15,577

Caroline County, MD Homes

Section Image Section Image
  • /3

    $25,000

    • 728 Sq Ft

    23547 Jonestown Ln, Preston, MD 21655

    Build your dream home on this available lot in Preston, Md. Old home on property - either tear down or restore. Buyer to complete due diligence with County

    Dalton Adshead Mabry Real Estate LLC

    23547 Jonestown Ln, Preston, MD 21655
  • /46

    $300,000

    Sold Jul 10, 2026

    209 W Sunset Ave, Greensboro, MD 21639

    • 4 Beds
    • 2.5 Baths
    • 3,250 Sq Ft
    • Built 1910

    Last Sold Summary

    • 9% Below List Price
    • $92/SF
    • 16 Days On Market

    Current Estimated Value $312,662

    Last Listing Agent Teal Clise EXP Realty, LLC

    209 W Sunset Ave, Greensboro, MD 21639
    • /28

      Est $220,221

      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

      Last Listing Agent Marcia Rostien Long & Foster Real Estate, Inc.

  • /29

    $284,900

    $45K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,350 Sq Ft

    115 Boyce Mill Rd, Greensboro, MD 21639

    Welcome to this charming, Cape-Cod with a Full Unfinished basement—perfectly nestled on a spacious 1/2 Acre! This property gives you that “welcome home” feeling the moment you arrive.Inside, you’ll find a bright and inviting living area featuring a cozy electric fireplace insert and beautiful wood‑beam accents. The freshly renovated kitchen is thoughtfully designed and opens seamlessly to

    Kathleen Brenton Brenton Realty Group

    115 Boyce Mill Rd, Greensboro, MD 21639
  • /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 $396,499

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

    406 Morning Glory Dr, Denton, MD 21629
    • /51

      Est $329,696

      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

      Last Listing Agent Jarnell Foster Samson Properties

  • /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
  • /38

    $4,000,000

    Sold Jul 23, 2026

    24795 E Cherry Ln, Greensboro, MD 21639

    • Built 2007

    Last Sold Summary

    • 6 Days On Market

    Current Estimated Value $3,492,000

    Last Listing Agent Debbie Figgs Long & Foster Real Estate, Inc.

    24795 E Cherry Ln, Greensboro, MD 21639
    • /35

      Est $411,412

      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

      Last Listing Agent Niya Davis Century 21 Harris Hawkins & Co.

  • /24

    $199,900

    Under Contract
    • 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
  • /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 $414,249

    Last Listing Agent Andrew Beaven Wright Real Estate

    14990 Greensboro Rd, Goldsboro, MD 21636
    • /32

      Est $489,076

      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

      Last Listing Agent Amanda Morgan Brenton Realty Group

  • /35

    $317,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,936 Sq Ft

    243 Briarwood Cir, Denton, MD 21629

    The Upgrades Are In. All That’s Missing Is You! Move In Ready- Beautifully designed new construction interior townhome located in an established community in the heart of Denton, Maryland! Offering 4 spacious bedrooms, 2.5 baths, and an oversized rear-load garage, this home combines modern style with everyday functionality.The open-concept floor plan is perfect for both entertaining and

    Michelle DiDonato Island Realty, LLC

    243 Briarwood Cir, Denton, MD 21629
  • /62

    $435,000

    Sold Aug 14, 2026

    12397 Ridgely Rd, Ridgely, MD 21660

    • 2 Beds
    • 2 Baths
    • 1,952 Sq Ft
    • Built 1959

    Last Sold Summary

    • 10% Below List Price
    • $223/SF
    • 37 Days On Market

    Current Estimated Value $474,739

    Last Listing Agent Deborah Dawkins Coldwell Banker Realty

    12397 Ridgely Rd, Ridgely, MD 21660
    • /20

      Est $273,476

      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

      Last Listing Agent Henry Gibbons-Neff Meredith Fine Properties

  • /21

    $399,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    11498 Reed Cir, Ridgely, MD 21660

    Welcome Home! Don't miss out on this lovely 3 bdrm/2 bath ranch style home with granite counters, stainless appliances, lovely wooden cabinets in the kitchen leading to a screened in porch overlooking the in ground pool and pastoral views! Situated on just over 1 acre of land with a 2 car detached garage, this home offers privacy and peaceful living. Plenty of room for the camper and boat to be

    Mary Wagner Cummings & Co. Realtors

    11498 Reed Cir, Ridgely, MD 21660
  • /2

    $575,000

    Sold Sep 11, 2026

    23730 Henry Rd, Ridgely, MD 21660

    • 3 Beds
    • 3.5 Baths
    • 3,276 Sq Ft
    • Built 2023

    Last Sold Summary

    • 3% Below List Price
    • $176/SF
    • 77 Days On Market

    Current Estimated Value $585,334

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    23730 Henry Rd, Ridgely, MD 21660
    • /18

      Est $396,141

      Not Listed For Sale

      1308 Trice Meadows Cir, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,505 Sq Ft
      • Built 2007
      1308 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 264 Days On Market

      Last Listing Agent Venita Jacobson CENTURY 21 New Millennium

  • /42

    $359,000

    $20K PRICE DROP
    • 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
  • /30

    $345,000

    Sold Jul 21, 2026

    1309 Fairfield Ct, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,360 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Above List Price
    • $254/SF
    • 3 Days On Market

    Current Estimated Value $330,588

    Last Listing Agent Ashley Yost Douglas Realty, LLC

    1309 Fairfield Ct, Denton, MD 21629
    • /71

      Est $434,276

      Not Listed For Sale

      25612 Auction Rd, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,648 Sq Ft
      • Built 1984
      25612 Auction Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Megan Rosendale Rosendale Realty

