MD 21660

    Nestled at the end of a quiet street in the quaint town of Ridgely, you will find this beautifully maintained Rancher. The current owner has completed about everything imaginable to this wonderful home, including but not limited to the Windows, HVAC, Architectural shingled roof, Refrigerator and Stove..... even the crawl space has been encapsulated with a French drain, humidifier and sump pump.

    Michael Rosendale Rosendale Realty

    11 9th St, Ridgely, MD 21660
  • 406 Morning Glory Dr, Denton, MD 21629
    406 Morning Glory Dr, Denton, MD 21629
    406 Morning Glory Dr, Denton, MD 21629
    /50

    $400,000

    Sold May 04, 2026

    406 Morning Glory Dr, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,731 Sq Ft
    • Built 2020

    Last Sold Summary

    • $146/SF
    • 140 Days On Market

    Current Estimated Value $404,414

    Last Listing Agent Mary Stevens Long & Foster Real Estate, Inc.

    406 Morning Glory Dr, Denton, MD 21629
    • 1524 Cattail Commons Way, Denton, MD 21629
      1524 Cattail Commons Way, Denton, MD 21629
      1524 Cattail Commons Way, Denton, MD 21629
      /35

      Est $410,678

      Not Listed For Sale

      1524 Cattail Commons Way, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,492 Sq Ft
      • Built 2007
      1524 Cattail Commons Way, Denton, MD 21629

      Last Sold Summary

      • 18 Days On Market

  • 25548 Hill Rd, Greensboro, MD 21639
    25548 Hill Rd, Greensboro, MD 21639
    25548 Hill Rd, Greensboro, MD 21639
    /13

    $435,000

    • Studio
    • 7,260 Sq Ft

    25548 Hill Rd, Greensboro, MD 21639

    HUGE POTENTIAL. Residential/commercial property combined. 4 residential units available. Two units occupied with annual leases (one at $700.00 and the other at $725.00). Two units vacant (one needs some work and the other needs extensive work. All 4 units are Certified Lead Free. Large main section is gutted and has excellent potential for apartments, etc. Buyer and or Buyer's agent to

    Rosa Tyre Kelark Real Estate

    25548 Hill Rd, Greensboro, MD 21639
  • 14990 Greensboro Rd, Goldsboro, MD 21636
    14990 Greensboro Rd, Goldsboro, MD 21636
    14990 Greensboro Rd, Goldsboro, MD 21636
    /51

    $400,000

    Sold Jan 14, 2026

    14990 Greensboro Rd, Goldsboro, MD 21636

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft
    • Built 1994

    Last Sold Summary

    • $198/SF
    • 58 Days On Market

    Current Estimated Value $409,647

    Last Listing Agent Andrew Beaven Wright Real Estate

    14990 Greensboro Rd, Goldsboro, MD 21636
    • 10767 Collinswood Dr, Denton, MD 21629
      10767 Collinswood Dr, Denton, MD 21629
      10767 Collinswood Dr, Denton, MD 21629
      /32

      Est $478,959

      Not Listed For Sale

      10767 Collinswood Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,182 Sq Ft
      • Built 2006
      10767 Collinswood Dr, Denton, MD 21629

      Last Sold Summary

      • 17 Days On Market

  • 24899 Woods Dr, Denton, MD 21629
    24899 Woods Dr, Denton, MD 21629
    24899 Woods Dr, Denton, MD 21629
    /41

    $474,900

    $8K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 1,738 Sq Ft

    24899 Woods Dr, Denton, MD 21629

    Thoughtfully updated and exceptionally versatile, this well-maintained home is tucked away at the end of a quiet cul-de-sac with no HOA and backs to the Caroline Country Club, offering a peaceful setting and beautiful outdoor views. Major systems including the roof, septic, HVAC and well, were completed in 2017–2018, providing long-term peace of mind.The main home features many original

    Judith Germain Benson & Mangold, LLC

    24899 Woods Dr, Denton, MD 21629
  • 0 Laurel Ln, Denton, MD 21629
    0 Laurel Ln, Denton, MD 21629
    0 Laurel Ln, Denton, MD 21629
    /6

    $77,500

    Sold May 14, 2026

    0 Laurel Ln, Denton, MD 21629

    • Land
    • 1.15 Acres
    • $67,391 per Acre

    Last Sold Summary

    • 649 Days On Market

    Last Listing Agent Michael Bozek Michael J. Bozek

    0 Laurel Ln, Denton, MD 21629
    • 110 S 8th St, Denton, MD 21629
      110 S 8th St, Denton, MD 21629
      110 S 8th St, Denton, MD 21629
      /22

      Est $362,746

      Not Listed For Sale

      110 S 8th St, Denton, MD 21629

      • 3 Beds
      • 3.5 Baths
      • 1,654 Sq Ft
      • Built 1972
      110 S 8th St, Denton, MD 21629

      Last Sold Summary

      • 4 Days On Market

  • 21611 Everlea Dr, Preston, MD 21655
    21611 Everlea Dr, Preston, MD 21655
    21611 Everlea Dr, Preston, MD 21655
    /13

    $315,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    21611 Everlea Dr, Preston, MD 21655

    Welcome to this estate sale opportunity offering convenient one-level living in a wonderful, well-established community just minutes from Easton and St. Michaels. Lovingly owned by the original owner, this 3-bedroom, 2-bath home is ready for its next chapter. The home features a functional floor plan with spacious living areas and offers great potential for updates to match your personal style.

    Nicole Giordano Coldwell Banker Waterman Realty

    21611 Everlea Dr, Preston, MD 21655
  • 113 Maple Ave, Goldsboro, MD 21636
    113 Maple Ave, Goldsboro, MD 21636
    113 Maple Ave, Goldsboro, MD 21636
    /17

    $231,000

    Sold Mar 27, 2026

    113 Maple Ave, Goldsboro, MD 21636

    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft
    • Built 1875

    Last Sold Summary

    • $160/SF
    • 84 Days On Market

    Current Estimated Value $233,229

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    113 Maple Ave, Goldsboro, MD 21636
    • 116 Main St, Preston, MD 21655
      116 Main St, Preston, MD 21655
      116 Main St, Preston, MD 21655
      /20

      Est $251,836

      Not Listed For Sale

      116 Main St, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,185 Sq Ft
      • Built 1920
      116 Main St, Preston, MD 21655

      Last Sold Summary

      • 58 Days On Market

Showing Results 281 - 320, Page 8 of 18

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