  • /44

    $440,000

    • 4 Beds
    • 2 Baths
    • 1,986 Sq Ft

    25699 Auction Rd, Federalsburg, MD 21632

    This 17 acre farmette located just minutes from Federalsburg with proximity to Easton and the MD/DE beaches offers a remodeled bungalow with numerous upgrades. The cropland is currently under cultivation by a local farmer and there are several outbuildings on the property. Electric service has been upgraded to 200 amp and Choptank Electric Coop offers fiber optic. While the improvements are vast,

    Carol Baker-Jones Benson & Mangold, LLC

    25699 Auction Rd, Federalsburg, MD 21632
  • /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
    • /25

      Est $347,923

      Not Listed For Sale

      24636 Williston Rd, Denton, MD 21629

      • 3 Beds
      • 1.5 Baths
      • 1,472 Sq Ft
      • Built 1959
      24636 Williston Rd, Denton, MD 21629

      Last Sold Summary

      • 320 Days On Market

      Last Listing Agent Andrew Beaven Wright Real Estate

  • /20

    $449,000

    New Construction Under Contract
    • 3 Beds
    • 2 Baths

    0 Spiering Dr Unit MDCM2007622, Greensboro, MD 21639

    TBB....This beautifully designed rancher offers 3 bedrooms and 2 full baths with an open-concept floor plan and cathedral ceilings in the main living area. . Enclosed Sunporch that leads to back patio and Front porch for your morning coffee. Enjoy an oversized attached two-car garage and a rear deck perfect for outdoor living. Encapsulated conditioned crawl space . Situated on a cleared 1-acre

    Barbara Blosser Long & Foster Real Estate, Inc.

    0 Spiering Dr Unit MDCM2007622, Greensboro, MD 21639
  • /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 $235,170

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    113 Maple Ave, Goldsboro, MD 21636
    • /27

      Est $161,474

      Not Listed For Sale

      308 Park Ave, Federalsburg, MD 21632

      • 2 Beds
      • 2 Baths
      • 952 Sq Ft
      • Built 1904
      308 Park Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Mary Mabry Mabry Real Estate LLC

  • /40

    $345,000

    $15K 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
  • /2

    $286,990

    Sold Sep 24, 2025

    114 Parkland Rd, Greensboro, MD 21639

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

    Last Sold Summary

    • $197/SF
    • 9 Days On Market

    Last Listing Agent Justin Wood D.R. Horton Realty of Virginia, LLC

    114 Parkland Rd, Greensboro, MD 21639
    • /3

      Est $501,532

      Not Listed For Sale

      12141 Greensboro Rd, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1950
      12141 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent John Carroll Village Real Estate Company LLC

  • /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
  • /23

    $298,990

    Sold Apr 01, 2026

    123 Hobbs St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $245/SF
    • 13 Days On Market

    D.R. Horton Kinnamon Meadows

    123 Hobbs St, Greensboro, MD 21639
    • /22

      Est $264,209

      Not Listed For Sale

      350 Deep Shore Rd, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,350 Sq Ft
      • Built 1965
      350 Deep Shore Rd, Denton, MD 21629

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Barbara Beaudet Brenton Realty Group

  • /20

    $295,000

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

    212 Apple Ln, Preston, MD 21655

    Seller is offering a $4,500 credit for new carpet in all 3 bedrooms! Welcome home to this charming 3-bedroom, 2-bath rancher offering the perfect blend of comfort and convenience. Nestled on a quiet street within the city limits, this property provides a peaceful, country-like setting while remaining just minutes from Easton, Denton, Federalsburg, and Cambridge.Step inside to find luxury

    Kayla Walter Keller Williams Realty

    212 Apple Ln, Preston, MD 21655
  • /52

    $320,000

    Sold Nov 19, 2025

    17635 Cool Spring Rd, Marydel, MD 21649

    • 3 Beds
    • 2 Baths
    • 1,782 Sq Ft
    • Built 1992

    Last Sold Summary

    • $180/SF
    • 18 Days On Market

    Last Listing Agent Daphne Reeve Keller Williams Flagship

    17635 Cool Spring Rd, Marydel, MD 21649
    • /27

      Est $275,863

      Not Listed For Sale

      319 Kerr Ave, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1975
      319 Kerr Ave, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Justin Pokrywka Taylor Properties

  • /33

    $159,000

    Pending
    • 2 Beds
    • 1.5 Baths
    • 968 Sq Ft

    107 N School St Unit 2F, Greensboro, MD 21639

    RARE FIND! Charming, Spacious, Affordable & Move-In Ready! Step into a piece of Greensboro history with this unique second-floor condo located in the original 1922 Greensboro School, thoughtfully converted into 22 individual condo units. This almost 1,000 sq. ft. unit was renovated in 2018 and offers 2 bedrooms and 1.5 baths. An abundance of natural light pours through the impressive oversized,

    Karen Clark Clark & Co Realty, LLC

    107 N School St Unit 2F, Greensboro, MD 21639
  • /19

    $300,000

    Sold Dec 23, 2025

    14 N Maple Ave, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Below List Price
    • $284/SF
    • 46 Days On Market

    Current Estimated Value $292,286

    Last Listing Agent Joshua Clark Clark & Co Realty, LLC

    14 N Maple Ave, Ridgely, MD 21660
    • /40

      Est $633,093

      Not Listed For Sale

      8291 Clearfield Rd, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 2,800 Sq Ft
      • Built 2005
      8291 Clearfield Rd, Denton, MD 21629

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Chris Rosendale CR Realty

  • /13

    $315,000

    $50K PRICE DROP Pending
    • 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

    Nicole Giordano Coldwell Banker Waterman Realty

    21611 Everlea Dr, Preston, MD 21655

Showing Results 281 - 320, Page 8 of 18

How to Buy a Home How to Finance a Home How to Sell a Home